

Personal Finance for Long-Term Investors - The Best Interest
Jesse Cramer
Why is personal finance so complicated?
The internet is flooded with personal finance “experts” sharing short-sighted, error-prone advice. But long-term financial success requires thoughtful, patient, and well-researched strategies.
Hosted by Jesse Cramer, a former aerospace engineer turned fiduciary financial advisor in Rochester, NY, Personal Finance for Long-Term Investors simplifies complex financial topics. With relatable stories, in-depth research, and practical tips, Jesse helps you master financial planning for families, make smart decisions about tax-efficient investing, and build strategies for retirement planning and beyond.
Formerly known as The Best Interest Podcast, and inspired by Jesse’s award-nominated blog The Best Interest, this podcast is your trusted resource for comprehensive financial planning and smart investing.
Whether you're looking for optimal investment allocations, retirement planning advice, or generational wealth transfer ideas, this show makes personal finance approachable, enjoyable, and actionable.
A richer tomorrow starts with learning today. Invest in your knowledge with Personal Finance for Long-Term Investors.
The internet is flooded with personal finance “experts” sharing short-sighted, error-prone advice. But long-term financial success requires thoughtful, patient, and well-researched strategies.
Hosted by Jesse Cramer, a former aerospace engineer turned fiduciary financial advisor in Rochester, NY, Personal Finance for Long-Term Investors simplifies complex financial topics. With relatable stories, in-depth research, and practical tips, Jesse helps you master financial planning for families, make smart decisions about tax-efficient investing, and build strategies for retirement planning and beyond.
Formerly known as The Best Interest Podcast, and inspired by Jesse’s award-nominated blog The Best Interest, this podcast is your trusted resource for comprehensive financial planning and smart investing.
Whether you're looking for optimal investment allocations, retirement planning advice, or generational wealth transfer ideas, this show makes personal finance approachable, enjoyable, and actionable.
A richer tomorrow starts with learning today. Invest in your knowledge with Personal Finance for Long-Term Investors.
Episodes
Mentioned books

Oct 8, 2025 • 1h 27min
The Only Free Lunch in Investing (Maybe) | AMA #9 - E118
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.

23 snips
Oct 1, 2025 • 1h 6min
Military Money Lessons That Civilians Can’t Afford to Miss | Spencer Reese - E117
Spencer Reese, an Air Force veteran and financial educator, shares valuable insights for both military and civilian audiences. He discusses the evolving nature of retirement and the importance of a mindset focused on purpose and community. Spencer highlights financial lessons like avoiding lifestyle creep, managing expenses, and leveraging government benefits. He emphasizes communications systems for families, simplifying finances, and preparing for identity shifts post-service. Ultimately, he shows that financial independence is more than just numbers; it's about finding meaning.

5 snips
Sep 17, 2025 • 1h 9min
Manage *Yourself* More Than Your Portfolio | Hanna Horvath - E116
In this engaging conversation, Hanna Horvath, a Certified Financial Planner and managing editor at Bankrate, delves into the intriguing psychology of money. She explains how childhood experiences shape our financial habits and the importance of emotional discipline over mere willpower. Listeners learn about the identity shifts that retirement can bring and how to manage anxiety during this transition. With practical advice on preparing for market volatility and reframing our financial mindset, Hanna emphasizes that true wealth comes from awareness and intentionality.

8 snips
Sep 3, 2025 • 1h 10min
Where Investors Go Wrong: Tax Traps, Math Mistakes, and Behavioral Biases - E115
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.

Aug 20, 2025 • 1h 4min
The Risks and Rewards of Quitting Your Career | Kelan Kline - E114
Today, Jesse is joined by Kelan Kline, co-founder of The Savvy Couple, who shares his entrepreneurial journey from working as a jail deputy to building a successful online personal finance brand, emphasizing the importance of leveraging scalable income streams to achieve financial freedom. Kelan explains how entrepreneurship allows for more growth compared to a traditional nine-to-five by leveraging time, tools, and teams, and recounts how he and his wife carefully planned their transition by budgeting, paying off debt, and building a safety net before he quit his job. Kelan advocates starting with side hustles, particularly online opportunities like affiliate marketing, which offer flexibility and scalability, especially for people with limited time. He stresses the power of niching down to serve specific audiences deeply and shares lessons learned about the dangers of chasing shiny objects versus focusing on clear goals. Finally, he shares how they’ve diversified their income by expanding into real estate and pivoting toward AI-driven content creation, while building community initiatives like Freedom Builders to help others align their vision and master money on the path to financial independence. Key Takeaways: • Focus on high-leverage activities that maximize your time and financial return. • Niching down allows you to serve a specific audience better and grow faster. • Consistency and focus trump chasing every shiny new opportunity in entrepreneurship. • Risk-taking is necessary but should be balanced with a solid financial foundation. • Avoid multitasking across too many projects to prevent burnout and loss of focus. • Creating value first, then monetizing, is the key to sustainable online business growth. Key Timestamps: (00:00) - Financial Flexibility: The Key to Success (09:38) - Does Money Buy Happiness? (17:50) - Felicia's Inheritance: A Case Study (31:52) - Welcoming Kelan Kline (36:23) - Quitting the Job and Going Full-Time (38:01) - Evaluating Entrepreneurship: Is It Right for You? (42:31) - Risk Management in Entrepreneurship (47:39) - Diversifying Income Streams (59:32) - The Importance of Focus and Avoiding Shiny Object Syndrome (01:01:48) - Freedom Builders: A New Venture 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://thesavvycouple.com/ LinkedIn: https://www.linkedin.com/in/kelan-kline/ Mentions: https://thesavvycouple.com/start/ https://bestinterest.blog/financial-flexibility/ https://bestinterest.blog/two-roads-to-financial-independence/ https://bestinterest.blog/inheritance/ 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.

Aug 6, 2025 • 1h 21min
How to Be Smart About Inheritance Planning | AMA #8 - E113
Jesse tackles six thoughtful listener questions spanning a range of personal finance topics. He begins with a question about using Social Security and pension payments as a means to replace bonds in a retirement portfolio. Why do we own bonds, anyway? Then Jesse dives into long-term care insurance, a common sticky topic for aging retirees. Do they need to earmark dollars for long-term care? Next, he covers the taxation and distributions of inheritance assets, including sub-topics like probate, beneficiaries, trusts, and general estate planning tactics. He then covers equity compensation, breaking down RSUs, ISOs, NSOs, and ESPPs, and offers best practices for tax planning, diversification, and aligning with long-term goals. Mike then asks whether to invest $200,000 in cash currently sitting in a money market fund; Jesse outlines rational reasons for holding cash but warns against market timing, instead recommending a disciplined monthly investment plan. Finally, Paul inquires about the interaction between RMDs and sequence of returns risk, and Jesse reassures that while the concern is valid, proper planning—including Roth conversions, diversified withdrawals, and long-term strategy—can neutralize the potential damage. Key Takeaways: • Diversify your exposure—holding too much company stock can increase risk, so it’s often wise to sell and reinvest elsewhere once vesting or exercise occurs. • Planning ahead can reduce reliance on penalties or rigid strategies—consider building a taxable or Roth account alongside retirement funds. • Investors tend to lose more trying to time downturns than they do by staying invested through them. • Your plan should balance growth and stability, aiming to avoid forced sales in down markets while still meeting long-term goals. Key Timestamps: (00:00) - Diversification and Bonds in Retirement Portfolios (07:47) - Expectations for Stocks vs. Bonds (11:08) - Long-Term Care Insurance Deep Dive (25:08) - Taxation and Distribution of Inheritance Assets (38:49) - Revocable vs. Irrevocable Trusts: Control and Tax Implications (41:12) - Trust Distribution and Taxation (45:19) - Equity Compensation: RSUs, ISOs, NSOs, and ESPPs (51:49) - Best Practices for Managing Equity Compensation (59:28) - Market Timing and Cash Management Strategies (01:07:25) - RMDs and Sequence of Returns Risk 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/asset-liability-matching-aligns-your-money-to-your-future/ https://bestinterest.blog/all-ask-me-anything-ama-episodes/ 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.

6 snips
Jul 23, 2025 • 55min
Reset Your Portfolio Expectations, Before It's Too Late | Peter Lazaroff - E112
Peter Lazaroff, Chief Investment Officer at PlanCorp and host of The Long-Term Investor podcast, dives into the psychology of investing amid uncertainty. He highlights how media narratives can skew perceptions and urges a focus on business earnings. Peter discusses the importance of separating portfolio management from balance sheet concerns during downturns. He shares strategies for building a cash buffer before retirement and emphasizes the value of global diversification. Consistency in investment strategies is key, as is resilience in the face of market volatility.

Jul 14, 2025 • 1h
When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111
Discover how over-optimization can backfire in personal finance. Learn about the risks of tax-loss harvesting and why it often yields minimal benefits when misapplied. Explore the complexities of Roth conversions and how they can unintentionally increase taxes. Jesse reveals that dividend investing isn't necessarily superior, emphasizing the importance of total return over mere yield. The conversation delves into asset allocation strategies and the hidden pitfalls of managing investments, urging a holistic view for long-term success.

8 snips
Jul 2, 2025 • 44min
Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110
Explore Warren Buffett's investment wisdom, focusing on long-term strategies and intrinsic value. Discover the importance of a margin of safety during market volatility and how to navigate irrational markets. Learn about the balance between concentration and diversification, and the value of economic moats. Trust and reputation emerge as foundational elements in successful investing, contrasting with the fleeting nature of market trends. This rich discussion serves as a guide for both investors and those seeking a principled life.

10 snips
Jun 18, 2025 • 50min
Scrimping, Splurging, and Other Crazy Spending Stories - E109
Join humorist Joe Saul-Sehy from Stacking Benjamins and Bill Yount from Catching Up to FI as they discuss financial priorities. They dive into the iceberg principle of stealth wealth, emphasizing that true riches often lie in what you don't spend. Joe shares amusing anecdotes about financial mishaps, while Bill highlights the evolving nature of spending through life’s seasons. Together, they explore how our emotional ties to money affect our choices, encouraging listeners to align spending with personal values for greater satisfaction.