The Best Interest Podcast

Today, Jesse is joined by Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-retirees about misleading sales tactics that exploit fear - especially the fear of market losses. They emphasize the importance of working with fee-only, fiduciary advisors who are legally obligated to act in clients' best interests, in contrast to commission-based salespeople who often obscure fees, misrepresent guarantees, and use charm to build trust. Drawing from Jason Zweig's “19 Questions to Ask Your Financial Advisor,” Jesse highlights key criteria for evaluating advisors, including transparency, credentials, investment philosophy, and service scope. They condemn opaque fee structures, sales contests, and annuity marketing tactics - like steak dinners that pressure attendees into high-commission products - and describe most annuities as complex, wealth-threatening vehicles. Jesse adds practical suggestions like inquiring about an advisor's succession plan, communication style, and client load, and stresses the value of education and evidence-based investing. The two advocate for comprehensive financial planning and alignment of advisor-client interests, with Don underscoring the importance of commitment to honesty, transparency, and fiduciary duty. Key Takeaways:• Annuity and investment salespeople often exploit retirees' fear of losing money in market downturns to sell high-fee products. • While there are niche use cases, many annuity products are expensive, opaque, and designed to benefit the seller more than the buyer. • You need to know what happens to your financial relationship if your advisor retires or leaves. • State-level oversight often fails to protect consumers from misleading practices. • Know the difference between moral fiduciary responsibility and legal fiduciary responsibility. • It's a red flag if an advisor recommends products they wouldn't use for themselves. Key Timestamps:(00:00) Understanding Annuities and Financial Advisors (02:08) 19 Questions to Ask Your Financial Advisor (08:13) Conflicts of Interest in Financial Advising (12:56) Investment Philosophy and Market Timing (18:34) Professional Credentials and Requirements (23:07) Additional Questions for Your Financial Advisor (29:05) The Gamble of Annuities (34:34) The Deceptive World of Indexed Annuities (36:17) The Ethics of Financial Advisors (39:29) The Lack of Federal Oversight (46:38) Misleading Sales Tactics (49:42) Advice for Annuity Holders and Seekers (56:45) Don McDonald's Financial Talk Show Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques Mentions:Website: https://talkingrealmoney.com/ LinkedIn: https://www.linkedin.com/in/donmcdonald/   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 education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

Jesse explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning into retirement, especially those aged 50 to 75. With half of the participants recently retired and the other half preparing to retire within two years, the study offers a timely look at the "final glide path" into retirement and the early years that follow. Authored by retirement experts Fritz Gilbert and Eric Weigel, the report dives into preparedness, lifestyle satisfaction, and evolving concerns. It reveals a common disconnect between what pre-retirees expect and what retirees actually experience—particularly around health, identity, and social engagement. Jesse discusses how meaning and purpose often decline post-retirement, and how maintaining social connection and physical health is key to thriving. Drawing inspiration from longevity expert Dr. Peter Attia, the episode emphasizes that preparing for retirement goes beyond money—it's about planning for purpose, relationships, and well-being. Jesse also shares three powerful exercises to help listeners create a more intentional retirement vision: the Perfect Day, the Ikigai Map, and the Rocking Chair Test. Key Takeaways:• Retirement is more than a financial event—it's a major life transition requiring emotional, social, and identity planning. • Physical health and vitality are crucial to enjoying retirement, not just surviving it. • Social connection is one of the strongest predictors of well-being in retirement. • The “Perfect Day” exercise helps retirees envision and plan a fulfilling daily life post-career. • The “Ikigai Map” offers a powerful framework to align purpose, passion, and impact in retirement. • The “Rocking Chair Test” encourages long-term reflection on what truly matters at the end of life. Key Timestamps:(00:00) Diving into the Retirement Perspectives and Attitudes Survey (04:22) Finding Purpose and Meaning in Retirement (10:26) Adhering to a Healthy Lifestyle (13:49) Creating a Clear Vision and Plan for Retirement (21:12) Biggest Differences Between Pre and Post Retirees Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques Mentions:https://www.retirewithpossibilities.com/wp-content/uploads/2023/05/Retirement-Perspectives-and-Attitudes-Survey-May-2023.pdf  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 education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

Jesse explores the financial journey of late starters with guest Bill Yount, co-host of Catching Up to FI. In the opening monologue, Jesse shares his “Stupidly Simple Secret Sauce” for personal finance: spend less than you earn, grow income without inflating lifestyle, invest consistently, and prioritize savings. He warns against flashy success stories, consumer culture, and speculation, instead advocating for steady, index-fund investing and disciplined budgeting. The episode also addresses market volatility and debunks the “buy the dip” strategy, showing that long-term consistency outperforms timing attempts. Bill shares his compelling story of waking up to his finances at age 50, shifting from paycheck-to-paycheck living to a 40% savings rate and near financial independence. He emphasizes emotional readiness, sustainable planning, and community support for those starting late. Whether you're in your 30s, 50s, or beyond, this episode delivers practical, empowering advice for reclaiming your financial future. Key Takeaways:• The core rules of personal finance are deceptively simple: spend less than you earn, earn more without inflating your lifestyle, and invest consistently. • Boring, steady investing (like index funds) usually beats market timing or speculative bets. • Many late starters carry emotional baggage around money, but those feelings can become fuel for change. • After the excitement of getting started, real progress is made through slow, steady work over years. • Taking full responsibility for your finances brings peace of mind, even if the numbers aren't pretty at first. • With a solid plan, cutting expenses, and investing consistently, it's doable. Key Timestamps:(00:00) The Stupidly Simple Secret Sauce of Personal Finance (04:58) The Winners are Loud, but the Losers Stay Silent (06:42) Boring is Best: The Case for Index Funds (10:46) The Story of Dave: A Financial Cautionary Tale (15:30) Market Volatility and the Concept of Buying the Dip (25:02) Facing Financial Realities with Bill Yount (29:48) Creating a Financial Plan (35:07) Late Starters and Financial Freedom (39:56) The Role of Social Security (48:51) Investment Advice for Late Starters (56:00) Building a Financial Community Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques Mentions:Website: https://catchinguptofi.com/ CUTFI's Facebook group:  https://www.facebook.com/groups/catchinguptofi/ LinkedIn: https://www.linkedin.com/company/catchinguptofi/  Mentions: https://bestinterest.blog/secret-sauce/ https://bestinterest.blog/dave/ https://bestinterest.blog/buy-the-dip/ https://bestinterest.blog/is-tax-loss-harvesting-worthwhile/   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 education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

Today, Jesse critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while promoting disciplined, evidence-based strategies. Tariffs, though intended to protect domestic industries, often raise prices and stoke inflation, ultimately harming consumers, businesses, and investor sentiment, with economists warning they may slow growth or trigger stagflation. Market reactions, such as those seen during the Trump-era tariffs, highlight investor uncertainty and the self-inflicted nature of such economic disruptions. Jesse offers 15 introspective questions to help investors stay grounded, assess their emotional triggers, and focus on long-term goals rather than panic-driven moves like tax-loss harvesting or "buying the dip." He critiques the celebratory tone around recessions and urges against using emergency funds for speculative gains, emphasizing that such attitudes overlook the human cost of downturns and risk mispricing assets. Ultimately, the message is clear: successful investing demands self-awareness, patience, and preparation—not market timing, blind optimism, or short-term emotional decisions. Key Takeaways:• Tariffs are essentially taxes on imports aimed at protecting domestic industries and gaining leverage in trade negotiations. While intended to boost local economies, tariffs often have unintended consequences, such as raising consumer prices. • Long-term investment strategies like diversification and rebalancing remain important, even during market turbulence caused by tariffs. • The "buy the dip" mentality is flawed, especially if it involves tapping emergency funds or relying on hope over planning. • Assuming “markets always recover” can lead to complacency and distorted risk-reward expectations. • Rational, emotionally detached investing leads to better outcomes than strategies based on fear or overconfidence. • Successful investing hinges on preparation and humility, not certainty or bravado—acknowledging the market's unpredictability is key. Key Timestamps:(00:00) Market Update and Tariff Discussion (02:00) Impact of Tariffs on the Market (13:33) 15 Questions for Scared Investors (22:19) Understanding Portfolio Reactions to Market Events (27:15) The Fallacy of Buying the Dip (28:48) Emotional Investing and Market Realities (36:20) The Myth of Guaranteed Market Recovery Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques Mentions:https://bestinterest.blog/the-15-tariff-questions-ive-heard-most/  https://bestinterest.blog/15-questions-for-scared-investors-right-now/ https://bestinterest.blog/let-them-trade-stocks/ https://bestinterest.blog/last-weeks-terrific-real-life-stock-lesson/ https://bestinterest.blog/impossible-to-lose/  https://bestinterest.blog/roth-conversions/  https://bestinterest.blog/is-tax-loss-harvesting-worthwhile/  https://bestinterest.blog/markets-dont-always-recover/ 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 education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.  

Jesse answers listener questions on financial planning, investment management, and retirement. He discusses the challenges of rising homeowner's insurance costs in high-risk areas, the differences between Treasuries, CDs, and high-yield savings accounts, and the inefficiencies of using life insurance for tax-free retirement. He advises Casey, a future retiree, on tax-efficient withdrawal strategies and investment choices, and guides Chris, a federal worker, on pension decisions, TSP management, and career changes. Jesse also addresses Rachel's concerns about bond funds versus individual bonds, explaining their similarities and recommending a goals-based portfolio approach with cash reserves and an appropriate bond allocation for retirement security. Throughout the episode, he emphasizes strategic financial planning and adaptability in decision-making. Key Takeaways:• Homeowner's insurance costs are rising in high-risk states like California and Florida due to natural disasters. • We explore the ethical dilemma over whether wealthy homeowners should receive government aid after disasters. • Treasuries, CDs, and high-yield savings accounts differ in liquidity, risk, and how financial institutions set rates. • Permanent life insurance strategies like whole life and indexed universal life are marketed as tax-free retirement solutions but are often inefficient. • When planning your retirement, future required minimum distributions (RMDs) should be considered, as pre-tax accounts will be taxed upon withdrawal. • Career risk should be assessed by weighing long-term benefits against short-term uncertainties, emphasizing planning and adaptability. Key Timestamps:(00:00) Introduction to Personal Finance for Long-term Investors (01:40) Question 1: California Wildfires and Financial Planning (06:57) Government Intervention in Insurance (13:21) Question 2: Treasuries, CDs, and High Yield Savings Accounts (21:09) Question 3: Tax-Free Retirement Strategies (29:46) Question 4: Retirement Planning with Part-Time Work (33:49) Pros and Cons of Realizing Capital Gains (36:06) Question 5: Federal Government Pension Dilemma (42:33) Career Change Risks and Rewards (48:46) Question 6: Bonds vs. Bond Funds Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques Mentions:Career Change – Is It A Risk?: https://bestinterest.blog/career-change-risk/ 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 Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discussion, Jesse contrasts gambling with long-term investing, emphasizing the risks of short-term market bets versus the reliability of patient investing. Christine highlights the shift in financial advice toward holistic retirement planning, including the importance of low-cost, diversified portfolios and planning for life transitions. The episode also explores the financial impact of caregiving, particularly on women, and the necessity of proactive retirement savings and long-term care planning. John Guyton's "guardrails approach" is discussed as a strategy for adjusting withdrawals based on market performance. Additionally, the conversation underscores the role of psychology in financial decision-making and the non-financial aspects of retirement, such as maintaining social connections and redefining work-life balance. The overarching message is that successful retirement planning requires a combination of careful financial preparation, behavioral awareness, and long-term strategic thinking. Key Takeaways:• Short-term stock market movements may seem random, but long-term investing historically trends upward, making it a safer and more strategic approach compared to gambling. • Many people underestimate their lifespan, which can lead to financial shortfalls in retirement; actuarial data and family history should be factored into planning. • Persuasive stories can shape financial decision-making, sometimes leading people to overlook critical advice in favor of compelling but misleading pitches. • Taking on unpaid caregiving roles can impact financial security, and couples should consider financial agreements to ensure fair distribution of assets. • Beyond finances, maintaining social connections and finding purpose are crucial for a satisfying retirement. • A successful retirement is not just about financial security but also about ensuring a meaningful and well-balanced life in later years. Key Timestamps:(00:00) Casino vs. Investment (11:09) Understanding Life Expectancy for Retirement (15:29) The Man Who Never Looked Up (20:41) Interview with Christine Benz (23:06) The Shift to Holistic Planning (23:47) Consumer Investment Preferences (24:26) Christine's Book: How to Retire (25:04) Personal Story: Christine's Parents (27:16) The Role of Financial Planners (30:24) Flexible Financial Planning Models (39:46) Retirement Planning for Women (45:28) Navigating Retirement as a Couple (47:24) Insights from The Long View Podcast (49:17) Conclusion and Contact Information Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance Mentions:Website: https://www.morningstar.com/podcasts/the-long-view LinkedIn: https://www.linkedin.com/in/christine-benz-b83b523/ Mentions: https://bestinterest.blog/how-long-will-you-live/  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 we take a look at the U.S. national debt, distinguishing it from household debt and analyzing its impact on individuals and investors. Jesse traces the debt's history and explains its structure, funding through Treasury bonds, and refinancing process. The discussion covers Modern Monetary Theory (MMT), which suggests that as a currency issuer, the U.S. cannot default but must manage inflation through taxation—though critics question the feasibility of this approach. While deficit spending can drive economic growth, excessive money printing may erode investor confidence. Interest rates play a crucial role in borrowing, investment, and market stability. Inflation, influenced by national debt and monetary policy, erodes cash and bond values, making stocks a stronger long-term hedge. Real estate may also help, but with mixed results. Despite the complexities of national debt, a diversified investment strategy and career growth offer the best approach to financial stability.  Key Takeaways:• The U.S. government operates under different financial rules than a household, as it can issue its own currency and refinance debt indefinitely. • From $75 million after the Revolutionary War to $36 trillion in 2025, national debt has always played a role in economic growth and policy. • Debt is split into intra-governmental (owed within the government) and publicly held (owed to investors, institutions, and foreign entities). • The Federal Reserve influences borrowing costs by setting interest rates, affecting everything from government debt payments to personal loans. • Printing money doesn't cause default, but it can devalue currency and increase prices, impacting purchasing power. • Spreading investments across different asset classes helps mitigate risk and combat inflationary pressures. Key Timestamps:(00:00) Understanding the U.S. National Debt (02:14) Components of the National Debt (07:55) The Role of the Federal Reserve (14:40) Modern Monetary Theory Explained (17:58) Criticisms of Modern Monetary Theory (26:41) Implications for Personal Finance (32:03) Combating Inflation and Taxes (39:18) Conclusion and Final Thoughts Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques, Modern Monetary Theory, national debt, diversification Mentions: https://bestinterest.blog/what-investments-actually-beat-inflation-since-2020/ 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 is joined by Chad Carson, who discusses residential real estate investing as a stable alternative to stocks and bonds. While real estate offers advantages like rental income, property appreciation, and tax benefits, Jesse also highlights challenges such as high costs, tenant issues, liquidity problems, and the time commitment required. Jesse thinks of his Rochester wealth management clients, and what some of them do.  Chad emphasizes choosing the right location, focusing on properties with minimal renovation needs, and securing financing that ensures a healthy cash flow. He advises new investors to avoid risky locations and avoid over-leveraging, recommending a steady, cautious approach. The discussion also touches on the stages of investing, from securing initial deals to building wealth and prioritizing stability.  The concept of the "small and mighty" investor is introduced, suggesting that a smaller, well-managed portfolio can generate significant passive income, offering more flexibility and freedom than large-scale investing. Both Jesse and Chad stress the importance of aligning investments with personal values and goals, encouraging listeners to prioritize lifestyle over asset accumulation - a pillar of financial planning.  Key Takeaways:• When investing in real estate, focus on areas with strong job markets and potential for growth. Avoid declining populations and single-industry towns. • Ensure mortgage payments are significantly lower than your rental income, ideally aiming for a 50% or lower mortgage-to-rent ratio. • Mortgages allow for property ownership you couldn't otherwise afford, but use debt carefully, especially in downturns. Ensure good debt management to avoid financial failure. • Whether through books, podcasts, or coaches, learning from experts can help build confidence and avoid mistakes. • Bigger isn't always better. A smaller, well-managed portfolio can generate significant passive income without the burden of managing hundreds of units. • Real estate should fit into your personal values and long-term lifestyle vision. Success is not about accumulating assets but achieving your desired way of life. Key Timestamps:(00:00) Introduction to Personal Finance for Long Term Investors (02:23) The Power of Leverage in Real Estate (07:35) Cons of Residential Real Estate Investing (15:02) Introducing Coach Chad Carson (17:01) Choosing the Right Real Estate Location (28:26) Understanding the Three Rental Stages (29:09) The Importance of Debt Management (31:51) Balancing Real Estate with a Busy Life (40:16) The Small and Mighty Real Estate Investor (45:56) Finding Your 'Enough' in Real Estate (51:32) Conclusion and Resources Key Topics Discussed:Personal Finance for the Long-Term Investor, The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, real estate, Chad Carson, leverage, debt, mortgage, Coach Carson Mentions:Website: https://www.coachcarson.com/ LinkedIn: https://www.linkedin.com/in/coachcarson/ More of The Best Interest:Check out the Best Interest Blog at bestinterest.blogContact 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.

Episode 100 of The Best Interest Podcast! This is a celebratory and reflective milestone featuring guest shout-outs, listener-favorite clips, and a discussion on the show's evolution. Jesse shares the podcast's origins, his journey from aerospace engineering to financial planning, and how the podcast nearly faded before finding renewed purpose in 2023. Throughout the episode, Joe Saul Sehy, Brian Feroldi, Paula Pant and other past guests are featured, shouting out The Best Interest and their own work, you'll certainly want to check out.  To celebrate, listeners wrote in with some of their favorite clips, including Jeremy Schneider's discussion with Jesse on his “7 Deadly Sins of Investing” from episode 70. Of course, Jesse's AMA's have been incredibly popular, so segments are featured from episodes 81 and 96 where Jesse answered questions about diversification, patience, and risk management.  Thanks, listeners, for supporting the podcast's first 100 episodes. We look forward to the future of "Personal Finance for Long-Term Investors."   Key Takeaways:• Relying solely on one asset class, such as large-cap U.S. stocks, increases risk and limits flexibility in different market conditions. • No asset class can outperform indefinitely; over time, returns tend to move back toward historical averages. • Holding international stocks can help balance risk, as different regions perform well at different times. • Just because a strategy has worked for years doesn't mean it will continue to do so; market conditions evolve. • As retirement nears, reducing portfolio volatility becomes more important, and diversifying helps protect against severe downturns. • The best strategy involves preparing for uncertainty, adjusting portfolios based on personal financial goals rather than chasing recent winners.   Key Timestamps:(03:43) Reflections on the Journey (15:15) Rebranding Announcement (19:44) Highlighting the Best Clips (38:53) The Importance of Indexing and Market Timing (40:52) Understanding the CAPE Ratio (45:12) The Risks of Timing the Market (51:45) Dollar Cost Averaging vs. Lump Sum Investing (54:42) Diversification: Why It Matters   Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, long term investors, Joe Saul Sehy, Brad Barrett, Nick Maggiulli, Justin Peters, Jeremy Schneider, Doug Cunnington, Joel Larsgaard, Paula Pant, andy Hill, Steve Adcock, Dan Otter, Brian Feroldi, episode 100, celebration, millionaire money habits   Mentions:Joe Saul Sehy: https://joesaulsehy.com/ Brad Barrett: https://choosefi.com/ Nick Maggiulli: https://ofdollarsanddata.com/ Justin Peters: https://www.tsirpodcast.com/ Jeremy Schneider: https://www.instagram.com/personalfinanceclub/?hl=en Doug Cunnington: https://milehighfi.com/ Joel Larsgaard: https://www.howtomoney.com/about-us/joel-larsgaard/ Paula Pant: https://affordanything.com/ Andy Hill: https://marriagekidsandmoney.com/about/ Steve Adcock: https://steveadcock.us/ Dan Otter: https://teachandretirerich.com/ Brian Feroldi: https://www.youtube.com/@BrianFeroldiYT    More of Personal Finance for Long-Term Investors:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog Personal Finance for Long-Term Investors 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.  

Time for another AMA with Jesse! First, Randy asks what it means to be rich, leading to an interesting evaluation of personal values, goals, and circumstances. Jesse explores relativity, “keeping up with the Joneses”, and what it means to have “enough”. Then, Bob asks about the potential tax burdens on beneficiaries and heirs, and Tom wonders whether some tax savings are worth the effort of logistical complexity. The fourth question comes from regular listener, Yogi, asking about the role of bonds in diversifying a portfolio. Jesse gets into the details of which bonds are which, which financial goals they're good for, and when you should consider other options. To wrap up the show, Hector asks about the “buy, borrow, die” strategy employed by the ultra-wealthy: buy appreciating assets, borrow against them for liquidity without selling, and pass them to heirs with a stepped-up cost basis, avoiding capital gains taxes.  If you'd like a question in a future AMA, send Jesse a message! Tune in next week for the 100th episode celebration!   Key Takeaways:• Wealth varies based on individual values and circumstances. It's less about achieving a specific number and more about feeling secure and content with your resources. • The tax burden of inherited IRAs is based on the beneficiary's income and tax bracket, which can differ significantly from the original contributor's tax savings. • Decisions like Roth conversions depend on whether the potential tax savings justify the added effort and complexity for an individual. • Bonds provide stability and dependability for short-term goals. Short-duration, high-quality bonds like U.S. Treasuries are less sensitive to interest rate changes and offer more reliability. • While effective for minimizing taxes, the “buy, borrow, die” strategy involves risks such as margin calls, regulatory changes, and the cumulative cost of loan interest potentially outweighing benefits. • Wealth strategies should focus on understanding and minimizing tax liabilities without excessive risk, avoiding overly aggressive tax avoidance tactics.   Key Timestamps:(02:17) Question 1: What Does It Mean to Be Rich? (09:11) Question 2: Concerns About 529 College Savings Plans (16:57) Question 3: Roth Conversions and Tax Savings (23:50) Question 4: Evaluating Bond Performance and Diversification (31:23) Question 5: The Buy, Borrow, Die Strategy   Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, buy borrow die, Roth conversions, tax avoidance, inheritance, bonds, diversification, rich, five year rules   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.

Jordan Grumet, AKA Doc G, returns to the podcast to share the difference between “Big P Purpose” and “little p purpose” and why you should pursue the seemingly less significant latter. Bringing together his experience in hospice care and finance, Jordan shines light on how we can create our purpose through personal growth and the pursuit of passions, rather than grandiose goals. Jordan calls these activities that bring joy "purpose anchors," which can be discovered through reflection and exploration. By engaging in these meaningful pursuits, individuals create positive ripple effects, fostering generational growth and leaving lasting legacies. This reframing of purpose as a process-driven journey encourages embracing life's uncertainties and finding fulfillment in the present. If you're hard at work, saving and investing, and still feeling uncertain about what it's all for, this is the perfect episode for you. Jordan brings actionable advice to big questions. Key Takeaways: • What's all this financial planning really for? • The difference between “big P Purpose” and “little p purpose”, and why you should pursue the latter. • How thinking about your regrets, the joys of childhood, and work can help you develop a purpose. • Engaging in your purpose each day, no matter how insignificant it may seem at the time, will change the world. • How “money scripts” pass on from generation to generation. • Don't worry about legacy, just do things that light you up. Key Timestamps: (00:00) Special Announcement (02:55) Exploring the Concept of Purpose (07:12) The Ongoing Adventure of Life's Purpose (11:33) Introducing Jordan Grumet (19:51) Understanding Big P vs. Little P Purpose (20:43) The Influence of Society on Purpose Anxiety (22:55) Identifying Your Purpose Anchors (27:25) The Power of Little P Purpose (33:37) Legacy and Generational Impact (36:31) Practical Steps to Build Purpose Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, purpose, meaning, Jordan Grumet, Doc G, life regrets, little p purpose, big p purpose Mentions: Website: https://jordangrumet.com/  LinkedIn: https://www.linkedin.com/in/jordan-grumet-38a506179/  Mentions:  The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy by Jordan Grumet, MD Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life by Jordan Grumet, MD 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 kicks today's show off with a monologue on the importance of having the right temperament for investing - it's not really about intelligence at all. Emotional stability and disciplined decision making outweigh expertise and intelligence when investing. The Dunning-Kruger effect and the paradox of choice are also highlighted, emphasizing the need to prioritize action over perfection in personal finance. For the second half of the show, Dr. Brad Klontz, Co-Founder of the Financial Psychology Institute and author of Start Thinking Rich, joins to discuss “money scripts”, which are subconscious beliefs about money inherited from previous generations, our society, or other people we're surrounded by. Throughout the conversation, the duo dispels myths about wealth, and makes a distinction between being “poor” (a limiting mindset) and being “broke” (a temporary financial state). The conversation gets deep into the stories we tell ourselves, how we present money, and how to adopt an internal locus of control and make lifestyle changes.  This episode is a must listen for anyone wanting to explore their own “money scripts” and rethink the way they talk to themselves - and others - about money. Key Takeaways:• How the Dunning-Kruger effect is affecting your investing decisions. • The difference between a satisficer and a maximizer - and why you may want to be the former. • What is a “money script”? And how can you change yours? • The patterns you may have inherited from even your great grandparents. • Consider how you rank on the following four patterns: avoidance, worship, vigilance, and status. • Research backed psychological insights about your relationship with money. Key Timestamps: (00:00) Understanding the Dunning-Kruger Effect (02:58) Insider vs. Outsider Perspectives in Sports and Investing (05:41) The Importance of Temperament in Investing (10:13) The Paradox of Choice and Financial Decision Making (18:07) Interview with Dr. Brad Klontz: Money Scripts and Financial Psychology (28:44) Understanding Money Scripts (30:42) Personal Reflections on Economic Backgrounds (33:33) Introducing the New Book: Start Thinking Rich (35:19) Harsh Truths About Wealth and Mindset (42:15) The Power of Locus of Control Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Brad Klontz, Start Thinking Rich, money scripts, financial psychology, limiting mindset, mindset growth, money myths, workaholic, workaholism, unhealthy patterns Mentions:Website: https://www.bradklontz.com/ LinkedIn: https://www.linkedin.com/in/drbradklontz/  Mentions: On Amazon: Start Thinking Rich: 21 Harsh Truths to Take You from Broke to Financial Freedom Great Investors' Little Secret:  https://bestinterest.blog/great-investors-little-secret/ How “Analysis Paralysis” Can Sabotage Our Finances: https://bestinterest.blog/opportunity-paranoia-analysis-paralysis/ 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.  

Talking solo, Jesse tackles two important, ever-present investing questions in today's monologue. Should I try to time the market? How do I beat the market? The truth is, the timeless advice stands: diversify your portfolio, steer clear of speculation, and invest early and often. Diversifying is like buying the haystack, rather than looking for the needle, because, the truth is, you probably won't find the needle. Speculative stock-picking is like picking out some straw and hoping it'll turn out to be the needle. To illustrate the benefits of consistent investing - rather than attempted market timing - Jesse tells the tale of Bad Timing Bill, Normal Nick, and Good Timing Gary. Bill and Gary both tried to time the market. This episode is packed with insight you'll want to return to again and again. Key Takeaways: • Don't look for the needle in the haystack. Buy the haystack. Most stock pickers stumble into success. • There's no such thing as skilled stock picking because we can never know the entire market. • Just because a business is massive and visible, doesn't mean it will forever make good decisions. • How to sort out a fair price for something. A good burger isn't worth 100 dollars! • What are CAPE and PE ratios? • The story of Bill, Nick, and Gary: Why you shouldn't try to time the market.  Key Timestamps:(00:00) The Best Interest Year in Review (08:02) The Evergreen Question: Is Now the Right Time to Invest? (11:58) The Case for Index Investing (25:16) Understanding Market Efficiency (29:13) The Starbucks Dilemma: Diversification vs. Concentration (32:01) The Importance of Price (32:39) Warren Buffett's Wisdom on Fair Prices (33:37) The Risks of Overconcentration in a Single Stock (34:14) Diversification and Risk Management (35:36) The Concept of Timing the Market (36:08) The CAPE Ratio Explained (46:39) Dollar Cost Averaging vs. Lump Sum Investing (51:27) The Complexity of Market Movements Key Topics Discussed:The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, stock picking, speculation, index funds, mutual funds, stock market, DIY investing Mentions:Wealth Creation in the U.S. Public Stock Markets 1926 to 2019 by Hendrik Bessembinder https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3537838  The Needle in the Haystack:  https://bestinterest.blog/the-needle-in-the-haystack/ Yes, You Can Beat the Market, But...:  https://bestinterest.blog/yes-you-can-beat-the-market/ Good Company, Bad Stock:  https://bestinterest.blog/good-company-bad-stock/ The CAPE Ratio vs. Future Returns: https://bestinterest.blog/cape-vs-future-returns/ 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 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 401k? Diversify, diversify, diversify. What Jesse's doing to prepare financially for fatherhood. 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:

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:

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:

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:

Jared Dillian was a Wall Street trader at Lehman Brothers, has written 4 books, and now writes 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 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 some unique takes on the FIRE movement and feel okay about that morning coffee, this is the episode for you!   Key Takeaways: How taxes can actually be really interesting! Why you should be ready to wait. Know your cash flow! Don't forget to prepare. How being smart about the big decisions will help you not sweat the small stuff. Why Jared doesn't want to retire. 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:

Paul Pant writes, podcasts, and speaks on financial independence, money management, and financial literacy. As the host of the Afford Anything Podcast, Paula has racked up more than 30 million downloads, ranking the show among the Top 50 Business Podcasts on Apple Podcasts. In this episode we learn how Paula realized she could travel the world on a limited income and eventually go on to financial independence through Afford Anything. If you're looking for some growth mindset inspiration that will help you broaden your perspective, this is the episode for you!   Key Takeaways: - How to move on (and grow) after financial mistakes. - Why we need reminders and safety measures. - How to afford anything with the power of priorities. - How Paula traveled the world and never got a job again. - What cap rate you should be looking for in a rental property. - Why you should start 10X thinking, rather than penny pinching.   Mentions:

Brian Feroldi is a prolific creator in the financial education space, having written over 3000 articles for the Motley Fool, published a book, “Why Does The Stock Market Go Up?”, and actively posting to his YouTube Channel. In this episode, Brian breaks down his checklist for what makes a company worth investing in and provides some insight into what we should do before we jump into investing. If you're interested in personal investing and some great guidelines to go along with it, this is the episode to listen to.   Key Takeaways: What is the index fund bubble? And what are some prominent thoughts on it? Should you be worried about an index fund bubble? How to get a sense of a company worth investing in. What criteria Brian uses when deciding what to invest in? Why you should “never interrupt your compounding unnecessarily.” Why you should take care of the boring before the exciting. Why you should keep your personal life and your investing life separate.   Mentions:

Joe Saul-Sehy is one of the hosts of Stacking Benjamins, which is one of the most listened-to podcasts in the personal finance space. In this episode, we discuss how to find a good financial advisor, how to chase time (not money), and even how to decide what your top priority is in life. If you're looking for an educational listen with plenty of laughs along the way, then this is the episode for you!   Key Takeaways: What you need to ask any financial advisor you're considering working with.  How Joe uses storytelling to make money make sense. Who you need to surround yourself with to find success. Before you ask what the cost is, ask what you're getting in return.  Why you need to chase time, not money.  How to put your goals in an MMA cage match to determine your priorities.   Mentions:

Today's show features Doug Cunnington, one of the hosts of the financial independence podcast Mile High FI. Doug highlights how he took conservative risks along the way to FI, and walks us through his career journey to financial independence. We discuss misconceptions about the FIRE movement, how to prepare for financial emergencies, and why it's never too late to start your own journey to financial goodness. This episode is a must listen!   Key Takeaways: What is risk, really? And how can you live with it? How to estimate risk in investing, and in yourself. The difference between volatility and risk. Why you need to do “financial fire drills.” How Doug set himself up for financial independence. What people get wrong about FI/RE. How to move on from a financial mess by looking forward. Stoicism and personal finance.   Mentions:

Diania Merriam is the founder of the EconoMe Conference, an exclusive gathering for the FIRE community (financial independence, retire early). Inspired by FIRE, Diania hit an impressive 60% savings rate and retired at 33. Of course, in retirement, you've got to stay active; what's the point of financial freedom if you've got nothing to do? Diania joins Jesse today to discuss CoastFI, SlowFI, and the need to enjoy the journey. If you're saving for retirement, but aren't sure what to do with that retirement, this episode is for you!   Key Takeaways: What inspired Diania to walk the Camino de Santiago. How to disconnect for your career with purpose. Why you need a vision for what your retirement will look like. Don't wait for financial independence to change your life. What are SlowFI and CoastFI? How to be an efficient saver, not a deprived saver. Why FI is better with friends.   Mentions:

Jeremy is the voice behind Personal Finance Club, a community of champions of the individual investor dedicated to bringing accessible financial education to all. The Personal Finance Club believes financial education improves lives and it should be taught in school. You might have seen Jeremy and Personal Finance Club on Instagram where he posts eye catching financial graphics to almost 600, 000 followers.   In this episode Jesse and Jeremy discuss the 7 Sins of Investing. These simple lessons will give you valuable insight into some habits to avoid, skills to develop, and knowledge to gain for your financial well-being.   Key Takeaways: Your home is a lifestyle choice, but it's not an investment - more of a hard to upkeep asset. Why you should “rent your fun”, treat money as a tool, and other useful ways to approach finances. How humans evolved to be impressionable and how this has been co-opted by consumerism. Live below your means, and invest early and often. Learn Jeremy's 7 Sins of Investing. Why you should just stand there and wait. Jeremy's Nectarine: Advice-Only Financial Advising.   Mentions:

Sean Mullaney is the FI Tax Guy (FI = Financial Independence). He's a financial planner and the president of Mullaney Financial and Tax Incorporated which offers fiduciary, fee-only, and advice-only financial planning. In this episode, Jesse dives deep on capital gains taxes, while Sean and Jesse dissect the Roth vs. Traditional debate, the efficacy of 529 Plans, and how to think about changes to the tax code coming in 2026.    Key Takeaways: What are capital gains? How to calculate capital gains, and the taxes on them. The NII tax explained.  10 ways to make the most of your capital gains. What is tax planning and how can you get started? How taking care of your financial future will also take care of your child's. Which accounts might be “shiny objects” and which ones will serve you well.  What change is coming to the Internal Revenue Code in 2026, and how to prepare.   Mentions:

Rose Lounsbury is a keynote speaker, an Amazon bestselling author, simplicity coach and the still-sane mom of triplets. She helps overwhelmed people create open spaces in their homes, their workspaces, and more importantly in their minds by letting go of the excess stuff that gets in the way.   In today's episode, Rose teaches us why towels are a great place to start when we're looking to simplify our lives. What do we do about gifts? Hobbies? Or everything that occupies our space, energy, or time? These questions (and more) are answered in this conversation between Rose and Jesse.   Key Takeaways: What is bimodal spending? And how can you apply it? Don't be afraid to spend on the things you really care about (and cut out what you don't). How to decide what's useful to you and what's beautiful. How to be a better gift giver and receiver.  How to pay attention to mental patterns that may be cluttering our minds. Start with decluttering the physical space, and then carry on to the mental space.   Mentions:

Today, Jesse shares some financial lessons from humble beginnings. There's much to learn from his first entrepreneurial endeavor: a baseball concession stand. Then, Andrew Giancola joins the pod to share his “Hero's Journey,” from a bottom point where he found himself unable to afford a fill-up of gasoline. Andrew has thoughts about peoples' biggest problem with money, about opportunity costs we all face, and whether you should rent or buy your next home. Thanks for joining us today on The Best Interest.   Key Takeaways and Timestamps: (0:00:44) - Jesse shares a story from his early financial life about starting a concession stand business as a kid to earn money to buy a computer game. (0:09:31) - Jesse shares about his first job cleaning bathrooms and cabins at a state park for minimum wage. (0:13:30) - Brief ad break. (0:14:32) - Andrew Giancola, host of The Personal Finance Podcast, joins the show. (0:15:23) - Andrew shares his “Hero Story” of living paycheck to paycheck after college and having an "a-ha" moment when he couldn't afford to fill up his gas tank. (0:18:25) - Andrew reflects that changing his money mindset and psychology was the biggest factor in learning to manage his money properly.  (0:19:45) - Andrew discusses working one-on-one with clients, focusing on identifying their biggest problems and goals around money. (0:21:40) - Andrew shares a story about starting a side business selling Christmas trees and learning entrepreneurial lessons from it. (0:23:20) - Trying new ventures, seeing what works, and not being afraid to abandon things that aren't working. (0:24:43) - The importance of evaluating opportunity costs in building wealth. (0:28:14) - Tactics for evaluating non-monetary opportunity costs like time with family. (0:28:50) - Brief ad break. (0:29:04) -The first $100k is the hardest to accumulate because it relies more on savings rate versus investment returns. Once you hit $100k, compound interest accelerates wealth building. (0:33:08) - The importance of calculating total cost of homeownership before deciding whether to buy or rent. (0:35:05) - While homeownership can make sense, a house shouldn't be viewed primarily as an investment.   Mentions: The Millionaire Next Door:  https://amzn.to/3FKFfme   More of Andrew:

In the day-to-day hustle of parenting, thinking long-term, especially regarding finances, is often challenging. With studies showing an estimated cost of $250,000 to raise a child from birth to age 18 (excluding college expenses), addressing your monetary matters becomes utterly crucial before you embark on parenting. Today, Jesse sits down with Andy Hill to discuss combining finances with a spouse, preparing financially for a family, and setting your children up with the right money habits and mindset.   Key Takeaways: The cost of raising a child - We highlight the estimated expenditure from birth to age 18. We address major costs such as childcare, medical, baby supplies, and other miscellaneous expenses. The importance of pre-baby financial planning - We discuss the significance of money talks between spouses, sharing financial goals, and setting up a budget for child expenses. Financial Preparation - We emphasize the importance of building an emergency fund and suggestive steps like paying off debts, focusing on retirement, and the necessity of considering life and health insurance. Tax Benefit - We share some key insights into how to make use of the various tax benefits available to parents in terms of child tax credit and dependent care credit. We also introduce you to tax-advantaged college saving accounts. Saving tips - We give you practical tips and recommendations on buying secondhand baby items through Facebook Marketplace, consignment sales, etc. as an effective strategy to save money. Financial Literacy - We speak about the importance of teaching children about financial subjects like shopping, budgeting, and saving. Also, we introduce the 'Make My Kid a Millionaire' course which provides age-based money lessons. Estate Planning - We touch on updating your estate plan after having kids and considering special needs planning if applicable. In closure - We wrap up with a sensible perspective, affirming that despite the high cost involved, kids are indeed worth every penny. A proper plan and regular communication about finances is crucial to setting up a stable financial future for your family.    Timestamps: (00:00:02) - Intro/welcome (00:00:12) - Podcast premise   (00:00:17) - Every episode teaches personal finance (00:00:20) - Jesse Cramer intro (00:00:22) - Episode intro (00:00:28) - Later guest intro (00:00:39) - Andy Hill intro   (00:00:45) - Andy Hill topics (00:00:49) - Review of the week (00:01:26) - Transition to main topic (00:01:31) - 12 financial topics for new parents (00:01:54) - Children are expensive (00:02:22) - Insurance coverage (00:03:56) - Life insurance matters  (00:04:17) - Focus on term life insurance (00:05:12) - Property and auto insurance (00:05:17) - Childcare costs (00:06:57) - Education costs (00:08:59) - Estate planning (00:10:11) - Long term financial goals (00:10:49) - Children and taxes (00:12:52) - Topics that change with kids (00:13:48) - Budgeting (00:15:34) - Debt management (00:16:27) - Special needs planning (00:17:21) - Digital management (00:17:59) - Roth IRAs for kids (00:20:13) - Generational wealth (00:20:29) - Kids are expensive but worth it (00:20:41) - Andy Hill intro (00:21:18) - Andy Hill background (00:22:27) - Money languages (00:24:13) - Understanding each other's perspectives (00:28:12) - When to combine finances (00:30:54) - Autonomy with money (00:32:21) - Preventing financial fights   (00:35:16) - Setting aside time to talk (00:37:18) - Tracking goals and expenses (00:39:20) - Focusing on the journey (00:40:11) - Kids are expensive (00:42:33) - Planning for kid expenses   (00:44:41) - Setting kids up for success (00:46:10) - Teaching money lessons   (00:48:22) - Make My Kid a Millionaire course (00:50:29) - Where to find Andy (00:50:38) - Outro   More of Andy:

Do you see yourself dying on top of a pile of gold like Scrooge McDuck? Today's guest, Chris Hutchins, shares his story of how he balances hacking his life: credit cards, chores, out of the box thinking, you name it, with keeping his end goals in mind. But, first, Jesse recounts his travels. He may have learned a lesson or two from the busy street traffic in Vietnam vs the quaint pubs of Ireland.    Key Takeaways: Why creating success is more about buy-in than perfection Taking life a beat slower The difference between being cheap and out of the box hacking Hacking your biggest expenses like travel and a home purchase Finding the best credit card(s) for your needs A two credit card arrangement for the average 6-figure household Welcome bonuses vs credit card points The concept of dying with zero Time vs talent vs treasure Parenting hacks: childcare, toys, pre-school   More of Chris: Meet Chris Hutchins, the award-winning host of the podcast All the Hacks, where he shares his expertise as an avid life hacker and financial optimizer. With a passion for upgrading life without breaking the bank, Chris has amassed millions of points and miles and gained recognition in a documentary on Financial Independence titled Playing with Fire. His journey has been featured in prestigious publications like the New York Times, Wall Street Journal, and CNBC.  

Nonillion… That's a number so big, I hadn't heard it before recording this episode. Should you budget and track every single dollar you spend? Should you put 10 percent of your income into your 401k? These are just two of the typical questions I get asked when it comes to money management. In fact, when you think about the hundreds of decisions the average person is faced with in their financial journey, you end up with a nonillion different possible outcomes.   This week I brought on Cody Garrett to make these decisions a little clearer. With dual degrees in music theory and contemporary piano performance, Cody shifted gears in 2018 to focus on his growing interest in finances. Having served as a music director for renowned Broadway shows to now, sharing actionable personal finance advice, Cody's journey is a testament to his drive and adaptability. Cody runs his firm that caters to DIY investors on the path of early retirement, and also educates over 1000 financial advisors, impacting the future of financial planning in a meaningful way.   Just because you're a do-it-yourself investor doesn't mean you have to do it alone. -Cody Garrett   Key Takeaways: Teaching is the best way to learn Understanding advice only financial planning The Transition Zone of financial planning: tax planning Traditional vs. Roth Contributions Marginal vs Effective Tax Rates The “Kiddie Tax” and 529 plans   Mentions: https://bestinterest.blog/financial-advisor-questions/   More of Guest:

How do you know when you are taking the right financial road? Should you prioritize saving money to be better off in the future? Or is it more beneficial to ensure you are using money as a resource for happiness in the present? Our guest today, Carl Jensen, has chosen the first option for the majority of his life, using money not as a resource for happiness, but one to defend against hardships. Recently, however, Carl has begun to take this road less traveled to optimize experiences while investing in his happiness. In this episode, we discuss how the household finances of our childhood can affect our spending habits as adults, and how to use exposure therapy to overcome the anxiety surrounding happiness based purchases.    Key Takeaways: How the household finances of our childhood can affect our long term financial habits Overcoming financial trauma How to spread good financial habits to those close to us Why taking the road less traveled isn't always the better option How to use exposure therapy to start making purchases for happiness How to overcome anxiety around an experience-based purchase Stepping away from money-first thinking to focus on the experience   Mentions: Bigger Pockets Money Podcast Episode with Jesse: https://www.biggerpockets.com/blog/money-335 I Will Teach You To Be Rich Podcast Episode with Carl and Mindy: https://www.iwillteachyoutoberich.com/108-mindy-carl/ 1500 Days Blog Post “Why Ramit?”: https://www.1500days.com/why-ramit/  Die With Zero: https://www.amazon.com/Die-Zero-Getting-Your-Money/dp/0358099765   More of Carl:

Today on the podcast, we have a fascinating guest. He's a gentleman by the name of Fritz Gilbert. He runs a blog called The Retirement Manifesto. As you might guess from the name of Fritz's blog, it's all about retirement. Now, yes, Fritz covers the nuts and bolts, the numbers of retirement, but we talk even more regarding the softer side of retirement, the things that retirees ought to be thinking about when it comes to just day-to-day life that they probably aren't thinking about. If you're younger like me, this might not quite apply to you yet, but I bet it applies to your parents, your aunts and uncles, and your older mentors at work. So, it's important we get people to think about these topics sooner. Enjoy!   Mentions: Morningstar's The Long View Interview with Fritz: https://www.morningstar.com/podcasts/the-long-view/e8b3c47b-0e67-4c00-b146-8b1060a5d604 The Retirement Manifesto Blog: https://www.theretirementmanifesto.com/blog/   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 exactly does it mean to live a regret free life? Our guest today, Jordan Grumet aka Doc G, shares the observations he's made as a hospice doctor. We get into a discussion about how money is a mirage. Many people view it as this big important thing, but in reality it's just a construct. It helps us achieve other things, and it's those other things which are truly important, not the money itself. It can be easy to forget money is just one of many tools at your disposal in building a happy life. So, today we extrapolate what those tools might be, and how money fits in the middle of it all.   Mentions: Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life: https://www.amazon.com/exec/obidos/ASIN/1646043545   More of Jordan: Website: https://jordangrumet.com/ Podcast: https://open.spotify.com/show/2CdpAR3sgltBBhDcpWRq0g   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, I'm going to share the five false proxies leading people astray in their financial goals. In fact, what if I told you a recent study revealed your $1 million investment principal was more likely to quadruple than remain flat even after decades of enjoying a 4% withdrawal rate? Would you rethink your saving strategy? Would you consider passing along some of your inheritance sooner in life? With that said, how do we come close to dying with zero? Our guest today has plenty of thoughts on bolstering the longevity of our finances, and surprisingly, his number one tip has nothing to do with your money. We also discuss lump sum investments vs dollar cost averaging and if you should be worrying about pennies when you might be missing out on dollars. I hope you enjoy my conversation with the creator of Of Dollars and Data, Nick Maggiulli. Mentions: Just Keep Buying: Proven Ways to Save Money and Build Your Wealth: https://amzn.to/3DCXs43 Die With Zero: Getting All You Can from Your Money and Your Life: https://amzn.to/3DAXnhs Outlive: The Science and Art of Longevity: https://amzn.to/457Yh0D   More of Nick: Blog: https://ofdollarsanddata.com/ LinkedIn: https://www.linkedin.com/in/nicholasmaggiulli   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 kind of mood would you find yourself in if a tree fell onto your house? Would it ruin your day? Our guests might have something to say about that…   Joining me today are two of the most outrageously optimistic, enthusiastic experts in personal finance, Joel O'Leary and Joel Laarsgard.   I'll often have clients come in and say, “Jesse, we really want to approach things conservatively. I mean after all, you've seen the news, right? We know we're heading into a recession.” And on one hand, of course, we want to be paying attention to the economy, but what do the short term fluctuations in the news cycle really mean to us over the span of 30 years? We shouldn't let a negative bias harm our long-term financial health.    Today we discuss if there's truly a force behind the power of positivity and what it could mean in your financial situation. After all, one of Joel's favorite quotes is “invest like an optimist and save like a pessimist.” So, join me in this lighthearted conversation as we break it all down.   More of Joel Laarsgard: https://5amjoel.com/   More of Joel O'Leary: https://www.howtomoney.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.

Today's episode starts in Minnesota, during an experiment where young men were intentionally starved. They knew starvation would affect their body, but were shocked by how it affected their brains. We then travel to Johnsonburg, a small town in Pennsylvania, where an unexpected event involving deer and a newly constructed bridge made headlines.    Did you know that mammal brains, including ours, share a common trait? It's called the amygdala, a remarkable part of our brain responsible for our fight or flight response. Just like the deer that instinctively jumped off the highway bypass, we too have an impulse that urges us to take drastic action when faced with fear. In the context of investing, this impulse often leads us to panic sell our portfolios during market downturns.   But is this fear-driven response always rational, or is it short-sighted? Fear, after all, is a survival mechanism designed to prompt us into action that alleviates the feeling of fear. However, when it comes to our investments, is it more crucial to survive negative outcomes than to chase maximum returns during favorable times?   Today, Jesse explains the psychology of investing including the answer to a popular question, should you have bonds in your investment portfolio? Only when the tide goes down do we discover who's been swimming naked. Don't let fear dictate your financial future, and instead learn why the true cost of investing is all psychological.   Mentions: Malcolm Gladwell's podcast episode:  https://www.pushkin.fm/podcasts/revisionist-history/the-department-of-physiological-hygiene   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.