Jesse sits down with Andy Hill—personal finance educator, podcast host, and creator of Marriage, Kids, and Money—for a candid conversation about building wealth while building a life you actually enjoy. Andy shares how a mix of financial discipline, intentional goal-setting, and family-centered values helped him and his wife pay off their mortgage by age 35 and achieve financial independence on their own terms. Together, they unpack why traditional FIRE goals often miss the human side of money, how to define "enough," and why generosity and purpose are essential parts of financial freedom. Andy also opens up about the shift from chasing net worth to focusing on net happiness, revealing the moment he realized money was no longer the main goal—but a tool for creating the life and impact he wanted most. Throughout, Jesse and Andy remind listeners that real wealth isn't about numbers—it's about freedom, joy, and using money to live aligned with what truly matters. Key Takeaways:• Financial freedom isn't just about money—it's about creating the life and relationships you truly want. • Family alignment around financial goals strengthens relationships and ensures everyone is moving in the same direction. • Andy's shift from "net worth" to "net happiness" redefined how he measures success and balance. • Andy emphasizes financial independence on your own terms, not a one-size-fits-all version of FIRE. • Clarity creates motivation—when your goals align with personal meaning, saving and investing feel purposeful. • Sustainability matters more than intensity—consistent, realistic habits lead to long-term financial wellness. Key Timestamps:(00:44) – The Value of Time in Financial Planning (05:16) – The Importance of Buying Back Your Time (08:31) – Interview with Andy Hill: Owning Your Time (14:33) – Exploring the Concept of Coast FIRE (18:51) – Dreaming of a Three-Day Work Week (22:18) – The Value of Relationships (25:05) – Practical Tips for Transitioning to a Three-Day Work Week (29:45) – Involving Kids in Financial Planning (34:27) – Diversifying Your Identity Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning

Today, Jesse is joined by Dr. Phil Pearlman—psychologist, behavioral finance veteran, and founder of the Pearl Institute—for a conversation about how long-term health and long-term wealth are two sides of the same coin. Together, they explore why the holiday season, while full of joy and connection, is also the unhealthiest stretch of the year for most Americans—and how small, deliberate choices can reverse that trend. Phil shares his "four pillars of health"—nutrition, exercise, sleep, and love/community—alongside his own powerful story of addiction, recovery, and rediscovering the athlete within. From the parallels between compounding habits and compounding returns to the dangers of "energy toxicity" in modern diets, the discussion connects physical and financial wellbeing through the shared principles of discipline, awareness, and intentional living. Phil explains why cutting alcohol, prioritizing protein, and starting with just one sustainable habit—like morning walks—can transform both body and mindset. Throughout, Jesse and Phil remind listeners that you only get one body, one life, and one chance to invest in both wisely. Key Takeaways: • Health and wealth are interconnected — both require discipline, patience, and compounding habits to create long-term success. • Nutrition is the top priority; you can't "out-exercise" a bad diet, and most health challenges begin with poor food choices. • Alcohol is one of the biggest barriers to health, harming sleep, metabolism, mood, and long-term physical wellness. • Phil's personal transformation—from addiction and poor health to sobriety and vitality—shows that renewal is always possible. • Morning walks are a high-impact, low-barrier habit, improving mood, metabolism, and sleep cycles. • Community and connection are health essentials, not luxuries; love and belonging strengthen both body and mind. Key Timestamps: (00:00) – The Power of a Deeper Yes (07:29) – Identifying Your Core Values and Spending (12:00) – The Four Pillars of Health (22:06) – Seasonality and Health During the Holidays (33:41) – The Role of Alcohol in Nutrition (39:10) – Setting Health Goals for the New Year Key Topics Discussed:The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Adviso

Jesse returns for the 10th "Ask Me Anything" episode to tackle three listener questions that cut to the core of modern wealth planning. He opens with a deep dive into direct indexing, separating substance from sales pitch. While advocates tout it as the next evolution of indexing—combining personalization and tax-loss harvesting—Jesse explains why, for most investors, the extra complexity, cost, and tracking error outweigh the modest tax advantages, making low-cost ETFs the better long-term choice. Next, he answers a question from a listener whose retirement timeline doesn't align with their spouse's, exploring how couples can navigate income changes, healthcare coverage, and tax strategy when one partner stops working years before the other. He breaks down the pros and cons of filing jointly versus separately, showing why joint filing almost always leads to lower overall taxes and greater flexibility. Finally, Jesse delivers a masterclass on decumulation—the art and order of withdrawing money in retirement. From spending taxable assets first to preserving Roth and HSA accounts for last, he maps out how smart sequencing, Roth conversions, and bracket management can extend portfolio life, minimize taxes, and keep retirees financially steady through every stage of the journey. Key Takeaways:• Direct indexing isn't revolutionary for most investors—it's often an overhyped, higher-cost alternative to low-cost ETFs with limited long-term benefits. • Married filing jointly is almost always the better tax choice, offering lower overall tax rates, higher standard deductions, and broader eligibility for credits. • Before changing filing status, couples should test both scenarios using online 1040 tax calculators to see the real impact on their total tax bill. • Guardrail and Monte Carlo strategies help retirees adjust withdrawal rates dynamically based on market performance, rather than using a rigid 4% rule. • HSAs can be used as stealth retirement accounts, reimbursing decades-old medical expenses tax-free or even acting as traditional IRAs after age 65. • The key to successful retirement planning is flexibility—balancing tax efficiency, market uncertainty, and personal goals to ensure sustainable income for decades. Key Timestamps:(02:24) – Tax Loss Harvesting: Strategies and Examples (10:06) – Direct Indexing: Pros and Cons (17:1

Today, Jesse is joined by Professor John Dinsmore—behavioral finance researcher, marketing scholar, and author of The Marketing of Debt: How They Get You—for a conversation about how persuasion, psychology, and modern advertising quietly shape our financial lives. Together, they explore how marketers exploit human biases like loss aversion, anchoring, and over-optimism to sell products, loans, and debt, and why AI-driven "adaptive ads" are making it harder than ever to recognize when we're being influenced. John shares real-world examples—from car dealerships to "buy now, pay later" offers and sports betting apps—revealing how even savvy consumers fall prey to tactics designed to exploit fear, emotion, and cognitive shortcuts. The discussion also dives into the growing vulnerability of retirees targeted by complex financial products, and why awareness, self-monitoring, and slowing down decisions are key defenses. Throughout, Jesse and John remind listeners that acknowledging our weaknesses is a strength—and that understanding how marketing works is one of the best ways to protect both our wallets and our wellbeing.  Key Takeaways:• Marketing works on everyone—even when we think we're immune. Most people admit that advertising influences others, but few realize how deeply it shapes their own decisions. • People tend to believe they'll have more time, money, or stability in the future, making it easy to justify debt today. • Loss aversion drives many financial mistakes. We fear losses more than we value gains, which leads us to buy unnecessary warranties, insurance, or "safety" products. • AI-powered marketing will get subtler. As systems learn to mimic human tone and emotion, it will become harder to tell when you're being influenced. • Social media blurs the line between content and advertising. Influencer partnerships and native ads make it harder to recognize when you're being sold to. • Being "weak" isn't failure—it's human. Admitting our psychological blind spots allows us to build systems and habits that protect us. Key Timestamps:(01:49) – Understanding Personal Weaknesses (04:25) – The Impact of Marketing and Advertising (08:22) – Interview with Professor John Dinsmore (13:19) – The Marketing of Debt (25:56) – Practical Tips to Combat Marketing Influence Key Topics

Jesse goes solo for a deep dive into the vital yet often overlooked world of special needs financial planning. He opens with a personal story about his daughter's illness—an experience that deepened his empathy for parents whose caregiving journeys never pause—and uses it to frame the emotional and financial realities families face when raising a child with disabilities. From there, he explores how special needs planning extends beyond traditional wealth management, requiring families to think in decades, not years, while balancing their own retirement goals with lifelong care needs. Jesse breaks down key tools such as special needs trusts, ABLE accounts, and government programs like SSI and Medicaid, explaining how they work together to preserve benefits and provide sustainable support. He also examines the potential role of permanent life insurance as a funding mechanism for long-term care, the legal importance of guardianship and trusteeship, and the wisdom of separating caregiving and financial responsibilities to prevent burnout. Throughout, Jesse underscores the need for community resources, professional guidance, and self-care—reminding listeners that special needs planning isn't just about money, but about love, security, and building a future where every member of the family can thrive. Key Takeaways:• Raising a child with special needs requires planning for both the parents' and the child's lifetimes—often extending decades beyond traditional financial horizons. • Special needs families face higher ongoing costs, from medical treatments and therapies to adaptive equipment and in-home care. • Core financial fundamentals—emergency savings, retirement planning, tax strategy, and estate planning—remain essential but must be adapted for special needs circumstances. • Nonprofits, community organizations, and local programs can offer both financial aid and emotional support for families. • Professional guidance from fiduciary planners and special needs attorneys can help families integrate benefits, trusts, and insurance effectively. • Above all, special needs planning is about more than money—it's about love, security, and ensuring a dignified, supported life for every family member. Key Timestamps:(00:00) – Deep Dive: Special Needs Planning (08:12) – Unique Financial Challenges of Special Needs Families (15:56) – Speci

Jesse fields six wide-ranging listener questions that dig into the heart of financial planning and investing. He opens with a challenge to the idea that age alone dictates portfolio strategy, emphasizing instead that time horizons, goals, and...

Today, Jesse is joined by Spencer Reese—Air Force veteran, financial educator, and creator of the Military Money Manual—for a conversation about the surprising overlap between military transitions and civilian retirement. Together, they explore...

Today, Jesse is joined by Hanna Horvath—Certified Financial Planner, managing editor at Bankrate, and author of the Your Brain on Money newsletter—for a deep dive into the psychology behind our financial decisions and why money is never just about...

Today, Jesse goes solo for a candid episode unpacking the most common mistakes and misconceptions he sees in personal finance, from the temptation to “rip off the bandaid” with Roth conversions to the behavioral traps of availability bias and...

Today, Jesse is joined by Kelan Kline, co-founder of The Savvy Couple, who shares his entrepreneurial journey from working as a jail deputy to building a successful online personal finance brand, emphasizing the importance of leveraging scalable...

Jesse tackles six thoughtful listener questions spanning a range of personal finance topics. He begins with a question about using Social Security and pension payments as a means to replace bonds in a retirement portfolio. Why do we own bonds, anyway?...

Jesse welcomes back Peter Lazaroff to discuss the psychology and strategy of investing during uncertain times. They explore how media narratives and recession fears can distort investor behavior, emphasizing the importance of focusing on business...

Today’s episode is a special bonus episode, a companion to Jesse’s discussion on episode 555 of ChooseFI! Jesse examines the risks of over-optimization in personal finance, concentrating on tax-loss harvesting, asset allocation, Roth conversions,...

Jesse explores the timeless wisdom of Warren Buffett, highlighting both his disciplined investment philosophy and his unwavering emphasis on trust and character. Jesse breaks down Buffett’s approach to buying great businesses at fair prices, holding...

Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, Jeremy Schneider, Doc G, and Joe Saul-Sehy. Diania highlights the “iceberg principle” of stealth...

Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for high earners, healthcare in retirement, and investing during economic uncertainty. He explains that...

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...

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...

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...

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...