Wealth Actually

BRADY WELLER discusses the intricacies of QSBS rollovers, including eligibility, timing, and strategic planning for founders and investors. The goal is to help the listener maximize tax benefits and navigate the legal complexities of this powerful tool. https://youtu.be/gvQ0ZskvWVI QSBS, tax exemption, startup founders, rollover, legal structuring, investment strategy, tax planning, startup exit, C corporation, Key Topics QSBS eligibility and benefits Challenges in executing rollovers Legal and tax considerations for founders Timing and risk management in rollovers Strategic structuring for maximum benefit “QSBS ROLLOVERS” Sound Bites “60 days is a very short window for founders.” “Rollover continues your holding period clock.” “Partial rollovers are common for founders.” Chapters 00:00 Understanding QSBS and Its Benefits 03:07 Challenges for Founders in QSBS Compliance 05:54 Advising Founders on QSBS Rollovers 08:57 Structuring New Ventures for QSBS Eligibility 12:00 Navigating QSBS for Tech and Non-Tech Founders 14:54 Investor Considerations in QSBS Transactions 17:46 State-Specific QSBS Regulations and Planning 20:57 Future of QSBS and Strategic Planning Resources Brady Weller on LinkedIn qsbsrollover.com qsbsreference.com Frazer Rice and Michael Arlein discuss the nuts and bolts of 1202 QSBS Features for Founders Guest links LinkedIn Transcript Frazer Rice (00:01.314)Welcome aboard, Brady. Brady Weller (QSBS Rollover) (00:03.043)Hey, Frazer, thanks for having me. Frazer Rice (00:04.738)Well, you are the nice compliment to a piece I just did with Michael Arlene on QSBS. We covered some of the nuts and bolts around 1202. You come at it from a little bit different angle. It’s usually where people, founders especially, have issues sort of complying with things like the three and five year rule. And otherwise really maximizing the capability of the rollover and the tax significance for it. Tell us a little bit about who benefits and what you do here. Brady Weller (QSBS Rollover) (00:35.107)Yeah, QSBS is. by far the biggest tax exemption available to individual taxpayers in the U.S. So it’s been something that hasn’t been up. I should say there’s not a massive advisory network around it. So it’s not something that’s been taken advantage of, I think, to its full scope. Michael, who you had on recently, is a top trust and estate planner for founders of companies around QSBS. The specific problem that QSBS rollover solve is for a shareholder of an early stage company. Most often founders or very early investors, say, maybe series A or earlier shareholders. It’s an incentive to basically hold your stock for a quote unquote long time. In this sense, that means, you know, now under some new rules, basically three to five plus years. It’s a tax exemption available to folks who hold their stock for at least five years. Then they can exclude from federal income tax now up to $15 million of gains when they sell that stock. So you have to be a shareholder in an early stage C corporation, early stage company. Frazer Rice (01:50.616).Those founders before three to five years are trying to figure out how to use this tool. What are the challenges in making sure they don’t blow up the transaction by transferring something poorly. Or having their company grow too large or have too much cash or those types of things? Maybe list out a little bit some of the challenges that are out there that that a founder needs to be aware of. Brady Weller (QSBS Rollover) (02:22.509).Yeah. So we don’t have to constantly caveat. I’ll mainly talk as though we’re speaking about the pre July 5th, 2025 rules for QSPS. Anything, any stock issued after that date, middle of last year. is under a slightly different set of rules. They are more expanded rules, but I’ll speak to this sort of from those old rules. And so the old rules state that you have to hold your stock for at least five years. And if you do, you can exclude a large portion from federal income tax, usually $10 million for founders. But if you don’t hold the stock for five years, your only option is to take the cash from that sale. For example, say you sell stock at year three or year four, and purchase new QSBS eligible stock with that cash within 60 days. So it’s sort of like the 1031 exchange. Folks maybe are more familiar with real estate property exchanges. Its sort of like a 1031 exchange for stock. So you take the cash and you purchase a like kind quote unquote asset with it. Now the challenge with that is 60 days is not a very long time. And when you’re a founder of a company who just went through liquidity. You just got your deal done and the whirlwind that that is. Now you’re dealing maybe in a post liquidity world. You’re maybe running another team at the acquirer or you’re otherwise involved. 60 days is not a long time to be able to find and diligence a new opportunity. . It’s just not feasible. Especially for founders to use that cash to say buy stock in someone else’s company. It just doesn’t make sense. Like risk adjusted, I suppose. Frazer Rice (04:05.579)No, it’s a miracle that your company did great. Now you have to go and find another miracle and make it work within 60 days. It’s crazy. Brady Weller (QSBS Rollover) (04:10.143).That that’s the biggest that’s probably the biggest barrier to executing them. For the longest time there just weren’t a lot of people. They hadn’t come alongside founders to help advise them on structured ways that they could do these rollovers. Yeah, the options are risky. It’s like take your money and invest it in Dave’s startup in San Francisco. He’s going to lose your money. So that may be what you want to do with that money. To keep your risk profile sort of moving. But that’s not tax planning in any way. Right. To make that decision just to save on federal income tax might not be the best way to use your rollover. So we’ve seen it much more for angel investors, something that they might use. People who want to maybe have a lot of deal flow. A lot of investment opportunities in front of them. But they want to keep that risk profile moving. I’d say timing and risk are the two biggest challenges when you’re trying to execute a rollover. Frazer Rice (05:13.805).As a detail on that, you’ve got your company. You’ve got $10 million coming to you. Hopefully tax free, similar to a 1031. You don’t have to go into one company, you could go into a basket of companies. Brady Weller (QSBS Rollover) (05:28.579).Yeah, you could take the cash, say you make $10 million from a sale. You could pay taxes on $3 million of it, assuming you haven’t hit your five year requirement. Then, you could roll over the other seven in various other deals. You could put it all into one new company. What the rollover actually does is it continues your holding period clock from the last stock. So if you held for three years in your original company stock, You sell. You’re able to reinvest those proceeds within 60 days. It continues your holding period. Once you’re beyond a combined five the next liquidity event in the second company. Now you have proper seasoning on your shares, for lack of a better word, and then you can sell them under the QSPS exemption. Frazer Rice (06:17.143)So, this gets to what you do on a day-to-day basis. So a founder comes to you and says, all right, I’ve got this situation I think that’s coming. And I need some advice. You’re sort of letting them know what’s happening here. How do you advise them, in a sense, whether it’s through your company or even as a general matter? Do you have a suite of other founders and companies that are out there? And then… Maybe also similar to a 1031, is there sort of an intermediary function that needs to happen in order for the asset or the cash to go into sort of a, for lack of word, like an escrow account to then be deployed correctly into the eligible next company so that you keep that period going. Brady Weller (QSBS Rollover) (06:50.713)Boom. Brady Weller (QSBS Rollover) (07:05.839)That’s a good question. It’s not as formalized as the, you know, in terms of the 1031 world where there’s sort of a designated intermediary and that’s sort of required step in the process. This is very much the wire goes into your checking account for the sale of company A stock. Frazer Rice (07:11.703)Mm-hmm. Brady Weller (QSBS Rollover) (07:22.281)You send a wire back out to purchase stock in company B. When someone comes to us and is looking for guidance on how to do a rollover, sometimes they’ve talked to tax or trust in state attorneys already, or maybe they’re CPA. And there are maybe 50 folks in the US who have, I’d say, Frazer Rice (07:37.463)Sure. Brady Weller (QSBS Rollover) (07:45.07)I call it advanced QSPS planning knowledge, which is they have the trust planning strategies, rollover knowledge, all of these things that sort of at their disposal that they can speak to, but it’s a very small network. so our firm is actually the only non-CPA non-law firm in the country that deals directly with founders on these. And so we ended up kind of playing quarterback, connecting them with the right attorneys, maybe the right CPA, if they don’t have one to make sure that the team is sort of assembled. You know, because the risk profile of taking your money and investing in someone else’s company typically doesn’t align with most founders’ interests at that time, the service that we provide is helping them to roll that money into a new startup of their own. We think these founder-led rollovers where the founder or the shareholder who sold their original stock can now direct the proceeds into a new entity that they own and control. It’s a really great way to execute this. It gives the shareholder, the founder the optimal amount of flexibility and control over the proceeds over time. So they can handle their own risk profile. Frazer Rice (08:57.921)So for the founder who built their business originally, they sell it an

https://youtu.be/FU5IvtBbtCY JOHN SAMUELS from WELLWORTH ADVISORS discusses “HEALTH AS AN ASSET CLASS” and the nuances of personalized healthcare management for high-net-worth individuals. We contrast concierge medicine with comprehensive health advisory services. Learn about his book “WEALTHCARE” which lays out the frameworks of his practice. Finally, John goes into how expert navigation, team-based care, and strategic planning can significantly improve health outcomes and client relationships. Finally we hear a little bit about what his favorite medical shows are on TV! Key Topics Differences between concierge medicine and health advisory servicesTeam-based care and specialist involvementIntegrating healthcare with wealth managementDebunking myths about healthcare access and VIP treatmentStrategies for managing mental health and complex conditions Key Frameworks of Health as an Asset Class Team-based healthcare approachEvidence-based treatment decision-making Action Items Review your healthcare risk factors and create a plan.Organize your medical records and update legal documents.Engage a healthcare advisor to understand your coverage and treatment options. Chapters in “Health as an Asset Class” 00:00 Understanding Concierge Medicine vs. Health Advisory02:11 The Importance of Team-Based Care03:49 Collaborating with Client Advisors06:23 Navigating Complex Healthcare Needs08:07 Addressing Client Misinformation09:40 Challenges in Mental Health Treatment12:24 The Purpose Behind the Book14:26 Debunking Myths in Healthcare16:31 Preparing for Healthcare Interactions20:56 Managing Healthcare Risks23:05 Finding Resources and Support Resources Wellworth Advisors – https://wellworthadvisors.comJohn Samuels’ Book on Healthcare Management – https://www.amazon.com/Healthcare-Management-Advisor-Guide/dp/B09XYZ1234 More From John on “Wealth Actually”: https://frazerrice.com/ep-126-john-samuels/ Guest links Website – https://wellworthadvisors.comEmail – mailto:john@wellworthadvisors.com https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/ Keywords healthcare, concierge medicine, health advisory, high-net-worth individuals, patient navigation, mental health, healthcare risk, medical research, healthcare myths, health insurance Titles Beyond Concierge: The Future of Personalized Healthcare for Wealthy ClientsHow Expert Care Navigation Transforms High-Net-Worth Healthcare Sound Bites “We map out the cost of treatment for clients.”“We focus on evidence-based treatment options.”“VIP care often doesn’t mean better care.”

“Breaking the Glass Ceiling: Julia Carreon’s Fight Against Corporate Gaslighting” In this episode, Frazer Rice sits down with Julia Carreon to explore her recent high-profile litigation against a major financial institution and her powerful insights on women in leadership, corporate culture, and overcoming systemic barriers. YOUTUBE https://youtu.be/e05k7SVQ2xI We discuss: Julia’s experience with workplace gaslighting and her litigation journey with Wells Fargo The importance of transparency, accountability, and protecting yourself in corporate environments How societal and corporate cultures disadvantage women, especially around motherhood and leadership The themes and motivations behind Julia’s book, Walking on Broken Glass Practical strategies women can use to build political capital and safeguard their careers The significance of external networks and understanding your personal strengths The evolving landscape of equity, ownership, and governance in corporations How to proactively prepare for and respond to systemic workplace challenges SPOTIFY https://open.spotify.com/episode/5c546gs6Qctx4bGOvalgXj?si=1dDyJxnwSyu4tnhXxpzVxg Timestamps: 00:00 – Introduction: Julia’s litigation and book overview 02:03 – Gaslighting in corporate culture and early experiences 04:14 – Dealing with systemic backstage politics and fighting for justice 05:10 – Motivations for writing Walking on Broken Glass 08:08 – Diagnosing workplace culture and gender dynamics 09:33 – The weaponized HR department and accountability 11:38 – Protecting yourself: cultural awareness and bias 13:12 – Demographics, gender disparities, and moving forward 15:12 – Institutional misogyny and societal shifts 16:05 – Motherhood, work-life balance, and corporate support 18:28 – Questions of corporate culture change post-COVID 22:21 – The fear factor and change in workplace loyalty 27:12 – Tactical career strategies and building political capital 28:15 – Always Be Executing (ABE) and tracking success 30:53 – The ownership mentality and equity’s role in career resilience 34:45 – Building internal and external networks for support 36:49 – Understanding personal aptitudes through testing and reflection 40:12 – Leveraging political capital and seizing opportunities 43:31 – How to follow Julia and stay updated on her journey Transcript Frazer Rice (00:01.004)Welcome aboard, Julia. Julia (00:03.32)Thanks for having me. Frazer Rice (00:04.652)Well, as I said in the opening, the concept of gaslighting in the boardroom is something that certainly isn’t new, but it doesn’t make it any more comfortable for the people who deal with it on a day-to-day basis or as part of their career. And you’re in the midst of litigation right now with a major financial services company. Maybe talk a little bit about what’s going on there. Julia (00:24.801)Yeah, so I am in a high profile lawsuit with my former employer. I would say this is not a path that anyone chooses on purpose. In my particular case, Frazer, I spent 20 years at Wells Fargo, 15 of which were pretty spectacular. I have come to realize almost maybe fairy tale like in terms of my experience. I want to talk about some of the things later on that made it a fairy tale. So yeah, I wouldn’t have chosen this. I did not see the culture at my former employer coming for me. I was blindsided by it and it got ugly quickly. One of the things that I think I am doing here. Or at least trying to do is not be shy about it. Not hide from it. Try to show women a different way for how to deal with these situations. Because I have very strong feelings about the fact. With the rollback of DEI and the current administration’s point of view on women, that we’re going backwards. If women don’t start fighting for ourselves in a more public way and without fear, then I don’t know where we’re going to be in the next five to 10 years. I am soldiering on and it’s not easy to your point. But it is what it is and it’s a fight that I believe is worthy. Frazer Rice (02:03.608)So it’s a daunting task taking on a big bank. Big financial services firm, whether it’s in this situation or frankly any. It’s just these well-resourced big behemoths. What has been the experience been like so far? As far as gathering information? Of getting the walls built that you need to in order to live your life while you go through this conflict with this bank? Julia (02:29.822)It’s hat that is the million dollar question. Right? I will say that in my case i got really fortunate and came across a quote. It’s going to sound really strange. But i came across a quote that said fear is fake and danger is real but fear is fake. I believe that the patriarchy wants women to be afraid. So it tells us these bad things are going to happen if you take on a big firm like this. It is grueling. The days are long sometimes. But once I internalize the reality that it is all fake in terms of all of the bad things that you think could happen really can’t happen. Worst case scenario, there’s nothing Like I’m not going to die. They’re not going to, you know, take away my family. Like all of these things, right? We tell ourselves that it could get really nasty. And in my case, I have to stay really grounded in the fact that what I’m doing is worthy. We tried my lawyer and I tried for 14 months to come to a different answer. And so in a way, not just telling myself fear is fake. But in another way, I kind of feel like it’s my destiny. Because, I just want to say this real quick, I had 20 years at a place that was not toxic. And so I know what good looks like, and this is not good. So in that way, I really feel like it’s my destiny. And so that’s what you do, and you have to have a good support network. I have a great husband, so that really helps. Frazer Rice (04:14.21)The, as I’ve told people, sometimes doing the right thing or going after something that upholds justice. It can be expensive and hard. I give you kudos for standing up. Not only for yourself, but others who are going through a difficult situation. Where you’ve had a significant wrong done to you. You’ve written a book about this experience as well. We can take some time to think, to talk about what the book tries to do. First of all, writing one in tandem with the process here, I think is a bit unusual. Some people do it after the fact. To go through a catharsis after going through a difficult process. Talk about first the why of the book.thhen we’ll talk a little bit about what you talk about in it. Julia (05:17.241)The book is called Walking on Broken Glass: Navigating the Aftermath of the Glass Ceiling.” It was co-written with a fabulous woman named Shannon Nutter. I hope people follow on LinkedIn. The book is not squarely about what happened to me the book came together. With Shannon and I meeting on LinkedIn. Then discovering that we had a lot of the same shared experiences as we are Gen X. in hindsight. Our generation has had the opportunity to have the most benefit of the Gloria Steinem Women’s Movement. Think about the fact that we got the advantage of the birth control and all of the DEI efforts that have been in the last 15, 20 years. And we really felt like there was still a long way to go. Then all of that is starting to go backwards. So last year when we met or the year before, we’re like, my God, the idea that we got the best of the best is shocking to us. And so what are we going to do about it? We really wanted the book to speak to women of all ages in their career. But it was written from a lens of two then 53 year old women who had seen a lot. We wanted to give the book as a love letter or a gift to our 35 year old self. To say, this is what we should have or wish we had known 20 years ago. Because we would have done things differently if we had really faced kind of what the challenges were that women are facing at work. In a real way right not in a way that sugarcoats it or pretends to throw it under the rug. And or always makes it the woman’s fault like the woman always has to be changing and evolving in order to adapt to the systems and i you know it’s exhausting right so the book was written for that reason and it does tap into a lot of the things that we both experienced. Julia (07:35.17)But it isn’t a kind of a personal journal of what happened to me with my former employer. Frazer Rice (07:39.82)Right, one of the things that I found useful about the book is you divided it into three sections. I think it brings us sort of clarity into what you’re trying to achieve here. The first one is just diagnosing the situation that you’re in. Maybe talk a little bit about that. Part one the understanding of your surroundings. What’s happening around you. The conditions that women are facing as they embark on these big situations in the workplace. Julia (08:08.982)Yeah. So the first part of the book does give a primer on kind of the history of feminism and how did we get here and what are some of the big open questions that are still left to answer. We also want to set the stage that makes it very clear that women are accountable for our actions in the workplace. Like this is not in any way a book that seeks to make someone who’s failing feel good about the fact that they’re failing, right? Shannon and I both reached really high levels of corporate success at major global firm. There is a lot of work to do. So we really try to dimension how, what are some effective ways for you to approach that work? What are some of the pitfalls and how are some of the ways that you can handle that? In a way that’s kind of clear-eyed, but never about putting the blame or the onus on the company. And if you don’t mind, I want to say something about that because it relates to my lawsuit. One of the things that I’ve heard criticisms about is that people on social media often I saw when I kind of scanned the landscape of it recently are, this woman is naive. She thinks. HR is her friend because one of the things t

There is a storm coming with the challenges of navigating the TRUSTEE CRISIS. It is one of the biggest blind spots in the “GREAT WEALTH TRANSFER” and will be the source of mountains of litigation for the unwary, https://youtu.be/hwQev88A03M Summary In this conversation, Frazer Rice and Jennifer Zelvin McCloskey discuss the current crisis in trusteeship, highlighting the shortage of qualified trustees amidst a significant wealth transfer. They explore the importance of modern trust planning, the challenges faced by individual trustees, and the need for better education and training in the field. The discussion also covers the emotional and interpersonal aspects of trusteeship, the functions and responsibilities of trustees, and the necessity of managing risk effectively. They emphasize the importance of building a pipeline for future trustees and improving the perception of the profession, while also identifying opportunities within the trust industry. https://open.spotify.com/episode/4qpkrVdaUa2AfDxgl7j3yN?si=XVgG3jE_Qpqq2JTqi8XLXQ Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Takeaways The coming crisis in trusteeship is already here. There is a significant shortage of qualified trustees. Trusteeship requires strong interpersonal skills and emotional intelligence. Managing risk is a fundamental aspect of trusteeship. Trustees critically need education and training. The role of a trustee is evolving with increasing complexity. Beneficiaries need to understand their rights and the trustee’s role. Custodial responsibilities are essential for asset protection. There are many opportunities for growth in the trust industry. Trust law and investment management are distinct fields. This Episode is for . . . Anyone that has an estate plan with a trust in it and doesn’t know what a trustee does Any advisor who works w/ multi-generational situations (that’s everybody in wealth management) Any RIA looking to sell Financial types worried about compliance world Fiduciary litigators Chapters of “THE TRUSTEE CRISIS: Navigating the Challenges” 00:00 The Coming Crisis in Trusteeship 02:06 Importance of Modern Trust Planning 04:11 Challenges with Individual Trustees 08:03 The Dwindling Pool of Qualified Trustees 10:06 Functions and Responsibilities of a Trustee 12:20 The Emotional and Interpersonal Aspects of Trusteeship 16:05 Managing Risk in Trusteeship 19:07 Building a Pipeline for Future Trustees 22:10 The Role of Education in Trusteeship 25:07 Improving the Perception of Trusteeship 28:19 The Need for Better Trust Education 30:39 Bifurcation of Trustee Functions 33:26 Distribution Functions and Beneficiary Relations 36:52 Custodial Responsibilities in Trusteeship 40:19 Consequences of Poor Asset Management 46:41 Curriculum for Trustee Education 52:13 Opportunities in the Trust Industry Transcript of “THE TRUSTEE CRISIS: Navigating the Challenges” Frazer Rice (00:01.068)Welcome aboard, Jennifer. Jennifer Zelvin McCloskey (00:02.723)Thanks Frazer, how are you today? Frazer Rice (00:04.782)I am doing great. We’re going to dive into a topic that is near and dear to both of our hearts. And that is what I’m describing as the coming crisis in trusteeship, but I think it’s already here. Which is the concept of qualified trustees being in short supply, right in the face of a gigantic wealth transfer. And first of all, before we get into that, just describe what you do on a day to day basis first. Jennifer Zelvin McCloskey (00:33.445)Sure, I actually wear a bunch of hats. Day to day, right now, I’m a full-time practicing trust and estate attorney. I’m also an individual trustee for a variety of trusts that need either somebody here physically located in Delaware for a short period of time or even a successor trustee. But I’ve also spent many, many years building programs in trust management and trust administration. Because there is this crisis of human capital that just does not exist. I built multiple programs. They’re housed out of the University of Delaware. So I act as a trust and estate attorney, do planning, administration, I teach in the area, I build programs in the area, and I serve as a trustee. PEAK TRUST MANAGEMENT CERTIFICATE Frazer Rice (01:23.182)A full plate to be sure. To me, I came out of Wilmington Trust and another trust company served an individual trustee too. I’ve seen all these different flavors of trusteeship. My general sort of bon mot around that is that the individual trustees. I’d say 95 % or higher don’t really have an appreciation of the risk and responsibility that they’re taking on. And then the corporates have their own issues, which we’ll get into in a little bit. If we pull back even further, modern trust planning in wealth management, why is this so important? Jennifer Zelvin McCloskey (02:06.275)That’s massively important. It’s not just for the mass affluent or the ultra high net worth. It’s for everybody. We have all of these assets that we have this hyperfocus on building and increasing our wealth. Making sure that we have the ability to sustain ourselves throughout our entire lives. But if we don’t do this type of planning, if we don’t have structures and implementation for when we die, then our assets that we’ve planned so diligently for will fall off of a cliff. We lose the ability to control ultimately what happens to those assets. Layered on top of that, of course, is the tax component for ultra high net worth folks who are trying to really focus and direct their assets to make and create generational wealth transfers. Without this type of functionality and wealth planning and estate planning long-term, people lose control of what they’ve spent so much time building. Frazer Rice (03:13.338)One of the things I tell people as far as trusts are concerned is that, you know, we’re putting these structures together. They’re durable enough to withstand taxation or creditors or other asset protection features, create some guidelines around distributing the assets to the next generation or other constituencies. But also have some flexibility to be able to deal with the things we can’t look into the crystal ball and figure out over time. And that those three things just putting a document together that tries to do all that is hard enough, but then to put it in the hands of somebody or something to administer and to exercise discretion around it. That’s where the real art and science kind of stitched together and create this issue. You know, as we think about that too, the idea, the history of these types of scenarios kind of goes back to, you know, you’d put a structure in place and then you’d go hire a bank and they’d take care of everything. How do you look at that and say, all right, we’ve gone well past banks to individuals and then to dedicated institutions. What is the problem there? Jennifer Zelvin McCloskey (04:22.956)Now the problem, there’s two problems. In my opinion, what I see is that, you know, your individual trustee by and large is Uncle Joe, right? He’s the guy that everybody goes to in the family. The responsible one. He’s the smart one. The wealthy one who, great, doesn’t know what the fiduciary duties are. He doesn’t know that he has a duty of impartiality. He doesn’t know that… Frazer Rice (04:32.419)Right. Jennifer Zelvin McCloskey (04:48.475)He can’t self deal unless the instrument says so. Doesn’t understand how the instrument works. He doesn’t understand the nuance and the legalese written into the instrument. But he’s flying by the seat of his pants and everybody looks to him as the respected one in the family. No one knows that they have the ability to challenge him. So with your individual run of the mill trustee named in the instrument, they just don’t have the expertise, they don’t have the technical knowledge. Don’t know what they don’t know. They can get into trouble in that way. The other problem that you have with professional individual trustees oftentimes is that they are not formally trained. They may be an attorney who is working in that area, who’s doing plans for people who may or may not know what the full scope of being a trustee is. They may not realize, I have to get a special insurance policy because my malpractice insurance policy doesn’t actually cover this type of fiduciary engagement. There’s a lot of landmines that individuals can run into when they’re doing this type of work. On the corporate side, the problems that we run into is that there’s just a complete and utter lack. Frazer Rice (05:50.061)Hmm. Jennifer Zelvin McCloskey (06:12.059)Of available educational programs to teach people the proper way to be able to understand trusteeship. It has always been, and it just has developed over time through, you know, oh, we’ll give it to the bank, the bank will do it. This apprenticeship model, and that just does not scale well because if you learn improperly at the edge of a desk from somebody that learned improperly at the edge of the desk. Then the person that you’re teaching now at the edge of the desk is learning what you learned improperly. So anecdotally, I did karate for a long, long time. And the man who taught me karate, I’m almost a secondary black belt to like, was serious in karate. And the man who taught me karate said, you practice, it makes permanent. Don’t practice wrong. Because when you’re practicing wrong, you’re making permanent wrong things. And that’s what the apprenticeship model has the risk of lending itself to. It’s not that every trustee that learns at the edge of the desk learns wrong, but the risk is too high because the fiduciary responsibilities and the duties are too high to run that risk. The other problem is that we have a dwindling pool of really qualified senior trust officers because of just the nature of the job. You’re a human being, you’re an individual, you age, you retire. And it’s not something that pe

Frazer Rice and Bram Weinstein, the “Voice of the Washington Commanders,” discuss the shift in sports media for entrepreneurs. The current state of sports journalism is in flux, especially with the decline of the Washington Post’s sports section and its implications for local coverage. We explore the opportunities that come from this void. (Including the potential for new media ventures and the challenges of monetizing content in a fractured media landscape). The discussion also touches on the future of the Washington Commanders, the importance of audience engagement, and the evolving nature of podcasting and digital media. https://youtu.be/O0syDGcSkvU https://open.spotify.com/episode/3Ut9QRj7X9QD1pGEA6y6qt?si=39nLO2reQ8SK_nj0zenzDA Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Takeaways The Washington Post’s sports section closure is seen as a significant loss. There is a growing opportunity for new media companies to fill the coverage void. Monetizing media ventures requires innovative strategies and diverse revenue streams. Podcasters face challenges in gaining audience traction and monetization. The Commanders’ future depends on effective roster changes and health improvements. Engagement with the audience is crucial for media success. Digital platforms like YouTube provide exposure but limited revenue. The media landscape is rapidly changing, requiring adaptability. Local sports coverage is essential for community engagement. The importance of maintaining journalistic integrity in a changing media environment. SPORTS MEDIA FOR ENTREPRENEURS CHAPTERS 00:00 The State of Sports Journalism 02:59 Opportunities in Media 06:07 Monetizing Media Ventures 09:05 Navigating Podcasting Challenges 11:59 The Future of the Commanders 15:06 Engaging with the Audience DISCOVERING BRAM, THE COMMANDERS, AND AMPIRE MEDIA BRAM on SPOTIFY AMPIRE MEDIA ON YOUTUBE AMPIRE MEDIA WEBSITE Transcript of “SPORTS MEDIA FOR ENTREPRENEURS” Frazer Rice (00:00.686)Welcome aboard, Bram. Bram N Weinstein (00:02.551)Hey, Frazer, how are you? Frazer Rice (00:03.736)Doing great. The last time we spoke it was about three days before the Chicago Hail Mary, so I’m viewing that as good luck. That must have been something having to call that game. Bram N Weinstein (00:14.071)That was part of the most magical season I’ve ever been a part of. Not only first ever for the franchise, but 12 and five, NFC championship game, hadn’t done that in a generation. It was pretty incredible, yeah. Frazer Rice (00:28.652)No, as a skins fan, now commander’s fan, it’s been a long time, but it was a wild ride. One of the things that’s happened recently, which I know strikes near and dear to your heart, and frankly, for people who grew up sort of following it, has been, I guess, kind of the evisceration of the Washington Post sports section. And it’s got all sorts of impacts. But from your perspective, How do you make sense of that and what does it look like going forward for a city essentially that has all the major sports and the major paper not really covering it? Bram N Weinstein (01:09.719)I don’t make sense of it. I don’t understand it. I think at its core, The Washington Post is two things. It’s one of the most important publications in the world as the paper of record in the most powerful city in the world and the democratic center of the world. But it also is a local newspaper for one of the top 10 markets, top five markets in the country. And the idea that it would not cover its sports teams, or Metro desk, which, I know, you know, for our purposes, we focused a lot on the sports desk being shuttered. The Metro desk is too. So the Washington Post not covering the mayor’s office, city council meetings like in especially in these political times where, you know, the district budget is held by the federal government. To me, it doesn’t even it doesn’t compute that that wouldn’t exist. as far as like the sports section goes, which I think is like the lesser of the two real problems with this, but obviously is a real problem is, you I think for me, it feels like a death. I grew up reading the Washington Post. A lot of the reasons why I wanted to do what I wanted to do was through osmosis of reading Tony Kornheiser and Michael Wilbon and Tom Boswell and all of the great writers that came through the Washington Post. And I just don’t really understand how it’s not within the business model to be part of this. At the same time, you know, it does open opportunities for entrepreneurs like myself who have media companies and are always looking for new talent and always looking for openings. And I can tell you that void is going to get filled. But I do think it is sad that the Washington Post could not figure out a way to modernize itself to allow its coverage to continue for its loyal readership. This is a local paper that isn’t covering local news. That is astoundingly terrible in terms of a business practice to me. Frazer Rice (03:14.317)It’s weird because from my perch here in New York, I work across the street from the New York Times building and there’s a little bit of sort of guffawing that the New York Times has turned into a gaming company and sort of a media company second, which has helped to subsidize its continued commitment to long form journalism. But even then, I mean, it’s really focusing on arts and leisure and cookbooks and wordel and all sorts of things like that. And it’s a shame that the Washington Post either couldn’t pivot in that direction or otherwise make sense of things. Bram N Weinstein (03:48.727)Is the business model of media the same that was no. so there are a few things that play here to be fair. I’m not asking Jeff Bezos to lose money. You know, like, or just be the beneficiary to subsidize something, but you do bring up a point, which is. And I read this quote recently from, the old ownership group, the Graham family, who basically said. “You know, the newspaper is a grocery store. Like you are supposed to go in there and pick all the different things that you want. And hopefully there’s something for everybody or hopefully a number of things for everybody. And in modern times, the New York Times has done a very good job of putting together a new modern grocery store for people. So there’s a variety of different things that does subsidize the important work that it does. And in the end, like to me, the New York Times and the Washington Post and maybe the Wall Street Journal. Are the three most important newspaper entities, if you can call them that, in the United States of America. And for one of them to not understand their role in protecting democracy, in covering our world, in informing the readership, whether it’s locally or nationally, to me is an absconding responsibility. So I don’t know what the answer is. Again, I’m not like demanding Jeff Bezos just…money to keep things subsidized. Like it is a business and I understand that, but there must have been better ways to go about it or maybe, you know, sell it to someone who does have ideas because it’s important for its foundations to remain intact. And so I just, you know, for me, it’s, been hard to digest, honestly. And like to your original question of like, like, how do you make sense of it? I really don’t. I don’t make any sense of it. Frazer Rice (05:39.692)Well, you also now have a fledgling media company and I’m a devourer of yours and Kim’s and Standix podcasts and I learned something from it each time. I see an opportunity there if major component of the media establishment in the area is abdicating its role, not only to the major sports that aren’t getting covered as much. There’s an opportunity there. But even like the local hotbed sports like lacrosse, they’re completely ignored, I would imagine. And that might be a way to sort of get some grassroots component going. Bram N Weinstein (06:17.195)Yeah, we also here with my company Empire see the opportunity, unfortunately, but we do. And there’s a lot of talent that is available. There is a void in coverage. We know, you know, the size of our community, the appetite for sports. And so, you know, I don’t want to say too much, but we are actively seeking partners to expand in a pretty large way if possible. So Frazer Rice (06:24.045)Right. Bram N Weinstein (06:46.067)We’re working towards that and I’ve been working towards that and moving very fast in the hopes that we’re not the only ones thinking this like you. There’s a lot of people thinking there’s an opportunity here. I wish it wasn’t the opportunity that it is, but it has presented itself and it’s an opportunity that we intend to see through. So we are actively speaking to a number of different interested parties about funding a major expansion of what we’re doing. Frazer Rice (07:11.379)Really cool. Well, I’ll be sure to keep an eye on that as it develops. When you’re thinking about sort of the money making aspect of it, we don’t do things for free and it’d be lovely if we all had time and disposable income to do that without giving away the playbook because you’re raising money and you don’t want to give that up necessarily. But how do you think about that in terms of delivering value for sponsors or advertisers or the general audience? Have you made any…sort of commitment strategy-wise there. Bram N Weinstein (07:42.197)Yes, digital audio video forward. You know, I also believe in enterprise journalism. I also very much believe in long form journalism, but the audience appetite for it is limited. And so you do have to subsidize it. And that comes in the form of a number of different properties repurposed for different platforms in various ways, podcasts, video shows, YouTube. All offer opportunities to monetize the same content. I have been studying very closely the things the New York Times has done and thought about what kind of engagement tools would be necessary

This conversation delves into the intricacies of Qualified Small Business Stock (QSBS) and its significant tax benefits for founders. MICHAEL ARLEIN, Partner at Patterson Belknap, explains the eligibility criteria, the importance of strategic planning, and the potential pitfalls that can arise. The discussion also covers the implications of state taxes and the advantages of gifting strategies. We cover innovative approaches like the “GOAT” trust to maximize tax-free gains. Founders are encouraged to engage with legal experts early in their business journey to fully leverage QSBS opportunities. https://youtu.be/lfBt0j7BlW0?si=LufZ8j2YtgdspLMJ Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Takeaways from “QSBS For Founders” QSBS is a powerful tax benefit for founders.The maximum exclusion amount has increased to $15 million.Careful planning is essential to avoid QSBS pitfalls.Gifting QSBS stock can multiply tax exemptions.State tax implications vary; California does not recognize QSBS.Discounting shares can aid in estate planning.Converting from an S-Corp to a C-Corp can preserve QSBS benefits.Early engagement with legal counsel is crucial for founders.Innovative strategies like the GOAT trust can maximize benefits.Almost all businesses should consider QSBS eligibility. Chapters 00:00 Understanding QSBS: A Founder’s Guide.02:56 Navigating the QSBS Landscape: Common Pitfalls.06:07 Maximizing QSBS Benefits: Stacking Strategies.08:42 The Importance of Timing: Gifting and Valuation.12:03 State Tax Implications: The QSBS Challenge.14:52 Entity Structures and QSBS: What Founders Need to Know.17:37 Transitioning to C-Corp: Strategies for S-Corps and LLCs.20:29 Who Should Pay Attention to QSBS?23:44 Innovative Business Structures: Technology and QSBS-26:36 Early Stage Strategies: Cloning Yourself on the Cap Table- Transcript of “QSBS for Founders” Frazer Rice (00:01.109)Welcome aboard, Michael. Michael Arlein (00:03.096)Thank you. Good to be here. Frazer Rice (00:04.617)So let’s get started here. QSBS, Qualified Small Business Stock, is something that certainly all founders should be aware of. It’s a tax feature. It’s probably one of the nicest goodies that the federal government gives to people who are starting businesses. Take us through a little bit about what happens there. For founders, you’re going to hear the numbers 1202, which is the section that is quoted here. Take us through a little bit about what happens at QSBS and why it’s a powerful feature. Michael Arlein (00:37.496)Sure, that sounds good. To your point, the New York Times called QSBS a lavish tax dodge that is easily multiplied. And I happen to. I’m not aware of any other provision of the tax code that can save anyone as much money as QSBS. It’s really incredible. I think the policy reasons behind the provisions are that they’re designed to encourage entrepreneurship. Everyone on both sides of the political aisle is in favor of. The basic premise of it is that if you create a company.You own the stock for five years. The company’s in the form of a C corporation, It’s not in one of a series of restricted industries. Mainly service industries, that when you sell the stock, you can exclude from paying tax $10 million, the first $10 million of your gain. That’s the old rule, which I’m still dealing with, that that’s for stock that was issued before July 4th, 2025. And now QSBS has gotten even better. So if you get stock after that date. You hold it for actually now three years, you can exclude ultimately up to $15 million from tax. So we’re now dealing with two different regimes. I’m still stuck in the old regime. Most of the people I’m dealing with got their stock before last July. But I’ll try and point out the differences as we go along. Frazer Rice (02:29.066)Sure, as you said, there are a bunch of things you have to jump through. To make sure that you can sort of apply and then to further comply with the rules associated with it. Things like services. Making sure that maybe you don’t have too much cash and that it’s deployed correctly. Making sure that the original stock issuance persists throughout. What are some of the things that you tell your clients? How do you walk them through the process so that they don’t trip on themselves and lose this nice tax advantage? Michael Arlein (03:09.676)Yeah, there are some landmines, things that you can step on and blow it. There’s some weird rules around redemptions. Like if you have redemptions. Let’s say you create a company and then there’s three co-founders. Then very early on, one of the co-founders wants out or you want to kick them out. And then the mechanism for that is the company kind of buys back their stock. You know, there’s complicated rules that can, you know, blow up QSBS for the entire company. I think some people start their businesses as LLCs or S-Corps or things like that, and then later convert them. And that has to be done very, very carefully with good tax advice. Otherwise that can also blow things up. When I talk to founders, it’s pretty clear their business qualifies. They didn’t screw anything up. Frazer Rice (04:19.626)So the OBBBA in a sense turbocharged a little bit the tax savings. That five year requirement that you talked about. You can now get some of the benefits even as early as three years. And then the dollar amounts got expanded. In addition, and this was not necessarily OBBBA related. The ability to take one exemption and maybe multiply it via stacking continues to be a powerful tool. For those people who are walking into your office now. How do you get them when they sit down situated so that they do that planning upfront? Michael Arlein (05:08.598)Yeah, that’s, you we kind of buried the lead. The benefit of QSBS: it would be incredible if you could just pay no tax on 10 or $15 million. But what’s even more incredible is that you can stack or multiply the number of exemptions. You have using a provision of the code. It says that if you gift QSBS stock to some other person or entity. That that person or entity can take their own up to 10 or 15, their own QSBS exemption. I’m just gonna say it’s 15. We understand that’s for newly stocked. So, classic move for a founder would be to set up trusts for children. There’s a special kind of a trust for a spouse. You can do this with sometimes people make trust for their parents, their siblings. There are certain states where you can actually make a trust for yourself. Usually when people come to my office, the conversation is around creating entities. Typically trusts, and then gifting shares to those trusts. that As a family, you could go from 15 million tax free to 30 or 45 or 60 million tax free. The record I had one guy who had a very large family. He married, he had kids and was very close not only with his parents. With his siblings, his nieces, his nephews, even his aunts, uncles, and cousins. He created 23 trusts, which on paper at least would save up to $230 million. Wow. Yeah. Frazer Rice (07:08.896)There’s a danger with that though, with those 23 trusts had to be different. I imagine the IRS would say, wait a minute, we see what you’re doing. Stacking all of these different things is theoretically nice and all, but is there a way to create differences within those trusts so that the IRS doesn’t view them as one big pot? Michael Arlein (07:39.692)Yeah, great question. So you can’t create multiple identical trusts. Meaning I can’t create five trusts for my child. The IRS has rules that consider those trusts as one trust and would have only one exemptions. So, one of the limiting factors on creating trust is often, who are the people you’re willing to gift to? You know, so this guy with the 23, he actually was willing to create trust for his cousins, his aunts, uncles. Now, those individuals were the beneficiaries of the trusts, which means that they were eligible to receive money from the trust. But those trusts were designed so that when those people passed away, the money would circulate back to his children. So, you we never talked about it, but it’s possible that in his head, his plan was that he would maybe provide some benefit to his cousin. Maybe he’d say to his cousin, hey, if there’s $5 million in this trust and you need a little money, I’ll make some distributions to you, but I’m going to request that the trustee kind of withhold most of the money. And then when you die, it’ll come back and benefit my kids. So there are nuances there. But generally speaking, most people aren’t willing to do that. They’re not close enough with their cousins and their aunts and their uncles. So they end up maybe creating trusts, you know, for their kids, for their parents, sometimes, you know, for their spouse and maybe sometimes they go a little beyond that, but not that far. One thing that’s important is that the U.S. Frazer Rice (09:33.472)One thing that’s important is that the the QSBS is a capital gains tax Concept meaning you’re you’re saving on the tax. From a QSBS for Founders standpoint when the the founder sells the business, and you have to pay capital gains tax on that front. Part of the reason I’m skewing this toward founders is that there’s an gift in a state exemption of 15 million dollars. So it’s important to get these assets into these trusts as early as possible and with as low evaluation as possible. That in many ways is where the real leverage is. Does that square with your thinking? Michael Arlein (10:11.019)Yeah, absolutely. We have a permanent $15 million lifetime gifting limit. $30 million for spouses. And when you gift stock into these trusts, you’re typically gifting at a common stock valuation. People are familiar, founders are familiar with common stock valuations because they do that for purposes of issuing stock options, you know, the so-called 409A valuation. Now, a gift tax appraisal is different tha

Foreign Options for US Citizens Summary: https://www.youtube.com/watch?v=d-Jnr3Go2Gg Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) In this conversation, Frazer Rice of Next Vantage and Judi Galst of Henley and Partners discuss the increasing interest among U.S. citizens in exploring global mobility options amidst geopolitical chaos. We delve into the distinctions between residency and citizenship, the implications of U.S. taxation, and the motivations driving individuals to seek alternative living arrangements. The discussion also covers the potential for citizenship through ancestry, popular destinations for relocation, and investment opportunities in countries like New Zealand and Australia. Judi emphasizes the importance of understanding the legal and practical aspects of relocating, as well as the need for personal exploration before making significant decisions. Takeaways Interest in global mobility has surged among U.S. citizens. Many seek residency as an insurance policy rather than leaving the U.S. Understanding residency vs. citizenship is crucial for potential expatriates. Residency can lead to citizenship but often requires time and investment. Tax implications are complex; relocating should not be primarily for tax benefits. Ancestry can provide a pathway to citizenship in several countries. Popular destinations for U.S. citizens include Europe, the Caribbean, and New Zealand. Investment opportunities exist in countries like New Zealand and Australia. Emerging markets in South America and Asia are gaining attention. Practical steps include consulting experts and visiting potential countries. Chapters 00:00 Navigating Geopolitical Chaos: The Rise of Global Mobility 02:55 Understanding Residency vs. Citizenship: Key Differences 06:06 Tax Implications and Motivations for Seeking Alternatives 08:48 Exploring Ancestry-Based Citizenship: Opportunities and Challenges 11:54 Popular Destinations for U.S. Citizens: Europe, Caribbean, and Beyond 15:10 Investment Opportunities: New Zealand and Australia 17:59 Emerging Trends in South America and Asia 20:50 Practical Steps for U.S. Citizens Considering Relocation Transcript I’m Frazer Rice. We’re certainly living in crazy political times right now, and a lot of US citizens are worried about what’s happening here and abroad. And they’re starting to think about other residencies and citizenship options. I talked to Judy Gost at Henley and Partners about what is and isn’t possible on that front. By the end of this, you’re going to understand the locations that are interesting, the difference between residency and citizenship, and why that may matter as you make choices for your retirement and your location long-term, both for yourself and for your kids. Frazer Rice (00:00.874)Welcome aboard, Judy. Judi Galst (00:03.022)Thanks for having me. Frazer Rice (00:04.244)Well, we’re in the midst of a lot of geopolitical chaos, and I think you have seen and I’ve seen a lot of interest in United States citizens looking abroad for either places to live or other situations to either get away from the chaos or try to address some other needs in their lives. What is the state of the union? assume interest has ticked up. Judi Galst (00:27.874)Yes, I’ve seen more business than I could have ever predicted, but it’s not necessarily people that are leaving the United States. For the most part, most of the clients that I’m working with are doing it as an insurance policy. A lot of the conversations I have with a client start out with them saying, I don’t want to leave the United States, but I’m feeling unsettled and the way to mitigate the way that I’m feeling is to have options. So they want to understand what if I did want to have a guaranteed right to go live in another part of the world? What is available to me? How do I pursue this? How long will it take? Frazer Rice (01:08.434)And we’ll get into some of the technical aspects here, but one of the concepts is understanding the difference between being able to reside somewhere else and being a citizen of another country, and then how that interacts with being a citizen of the United States. Maybe take us through the comparison of residents versus citizenship. Judi Galst (01:28.748)Yeah, that’s actually a really important distinction. And it doesn’t mean that one is better than the other, but they do have different benefits. And so it’s important to understand the difference. So let’s start with residents. Residents doesn’t mean the ability to have a house in another country. It means the ability to reside legally in another country. So the US passport is very strong. You can go into a lot of different countries even without having a visa. But we can’t stay there forever. We have limits, for example, in Europe. We can go in for 90 days, but then we have to leave for 90 days before we can go back in for another 90 days. So if you become a legal resident of another country, you have the ability to live there unlimited for a certain period of time. Residency is not permanent unless there’s a path to permanent residency. So usually you’re going to have to renew it and there may be some conditions in order to maintain it. Now, how frequently you have to renew it is going to vary by the country. For example, in Greece, you can become a Greek resident via a golden visa and that is good for five years and you’ll renew for another five years. In Italy, it’s good for two years. Then you renew for another three years. In Portugal, it’s good for two years. Then you renew for another three years. And as I said, there could be conditions. So in Greece, you qualify via purchasing real estate. If you sell the real estate, you’re going to lose your golden visa, not be able to renew it. In Italy, you qualify via purchasing stock. Frazer Rice (02:51.925)Right. Judi Galst (02:55.945)If you sell the stock, you’re not going to be able to renew it. You can get some travel rights by being a resident. Usually this benefit is not as important to a U.S. person because we already have really good travel benefits with our U.S. passport. But it can often be a strategy for someone from a country with a weaker passport, say even someone living in the United States that has only a Chinese passport. If they want to go into Europe, they have to get a Schenken visa. So a strategy for them might be let me become a resident of say Greece and then I gain Schengen access. Not unlimited, but I get that 90 days out of 180 days. Finally, I would say that residency can have a path to citizenship. Usually it’s a pretty arduous path. For example, in Italy, you can become a resident. You have to live in the country of Italy for six months a year for 10 years before you’d be eligible to apply. In Greece, six months a year for seven years. But there is ultimately a path in most residency programs. Frazer Rice (03:56.755)So let’s dive into citizenship, which my predilection on that is that it’s a much more permanent component, but it’s also a much more difficult process in general. Judi Galst (04:05.646)It doesn’t necessarily have to be difficult. It really depends on what program you’re doing. But you’re right. It’s a guaranteed right. It’s very difficult for a country to take away someone’s citizenship. The other big difference is that you get a passport. So in addition to gaining the ability to live in the country that you’re a citizen of, you also get another travel document. So depending upon what treaties have been done between your country of citizenship and other countries, it may really improve your mobility. Again, U.S. passport is pretty strong. you’re U.S. passport holder, unless there’s something unexpected like a pandemic when borders close to Americans, you already have a good travel document. But it can be another mobility option. Perhaps you’re going into a country you don’t want to identify as a U.S. passport holder, or perhaps you have a weaker passport and you want to travel on a secondary citizenship passport that might improve your mobility. Where citizenship is particularly powerful is in Europe. Because if you become a citizen of one country in the European Union, you gain the right to reside and work in any country in Europe. Frazer Rice (05:11.104)And just to distinguish, how does that impact UK people after they Brexited? Judi Galst (05:16.942)Sadly, with Brexit, the UK is no longer part of the EU. So many people in the UK are quite upset about this because no, you’re not going to gain the ability as a citizen of an EU country to live in the UK, nor are citizens of the UK now able to live anywhere in the European Union as they were previously. Frazer Rice (05:36.992)So let’s apply this directly to US citizens. So US citizen taxed on worldwide wealth. Let’s start with that. sure because I just got a Twitter fight with somebody who said, well, if you’re crypto, you can move away and you’re not out of the system. I’m like, that’s just no. We’ll start with that. But taxed on worldwide wealth, good passport can travel, but there are limitations as far as how long you can stay in various countries, probably around Judi Galst (05:52.622)Mm-hmm. Frazer Rice (06:06.578)Investment options, land ownership, things like that, depending on it. Where are the benefits of that U.S. person looking for another place to either reside or gain citizenship? Judi Galst (06:20.312)Well, it’s not a tax benefit. You started out with taxes and I know when someone, a client calls and says, you know, can you tell me what my options are? I’m really sick of paying us taxes. I’m like, well, this isn’t the right call for you. Yeah. So, but it’s important to understand. It doesn’t mean you’re going to be double taxed because that is a misconception that many people have about whether they should pursue a strategy of alternative residents or citizenship, because unlike the U S and Eritrea, Frazer Rice

In this episode, 10 Family Office Myths exposed (and debunked). https://youtu.be/j1cgcZZcRBM Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Welcome back and Happy New Year on the Wealth Actually podcast. I’m Frazer Rice. We have a fun show today where we talk about 10 myths in the family office space. Mark Tepsich, who runs the family office governance practice at UBS is here as we dish into the ideas and concepts that are misunderstood in the family office world. Summary This conversation delves into the complexities and myths surrounding family offices, exploring their structure, governance, and the unique challenges they face in wealth management. The discussion highlights the importance of understanding the specific needs of families and the role of family offices in managing complexity and preserving wealth across generations. It also addresses common misconceptions about family offices, including their necessity, governance, and their relationship with institutional investors. Takeaways Family offices are established to manage complexity in wealth.Not all family offices are the same; each has unique needs.Governance frameworks are essential for effective family office management.Many family offices outsource functions rather than internalizing them.The myth that 85-90% of family offices shouldn’t exist is false.Shirt sleeves to shirt sleeves is a debated concept in wealth preservation.Family offices need to adapt to the evolving needs of families.Investment functions in family offices are often secondary to administrative roles.Family offices are driven by complexity rather than just size.The future of family offices may involve more direct investment opportunities. Chapters: Family Office Confidential 00:00 Understanding Family Offices: Myths and Realities02:02 The Complexity of Family Office Structures04:37 Debunking Common Myths About Family Offices06:17 The Role of Outsourcing in Family Offices07:54 Generational Wealth: The Shirt Sleeves Myth10:51 Flexibility vs. Permanence in Family Offices12:48 Governance and Decision-Making in Family Offices15:49 Investment Functions in Family Offices18:05 Size vs. Complexity in Family Offices20:09 Family Offices vs. Institutional Capital21:19 The Aspirational Nature of Family Offices23:30 The Relationship Between Family Offices and Institutions25:36 Technology in Family Offices: Current Trends29:03 Family Offices and Private Equity: A Comparative Analysis Myths 85-95% of FO’s should not exist vs. “there is no such thing as a family office’ Family office internalize everything A Family Office Anchored by an operating business is the same that is one funded solely by liquidity event Shirtsleeves to Shirtsleeves is myth Family offices are designed to be permanent’ Family Offices don’t need high end (almost SOX) like governance Family Offices are driven by net worth (no, by complexity) Family Offices are built on a robust investment function (no, it”s complexity management- often rooted in bookkeeping and accounting) Family Offices are like institutional Capital (no, many more motivations than pure returns- including whimsy and the knee-jerk ability to override the IPS) Family Offices are the right result for a career (they could be, but it is extremely unlikely- a lot of things have to be “just right” and there is little to know patience for development Family Offices make great wealth clients (very much depends on the function and the product- they can be difficult consumers) Family office tech is best – in – breed (No and it probably never will be) Family offices shun Large institutions (Surprisingly, no- needed for deals, expertise, and most importnatly financing and introductions) Keywords family offices, wealth management, governance, investment strategies, family dynamics, myths, financial planning, family wealth, complexity management, family governance Transcript: Family Office Myths Busted Frazer Rice (00:04.462): Welcome board, Mark. Mark Tepsich: Hey, Frazer, good to see you again. Appreciate the opportunity. Frazer Rice: Likewise. So let’s get started first. We’re going to go into some of the myths around family offices. But you really participate in kind of an interesting subset of that in terms of helping families design and govern them. What exactly does that mean on a day-to-day basis for you? Mark Tepsich: Yeah, good question. So, you know, it means a couple of things, right? So if you think about a family office, you have families that are at the inception point, right? Where things are getting too complex for them. They need to set up some sort of infrastructure. And it’s really like, what is a family office? What can it do for me? What are the pros, cons, and trade-offs? Where do I start? What’s the infrastructure, the systems? Who do I hire? How do I structure a compensation? So you’ve got families maybe coming at it. From post liquidity event, maybe coming at it from, we need to lift up, lift out this embedded family office out of the business to, hey, we’re an existing family office. We’ve got, you know, we’re evolving, right? The family’s growing, their enterprise is changing, the world around us is changing. People are leaving the family office, the next gen’s getting incorporated into the family office in some way. We’ve got some questions that could be, how do we engage the next generation through the family office? Mark Tepsich (01:21.614): How do we make decisions, communicate around our shared assets and resources, which could be a portfolio, maybe even a business, or hey, how do we come together and hire? What is this profile of this person look like? Who should we hire and not hire? What’s the structure of their compensation, carry co-investment, leverage co-investment? What’s the tech stack look like across accounting, consulting, reporting? Now, how do we insource and outsource? So it’s sort of. I like to call it organizational capabilities. So, you know, sometimes it’s soup to nuts, like starting from zero, other times it’s, we’ve been around for a long time, but we have a couple of questions. So that’s kind of my day to day. And, you know, I’ve been living this really since 2008 pre-global financial crisis. Frazer Rice So we’re going to go into, I think, some of the craziness of the family office ecosystem where we have people who wear many hats, people who wear masks, some people who are jokers and other people who are really good technicians and provide a lot of great insight. One of the things you were talking about is that the different types of mandate can be different. And I think maybe one of the first myths we should tackle is the The bromide that if you’ve seen one family office, you’ve seen one family office, which is thrown around at every family office conference and everybody chuckles for a minute and then it sort of washes away and no one cares anymore. What do you think about that statement? Mark Tespich (03:19.006): So I don’t necessarily think it’s true. And here’s what I mean. Let’s make an analogy to this, right? A business needs certain core infrastructure to just operate, right? And using accounting back office, you know the inflows, the outflows, you know, if you’re make a decision, these are the steps you have to go through. And so a family office, right? It needs to incorporate that, but it needs to incorporate it with the family and the family enterprise that is existing for that family, right? So, yeah, each family office is different because each family is different, but that’s like saying you’ve seen one business, you’ve seen one business, right? The strategy could be, the culture could be different, but, you still need some core operating infrastructure. And again, there’s accounting infrastructure, and that’s the basics, right? So there’s a curl of truth, but largely I think that it is false. Well, and at the same time, yes, families are different, but in general, families are trying to get to the same place, which is, know, they want to steward the wealth. They want to make sure it benefits the family and the other constituencies. And they want to make sure that it’s preserved over time. And those functions, you know, it’s very infrequent. You’d find the functions not there. And so how you get from A to B may be different, as you said, but there are a lot of universal truths to setting one of these things up. Frazer Rice So one of the other myths that we’ve come across is the idea that 80 to 90 percent of family offices shouldn’t exist. is, people and families set these up for, let’s call it the wrong reasons. Maybe it’s fear of missing out, maybe it’s great cocktail party chatter, maybe it’s an overdiagnosis of their needs. What do you think about that? Mark Tepsich Again, false. know, family offices are largely a function. They largely exist because there’s a market scale here. And what I mean by that is when you look under the hood at a family office, you’ve got basics of an accounting firm. You’ve got basics of an investment slash wealth management firm. You’ve got the basics of a legal slash tax firm. And then you’ve got essentially everything in between. And when you look at professional service firms out there, They can’t provide all of those under one roof, whether compliance or regulatory reasons. But the other reason is because no business model out there can really scale the complexity that each one of these families has. So yeah, you could outforce a lot of this stuff, but at the end of the day, family offices often exist because of a market failure. so, false, 85 to 90 % of family offices should exist. Frazer Rice (05:41.164) One of the other things, I’ve been around enough of these getting set up, is that the family office, if we get into sort of a technical structure, such that you set up a structure so that you’re able to deduct the expenses related to administering the wealth around

We have Mike Monaghan on the show today and covering the “Birth of an ETF.” He’s going to talk about the Founders ETF and its new launch. We’re also going to talk a little bit about what it takes to get an ETF up and running. From a compliance perspective, remember, there’s no guarantee of future performance. https://youtu.be/o-m3PYHKXqk?si=qBaHkJpUt7xgdpjG Transcript of “The Birth of an ETF” 00:00 The Founders ETF Frazer Rice (00:00.986)Welcome back, Mike. Michael Monaghan (00:02.616)Frazer, it’s great to be back. Frazer Rice (00:04.4)You are at an interesting point in time right now. You’re about to start up Founders ETF and I think you’re about to get trading authorization to get going. Maybe tell us a little bit about the process to set up an ETF. Then we’ll dive into the strategy a little bit. Michael (00:21.25)Yeah, absolutely right. We should start trading on the SIBO Thursday, so two days from now. And we’ve launched our first fund, the Founders 100, that owns the 100 best founder-led companies. I’d be happy to go through some of the process that it takes to set up an ETF. Frazer Rice (00:40.014)Love it. ETFs are the main way to go now in terms of getting an inveestment cvhicle up and running. What has your experience been around? The Popularity of the ETF Structure Michael (00:52.014)Yeah, so ETFs have become the primary investment vehicle for a few reasons. Let’s outline those reasons. Then we can go through some of the steps that it takes to set up an ETF. So on the advantage side of an ETF, they’re typically a bit lower cost than traditional mutual fund products. Importantly, they’re tax advantaged. So there’s no gains or losses that occur during the normal ETF growth phase. Everything that happens within the ETF is done with what’s called an authorized participant. So you do exchanges. And so there’s no capital gains that are assigned to the investors. As long as they hold the ETF, a tax trigger only occurs when they actually sell the ETF. Finally, it’s a great way to get exposure to the market. So whether you want to own a broad market index, one of the legacy indexes, or a vehicle like ours. That gives you in one single trade, rather than having to guess who’s going to win. Is Nvidia going to win or Palantir who’s going to win? You can own a hundred of the best winners in the market in one single stock ticker. In our case, FFF. Frazer Rice (02:07.364)So let’s dive into that theme a little bit. As you said, it’s the top hundred founder led companies. First and foremost, public I assume, private, you’re not diving in those waters. Public vs Private Michael (02:20.59)Correct. So these are the hundred best publicly traded founder led stocks. And we generally fish from the 200 largest founder led publicly traded stocks. So a lot of these are names and founders that are very well recognized. Whether it’s Elon at Tesla or a Mark at Metta, Larry at Oracle, Rich Fairbanks at Capital One. These are all very well known founders. They’re great entrepreneurs who are leading highly scalable, very high performing publicly traded stocks. 02:53 Understanding Founder-Led Companies Frazer Rice (02:53.914)So let’s define founder a little bit. Obviously we have sort of the cult of personality around high-end CEOs. It sounds like you’re identifying companies that have been founded. The people who are running them not only founded them, but they scaled them. They have now gotten them to a level of maturity. That’s different from the typical public company that we find in the S &P 500. Definition of Founder Michael (03:19.104)Yeah. So first let’s define a founder. Then let’s talk about why we think the founder led companies outperform a traditional S&P company. We define the founder as being a chief executive leader. It could be chief executive officer, could be chief technology officer. Sometimes that say a scientific or medical company, would be the chief scientific or chief medical officer. And that person conceived and founded the company, took it from zero to one. It’s their imprint that has guided it over its 10 or 20 or 30 year period. That’s taken it from a small private company to a venture backed company to a large publicly traded company. And so the idea being the person that founded it continues to run it to this day. We talk about the fact that we own an Nvidia that Jensen still runs. But we don’t own Intel. We own Meta because Mark still runs it, but we don’t own Google. We own Dell computer because Michael Dell still runs it. But we don’t own Apple. We own Capital One because Rich Fairbank still runs it, but we don’t own American Express. Investment Process Frazer Rice (04:25.86)Got it. So lots of things to get into here. How does it a company get on your radar screen? And then ultimately, how does it get off of it? Michael (04:35.806)Great question. the getting on the screen is fairly mechanical. We look at the 200 largest by market capitalization founder led stocks. So we look at all U.S. listed. So it could be listed on the New York Stock Exchange or NASDAQ, but it has to be U.S. listed. We then look at the 200 largest. And from there, we select the 100 best using a quantitative factor model. So I’m have a Sanford Bernstein background and so do some of the folks here. And so for folks who are familiar with Bernstein’s research, we use a Bernstein factor model to pick the best, the hundred best names out of the 200 largest. That’s how they get on our radar. And to get off is quite simple if they retire. So if a CEO announces he’s retiring, per the prospectus, we have 90 days to sell the stock. once we, so for example, Mr. Buffett recently stepped down from Berkshire Hathaway. And so we sell Berkshire Hathaway on his announcement and no longer own the stock. Frazer Rice (05:38.0)things like corporate mergers or divestitures or maybe even a reclassification of stock where the founder stays on in some capacity but their decision making has been reduced. How do you analyze that? 05:54 The Investment Strategy Behind the ETF Michael (05:54.326)Yeah, so there is some human overlay judgment calls here and the founder has to be an executive officer leading the company. So they can’t just run a division. They can’t just be chairman of the board. They have to be the executive in charge of running the company. Frazer Rice (06:14.0)And if for, I guess one of the exits possibly would be if, and I don’t know if this is even possible, but if NVIDIA were to take over Meta and there isn’t room for Jensen and Mark in the same suite, how do you analyze something like that? Michael (06:34.253)So in the business combinations where you have two founder-led companies or a non-founder-led company swallowed up by a founder-led company, as long as an original founder remains, it remains in the portfolio. So we’ve had some stocks that had, say, three to four co-founders. And as long as one of those co-founder remains, it remains in the portfolio. Voting Shares Frazer Rice (06:58.352)So one of the things that’s a bee in my bonnet is the concept of having shares where, in a sense, they’re super majority or voting components and then shareholders that have less decision making authority to act as a check and balance around the company. Is that something you’re not really that worried about or is it something that may be a factor that’s important later on? Michael (07:24.525)So we actually think that’s one of the opportunities that this exists. Like one of the things that we haven’t talked about yet is why is all this alpha there? Why is this uncaptured alpha there for us to go get? And we think historically in the past, active money managers have sometimes shied away from these founder led companies because to your point, Frazier, oftentimes the founder has managed to have super voting control, 10 to one shares, 101 shares. So they completely control the company. And some of these larger active money management complexes have said, well, we as the shareholder, we need to be able to have a vote and we’re going to underown these stocks. We have the opposite view. We think these founders are special. So we think that by the time a Mark or a Elon has driven their company into the public markets, they’ve showed that they know how to set the vision, ruthlessly execute and generate value for the shareholders. Concerns? And so we’re not concerned by super voting structures. Oftentimes those are the stocks that we want to own because it’s the founder that’s in control and setting the direction of the business and generating high returns for the shareholders. We view it as you either believe in them and you own the stock or you don’t believe in them and sell the stock. We’re not interested in other people’s getting on the board and monkeying with the decisions of the founders. Frazer Rice (08:30.255)Is this it? What is it about the founders, especially for those that go from zero to one, then to scale, and then to shepherding a mature business? What makes them better and what drives the alpha that you’re trying to seek? In terms of putting together a portfolio of these types of companies? 09:01 The Importance of Founders in Business Michael (09:02.891)Yeah, so the great ones tend to be a bit irreverent. They tend to be highly visionary. They tend to be charismatic communicators and relentless in their execution ability. They’ve got a great ability to pivot if a change needs to be made. And rthe moral authority to set a tone to generate very high rates of return. We see it sort of over and over and over in these founder led companies. And if you look at some of the studies that we’ve done. There’s a study that Bain Capital, Bain had done years ago in combination with Harvard Business Review, founder led companies tend to outperform non-founder led companies in say the S &P 500 by 3X. So it’s this personality type of high vision and high execution tends to drive outsize returns. And it’s a bit of a self-selecting process. What ma

BROOKE SUMMERHILL has written a new book to address “Divorce and the Wealthy Woman.” https://youtu.be/FFSeBg3XT8M In this conversation, Brooke discusses the complexities of divorce, particularly focusing on the financial aspects that wealthy women face. She emphasizes the importance of understanding one’s balance sheet, hiring the right professionals, and navigating complex assets during divorce. The discussion also covers the emotional components of divorce, the significance of having a supportive team, and the benefits of open conversations about finances, including the role of prenups. Takeaways from “DIVORCE FOR THE WEALTHY WOMAN” Divorce can be a daunting process, especially regarding finances. Understanding your balance sheet is crucial during divorce. Breathing and staying calm can help alleviate anxiety. Hiring the right professionals is essential for navigating divorce. Complex assets require specialized knowledge and support. Cash flow planning is vital for post-divorce stability. Parenting during divorce needs careful planning and support. Open conversations about finances can strengthen relationships. Prenups can facilitate healthy discussions about money. Divorce is a journey that can become easier with the right support. Chapters 00:00 Introduction to Divorce and Finances 02:58 Understanding the Balance Sheet 05:45 Navigating Complex Assets in Divorce 09:05 Building Your Professional Team 12:04 The Emotional Component of Divorce 15:09 Modeling Settlements and Cash Flow Planning 17:56 Parenting and Financial Responsibilities 20:41 Preventative Measures and Financial Awareness 23:53 The Role of Prenups in Marriage and Divorce Transcript of “DIVORCE FOR THE WEALTHY WOMAN” Frazer Rice (00:01.186) Welcome back, Brooke. Brooke Summerhill (00:03.378) Hi, thanks so much for having me. I’m so excited to be here. Let’s chat about the most fun topics in the world. Divorce and finances, right? Frazer Rice (00:09.952)Well, and codified in your new book, Divorce for the Wealthy Woman. I have already started, and I think it’s a winner for a bunch of reasons. The big one really is addressing a viewpoint that I think has been missed by the financial books generally speaking, Brooke Summerhill (00:15.794)Mm-hmm. Frazer Rice (00:31.086)It really corrects a problem, I think, around information asymmetry in finances generally. And unfortunately, we’ve both been around it from a divorce perspective. Tell me what, first of all, let’s let our listeners remind themselves of your practice. And what do you do there? And then what was the book trying to accomplish? https://www.amazon.com/Divorce-Wealthy-Women-costs-that-ebook/dp/B0G1ZMFVCN/ Brooke Summerhill (00:53.554)Okay, so hi, I’m Brooke Summerhill. I do specifically for the last like 15 years in finance. Specifcially in the last five specifically in divorce and finance for wealthy women. So I’m not very creative my book specifically and my podcast is literally called divorce for the wealthy woman. I love being able to understand the perspective of someone going through divorce,not feeling the fire, and creating a years long fight. I help alleviate the stress of divorce and go through the finances, the emotional aspect, I’m in financial psychology. I’ve been doing that and I plan on continuing doing that. It’s a fun, fun, fun career path for me. Frazer Rice (01:40.526)One of the great things I think about your book is it starts where I start. You really have to be comfortable with what your balance sheet looks like. Take us through a little bit about your experience in helping wealthy women get acquainted with something they weren’t familiar with initially. However, they have to get familiar with it real fast. Brooke Summerhill (02:03.014)So typically, you go to a lawyer . You’re about to get divorced and it was blindsided in your face. my god, what is going on? He wants to get divorced or she wants to get divorced. Doesn’t matter who you are, heterosexual couple or not. It does not matter. You might not know where the finances are, right? And you’re going to a lawyer. You expect them to help you out, but you don’t even know where the assets are. You don’t know it’s on the balance sheet. So the first step is breathing. Let’s not get into this sympathetic nervous system. No fight or flight, freeze, thaw, and let’s not go there if we can’t avoid it. And really just breathe and understand it’s going to be OK. That’s the first thing I want to just point out is you can do the work on yourself without having to do hard interval training. You can just breathe. So you’re going to breathe and understand, OK, the balance sheet. I can figure this out. You got it. And you might need to hire someone like myself who’s a certified divorce financial analyst, you might have your lawyer help you. You might ask your soon to be ex if they’re willing and amicable to understand the balance sheet. You might go to a financial advisor, wealth manager, your family office and ask some questions. So this is a time of learning and it’s okay that you don’t know where everything is. And the balance sheet is terrifying for most people. 98 % of us have money anxiety. It’s okay. Breathe. Get help and support where you can. The foundation is the balance sheet. If this is the only thing you take from today, is just breathe and know that the foundation is your budget, your expenses, what’s coming in, what’s going out. Can you figure that out? Even though you might not know where your assets are. Do you have Bitcoin? Or have different properties? Do you even know if there’s liens, mortgages, loans on them? That all will get figured out. But you’ve got to know what you’re spending. I would say, you tell me if you have a different experience. But most clients do not know their budget. And that’s OK. Doesn’t matter your wealth, income, anything. Most people, at least in America, do not know what they spend every month. So that’s the foundation is to start theirs. Understand, what are you spending? Just keep a little log. It can be old fashioned. And I have plenty of technological apps that can help with this. But keep it old fashioned. Just write down, what are you spending? And keep that for a week. Brooke Summerhill (04:28.752)That can help you in your divorce process and remember to breathe. There you go. Frazer Rice (04:32.91)And it’s part of my process, I think, is to just understand what you’re spending. And then the next step is really understand where it comes from to help support that spending. It’s like analyzing someone who earned 100 million dollars from this movie. It’s like, OK, that’s the headline. Now it’s a lot different in reality. Certainly taxes, how it’s paid to you. We’ll get into this in a second, and sometimes it’s not in cash. Sometimes it’s in different types of assets. Whether it’s stock or maybe you own homes, and it may not be necessarily liquid right up front. It sounds like we’re parking our cars in the same garage on that front. Brooke Summerhill (05:19.154)Absolutely, absolutely agree with you. Frazer Rice (05:22.114)So maybe let’s go through some of the complex assets that you think about that come up in any, not all divorce situations, but definitely in many of them. Many times people have grown their wealth through a private business. so even, you know, the number that is settled upon in the divorce settlement may not be readily available from a cash payout perspective. How do you take people through that? Brooke Summerhill (05:47.473)Oof. So I have an entire chapter on businesses because majority of my clients, I’m going to be very sexist here and say majority of my clients, husbands in a heterosexual relationship do own a business or have just been bought out of a business or are starting a startup or have something behind the scenes that they’re aware of or maybe not even aware of. So businesses are huge thing. That’s why I put a chunk of it in my book because The biggest advice I can give is hire, I’m going to be a repetitive throughout this whole podcast today is hire the right professionals if you can, because you don’t know what you don’t know and that’s okay. You’re going to breathe through that and acknowledge you don’t have to be an expert in divorce. But when you have a business reading, listening to podcasts, doing all of those exercises are wonderful and hiring an expert. So getting someone who’s understanding the finances in a divorce specifically, so business valuator, or just having a consultation. That’s enough to understand, this, I need a forensic accountant, because I don’t know anything that’s going on within this part of the businesses that I’m a part of, but I’m not really a part of, or I need a business valuator. Let’s just have a consultation. It could be really a non serious, non threatening, non emotional way to start it. I’m just going to have a consultation to understand, do I need this business valuator? I would just at least have those conversations to understand more about your husband’s business or your business in general on what are the numbers behind it? Because it is very complex, just as you’re saying. Businesses, absolutely, you want the right experts involved. Frazer Rice (07:30.506)And sort of as a broader business, or not really business, but sort of as a broader sort of contextual situation here, the type of wealth, whether it’s private funds, people who are invested in private equity or hedge funds or stock options or RSUs for people who are in the tech world, things that are held in trust, there’s the concept of carried interest and real estate and concentrated stock. This is to go back to your comment that there are people out there that can help you. Understand those assets, I guess for lack of better word, can and can’t do. As far as either provide cash flow or are easily divisible in a divorce settlement. Does that square with your thinking on that? Brooke Summerhill (08:13.522)Absolutely. And my role is to r

Wealthy families are discovering Tennessee’s legal and tax ecosystem as a key component for their long term wealth strategy. I spoke with ANDREA CHOMAKOS from Pendleton Square Trust on Tennessee around these advantages that the Tennessee Wealth Ecosystem provides in the context of other states’ legal systems and economies. We cover directed trusts and Tennessee situs, and even a tip like the Community Property Trust, which is interesting in both prenuptial tax planning and estate planning contexts. https://youtu.be/CiR8eoAG-iI “The Tennessee Wealth Ecosystem” Transcript Frazer Rice (00:00.814)Welcome aboard, Andrea. Andrea Chomakos (00:03.128)Thanks, Frazer, happy to be here. Frazer Rice (00:04.696)Well, glad to have you on. Always happy to talk to friends of mine at Pendleton, talk about Tennessee and trust administration generally. Our listeners are probably pretty well versed as far as the idea of trusts, but I don’t think it hurts to go and talk a little bit about what the trustee function normally entails as we talk about what is interesting about Tennessee and other jurisdictional issues. Andrea Chomakos (00:29.358)Absolutely. So Frazer, it’s great to be here and share some conversation with you and your audience. While I have been in the professional fiduciary role for several years, for several decades before that, I was a practicing attorney. So I would often have conversations with my clients and drafting their documents and asking them decisions about who to appoint as a trustee. One of the very first conversations we would have is what does it mean to be a trustee? As I have now come over to the other side, broadly stating that the trustee has the responsibility to administer the trust for the sole benefit of the named trust beneficiaries in accordance with the trust terms. That seems like a lot of really big words that don’t make a lot of sense to the average person. I get it. When I was practicing, a lot of my clients, their reaction would be, okay, so you’re just telling me that this person is the person who makes the decisions about distributions and that’s great. I can go, you know, no big deal. And the reality is, yeah, the reality is it is a big deal. Because it’s more than just making distribution decisions or making them in a vacuum. You have to look at the broader picture. Frazer Rice (01:41.228)It’s more than that though. Andrea Chomakos (01:55.598)But it also entails managing the trust assets and investments. It means making those important distribution decisions and understanding the impacts those are going to have not just in the short term but the long term. Filing and paying tax returns for the trust. Communicating with trust beneficiaries, providing reports and accounts. And even all of that sometimes seems like not that big of a laundry list but Let me give like an example that I ran into. Everybody loves a good example. So when I say a trustee is responsible for investing and managing all of the assets of the trust, that also means the protection and preservation of those assets. And it’s incredibly common to see a trust hold some real estate, oftentimes a residence that a trustee or a beneficiary lives in. Frazer Rice (02:24.58)That’d be great. Andrea Chomakos (02:51.094)And you may say, OK, well, no big deal. Like if something happens, we’ll just get it fixed. Well, it’s more than that, right? You need to really understand what that means and the risks you’re taking and the potential liability you’re taking if you don’t manage those issues in a way maybe different than you would if it was just your own house. So I was at a prior institution and that institution was serving as co-trustee with a beneficiary who resided in some trust-owned property. And lo and behold, you know, got a call from that beneficiary saying, hey, there was a leak with one of the pipes in the house. So I just went out and got some duct tape and put that around the pipe to stave off the leak, but now it’s gotten really bad. And you’re just sort of like, well, wait a minute. Like that’s. Frazer Rice (03:34.276)Hmm. Andrea Chomakos (03:47.573)As a trustee, that’s not an appropriate response to fixing a leak, it’s not a roll of duct tape. So it’s things like that that trustees are responsible for. Frazer Rice (04:00.004)One of the things too that’s happened in modern legislation is that those three functions you talked about, the investment, the distribution, and the administration have been in many states you’re able to, we like to call it bifurcate them, so that you can put an expert maybe in the investment role, maybe a family member with a corporate trustee in the distribution role, and then a corporate trustee in the administration role who, you know, they’re used to doing the paperwork and the tax filings and the eye dotting and T-crossing. And in your, I guess in your experiences, we’ve gone through that. How have trust companies evolved to take into account this new flexibility? Andrea Chomakos (04:42.254)Absolutely, think you hit the right word. I always say the same thing, Frazier. It’s a bifurcation of those duties and responsibilities. And so there are more trust companies who are embracing what we call the Directed Trust Model, where the corporate trustee is handling the administrative functions. So the reporting, the trust beneficiary communications, filing the tax returns, all of those very important functions, but ones that oftentimes are overlooked, their importance is overlooked. And other people are given the role of either distribution advisor, and sometimes the corporate trustees in these roles will make distribution decisions. But certainly the investment function is one. And as you see arise in individuals, families, using private equity for investments, other alternative investments, you see them using RIAs, multifamily offices, to manage their investments that, and those entities don’t have that trustee function. There are more corporate trustees who are filling that role. And I think that we’re only going to see that market increase and that demand increase. Frazer Rice (06:11.196)I don’t think I could agree more with that statement. I think the idea of people having all of those functions under one umbrella really ignores just the way wealth is being managed these days, whether it’s sort of peculiar assets or even, you know, regular run of the mill stocks and bonds, people have their advisors and they don’t want to necessarily give that up to take advantage of trust situs and professional trustee services. Andrea Chomakos (06:21.998)Listen. Frazer Rice (06:36.524)As I talk to people around this topic, the culture of a good trustee, and especially sort of a good corporate or a good administrative trustee, there are a lot of things that go into that. In your experience, what is it that makes a good sort of corporate or administrative trustee for particular family? Andrea Chomakos (07:01.422)There’s I mean, that’s a great question. And it should be top of mind for all clients. Right. I think there’s a couple of things. One is the institutional professionalism that a corporate trustee, independent corporate trustee provides, as well as the skill, the background and then the lack of conflict of interest. So when you think about an administrative trustee that’s not managing the investments, we have no dog in that fight as they say about what’s going on with the investments, how they’re being managed, how they’re being allocated. We, Pendleton Square and others are here to serve the beneficiaries, to facilitate communication, to help beneficiary wealth education, to continue the continuum of family values and conversations, as well as be some be a person who can sit there alongside them and educate them about the trust, about the wealth, about the impact the distributions from the trust are having on their own estate, on their own lifestyle, and really honing in on the things that they’re really good at. And I think predominantly it is that being free of conflict. We don’t have any other interest in the trust. Frazer Rice (08:28.252)I think the concept of staying in your lane is important. I think in the old world where the big trust companies did everything and they would allocate resources to that because doing everything required good integration and so on, it made a lot of sense. But nowadays, as we talked about the bifurcation just now, the provision of the administrative trustee functions and the distribution committees, et cetera, that feels more like an accommodation. Andrea Chomakos (08:30.913)I’m sorry. Frazer Rice (08:56.696)than a sort of focus for them. And so these trust companies that have developed, the new ones that are less worried about the investment function, that that focus is now a strength in the sense that people hire experts in that field in order to get what they need from an estate planning perspective or a site of choice, et cetera, but then to really effectuate that culture we just talked about. Andrea Chomakos (09:26.956)Yeah, I mean, think there’s a couple of nuances there that you touch on that always resonate with me. And so one is. Trust business, it’s a business, we all have to admit that it’s a business, but is it relational or is it transactional? And at its core it’s really relational. You’re working alongside a family for hopefully multiple generations and as an institution you can carry forward that historic bank of knowledge in the grantor’s intent, the family values as you’re administering the trust. But in many larger institutions, because of just structural considerations and constraints, sometimes you have a lot of turnover in personnel. You have some loss of historic knowledge and information. And you have a compression of what it takes. not just the skills, but the technology and what it takes to execute on trust to meet the needs of the beneficiaries. And so sometimes those decisions get kind of kicked down the road to a committee that

Musician and label owner, Blake Morgan, discusses the Music Business and the importance of “Reputation over Fame.” Ever wondered how musicians really make money? It’s a tough journey filled with losses and small wins, but it’s all about persistence! In this episode, Blake Morgan shares that every small gamble counts, and eventually, one big win can turn it all around.: “The people who are “for real” have no choice.” https://youtu.be/j8vf5dI-cbE Transcript Frazer Rice (00:01.135)Welcome aboard, Blake. Blake Morgan (00:02.946)Good to be here. Frazer Rice (00:04.111)Well, it’s really nice for you to be here. You were nice enough to invite me to your show, your residency downtown. And I was glad to reconnect and remind myself how talented A, that you are and B, that musicians are. And it got me thinking about business and how musicians and the world of music works these days. So it’s a treat to have you on there. Blake Morgan (00:27.714)Thanks so much. I’m glad you could make it to the show and it’s great to talk to you again. Frazer Rice (00:32.155)So let’s start at the beginning. So if you’re a musician, you’ve been bitten by the bug, you’re talented, and you get that wonderful curse, what are the ways that musicians really make money and support themselves? I imagine it goes from a spectrum of busking and performing and having your guitar case open and taking… donations from there on up to the professional musician and then to the actual creator of the music itself. How do you think about that? Blake Morgan (01:01.858)Right. So, you know, I think I’m thinking about your audience and finance people and business people, you know, right off the bat, of course, for starters, the marriage between commerce and art has always been, shall we say, an interesting one, or it’s been it’s been a conflicted one. And it’s mostly been conflicted for the artists. But the reality is, you know, I think Frazer Rice (01:22.747)Sure. Blake Morgan (01:32.897)in a lot of ways and I do have something of an eagle eye view because I’m an artist, I’m a songwriter, I’m a record producer and I’m a record label owner. And so whether you’ve had a career and are having one like I am or like the person that you’re imagining who’s just getting, who’s just starting out, I think your experience basically it’s very similar to quantitative finance. in that you’re acquiring a lot of small bets that rarely pay off, but when one does, they make up for all the other losses. And every part of being a musician is very much that experience. So when you’re first starting out, whatever that means, if you’re making, if you’re building tracks on your laptop, if you’re, you know, I think the days of busking on the street are, probably behind us because I don’t see it very much, honestly, in New York. And we can talk about why we don’t see it very much later. But the reality is however you’re getting into it, you’re immediately in a position where you know you’re going to be taking a loss. And what you’re hoping is that there will be a payoff at some point so great that it will pay for all or most or some of your losses that you’ve Frazer Rice (02:30.203)Right. Blake Morgan (02:58.414)crude. And the truth is that really never ends. And I think that that really also kind of never ends if you’re a superstar. That’s really that’s that’s that’s the gig. I don’t see I don’t see billionaire investors usually sort of hang up their investment coat jacket. I don’t know what it is, but I don’t see them hang up their cape and say, I’m out. You know, they’re still trying to somehow leverage what they have into something else. Frazer Rice (03:20.279)Bye. Blake Morgan (03:27.822)And so that’s the financial part of it, which is that, you know, I think especially now, if you were talking about the beautiful curse, like I think especially now there is this feeling in music that musicians make music, you know, for fun. And I’ve never, I’m not a musician who makes music for fun. I’ve never met a musician who makes music for fun. We make music because we’re compelled to. That’s the beautiful curse. It’s not because, hey, I’ve got I’m thinking about doing this and it’s just the people who are for real have no choice. And so I often say that my relationship to making music, and this was true when I was a kid, when I was just starting, my relationship to making music is exactly like my relationship to breathing, which is that I really like doing it. But if I didn’t, it wouldn’t matter because I’d still have to do it to be alive. It’s a part of who I am, right? Frazer Rice (04:21.403)Sure. Blake Morgan (04:23.894)And the thing about breathing is we aren’t in a position to being like, how’s the breathing industry? How am going to leverage my breathing into some sort of better form of breathing that would keep the lights on? We’re all doing that, I guess, with our lives in some form. But that’s that awkward marriage of commerce and art, which is that our strength as artists, as musicians, comes from the fact that we have an absolute bedrock. We are compelled, a bedrock need. to continue to make music no matter what, no matter what’s thrown at us. And then that’s also exploited because the people who exploit us know that we’re still gonna do it no matter what, in whatever form that takes. So that was like 20 pounds of answer to a one ounce question. But that’s the real truth, which is I think if you’re starting out, you really are hoping that you’re gonna you’re gonna start trying things basically to get some kind of a career off the ground, some kind of path forward to be able to make more music, some path forward where you’re gonna be able to make music where you wouldn’t want to have to do something outside of your own profession. People don’t tend to set out to be in a profession with the overwhelming feeling like they’re gonna have another profession that they’re gonna have to have to pay for their bills for their actual profession. Frazer Rice (05:52.611)No question. How do you graduate from hobby to commitment in many ways? Blake Morgan (05:53.39)So. Blake Morgan (05:58.734)Exactly, exactly. And so right out of the gate, you’re hoping that your ideas and your talent and your perspiration and your inspiration are going to be enough to leverage the next moment and the next moment and the next moment. Moments where you know, and you know, a 13 year old who’s trying to write their first song or pick up a violin and practice, they know that they’re going to lose and lose and lose. and lose and they’re hoping that somewhere down the line they win and that pays for these losses and this is financial a financial truth and an emotional truth to like I’ve taken I often say to people like I’m a good humored person generally speaking but like I’m 96 % scar tissue at this point and so I still the joy offsets the scar tissue right I don’t want to be bitter and and and I’m and I’m not but Frazer Rice (06:47.62)you Blake Morgan (06:56.969)The moments of artistic wonder and satisfaction, just like the moments of financial hope, like, my God, this actually is hitting or this actually works. This really gets the monkey off my back to be able to do more of this, right? It’s very, very much the same, whether it’s financial, emotional, or temporal. The time you’ve put in to try to do something pays off when it works. Frazer Rice (07:26.731)So this massive investment, time, emotion, skill, dollars, et cetera, what are the ways that you start to get into the green and turn it into a situation where you’re actually sort of making money on what you love here? Blake Morgan (07:47.832)So if there was an easy answer to that, I would hope that you would have it and you could teach me what it was, but there’s a complicated answer to it. And it’s harder than ever. Art and music are devalued more than ever. The rungs under the ladder of where I’ve been able to get in my career have been kicked out. It’s harder for people to get to where I am. The world has changed because of piracy and streaming and Frazer Rice (07:52.89)Right. Blake Morgan (08:16.043)now AI and you know, we can touch on all of these things. But I do think that there’s an important panacea that will lift every facet of this. And in a world where we’re seemingly fixated on followers and likes and streams and these kinds of numbers, the reality is the place that I get paid As a label owner, as a record producer, as an artist, as a singer, as a guitar player, as a bass player, as a piano player, all the jobs I have, the place that I get paid is that I have a reputation. And we live in a fame-obsessed business, music, and a fame-obsessed culture, but reputation and fame are not the same thing. And… When you’re in, for lack of a better way to describe it, when you’re living in sort of in a Mad Max world, the music world has turned into this kind of wasteland in a lot of ways, unfortunately. When you can prove that you know where the fresh water is and you have some fuel for your car, you know how to evade the raiders on the highway, when you actually have a reputation. Frazer Rice (09:28.603)You Blake Morgan (09:35.278)there’s any numbers of ways that that winds up being valuable. And that could be a reputation of just being an incredibly professional singer who on short notice can go and sing a national anthem. That can be a reputation to say, we’ve been trying to make this record for months. We can’t get out of our own way. We’re screwed. We need someone who actually is from the before times who knows how to make a freaking record as opposed to just generating one. Right? Frazer Rice (09:48.581)Mm-hmm. Blake Morgan (10:04.683)Why would you go to a doctor? You’d go to a doctor because you need something. You can’t do it yourself. Home dentistry, bad idea. Home lobotomy, bad idea. And then you’re going to say, well, which one of these doctors has a reputation that I could trust to put this part of my life in their hands, right? So I think that’s

Family Office Security with EDWARD MARSHALL, CEO of PRESAGE GLOBAL https://youtu.be/uLbbZg52ABg In this conversation, Frazer Rice and Edward Marshall delve into the complexities of security within family offices, emphasizing the importance of understanding risk as a multifaceted concept. They discuss the vulnerabilities unique to family offices, the interconnected nature of various risks, and the necessity of a comprehensive approach to security that encompasses governance, internal threats, and physical safety. The dialogue highlights the need for families to engage with security experts who prioritize diagnosis over fear-based marketing, ultimately aiming to enhance the quality of life for families through effective risk management. Transcript Frazer Rice (00:01.173)Welcome aboard, Eddie. Edward Marshall (00:03.074)Hey Fraser, how are you? Frazer Rice (00:04.375)Great. Thanks. You are now a member of the two episode club. We’ve got a few of them out there. We one of my favorite ones was with you talking about there is no such thing as the family office, which I thought was a terrific bromide that I bring out every once in a while. It can be controversial depending on who you’re talking to. Edward Marshall (00:23.15)So some people like that and some people hate when I say that, but it’s all good. I mean, it speaks to the whole issues around family offices and I think some of the things that we’ll probably talk about today around security is if you’re defining it so many different ways, we’ve to look at it more as a process than some actual thing that we can put our finger up. Frazer Rice (00:46.421)Well, so security and whether it’s family office or regular high net worth or people generally is foremost in the headlines these days. We had the United Health Care executive who got shot. We’ve got different scenarios of global conflict out there. The theft around financial assets is everywhere. The urgency in the family office space, though, it seems like it’s really taken on a new thing. What is your experience with it? Edward Marshall (01:17.612)Well, mean, I think we could take a look at it from the perspective and start out with this, is risk is really what we deem it and how families and companies… offices and investors are looking at risk, they can perceive it in a lot of different ways. But I think one of the things that are important for high net-worth individuals or family offices is that some parts of their just organizational DNA create these engineered vulnerabilities. So what they are makes them more susceptible. And if you think of it just from the Willie Sutton effect, right? Why do you rob banks? Because that’s where the money is. It’s kind of myopic. Because you have to look at the other factors. What does the family office typically have as characteristics? You tend to have a very lean operation. There tend to be sources of time, line, agnostic capital. They have a lot of trusted relationships. Their customer is the family. And they’re pretty agile. So a lot of those factors come together and make them attractive for bad actors in a lot of different aspects. They could also be politically outspoken, which attracts a different kind of attention to them. And so it is… It’s really an ability to understand the nature of family offices and what makes them attractive for them because they have enterprise level wealth and oftentimes amateur or retail level security and risk management practices and processes in place. Frazer Rice (03:08.009)So how do you get your arms around it? When I hear risk, think, my gosh, you’ve got physical risk, you’ve got technological risk, you’ve got all sorts of other things. One of the frameworks you have is really these 10 domains of risk. And we may not list all 10, but how do you get your arms around it when you’re helping a client think through what their vulnerabilities are? Edward Marshall (03:30.873)Yeah, think the 10 domains of risk that we have put together as kind of an organizational philosophy for Presage Global really harkens to the fact that traditional security, traditional risk management is very siloed. I’ve got my cybersecurity thing that I’m focused on, then I’m focusing on physical security. Unfortunately, risks and threats don’t really respect your self-constructed silos. And that old school mentality tends to lead to lot of whack-a-mole behavior and reactive behavior to these types of risks that come out. So we came up with this framework. The risks range from privacy, technological, reputational, legal, operational, financial, and so forth. And the reason we came up with that is that we were seeing the interconnected nature of risks in this space, whether it’s for family offices, companies, or investors. there’s a lot of interconnectivity between these risks and they can cascade. So something that starts out as a privacy risk, exposed information, a bad tweet, an Instagram post that puts out some information around you can lead, cascade into reputational issues or financial… fraud types of issues or even legal fights depending on kind of the situation that’s there. And if you’re not looking at risk across these different domains, how they interact and really taking a deep dive to assess it, you don’t look at the entire picture. And I think that combined with not just focusing on the shiny object of a technology driven Edward Marshall (05:31.617)approach to solving risk in these issues is important as well. Oftentimes you’ll see folks that work in the security space or people that have purchased something to support them on security or risk management. They’ll say, you know what, we’re doing great because we have X, X software, X tool or whatever it may be. But they haven’t even evaluated if they even need X tool that’s out there or even if X tool is properly configured so you could be spending thousands of dollars hundreds of thousands of dollars or millions of dollars if you’re a company on these tools, but if they’re not properly configured then all that money is for nothing and it’s and And it becomes like security jewelry. We’ve got all this stuff that’s in place. We have cameras that are of X brand and they’re doing all these things. We have firewall that is of Y brand and it’s doing all these things. But if you haven’t properly configured it or the people that are supporting you internally and externally… some of the externally creating supply chain risk there, then it’s all for naught. it comes down, and it’s similar in the work that you do. If you’re not looking at somebody’s entire trust and estate picture just beyond the documents that they’re trying to draft, how do you figure things out? It has to be not just a black and white, here’s a legal document for your trust and estate. It’s part… archaeology, part anthropology, part psychology, multiple other science disciplines and other disciplines that come into it to develop a document, to develop a plan, to have an execution that actually keeps the family safe. Frazer Rice (07:30.315)So when, part of this seems like a real governance issue at the family level or at the family office level. When you see it done well, who owns this task, the security task at the family level? Because I could imagine the Generation One, the matriarch or patriarch, they wanna deal with it, but I’m not sure they’re the best ones to be driving it. What is a good practice there? Edward Marshall (07:58.189)Well, listen, think risk management and security, oftentimes, whether you’re talking about a Fortune 100 company or a family office, is looked upon as a cost center. And I think that’s an unfortunate aspect to it, instead of an enablement factor for you to go and do the things that you want, right? Good security, good risk management for a family should enable the quality and improve the quality of life for that family. If you’re constantly thinking of it, we have to spend X amount of dollars on our cybersecurity or planning for our travel or purchasing this trying to reduce my privacy footprint by buying some security tool that does that and says that I’ll get all of your information off the web news flash. Not possible. You know, there’s thousands of data brokers that are in this country. There’s legislation that is going on in different states and at the national level to try to limit the aspects of the data broker stuff. But you know what? At the end of the day… Edward Marshall (09:14.178)that information is out there to nation states and to bad actors and try telling a hostile foreign country or a hostile hacker whether they’re in Brooklyn or Belarus to remove your private information from their data sources. It’s not going to happen. you have to, putting it in the perspective of governance is shifting the mindset away from Frazer Rice (09:31.318)Right. Edward Marshall (09:41.467)Just being a cost center and to how does this help? All of the family office operations that are there and the family improve their quality of life by keeping them more secure. And that’s a critical step to it. Then having a robust plan and really looking at the plan and testing it. This may say simple, but if you’re not, if you don’t have a plan and you’re just trying to patch things together and you’re not testing that plan, then you’re spending a lot of time and not of getting a lot of good results. If you’re not thinking of security governance and risk management governance through a maturity model, understanding what good looks like, where we are today, where we want to go into the future, here’s my gaps, here’s the things that a good family office that’s focused on this issue or a good company that’s focused on this issue looks like, then I think you’re missing out on a lot of things for these families to really keep them You gotta be able to fix those gaps and somebody has to own that mandate within the family and not be looking at it as, well we didn’t have any incidents this year as a metric. That’s too simple of a

RICHARD HAASS returns to the podcast to talk about the US FOREIGN POLICY implications of Trump’s Tariffs and other initiatives. We take another tour of the world’s hotspots after the recent UN conference here in New York. Finally, we weave in an analogy of the recent crowd misbehavior at the Ryder Cup as a symptom of America’s current mood. https://youtu.be/z4FlnrXl8tE US FOREIGN POLICY: INTRO Frazer Rice (00:01.277) Welcome aboard, Richard. We are past our technology glitch, I think. The next big thing here is to try to figure out what the US looks like. We’re on the heels of the UN week and also the Ryder Cup. I’m not sure which one was more chaotic, but as you look at the US’s standing after the UN, what do you take from the events that took place last week? Richard Haass (00:02.744) on US FOREIGN POLICY Great to be back. THE US MOOD (AND THE RYDER CUP) Richard Haass (00:28.172) It was not a great week for what Joe and I, may he rest in peace, called soft power. What happened at Beth Page, the terrible manners, the coarseness, vulgarity, choose your word, the lack of sportsmanship, we could go on, but you get the point, was really poorly received in Europe, as it should have been. And I thought the PGA here just showed a blind spot would be generous. So it was not good. I felt somewhat between embarrassed and ashamed and also just overshadowed some unbelievable golf on both sides. Frazer Rice (01:11.069)Kind of where I came out on it. And it just felt bad watching some really good players doing their thing and then all of a sudden, again, overshadowed by pretty boorish behavior. Richard Haass (01:22.51) Particularly golf, because golf’s a game of rules and norms. I think it was Rory Mclroy who used the word etiquette, and what we saw was anything but. I really wondered at times whether some of those people ever played golf. And then the UN. Look, it didn’t happen in isolation. The President’s US Foreign Policy speech was…at times just, it was seen, it was taken badly by Europeans. It was for understandable reasons, seen by them as something of an attack on them. The comments like about Sharia law in London were over the top. The criticism of immigration policy, some of which, for the record, deserve some criticism, I would say. The total denial of climate change was badly received. So it was not good, even though, and I think the president detracted for some of his legitimate criticisms of the UN. My own sense, though, is the UN’s got bigger problems than Donald Trump’s speech. The UN has basically made itself increasingly irrelevant. It’s no longer a place for serious diplomacy. At most, it’s a venue for side meetings. And since then, you’ve had the announcement of a “peace” plan for Gaza and so forth. So the world’s moved on. quite honestly, what matters is not what happened during a few days of traffic in New York, but rather what happens more broadly. So we’ll see what, if anything, comes of this Middle East announcement. We’ll see what happens next, if anything, diplomatically with Ukraine. President Trump’s about to meet his Chinese counterpart in less than a month in South Korea. So there’s a lot going on. And not to mention domestically, there’s a lot going on we can discuss. So the fact that the Ryder Cup or the UN were not great in and of themselves, they’re more data points. And I think what matters is more the larger story for better and for worse. US Foreign Policy: Russia and the Ukraine Frazer Rice (03:32.339)As we just a couple of quick points to hit back on Ukraine Russia. What’s the state of play in there right now? Richard Haass (03:41.71) Well, we’re reaching the end of what you might call the third fighting season of this phase of the war, the one that started just over, mean, just under three years ago, in February of 22, if I have my dates right. My sense is things will dial down militarily somewhat during the winter, and then they’ll dial up again early next year for a fourth fighting season. I don’t believe diplomacy will gain traction until the United States does probably two things, puts much more economic pressure on Russia and gives Ukraine much more military wherewithal, both to withstand Russia and to take the war to Russia. Ultimately, diplomacy will only happen in a context where Vladimir Putin comes to the conclusion, however reluctantly, that time is not on his side. Right now, he believes time is on his side. He has no reason to compromise or settle. Only if we convince him. The time is not his friend, I believe. Will he agree to something like a ceasefire? I don’t think we should be pushing for peace for any number of reasons. We can go into it if you want, but I don’t think we need to. So at the moment, diplomacy is dependent on the calculations of the two sides, and I think the Ukrainian leadership is willing to accept a ceasefire in place, but the Russian leadership isn’t. We’ve gotta change that calculation, and that’s more than anything, I think, a function of whether we give Ukraine greater military help, which persuades Putin that more war will not give him more results. Frazer Rice (05:15.571)Any inside baseball and any potential weaknesses in Russia that we don’t hear about over here, as opposed to sort of the general posturing we get from Putin? Richard Haass (05:25.389) There’s been a lot of talk about it recently. The president mused on true social, about Russia’s economy and so forth. Look, Russia’s paid an enormous price for the war in terms of manpower, in terms of its economy. But China continues to buy oil, India continues to buy oil, Turkey continues to buy oil. So think the Russian economy limps along. Militarily, they’ve got a pretty good wartime economy. Putin still controls the narrative within Russia. I don’t sense, I’d love to be wrong, but I don’t sense that Russia’s on any brink where it can’t sustain a version of what it is doing. So no, no, could we reach a point, phrase it like that, is no longer true, and Russia, literally and figuratively, begins to run out of gas? Yeah. But I don’t think we’re there yet, but time, the medium to long term is not in Russia’s favor, only because their productive capabilities are getting diminished and so forth. again, I still think what we want to do is help Ukraine more. don’t know if we will. I don’t know if we’re going to impose sanctions. can’t explain why this reluctance to pressure Russia directly and indirectly. It gets into places I don’t have any evidence on. But I would simply say…President Trump is right to want to bring peace. I think he’s sabotaging or undermining his own US Foreign Policy efforts by not creating a context in which diplomacy is more likely to succeed. But I don’t see any signs at the moment that either side is ready to essentially shout uncle. US FOREIGN POLICY: ISRAEL AND GAZA Frazer Rice (07:10.163)Trump just came out with his 10 or 20 point plan for Israel and Gaza to Richard Haass (07:15.373)It was to inflationary times. It was 20. Frazer Rice (07:18.951)It’s power of compounding. Hopefully, maybe that’ll help. What do you make of that? We’ve just had all sorts of different iterations of from the invasion to the counter invasion to all the fighting. on one hand, I’m happy to see that there’s an attempt to try to stake out some peace plans here, but I’m not confident that it will come to pass. Do you have any thoughts on that? Richard Haass (07:44.258) I pretty much agree with what you said. Look, it’s the shortest 20-point plan in history. And by that, I mean there’s 20 points to it, but none of them is fleshed out. So the immediate question is whether Hamas agrees to it, the Israeli government did. But even if Hamas does any number of implementation questions. Certain preconditions have to be met and so forth. When I used to teach at Harvard, we used to say that 90 % of life is implementation. Well, this plan is the 10%. It’s a design. It includes all the things a peace plan would need to include, at least it mentions them. But they’re not developed. And so all sorts of things to tall for a technocratic that could run Gaza, a stabilization force, full humanitarian aid, all sorts of things about political and diplomatic processes. The plan is more, I guess I’d say it’s more aspirational than operational. So the good news is the Israeli government agreed to it. We’ll see what Hamas does. My own guess is at some point, There’ll be all sorts of hiccups in implementation. And probably early next year, in the spring or so, I expect Bibi Netanyahu will call for new elections. He’s got to do it within the next 12, 13 months. He’ll choose an opportune moment. The fact that he’s gotten this plan put forward, which is quite sensitive, shall we say, to Israeli interests, and he’s agreed to it, puts him in a very good position. So either Hamas…capitulates or Israel’s given a green light to continue the war from the United States. So I think, my own view is this plan in its current form will not reach fruition to say the least. And at some point sooner rather than later, we’ll probably have Israeli elections, possibly as soon as six, seven, eight months from now. CHINA AND INDA Frazer Rice (09:48.392)Got it. So it would be geopolitically crazy not to talk about the two most populous nations in China and India. I know they got together with Russia in the room as well to maybe to broadcast their sort of emergent standing in the world. Is there anything we should be watching on that front besides sort of the obvious in terms of how they deal with themselves and how they deal with US Foreign Policy, especially in a tariff environment? US FOREIGN POLICY: INDIA Richard Haass (10:16.279) Couple things come to mind, in terms of India. I think it’s fair to accuse the administration of diplomatic malpractice. The U.S.-Indian relationship has been carefully nurtured over the last few decades by Republican and Democratic presidents alike. It made sense economically. India is the world’s l

In this conversation on “TAX ALPHA”, Frazer Rice and BRENT SULLIVAN (of TAX ALPHA INSIDER) delve into the complexities of tax awareness in investing, focusing on capital gains, income tax, and various strategies for tax efficiency. They discuss the importance of tax loss harvesting, the challenges of managing concentrated portfolios, and the implications of estate planning. The conversation emphasizes the need for advisors and trustees to understand these strategies to optimize tax outcomes for their clients. https://youtu.be/pCIXFq4YoS0 Outline of Tax Alpha Quick Overview of Tax Rates Ordinary vs Capital Gain (Usually Income vs Asset based taxation) Short Term vs Long Term (Long Term Treatment) (we’ll talk about Estate Later) Federal vs State (Can be important!) Netting Losses/Deductions vs Gains and Income Owning assets Taxable vs Non-Taxable vehicles https://open.spotify.com/episode/3uL924aOlPd2hgmC9s7KCI?si=hBS09OKDTd-uHhT8PAj7aA Tax Alpha in stock investing (Universe) Long Only Concentrated Positions Timing – Getting LT Capital Gain treatment Basis – increasing basis Exchange / 351 Funds to defer and diversify Dramatic foreshadowing with step-up later in estate context Blind Trusts for political appointees Diversified Positions Passive (Lower Cost, acceptable returns, “lower risk/tracking error”) Active (Now frowned upon – except in the after tax world w/ TLH) Deferral Carve-Outs like QOZ’s Tax Lost Harvesting Owning an index vs owning a sample of the index Buying Coke and selling pepsi Wash Rules Loss Carry Forwards Capital Losses / Not Ordiany Losses Amplified Tax Loss Harvesting Own the sample of Index AND Borrow off those holdings to create long and short positions to generate capital losses while having beta of 1 Trends: Pre-Liquidity Event planning Storing Losses for the bulky sale Timing the event(s) to have the losses line up with the gains Pre-Diversification planning Pre Death Planning Integrating the Estate Planning with the Income/ Cap Gains Planning Step-Up Avoiding Estate Tax, But Prolonging the Cap Gains Tax exposure (and concentration risk?) Grantor Tax status and he swap power How does turbo charged loss creation look in an estate environment? Trustee/ Executor and Fiduciary / Beneficiary risk issues Vehicle evolution Funds SMA’s 351 and other ETF vehicles (+/-‘s) PPLI,PPVA How did you develop this expertise? How do we find you? Transcript of Tax Alpha Frazer Rice (00:01.122)Welcome aboard, Brent. Brent Sullivan (00:03.035)Well, happy to be here, Fraser. Frazer Rice (00:04.558)It’s fun to chat in person. I’ve been following it to call a blog I don’t think gives it the proper respect because I think you’re uncovering a lot of great information for advisors like me and wealthy people and other people generally speaking in terms of Really getting going on the tax alpha end of it Let’s start a little bit with some basics because I think you know for someone new to the concept of Being particularly tax aware in terms of investing taxes can be, they’re more than just income tax, that’s for sure. How do you think about it? How do you get your framework around what people are trying to avoid when they’re dealing with their investable portfolios? Brent Sullivan (00:45.723)Yeah, I mean, there are really just a couple of different ways to break it down, but I probably start with the concept of a capital gain as a distinct thing from income tax. so capital gains come in really like four different flavors. There’s short-term capital gains, short-term capital losses, and then long-term capital gains, long-term capital losses. And then these things are different if you have collectibles or other types of instruments too. But the point is here that you’ve got those four quadrants that you’re always sort of operating in. And I think that’s where the management and the prowess around portfolio design, execution, that’s where all of that really comes into play. And the final point I’d make about capital gains versus income is that capital gains is really a planning opportunity. Income is gonna come at you and there’s really not much you can do about it. Strong caveat to that. But capital gains are really about timing. You can accelerate losses, you can defer gains. Frazer Rice (01:37.929)Right. Brent Sullivan (01:45.079)And that’s really the beginning of the conversation when I’m talking with advisors about this usually. I operate in B2B space, I’m not retail facing. And usually that’s where the planning conversation starts. Frazer Rice (01:57.655)So as you sort of step back and help people think about the tax planning aspect of it, for advisors generally speaking, they’re very interested not only in the investment perspective, but the structuring of wealth such that they’re taking advantage of what they can and mitigating that which is destructive, but otherwise not really something they can avoid. If we settle in a little bit on the investment piece a little bit, what is the universe that we’re looking in in terms of how people allocate their portfolios? Brent Sullivan (02:33.22)Well, mean, so probably I’d say the hot topic in tax management nowadays is really getting the portfolio to be more equity like. And so the reason or part of the motivation for more equity like exposure is to utilize to the extent possible the planning opportunity of capital gains, realization and acceleration and things like that. So that’s that’s probably the core concept. The biggest chunk of the investable portfolio. The idea is to make it more equity like. And then the planning opportunities sort of expand beyond the core portfolio. That’s in, you know, how can we align total diversified exposure across the right types of investment accounts? In your space, it starts to get really interesting. You know, I say your space, like in a state planning world, it starts to get, you know, the idea of asset location, putting the stocks, you know, in the high growth portfolios or tax exempt portfolios, depending on the profile. Frazer Rice (03:17.228)Sure. Brent Sullivan (03:26.458)Putting the bonds in tax advantaged accounts or tax exempt accounts, again, depending on the profile. All of that is like, these are like really crisp, interesting planning questions that do not have crisp answers. And I think that’s where the planning opportunity really emerges. Frazer Rice (03:42.668)We talk a little bit about asset location. The investment vehicles we’ll talk about shortly and some of the things that can happen to turn the dials on that front. But in terms of location in whether ERISA accounts or life insurance or trusts or things like that, as people are trying to get their arms around the matrix, as you called it, and certainly with the capital gains and short and long, there’s almost a matrix of different things you can think about in terms of the tools in your toolkit. How do you get your arms around that if you’re new to the space or otherwise trying to really provide subtle advice as opposed to maybe speculative advice? Brent Sullivan (04:23.214)Yeah, I mean, I think that the first step is really trying to understand how each investment decision impacts not just the current investment returns, but also future investment returns, after-tax returns, pre-liquidation, post-liquidation, but then also estate considerations, like are you choosing the right vehicle if you’re trying to isolate or exclude assets from the estate? Do you want to keep a strategy on for multi-generations? Is it private? Public? Is it liquid? Iliquid? Inflation protected? All this kind of stuff. You have to realize that every single investment decision involves or impacts this really complex ecosystem. It’s super interesting, but I think like first order decision is like how much of a thing should I own? That is just like the tip of the iceberg. And I would say that’s where 99 % of like the financial media focuses. You how should I invest a million dollars now? It’s like, no, boy. Like there’s so much more ground to cover that could make portfolios resilient today, but also with multi-generation in mind. Frazer Rice (05:29.835)As I like to say, trying to get past the two dimensions that most people are normally thinking about in terms of the X and Y of income and capital gains and then sort of layering on asset allocation to be responsible on that front, but then add the Z axis of the estate planning, really kind of years 10, 15, 20, and then going beyond your use of the assets to different constituencies that are going to benefit from it later. Brent Sullivan (05:55.365)I mean, I get so excited when I think about the opportunities in this space because they’re so messy and bespoke. And I say messy in a good way. These are real problems that planners have an opportunity to step in and address for high net worth folks. really, down market, I don’t say down market in a pejorative sense, but mean, in down market too, there are really opportunities for planners to step in and add meaningful value and like again, I am an observer of this industry. I’m an independent tax analyst, which means that I don’t have a stake in the game. I don’t, I’m not trying to sell anyone’s product. So I just get to see the opportunities that planners have when they’re engaging with, with clients at all wealth levels. And again, like to your point, yeah, multi-generation is super exciting. It’s so messy and interesting. Frazer Rice (06:43.755)As we look at it here, the one unifying theme is most people don’t want to pay taxes if they don’t have to. success really does come down to what do you get to keep at the end of the day from the fruits of your labor or your investment. Without that unifying principle, then we’re sort of grasping at straws I guess. Let’s start with the simplest sort of tools that we have in the toolbox. And this is gonna combine a little bit of investment vehicle and tax awareness in the long only space? What are the thin

In this conversation, Frazer Rice and PAUL HOOD delve into the evolving role of trustees, particularly in the context of Delaware’s new Well-Being Trust Statute. They discuss the broader responsibilities of trustees beyond mere asset management, emphasizing the importance of understanding beneficiaries’ needs and the implications of well-being provisions. The dialogue highlights the challenges trustees face in balancing the interests of multiple beneficiaries, the potential liabilities associated with well-being services, and the necessity of having clear processes in place. The conversation concludes with reflections on the complexities of trust management and the importance of careful drafting in trust documents. https://youtu.be/9LFt6HsjpWM https://open.spotify.com/episode/4uqhoeXtfaIIWLbKhd62ej?si=nDTf-09bRSWjT0O_YKX49g Takeaways Trustees have a broader role than just managing assets. The well-being statute in Delaware is an opt-in provision. Balancing the needs of multiple beneficiaries is challenging. A clear process is essential for trustees to navigate their duties. Well-being provisions can complicate traditional trust structures. Trustees must be cautious about the liabilities they assume. Decanting trusts can lead to unintended consequences. The intent of the settlor is paramount in trust management. Trustees should document their decision-making processes. Effective communication with beneficiaries is crucial. Sound bites “I would never opt into 3345.”“Decanting is not that easy.” Well Being Trust Chapters 00:00 Understanding the Role of Trustees04:45 The Concept of Well-Being in Trusts10:33 Balancing Beneficiary Needs17:53 Navigating Well-Being Responsibilities24:30 Challenges and Considerations in Trust Management Well Being Trust Transcript Frazer Rice (00:01.078)Welcome aboard, Pop. Paul Hood (00:02.648)Great to be with you today. Frazer Rice (00:04.598)The Delaware legislature has tried to give us some new tools to give us a holistic approach to planning for trustees and for beneficiaries. Help us sort of think through first from a function perspective what trustees do. I always thought of it as, you know, they held assets for the benefit of beneficiaries and then with that they have to administer them, they have to invest them, and then they have to distribute them. Have we got that about right? Paul Hood (00:35.34)Well, I’ve always had a broader view of trustees. Jay Hughes, a good friend and fellow pilgrim in this field, he talks about the trustee as a persons with confidence and like a trainer, an elder, and for a lot of beneficiaries, and I believe trustees, especially in discretionary trusts, The trustee needs to be that. There needs to be some attention to the person of the beneficiary, not just the finances. Send us a budget. The distributions committee who’s in secret will meet, and we’ll decide how much we’ll give you. Well, I think a trustee’s duty is broader than that. Or let’s say this, you can meet the minimum requirements of being a trustee by doing what you said, but I think the very, very best trustees are persons with confidence. Frazer Rice (01:41.17)I agree with that. The problem is identifying the people who mix the temperament and the talent and then paying for them. So to that end, with those different functions, the world of bifurcation came about. Directed trustees where people got to be good at certain things. Maybe you had a good investment person, you had someone who was with the family who understood the dynamics from a distribution standpoint. and then the administrative side making sure the I’s are dotted and the T’s are crossed as far as the administration’s concern. How do you view that in the evolution of the trustee function? Paul Hood (02:17.612)Well, it’s interesting because I haven’t been in practice. since well the 20th anniversary of Hurricane Katrina is August 29th of this year. My life changed that day. I didn’t know it but it did. And I left Louisiana. So I haven’t practiced law in 20 years but I remember the directed trust percolating up and it was driven by the investments. People wanted the bank trust or the institutional trustees but they hated their investment performance. So the compromise was, okay, we’ll reduce our duties because the bugaboo was always whether it was a proper delegation of investment authority. The trustee could still be held liable for what if the court thought it was an improper delegation, okay, or oversight of the delegation. They started out investing right, but then they got real heavy in crypto and foreign flips. you can go there. So we’ll take fewer basis points, but we don’t have the liability for that. That liability is not delegated. We have segregated it. But enter the Wellbeing Trust, and this is only true in Delaware in the Wellbeing Trust statute because it’s an opt-in. Once you opt-in, you are required, the trustee and all the advisors are required to perform that those well-being, provide those well-being services. Now the question is who is responsible for providing them. Frazer Rice (04:16.891)Let’s step back for a second. The well-being provision, which is designed to give the trustee the tool to promote, improve, advance the well-being of the beneficiaries, which I think we can agree is a good thing in concept. What do we think of well-being as being? How is it defined? And what part of the function is it taking from the trustee’s perspective? Paul Hood (04:45.228)Well, I’m going to default back to, I think it was Potter Stewart who said he knows pornography when he sees it. I think that’s the same with well-being. I think things are either obviously well-being related and are not. And there’s a continuum of them. But the whole concept, I think it’s just pretty much to promote the betterment, the improvement and the just the the maintenance personal maintenance of a trustee i mean of a a beneficiary Frazer Rice (05:26.269)So how do you think about it from a trustee’s perspective when there are multiple beneficiaries and maybe the wellbeing for one is not the wellbeing for another? Very often a trustee has to balance a lot of different equities and I don’t mean that from a stock perspective, sort of taking care of one possibly at the expense of the other with the trust’s assets. How does the new statute in Delaware address that? Paul Hood (05:54.222)Well, and you raise an excellent point. what you said, you were talking about equities, okay? What it really is, is the trustees duties. And the big one is the duty of impartiality. And arguably, the 3345 statute, and I’ll call it that, that’s the wellbeing statute. That’s the opt-in. They have another one and it is to provide, it’s an immediate power. It was added to 3325 as number 32 in the Delaware trust code. And it allows almost the same things. It empowers trustees, now not the advisors. It doesn’t say anything about the advisors in that statute. Whereas 3345 includes, and remember in Delaware an advisor is like the trust protector and the administrative trustee, that kind of thing. They call them advisors. I don’t favor that language because I believe that they should all be fiduciaries. So I call them trustees because I think in the end they’re going to be held, especially if they’re professionals, they’re going to be held to that standard as it is. But that statute was immediate when the law went into effect. So they’re authorized to provide those services now. For me, would provide, I would never opt into that statute. Because why do you want to take on a mandatory duty that’s unclear? Frazer Rice (07:30.12)That’s it. Frazer Rice (07:34.908)Yeah, it sounds like a Roach Motel where you get in but you can’t leave. That’s right. That’s right. So if you were to encounter one of these trusts in the wild and you’ve got multiple beneficiaries, but let’s say three, one of them needs a lot of help. Another one could use the help and then the other one is completely self-sufficient. How do you… Paul Hood (07:40.35)Eagles Hotel, California. You can check out anytime you like, but you can never leave. Frazer Rice (08:02.693)sort of build a process around that so that you are being impartial but you are invariably taking away from potentially the corpus of the trust in order to effectuate different goals as they develop for these beneficiaries. Paul Hood (08:16.782)Well, it obviously starts with the settlors intent. And it’s the settlors intent first as set forth in the instrument. However, because this is not a court case where you’re construing, because I I used be an expert witness, know, construing, you know, problematic clauses in operating agreements, trusts, wills, whatever. You, you, you, you construe that including more information you investigate. The trustee, let’s look more, because you look at the language and well it would authorize it here, but let me find out a little bit more. If the settlor is still alive, I would at a minimum also talk to the settlor, okay? Also, if he or she is not still alive or sentient, I would investigate. I would talk to other people. I would make that into a process so that when you’re questioned down the road, here’s my process. Anytime you have a process, you’re better off. When all that planning was done in 2012, you know, and we filed more gift tax returns. I was the only guy in the country saying, don’t. put your marginal wealth clients into anything big, irrevocable. I said, because I think this is gonna work itself out. And for six hours, I was wrong on January the 1st, 2013, but there were lawsuits. And Jackson versus Colon was one of the cases and poor Colon, the lawyer got sued. because he didn’t have a process for evaluating whether his client had put too much or had retained sufficient assets after they did this planning. So it’s all about a process in the end. So instrument, settlor, and I would investigate and I would wrap it up into a process that was documented. Frazer Rice (10:36.848)So if I

We go inside the the enormity, complication, and notoriety of the BEZOS PRE-NUP AGREEMENT with divorce attorney, MARILYN CHINITZ of BLANK ROME. https://youtu.be/nMMp6He056Y https://open.spotify.com/episode/39KMPMRhwGfYbdZVMJHEan?si=36c5c8a927bf4a6f Outline of the ISSUES INSIDE the BEZOS PRE-NUP General Concepts What happens without a pre-nup? Process for disclosing assets Previous marriages and those pre/post-nups? Community vs Equitable Distribution (Does the Pre-Nup contract this away?) Separate property Outside trusts?  Estate Planning? Pre-nup vs ultra high net worth pre-nup Financial Considerations (and Complication) Non-Financial- NDA, media activity, scope of negotiations, data and tech issues Let’s go through the General Fact Pattern High Profile Asymmetric Net Worths Kids? Which state is used for choice of law? Portability?  How do you make sure this has teeth?  (Coercion penalties) Spousal support / alimony? Escalator or sunset clauses? Disqualifying or  “infidelity” or “weight gain” clauses? What happens if children? Other constituencies – charities, businesses, political causes etc  Integration with estate documents, life insurance, other vehicles Is there a check-in every five years? What else can we learn from what is inside the Bezos Pre-Nup? Transcript Frazer Rice (00:02.07) – Inside the Bezos Pre-Nup Welcome aboard, Marilyn. Marilyn Chinitz (00:04.088) Thank you, really nice to be here and nice to talk to you about what’s inside the Bezos Pre-Nup. Frazer Rice (00:07.541) We sort of regaled ourselves with a mutual friend and we’re already, I feel like we’re already related. That’s right. So we’re going to talk a little bit about probably one of the highest profile marriages in the world that just happened with the Bezos Sanchez union and get inside the Bezos pre-Nup. But for just for a little bit here, let’s talk about what happens in a sort of family law divorce setting. Marilyn Chinitz (00:13.39) Your best and glorious buddies are ready. Frazer Rice (00:35.232) With general concepts because we’re going to be diving into some specifics with the case study here. What happens when something goes wrong and we have a divorce that happens without a prenup? Marilyn Chinitz (00:46.734) So it depends what state you’re in. If you’re in a state like New York, then we have equitable distribution laws. If you’re in a state like community property in California, then those laws are very different. So if you have no prenup, and a lot of people don’t because they start their marriage with very little assets, and everything that you acquired during your marriage is now subject to a division. Frazer Rice (00:49.569) Of course. Marilyn Chinitz (01:15.918) And what happens is you start to trace the assets and you look at, what do I have? You look at homes that you purchase, real estate that you purchase, stocks, securities that you purchased. It doesn’t matter in whose name the asset is held. It’s a marital asset if it was acquired during the marriage and it was not gifted or inherited. If you come into the marriage with assets and you have no prenuptial agreement and you keep those separate property assets clean, and I’ll explain what that means. When they go up in value because you actively caused their appreciation, they may be subject to a marital claim, the appreciation aspect. If you… have an asset that went up in value because of passive reasons and you kept that asset separate, it will remain separate property. So let’s talk about an example. If I owned a building before I got married and that building was worth five million dollars and then I get married and years later I get divorced, that building is now worth twenty million dollars. It appreciated by 15 million. Did it appreciate because of market fluctuation, because the market went up, real estate did better? Or did it appreciate in value because I managed it, I collected the rent, I made sure the repairs were done, I made renovations to the building, and therefore it went up in value. If it went up in value during the marriage because I actively did something, I renovated, I took care of the building, I managed the building. That appreciation from five million to 20 million is gonna be considered marital. Then the question is, what percentage does the other spouse get? Do they get 10 % of the appreciation or 50 % of the appreciation? If that asset went up because of market fluctuation, I sat back, I did nothing, the market went sky high. Marilyn Chinitz (03:38.905) Then that property will remain separate property and the appreciation is separate. So you have to look at those different factors. But other than that, if you come into the marriage with no assets and you create a marital estate and you have no pre-nup, that marital estate is going to be divided. Now the question is, how is it going to be divided? If you’re in an equitable distribution state, Frazer Rice (04:04.907) Right. Marilyn Chinitz (04:08.718) What does that mean? It means what a particular judge feels in a particular courtroom on a particular day. What does equitable mean? It’s completely subjective. So did the other spouse take care of two, three children while you were managing that property? Did the other spouse work but supported you? Or did the other spouse do their own thing and had no real contribution? It’s very fact specific. And if you can show that the spouse really contributed in a meaningful way while you were running your business or running your properties, I took care of the children, I took care of the home, I took care of you, then the court is likely to give you a more substantial percentage interest of that appreciation. And in New York, for example, equitable, and then we’ll talk about community, California, for example, generally, Bank accounts, retirement accounts, stock security accounts are going to be divided pretty much 50-50. Where the court will not give 50-50 is if it’s a business. And then the court can go anywhere from 10%, 15%, 20%, up to maybe 40 % in unusual cases. What do those cases look like? They work together in the business. They took care of things together. It’s very unusual for a court to give 40 % interest to the non-working spouse unless they were really actively involved in the business. Now, conversely, take California, which is a community property. When you get married and you acquire property in California, that’s 50-50 off the bat. Now, why does that become really important? We’re seeing a lot of cases where people have really created a lot of wealth in their marriage and they are correctly and smartly putting some of that wealth into trust. They’re gifting it to a trust for their children. New York, for example, is a title state. A title state means if I own the asset during my marriage, I can sell it, I can gift it, I can do whatever I want with it. Marilyn Chinitz (06:33.718) As long as there’s no divorce. If you are in a community property state, you can’t do that because that person, that spouse already owns 50%. It’s almost jointly owned. So you can’t give away a marital asset unless you consult with me, your spouse, unless you ask me, is it okay? So in New York, if I wanted to take an asset, an interest that I own during the marriage, it’s a marital asset, but because there’s no divorce, there’s nothing that prohibits me, I gift it to a trust, I have the right to do that. In California, I may not have the right to do that unless I got my spouse’s consent. So, number one, what’s critically important is you need to know what the laws are in the different states. Now, Sometimes people get married. They get married in New York. They enter into a prenuptial agreement in New York. But now they move to California that has very different laws. And if they thought they were going to move to California, then you want to make sure as a New York lawyer to advise the client, we need to engage California counsel. We need to find out what their laws are so that your prenup is portable, it could be enforced in a different jurisdiction. Frazer Rice (08:03.559)So choice of law, obviously very important. Then I would say sort of the process and hygiene around using assets and deciding what happens jointly versus what stays separate is something that’s important to manage going forward. How do you think about that with clients? Marilyn Chinitz (08:20.346)So, I mean, interestingly enough, when I do a, let’s talk about prenups for a minute. Because when I do a prenup for a client, we have a check-in every year. We go to lunch. We talk about what changes, what’s going on. Does the agreement need to be modified? So many times people will sign a prenuptial agreement, they put it away, they don’t even know where they put it. And 20 years later, sadly, somebody triggered. the terms of that agreement. Now they pull it out and they go, my God, everything’s changed. When we signed that agreement, he was only worth X amount. He’s now 20 times wealthier, but I didn’t increase anything. That’s not fair. If the agreement is…an agreement that you entered into with the advice of counsel. If the agreement had full financial disclosure, if the agreement was negotiated, if you had your own counsel, etc., all the bells and whistles, it may be an unfair agreement, but it’s going to be enforceable unless it is unconscionable. So what does unconscionable mean? Unconscionable means shocking to the conscience. So I represented, and I could say it because it was in the media, Liba Icahn, married to Carl Icahn. And he had a prenuptial agreement prepared, and she signed it. Years later, he decided he wanted a divorce. And she argued to the court, I was not her first lawyer. I was not her second lawyer, I was her third lawyer. And I’ll tell you why that was important. She argued to the court that the agreement is unconscionable. He’s now worth several billions of dollars, and all I got was X amount of dollars. That’s unconscionable shocking to the conscie

NICK MAGGIULLI, successful author of “Just Keep Buying” has a new book out called “THE WEALTH LADDER.” It’s a well done framework on how one’s relationship with money has to change as they move up the different strata of money and spending. We get into the book, how major life changes can shape our views, and the writing process. https://youtu.be/pFmWTHlPTUY https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial-ebook/dp/B0DKMPFTR3/ OUTLINE What does this book seek to accomplish? How was the experience different from the last book? Surprises in your findings? Has getting engaged and married change your lens on any of these topics? THE SIX LEVELS OF THE WEALTH LADDER Level 1: Less Than $10,000 Level 2: $10,000 – $100,000 Level 3: $100,000- $1M Level 4: $1M-$10M Level 5: $10M-$100M Level 6: $100M and beyond TRANSCRIPT Frazer Rice (00:02.178)Welcome aboard, Nick. Nick Maggiulli (00:04.138)Thanks for having me back, Frazer. Appreciate it. Frazer Rice (00:04.911)Easy to have you back and congratulations on two fronts. You just got married and you’ve also in a sense given birth to a new publication here. Tell us about the last few months and what it’s been like. Nick Maggiulli (00:14.41) It’s just been very busy, lots of things. We were doing wedding planning. We got engaged late last year and so wedding planning did that, had a few small celebrations. And now it’s book launch time. We’re delaying our honeymoon until the end of August because the book’s coming out now and the book’s out, so going from there. So it’s been fun. Frazer Rice (00:38.094)Big things happen in three, so it’s all coming together in a couple of months there. So I’ve been watching this book getting written over the course of last, I guess, two years now. What was the gist of the book for the audience here? What got you into the wealth ladder concept, having written Just Keep Buying? Nick Maggiulli (00:41.374)Yeah. So the gist of the book is that your financial strategy needs to change over time. I think it’s very easy to get caught in a certain set of habits and you can follow those to their logical conclusion. But if you’re trying to kind of go to the next level, so to speak, as I say in the wealth ladder, you might need to change your strategy. And there’s a ton of examples of this and it really depends where you want to go, how much wealth you want to accumulate, etc. Knowing all those things will help you better determine which strategy you should follow. That’s the high level of the wealth ladder. Frazer Rice (01:30.574)So as you were sort of getting into the research on it and you take a lot from your personal experiences, you’ve moved up the wealth ladder and have had to have a little self-discovery on that. What would have been the interesting findings in your own experience and in the research that you’ve had and maybe things that were surprising? Nick Maggiulli (01:51.338) the Origins of the Wealth LadderI think this is something that I’m hoping a lot of people who have built wealth have come to the same conclusions, which is like as you build more wealth and have more money, like money doesn’t mean the same thing to you anymore. It doesn’t have the same value. Like I remember still being a, you know, semi-broke college student, you know, and then being a, you know, semi-broke just graduated college student, just started earning money and stuff. And I remember not wanting to pay for a beer at a festival because it was $9. And now that beer is probably 15 or 20 bucks. But at the time I was like, this is crazy. I can’t pay for this. But looking back now, it was because I just didn’t have a lot of money and I was trying to be very careful about my spending today. Looking back, if I had known everything I know now, I’d be like, I can, I can buy the beer. I’ll be okay. Right. I don’t have to sneak these little mini liquor bottles and all the crazy stuff I used to do. Right. That’s like an example of like over time, just money changes. Because of that, you’re like, yeah, I shouldn’t have been as, you know, I shouldn’t have cut back as much when I was younger. also just how you view it. I view it more as a tool now and less from like as a scarce resource. Like it’s a tool I can use to do things. I can help my family with it or travel with it. I can donate. There’s all sorts of different things you can do with your money. And I think seeing it as a tool is really the important part. And lastly, it’s just how like the amount of money I need to change my lifestyle just keeps getting bigger and bigger. Right. We’re like, you know, ten thousand dollars back when I was 22 would have been like, wow, that’s like a ton of safety. I wouldn’t worry as much about money. Today, $10,000 just doesn’t mean as much as it used to. And so it’s great. would still be, used, hand me a $10,000 check. That’s great. I’d be happy, but not even close to as happy or wouldn’t have as, as big of an impact on my life as it would have when I was 23. Right. I think everyone understands that, you know, what’s $10,000 to someone with a million. It’s not as big of a deal compared to someone with close to nothing. And so, yeah. Frazer Rice (03:36.14)Yeah, one of the things that, you know, as was reading the book, super interesting is the idea that as you move up the wealth ladder and more and more people become involved and are part of your responsibility umbrella in many ways. And it gets back to something I wrote in mind where I talk about how the liabilities increase geometrically even though the assets may increase linearly. Is there a process around when you start thinking less about yourself and wealth than you start thinking about a family unit and then… intergenerationally and beyond. It’s something that I think gets lost in many times in the sort of the financial planning shuffle, but it’s something that I think your book covers well. Nick Maggiulli (04:23.454)Yeah, I think the big error that people make in that front is thinking too much about the monetary and the financial piece of that and not the non-financial piece of it. So it’s like, Hey, my gosh, I accumulated, say $20 million and I’m going to have this for three generations and I’m planning this and I’ve trust and all this stuff. And you can set up all these structures and do everything perfectly right. But if you don’t have the right relationship with your kids, if you guys don’t have a shared set of values to build off of going forward, It’s going to derail as soon as you’re gone because you know, maybe they’re just following your wishes while you’re here and as soon as you’ve passed, how do you know that those things are going to live on? You don’t at all, right? At the end of the day, I think what’s more important is having a stronger relationship with your children so that you can talk about these things and listen to them, get their feedback and then plan your money more together instead of just doing it completely on your own and trying to create this control beyond the grave, right? And I think that’s what can create other issues within the family. It’s the thing that people overlook because I think everyone’s just like, if I just get the wealth and it’ll last. And I don’t think the second part is true unless you have the value set up. You’ve thought about all these other things that people tend to overlook. Frazer Rice (05:35.883) the Wealth Ladder and CouplesJoelle and Doug Bonaparte have come out with a book about wealth and marriage and money and you’re going through it right now having just been married. What’s been sort of the first takeaway in getting married and sort of the principles of the wealth ladder? And I guess another different way of asking that is how do you merge your way of thinking about these wealth concepts with what your wife is thinking about? It’s not pinning you down specifically, you’ve been buried above. But at the same time, I’m sure you saw that where when you’re merging different views on wealth and as you sort of put a timeframe and a ladder frame to it, what have you found interesting in your research on Nick Maggiulli (06:22.25)Yeah, so I haven’t done too much research on couples in particular. I can tell you that my wife and I are very aligned on a of our finances. She’s actually more frugal than I am. I try and I even use, you she’s read the book at this point, right? Cause I, you know, I was writing in and I gave it to her. Frazer Rice (06:34.526)You forced her! Nick Maggiulli (06:51.69) Yeah. And for no, she wants, she wanted to read it on her own. So she wrote like a EPUB version of it and read it and stuff. She really enjoyed it. But I think for her, like she still has trouble spending money. And so I like came up with this spending framework using the 0.01 % rule, which is like, Hey, take your net worth multiplied by point zero one percent or divide by 10,000. It’s the same thing. That’s the amount of money that your wealth is like generating daily in like a very conservative sense. Right. If you point zero one percent do that, you know, let’s say 365 days in a row. That’s about three point seven percent a year. It’s a very conservative return. And so if we assume that like you could spend that in theory every day and it’s like a trivial amount of money to you So she’ll be like, oh, I don’t know if I want to spend 50 bucks on this thing. I’m like, baby, our net worth is over 500 K. So we don’t need to worry about that. Right. Because at 500 K, the point zero one percent rule would say you’re spending about 50 bucks a day on these like marginal purchases. So I’m trying to get her to not think through that. like, yes, obviously, your spending depends on your income. That’s obvious. But I think the marginal spending decision, hey, can I afford this thing? I like to think of it using this spending rule because it does scale very well with wealth. Right. And so I have these six levels of the Wealth Ladder and I can walk through those

The Business of Estate Planning is in the midst of a revolution- or is it? BRANDON RAINS discusses advising clients responsibly, profitability, and the “firm of the future.” https://youtu.be/a7VdZvrH9LI BRANDON RAINS from the Denver-based Rains Law Firm and I discuss estate planning in an era of artificial intelligence, scalability, the democratization of advice being delivered by non-lawyers and the fun and games that exist when people die and plans go into action. https://open.spotify.com/episode/6FeR3ACd8vXVkKyMZODnlu?si=Q0XrGGMRR92usDUiKcsT9g Outline for the BUSINESS OF ESTATE PLANNING What is involved with the process of educating/advising a person or family ? Good judgement, discretion, and experience is something worth paying for What does drafting and implementing involve? The benefits of “Professional Liability” and experience The intersection with technology / AI / drafting tools The dangers of DIY How to be a good client and get to adult conversations sooner Puttng thought into staffing important roles (and backups) Ongoing maintenance / administration Transcript Frazer Rice (00:02.954)I’m Frazer Rice. Today we have Brandon Rains. He is a practitioner in Colorado and owns his law firm in Denver. We’re going to talk a little bit about the business of estate planning and what it’s like to have an ongoing profitable enterprise when trying to help people arrange their affairs and do the right thing as far as advising. Brandon, welcome aboard. Brandon Rains (00:22.222) Thanks, Frazer. Pleasure to be here. Frazer Rice (00:23.926) So we’ve had a nice back and forth on the topic and maybe tell us a little bit about your practice generally and what you do, who your ideal client is, and then we can go into why we think it’s important to get paid for this type of advice. Brandon Rains (00:42.254) I my own firm about nine years ago, the Raines Law Firm, very originally and imaginatively named. I was leaving my previous firm, was interviewing with a bunch of other attorneys trying to find a good landing spot, and it just kind of hit home to me through those conversations and kind of debriefing with my mentor that they’re lots of times the state planning attorneys interact with their clients in the same way, generally speaking across the board. In some of those aspects, just not necessarily how I’m wired as a person, not that it’s necessarily better or worse or anything like that. I just felt that there might be more space and to kind of throw my elbows around within my own firm to kind of figure out what that could look like for me and serve clients in the best way possible. so started from scratch and still here and alive and kicking. Frazer Rice (01:38.028) So one of the things that I think is interesting is, I talk to people all the time and they indicate that they don’t understand the process of drafting and implementing and what does a lawyer actually do in putting together in a state plan? Take us through little bit about the process of advising and educating a client to help them understand what they’re identifying as far as an issue is concerned and then solving it. Brandon Rains (02:04.942) Well, I mean, think some of it is some of that answer is kind of what you would expect, right, which is asking good questions and listening. Beyond that, I think a lot of attorneys are going to be really different. I know that some attorneys that I’ve talked to, they have very strong feelings about our role to make recommendations, sometimes even tell the client what’s best for them or not. I think there are some situations where that makes sense. Again, it’s even though that’s not how I go about it, I think that they have, there’s some good sense there too. Some, think there’s a lot of decisions that can be personal that the client is best positioned to make those decisions of. so for me personally, kind of shy away from making recommendations for the most part, helping them have the information and advice and counsel that they’re looking for, for them to decide what’s best for them and their family. That’s kind of the tack that I take. For other attorneys, I know that they have stronger feelings. It’s like, we are not going to do this. This is not a good option. This is, you know, the best ones might say that and then explain why. But generally speaking, walking the clients through the decision-making process, I think offering that advice, being able to explain things in layman’s terms is so incredibly vital and important. Throwing… Legal jargon in our world doesn’t really offer too much help to people. They’re just going to end up just dazed and confused and going along with whatever you say because they don’t understand any better. I think deep down at the end of the day, that’s not really anything that what anybody wants. then, you know, understanding the questions that we’re asking, the decisions that we’re guiding our clients through is vital. as I understand, we’re gonna be talking even more about later on the benefits of working with an attorney as opposed to other options out there. But I think it’s kind of touching on that. And then on the back office side, you know, there’s over the last 10, 15 years, the growth of centralized drafting software programs has proliferated. Brandon Rains (04:31.982) Whereas before each firm would have their own templates and Word documents, copy, replace, copy, paste, and replace, and stuff like that. I know that there still some firms that still prefer to do it that way. But third party companies providing the forms that company, that attorneys or their staff use.has kind of proliferated. I personally am in that camp just being able to learn from hundreds or thousands of other attorneys and their experiences and the process of keeping those documents up to date with legal changes. It’s a lot easier with something like that. But sometimes that sense of ownership of those documents is lessened when someone else has prepared them and updating them and maintaining them. Sometimes it’s easy to take it for granted. But the process of drafting, the basic principles of drafting of legal advice are the same, really is we need to match the language that we prepare for our clients to their goals and their vision, their hopes, their dreams, their concerns. We really kind of capture all of that in the legal documents and do it in a way that’s understandable and ultimately is going to be effective after our clients have passed away. Then of course, walking clients through them and explaining it in the hopes that maybe a week or two after they’ve signed their documents, they might remember a thing or two of what they’ve been fighting. Frazer Rice (06:14.719) on the business of estate planning Always a challenge. One of the things I tell people is that you’re hiring an attorney to help you out on these situations because you’re going through it something that’s very complicated and opaque with huge ramifications for your life and after your life. With this being usually the first and only time that they’re dealing with that, it’s helpful to have a very well-equipped sherpa to help you along that journey. But then you’re also paying for the good judgment, the discretion and the experience that working with hundreds of other situations brings to bear to the instant case. describe that experience for me. You came from another firm, you decided to go this route and maybe a case study or something like that where a client really was able to find benefit from your having dealt with something similarly that occurred in your past experience. Brandon Rains (07:17.196) Yeah, I mean it’s you know there’s so many examples, but so it’s interesting how often clients come in. Like even just this morning, had a client, a couple come in, we had an initial meeting and kind of partway through that conversation, I was like, hey, do you have any questions for me in any way? It was kind of towards the beginning of the meeting a little bit. They were like, we don’t even know, we don’t know. We don’t even have the knowledge base to be able to ask you any questions in the first place. It’s like, okay, that’s fair. And so sometimes that’s just subject matter knowledge that is really helpful. I think a lot of times when couples and families benefit from our, to use your terms, your good judgment, discretion, and experience, we see that a lot when clients are making decisions. So it’s what makes sense, know, it’s, it’s, especially when children are struggling, right? I had some clients that I was meeting with earlier this week. We were helping them make decisions one of their one of their children is Just an amazing go-getter and the other one is struggling and so we had a real conversation about whether or not they should give money to their son or actually skip their son and go with give it to their grandson or granddaughter or whoever it was right, but just skipping that generation and walking them through that decision making process. Because some people, for example, think they don’t realize all the options regarding distributions to their loved ones. think it’s just everything. The only option they have is outright distributions, which is giving it to them all at once. Well, I don’t trust my child to give them everything all at once for drug addictions, manipulation, their spendthrift, whatever. So I just need to disinherit them. Sometimes clients have legitimately, literally come in with that mentality. When we talk to them and help them understand that there are more options than that to spread those distributions out over time and protect from those potential bad situations. That burden is just completely lifted off of their shoulders. It’s like, okay, I can give them money, but I can give it to them in a way that is best setting them up for success with some protections, with some guideposts, guidelines with some restraints because we think that’s really what their life and situatio

“IS THE CIO DRAGGING DOWN THE FAMILY OFFICE’S PERFORMANCE? (And What Can You Do About It?)” with R. ADAM SMITH. https://open.spotify.com/episode/1Cl26HkpjZBnovg3zumuBx?si=0c7e252e629d4603 https://youtu.be/p3VtFCVpp8o The Family Office CIO job involves a delicate high wire act. The position can be the fraught intersection of: Asset Allocation (& collision of “endowment” vs “family adjacent” strategy) Cash Management Deal Sourcer/Vetter Club Deal Gatekeeper Risk & FOMO mitigater Overall One-Man Band R. ADAM SMITH advises families around deal and investment structure via RAS CAPITAL PARTNERS. We discuss the evolving CIO in family offices, Our discussion addresses the importance of expectation-setting on both sides. We get into what the families can do to understand their own needs (and why they might be the problem!). The goal is to help both sides unlock potential and get out of the way of performance. Adam Smith’s Background (2–3 min) Adam gives a brief personal background and current work with family offices Set up the problem: Many family offices operate with misaligned or underperforming CIO structures Mention growing tension between opportunistic deal flow vs. structured allocation frameworks CIO Dragging: Defining the“Non-Functioning CIO” (3–4 min) Describe what a non-functioning or misaligned CIO looks like in a family office Common traits: reactive, relationship-driven over process-driven, lacking risk discipline The consequences: inconsistent returns, governance confusion, lack of accountability Deal-Driven vs. Allocation-Based Models (4–5 min) Explain the difference between a deal-centric CIO vs. one focused on institutional-style allocation Why the dealmaker mindset often prevails in emerging family offices Tradeoffs: speed and access vs. diversification, scalability, and defensibility Challenges when there’s no clear investment policy statement (IPS) Why Do Families Tolerate This? (2–3 min) Emotional and trust-based dynamics—families often default to familiarity over structure Over-indexing on “access” as value Underestimating the long-term risks of ad hoc strategies What CIO Institutionalization Looks Like (3–4 min) What a functional, institutional CIO framework looks like (clear mandate, reporting, delegation, rebalancing discipline) Role of governance in supporting this structure When and how to make the transition—triggers and best practices Cultural and Generational Resistance (2–3 min) Why some families resist institutionalization How generational shifts are challenging legacy CIO models Importance of aligning values and objectives—not just tactics Closing Thoughts THE CIO DRAGGING ON THE FAMILY OFFICE PERFORMANCE (2 min) Tie back to broader themes of sustainability, legacy, and governance in family offices Call to action: revisit your CIO model—does it reflect your goals or just your past? Emphasize the importance of aligning investment leadership with broader family vision Other CIO Dragging Considerations- Do the staffing and comp models adequately align the employer and employee?   What does a successful structure look like and how much does it cost?   What dos a minimum structure look like and how much does it cost?   Are CIO’s under resourced and put in a failing position?   How does career risk factor into CIO decision-making?   Does the threat to the family’s relevance in decision-making risk factor into this?   How much time is wasted doing “pretend” work to maintain access to other family offices deals?   Do you measure investment adjacency to the family specialty and how should that affect the evaluation of the CIO’s performance?   What happens when a deal-centric CIO is thrust into an asset class that is out of their expertise?   What is the benchmark performance for a FO CIO these days?   On the ESG, DEI, impact and philanthropy front, are these buckets in an overall allocation (sometimes where younger generations can be brought along?) or are you seeing FO’s incorporating the values metric in the overall allocation?  Is there a trend to think of family offices as useful for one generation and then to have them split up? BRIAN ADAMS ON FAMILY OFFICE RECRUITING https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/