Personal Finance for Long-Term Investors - The Best Interest

Where Investors Go Wrong: Tax Traps, Math Mistakes, and Behavioral Biases - E115

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Sep 3, 2025

Jesse dives into the common pitfalls investors face, like the allure of hasty Roth conversions and the cognitive bias of availability. He emphasizes understanding geometric averages over arithmetic ones for investment performance. A real listener case study illustrates the pitfalls of upfront tax payments. The discussion highlights the crucial role of financial planners in combating behavioral biases and effective tax strategies. Finally, Jesse warns against the dangers of internet advice, advocating for personalized, long-term financial planning.

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ADVICE

Don't Lump-Sum Roth Convert Without Planning

Avoid converting all pre-tax retirement assets to Roth in one large move without clear tax math.
Spread conversions over time and compare current marginal rates to future expected rates before paying large taxes upfront.

INSIGHT

Availability Bias Drives Copycat Financial Moves

Availability bias makes us copy recent or vivid examples rather than the full context.
Ask whether you understand someone's whole situation before copying their financial choices.

INSIGHT

Use Geometric Averages For Real Returns

Use geometric (compound) averages, not arithmetic averages, to represent investment returns.
Arithmetic means overstate returns when volatility exists and can mislead planning and product marketing.

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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.