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.

Jesse answers listener questions on financial planning, investment management, and retirement. He discusses the challenges of rising homeowner’s insurance costs in high-risk areas, the differences between Treasuries, CDs, and high-yield savings accounts, and the inefficiencies of using life insurance for tax-free retirement. He advises Casey, a future retiree, on tax-efficient withdrawal strategies and investment choices, and guides Chris, a federal worker, on pension decisions, TSP management, and career changes. Jesse also addresses Rachel’s concerns about bond funds versus individual bonds, explaining their similarities and recommending a goals-based portfolio approach with cash reserves and an appropriate bond allocation for retirement security. Throughout the episode, he emphasizes strategic financial planning and adaptability in decision-making.

Key Takeaways:
• Homeowner’s insurance costs are rising in high-risk states like California and Florida due to natural disasters.
• We explore the ethical dilemma over whether wealthy homeowners should receive government aid after disasters.
• Treasuries, CDs, and high-yield savings accounts differ in liquidity, risk, and how financial institutions set rates.
• Permanent life insurance strategies like whole life and indexed universal life are marketed as tax-free retirement solutions but are often inefficient.
• When planning your retirement, future required minimum distributions (RMDs) should be considered, as pre-tax accounts will be taxed upon withdrawal.
• Career risk should be assessed by weighing long-term benefits against short-term uncertainties, emphasizing planning and adaptability.

Key Timestamps:
(00:00) Introduction to Personal Finance for Long-term Investors
(01:40) Question 1: California Wildfires and Financial Planning
(06:57) Government Intervention in Insurance
(13:21) Question 2: Treasuries, CDs, and High Yield Savings Accounts
(21:09) Question 3: Tax-Free Retirement Strategies
(29:46) Question 4: Retirement Planning with Part-Time Work
(33:49) Pros and Cons of Realizing Capital Gains
(36:06) Question 5: Federal Government Pension Dilemma
(42:33) Career Change Risks and Rewards
(48:46) Question 6: Bonds vs. Bond Funds

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:
Career Change – Is It A Risk?: https://bestinterest.blog/career-change-risk/

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 educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse Cramer speaks with Christine Benz, Director of Personal Finance at Morningstar, about insights from her book How to Retire. Before their discussion, Jesse contrasts gambling with long-term investing, emphasizing the risks of short-term market bets versus the reliability of patient investing. Christine highlights the shift in financial advice toward holistic retirement planning, including the importance of low-cost, diversified portfolios and planning for life transitions. The episode also explores the financial impact of caregiving, particularly on women, and the necessity of proactive retirement savings and long-term care planning. John Guyton’s "guardrails approach" is discussed as a strategy for adjusting withdrawals based on market performance. Additionally, the conversation underscores the role of psychology in financial decision-making and the non-financial aspects of retirement, such as maintaining social connections and redefining work-life balance. The overarching message is that successful retirement planning requires a combination of careful financial preparation, behavioral awareness, and long-term strategic thinking.

Key Takeaways:
• Short-term stock market movements may seem random, but long-term investing historically trends upward, making it a safer and more strategic approach compared to gambling.
• Many people underestimate their lifespan, which can lead to financial shortfalls in retirement; actuarial data and family history should be factored into planning.
• Persuasive stories can shape financial decision-making, sometimes leading people to overlook critical advice in favor of compelling but misleading pitches.
• Taking on unpaid caregiving roles can impact financial security, and couples should consider financial agreements to ensure fair distribution of assets.
• Beyond finances, maintaining social connections and finding purpose are crucial for a satisfying retirement.
• A successful retirement is not just about financial security but also about ensuring a meaningful and well-balanced life in later years.

Key Timestamps:
(00:00) Casino vs. Investment
(11:09) Understanding Life Expectancy for Retirement
(15:29) The Man Who Never Looked Up
(20:41) Interview with Christine Benz
(23:06) The Shift to Holistic Planning
(23:47) Consumer Investment Preferences
(24:26) Christine's Book: How to Retire
(25:04) Personal Story: Christine's Parents
(27:16) The Role of Financial Planners
(30:24) Flexible Financial Planning Models
(39:46) Retirement Planning for Women
(45:28) Navigating Retirement as a Couple
(47:24) Insights from The Long View Podcast
(49:17) Conclusion and Contact Information

Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance

Mentions:
Website: https://www.morningstar.com/podcasts/the-long-view

LinkedIn: https://www.linkedin.com/in/christine-benz-b83b523/

Mentions:

https://bestinterest.blog/how-long-will-you-live/

https://bestinterest.blog/some-bets-im-willing-to-make/

https://bestinterest.blog/the-man-who-never-looked-up/

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 educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Today we take a look at the U.S. national debt, distinguishing it from household debt and analyzing its impact on individuals and investors. Jesse traces the debt’s history and explains its structure, funding through Treasury bonds, and refinancing process. The discussion covers Modern Monetary Theory (MMT), which suggests that as a currency issuer, the U.S. cannot default but must manage inflation through taxation—though critics question the feasibility of this approach. While deficit spending can drive economic growth, excessive money printing may erode investor confidence. Interest rates play a crucial role in borrowing, investment, and market stability. Inflation, influenced by national debt and monetary policy, erodes cash and bond values, making stocks a stronger long-term hedge. Real estate may also help, but with mixed results. Despite the complexities of national debt, a diversified investment strategy and career growth offer the best approach to financial stability.

Key Takeaways:
• The U.S. government operates under different financial rules than a household, as it can issue its own currency and refinance debt indefinitely.
• From $75 million after the Revolutionary War to $36 trillion in 2025, national debt has always played a role in economic growth and policy.
• Debt is split into intra-governmental (owed within the government) and publicly held (owed to investors, institutions, and foreign entities).
• The Federal Reserve influences borrowing costs by setting interest rates, affecting everything from government debt payments to personal loans.
• Printing money doesn’t cause default, but it can devalue currency and increase prices, impacting purchasing power.
• Spreading investments across different asset classes helps mitigate risk and combat inflationary pressures.

Key Timestamps:
(00:00) Understanding the U.S. National Debt
(02:14) Components of the National Debt
(07:55) The Role of the Federal Reserve
(14:40) Modern Monetary Theory Explained
(17:58) Criticisms of Modern Monetary Theory
(26:41) Implications for Personal Finance
(32:03) Combating Inflation and Taxes
(39:18) 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, Modern Monetary Theory, national debt, diversification

Mentions:
https://bestinterest.blog/what-investments-actually-beat-inflation-since-2020/

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 educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

Jesse is joined by Chad Carson, who discusses residential real estate investing as a stable alternative to stocks and bonds. While real estate offers advantages like rental income, property appreciation, and tax benefits, Jesse also highlights challenges such as high costs, tenant issues, liquidity problems, and the time commitment required. Jesse thinks of his Rochester wealth management clients, and what some of them do.

Chad emphasizes choosing the right location, focusing on properties with minimal renovation needs, and securing financing that ensures a healthy cash flow. He advises new investors to avoid risky locations and avoid over-leveraging, recommending a steady, cautious approach. The discussion also touches on the stages of investing, from securing initial deals to building wealth and prioritizing stability.

The concept of the "small and mighty" investor is introduced, suggesting that a smaller, well-managed portfolio can generate significant passive income, offering more flexibility and freedom than large-scale investing. Both Jesse and Chad stress the importance of aligning investments with personal values and goals, encouraging listeners to prioritize lifestyle over asset accumulation - a pillar of financial planning.

Key Takeaways:
• When investing in real estate, focus on areas with strong job markets and potential for growth. Avoid declining populations and single-industry towns.
• Ensure mortgage payments are significantly lower than your rental income, ideally aiming for a 50% or lower mortgage-to-rent ratio.
• Mortgages allow for property ownership you couldn’t otherwise afford, but use debt carefully, especially in downturns. Ensure good debt management to avoid financial failure.
• Whether through books, podcasts, or coaches, learning from experts can help build confidence and avoid mistakes.
• Bigger isn’t always better. A smaller, well-managed portfolio can generate significant passive income without the burden of managing hundreds of units.
• Real estate should fit into your personal values and long-term lifestyle vision. Success is not about accumulating assets but achieving your desired way of life.

Key Timestamps:
(00:00) Introduction to Personal Finance for Long Term Investors
(02:23) The Power of Leverage in Real Estate
(07:35) Cons of Residential Real Estate Investing
(15:02) Introducing Coach Chad Carson
(17:01) Choosing the Right Real Estate Location
(28:26) Understanding the Three Rental Stages
(29:09) The Importance of Debt Management
(31:51) Balancing Real Estate with a Busy Life
(40:16) The Small and Mighty Real Estate Investor
(45:56) Finding Your 'Enough' in Real Estate
(51:32) Conclusion and Resources

Key Topics Discussed:
Personal Finance for the Long-Term Investor, The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, real estate, Chad Carson, leverage, debt, mortgage, Coach Carson

Mentions:
Website: https://www.coachcarson.com/
LinkedIn: https://www.linkedin.com/in/coachcarson/

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 educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.