Powered by RND
PodcastsBusinessPersonal Finance for Long-Term Investors - The Best Interest

Personal Finance for Long-Term Investors - The Best Interest

Jesse Cramer
Personal Finance for Long-Term Investors - The Best Interest
Latest episode

Available Episodes

5 of 116
  • 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 [email protected] 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.  
    --------  
    1:03:56
  • 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 [email protected] 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.
    --------  
    1:20:45
  • Reset Your Portfolio Expectations, Before It's Too Late | Peter Lazaroff - E112
    Jesse welcomes back Peter Lazaroff to discuss the psychology and strategy of investing during uncertain times. They explore how media narratives and recession fears can distort investor behavior, emphasizing the importance of focusing on business earnings rather than sensational headlines. Peter shares why he separates his portfolio thinking from his balance sheet management, especially during potential economic downturns, and offers practical guidance for both pre-retirees and younger investors. The conversation also touches on international diversification, sequence of returns risk, and why consistency in strategy beats chasing performance. Plus, Peter gives an update on his podcast and his upcoming book The Perfect Portfolio. Key Takeaways: • Media headlines and algorithm-driven news feeds often amplify fear, leading investors away from rational, long-term thinking. • Real-world economic pain doesn’t always correlate with poor stock performance, and vice versa. A stock market decline doesn’t necessarily signal a broader economic recession. • Building a cash buffer ahead of retirement helps mitigate sequence of returns risk. • Global diversification may not always boost returns, but it smooths out the ride, improving compound returns. • A longer-term view of markets and recessions builds resilience and patience. • Planning for a range of outcomes is more effective than trying to call the next market move. Key Timestamps: (03:00) The Gladiator Analogy: Embracing Volatility (04:26) Setting Realistic Investing Expectations (06:17) Fire Drills for Your Portfolio (09:38) A Letter to Myself: Handling Market Crashes (14:36) Peter Lazaroff Joins the Conversation (27:15) Understanding the Emotional Side of Investing (29:39) The Importance of Documenting Investment Decisions (32:14) The Impact of News Narratives on Investment Decisions (41:23) Recession and Its Effects on Your Portfolio (46:53) International vs. Domestic Investments 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://peterlazaroff.com/ LinkedIn: https://www.linkedin.com/in/peterlazaroff/ Mentions: Peter's Book: https://peterlazaroff.com/freebook Are You Not Entertained?  https://bestinterest.blog/are-you-not-entertained/ Break Glass in Case of Market Crash?  https://bestinterest.blog/break-glass-market-crash/ More of The Best Interest: Check out the Best Interest Blog at https://bestinterest.blog/ Contact me at [email protected] 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.  
    --------  
    54:45
  • When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111
    Today’s episode is a special bonus episode, a companion to Jesse’s discussion on episode 555 of ChooseFI! Jesse examines the risks of over-optimization in personal finance, concentrating on tax-loss harvesting, asset allocation, Roth conversions, and dividend investing. He explains how each strategy can offer value when used thoughtfully, but warns that many DIY investors misuse them—chasing tax savings or popular tactics without considering the bigger financial picture. Jesse explains why tax loss harvesting often yields minimal or neutral benefits, how asset allocation offers modest long-term gains but can introduce liquidity and planning issues, and why Roth conversions only make sense with clear tax arbitrage. He also debunks common myths around dividend investing, emphasizing that total return—not dividend yield—should guide investment decisions. Key Takeaways: • Tax loss harvesting can be useful, but often delivers neutral or negligible long-term benefits when misapplied. • Most DIY investors use tax loss harvesting simply to avoid taxes now, without true tax arbitrage benefit. • Doing Roth conversions just to “get more money into Roth” can actually increase overall taxes unnecessarily. • Dividend investing is not inherently superior and often relies on poor logic or misunderstood benefits. • Total return—including dividends and capital gains—should guide investment decisions, not just dividend yield. • Bonds are more tax-inefficient than stocks and are ideally held in tax-advantaged accounts. Key Timestamps: (04:15) - Defining financial independence (09:44) - Early access to retirement accounts (21:59) - Tax loss harvesting explained (29:47) - Capital gains and FI community considerations (31:43) - The pitfalls of over-optimizing tax losses (37:08) - Benefits and downsides of asset allocation (46:22) - Roth conversions: When do they make sense? (49:00) - Debunking the myths of dividend investing (59:21) - Conclusion 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 [email protected] 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.
    --------  
    1:00:06
  • Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110
    Jesse explores the timeless wisdom of Warren Buffett, highlighting both his disciplined investment philosophy and his unwavering emphasis on trust and character. Jesse breaks down Buffett’s approach to buying great businesses at fair prices, holding them long-term, and focusing on intrinsic value, margin of safety, and staying within one’s circle of competence. He also examines Buffett’s early warnings about derivatives as speculative tools that undermine market integrity, and how Buffett built Berkshire Hathaway not just through smart investing, but through a foundation of honesty, patience, and reputation. It’s a masterclass in both investing and living with principle. This is essential listening for any long-term investor. Key Takeaways: • Buffett’s strategy is rooted in rational behavior, long-term thinking, and ignoring short-term market noise. • Berkshire Hathaway’s success is largely driven by acquiring whole companies and investing in businesses with strong fundamentals and leadership. • Buffett’s “circle of competence” encourages investors to focus only on areas they truly understand, rather than pretending to know it all. • Buffett’s legacy is built as much on ethics as on economics, showing that consistent honesty and long-term thinking pay off in every area. • Buffett rejects the Efficient Market Hypothesis (EMH), arguing that markets are often irrational and can be outsmarted with discipline and patience. • Jesse ties Buffett’s lessons back to personal finance and life, reminding listeners that reputation, trust, and a patient mindset are moats we can all build—no billions required. Key Timestamps:(02:16) - The benefits of long-term thinking (04:49) - Understanding your circle of competence (08:11) - The concept of intrinsic value (13:29) - The margin of safety principle (19:13) - Buffett's view on market inefficiencies (25:28) - The concept of economic moats (32:09) - Buffett's critique of derivatives (37:49) - The importance of trust and reputation (43:25) - Conclusion and final thoughts 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 bestinterest.blog Contact me at [email protected] 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.  
    --------  
    44:09

More Business podcasts

About Personal Finance for Long-Term Investors - The Best Interest

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.
Podcast website

Listen to Personal Finance for Long-Term Investors - The Best Interest, REAL AF with Andy Frisella and many other podcasts from around the world with the radio.net app

Get the free radio.net app

  • Stations and podcasts to bookmark
  • Stream via Wi-Fi or Bluetooth
  • Supports Carplay & Android Auto
  • Many other app features
Social
v7.23.3 | © 2007-2025 radio.de GmbH
Generated: 8/31/2025 - 11:04:36 AM