The Modern CFO

Fanatics has rapidly emerged as a juggernaut in the world of licensed sports merchandise, collectibles, and online betting. What started as an online retailer in the late 1990s has transformed into a multi-billion dollar operation serving as the official e-commerce partner for major professional sports leagues like the NFL, NBA, MLB, NASCAR, as well as top college programs.Under the leadership of CFO Glenn Schiffman and executive chairman Michael Rubin, Fanatics has vertically integrated its operations by acquiring brands like Topps' sports collectibles business, and many others across manufacturing and, most recently, online betting platforms. This aggressive growth strategy has propelled Fanatics' revenue from just $250 million in 2012 to over $7 billion (as of 2022).The company has secured groundbreaking long-term merchandising rights partnerships with sports leagues, while also expanding into new revenue streams like collectible NFTs and online sports betting via Fanatics Betting & Gaming. With over 100 million customers in its database, Fanatics is uniquely positioned to provide a comprehensive, fan-first experience across merchandise, collectibles, and gambling verticals.In this episode, Glenn Schiffman pulls back the curtain on Fanatics' meteoric rise, sharing his journey from investment banking to CFO. He also highlights the company's forward-thinking acquisition strategy, how they attract top talent, and his vision for the future as Fanatics dominate the intersection of sports and entertainment.Show LinksConnect with Glenn H. Schiffman on LinkedInConnect with Andrew Seski on LinkedInLearn more about Fanatics

Join Dallas Clement, President and Chief Financial Officer of legendary Cox Enterprises, as he shares invaluable insights into his career journey, financial leadership, and how Cox's foundational values have been a beacon of success for 125+ years.With over three decades of experience, Dallas emphasizes the importance of balancing culture, learning, and growth in any financial professional’s career trajectory. He also delves into Cox's ethos of embracing risk and innovation, even if it means competing with themselves, to stay ahead of technology and trends.We were thrilled to have host Andrew Seski on-site at the wonderful Cox campus in Atlanta to record this episode, and we are grateful for Dallas’ contribution to the CFO conversation.Tune in for a thought-provoking discussion on leadership, strategic vision, and the enduring legacy of Cox Enterprises.Show LinksConnect with Dallas Clement on LinkedInConnect with Andrew Seski on LinkedInLearn more about Cox Enterprises

In this episode of The Modern CFO, Lauren StClair, CFO of NerdWallet, shares her unique career journey spanning across startups and large corporations like PayPal, eBay, and StubHub. She delves into the valuable lessons she's learned along the way, offering key takeaways for professionals in the finance and technology industries.Lauren's journey began at a small early-stage startup, where she quickly learned the value of resourcefulness and urgency in business. This experience taught her to wear multiple hats and connect the dots across various aspects of the company, providing a solid foundation for her future roles. However, she also realized the importance of understanding how to operate at scale and the need for best practices, leading her to pursue opportunities at larger organizations.During her tenure at eBay, Lauren had the opportunity to work in different functions, both within and outside of finance. She participated in a leadership development program, allowing her to complete multiple rotations across various departments. This experience not only expanded her functional skills but also taught her the importance of embracing change and humility.As Lauren reflects on her career path, she shares valuable insights for professionals navigating the dynamic landscape of finance and technology:Embrace change: Be open to new opportunities and challenges, as they provide valuable learning experiences and contribute to personal and professional growth.Develop a sense of resourcefulness: The ability to be resourceful and adaptable is crucial in today's fast-paced business environment.Learn to operate at scale: Understand the importance of implementing best practices and executing strategies that enable businesses to grow efficiently.Cultivate humility: Recognize when to ask for help, raise questions, and learn from others, as these traits are essential for continuous improvement and effective leadership.Lauren StClair's journey in the world of finance and technology offers a wealth of knowledge for individuals looking to build a successful career in these industries. Tune in to The Modern CFO podcast to hear the full conversation and gain inspiration from Lauren's remarkable story.Show LinksConnect with Lauren StClair Waugh on LinkedInConnect with Andrew Seski on LinkedInLearn more about NerdWallet on their website

"Am I continuing to learn? Am I continuing to create value?”These questions act as pillars for Eric Muhlheim, propelling his expansive career from studying mathematics to leading finance teams at one of the most dynamic tech organizations today.In our first episode of 2024, Eric and host of The Modern CFO, Andrew Seski, explore Eric's formative experiences at Morgan Stanley, his impactful tenure at Disney, and his transition into the world of tech leading him to his current role at Mozilla. Eric shares insights into Mozilla's unique corporate structure, its mission-driven approach, and the challenges and opportunities presented by the AI revolution.Listen in as Eric and Andrew discuss the importance of strategic implementation, the critical role of maintaining a strong, mission-aligned balance sheet, and Eric's personal approaches to leadership and relationship-building in the corporate world.Show LinksConnect with Eric on LinkedInConnect with Andrew on LinkedInCheck out the 2023 State of Mozilla

From investor to public company CFO, BLADE's Will Heyburn shares his path to the selective role of leading a finance team from the private markets through an IPO and beyond.In this episode of The Modern CFO, Will unpacks BLADE's unique evolution from passenger transportation to a leading medical organ transport provider and why they continue to focus on direct communication, data-driven decision-making, and building a customer-centric culture.Will and host Andrew Seski discuss the intricate balance between risk management, client satisfaction, and staying adaptable, especially as a technology platform within the aviation industry.Listen in for more secrets to BLADE's success and valuable lessons for aspiring CFOs navigating the future of technology within their own companies.Want to give BLADLE a try? Listeners can use Will's promo code* available towards the end of the episode! *Terms and conditions may applyShow LinksConnect with Will Heyburn on LinkedInConnect with Andrew Seski on LinkedInLearn more about BLADE on their website

In today's fast-paced marketplace, distinguishing what is important and impactful is a challenging task, and when a crisis unfolds rapidly, the stakes reach unprecedented heights. Steven Kelly, Associate Director of Research at the Yale Program on Financial Stability, joins us to discuss how navigating the choppy financial waters requires CFOs to possess a keen sense of judgment, as well as a sharp appetite for risk.Our conversation delves deep into financial stability, its critical tools for navigating fast-moving crises, its relationship with technology, and recent dynamics among banks, governments, and international markets.Listen in as we uncover valuable insights on how CFOs can better understand, mitigate, and effectively manage risk, offering a lifeline for those seeking to fortify their financial strategies and bridge the gaps in tomorrow's balance sheets. Show Links Connect with Steven Kelly on LinkedIn and on Twitter/X Connect with Andrew Seski on LinkedIn Learn more about Yale’s program on Financial Stability Discover more with the program’s knowledge base

In this episode, Mark Wilson, former CFO of iconic automotive brands McLaren and Aston Martin, reveals the keys to enduring success in an ever-changing industry. Now CFO at Verge, an electric motorbike company, he shares with us his strategy to marry cutting-edge performance innovations with an authentic human experience.We discuss the fundamental values of financial management, especially in fast-paced environments. Mark emphasizes the importance of discipline, rigor, and transparency in all financial decisions. We also talk about the power of partnerships built on mutual goals, where the sum or parts is far more valuable, while also highlighting strategies he’s used for avoiding one-sided deals.Listen in as we revel in Mark’s experiences at Aston Martin, where he successfully propelled the storied brand into the modern era—navigating great deals while also supporting legacy relationships, like that of the storied James Bond franchiseShow LinksConnect with Mark Wilson on LinkedInConnect with Andrew Seski on LinkedInDiscover Verge Motorcycles on their website

In a world where data reigns supreme, today's leaders need to balance the quantitative with the qualitative to lead, create, and inspire the next generation of CFOs.In his role as CFO at ThoughtSpot, Mohit Daswani leverages his extensive background gained from notable positions at JPMorgan, PayPal, and Square. He passionately champions the company's mission to forge a future grounded in data-driven decision-making. Having had the privilege of learning from industry luminaries such as Bob Swan, Sarah Friar, and John Rainey throughout his career, Mohit envisions an even more profound influence achieved through the power of machine learningListen in as Mohit discusses three core principles shaping his role with host Andrew Seski: building a fact-driven culture, learning from his mentor’s invaluable influence, and discovering the strategic role of a CFO in leveraging data to shape business decisions. He also touches on a commonly underestimated aspect of modern life–the need for genuine human connection.Show LinksConnect with Mohit Daswani on LinkedInConnect with Andrew Seski on LinkedIn Explore ThoughtSpot's data analytics solutions

Have you ever wondered what the future of car-sharing looks like?Turo CFO Chuck Fisher unpacks this with host Andrew Seski on this episode of The Modern CFO Podcast. Chuck also shares his perspective on the role of trust in car-sharing technology, the economic value created on Turo's platform, and how Turo is bridging the gap in transport insecurity.Listen in as Chuck shares his most memorable pit stops and detours along Turo's journey, including the company's rapid growth in 2021. From the role and impact of his mentors, to scaffolding platforms, hear Chuck’s route to the CFO seat and how Turo is using data-driven decision-making to create a more sustainable and equitable transportation system.Show Links Connect with Chuck Fisher on LinkedIn Connect with Andrew Seski on LinkedIn Find your drive with Turo

Jessica Holscott didn’t always have a clear route to a public-facing C-suite role. She had spent many years in different industries — from lighting to vehicle manufacturing — transitioning through a variety of positions to become the well-rounded businesswoman she is today.Most recently, she served as executive vice president (EVP) and chief financial officer (CFO) of WarnerMedia Studios & Networks. Prior to that, Jessica held several leadership roles, including EVP and CFO at HBO, senior vice president of investor relations at Time Warner, and CFO of NBCUniversal’s TV Stations division, where she brought a wealth of experience and knowledge in financial management, strategic planning, acquisitions, and more.In this episode of The Modern CFO, Jessica talks with host Andrew Seski about the playbooks that guided her throughout her career and how she transitioned into the public-facing media landscape. An avid networker with deep roots in the entertainment industry and blue-chip consumer companies, Jessica also shares invaluable lessons for aspiring CFOs seeking mentorship.Show LinksConnect with Jessica Holscott on LinkedInConnect with Andrew Seski on LinkedIn

For Townsend Search Group, executive search is a highly personalized process—one that requires looking at the market, the competitor environment, and the culture of the client’s organization, and then drawing up a tailored strategy for them. The goal isn’t just to find candidates. Rather, Townsend aims to place change-making leaders that fulfill long-term goals, influence strategic plans, and impact decision making across client organizations.In this episode of The Modern CFO,​​ Dan Ellis, Managing Director at Townsend Search Group, dives into the challenges, strategies, and invaluable lessons for aspiring CFOs and those seeking effective financial leadership. With over a decade’s experience in public accounting and consulting, Dan Explores the diverse personalities, drive, and discipline that define these financial leaders. From the vital role of athletics in shaping their work ethic to the crucial balance between work and personal life, gain valuable insights into what it takes to excel in the competitive world of CFOs.Show LinksCheck out Townsend Search GroupFollow Townsend Search Group on LinkedInConnect with Dan Ellis on LinkedInConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.[00:00:00] Andrew Seski: Hello, everyone. Welcome back to another exciting episode of The Modern CFO Podcast. As always, I'm your host, Andrew Seski. Today, we're joined by Dan Ellis, managing director of Townsend Search Group, a search group based in Michigan, my home state. And for just over a decade, Dan shared his career experience in public accounting and consulting and today is connecting private equity groups or portfolio companies with the best talent there is. Dan, thank you so much for joining us today.[00:00:35] Dan Ellis: Andrew, thank you. Happy to be here and excited to chat about some topics about the modern CFO.[00:00:43] Andrew Seski: So one of the reasons I'm so excited that you're on the podcast is that we get all of these incredible insights from CFOs in their fields. And while they're all diverse, I think your perspective should be really unique and valuable to them. It's a somewhat opaque world and I know that market dynamics have severely shifted in the last few years and even last few months. Before we dive into the whole world of CFO placements and Townsend as a search group, I'd love to go back in time and learn a little bit about how you initially became interested in accounting and maybe even earlier days outside of undergrad.[00:01:20] Dan Ellis: Yeah, sure. I appreciate that. I grew up in an entrepreneurial family. My father and grandfather purchased a manufacturing company that they grew and successfully operated. So I always wanted to be a business owner and I saw accounting as a path into that. So went to Western Michigan University, got my accounting degree. After that, spent eight years in public accounting and consulting as a CPA. Towards the tail end of that, I got into M&A advisory, due diligence, transaction support. And really liked that environment, but didn't see myself being a partner in a public accounting firm. I wanted to do something more entrepreneurial where you could eat what you kill. And so I was introduced to my colleague and partner Peter Bridges at Townsend Search Group. And just came into the executive search and recruiting world with a network previously in private equity and consulting and was able to learn the operations and the process of executive recruiting and eventually become very good at executing searches, which ultimately led into more to business development and opportunities like this to meet you. [00:02:31] So our specialty at Townsend has really become working with middle-market companies, lower middle-market companies that are privately owned, most often private equity sponsored. So we do a lot of work in the private equity community, not only at the firm level or within the funds and working with the investment teams, the operating teams. We spend a significant amount of our time working within the portfolio companies, placing accounting, finance, operational executives, and leaders. So I think today, we'll spend most of the time on CFOs. And just to set the context, a lot of our focus is in the middle market with privately owned businesses. [00:03:13] Andrew Seski: Yeah, that's really helpful. Thanks for that. Yeah, I think in my mind when you're going out and engaging with a search firm maybe for the first time, you may have some hesitations and I'm curious as to when and how maybe CFO should begin the process of engaging with the search firm. I feel like the marketplace, maybe the tenure has shortened a bit in a typical amount of turnover in the C-suite in general right now. I'm curious as to when it would be most strategic to engage with search firms, understand the marketplace better, or if you should essentially always have a good pulse on the market.[00:03:51] Dan Ellis: I think it's always important to have a good pulse on the market. And this comes into a little bit of how do you develop into a CFO. And I think earlier in a career as a candidate, as an aspiring CFO, being in contact with the recruiter can really help you be more strategic with developing your skill set to be a CFO. So we can understand your background and experiences and where you want to get and try to align your interests with companies or CFOs that are looking to hire someone in those functional areas. So making sure that you're deliberate and strategic with your career development is something that a recruiter can help counsel or advise. We can give you data points on what the market holds in terms of compensation and really just help make sure that you're aware of what's out there in the market. [00:04:45] Now, if you're a sitting CFO and you're building a team, being in contact with us is very valuable because we're constantly in the market talking with folks. We know what they're making. We know what they're looking for. If we can understand the vision that a CFO is trying to drive in a business, the strategy they're trying to execute, we can find candidates or we may know candidates that align with that strategy and that vision, and therefore it creates a win-win in the fact that we're getting the candidate the technical and the experiences that they need to develop their skillset to be a CFO, but we're also helping that sitting CFO build out their team and drive what they're looking for. So hopefully, that's helpful. [00:05:34] Andrew Seski: Definitely. I mean, so you've been with Townsend for about a decade now. And the world has changed a lot and we've been through a number of economic market cycles and then the last few years have been extremely interesting. I'm curious as to how that impacts — maybe equity becomes more important in a cash-restricted business that needs to ramp up and scale. I'm curious what a search firm market environment is, like what the cycles are in the marketplace for you, maybe what the lag is, and then what it is like in our curre...

It is a real privilege to invite you to listen to this exclusive podcast episode featuring John Nickolas, the esteemed CFO of the Philadelphia Phillies since 2007. With a rich background that includes notable contributions to Philadelphia's business landscape through esteemed firms like KPMG, Safeguard Scientifics, and Internet Capital Group, John's leadership has been instrumental in shaping the success of the city's iconic ventures.In this episode of The Modern CFO, host Andrew Seski engages in a compelling conversation with John, delving into the intricacies of managing a publicly visible yet privately-owned enterprise such as a professional sports franchise. Drawing from his extensive experience, John shares veteran insights that hold relevance for CFOs and aspiring leaders alike. Don't miss this opportunity to gain valuable perspectives from a seasoned industry expert.Show Links Check out the live podcast recording on Nth Round's Youtube Follow The Phillies on Twitter and Instagram Connect with Andrew Seski on LinkedIn

As customer expectations continue to evolve, marketers must adapt by delivering more personalized, timely, and efficient communication. This is where the online marketing platform Customer.io truly shines.Customer.io enables tech-savvy marketers to engage with their customers in a more meaningful way through emails, SMS, push notifications, and more. For the fast-growing SaaS companies that Customer.io serves, this capability could translate into stronger customer relations, higher conversion rates, and increased scalability.In this episode of The Modern CFO, host Andrew Seski talks with Customer.io CFO Zhi Li about his nonlinear career path, the impact Customer.io can have within organizations, how marketers can use AI as a fractional assistant, and more.Show LinksCheck out Customer.ioFollow Customer.io on LinkedIn, Twitter, and InstagramConnect with Zhi Li on LinkedInConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.[00:00:00] Andrew Seski: Hello, everyone. Welcome back to another episode of The Modern CFO Podcast. As always, I'm your host, Andrew Seski. Today, I'm joined by Zhi Li, CFO of Customer.io. Zhi, thank you so much for being here today. [00:00:21] Zhi Li: Thanks for having me. [00:00:23] Andrew Seski: So I'd love to talk about your career progression, the route to the CFO role, your first time as a CFO in earlier companies. But before we do so, I'd love to hear a little bit of background as to what you were interested even in undergrad and some of the first roles that you had, you know, right out of Penn.[00:00:41] Zhi Li: Yeah, yeah. So maybe just a little bit of myself and then we can probably launch into different topics that would go in there. But so I was born in China and then grew up in the Bay Area and then went to Penn. You and I just chatted about like Philly, which is the city that I really love. But after Penn, I actually started my career in Canada. So I was in finance at a wireless division of a large telco called Bell Canada. And then after that, I moved back to the US. So I worked in investment banking in New York in the tech group of Credit Suisse. So if you follow banking, you know, Credit Suisse might be called UBS or First Boston later on or something like that. So that's the some of the new dynamic there. But I learned a lot during that time in banking. Worked a lot as well but, you know, on many tech M&A and IP financing deals there and also get to interact with a ton of smart, hard-working, talented people. And then after that, I actually moved to Seattle cold turkey. And the backstory to that was my wife and I were both actually in grad school in LA. When I took the job to move to New York, I made a deal with her and say, Hey, you know, we need to transfer your grad school. She's got two more years. You know, whenever you are ready to leave, I'll hold up by end of the bargain. So no questions asked. When you're ready to leave New York, then I'll go. So the time came. This is probably like seven years ago. She says she wants to move to Seattle closer to her family. And then, I picked up and go. I did not know anybody in Seattle going in. But Seattle, I — now, like it's home for me. So I love it. It reminds me of maybe the Bay Area when I was, you know, many, many years ago, you know, back in high school when I kind of grew up in the Bay Area. So but yeah. So now, I'm in Seattle. I focus on helping fast-growing SaaS companies, helping them scale. So, you know, the one of the company was Skytap, which is a Seattle-based enterprise SaaS company. And we did a number of transactions, including a Series E Round led by Goldman Sachs. And then after that, I was with MedBridge. So it was a growth P/E-backed company, and we sold the company from one growth P/E to another growth P/E. And now, I'm at Customer.io. So very happy at the momentum and everything that we have here at the company. So just really, I think, very fortunate to be part of this growing story with Customer.io. Yeah, so that's generally the work background.[00:03:07] Outside of work, I also, you know, spend time doing the alumni interview for the Penn undergrad admission, which I always find super refreshing to see the fresh applicants every year. And I've always been amazed with the quality of the applicants. And then also, I'm on the board of an organization called LCYC — Legal Counsel for Youth and Children. So we're focused on advancing the rights of our youth and children so.[00:03:35] Andrew Seski: That's a pretty incredible resume. I want to — we're gonna pick it all apart, but let's start right at your last and current role right now, Customer.io. And I'm curious to know first, what attracted you to the firm, the leadership, maybe some of the cultural ways that the firm's been building out over the last decade, and also maybe the value add of working together. I know there are a million SaaS solutions out on the marketplace today. The venture world has been in flux over the last few years. So I'd love to learn a little bit more about the firm, how you're delivering value to clients, and what got you most excited. And you've been there for about two years now, so, you know, maybe bring us back two-ish years.[00:04:19] Zhi Li: Yeah, yeah. So just a little bit about Customer.io. So we're a leading multi-product, customer engagement platform. I think today, it's actually super exciting day 'cause we have our new launch of customer data pipeline that we launched today for early access. So, you know, throughout the last 10 years or so, our core product has been the Customer Engagement Platform, where we allow tech-savvy marketers to engage with their customers through emails, SMS, and push notifications, and also in-app messaging. And now, we also allow a new product called the Data Pipelines, so we can leverage first-party data to create more unified view for our customer records. So super exciting. [00:05:00] And I think what really attracted me — with my background, I've looked at a ton of software SaaS companies and looking at like their value and their potential. I was really attracted to number one, it's founder-led. So Colin, our CEO, has been there from day one. He's got this really long-term vision, and I really kind of feel aligned with that vision. And also, we are very horizontal in terms of like our approach to our customers. So we want to partner with early tech companies. So if you're like a VC-backed early company, we want to be partnered with you early on and grow with you, and then just try to be, you know, as you kind of advance and mature as a company, we will be part of that. And so throughout that journey, we were able to provide a lot of value for you to engage with your customer. The company's also fully remote, which I find super refreshing as well. When I joined, it was just right around the COVID time, so people are like definitely warming up to that remote idea. But the company...

In the world of wealth and asset management, and the private markets in general, there is a noticeable communication gap between generations. The next generation of owners–people between the ages of 18 and 25–are prolific consumers of digital content, from Reddit threads to Spotify podcasts. For many businesses, that means adopting new technologies, broadening offerings, and finding modern ways to effectively serve clients.In this in-person episode of The Modern CFO, host Andrew Seski visits with Anthony Pastore, Head of Broadcast Communications at UBS, to chat about what his firm is doing to bridge that generation gap in communicating and investing, the role that social media and video plays in staying relevant and ahead of the competition, and the importance of having a digital approach to maintaining the massive amount of wealth transferring to the next generation in the decade to come.Show LinksCheck out UBSFollow UBS on LinkedInListen to UBS Trending on YouTube or your preferred podcast appConnect with Anthony Pastore on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.[00:00:00] Andrew Seski: I'm Andrew Seski and this is The Modern CFO Podcast. I'm thrilled today to be joined by Anthony Pastore, head of broadcasting at UBS. We're in New York. We're here together. It's a rare opportunity for me and I'm thrilled about the conversation that we're gonna have today. Anthony, thank you so much for being here. [00:00:25] Anthony Pastore: Andrew, I'm honored to be here with you and it's very rare for me to be on the other side of the table of, podcast and video interviews. Usually, I'm the one asking the questions so I actually said to my team today as I was preparing to sit with you, I was like, I'm a little nervous. I'm not used to being interviewed. I'm usually the interviewer so I wouldn't be surprised if at some point I start turning the microphone to you and saying, "Andrew, I have a few questions for you as well" so hopefully, you're prepped for that.[00:00:49] Andrew Seski: I'm happy to.[00:00:51] Anthony Pastore: Anyway, I'm really happy to be with you. This is great. [00:00:53] Andrew Seski: Excellent. Well, I think the beginning of our conversation should probably start around your early career and why we're talking today. There's a huge gap in the wealth management and asset management world between generations. We are all consuming media in a different way, which is why I'm glad to be using this medium. And I'd love to learn from you as the head of broadcasting at UBS to explain what some of the brightest minds in the world are doing to bridge that gap. So, we have a ton to cover and I hope that it's a useful lesson for a bunch of CFOs who also have to communicate across a bunch of different cohorts of people. Whether they're investors or they're your C-suite or they're part of your team, having strong communication flows in a really technical way or a technical area like finance is just invaluable when it comes to senior leadership so. [00:01:44] Anthony Pastore: Yeah, I agree with that, by the way. And it's interesting because, and once we get into it, I'll talk more about it, but I think one of the interesting things about a job like what you and I do is we have to always be thinking, you know, five steps ahead of everybody else but it's really hard to do considering the competition in the media space. But what I think is interesting is we're talking about it, like I'm sitting in a wealth management firm at UBS and that's unique to our industry specifically — to have content like podcasts and virtual events and videos and internally for our employees and externally for anybody who wants to get a glimpse of what's going on and the thought leadership from this the UBS side. But, yeah. I know I'm going off on tangents here but I know you and I are both thinking similarly like what how much competition there isn't. How do you keep on top of it and stay relevant, especially for somebody who's sitting in a CFO seat? [00:02:37] Andrew Seski: Right. And the CFO doesn't typically get called upon for many any of the — I always say on the podcast, if you want to hear the vision of the company, you go watch the Bloomberg interview with the CEO. If you want to hear how finance is actually, you know, a key role in how that innovation is created, you come back to the podcast and listen to The Modern CFO and you listen to people like Anthony who are able to share insights from, you know, unique people who have a lot of sway into how companies are financed. So, strategic finance can take forms and a lot of different ways. We were just laughing about how both of us found ourselves in this building but neither came from purely financial roles like at wealth management firms.[00:03:20] Anthony Pastore: That's right. Yeah. And I guess that's a sort of a good segue. So and as you were asking, my background is pretty colorful. I kind of came up and I say this to all the younger people who start now. I'm in my late forties. I consider myself a true Gen X-er listening to grunge music because I was depressed and sad wearing my flannels in the nineties. But coming out of college, I went to school for I was a bit of a Renaissance man, as I always say. I studied theater, I studied business administration, and I also studied speech and communications. And my father looked at me and said, "What are you gonna do with that?" I said, "I don't know but I'll figure it out." And back in those days, you know, I was starting to look for full-time work in, say, 1997. It was the tech boom was just starting. Companies were hiring and, as we know with Gen X, there were fewer of us on the planet so there were a lot more jobs than there were people to fill them. So, I got a job working early days at Smith Barney. RIP Smith Barney. What a great firm and I still obviously work with a lot of people from those days who are now here at UBS and other firms. But Smith Barney hired me to work on a stock plan services desk, and I was helping Bank of America employees exercise stock options that they were granted by being full-time employees. And I learned a lot about the business but somewhere along the way, I met a woman who said, "You'd be really good for our radio station." I said, "You have a radio station here?" And she said, "We do." And it was called at the time "Radio FCN," which stand stood for Radio Financial Consultant Network — before we started calling them financial advisors. I interviewed and the my guy who the gentleman who became my boss for the next decade said to me, "Do you have any experience with talking about finance on any kind of a medium like this?" and it was only internal content just to the employees. I said, "No." I said, "But I have a theater background and I can talk about anything." He sai...

Many small and medium-sized businesses in the country rely on a disparate range of financial services to help manage their accounts, expenses, and payments. Unfortunately, this system lends itself to time-consuming processes and inefficiencies that get in the way of growth.That’s why Rho is integrating all the financial services businesses need into one easy platform. With Rho, finance teams can view everything in one spot, scrap inefficient processes, and focus on driving value and growth.In today’s episode of The Modern CFO, host Andrew Seski talks with Rho CFO Jeremy Klaperman about how to 1) organize information systems, 2) build out an integrated data infrastructure from day one, and 3) embrace cultures of integrity from the CFO position. With decades of experience at elite financial organizations such as Goldman Sachs, D.E. Shaw, and Citadel, Jeremy expertly navigates his role as Chief Financial Officer.Show LinksCheck out RhoFollow Rho on LinkedInConnect with Jeremy Klaperman on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.[00:00:00] Andrew Seski: Hello, everyone. Welcome back to another episode of The Modern CFO Podcast. As always, I'm your host, Andrew Seski. Today, I'm thrilled to be joined by Jeremy Klaperman, CFO of Rho. Jeremy, thank you so much for joining me today. I'm excited to talk. [00:00:23] Jeremy Klaperman: Thanks so much for having me. Really excited to be here. [00:00:26] Andrew Seski: So, Jeremy, you've spent most of your career across some of the most storied investment firms, from Goldman to D. E. Shaw to Citadel. But this is your first foray into the CFO role. I'd love to hear a little bit about what it's been like over the last six months crossing this chasm. [00:00:45] Jeremy Klaperman: It's been great. It's something that I've been looking forward to doing and planning for a while. And I think of my 20 years in investment banking and investment management as training for this because I either advised or invested in companies from all regions, from all industries, many different market cycles, whether it's the original tech bubble burst of the early 2000s to the global financial crisis to COVID. And I've had so many reps speaking with CFOs and CEOs. I've built up a great playbook of what I think best practices are and also pitfalls to avoid from everything from high level strategy to accounting to operations. And what I try to do with that is bring that to bear in my current role. And so, I view the last 20 years as kind of giving me the best practices and building up to what I'm doing now.[00:01:40] Andrew Seski: So, can you tell us what Rho is and what the future of frictionless finance means to you? [00:01:47] Jeremy Klaperman: Absolutely. So, Rho provides a wide range of financial services as well as spend management software to small and medium businesses. And a lot of our clients, almost all the small and medium businesses in the country have a disparate range of providers currently that give them all these things. They might have a bank, a credit card company, an investment firm that helps them manage their treasury and their cash. They might even have a FX transfer provider if they do a lot of international business. So, they could have two, three, or four providers of financial services. Increasingly, companies are using software on the spend management side for things like tracking expenses or automating bill pay and accounts payable. So, they could have one, two, three providers on the software side. They have all these disparate systems that don't work well, don't talk to each other, and it creates a lot of manual processes, errors, inefficiency. And the finance teams end up spending a huge amount of time just trying to do basic tasks rather than controlling their finances well, gaining strategic insights, running the business. So, what we do is we take out the entire stack on the financial side and the software side with one integrated all-in-one solution that's very easy to use and the entire finance team can centrally control and command the finances. [00:03:10] Andrew Seski: So, was this something that was important to you prior to joining? Were these inefficiencies something that you were able to identify, you know, on the other side of the table as an investor as well?[00:03:20] Jeremy Klaperman: Well, you can often identify the output or the symptoms of these, which is you're speaking to a CFO or CEO, you ask them what a key question is on the business, and they don't clearly have at their fingertips what you would think would be an important insight or just an important piece of knowledge. And that often comes from the data and the systems in the company not being well configured. So, having your key financial services and software services all-in-one integrated solution is one step, but not the only step you need to provide your management with the right information to run the business well.[00:03:57] Andrew Seski: So, I wanna talk a little bit about, you know, using some of these tools yourself as a CFO for the first time now and sort of what that foray looks like. I am so lucky to have a really, really unique subset and cohort of guests on the show. Some come from banking. Some come from, you know, Big Four and audit. Some, you know, were in the Navy or the military. And it's really interesting to see, you know, kind of a career progression that lands somebody in this financial leadership role. And would love to discuss, you know, you said your entire career was basically training for this opportunity. Did you always see it that way? Or is this new role something that you took a long time to consider, kinda a different risk profile and really different environment? Or has it been kind of a natural progression of your career? [00:04:46] Jeremy Klaperman: Over the last decade, I've become more and more interested in it. At least for me, when I graduated from school, I didn't know exactly what I wanted to be. I knew the kind of skills I wanted to learn and what I enjoyed doing, so I went down this path. And I think it's, after working with companies for so long, what I wanna do was not be an outsider or an advisor or an investor for a portfolio, but really get in on the inside; have a portfolio of one company where I'm on the team that's driving the growth, creating the value. So, it was really a natural evolution over the last 10 years where I determined that this is what I want to do.[00:05:20] Andrew Seski: I'm curious to know if you have kind of a definition of what you'd consider a modern CFO. I think everyone is really interested in general in some of the firms that you've worked at. I mean, they're, you know, the household names of Citadel or Goldman. It must be really interesting to have some of those unique experiences and learning from some o...

So much of the purchasing for tech startups and small businesses is online. Yet they often struggle to pay for the services and platforms they need because they don’t have business credit cards.This problem is especially acute for startups that lack credit as they’re more likely to have a hard time securing financing from banks than startups with good credit scores. FinTech giant Brex seeks to address this problem by supplying startups with the banking stack they need to scale.In today’s episode of The Modern CFO, host Andrew Seski talks with Brex COO & CFO Michael Tannenbaum about how Brex empowers startups, the global nature of startups, how he thinks about growth in different market cycles, and more.Show LinksCheck out BrexConnect with Michael Tannenbaum on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.[00:00:00] Andrew Seski: Hello, everyone. Welcome back to another exciting episode of The Modern CFO Podcast. As always, I'm your host, Andrew Seski. Today, I'm thrilled to be joined by Michael Tannenbaum, CFO of Brex. Michael, thank you so much for being here. [00:00:21] Michael Tannenbaum: Thank you for having me.[00:00:23] Andrew Seski: So, today, I'm excited to talk about a myriad of topics, including leadership, rise to the CFO, what excited you about Brex. So, we've got a ton to cover today and I kind of want go back in time to leaving undergrad and kind of your first roles. It's always interesting to hear kind of how people cut their teeth, whether it's in finance. We've had a number of CFOs who actually went into, you know, service first and others who started in, you know, the typical Big Four. So, I'd love to go kind of hear about your early career and, you know, walk us through the rise to your position today.[00:00:58] Michael Tannenbaum: Sure. Thank you for having me. I actually wanted to be an economist when I was in college. But my thesis advisor at school thought that academia would be not a good fit because I was too commercial and I enjoyed working a lot and, you know, in that profession, not that they don't work a lot, but, you know, you have summers off and there's a lot of lifestyle benefits to being part of university and he didn't think that those would resonate with me as much. So, he had pointed me into investment banking, which obviously was something I was aware of. And my research was heavily on like housing markets and mortgage. And I went into the Financial Institutions Group at JPMorgan in investment banking. So, banks, insurance, mortgages, all those kind of companies. And it was an interesting time 'cause I graduated from college during the GFC and, you know, banks were going under or being bought and sold. And so, I started in regulated financial services, M&A. And then I worked in a private equity company out in San Francisco where I focused largely on financial services also. And then, I went to a company called SoFi, which is now a public company, and I joined there relatively early, about 75th employee. And I kind of worked my way up through that company, starting in the capital markets team, and then took on additional roles, ran the mortgage business, which was kind of a nice round trip from my undergrad. And then, I was the chief revenue officer there. I met Henrique and Pedro at Brex. They were just coming up with an idea at the time. They were, I think 20 years old, and I was 29 or so, maybe 28. And they compelled me to come and join them as the first employee of Brex. So, that's how I got here. And I started as a CFO, and I always say this, but since it's a podcast about CFOs, I think it's even more relevant. My dad, who's also a CFO, always said to me when I joined, you know, "You're the CFO of a three-person company. It's kind of like being the CFO of nothing. So, you can call yourself chief if you want but." So.[00:03:05] Andrew Seski: Before we go back into Brex, I'm kind of curious. Do you think that sitting across the other side of the table on the investment side was informative or, you know, gave you some perspective as to what it's like to be, you know, more of an operator on the private company side?[00:03:18] Michael Tannenbaum: I think when you're just starting in your career, you look at the senior-most people that you see, at least I did. So, for me, that would be like the heads of the groups that I worked for or some of the senior people and the clients. And you ask yourself like, do I want to be that person, you know? Is that a role model for me? And I think, for me, I definitely gravitated more towards, I was always excited by, you know, the banker that had gone and became a CFO. I think that was a path that I wanted pretty quickly. And I, you know, as I mentioned, I kind of grew up with that, so it seemed very natural and attractive to me. [00:03:57] Andrew Seski: So, for everyone who doesn't know, I mean, I know I remember earlier days of learning about Brex, but, you know, now, I think you've got an incredible brand and it's very well known. But for those who are just learning about Brex for the first time, can you give us a bit of a summary of what was exciting to you first to make the leap to be that early?[00:04:15] Michael Tannenbaum: I think like a lot of good companies, you know, you start in a very specific niche and then expand out. There's a lot of, I didn't go to business school, but there's a lot of, you know, academic textbooks about business that talk about that, you know, crossing the chasm, etc. concept. And I think Brex when I joined it was really focused on startups and this need in the market for a credit solution and really a payment solution for startups. So much of the purchasing for technology companies is online, right? You can't buy Google Ads, for example, or Amazon Web Services without a credit card. They don't give small companies net 30 payment terms. You just have to pay on card. But at the same time, you have all these, you know, certainly at least 50% foreign entrepreneurs that are trying to start tech companies with a couple million dollars in the bank and can't get a credit card. And so, that was like a very hair on fire problem for that segment. And we really doubled down. And that was the Brex that I joined. [00:05:17] But the promise that I signed up for was always that credit card and expense management together would be more powerful than them separate, meaning that, you know, at SoFi when I was responsible for determining who got credit cards for example and expense management reporting as part of being the VP of Finance, it was such a challenge to wrangle everybody and get these receipts and ensure that there was spending controls. And so, with the broader promise that I think Brex has now realized, which is that you can combine expense management software and corporate card payment services in a way that is more powerful than either of them separate has proven to be true. And I think that's where, you know, Brex has moved and really defined this catego...

Private assets have traditionally been accessible only to large institutional investors and venture capitalistsBut that’s quickly changing, thanks to investment platforms like Fundrise.Fundrise is an online real estate investment platform with over 300,000 active users. Through Fundrise, everyday investors can access real estate markets and deals that they normally would not have been able to invest in on their own.In today’s episode of The Modern CFO, host Andrew Seski speaks with Fundrise CFO Alison Staloch about the democratization of private markets, alternative asset management, investor communications and transparency, and more.Show LinksCheck out FundriseListen to Onward, a Fundrise ProductionSubscribe to The Distance Newsletter, a Fundrise PublicationConnect with Alison Staloch on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.[00:00:00] Andrew Seski: Hello everyone and welcome back to another episode of The Modern CFO Podcast. I'm your host, Andrew Seski. Today's episode highlights one of my favorite topics again: thoughtful democratization and access to alternative investments. I know you've heard me discuss secondaries and venture funds with Aman and Andrea, regulating accreditation and the history of Reg CF with Woodie, even angel investing with Oslene. But today, I'm thrilled to take another approach at this topic, which is so important and so critical at this time, with Alison Staloch, the CFO of Fundrise. Alison, thank you so much for being here. [00:00:43] Alison Staloch: Thanks for having me, Andrew. Super excited for the conversation. [00:00:45] Andrew Seski: So could you give us a quick overview of Fundrise? I know it's actually the largest direct-to-investor real estate platform in the US today. Is that right? [00:00:54] Alison Staloch: Yeah, that's right. So Fundrise is a FinTech company with a mission, a really broad mission, of building a better financial system for individuals. But today, that means alternative asset management, primarily focused in real estate, really with the idea of giving everyday people access to the private markets that they were historically excluded from whether due to lack of scale, lack of wealth. And in that mission, we've built a capital-raising machine founded in regulatory excellence that allows us to scale thousands of individuals' investments to then utilize capital deployment technology to compete for alternative assets with the Blackstones and Starwoods. And with the launch of our venture capital fund and now with the Sequoias of the world, we have about three and a quarter billion in equity AUM offered exclusively through diversified portfolios. And our goal right now is to disrupt the private markets by using technology and new approaches on old industries to give outsized returns back to investors. [00:01:52] Andrew Seski: So I really like this approach and we're gonna go into the nuances of risk/reward investment profile for the differences between institutional investing and retail. But I'd like to go back in time first because you are a relatively recent CFO and in this industry. So I know you cut your teeth in the world of finance at KPMG, so Big Four experience. I want to take a minute to discuss your early career. And I think that sometimes people think that Big Four audit or accounting background is a qualification for a direct route to a CFO position, but you also worked at the SEC. So I want to kind of balance some of these, the regulatory knowledge that you have and some of the experiences that you had that are gonna make you and continue to allow you to be a really successful impact engine at Fundrise. [00:02:41] Alison Staloch: Yeah, so I joined Fundrise as CFO last year, so 18 months in the making. I've been a CFO for a whole 18 months. Like you said, prior to that, I was in audit, I was at the SEC. I was in a policy-oriented regulatory role as the chief accountant for the Division of Investment Management, which is the division that regulates registered investment companies and registered investment advisors and sets policy for them. And I think that that background has been particularly important for Fundrise. We have kind of a business built on regulatory discipline and that's been a huge differentiator for us, really has set us apart. I always joke like, oh, we literally chose to play in like, all of the securities laws, not just like one of them. And whether that's Regulation A+ or the 40 Acts, I think the structure that we've built requires a ton of regulatory compliance and discipline for a company of our size and for really kind of a startup to deal with. And we've focused on that regulatory excellence within the organization since the beginning, innovating within the regulatory requirements. I think within Regulation A+ we're, I think we're the biggest user and the most successful operator in that regulation. [00:03:53] And so, that comfort with the compliance and the regulatory discipline was one reason that I felt comfortable moving to Fundrise from the SEC. But obviously, my background is heavily, heavily accounting. And when you think about finance, it's obviously much broader than that. I think it makes sense for Fundrise and where we are. But certainly as we look to the future, we'll want to focus on hiring finance team members with different backgrounds that complement my background.[00:04:23] Andrew Seski: Yeah, it almost seems like we're teasing out your definition of a modern CFO, so we could really, we could start there as well. I think that we get an overwhelming amount of guests who just argue that CFOs, the new breadth of responsibilities has really changed, especially today, whether it's, like you just mentioned, hiring, human resources, being a leader that attracts other team members from more diverse backgrounds and keeping them engaged. The retention I think is a huge issue right now in the churn of employment. So, really curious as to what you think. Even though it's been 18 months, these have been a pretty volatile and unique 18 months to take on this leadership position. So, really curious to hear it from your perspective. [00:05:05] Alison Staloch: Yeah, so I think there's two things I'd mention. Maybe one more kind of like a mantra or approach to being a CFO today. And second, what I think is really important for a mission-oriented business like Fundrise to consider when hiring a CFO. So the first one, I think it's that you have to be constantly evolving. The CFO role is constantly changing, but what I mea...

Crypto investors have seen their fair share of sudden market meltdowns this year. This week, all eyes were on FTX, formerly one of the world’s largest cryptocurrency derivative exchange platforms.This latest turmoil has sent shockwaves throughout the industry. Yet historically, cryptocurrencies have rebounded following each crisis. What doesn’t wipe out the blockchain becomes a hard lesson for crypto ventures, turning them into fortified iterations of themselves.For Brett Royer, CFO of Fidelity Digital Assets, the recent unraveling of FTX underscored hard lessons that are not unique to crypto. An expert in high-level financial planning, Brett says those lessons point to fundamental business principles that have long existed.In this episode of The Modern CFO, Brett talks with host Andrew Seski about decentralized finance, the role of trust within the increasingly digital world of finance, how he thinks about risk, and more.Show LinksExplore crypto careers at Fidelity! Browse Open PositionsCheck out Fidelity Digital AssetsConnect with Brett Royer on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.‍[00:00:00] Andrew Seski: Hello everyone and welcome back to The Modern CFO Podcast. As always, I'm your host, Andrew Seski. I'm thrilled for the episode today because we are joined by Brett Royer, who's head of finance at Fidelity Digital Assets. Brett, thank you so much for being here today. [00:00:19] Brett Royer: Andrew, thank you for having me. [00:00:21] Andrew Seski: So, we're going to dive right in. The world of crypto and the world of digital assets has evolved in a unique way, down to literally the hour, especially this week. So, I want to kick off not just on the current event side, but we're going to have plenty of time to go through those current events, I want to start today actually with your career and then kind of the history of Fidelity Digital Assets, which I know spans back farther than most institutional groups had even considered labs themselves. So, we'd love to kick off with maybe some of your educational background, sort of the rise to this position, and then we'll segue in and out of how Fidelity Digital Assets is positioned today and what you're thinking about today. So, we have a lot to cover. [00:01:08] Brett Royer: Yeah, sure. Great. So, I'll start with a little bit of career history. Prior to business school, I'd say one of my more substantial roles was working in the Merrill Lynch Private Banking and Investment Group. So, there I was working with a former Chicago Board of Trade trader who had sold a business, a trading business, for a substantial sum, thought he was going to retire and ride off into the sunset. I spent some time doing some personal things and then realized that he got bored. And so, went back into business as a wealth manager and he ran his own proprietary trading strategy for a lot of the clients that he served. And so, I joined his team as sort of a mini fund analyst of sorts that supported the portfolio analysis and trading decisions behind the proprietary strategy that he used on behalf of his clients. And so, that was a really great experience. I think there, I kind of developed my first set of background and skills in capital markets, gained a pretty good understanding of how the markets work, traded in some illiquid securities and got a sense for what that was like. And had a pretty interest, I was there at a relatively interesting time. [00:02:33] So, I was probably in my second or third year, I can't remember exactly which, when things started to go wrong in Wall Street in financial services, right? So, the history is Lehman goes bankrupt and then Bear Stearns comes about as close as you can get to bankruptcy. And then I remember distinctly going into the weekend, Merrill Lynch was next up as a potential firm that was looking at having liquidity challenges and potentially could go under. And I'm sitting there as a junior analyst and just sort of watching this from an interested perspective, but also from the perspective of like, my job was on the line. But at that point in time, I didn't have as much to lose. Obviously pretty early in my career. But nonetheless, I think it was a strenuous time for everybody. And I distinctly remember sort of being glued to the TV all weekend just waiting to see what would happen. And then, sure enough, Bank of America, acquires Merrill Lynch on Sunday and I was really lucky to have a team that supported me, and I was able to maintain my role throughout then. But learned a lot of hard lessons around what bear markets feel like and look like. And I think that's in part educated some of what I've seen and felt in crypto markets as well. And I think just giving me a little bit of perspective on not getting too lost in the moment, either up or down, right, and having an understanding that these things tend to be cyclical, right? And there are going to be ups and downs and you don't want to get too over indexed on either side of the equation while you're in the moment, which is really hard.[00:04:08] But from there, I decided I didn't want to be a financial advisor. I think that would've been the next move if I stayed there. And that group worked with $10 billion clients and above. And so particularly difficult prospecting or particularly difficult segment to prospect in a serious way if you're a 25-year-old. So decided anyway that I wanted to be on more of an analytical track and more of a CFO track anyway, so made sense to go back to business school and sort of pivot. And so, I went to the University of North Carolina, got my MBA there. And around that time, Fidelity had just started recruiting at the University of North Carolina for a financial leadership rotational program. And I'm from Massachusetts originally, so familiar with Fidelity. Really wanted the chance to get back to the Northeast and so jumped at the opportunity to join a program that is tagging itself as developing the next future CFOs of Fidelity business units. [00:05:05] So did that. And the idea is you get broad exposure to the firm in relatively short order, right? You do six-month rotations in four different parts of the firm. And then you graduate, and you come out and Fidelity really has a sort of continuous career rotational program aspect to it, even after you're out of that traditional rotational program as well. So after I graduated, I spent the majority of my time, five years or so, in a role in our Fidelity institutional business. So, it's a really interesting business for Fidelity. They provide custody for registered investment advisors and then clearing for correspondent broker-dealers as well. And I worked on the broker-dealer side of the business. And up until 2008 or so, Fidelity was the clearing provider for a couple of large firms, JPMorgan and Bank of America. And around that time, they lost both in a year as a result of JP Morgan buying Bear Stearns and then Merrill, Bank of America buying Merrill Lynch. And so, both had self-clearing capabilities that sort of made them take away the need for a clearing pr...

Raising capital can be a tedious process, even after investors have agreed to commit capital. This realization was the catalyst for experienced Bay Street lawyers Mat Goldstein and Rebecca Kacaba launching DealMaker—a digital transaction management platform that provides a seamless, headache-free investor experience. Since the platform’s inception in 2018, companies of all sizes have used DealMaker to launch and market their offerings to investors across the globe.In this episode of The Modern CFO, Mat talks with host Andrew Seski about the future of digital capital formation and what sets DealMaker apart from other cloud-based platforms offering capital raising solutions.‍‍Show LinksCheck out DealMakerConnect with Mat Goldstein on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInTranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.‍[00:00:00] Andrew Seski: Hello everyone and welcome back to The Modern CFO Podcast. As always, I'm your host, Andrew Seski. Today, we're joined by Mat Goldstein, co-founder of DealMaker. Mat, thanks so much for being here. [00:00:20] Mat Goldstein: I'm delighted to be here. Thanks, Andrew. [00:00:22] Andrew Seski: So before we kick off, let's talk about DealMaker and what it is. What does it mean to turn a simple capital raise into e-commerce?[00:00:30] Mat Goldstein: Yeah. DealMaker, first and foremost, is a technology company. Our platform is used by issuers. You know, think, when I say "issuers," think "founders." You know, companies who are raising capital, who are looking to solve an age problem of how to engage with prospective investors and turn them into a source of capital. Using our software, an entrepreneur can start an online store and run a full e-commerce campaign, identify leads, create a relationship with a community, engage with that community to turn it into a source of capital, and rely on the analytics, payment processing, and full set of functionalities you'd expect in a Shopify store. You can leverage that for a capital raise campaign. So that's what we mean by turning raising capital into e-commerce. It means using the internet as your medium of sale and using the tools of e-commerce to identify an audience, engage with it, and turn that into a source of capital. [00:01:38] Andrew Seski: So let's talk about how you identified the need for DealMaker and what actually catalyzed the entrepreneurial spirit in yourself to go start something new. You were a lawyer in your previous life. So now, are there no efficiencies when it comes to the legal frameworks of startups? Because I'm sure between all of the different types of offerings, whether you're doing Reg CF, Reg A, Reg A+, and having all of these actually change a bit probably over the last 10 to 20 years between the US and Canada, did you notice any major inefficiencies that catalyzed your, you know, desire to go try to solve some with technology?[00:02:16] Mat Goldstein: Well, Andrew, that's what we lawyers would call a leading question. You're right. So look, you know, Rebecca and I started this company back in, you know, back when we were still practicing law early kind of 2017. We did our beta in 2017. We started planning the company earlier in 2016. We were both partners at an international law firm. And in our daily practice, we dealt with technology companies and we came to understand that kind of lean startup mentality of how to solve a problem using technology by build-measure-learn. And we, you know, one day, we sat down with a whiteboard and we mapped out what the steps were in a capital markets transaction. [00:02:58] And when I say "capital markets transaction," I really just mean a company selling shares, right? And it's crazy. I mean, you have to identify, there are eligibility requirements when you're selling chairs in the exempt markets. I can get into all that. It's like, you know, you've got public companies who are listed on stock exchanges. They have a whole infrastructure to raise capital, and it's automated, and it's built on, you know, brokerage houses where you go into your Robinhood account and you press "buy" or "sell." And, you know, technology takes over. The private markets have nothing like that. Just nothing. If you and your co-founders were raising capital, which, you know, you've done so you can talk about, then you're in the exempt markets. You're not a public company. You don't have access to that infrastructure. So you need a lawyer to draft a subscription agreement. The investors have to be eligible to buy exempt market securities, which means they need to be accredited in some way or the offering needs to be qualified in a different way. They'll need to fill in the certificate, they'll need to send in the money, the money they send in has to match the order on the form. And there's a whole nine depth, you know, kabuki dance to get to a closing, which just costs everybody time, money, and headaches. [00:04:15] And so, we looked at that and said, "Well, isn't raising capital really just sales?" Right? And that's something you and I have chatted about before. Isn't it just sales? How is it different? You're identifying somebody who, you know, likes what you have. You've got an ideal profile in mind and you wanna eliminate any friction in between them liking what you have and, you know, you making the transaction. And so, there's a playbook for this. It's called the internet. And if you think back to the early days of e-commerce, you had shoe stores who would go to like Accenture and custom-build a website to sell shoes online. And along came Shopify and said, "You don't have to do that anymore. We built a platform. You can license an online store and it has everything you need to run a campaign on the internet and you have to find the buyers." That's the Shopify model. And that's our model as well. [00:05:20] And at the end of the day, there's just some stuff you can't outsource or automate. If you are a founder, it's you that people are investing in. You have to be front and center of your store. But we built a technology platform that puts the issuer front and center, puts the founder front and center, and going out to raise capital then becomes an exercise in, you know, e-commerce, right? Identifying the prospects, engaging with them in a way that, you know, speaks with them, that they connect with, using analytics to see who's likely to close, right? All of the tools of the modern kind of sales funnel management — the CRM, the prospecting, the elimination of friction in getting an order form signed, elimination of friction in taking payments online using credit card — we built all of that. [00:06:10] And over time, it became, you know, something that, I think it's true whenever you introduce innovation into a market, there's a dynamic, right? The market response, the innovation, and it unlocked people's minds. So in the very early days, right, there were, you know, people who were raising capital from friends and family and from kind of pre-IPO rounds and following the same steps that traditional capital raising would follow. But over time, as people came to really und...

Financial management can make or break a business. Any business undertaking attempted without taking cost drivers, growth prospects, and value realization goals, among other critical factors, into account is leaving a big, wide door open to problems.Jack Boyles, Managing Director at Marcum LLP, understands this perfectly well. With his extensive experience in financial planning and modeling, valuations, and funding strategies, Jack keeps a trained eye on both the micro and macro factors that influence today’s rapidly evolving financial services sector.In this episode of The Modern CFO, Jack talks with host Andrew Seski about critical factors to consider for growing companies, how he deals with the unexpected, and the valuable lessons he learned over his 25-year-long career as founder, investor, and CFO of several companies.‍‍Show LinksCheck out Marcum LLPConnect with Jack Boyles on LinkedIn or via emailCheck out Nth RoundConnect with Andrew Seski on LinkedIn‍TranscriptPlease note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.‍‍[00:00:00] Andrew Seski: Hello everyone and welcome back to The Modern CFO podcast. As always, I'm your host, Andrew Seski. Today, we're joined by Jack Boyles. Jack, thank you so much for being here. [00:00:19] Jack Boyles: Thank you. I'm looking forward to our conversation. I reviewed a number of your other podcasts. They're all great and I learned something in each one.[00:00:25] Andrew Seski: So today, Jack serves as CFO at Marcum. Jack's based in Boston and has been a CFO across a number of industries and is insatiable when it comes to learning new things, trying new industries. [00:00:38] But one of the things that we've been talking about, maybe ad nauseam, but between us is the idea that maybe there is a certain time and place where CFOs can have their biggest impact at, you know, either a type of financing, an industry, and maybe CFOs shouldn't necessarily grow across all stages and all different types of industries. Maybe they should be specialized and maybe there is a time and place for that CFO who can drive the most value. [00:01:05] So this is a topic I really want to dive into and really dig our teeth into because Jack has such a unique vantage point, serving his entire career really honing in on this idea. So Jack, I got to turn it over to you to tease out some of the value and insights here on sort of that topic and whatever else we can foray into across all of the experiences you had as a CFO.[00:01:26] Jack Boyles: Thanks for the great introduction. Yeah, I'm not CFO of Marcum — number one. Marcum has a group of consulting CFOs and so I now work with roughly a half-dozen small and medium-sized companies as a fractional CFO. Prior to that, I've been CFO of a number of companies in which I was founder, investor, angel, and always had a CFO title in a wide variety of verticals — distribution and logistics, software manufacturing, IT services, natural resources. [00:01:57] And right now my portfolio includes a SaaS company — a company working on carbon credits with blockchain — and another marketplace for health services. So, you know, it's a pretty broad spectrum and I've enjoyed it because there has been a number of learning opportunities. [00:02:14] But returning to your theme, I found I'm really good at the five million to 50 million-dollar service orientation companies. And I've realized that that's where I can add the most value. I'm not somebody who can take a company public, although I've sold a number of companies to Fortune 500 companies. But it's really recognizing there are different skill sets for those by both vertical and by size of company, if you will, the capital intensity and sort of the economic structure underlying the business.[00:02:45] So I can break down those and, you know, they're all interesting problems, but it's really a different skill set for each one of them. And you need to manage differently as that, you know, financially-oriented team member. [00:02:58] Andrew Seski: In terms of where some of this interest comes from from my end is the fundraising environment over the last few years dramatically changing in the last few months. So what may have been, you know, a company doing five to 10 million then that could have been valued, and maybe in the software land, maybe even at a hundred X multiples at one point, just an absolute crazy valuation and fundraising environment to, you know, a very, very immediate, almost shift in going from, you know, pure growth orientation to conservative cost cutting, you know, headcount reduction. And I think the question there stems not only just from where the CFO can be the most valuable in their niche and their competency, but also how to weather the volatility of different market cycles. [00:03:42] And there are a lot of variables to play with here so I really like your answer that the CFO can be really valuable by identifying their impact in a niche due to all of the other market environments and volatility in the markets that could, you know, shift strategy and financial strategies that a company may pursue.[00:03:58] Jack Boyles: Well, you're shining a spotlight on, you know, certainly what is the most critical thing for growing companies, which is, do they have access to capital? And is it the right capital on the right terms and in the right timing? You know, obviously, you progress from family and friends to seed rounds, to Series A and up. [00:04:17] But it's really more important, or the starting point for that analysis is really, what's driving the need for cash? Is it building your organization? Is it financing working capital? Is it plant and equipment expansion? Is it building relationships that you need to invest in? So really understanding from a, what I would call a fairly granular level, what are the cost and capital drivers in your business and really internalizing that, that economic, that, you know, the calculus of the business, because that's gonna tell you what kind of capital you need and where to go knocking on the door. It's seldom the case that you're gonna be the first guy knocking on that door, but making sure that they understand your economic model is critical.[00:04:59] And so to narrow your field down on who you're focusing on and what you're offering and making sure, I mean, whether you look at PitchBook or anything else, it's fairly easy to qualify those people and what their investment criteria are. Most firms are very upfront about what they invest in and there's nothing wrong with reaching. But there's also economy and wisdom and finding people who've done your deal before with like competitors because they understand it. They get it. Whether you consider that investor a bank or a venture capital or a family office, find people who have done it before. They're gonna bring more knowledge to the deal — in the one they do because they are always seeking to be better. Their due diligence will be a lot more efficient and helpful...