The Best Interest - Complex Personal Finance Made Easy

Jesse is solo, answering your questions! Kate, a government worker with $650,000 in IRAs, is wondering how she can best rebalance her portfolio - and when. Dan seeks clarity on bonds' role despite recent poor returns, learning they offer portfolio stability and mitigate market volatility, critical for risk-averse investors. Peter asks about Social Security timing, highlighting the trade-off between early claiming's investment growth potential versus the guaranteed, low risk returns of delayed benefits, with traditional advice favoring security. Lucas, a young investor with a taxable brokerage account, asks about key considerations to include when setting up a dividend reinvestment plan. Lastly, Chris wonders how to judge between three potential advisors. If you’d like a question in a future AMA, send Jesse a message!   Key Takeaways: • How to mitigate your risk by diversification. • Why a 10% “sandbox” could be the right thing for your portfolio. • Should you employ a time based or an allocation based  rebalancing strategy. • When you should or should not use bonds. • What is “transfer-on-death”? • How to choose between financial advisors.   Key Timestamps: (00:00) - Review of the Week (01:15) - AMA: Portfolio Rebalancing (10:45) - AMA: Understanding Bond Performance (20:29) - The Role of Bonds in Inflation (25:59) - AMA: Social Security and Investment Strategy (29:37) - Understanding Risk-Adjusted Returns (30:32) - Comparing Social Security to Risk-Free Investments (32:37) - Potential Downsides of Early Social Security Collection (37:39) - Lucas's Taxable Brokerage Account Strategy (50:38) - Chris's Financial Advisor Dilemma   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Tax Loss Harvesting Myths, Debunked: What You Need to Know Now, The Simple 3-Step Formula to Avoid Excess Taxes in Your Investments, Is Splitting Your Portfolio Between Advisors a Smart Move? Maximize Your Capital Gains: Proven Tax Strategies for 2024, How to Avoid IRS Fines: The Urgent 90% Rule You Need to Know   Mentions: “Why Can’t I Take Social Security Early and Invest It?”  https://bestinterest.blog/why-cant-i-take-social-security-early-and-invest-it/  “I Wouldn’t Know Where to Start” – 16 Questions to Ask A Financial Advisor https://bestinterest.blog/financial-advisor-questions/    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse’s running the show solo this week, bringing with him some interesting perspectives on tax tricks, whether you should rent or buy, and college education. In this episode, you’ll hear why side hustles might just be a waste of time, what makes detailed budgeting overrated, and how you’re actually spoiled just by having a queen sized bed! This episode is great if you’re looking for a few reminders, grounding advice, or a few different opinions. Key Takeaways: • Reasons why you shouldn’t rely solely on your stocks for your early retirement. • The 50% Rule for 529 College Savings Plans. • What makes a side hustle a waste of time? • Why renting might be the right decision. • How perspective shows you’re actually spoiled! • Is your advisor a professional? Or a hack? Key Timestamps: (02:51) Critique of the FIRE Movement (05:50) Debunking Tax Hacks (09:08) The 50% Rule for 529 Plans (13:22) Primary Home: Not an Investment (15:18) The Reality of Side Hustles (19:41) Rent vs. Buy: A Balanced View (25:21) Living a Life of Luxury (32:10) Reevaluating Detailed Budgeting (36:52) The Spectrum of Financial Advisors (41:38) Pay Yourself First, But Not Too Much (42:50) Essential Thoughts for True Wealth (46:02) Conclusion and Final Thoughts Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance Mentions:Factfulness: Ten Reasons We're Wrong About the World--and Why Things Are Better Than You Think by Hans Rosling, Anna Rosling Rönnlund, and Ola Rosling “I Wouldn’t Know Where to Start” – 16 Questions to Ask A Financial Advisor by Jesse Cramer 11 Essentials of Client Service More of The Best Interest:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

What are the long-term gains of educated investment decisions? The COVID pandemic triggered fear and uncertainty, with many wanting to sell everything amid the stock market's 30% drop. However, disciplined investors maintained their perspective and followed their investment policy. This approach, coupled with proper financial planning, often results in a stronger portfolio after market crashes, helping investors avoid costly mistakes. In contrast, a friend who sold his business for $10 million was initially hesitant to invest in the stock market due to a lack of education, but with advice to seek higher yields and follow a well-planned asset allocation strategy, he increased his earnings from 0.05% to 4.5% annually. Throughout Jesse’s monologue, he highlights examples where educated, deliberate, and disciplined decisions helped grow people’s portfolios and prepare them for their long-term goals. Joe Saul-Sehy of Stacking Benjamins, returns to the podcast for the second half of the show. Jesse and Joe each brought 5 questions to ask before retirement - ideally long before retirement. Alternating, back and forth, they discover how few of these questions are about money. Sound investment and retirement planning isn’t just about the number going up, but also about what you’re going to do with the money you accumulate. Many of us plan to enjoy plenty of golfing during retirement, but, who among us can say we’d like to golf every day for 20 years? Join Jesse and Joe on an exploration of the questions you need to ask when planning your retirement.   Key Takeaways:• Have you taken your mental and physical health into consideration when planning your retirement years? • How long do you expect to be retired? And what do you plan to do with your time? • Find something you can passionately be involved in during your retirement years. • Why “chasing kids” isn’t a great retirement plan. • How to simplify your savings plan and make the most of it. • What engineers can teach us about planning for the unknown unknowns.   Key Timestamps:(02:14) - Jesse’s Monologue: Putting a Dollar Sign on Financial Planning (07:23) - Car Loan Decision Making (08:24) - Backdoor IRA Contributions (10:11) - Choosing the Right Home Location (14:01) - Understanding Cash Balance Plans (20:48) - Interview: Joe Saul-Sehy (22:08) - Top Questions for Retirement Planning (37:40) - Creative Solutions for Health Insurance in Retirement (39:20) - Behavioral Aspects of Investing (41:26) - The Fee Wars and Financial Planning (45:36) - Asset Allocation and Investment Choices (48:45) - Health and Healthcare in Retirement (53:05) - Maintaining Relationships in Retirement (57:46) - Protecting Yourself in Retirement (01:01:06) - Giving Back to the Community (01:07:58) - Conclusion and Podcast Information   Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, retirement lifestyle, FIRE lifestyle, mental health, physical health   Mentions:Website: https://www.stackingbenjamins.com/ LinkedIn: https://www.linkedin.com/in/joe-saul-sehy-b3426b31/ What Retirees Want: A Holistic View of Life's Third Age by Ken Dychtwald and Robert Morison Keys to a Successful Retirement: Staying Happy, Active, and Productive in Your Retired Years by Fritz Gilbert   More of The Best Interest:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse opens the show by sharing a personal anecdote about a former teacher's challenging investment choices, which were burdened with high fees from their financial advisor. He emphasizes the predatory nature of the financial advice teachers receive, encouraging teachers to seek better investment options from reputable firms like Vanguard and Fidelity. Finally, Jesse underscores the importance of being informed against the systemic issues in the retirement planning landscape for educators. Dan Otter joins for the second half of the show. Dan is the co-founder of 403(b)Wise, which aims to make information about the 403(b) readily available to educators. Together, Dan and Jesse delve into the complexities and challenges of 403(b) retirement plans for public school teachers. They address the absence of Federal fiduciary protections, the prevalence of predatory financial options, and the stark differences between high-cost and low-cost providers. This episode features valuable resources, including Otter's book Teach and Retire Rich and the 403(b)wise website, offering practical advice on avoiding high fees and poor investment choices.  Whether or not you are a teacher, you’ll find this episode full of valuable education. And, be sure to share this with friends and family members who are teachers. Key Takeaways: • Be on the lookout for financial predators who’ll lure you into high fee accounts. • The 403(b) is a great tool for your retirement. • There’s a lack of federal fiduciary protections which allows for school teachers to be taken advantage of. • How 403(b)wise is helping educate teachers on their best financial options. • What to do if you’ve already invested your money in a high fee account. • How sales agents are incentivized to harm teachers. Key Timestamps: (02:17) Jesse’s Monologue: Teachers Are Getting Taken Advantage Of (03:51) Advice for Teachers (09:24) Introducing Dan Otter and 403(b)wise (11:51) The Problem with 403(b) Vendors (18:03) Annuities in 403(b) Plans (24:12) Wise Consumer Tips for Financial Products (25:28) Understanding Fixed Income and Annuities for Teachers (27:46) The Ethical Dilemma of Financial Advisors (31:48) Advocacy and Resources for Teachers (37:11) Navigating 403b and 457(b) Plans (42:47) Conclusion and Final Thoughts Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, teachers, teacher finances, 403(b), 403b, 457(b), 403(b)wise Mentions:Website: https://403bwise.org/ LinkedIn: https://www.linkedin.com/in/daniel-otter-ph-d-0380a61/ Mentions: Teach and Retire Rich:  https://amzn.to/4dQloRi Ten Rules for Retirement Investing: https://www.youtube.com/watch?v=_ewjha6cu1M https://www.nytimes.com/2016/10/23/your-money/403-b-retirement-plans-fees-teachers.html https://www.nytimes.com/2018/03/16/your-money/403b-annuities.html More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

Today, Jesse helps us step out of our financial frame and see the broader context of our lives. Quoting from David Foster Wallace’s “This is Water” speech, he highlights our self-centered bias and makes suggestions on how we can gain greater perspective through the support of those around us. In his monologue, Jesse also notes Charlie Munger’s belief that the world isn’t driven by greed, but rather by envy, and that often our reality seems a certain way because of what we see around us. Steve Adcock joins the conversation to share his own perspectives on financial independence, early retirement, and, perhaps most importantly, finding meaning in both. Previously featured on episode 16 of The Best Interest, Steve provides us with a bit of an update on his FIRE journey since retiring at just 35 years old. He gives us a taste of the quippy insights he shares weekly through Millionaire Habits and delves into some of the mental health considerations that should come along with our financial goals, sharing how he and his wife have been able to inject their financially independent lives with purpose and meaning. If you’re looking for some practical advice around the basics, mental health, and the power of passive investing, this is the episode for you. Key Takeaways:• What is your “frame” and how can people on the outside help us see our realities for what they are? • Mentors, friends, or others in your network could help you step out of your frame and see your financial situation in a new light. • How to change your lifestyle with your financial situation to maximize every moment. • The smart shopping habits to adopt that’ll set you miles ahead of most people. • Why the basics aren’t overrated and are worth revisiting regularly. • Why you need to plan for not just getting to retirement, but also what comes after. Key Timestamps:(01:38) Understanding Your Frame of Reference (03:29) David Foster Wallace's Insight on Self-Centeredness (05:04) The Role of Envy in Personal Finance (12:51) Interview with Steve Adcock: Achieving Financial Independence (20:38) Lifestyle Changes and Financial Strategies (25:50) The Power of Passive Investing (29:50) Adjusting Spending in Retirement (31:38) Evaluating Subscriptions and Spending (37:45) The Importance of Financial Basics (40:59) Finding Purpose in Retirement (50:46) Millionaire Habits and Final Thoughts Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, retire early, financial independence, digital nomad, millionaire habits, financial basics More from Steve:Millionaire Habits: https://millionairehabits.us/ Website: https://steveadcock.us/ LinkedIn: https://www.linkedin.com/in/steveallenadcock/ Twitter: https://x.com/SteveOnSpeed Mentions: Millionaire Habits: How to Achieve Financial Independence, Retire Early, and Make a Difference by Focusing on Yourself First by Steve Adcock The Best Interest Podcast, Episode 16, “Retire at 35 with Steve Adcock” https://open.spotify.com/episode/6lhHT4r7aNfrjwVVqKL3ha?si=c00ca0f26e934a2a Mimetic Desire and Consumer “Choice” by Katie Gatti Tassin https://bestinterest.blog/frame/ More of The Best Interest:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Back with another AMA, Jesse tackles your questions on employee stock incentives, diversification, how taxes affect investments, and more! Our first question comes from Lynn, who asks about when to take Social Security, which opens up a broader discussion on optimal timing for retirement benefits. While she and her husband initially planned to wait until age 70 to maximize benefits, based on family longevity, Lynn’s making some reconsiderations. Key considerations for anyone approaching Social Security include health, family history, need for benefits, ongoing work plans, spousal benefits, and how Social Security fits into their broader financial plan.  Yogi is considering his company's Employee Stock Purchase Plan (ESPP), which offers a 5% discount but no look-back provision. While it may seem like "free money," he's concerned about missing other investment opportunities. Key factors include market risk, taxes, and the risk of holding too much company stock.  Jacob and his wife, both 32, have diversified investments across various accounts, including sector-specific funds and broader options like S&P 500 and international funds. Jesse dives into ideas on how to diversify investments into a variety of asset classes, sectors, and geographies. Maple Leaf is turning 65 and plans to apply for Medicare, asking whether the income lookback period for IRMAA (Income-Related Monthly Adjustment Amount) is a one-time event or reviewed annually. The lookback period is annual, with a two-year delay, meaning income from two years prior determines the surcharge. Jimbo from Alabama asks whether the fiduciary standard is a sufficient filter when choosing financial advisors. While being a fiduciary is important, as it requires advisors to act in their clients' best interests, it’s a "coarse filter," and clients should dig deeper by asking about advisors' payment structures, investment philosophies, and potential conflicts of interest.  Our last question comes from Eric. Eric, 38, plans to retire at 55 while his wife intends to work until 65, raising the challenge of coordinating their financial and lifestyle transitions. Jesse emphasizes the importance of clear communication about how their daily routines and relationship dynamics might change as one partner retires while the other continues working If you’d like a question in a future AMA, send Jesse a message! Key Takeaways:• When you want to take out Social Security depends greatly on your health (current and anticipated), personal needs, work plans, spousal benefits, and more. • How do ESPPs work? And how can you make the most of these employee offers? • How to diversify your investments into a variety of asset classes, sectors, and geographies. • What is IRMAA? And how can you make the most of it? • Just like when you look for a doctor, a therapist, or any other professional help, you’ll want to ask a series of questions to find out how they work and if it’s a good fit. • How to balance your retirement plans with your spouse’s. Key Timestamps:(00:00) - Introduction and Featured Review (01:47) - Family History and Social Security (12:54) - ESPPs and Taxes (21:21) - Investment Diversification (29:06) - IRMAA and Lookback Periods (37:41) - Questions to Ask Potential Advisors (45:57) - Lifestyle Transitions to Retirement Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, IRMAA, ESPP, Income-Related Monthly Adjustment Amount, Employee Stock Purchase Plan, ask me anything, early retirement, capital gains tax   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog When Should I Take Social Security?:  https://bestinterest.blog/when-should-i-take-social-security/ Contact me at jesse@bestinterest.blog The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse explores the intricacies of student loan forgiveness, highlighting the fallacy that loans can simply vanish without consequence. He argues that the financial burden ultimately falls on taxpayers and critiques the notion that the U.S. government can "magically" eliminate student debt. Jesse explains the Public Service Loan Forgiveness (PSLF) program and how student debt exacerbates mental health problems. He proposes a balanced approach of partial interest forgiveness to alleviate borrower burdens, shorten repayment periods, and benefit both individuals and the government, all while maintaining personal accountability. Today’s guest, Katie Gatti Tassin, is the founder of Money with Katie, a platform she created in 2020, which was later acquired by Morning Brew. During the interview, Jesse and Katie discuss frustrations with the American healthcare system, underscoring how flawed incentives impede rational decision-making. Most of the conversation revolves around financial literacy and misconceptions among the FIRE community and broader society. As Jesse and Katie reach the end of the discussion, they share their thoughts on how social media and social isolation affect us financially and mentally.  This is a wide-ranging conversation with a few insightful tangents. If you’re looking for a personal, real, and thoughtful finance podcast, then this is the episode for you. Key Takeaways: • Loan forgiveness doesn’t make the loan disappear… Someone is eating that cost. • Jesse explains how the Public Service Loan Forgiveness (PSLF) program works. • The broken incentives of the American healthcare industry discourages rational decisions. • How “tough love” online finance personalities like Dave Ramsey or Caleb Hammer work (or don’t). • How our individualism and social media lead to social isolation and affect our mental health. • If you’re listening to this podcast, you’re probably more financially secure than you think. Key Timestamps: (01:38) Jesse’s Monologue: Student Loan Forgiveness & Moral Hazards (20:37) A Proposed Solution to Student Loan Debt (27:06) Introducing Katie Gatti Tassin (28:46) The Healthcare Marketplace Dilemma (38:23) Hospital Fines and Perverse Incentives (40:13) Balancing Savings and Enjoying Life (47:42) Tough Love in Personal Finance (51:26) Building Community and Financial Implications (58:18) Social Media's Impact on Mental Health (01:11:01) Conclusion and Resources Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Money with Katie, Morning Brew, Katie Gatti Tassin, American health care, student loan forgiveness, student debt, Public Service Loan Forgiveness, PSLF Mentions: Website: https://moneywithkatie.com/  LinkedIn: https://www.linkedin.com/in/katiegatti/  More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Referring back to his article, Fundamentals Of Retirement: Is the Summit “Good Enough?”, Jesse uses an experience hiking in the Adirondack Mountains as a metaphor to explore retirement preparedness. He recounts how being poorly equipped for a challenging hike can mirror the pitfalls of entering retirement without thorough planning - you might reach the summit, but the journey and destination may not be as enjoyable. Sharing the example of a couple, John and Eva, who are on the brink of retirement with substantial assets and a solid financial plan, Jesse raises critical questions about their investment strategy, withdrawal plans, and tax considerations, suggesting that while they are well-positioned, their retirement journey could be smoother with additional preparation. For today’s interview, Jesse is joined by Rob Berger. Rob is a contributing editor for Forbes Advisor, host of the Financial Freedom Show, and author of “Retire Before Mom and Dad: The Simple Numbers Behind A Lifetime of Financial Freedom”. He founded Doughroller.net in 2007, a popular personal finance blog that attracted millions of visitors. With a background as a litigation attorney, Rob is now a prominent voice in retirement planning, providing valuable education through his YouTube channel and other platforms. If you’re looking for quality retirement finance tips, no matter where you are on your journey, this is a great episode for you!   Key Takeaways: • Preparing for retirement allows you to enjoy the journey and the destination (just like hiking!). • Learn about key aspects of retirement planning, such as investment strategy, withdrawal plans, and tax considerations, and the need for comprehensive preparation. • What is the “Retirement Income Death Spiral”? And how can we avoid it? • How does inflation and stock market conditions really affect your retirement savings? • How to take a conservative approach to Social Security and still have cautious optimism about the future. • Why you should not focus on individual stocks when planning for retirement!   Key Timestamps: (02:10) Jesse’s Monologue: Retirement Planning Fundamentals (05:47) John and Eva's Retirement Scenario (13:09) Interview with Rob Berger (14:00) Understanding the Retirement Income Death Spiral (15:55) Inflation and Retirement Planning (23:40) Social Security Concerns and Assumptions (25:48) The Future of Social Security and Political Solutions (27:24) The Importance of Diversified Income in Retirement (29:26) The Role of Cash and Bonds in Retirement Portfolios (34:21) The Emotional Side of Market Volatility (39:26) Common Financial Mistakes and How to Avoid Them   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Rob Berger, Retire Before Mom and Dad, Social Security, retirement account mistakes   Mentions: Website: https://robberger.com/  YouTube: https://www.youtube.com/@rob_berger  LinkedIn: https://www.linkedin.com/in/bergerra/  Mentions:  https://bestinterest.blog/reaching-the-summit-retirement/  Retire Before Mom and Dad: The Simple Numbers Behind A Lifetime of Financial Freedom How Much Cash Should You Hold In Retirement?   Should Cash Replace Bonds in a Portfolio? How to Avoid the Retirement Income Death Spiral?    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

In today’s opening monologue, Jesse explores the concept of Sequence of Returns Risk, a crucial and often misunderstood threat to retirees, by illustrating how poor returns early in a retirement can severely impact long-term stability. He emphasizes the importance of diversification. Jesse then introduces the idea of path dependence, drawing parallels to the life of author Philip K. Dick, whose posthumous fame underscores the significance of a journey’s path, not just the journey’s outcome. Jesse connects this to investing, explaining how the sequence of returns can greatly affect an investor’s experience, despite the long-term average returns. Using "Sally the Investor" as an example, Jesse highlights the emotional and psychological challenges of navigating market volatility, reinforcing the need for resilience, understanding short-term unpredictability, and the benefits of diversification in long-term investing. Tyler, the creator of Portfolio Charts, joins Jesse for the second half of the show. His site is known for its innovative financial tools and insights. Tyler, a fellow engineer with a passion for finance, blends technical expertise with creativity to clarify complex investing concepts. In their discussion, Tyler and Jesse explore critical retirement topics, including the safe withdrawal rate and sequence of returns risk.. Tyler introduces the concept of engineering tolerances for managing financial variability and discusses strategies like variable withdrawal rates. He explains the "flowing nature of withdrawal rate math," illustrating how safe withdrawal rates change with longer retirement periods. If you’re looking for some evidence based, long term thinking in your DIY financial life, then this is the episode for you!   Key Takeaways: • How poor returns early on can negatively affect my retirement. • What is “sequence of returns risk”? And how can I create a financially resilient situation for myself? • Diversification into a variety of financial vehicles is key to the long term success of your portfolio. • Path dependence, illustrated by Philip K. Dick's posthumous fame, emphasizes that the sequence of returns can greatly affect investment outcomes. • What are “safe withdrawal rates”? And how can traditional average return calculations be misleading?   Key Timestamps: (01:07) Jesse’s Monologue: Understanding Sequence of Returns Risk (07:50) Mitigating Sequence of Returns Risk (08:35) Path Dependence: Lessons from Philip K. Dick (13:16) Sally's Ride: A Real Example of Path Dependence (22:57) Investment in Knowledge: Path Dependence (25:28) Understanding Safe Withdrawal Rates and Sequence of Returns Risk (35:05) The Importance of Consistent Portfolios (47:29) Tyler's Personal Finance Journey and Portfolio Charts (51:01) Conclusion and Listener Engagement   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Tyler from Portfolio Charts, path dependence, sequence of returns risk, safe withdrawal rates Mentions: Website: https://portfoliocharts.com/ Mentions: https://portfoliocharts.com/charts/withdrawal-rates/#chart https://portfoliocharts.com/2016/12/09/perpetual-withdrawal-rates-are-the-runway-to-a-long-retirement/ https://portfoliocharts.com/charts/retirement-spending/ https://portfoliocharts.com/portfolios/permanent-portfolio/ https://bestinterest.blog/path-dependence/   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

In today’s AMA, Jesse delves into various financial dilemmas and strategies to maximize benefits and secure a stable retirement. The first question comes from Mindy, a 50-year-old widow, weighing the pros and cons of remarrying due to its potential impact on her survivor benefits. Jesse explains the complexities of Social Security spousal and survivor benefits, urging listeners to consult with a Certified Financial Planner to navigate the intricacies and optimize their benefits. Then, Bob seeks Jesse’s advice on whether to use retirement savings to pay off a mortgage on a new home. With $1.2 million in retirement savings and plans to retire in five to ten years, Jesse takes into consideration some additional context to make some suggestions. Of course, any financial planner or advisor will answer unknown questions with “it depends” - we need to know all of someone’s financial “puzzle pieces” before we can put that puzzle together. Jesse then addresses Tad's query on compound interest and its application to stocks, bonds, and stock funds, clarifying the concept of "compound growth" in investments and the benefits of reinvesting profits. Our penultimate question is from Dan, a retiree who shares his bond-avoidant investment strategy, relying on pensions and CDs for market downturns. Jesse discusses the potential risks if Dan passes away, affecting his wife's income, and suggests considering a small bond allocation. Last up is Amy's question about setting up an annuity from a 401k to create what some might call a “retirement paycheck”, prompting Jesse to caution against high fees and sales tactics associated with annuities, recommending traditional investment portfolios for better returns, flexibility, and liquidity. If you’d like a question in a future AMA, send Jesse a message!   Key Takeaways: • Consult a certified financial planner to navigate the complexities of Social Security spousal and survivor benefits, especially when considering remarriage. • The most common answer to finance questions is “It depends”. It depends on your city, your state, different tax rates, your income, your relationship status, your goals. There is no one size fits all solution. • Understand that "compound growth" is a more accurate term than "compound interest" for investments like stocks and stock funds, with reinvested profits accelerating growth. • Bonds can be a useful asset in your investment strategy, but of course, it depends on your goals and life situation. It’s important to consult with a CFP to get a more complete picture. • Be cautious about setting up an annuity from a 401k due to high fees and sales tactics; traditional investment portfolios often offer better returns, flexibility, and liquidity.   Key Timestamps: (00:00) - Introduction (01:49) - Social Security and Survivor Benefits Explained (09:46) - Financial Planning for Retirement and Mortgages (19:34) - Understanding Compound Growth vs. Compound Interest (25:49) - Dan's Retirement Strategy (27:59) - Evaluating Risks in Retirement (32:51) - Amy's Annuity Question (36:29) - Comparing Life Insurance and Annuities (42:46) - Immediate Fixed Annuities (47:08) - Conclusion and Final Thoughts   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, annuities, compound interest, compound growth, death of a spouse, prenup, mortgages, ask me anything   Mentions: https://bestinterest.blog/valuing-social-security-as-an-asset-in-your-retirement-plan/  https://bestinterest.blog/how-much-life-insurance-do-i-need/  https://open.spotify.com/episode/2NMGr6vYPT4KuCdu9txoce?si=41789317e9614367     More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog  Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse starts by sharing two of his blog posts in today’s monologue.  The first post, “The Answers are Here, But…”, expands on William Gibson’s quote, “The future is already here. It’s just not evenly distributed, yet.” Jesse draws a connection between Gibson’s quote and the distribution of financial literacy, explaining that The Best Interest is part of the distribution effort. Of course, there are those who distribute bad, or even dangerous information, leading into the second half of the monologue, “How to Avoid Frauds and Ponzi Schemes”. Jesse offers 3 ways we can avoid being taken for a ride.  Today’s guest, Rachael Camp, is a Certified Financial Planner (CFP) specializing in helping solo business owners, offering services with her own business, Camp Wealth, and educating people through YouTube, her blog, social media, and more.  Their discussion centers around recognizing scams and debunking myths circulated on social media, calling out fearmongers, and offering helpful insight into the financial tools available to solopreneurs.  Importantly, Rachael notes what an LLC is, why an entrepreneur may - or may not - want to register one, and who they should consult before making that decision.    Key Takeaways: • How to find the answers you’re looking for. • Keeping a lookout for scams - and finding people who’ll help you watch! • Social media and the myths perpetuated thereon. • What is a stock option? • What is a solopreneur? And what financial tools are at their disposal? • Should you register as a corporation? What kind?   Key Timestamps: (01:20) Jesse’s Monologue: The Answers Are Out There (06:47) Avoiding Financial Frauds and Ponzi Schemes (21:41) Introducing Rachel Camp: Solopreneur Wealth Builder (23:11) Debunking Financial Myths with Rachel Camp (30:30) The Reality of Social Media Investment Strategies (31:17) Understanding Options: A Primer (33:52 Exploring Options Trading Strategies (36:54) Critiquing Robert Kiyosaki's Financial Advice (43:50) The Rise of Solopreneurs (46:31) Business Structures and Tax Considerations (51:04) Debunking Tax Hacks and Financial Myths (54:39) The Importance of Financial Literacy and Caution (1:00:41) Conclusion and Final Thoughts   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, solopreneurs, LLCs, business structures, incorporation, Robert Kiyosaki   Mentions: Website: https://www.rachaelcampwealth.com/  LinkedIn: https://www.linkedin.com/in/camprachael/  Mentions:  https://bestinterest.blog/the-answers-are-here-but/  https://awealthofcommonsense.com/2023/06/the-evolution-of-financial-advice/  https://bestinterest.blog/how-to-avoid-frauds-and-ponzi-schemes/  https://x.com/camp_wealth  https://www.youtube.com/@CampWealth/videos    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

Jesse begins today's episode with two reflections. First, he talks about the rarity and preciousness of gathering all your loved ones in one place. While money is important, it is ultimately a means to gain the freedom to spend time with those you care about. In his second reflection, Jesse recounts the story of his parents' neighbors' house catching fire, highlighting the importance of risk management and preparedness, such as having smoke detectors and emergency plans. This underscores the idea of using money wisely to enhance life’s quality and maximize meaningful experiences with loved ones. Today's guest, Andy Hill, is the founder of Marriage Kids and Money, an award-winning YouTube channel, blog, and podcast that offers actionable advice for family financial independence. As Jesse and his wife raise their first infant child, Andy provides invaluable insights on the importance of emergency funds, baby items, healthcare, life insurance, and more. He delves into the essentials of family financial planning, enabling us to enjoy more time with the people we care about most. If you’re thinking about what matters most in life and how smart financial planning can help you get there, then this is the episode for you.   Key Takeaways: • Money matters because of the freedom it allows. • How to prepare for crises. • The cost of childbirth, diapers, and a whole lot of other things. • How to deal with financial stress as a family. • Preparing your family financially for the worst. • Simple tips and tricks for new parents.   Key Timestamps: (02:28) Jesse’s Monologue: The Value of Time with Loved Ones (07:45) A Financial Cautionary Tale: House Fire (19:45) Introducing Andy Hill: Family Finance Expert (20:29) Preparing for the Costs of Childbirth (24:42) Real Estate Considerations for Growing Families (27:37) Emotional Impact of Financial Decisions (29:45) Navigating Parenthood, Career Choices, and Savings (38:59) Practical Tips for New Parents (44:25) Life Insurance and Estate Planning for New Parents (52:31) Conclusion and Resources   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York financial planning, financial stress, emotional attention, family financial advisor, family finances, marriage kids and money, Andy Hill, estate planning, the finances of children   Mentions: Website: https://marriagekidsandmoney.com/  LinkedIn: https://www.linkedin.com/in/andyhillmkm/  Mentions:  https://bestinterest.blog/you-just-go/ https://bestinterest.blog/house-fire/  https://bestinterest.blog/foxes/)  https://open.spotify.com/episode/0JVTRYN8HBrgTI4EhVZglk?si=26185de5a5704a06 https://open.spotify.com/episode/1ox7hbv5uhG3bHsIzf2Cfk?si=8da95ab3e144443a  https://waitbutwhy.com/2015/12/the-tail-end.html    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

Jesse starts this episode with a confession: money still stresses him out. The four ways that Jesse reduces this stress are remembering what’s going right financially, prioritizing spending, working hard, and remembering that others have walked this path.    Then, with another call back to his blog, Jesse invokes Marshall McLuhan’s quote “the medium is the message” when sharing from his post, “The Friction is the Message”.    Today’s guest is Carl Richards, the creator of the Behavior Gap, author of The Behavior Gap: Simple Ways to Stop Doing Dumb Things with Money, and host of Behavior Gap Radio. Not only has Carl been featured on Oprah.com and Forbes.com, he’s the creator of the Sketch Guy column which ran weekly for a decade in The New York Times. In this episode, Carl gives us some great insight into how we can refocus ourselves and our finances on what really matters to us.   If you’re interested in not only financial planning, but time, energy, and attention planning, too, then this is the episode for you!   Key Takeaways: • 4 ways Jesse reduces his financial stress. • Friction as a bad thing, and friction as a good thing. • Why you should invite imposter syndrome in. • What is the Behavior Gap?  • How to choose your financial advisor. • How to manage your money, time, energy, and attention.   Key Timestamps: (02:10) Jesse’s Monologue: Money Still Stresses Me Out   (07:24) Managing Financial Stress: Four Key Reminders   (13:42) The Friction is the Message   (22:14) Carl Richards Joins the Conversation   (28:48) Why Carl Shares   (30:41) Overcoming Fear, Anxiety, and Imposter Syndrome (39:02) The Behavior Gap in Investing   (44:48) The Value of Real Financial Planning with a Real Advisor (52:28) Conclusion and Resources   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York financial planning, financial stress, human capital, personal energy, mental attention, financial advisor, imposter syndrome, financial anxiety, the Behavior Gap, the Friction is the Message   Mentions: Website: https://behaviorgap.com/  LinkedIn: https://www.linkedin.com/in/thinkingcarl/  Mentions:  https://bestinterest.blog/money-still-stresses-me-out/  https://bestinterest.blog/the-friction-is-the-message/  https://bestinterest.blog/selling-and-surviving/ https://behaviorgap.com/radio/  https://www.50fires.com/    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse begins today’s episode with a short monologue on the highs and lows of money. Can money buy happiness? Or are they uncorrelated? Either way, money can certainly buy flexibility and optionality. Jesse collects insights from Thom Yorke, Matthew Killingsworth, Danny Kahneman, and Angus Deaton.   Today’s guest is Jonathan Clements, the founder and editor of Humble Dollar, the author of My Money Journey and How to Think About Money. Clements spent nearly 20 years at the Wall Street Journal as their lead personal finance columnist. He shares why we need financial goals that fulfill us, why he plans to continue working, and how we can plan financially for retirement, but why that shouldn’t be the end goal of our financial journey.    If you’re interested in long-term financial planning that will set yourself up for success, then this is the episode for you!   Key Takeaways: • How to strike the balance between spending and saving. • Why you can never know what you’ll really want in the future. • We need personal fulfillment goals, not just financial goals. • Jonathan’s retirement plan is ICE over FIRE. • How to invest not only for retirement, but also for your heirs’ inheritance.   Key Timestamps: (01:54) Jesse’s monologue: Can money buy happiness? (09:15) Introduction to Jonathan Clements (10:30) My Money Journey (12:40) Switching from saver to spender (15:50) We can’t predict the future (21:43) 8 traits successful people have in common (24:25) ICE: I’ll Continue Earning (28:46) Annuities and Social Security (36:29) Setting the next generation up for success (44:40) Close   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York financial planning, immediate fixed annuities, lifetime income annuities, equity and indexed annuities, Roth IRA, Social Security, retirement wealth planning   Mentions: Website: https://humbledollar.com/  Jesse’s Radiohead article:  https://humbledollar.com/2024/05/happy-conclusion/ LinkedIn: https://www.linkedin.com/in/jonathanclements/  How to Think About Money:  https://amzn.to/3yHtlth My Money Journey: How 30 people found financial freedom - and you can too:  https://amzn.to/3Kw91NO   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

On today’s episode, we bring you something a little different. Jesse’s collected a series of questions from newsletter subscribers and will answer them in today’s AMA (Ask Me Anything). Jesse answers into which accounts young people should be putting their money. Other questions answered are: Is getting to your “Coast FI” a good idea? How to balance which accounts you’re putting money into and how your goals might change that. How can you financially prepare for parenthood? Why you should diversify your investments, even if your lack of diversification is working for you. What are “Roth Conversions”? And how can we make the most of tax diversification? If you’re interested in hearing Jesse’s answers to these questions, then this episode is for you. If you’d like a question in a future AMA, send Jesse a message!   Key Takeaways: When should I put money into my Roth IRA vs. my Traditional 401k? We don't know the future. So, diversify. What Jesse’s doing to prepare financially for parenthood. How clear goals can get you more specific guidance when financial planning.  When and how you can do “Roth Conversions”.   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse starts this episode discussing his “50/50 rule” of college savings. Jesse also talks about 529-to-Roth conversions (why they’re overrated!), the FAFSA, and other financial tools at our disposal for college planning.    Evan Giokas then joins the show to dive deeper into a college admissions conversation. Evan is the founder of The College Confidence Coach, which helps students through their higher educational journey. Evan covers what a “conative assessment” is,  how to be cost-conscious when preparing for college, how to start college conversations with your child, and the importance of showing your values to college admissions staff..   If you’re preparing a child for college, this is the episode for you!   Key Takeaways: How to start the college conversation with your child  What is the Conative Assessment?  What is the college money pit trap? How to be cost-conscious in college planning How to optimize your FAFSA The “50/50 Rule” for college saving The pros and cons of 529–to-Roth conversions   Mentions: 🌐 Website: https://www.thecccoach.com/  👉🏼 LinkedIn: https://www.linkedin.com/in/evan-giokas-56443746/  📚 The Important Details Behind 529-to-Roth Conversions: https://bestinterest.blog/the-important-details-behind-529-to-roth-conversions/ 📚 Follow the 50/50 Rule for College Saving: https://bestinterest.blog/the-50-50-rule-for-college-saving/ 📚 University of the People: https://www.uopeople.edu/    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

In episode 79 of The Best Interest Podcast, host Jesse Cramer discusses the intricate relationships between health, wealth, and time with guest Phil Pearlman. Jesse starts with his usual monologue, explaining and establishing that health, money, and time are all interchangeable resources that many people trade-off throughout their lives. Jesse and Phil then delve into how health decisions significantly impact financial standing and overall quality of life, emphasizing the importance of viewing health as an investment in one's future. Phil, transitioning from a finance profession to focusing on personal health, shares his insights on behavioral finance, the importance of making conscious decisions regarding health and finance, and the impact of societal trends on individual well-being. Additionally, Phil discusses his unique approach to personal health, advocating for self-experimentation and critical thinking in navigating health advice. The conversation also touches upon cultural aspects of addiction and the power of individual choice in improving one's health, wealth, and time. Finally, Phil shares information about his work at the Pearl Institute and his dedication to helping people make better health and life decisions.   Key Takeaways: How physical health is a critical aspect of financial health. Health will allow you to enjoy your wealth. Phil’s holistic approach to health and how it includes finances. Why you need to imagine yourself in the future. How to see your future self as a real person, and consider their needs. Why you should be a scientist and your most important subject! You don’t have to be a statistic.   Mentions: 🌐 Website: https://www.pearlinst.com/  🌐 Prime Cuts Newsletter: https://primecuts.substack.com/  👉🏼 LinkedIn: https://www.linkedin.com/in/philip-pearlman-1002183/  📚 Rebels with a Cause by Phil Pearlman: https://primecuts.substack.com/p/rebels-with-a-cause  📚 Fahrenheit 451 by Ray Bradbury: https://amzn.to/3xHyaSF 📚 Brave New World by Aldous Huxley: https://amzn.to/3U7W55j 📚 1984 by George Orwell: https://amzn.to/3U5e2Bu 🎥 The film Fahrenheit 451, on Vimeo  https://vimeo.com/433467090   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse starts this episode with an engaging monologue: how exactly does The Best Interest generate revenue? Jesse answers this question and asks YOU for your help in ensuring The Best Interest continues as a terrific free financial resource.    And then Justin Peters joins for the second half of the episode. Justin hosts The Struggle is Real, a podcast about adulting through your twenties. He’s also a co-founder of SimplePod Studios, which produces The Best Interest Podcast. In this episode, Justin and Jesse discuss, compare, and contrast their top five “Golden Rules” of personal finance. If you’re looking for an insightful, fun, and fast-paced conversation, this is the episode for you.    Key Takeaways: How does The Best Interest make money? The intersection of Jesse’s professional life and The Best Interest Why you need to track your money! How gift cards trick you into spending more. The best investment is in yourself. Simple is better than complex (almost always). Why and how you should prepare for risk. Why you MUST automate your finances, as much as possible. Think long term, but don’t forget the present.   Mentions: 🌐 Website: https://simplepodstudios.com/  👉🏼 LinkedIn: https://www.linkedin.com/in/justinleepeters/  🎙️ Podcast: https://www.tsirpodcast.com/  🧠 The RRTTLLU Framework: https://bestinterest.blog/rrttllu/   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Peter Lazaroff is the host of The Long Term Investor podcast and serves as the Chief Investment Officer at PlanCorp, a registered investment advisory in St. Louis. On today’s show, Jesse and Peter talk about the cognitive challenge of investing at all-time highs. It’s normal to feel like a crash might be coming; but it always feels that way, and you shouldn’t be worried about it. If you’re a long-term stock market investor and want to think a little more rationally or learn, this is the episode for you!    Key Takeaways: Why you should expect corrections and bear markets,, but shouldn’t worry about them. Why the stock market keeps going up, regardless of the political party in power. Should you continue investing when the market is at an all-time high? Why you shouldn’t be worried about what’s happening in the short run.  How the evidence cuts both ways in investing, and how to simplify it. Why you should diversify into global stocks. How to prepare for a bear market.   Mentions: 🌐 Website: https://peterlazaroff.com/  👉🏼 LinkedIn: https://www.linkedin.com/in/peterlazaroff/  🎙️ The Long Term Investor Podcast: https://peterlazaroff.com/podcast  📚 The Market Crash Is Coming! (…Eventually): https://bestinterest.blog/market-crash/  📚 “Boring” Money Topics That I Find Fun: https://bestinterest.blog/boring-money-topics-that-i-find-fun/  📚 Decades of Zero Return: https://bestinterest.blog/decades-of-zero-return/    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jared Dillian is a former Wall Street trader at Lehman Brothers, an author of 4 books, and daily writer a newsletter for financial professionals called The Daily Dirtnap. He’s sharp, witty, and brings great energy to today’s conversation. In this episode of The Best Interest Podcast, we learn about "The Allegory of the Sandwich" and how you can pay for the small stuff by thinking carefully about the big stuff! If you’re looking to hear unique takes on the FIRE movement and your daily latte, this is the episode for you!   Key Takeaways: How taxes can actually be interesting! The power of waiting (for decades) The foundational importance of cash flow Preparing for life via insurance How being smart about the big decisions will help you not sweat the small stuff. Why Jared doesn’t want to retire (ever). Why you shouldn’t make your own pizza. The Allegory of the Sandwich. Why the goal should be happiness, not a number. When is it worth it to make more money? How financial stress doesn’t necessarily depend on how much you make.   Mentions: 🌐 Website: https://www.jareddillianmoney.com/  👉🏼 LinkedIn: https://www.linkedin.com/in/jared-dillian-411aaa1b/  🎙️ BE SMART Podcast: https://www.jareddillianmoney.com/podcasts  📚 No Worries: How to live a stress-free financial life by Jared Dillian: https://amzn.to/4atCxiz 📚 The FIRE Movement by Jared Dillian: https://wggtb.substack.com/p/the-fire-movement 📚 “Boring” Money Topics That I Find Fun by Jesse Cramer: https://bestinterest.blog/boring-money-topics-that-i-find-fun/    More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog   The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.