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.