Personal Finance for Long-Term Investors - The Best Interest

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. • Paying off a mortgage early is more about peace of mind than maximizing returns—there’s emotional value in being debt-free. • Flexibility and control often make 529s a better choice, but UTMAs can be useful for broader non-educational goals. • 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.

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.

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.

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.

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.

Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for high earners, healthcare in retirement, and investing during economic uncertainty. He explains that heirs to traditional IRAs must pay income tax on withdrawals, while taxable accounts benefit from a step-up in basis, and argues that whole life insurance is generally a poor investment choice for most people. He outlines how married couples enjoy more financial advantages due to shared costs, tax benefits, and retirement perks, though singles benefit from greater autonomy. A high-earning listener weighing Roth versus traditional retirement contributions is advised to consider tax-bracket arbitrage in retirement or hedge with a 50/50 split. Jesse also dives into healthcare planning, covering employer plans, HSAs, COBRA, ACA subsidies, and Medicare, while stressing the complexity and importance of planning for long-term care. On investing, he cautions against trying to time recessions and emphasizes aligning investment strategies with individual goals, risk tolerance, and time horizons. Key Takeaways:• Traditional IRAs require heirs to pay income tax on withdrawals within 10 years, but this is deferred tax, not a penalty. • Whole life insurance is generally more expensive and offers lower returns than term insurance plus independent investing. • Married couples often benefit financially from economies of scale and joint tax advantages. Single individuals have greater financial control and simpler planning but may miss out on some systemic benefits for couples. • Healthcare planning is a critical but often overlooked aspect of retirement financial planning. Jesse discusses ACA, COBRA, and HSAs. • Short-term market volatility can be misleading; experiencing real losses helps build long-term investing discipline. • Selling stocks to avoid recession dips is risky because market recoveries often precede economic improvements, resulting in missed gains. Key Timestamps:(00:00) Question 1: Whole Life Insurance (17:47) Question 2: Financial Pros and Cons of Being Single vs. Married (27:19) Question 3: Roth vs. Traditional Accounts (37:54) Question 4: Planning for Healthcare Costs in Retirement (42:31) Maximizing HSA Growth with a Strategic Loophole (45:08) COBRA and ACA for Early Retirees (53:48) Medicare: Breaking Down the Basics (01:03:02) Question 5: Investment Strategies During Economic Uncertainty 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/is-benefits-hacking-genius-or-immoral/ Deep Risk: How History Informs Portfolio Design by William J. Bernstein More of The Best Interest:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog 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 Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-retirees about misleading sales tactics that exploit fear - especially the fear of market losses. They emphasize the importance of working with fee-only, fiduciary advisors who are legally obligated to act in clients' best interests, in contrast to commission-based salespeople who often obscure fees, misrepresent guarantees, and use charm to build trust. Drawing from Jason Zweig’s “19 Questions to Ask Your Financial Advisor,” Jesse highlights key criteria for evaluating advisors, including transparency, credentials, investment philosophy, and service scope. They condemn opaque fee structures, sales contests, and annuity marketing tactics - like steak dinners that pressure attendees into high-commission products - and describe most annuities as complex, wealth-threatening vehicles. Jesse adds practical suggestions like inquiring about an advisor’s succession plan, communication style, and client load, and stresses the value of education and evidence-based investing. The two advocate for comprehensive financial planning and alignment of advisor-client interests, with Don underscoring the importance of commitment to honesty, transparency, and fiduciary duty. Key Takeaways:• Annuity and investment salespeople often exploit retirees' fear of losing money in market downturns to sell high-fee products. • While there are niche use cases, many annuity products are expensive, opaque, and designed to benefit the seller more than the buyer. • You need to know what happens to your financial relationship if your advisor retires or leaves. • State-level oversight often fails to protect consumers from misleading practices. • Know the difference between moral fiduciary responsibility and legal fiduciary responsibility. • It’s a red flag if an advisor recommends products they wouldn’t use for themselves. Key Timestamps:(00:00) Understanding Annuities and Financial Advisors (02:08) 19 Questions to Ask Your Financial Advisor (08:13) Conflicts of Interest in Financial Advising (12:56) Investment Philosophy and Market Timing (18:34) Professional Credentials and Requirements (23:07) Additional Questions for Your Financial Advisor (29:05) The Gamble of Annuities (34:34) The Deceptive World of Indexed Annuities (36:17) The Ethics of Financial Advisors (39:29) The Lack of Federal Oversight (46:38) Misleading Sales Tactics (49:42) Advice for Annuity Holders and Seekers (56:45) Don McDonald's Financial Talk Show 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://talkingrealmoney.com/ LinkedIn: https://www.linkedin.com/in/donmcdonald/   More of The Best Interest:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog 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 explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning into retirement, especially those aged 50 to 75. With half of the participants recently retired and the other half preparing to retire within two years, the study offers a timely look at the "final glide path" into retirement and the early years that follow. Authored by retirement experts Fritz Gilbert and Eric Weigel, the report dives into preparedness, lifestyle satisfaction, and evolving concerns. It reveals a common disconnect between what pre-retirees expect and what retirees actually experience—particularly around health, identity, and social engagement. Jesse discusses how meaning and purpose often decline post-retirement, and how maintaining social connection and physical health is key to thriving. Drawing inspiration from longevity expert Dr. Peter Attia, the episode emphasizes that preparing for retirement goes beyond money—it’s about planning for purpose, relationships, and well-being. Jesse also shares three powerful exercises to help listeners create a more intentional retirement vision: the Perfect Day, the Ikigai Map, and the Rocking Chair Test. Key Takeaways:• Retirement is more than a financial event—it's a major life transition requiring emotional, social, and identity planning. • Physical health and vitality are crucial to enjoying retirement, not just surviving it. • Social connection is one of the strongest predictors of well-being in retirement. • The “Perfect Day” exercise helps retirees envision and plan a fulfilling daily life post-career. • The “Ikigai Map” offers a powerful framework to align purpose, passion, and impact in retirement. • The “Rocking Chair Test” encourages long-term reflection on what truly matters at the end of life. Key Timestamps:(00:00) Diving into the Retirement Perspectives and Attitudes Survey (04:22) Finding Purpose and Meaning in Retirement (10:26) Adhering to a Healthy Lifestyle (13:49) Creating a Clear Vision and Plan for Retirement (21:12) Biggest Differences Between Pre and Post Retirees 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://www.retirewithpossibilities.com/wp-content/uploads/2023/05/Retirement-Perspectives-and-Attitudes-Survey-May-2023.pdf  More of The Best Interest:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog 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 explores the financial journey of late starters with guest Bill Yount, co-host of Catching Up to FI. In the opening monologue, Jesse shares his “Stupidly Simple Secret Sauce” for personal finance: spend less than you earn, grow income without inflating lifestyle, invest consistently, and prioritize savings. He warns against flashy success stories, consumer culture, and speculation, instead advocating for steady, index-fund investing and disciplined budgeting. The episode also addresses market volatility and debunks the “buy the dip” strategy, showing that long-term consistency outperforms timing attempts. Bill shares his compelling story of waking up to his finances at age 50, shifting from paycheck-to-paycheck living to a 40% savings rate and near financial independence. He emphasizes emotional readiness, sustainable planning, and community support for those starting late. Whether you're in your 30s, 50s, or beyond, this episode delivers practical, empowering advice for reclaiming your financial future. Key Takeaways:• The core rules of personal finance are deceptively simple: spend less than you earn, earn more without inflating your lifestyle, and invest consistently. • Boring, steady investing (like index funds) usually beats market timing or speculative bets. • Many late starters carry emotional baggage around money, but those feelings can become fuel for change. • After the excitement of getting started, real progress is made through slow, steady work over years. • Taking full responsibility for your finances brings peace of mind, even if the numbers aren’t pretty at first. • With a solid plan, cutting expenses, and investing consistently, it’s doable. Key Timestamps:(00:00) The Stupidly Simple Secret Sauce of Personal Finance (04:58) The Winners are Loud, but the Losers Stay Silent (06:42) Boring is Best: The Case for Index Funds (10:46) The Story of Dave: A Financial Cautionary Tale (15:30) Market Volatility and the Concept of Buying the Dip (25:02) Facing Financial Realities with Bill Yount (29:48) Creating a Financial Plan (35:07) Late Starters and Financial Freedom (39:56) The Role of Social Security (48:51) Investment Advice for Late Starters (56:00) Building a Financial Community 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://catchinguptofi.com/ CUTFI’s Facebook group:  https://www.facebook.com/groups/catchinguptofi/ LinkedIn: https://www.linkedin.com/company/catchinguptofi/  Mentions: https://bestinterest.blog/secret-sauce/ https://bestinterest.blog/dave/ https://bestinterest.blog/buy-the-dip/ https://bestinterest.blog/is-tax-loss-harvesting-worthwhile/   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog 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 critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while promoting disciplined, evidence-based strategies. Tariffs, though intended to protect domestic industries, often raise prices and stoke inflation, ultimately harming consumers, businesses, and investor sentiment, with economists warning they may slow growth or trigger stagflation. Market reactions, such as those seen during the Trump-era tariffs, highlight investor uncertainty and the self-inflicted nature of such economic disruptions. Jesse offers 15 introspective questions to help investors stay grounded, assess their emotional triggers, and focus on long-term goals rather than panic-driven moves like tax-loss harvesting or "buying the dip." He critiques the celebratory tone around recessions and urges against using emergency funds for speculative gains, emphasizing that such attitudes overlook the human cost of downturns and risk mispricing assets. Ultimately, the message is clear: successful investing demands self-awareness, patience, and preparation—not market timing, blind optimism, or short-term emotional decisions. Key Takeaways:• Tariffs are essentially taxes on imports aimed at protecting domestic industries and gaining leverage in trade negotiations. While intended to boost local economies, tariffs often have unintended consequences, such as raising consumer prices. • Long-term investment strategies like diversification and rebalancing remain important, even during market turbulence caused by tariffs. • The "buy the dip" mentality is flawed, especially if it involves tapping emergency funds or relying on hope over planning. • Assuming “markets always recover” can lead to complacency and distorted risk-reward expectations. • Rational, emotionally detached investing leads to better outcomes than strategies based on fear or overconfidence. • Successful investing hinges on preparation and humility, not certainty or bravado—acknowledging the market’s unpredictability is key. Key Timestamps:(00:00) Market Update and Tariff Discussion (02:00) Impact of Tariffs on the Market (13:33) 15 Questions for Scared Investors (22:19) Understanding Portfolio Reactions to Market Events (27:15) The Fallacy of Buying the Dip (28:48) Emotional Investing and Market Realities (36:20) The Myth of Guaranteed Market Recovery 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/the-15-tariff-questions-ive-heard-most/  https://bestinterest.blog/15-questions-for-scared-investors-right-now/ https://bestinterest.blog/let-them-trade-stocks/ https://bestinterest.blog/last-weeks-terrific-real-life-stock-lesson/ https://bestinterest.blog/impossible-to-lose/  https://bestinterest.blog/roth-conversions/  https://bestinterest.blog/is-tax-loss-harvesting-worthwhile/  https://bestinterest.blog/markets-dont-always-recover/ More of The Best Interest:Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog 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.