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.