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.

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.

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.

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.

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.

Jesse explores the intricacies of student loan forgiveness, highlighting the fallacy that loans can simply vanish without consequence. He argues that the financial burden ultimately falls on taxpayers and critiques the notion that the U.S. government can "magically" eliminate student debt. Jesse explains the Public Service Loan Forgiveness (PSLF) program and how student debt exacerbates mental health problems. He proposes a balanced approach of partial interest forgiveness to alleviate borrower burdens, shorten repayment periods, and benefit both individuals and the government, all while maintaining personal accountability.

Today’s guest, Katie Gatti Tassin, is the founder of Money with Katie, a platform she created in 2020, which was later acquired by Morning Brew. During the interview, Jesse and Katie discuss frustrations with the American healthcare system, underscoring how flawed incentives impede rational decision-making. Most of the conversation revolves around financial literacy and misconceptions among the FIRE community and broader society. As Jesse and Katie reach the end of the discussion, they share their thoughts on how social media and social isolation affect us financially and mentally.

This is a wide-ranging conversation with a few insightful tangents. If you’re looking for a personal, real, and thoughtful finance podcast, then this is the episode for you.

Key Takeaways:
• Loan forgiveness doesn’t make the loan disappear… Someone is eating that cost.
• Jesse explains how the Public Service Loan Forgiveness (PSLF) program works.
• The broken incentives of the American healthcare industry discourages rational decisions.
• How “tough love” online finance personalities like Dave Ramsey or Caleb Hammer work (or don’t).
• How our individualism and social media lead to social isolation and affect our mental health.
• If you’re listening to this podcast, you’re probably more financially secure than you think.

Key Timestamps:
(01:38) Jesse’s Monologue: Student Loan Forgiveness & Moral Hazards
(20:37) A Proposed Solution to Student Loan Debt
(27:06) Introducing Katie Gatti Tassin
(28:46) The Healthcare Marketplace Dilemma
(38:23) Hospital Fines and Perverse Incentives
(40:13) Balancing Savings and Enjoying Life
(47:42) Tough Love in Personal Finance
(51:26) Building Community and Financial Implications
(58:18) Social Media's Impact on Mental Health
(01:11:01) Conclusion and Resources

Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Money with Katie, Morning Brew, Katie Gatti Tassin, American health care, student loan forgiveness, student debt, Public Service Loan Forgiveness, PSLF

Mentions:
Website: https://moneywithkatie.com/
LinkedIn: https://www.linkedin.com/in/katiegatti/

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.

Referring back to his article, Fundamentals Of Retirement: Is the Summit “Good Enough?”, Jesse uses an experience hiking in the Adirondack Mountains as a metaphor to explore retirement preparedness. He recounts how being poorly equipped for a challenging hike can mirror the pitfalls of entering retirement without thorough planning - you might reach the summit, but the journey and destination may not be as enjoyable. Sharing the example of a couple, John and Eva, who are on the brink of retirement with substantial assets and a solid financial plan, Jesse raises critical questions about their investment strategy, withdrawal plans, and tax considerations, suggesting that while they are well-positioned, their retirement journey could be smoother with additional preparation.

For today’s interview, Jesse is joined by Rob Berger. Rob is a contributing editor for Forbes Advisor, host of the Financial Freedom Show, and author of “Retire Before Mom and Dad: The Simple Numbers Behind A Lifetime of Financial Freedom”. He founded Doughroller.net in 2007, a popular personal finance blog that attracted millions of visitors. With a background as a litigation attorney, Rob is now a prominent voice in retirement planning, providing valuable education through his YouTube channel and other platforms.

If you’re looking for quality retirement finance tips, no matter where you are on your journey, this is a great episode for you!

Key Takeaways:

• Preparing for retirement allows you to enjoy the journey and the destination (just like hiking!).

• Learn about key aspects of retirement planning, such as investment strategy, withdrawal plans, and tax considerations, and the need for comprehensive preparation.

• What is the “Retirement Income Death Spiral”? And how can we avoid it?

• How does inflation and stock market conditions really affect your retirement savings?

• How to take a conservative approach to Social Security and still have cautious optimism about the future.

• Why you should not focus on individual stocks when planning for retirement!

Key Timestamps:

(02:10) Jesse’s Monologue: Retirement Planning Fundamentals

(05:47) John and Eva's Retirement Scenario

(13:09) Interview with Rob Berger

(14:00) Understanding the Retirement Income Death Spiral

(15:55) Inflation and Retirement Planning

(23:40) Social Security Concerns and Assumptions

(25:48) The Future of Social Security and Political Solutions

(27:24) The Importance of Diversified Income in Retirement

(29:26) The Role of Cash and Bonds in Retirement Portfolios

(34:21) The Emotional Side of Market Volatility

(39:26) Common Financial Mistakes and How to Avoid Them

Key Topics Discussed:

The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Rob Berger, Retire Before Mom and Dad, Social Security, retirement account mistakes

Mentions:

Website: https://robberger.com/

YouTube: https://www.youtube.com/@rob_berger

LinkedIn: https://www.linkedin.com/in/bergerra/

Mentions:

https://bestinterest.blog/reaching-the-summit-retirement/

Retire Before Mom and Dad: The Simple Numbers Behind A Lifetime of Financial Freedom

How Much Cash Should You Hold In Retirement?

Should Cash Replace Bonds in a Portfolio?

How to Avoid the Retirement Income Death Spiral?

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.

In today’s opening monologue, Jesse explores the concept of Sequence of Returns Risk, a crucial and often misunderstood threat to retirees, by illustrating how poor returns early in a retirement can severely impact long-term stability. He emphasizes the importance of diversification. Jesse then introduces the idea of path dependence, drawing parallels to the life of author Philip K. Dick, whose posthumous fame underscores the significance of a journey’s path, not just the journey’s outcome. Jesse connects this to investing, explaining how the sequence of returns can greatly affect an investor’s experience, despite the long-term average returns. Using "Sally the Investor" as an example, Jesse highlights the emotional and psychological challenges of navigating market volatility, reinforcing the need for resilience, understanding short-term unpredictability, and the benefits of diversification in long-term investing.

Tyler, the creator of Portfolio Charts, joins Jesse for the second half of the show. His site is known for its innovative financial tools and insights. Tyler, a fellow engineer with a passion for finance, blends technical expertise with creativity to clarify complex investing concepts. In their discussion, Tyler and Jesse explore critical retirement topics, including the safe withdrawal rate and sequence of returns risk.. Tyler introduces the concept of engineering tolerances for managing financial variability and discusses strategies like variable withdrawal rates. He explains the "flowing nature of withdrawal rate math," illustrating how safe withdrawal rates change with longer retirement periods. If you’re looking for some evidence based, long term thinking in your DIY financial life, then this is the episode for you!

Key Takeaways:

• How poor returns early on can negatively affect my retirement.

• What is “sequence of returns risk”? And how can I create a financially resilient situation for myself?

• Diversification into a variety of financial vehicles is key to the long term success of your portfolio.

• Path dependence, illustrated by Philip K. Dick's posthumous fame, emphasizes that the sequence of returns can greatly affect investment outcomes.

• What are “safe withdrawal rates”? And how can traditional average return calculations be misleading?

Key Timestamps:

(01:07) Jesse’s Monologue: Understanding Sequence of Returns Risk

(07:50) Mitigating Sequence of Returns Risk

(08:35) Path Dependence: Lessons from Philip K. Dick

(13:16) Sally's Ride: A Real Example of Path Dependence

(22:57) Investment in Knowledge: Path Dependence

(25:28) Understanding Safe Withdrawal Rates and Sequence of Returns Risk

(35:05) The Importance of Consistent Portfolios

(47:29) Tyler's Personal Finance Journey and Portfolio Charts

(51:01) Conclusion and Listener Engagement

Key Topics Discussed:

The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Tyler from Portfolio Charts, path dependence, sequence of returns risk, safe withdrawal rates

Mentions:

Website: https://portfoliocharts.com/

Mentions:

https://portfoliocharts.com/charts/withdrawal-rates/#chart

https://portfoliocharts.com/2016/12/09/perpetual-withdrawal-rates-are-the-runway-to-a-long-retirement/

https://portfoliocharts.com/charts/retirement-spending/

https://portfoliocharts.com/portfolios/permanent-portfolio/

https://bestinterest.blog/path-dependence/

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.