How Do Ultra-Wealthy People "Buy, Borrow, and Die?" (AMA, E99)

How Do Ultra-Wealthy People "Buy, Borrow, and Die?" (AMA, E99)

Author: Jesse Cramer January 29, 2025 Duration: 43:38

Time for another AMA with Jesse! First, Randy asks what it means to be rich, leading to an interesting evaluation of personal values, goals, and circumstances. Jesse explores relativity, "keeping up with the Joneses", and what it means to have "enough". Then, Bob asks about the potential tax burdens on beneficiaries and heirs, and Tom wonders whether some tax savings are worth the effort of logistical complexity. The fourth question comes from regular listener, Yogi, asking about the role of bonds in diversifying a portfolio. Jesse gets into the details of which bonds are which, which financial goals they're good for, and when you should consider other options. To wrap up the show, Hector asks about the "buy, borrow, die" strategy employed by the ultra-wealthy: buy appreciating assets, borrow against them for liquidity without selling, and pass them to heirs with a stepped-up cost basis, avoiding capital gains taxes. 

If you'd like a question in a future AMA, send Jesse a message!

Tune in next week for the 100th episode celebration!

 

Key Takeaways:
• Wealth varies based on individual values and circumstances. It's less about achieving a specific number and more about feeling secure and content with your resources.
• The tax burden of inherited IRAs is based on the beneficiary's income and tax bracket, which can differ significantly from the original contributor's tax savings.
• Decisions like Roth conversions depend on whether the potential tax savings justify the added effort and complexity for an individual.
• Bonds provide stability and dependability for short-term goals. Short-duration, high-quality bonds like U.S. Treasuries are less sensitive to interest rate changes and offer more reliability.
• While effective for minimizing taxes, the "buy, borrow, die" strategy involves risks such as margin calls, regulatory changes, and the cumulative cost of loan interest potentially outweighing benefits.
• Wealth strategies should focus on understanding and minimizing tax liabilities without excessive risk, avoiding overly aggressive tax avoidance tactics.

 

Key Timestamps:
(02:17) Question 1: What Does It Mean to Be Rich?
(09:11) Question 2: Concerns About 529 College Savings Plans
(16:57) Question 3: Roth Conversions and Tax Savings
(23:50) Question 4: Evaluating Bond Performance and Diversification
(31:23) Question 5: The Buy, Borrow, Die Strategy

 

Key Topics Discussed:
The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, buy borrow die, Roth conversions, tax avoidance, inheritance, bonds, diversification, rich, five year rules

 

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.


Navigating the world of money can feel overwhelming, with a constant stream of conflicting tips and trendy, quick-fix schemes. Personal Finance for Long-Term Investors-The Best Interest cuts through that noise. Host Jesse Cramer brings a unique perspective to the conversation, transitioning from his background as an aerospace engineer to his work as a fiduciary financial advisor. This podcast is built on the principle that genuine wealth isn't built overnight through speculation, but through consistent, well-reasoned decisions made over decades. Each episode delves into the mechanics and mindset required for that journey, exploring topics like retirement planning, intelligent investing, and the behavioral aspects of managing money. You'll find discussions that go beyond surface-level advice, examining the "why" behind proven strategies and how to apply them to your own life. The tone is conversational and grounded, avoiding financial jargon in favor of clear explanations. It’s a resource for anyone tired of the hype and seeking a sustainable path forward. By focusing on evidence-based ideas and patient execution, this podcast aims to provide listeners with the tools and confidence to build a secure financial future on their own terms. Tune in for a thoughtful, long-term approach to personal finance that prioritizes your best interest.
Author: Language: English Episodes: 100

Personal Finance for Long-Term Investors
Podcast Episodes
11 "Bad" Financial Moves...That Are Actually Fine (E128) [not-audio_url] [/not-audio_url]

Duration: 41:28
In this candid solo episode, Jesse walks through a series of financial decisions that look "wrong" on paper but make complete sense when viewed through the lens of real life, values, and tradeoffs. Using personal example…
"The Most Important Number" in Your Retirement?! (E127) [not-audio_url] [/not-audio_url]

Duration: 53:37
Jesse is joined by Jeremy Keil—Certified Financial Planner, Chartered Financial Analyst, author of Retire Today, and host of the Retirement Revealed podcast—for a wide-ranging conversation that reframes how people should…
Will You Retire in 2026?? (AMA, E126) [not-audio_url] [/not-audio_url]

Duration: 50:46
On Jesse's 12th "Ask Me Anything" episode, he opens the year by tackling the questions that tend to surface when calendars turn and retirement feels closer than ever. He begins with a thoughtful exploration of whether "t…
My Ghosts of Financial Past, Present, and Future (E125) [not-audio_url] [/not-audio_url]

Duration: 51:11
In this Christmas episode, Jesse steps back from year-end checklists and market noise to tell a more personal story—one shaped by the "ghosts" of his financial past, present, and future. He begins with the early experien…
The Scenario When HSA's Are a *BAD* Account (AMA, E124) [not-audio_url] [/not-audio_url]

Duration: 50:11
On Jesse's 11th "Ask Me Anything" episode, he unpacks four questions that sit at the center of real-life financial decision-making. He starts with a grounded look at the 15-year vs. 30-year mortgage debate, cutting throu…
Should "Coast FI" Be the *Real* Goal? (E123) [not-audio_url] [/not-audio_url]

Duration: 38:53
Jesse sits down with Andy Hill—personal finance educator, podcast host, and creator of Marriage, Kids, and Money—for a candid conversation about building wealth while building a life you actually enjoy. Andy shares how a…
Why Retirees Struggle with Health Over the Holidays (E122) [not-audio_url] [/not-audio_url]

Duration: 47:44
Today, Jesse is joined by Dr. Phil Pearlman—psychologist, behavioral finance veteran, and founder of the Pearl Institute—for a conversation about how long-term health and long-term wealth are two sides of the same coin.…
A New Predator Coming For Our Retirement Dollars (E120) [not-audio_url] [/not-audio_url]

Duration: 34:18
Today, Jesse is joined by Professor John Dinsmore—behavioral finance researcher, marketing scholar, and author of The Marketing of Debt: How They Get You—for a conversation about how persuasion, psychology, and modern ad…