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 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://primecuts.philpearlman.com/
LinkedIn: https://www.linkedin.com/in/philip-pearlman-1002183/
Mentions:
https://bestinterest.blog/do-you-have-a-deeper-yes/

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

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 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
(17:18) – Financial and Tax Planning for Lopsided Retirements
(24:09) – Retirement Withdrawal Order of Operations
(32:39) – Real-Life Financial Planning Experiences
(40:56) – Roth Conversions and Tax Bracket Management
(45:37) – Optimizing for Post-Death and Social Security Timing
(52:26) – Common Mistakes in Retirement Withdrawal Strategies

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/retirement-withdrawal-order-of-operations/
https://www.guidestone.org/resources/education/calculators/tax/tax1040
https://bestinterest.blog/0-capital-gains-vs-roth-conversions-how-to-optimize-in-your-financial-plan/
https://bestinterest.blog/spousal-survivor-divorced-social-security/

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

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 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 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://www.johndinsmore.com/
LinkedIn: https://www.linkedin.com/in/johnbdinsmore/
Mentions:
https://bestinterest.blog/i-am-weak/
The Marketing of Debt: How They Get You by John B. Dinsmore

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

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 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) – Special Needs Trusts: Protecting Your Child's Future
(19:36) – Introduction to ABLE Accounts
(23:59) – Life Insurance for Special Needs Families
(28:37) – Guardianship and Legal Planning
(33:45) – Community and Professional Resources

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

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

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 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 diversification determine the right balance between growth and preservation. From there, Jesse advises a listener who recently inherited $1 million on how to integrate the windfall into an early retirement plan through detailed cash flow projections, withdrawal strategies, and careful consideration of pensions and Social Security. Next, he unpacks the difference between risk tolerance and risk capacity—framing them as willingness versus ability to take risk—and illustrates how these concepts vary depending on age, assets, and future income. A question about bonds leads to a deep dive on duration, interest rate sensitivity, and why bond funds and individual bonds behave more alike than many investors assume, with practical guidance on structuring fixed income for retirement needs. Shifting to income growth, Jesse shares seven strategies for boosting earnings over time, from negotiating raises and pursuing certifications to building businesses, climbing the career ladder, and gaining equity participation. Finally, he closes with a clear primer on Bitcoin, explaining blockchain, mining, and the role of trust in money, while stressing that investors don't need cryptocurrency in their portfolios—but should at least understand what it is and why it matters.

Key Takeaways:
• Investment strategy should be based on goals and timelines, not just age.
• A $1 million inheritance should be planned with the same rigor as any other asset, while respecting any personal or emotional ties.
• Risk tolerance reflects your willingness to endure volatility, while risk capacity measures your financial ability to recover from losses.
• Bond funds and individual bonds are functionally similar, especially when held to maturity.
• Negotiating with employers or job hopping can be effective short-term paths to higher pay. Building side businesses or securing equity participation can create outsized wealth growth over time.
• Investors don't need crypto in their portfolios, but understanding how it works helps in today's financial landscape.

Key Timestamps:
(01:58) – Question #1: Understanding Risk and Reward in Investing
(15:01) – Question #2: David's Early Retirement Strategy
(22:21) – Question #3: Karen's Question on Risk Capacity
(31:09) – Question #4: James' Concern About Bond Funds
(42:39) – Question #5: Tips for Increasing Your Income
(48:20) – Strategic Career Climbing
(53:47) – Question #6: Introduction to Cryptocurrency
(01:00:33) – The Role of Trust in Money and Bitcoin
(01:09:16) – Bitcoin Wallets and Blockchain Explained
(01:13:27) – Cryptographic Puzzles and Proof of Work
(01:24:37) – Concluding Thoughts and Future Episodes

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/risk-and-reward/
https://bestinterest.blog/stocks-for-wealth-bonds-for-sanity/
https://bestinterest.blog/winning-the-game-retiring-at-57-with-4-million/
https://bestinterest.blog/raises-negotiations/
https://bestinterest.blog/explaining-bitcoin-in-simple-terms/

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

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 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 numbers. Together, they explore how unconscious "money scripts" formed in childhood shape lifelong habits, why emotional discipline matters more than willpower, and how anxiety shows up even for people who have "won the game" financially. Hanna explains how retirement brings not just financial questions but also an identity shift, making purpose and values as important as portfolio allocation. They discuss strategies for reframing our relationship with volatility, using fire-drill style planning to prepare for downturns, and creating small gaps between emotions and actions to avoid costly mistakes. Throughout, Jesse and Hanna remind listeners that building lasting wealth is less about chasing fads or quick wins and more about cultivating awareness, resilience, and intentionality in both mindset and money.

Key Takeaways:
• Money is never just about math—it's deeply tied to psychology, emotions, and unconscious beliefs.
• Emotional discipline means creating space between feelings and actions, not trying to eliminate emotions altogether.
• Retirement isn't just a financial transition—it's a major identity shift that can create anxiety even for those who are financially prepared.
• "Fire drills" for your financial plan can prepare you emotionally and practically for downturns before they happen.
• Social media and sensational financial headlines amplify fear, making discernment and discipline even more critical.
• Retirement satisfaction depends on aligning money decisions with personal values, whether that means family, travel, community, or freedom.

Key Timestamps:
(00:00) – The Psychology of Money: Fads and Mimetic Desire
(15:35) – The Hedonic Treadmill and Financial Contentment
(21:41) – Understanding Behavioral Loss Tolerance
(32:03) – The Spectrum of Risk Tolerance
(38:51) – Money Scripts and Financial Behavior
(42:33) – The Importance of Emotional Discipline
(47:31) – Identity Shift in Retirement
(01:04:53) – DIY Investing and Self-Compassion

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://yourbrainonmoney.substack.com/
LinkedIn: https://www.linkedin.com/in/hanna-riley-horvath/
Mentions:
https://bestinterest.blog/fad/
https://bestinterest.blog/eat-drink-and-be-content/
https://bestinterest.blog/behavioral-loss-tolerance/

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

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 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 flawed math around investment returns. He breaks down a real listener case study to show why paying millions in unnecessary taxes up front rarely makes sense, and explains why geometric averages—not arithmetic ones—are the only way to understand long-term investment performance. Jesse also tackles the question of whether hiring a financial planner still matters in an age of index funds, outlining how professional guidance can protect investors from costly behavioral mistakes and add value through tax strategies, estate planning, and disciplined execution. He goes behind the curtain on why most planners don't offer hourly services, compares business models in the industry, and underscores that even high earners can't outgrow poor spending habits. Finally, Jesse calls out the dangers of internet financial advice and reminds listeners that true financial success comes from avoiding pitfalls, questioning easy narratives, and building steady, intentional plans for the long run.

Key Takeaways:
• Availability bias influences investors—we tend to make decisions based on the most recent or vivid information, not on comprehensive analysis.
• Neighbors' choices aren't financial advice—copying friends or coworkers' strategies can be dangerous without context.
• The arithmetic average is misleading in investing—it ignores compounding and makes returns look better than they are. Geometric averages (compound returns) are the correct measure—they show the real growth rate of investments over time.
• Financial advisors provide behavioral coaching and planning, not just advice.
• You can't out-compound bad spending—even large salaries can't overcome low savings rates.
• Internet financial advice is the wild west—anonymous content often lacks accountability or accuracy.

Key Timestamps:
(00:00) – Common Financial Planning Mistakes
(08:08) – Availability Bias
(11:42) – Arithmetic vs. Geometric Averages in Investing
(21:48) – The Value of Financial Planners Beyond Index Funds
(35:44) – Understanding RIA Regulations and Hourly Planning
(41:22) – The Benefits of AUM Fee Model
(46:45) – The Importance of Spending Plans
(58:38) – Navigating Internet Financial Advice

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:
The Dalbar Study: https://www.evaluatorfunds.com/jp-morgan-the-case-for-always-staying-invested/

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Consider working with me at https://bestinterest.blog/work/

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.