The Best Interest - Personal Finance for Long-Term Investors

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

Why is personal finance so complicated? Even worse, the Internet is full of personal finance “experts” providing short-sighted, error-prone, and outright bad financial advice. Jesse Cramer has a knack for using everyday experiences to make personal finance accessible for the average investor. His extensive research coupled with skilled narrative makes personal finance actually enjoyable. By day, Jesse works for a fiduciary wealth management firm in Rochester, NY. By night, he runs The Best Interest - nominated in 2022 for "Personal Finance Blog of the Year.” The Best Interest simplifies personal finance and investing to make your life easier, smarter…and a little richer, too. Come invest in knowledge with The Best Interest.

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    The Bad “Money Scripts” Someone Else Wrote for You | Brad Klontz - E97

    Jesse kicks today’s show off with a monologue on the importance of having the right temperament for investing - it’s not really about intelligence at all. Emotional stability and disciplined decision making outweigh expertise and intelligence when investing. The Dunning-Kruger effect and the paradox of choice are also highlighted, emphasizing the need to prioritize action over perfection in personal finance. For the second half of the show, Dr. Brad Klontz, Co-Founder of the Financial Psychology Institute and author of Start Thinking Rich, joins to discuss “money scripts”, which are subconscious beliefs about money inherited from previous generations, our society, or other people we’re surrounded by. Throughout the conversation, the duo dispels myths about wealth, and makes a distinction between being “poor” (a limiting mindset) and being “broke” (a temporary financial state). The conversation gets deep into the stories we tell ourselves, how we present money, and how to adopt an internal locus of control and make lifestyle changes.  This episode is a must listen for anyone wanting to explore their own “money scripts” and rethink the way they talk to themselves - and others - about money. Key Takeaways: • How the Dunning-Kruger effect is affecting your investing decisions. • The difference between a satisficer and a maximizer - and why you may want to be the former. • What is a “money script”? And how can you change yours? • The patterns you may have inherited from even your great grandparents. • Consider how you rank on the following four patterns: avoidance, worship, vigilance, and status. • Research backed psychological insights about your relationship with money. Key Timestamps: (00:00) Understanding the Dunning-Kruger Effect (02:58) Insider vs. Outsider Perspectives in Sports and Investing (05:41) The Importance of Temperament in Investing (10:13) The Paradox of Choice and Financial Decision Making (18:07) Interview with Dr. Brad Klontz: Money Scripts and Financial Psychology (28:44) Understanding Money Scripts (30:42) Personal Reflections on Economic Backgrounds (33:33) Introducing the New Book: Start Thinking Rich (35:19) Harsh Truths About Wealth and Mindset (42:15) The Power of Locus of Control Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Brad Klontz, Start Thinking Rich, money scripts, financial psychology, limiting mindset, mindset growth, money myths, workaholic, workaholism, unhealthy patterns Mentions: Website: https://www.bradklontz.com/ LinkedIn: https://www.linkedin.com/in/drbradklontz/  Mentions: On Amazon: Start Thinking Rich: 21 Harsh Truths to Take You from Broke to Financial Freedom Great Investors’ Little Secret:  https://bestinterest.blog/great-investors-little-secret/ How “Analysis Paralysis” Can Sabotage Our Finances: https://bestinterest.blog/opportunity-paranoia-analysis-paralysis/ 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.

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    But is NOW the Right Time to Invest in the Stock Market?! - E96

    Talking solo, Jesse tackles two important, ever-present investing questions in today’s monologue. Should I try to time the market? How do I beat the market? The truth is, the timeless advice stands: diversify your portfolio, steer clear of speculation, and invest early and often. Diversifying is like buying the haystack, rather than looking for the needle, because, the truth is, you probably won’t find the needle. Speculative stock-picking is like picking out some straw and hoping it’ll turn out to be the needle. To illustrate the benefits of consistent investing - rather than attempted market timing - Jesse tells the tale of Bad Timing Bill, Normal Nick, and Good Timing Gary. Bill and Gary both tried to time the market. This episode is packed with insight you’ll want to return to again and again. Key Takeaways: • Don’t look for the needle in the haystack. Buy the haystack. Most stock pickers stumble into success. • There’s no such thing as skilled stock picking because we can never know the entire market. • Just because a business is massive and visible, doesn’t mean it will forever make good decisions. • How to sort out a fair price for something. A good burger isn’t worth 100 dollars! • What are CAPE and PE ratios? • The story of Bill, Nick, and Gary: Why you shouldn’t try to time the market.  Key Timestamps: (00:00) The Best Interest Year in Review (08:02) The Evergreen Question: Is Now the Right Time to Invest? (11:58) The Case for Index Investing (25:16) Understanding Market Efficiency (29:13) The Starbucks Dilemma: Diversification vs. Concentration (32:01) The Importance of Price (32:39) Warren Buffett's Wisdom on Fair Prices (33:37) The Risks of Overconcentration in a Single Stock (34:14) Diversification and Risk Management (35:36) The Concept of Timing the Market (36:08) The CAPE Ratio Explained (46:39) Dollar Cost Averaging vs. Lump Sum Investing (51:27) The Complexity of Market Movements Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, stock picking, speculation, index funds, mutual funds, stock market, DIY investing Mentions: Wealth Creation in the U.S. Public Stock Markets 1926 to 2019 by Hendrik Bessembinder https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3537838  The Needle in the Haystack:  https://bestinterest.blog/the-needle-in-the-haystack/ Yes, You Can Beat the Market, But...:  https://bestinterest.blog/yes-you-can-beat-the-market/ Good Company, Bad Stock:  https://bestinterest.blog/good-company-bad-stock/ The CAPE Ratio vs. Future Returns: https://bestinterest.blog/cape-vs-future-returns/ 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.

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    Tax Loss Harvesting Myths Debunked: What You Need to Know Now | AMA #4 with Jesse - E95

    Jesse is solo, answering your questions! Kate, a government worker with $650,000 in IRAs, is wondering how she can best rebalance her portfolio - and when. Dan seeks clarity on bonds' role despite recent poor returns, learning they offer portfolio stability and mitigate market volatility, critical for risk-averse investors. Peter asks about Social Security timing, highlighting the trade-off between early claiming's investment growth potential versus the guaranteed, low risk returns of delayed benefits, with traditional advice favoring security. Lucas, a young investor with a taxable brokerage account, asks about key considerations to include when setting up a dividend reinvestment plan. Lastly, Chris wonders how to judge between three potential advisors. If you’d like a question in a future AMA, send Jesse a message!   Key Takeaways: • How to mitigate your risk by diversification. • Why a 10% “sandbox” could be the right thing for your portfolio. • Should you employ a time based or an allocation based  rebalancing strategy. • When you should or should not use bonds. • What is “transfer-on-death”? • How to choose between financial advisors.   Key Timestamps: (00:00) - Review of the Week (01:15) - AMA: Portfolio Rebalancing (10:45) - AMA: Understanding Bond Performance (20:29) - The Role of Bonds in Inflation (25:59) - AMA: Social Security and Investment Strategy (29:37) - Understanding Risk-Adjusted Returns (30:32) - Comparing Social Security to Risk-Free Investments (32:37) - Potential Downsides of Early Social Security Collection (37:39) - Lucas's Taxable Brokerage Account Strategy (50:38) - Chris's Financial Advisor Dilemma   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Tax Loss Harvesting Myths, Debunked: What You Need to Know Now, The Simple 3-Step Formula to Avoid Excess Taxes in Your Investments, Is Splitting Your Portfolio Between Advisors a Smart Move? Maximize Your Capital Gains: Proven Tax Strategies for 2024, How to Avoid IRS Fines: The Urgent 90% Rule You Need to Know   Mentions: “Why Can’t I Take Social Security Early and Invest It?”  https://bestinterest.blog/why-cant-i-take-social-security-early-and-invest-it/  “I Wouldn’t Know Where to Start” – 16 Questions to Ask A Financial Advisor https://bestinterest.blog/financial-advisor-questions/    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.

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    Silly Hacks, New Rules, & Unpopular Opinions - E94

    Jesse’s running the show solo this week, bringing with him some interesting perspectives on tax tricks, whether you should rent or buy, and college education. In this episode, you’ll hear why side hustles might just be a waste of time, what makes detailed budgeting overrated, and how you’re actually spoiled just by having a queen sized bed! This episode is great if you’re looking for a few reminders, grounding advice, or a few different opinions. Key Takeaways: • Reasons why you shouldn’t rely solely on your stocks for your early retirement. • The 50% Rule for 529 College Savings Plans. • What makes a side hustle a waste of time? • Why renting might be the right decision. • How perspective shows you’re actually spoiled! • Is your advisor a professional? Or a hack? Key Timestamps: (02:51) Critique of the FIRE Movement (05:50) Debunking Tax Hacks (09:08) The 50% Rule for 529 Plans (13:22) Primary Home: Not an Investment (15:18) The Reality of Side Hustles (19:41) Rent vs. Buy: A Balanced View (25:21) Living a Life of Luxury (32:10) Reevaluating Detailed Budgeting (36:52) The Spectrum of Financial Advisors (41:38) Pay Yourself First, But Not Too Much (42:50) Essential Thoughts for True Wealth (46:02) Conclusion and Final Thoughts Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance Mentions: Factfulness: Ten Reasons We're Wrong About the World--and Why Things Are Better Than You Think by Hans Rosling, Anna Rosling Rönnlund, and Ola Rosling “I Wouldn’t Know Where to Start” – 16 Questions to Ask A Financial Advisor by Jesse Cramer 11 Essentials of Client Service 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.

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    Instructive and Surprising Questions to Ask Before You Retire | Joe Saul-Sehy - E93

    What are the long-term gains of educated investment decisions? The COVID pandemic triggered fear and uncertainty, with many wanting to sell everything amid the stock market's 30% drop. However, disciplined investors maintained their perspective and followed their investment policy. This approach, coupled with proper financial planning, often results in a stronger portfolio after market crashes, helping investors avoid costly mistakes. In contrast, a friend who sold his business for $10 million was initially hesitant to invest in the stock market due to a lack of education, but with advice to seek higher yields and follow a well-planned asset allocation strategy, he increased his earnings from 0.05% to 4.5% annually. Throughout Jesse’s monologue, he highlights examples where educated, deliberate, and disciplined decisions helped grow people’s portfolios and prepare them for their long-term goals. Joe Saul-Sehy of Stacking Benjamins, returns to the podcast for the second half of the show. Jesse and Joe each brought 5 questions to ask before retirement - ideally long before retirement. Alternating, back and forth, they discover how few of these questions are about money. Sound investment and retirement planning isn’t just about the number going up, but also about what you’re going to do with the money you accumulate. Many of us plan to enjoy plenty of golfing during retirement, but, who among us can say we’d like to golf every day for 20 years? Join Jesse and Joe on an exploration of the questions you need to ask when planning your retirement.   Key Takeaways: • Have you taken your mental and physical health into consideration when planning your retirement years? • How long do you expect to be retired? And what do you plan to do with your time? • Find something you can passionately be involved in during your retirement years. • Why “chasing kids” isn’t a great retirement plan. • How to simplify your savings plan and make the most of it. • What engineers can teach us about planning for the unknown unknowns.   Key Timestamps: (02:14) - Jesse’s Monologue: Putting a Dollar Sign on Financial Planning (07:23) - Car Loan Decision Making (08:24) - Backdoor IRA Contributions (10:11) - Choosing the Right Home Location (14:01) - Understanding Cash Balance Plans (20:48) - Interview: Joe Saul-Sehy (22:08) - Top Questions for Retirement Planning (37:40) - Creative Solutions for Health Insurance in Retirement (39:20) - Behavioral Aspects of Investing (41:26) - The Fee Wars and Financial Planning (45:36) - Asset Allocation and Investment Choices (48:45) - Health and Healthcare in Retirement (53:05) - Maintaining Relationships in Retirement (57:46) - Protecting Yourself in Retirement (01:01:06) - Giving Back to the Community (01:07:58) - Conclusion and Podcast Information   Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, retirement lifestyle, FIRE lifestyle, mental health, physical health   Mentions: Website: https://www.stackingbenjamins.com/ LinkedIn: https://www.linkedin.com/in/joe-saul-sehy-b3426b31/ What Retirees Want: A Holistic View of Life's Third Age by Ken Dychtwald and Robert Morison Keys to a Successful Retirement: Staying Happy, Active, and Productive in Your Retired Years by Fritz Gilbert   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.

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    Why Teachers Need to Be Careful | Dan Otter - E92

    Jesse opens the show by sharing a personal anecdote about a former teacher's challenging investment choices, which were burdened with high fees from their financial advisor. He emphasizes the predatory nature of the financial advice teachers receive, encouraging teachers to seek better investment options from reputable firms like Vanguard and Fidelity. Finally, Jesse underscores the importance of being informed against the systemic issues in the retirement planning landscape for educators. Dan Otter joins for the second half of the show. Dan is the co-founder of 403(b)Wise, which aims to make information about the 403(b) readily available to educators. Together, Dan and Jesse delve into the complexities and challenges of 403(b) retirement plans for public school teachers. They address the absence of Federal fiduciary protections, the prevalence of predatory financial options, and the stark differences between high-cost and low-cost providers. This episode features valuable resources, including Otter's book Teach and Retire Rich and the 403(b)wise website, offering practical advice on avoiding high fees and poor investment choices.  Whether or not you are a teacher, you’ll find this episode full of valuable education. And, be sure to share this with friends and family members who are teachers. Key Takeaways: • Be on the lookout for financial predators who’ll lure you into high fee accounts. • The 403(b) is a great tool for your retirement. • There’s a lack of federal fiduciary protections which allows for school teachers to be taken advantage of. • How 403(b)wise is helping educate teachers on their best financial options. • What to do if you’ve already invested your money in a high fee account. • How sales agents are incentivized to harm teachers. Key Timestamps: (02:17) Jesse’s Monologue: Teachers Are Getting Taken Advantage Of (03:51) Advice for Teachers (09:24) Introducing Dan Otter and 403(b)wise (11:51) The Problem with 403(b) Vendors (18:03) Annuities in 403(b) Plans (24:12) Wise Consumer Tips for Financial Products (25:28) Understanding Fixed Income and Annuities for Teachers (27:46) The Ethical Dilemma of Financial Advisors (31:48) Advocacy and Resources for Teachers (37:11) Navigating 403b and 457(b) Plans (42:47) Conclusion and Final Thoughts Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, teachers, teacher finances, 403(b), 403b, 457(b), 403(b)wise Mentions: Website: https://403bwise.org/ LinkedIn: https://www.linkedin.com/in/daniel-otter-ph-d-0380a61/ Mentions: Teach and Retire Rich:  https://amzn.to/4dQloRi Ten Rules for Retirement Investing: https://www.youtube.com/watch?v=_ewjha6cu1M https://www.nytimes.com/2016/10/23/your-money/403-b-retirement-plans-fees-teachers.html https://www.nytimes.com/2018/03/16/your-money/403b-annuities.html 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.

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    What No One Tells You About Early Retirement | Steve Adcock - E91

    Today, Jesse helps us step out of our financial frame and see the broader context of our lives. Quoting from David Foster Wallace’s “This is Water” speech, he highlights our self-centered bias and makes suggestions on how we can gain greater perspective through the support of those around us. In his monologue, Jesse also notes Charlie Munger’s belief that the world isn’t driven by greed, but rather by envy, and that often our reality seems a certain way because of what we see around us. Steve Adcock joins the conversation to share his own perspectives on financial independence, early retirement, and, perhaps most importantly, finding meaning in both. Previously featured on episode 16 of The Best Interest, Steve provides us with a bit of an update on his FIRE journey since retiring at just 35 years old. He gives us a taste of the quippy insights he shares weekly through Millionaire Habits and delves into some of the mental health considerations that should come along with our financial goals, sharing how he and his wife have been able to inject their financially independent lives with purpose and meaning. If you’re looking for some practical advice around the basics, mental health, and the power of passive investing, this is the episode for you. Key Takeaways: • What is your “frame” and how can people on the outside help us see our realities for what they are? • Mentors, friends, or others in your network could help you step out of your frame and see your financial situation in a new light. • How to change your lifestyle with your financial situation to maximize every moment. • The smart shopping habits to adopt that’ll set you miles ahead of most people. • Why the basics aren’t overrated and are worth revisiting regularly. • Why you need to plan for not just getting to retirement, but also what comes after. Key Timestamps: (01:38) Understanding Your Frame of Reference (03:29) David Foster Wallace's Insight on Self-Centeredness (05:04) The Role of Envy in Personal Finance (12:51) Interview with Steve Adcock: Achieving Financial Independence (20:38) Lifestyle Changes and Financial Strategies (25:50) The Power of Passive Investing (29:50) Adjusting Spending in Retirement (31:38) Evaluating Subscriptions and Spending (37:45) The Importance of Financial Basics (40:59) Finding Purpose in Retirement (50:46) Millionaire Habits and Final Thoughts Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, retire early, financial independence, digital nomad, millionaire habits, financial basics More from Steve: Millionaire Habits: https://millionairehabits.us/ Website: https://steveadcock.us/ LinkedIn: https://www.linkedin.com/in/steveallenadcock/ Twitter: https://x.com/SteveOnSpeed Mentions: Millionaire Habits: How to Achieve Financial Independence, Retire Early, and Make a Difference by Focusing on Yourself First by Steve Adcock The Best Interest Podcast, Episode 16, “Retire at 35 with Steve Adcock” https://open.spotify.com/episode/6lhHT4r7aNfrjwVVqKL3ha?si=c00ca0f26e934a2a Mimetic Desire and Consumer “Choice” by Katie Gatti Tassin https://bestinterest.blog/frame/ 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.

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    No Diversification = Deep Trouble?! | AMA #3 with Jesse - E90

    Back with another AMA, Jesse tackles your questions on employee stock incentives, diversification, how taxes affect investments, and more! Our first question comes from Lynn, who asks about when to take Social Security, which opens up a broader discussion on optimal timing for retirement benefits. While she and her husband initially planned to wait until age 70 to maximize benefits, based on family longevity, Lynn’s making some reconsiderations. Key considerations for anyone approaching Social Security include health, family history, need for benefits, ongoing work plans, spousal benefits, and how Social Security fits into their broader financial plan.  Yogi is considering his company's Employee Stock Purchase Plan (ESPP), which offers a 5% discount but no look-back provision. While it may seem like "free money," he's concerned about missing other investment opportunities. Key factors include market risk, taxes, and the risk of holding too much company stock.  Jacob and his wife, both 32, have diversified investments across various accounts, including sector-specific funds and broader options like S&P 500 and international funds. Jesse dives into ideas on how to diversify investments into a variety of asset classes, sectors, and geographies. Maple Leaf is turning 65 and plans to apply for Medicare, asking whether the income lookback period for IRMAA (Income-Related Monthly Adjustment Amount) is a one-time event or reviewed annually. The lookback period is annual, with a two-year delay, meaning income from two years prior determines the surcharge. Jimbo from Alabama asks whether the fiduciary standard is a sufficient filter when choosing financial advisors. While being a fiduciary is important, as it requires advisors to act in their clients' best interests, it’s a "coarse filter," and clients should dig deeper by asking about advisors' payment structures, investment philosophies, and potential conflicts of interest.  Our last question comes from Eric. Eric, 38, plans to retire at 55 while his wife intends to work until 65, raising the challenge of coordinating their financial and lifestyle transitions. Jesse emphasizes the importance of clear communication about how their daily routines and relationship dynamics might change as one partner retires while the other continues working If you’d like a question in a future AMA, send Jesse a message! Key Takeaways: • When you want to take out Social Security depends greatly on your health (current and anticipated), personal needs, work plans, spousal benefits, and more. • How do ESPPs work? And how can you make the most of these employee offers? • How to diversify your investments into a variety of asset classes, sectors, and geographies. • What is IRMAA? And how can you make the most of it? • Just like when you look for a doctor, a therapist, or any other professional help, you’ll want to ask a series of questions to find out how they work and if it’s a good fit. • How to balance your retirement plans with your spouse’s. Key Timestamps: (00:00) - Introduction and Featured Review (01:47) - Family History and Social Security (12:54) - ESPPs and Taxes (21:21) - Investment Diversification (29:06) - IRMAA and Lookback Periods (37:41) - Questions to Ask Potential Advisors (45:57) - Lifestyle Transitions to Retirement Key Topics Discussed: The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, IRMAA, ESPP, Income-Related Monthly Adjustment Amount, Employee Stock Purchase Plan, ask me anything, early retirement, capital gains tax   More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog When Should I Take Social Security?:  https://bestinterest.blog/when-should-i-take-social-security/ 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.

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Why is personal finance so complicated? Even worse, the Internet is full of personal finance “experts” providing short-sighted, error-prone, and outright bad financial advice. Jesse Cramer has a knack for using everyday experiences to make personal finance accessible for the average investor. His extensive research coupled with skilled narrative makes personal finance actually enjoyable. By day, Jesse works for a fiduciary wealth management firm in Rochester, NY. By night, he runs The Best Interest - nominated in 2022 for "Personal Finance Blog of the Year.” The Best Interest simplifies personal finance and investing to make your life easier, smarter…and a little richer, too. Come invest in knowledge with The Best Interest.

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