In this candid solo episode, Jesse walks through a series of financial decisions that look "wrong" on paper but make complete sense when viewed through the lens of real life, values, and tradeoffs. Using personal examples, he challenges the idea that optimal spreadsheets should always dictate behavior, arguing instead that financial planning exists to support a life well lived—not to win theoretical efficiency contests. Jesse explains why holding excess cash even when expected returns favor investing, and prioritizing flexibility and simplicity over marginal tax optimization. Throughout the episode, he dismantles the myth that good planning means eliminating all inefficiency, emphasizing that peace of mind, optionality, and behavioral alignment often outweigh incremental gains. By reframing "dumb" financial moves as intentional choices made with eyes wide open, Jesse encourages listeners to separate true financial mistakes from decisions that are simply mismatched to someone else's values or risk tolerance—and to give themselves permission to choose what actually works for their lives.

Key Takeaways:
• Not all financially "inefficient" decisions are mistakes. Optimization often ignores behavioral and emotional realities.
• Taking care of a low interest loan can offer peace of mind—despit better returns often being found in investments.
• Leasing a car or renting a home may be the right move—depending on the situation.
• Using an HSA early may seem like a bad idea, but it could help reduce stress elsewhere in our financial lives.
• Being a "lazy investor" is often better than being a complicated investor.
• Spreadsheets cannot fully capture human behavior. A "good" decision can look bad to outsiders and still be right.

Key Timestamps:
(00:46) – Sandbox Investing Accounts
(04:48) – Paying Off Low-Interest Loans
(09:37) – Leasing a Car: Pros and Cons
(13:05) – Emergency Funds and Cash Allocation
(19:56) – Balancing Emotions and Math in Social Security Decisions
(22:17) – Owning Company Stock: Risks and Rewards
(23:33) – Taxable Brokerage Accounts vs. Qualified Retirement Accounts
(27:55) – Using HSA Accounts for Medical Expenses
(29:51) – Renting vs. Buying: A Balanced Perspective
(34:52) – The Concept of Lazy Investing
(39:59) – Continuous Learning in Personal Finance

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/

Personal Finance for Long-Term Investors 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 is joined by Jeremy Keil—Certified Financial Planner, Chartered Financial Analyst, author of Retire Today, and host of the Retirement Revealed podcast—for a wide-ranging conversation that reframes how people should think about retirement decisions long before and long after the final day of work. Together, they explore why most people retire earlier than planned, why longevity is so often misunderstood, and how flawed assumptions about life expectancy, Social Security, and taxes can quietly undermine otherwise solid plans. Jeremy introduces the concept of "retirement longevity" as both when retirement starts and how long it may last, emphasizing the importance of personalized life expectancy modeling, joint longevity for couples, and treating Social Security as insurance rather than an investment. The discussion also dives deep into Jeremy's five-step Retirement Master Plan—starting with spending, then income, tax planning, investing, and legacy—highlighting why tax strategy and Roth conversions are often the most powerful yet overlooked levers in retirement planning. Throughout the episode, Jesse and Jeremy blend technical insight with behavioral clarity, addressing the emotional hurdles retirees face, from fear of running out of money to the identity shift from saver to spender, ultimately offering a grounded, practical roadmap for building confidence and clarity in retirement.

Key Takeaways:
• Average life expectancy statistics are misleading for near-retirees. Personalized longevity estimates are far more useful than population averages.
• Couples must plan around joint life expectancy, not individual longevity.
• Current take-home pay is a practical proxy for estimating retirement lifestyle spending.
• Roth conversions are situational tools, not universally good strategies. The timing and size of Roth conversions matter as much as the decision to do them.
• Many retirees struggle emotionally with shifting from saving to spending. The healthiest mindset shift is from "saver" or "spender" to lifelong "planner."

Key Timestamps:
(01:41) – Understanding Fixed Indexed Annuities
(07:30) – Roth Conversion and Annuities: A Critical Look
(10:55) – Dividends and Income in Retirement Planning
(17:34) – Retirement Longevity and Planning
(28:06) – Understanding Life Expectancy in Retirement Planning
(32:06) – Comprehensive Retirement Planning
(33:02) – The Five Steps to Create Your Retirement Master Plan
(38:52) – Tax Planning and Roth Conversions
(47:12) – Emotional Hurdles in Retirement

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: jeremykeil.com
LinkedIn: https://www.linkedin.com/in/mrretirement/
Mentions:
Retire Today: Create Your Retirement Master Plan in 5 Simple Steps by Jeremy Keil
https://www.youtube.com/@MrRetirement
https://www.longevityillustrator.org/
https://keilfp.com/blogpodcast/
https://bestinterest.blog/dividends-and-income-withdrawal-rate/
https://bestinterest.blog/about-that-free-steak-dinner/

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.

In this Christmas episode, Jesse steps back from year-end checklists and market noise to tell a more personal story—one shaped by the "ghosts" of his financial past, present, and future. He begins with the early experiences that formed his relationship with money: a summer concession stand that taught him pricing, customer focus, and the power of simply telling people what you do; a first job cleaning bathrooms at a state park that clarified the difference between earning a paycheck and building a career; and the moment in his mid-20s when seeing real dollars in his 401(k) pulled him into a decade-long deep dive on personal finance, blogging, and eventually a full career change into wealth management. From there, he pivots into a transparent walkthrough of his current systems—how he and his wife structure savings, manage cash, use insurance, approach debt, track spending, and design an investment allocation that reflects real life rather than theory. He also shares three planning cases from this year that reveal the human side of financial advice: navigating retirement after a family death, unwinding concentrated stock risk for a high-earning executive, and giving one engineer the peace of mind to sleep through layoff fears. Looking ahead, Jesse reflects on where the industry is headed—AI-enabled tools, changing fee models, and a shift toward values-based planning—while outlining how he and his family think about the future with a firm grip on flexibility, priorities, and the fleeting years of raising young children. It's an intimate, thoughtful close to the year—less about spreadsheets and more about why financial planning matters in the life you're actually living.

Key Takeaways:
• Take time to seek out new opportunities. Putting yourself out there for advancement is one of the most straightforward ways to advance financially.
• Getting "skin in the game" with real dollars in a 401(k) or investment account is often the catalyst for learning personal finance at a deeper level.
• A blended approach to retirement savings (401(k), Roth IRA, HSA) builds both tax flexibility and long-term resilience.
• Cash-management infrastructure—joint accounts, high-yield banks, and legacy accounts—matters less than ensuring clarity, shared access, and ease of use.
• Tools like the state-run CHIP/Child Health Plus programs can dramatically reduce healthcare costs for families with children.
• Strong personal finances create flexibility: the ability to enjoy life now while still protecting the future—especially during the irreplaceable years of raising children.

Key Timestamps:
(04:22) – Financial Past: Early Money Lessons
(07:09) – Entrepreneurial Beginnings: The Concession Stand
(10:36) – First Job Experiences and Lessons Learned
(20:20) – Financial Present: Family Finances and Planning
(26:23) – Our Investment Strategy
(32:58) – Tax Planning Insights
(37:25) – Evolving Budgeting Methods
(45:08) – Financial Future: What Will You Make of It?

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.

On Jesse's 11th "Ask Me Anything" episode, he unpacks four questions that sit at the center of real-life financial decision-making. He starts with a grounded look at the 15-year vs. 30-year mortgage debate, cutting through rules of thumb to show how interest rates, liquidity, cash-flow, and even your personal comfort with debt shape the right choice far more than blanket advice ever could. From there, he turns to the under-discussed strategy behind Health Savings Accounts—why the "invest and reimburse later" approach works, when it stops working, and how the tax bomb of leaving HSA dollars to non-spouse heirs should change how listeners think about funding and spending those accounts in their 50s and beyond. In a detailed case study, Jesse walks through a listener's complex 2026 tax year involving rental-property capital gains, ACA cliffs, Social Security timing, and potential Roth conversions, revealing how layered tax rules—income brackets, capital gains stacking, depreciation recapture, and NIIT—interact in ways that can either save or silently cost retirees thousands. And finally, he tackles whether a diehard DIY investor or Boglehead should ever hire a financial planner, drawing a sharp distinction between the "Uncle Franks" who truly live and breathe this stuff and the "Nicks" who love markets but miss the deeper planning work. With clarity, nuance, and practical wisdom, Jesse shows listeners not just what to do, but how to think through the tradeoffs that define good long-term planning.

Key Takeaways:
• A 15-year mortgage saves significant interest, but the higher monthly payments reduce cash-flow flexibility and increase default risk.
• A 30-year mortgage often wins mathematically when investors "invest the difference," thanks to potentially higher long-term market returns versus fixed loan rates.
• Choosing a mortgage term is partly a psychological decision, not just a financial optimization.
• HSA dollars become a tax trap if left to non-spouse heirs, who must treat the entire balance as taxable income in the year of inheritance.
• Selling a rental property triggers both capital gains and depreciation recapture, which can dramatically increase taxable income in that year.
• DIY investors vary widely—some are true experts, while others know just enough to make avoidable mistakes.

Key Timestamps:
(02:04) – 15-Year vs. 30-Year Mortgage Debate
(11:03) – Liquidity and Mortgage Payments
(13:48) – HSA Accounts: When to Fund and When to Use
(25:37) – Spending Down HSA Balances
(26:39) – Allison's Financial Planning Dilemma
(29:05) – Analyzing Capital Gains and Tax Implications
(35:49) – Considering Social Security Timing
(38:54) – The Role of Financial Planners for DIY Investors

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/

Personal Finance for Long-Term Investors 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 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 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://marriagekidsandmoney.com/
LinkedIn: https://www.linkedin.com/in/andyhillmkm/

Get your pre-copy of Andy's new book here: https://amzn.to/4phCgqF

"Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind" by Andy Hill

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 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.