Ask The Compound – Episode Summary
Episode Title: How Will the $84 Trillion Wealth Transfer Play Out?
Date: September 10, 2025
Hosts: Ben Carlson, Duncan Hill (with guest expert Joey Fishman)
Overview
This episode tackles the enormous topic of the so-called "$84 trillion great wealth transfer" expected as baby boomers age and pass on assets. Ben, Duncan, and guest Joey Fishman field Compound audience questions related to the generational hand-off of wealth, real estate concentration, RSU diversification, balancing saving with lifestyle, and emergency fund strategy. The tone is practical, candid, and often light-hearted, consistently providing actionable financial insights.
Key Discussion Points & Insights
1. Real Estate Concentration and Diversification
[03:30–08:13]
- Question from Spencer: At 27, he and his wife own 21 houses (worth $4.5M, $2.4M owed), plus a growing design/build company. Should they double down on real estate or diversify into the market?
- Ben’s Analysis:
- Acknowledges their impressive early success and risk tolerance.
- Warns about idiosyncratic risks in real estate and leveraging.
- Suggests this is the right life stage to take risks:
“This is a stage in your life where you can take risks… If you do experience some sort of major correction at some point, just extend your time horizon… See how far you can take it. I don't think you'll regret it if you do.” (Ben, 06:05)
- Recommends eventually diversifying as cash flow grows but, for now, advises: “Put your foot on the gas pedal, man. I say let it rip.” (Ben, 07:13)
2. RSUs, Concentration Risk, and Diversification
[09:05–15:21]
- Question from Ben: With a large portion of compensation as RSUs at a major travel company, how should he think about diversification?
- Guest Joey Fishman’s Approach:
- Opportunity assessment: Unlikely for a large public travel company to 10x; more likely a 2-3x at best.
- Don’t diversify within the same sector: “Everybody knows this. When markets roll, correlations go to one.” (Joey, 09:59)
- Financial life-cycle perspective:
- Early career: maximize tax-advantaged savings.
- Aim for “optionality”—enough capital by a certain age to have choices.
- Selling RSUs:
- Don’t sell “into a hole”—wait for recovery if the stock is temporarily down.
- Take advantage of upward spikes to liquidate.
- Sober expectations are key.
- Behavioral Note:
“People treat these [RSUs] as a bonus. Ideally… you’re living well below your means and maxing out all of your qualified accounts… RSUs are just extra.” (Joey, 13:31)
- Echoes the proverb: “You concentrate to get rich, you diversify to stay rich.” (Ben, 11:13)
3. Savings, Lifestyle Upgrades, and FIRE Decisions
[15:36–20:35]
- Question from Uni: Early 40s, saving aggressively on a work visa in Texas. On track for $2.5M in three years, considering buying their first house, which would halve savings. Is this reasonable?
- Ben’s View:
- Lauds their high savings and “fire approach”.
- Encourages enjoying some fruits of their labor:
“Life is also short. Like enjoy some of that money. Whatever you just compressed into five or six years… I don't think you'll regret it if you buy a house, upgrade your lifestyle a little bit.” (Ben, 19:16)
- Reminds housing is also an asset and compounding remains in play even with lower yearly savings: “You’re still doing better than 95% of all Americans.” (Ben, 19:54)
4. The Reality Behind the $84 Trillion Wealth Transfer
[20:42–25:23]
- Question from Rick: Is the “great wealth transfer” really as significant as the headlines suggest?
- Ben’s Breakdown:
- Dispels the myth of a “wealth tsunami”—transfers will trickle out over decades.
- Notes:
“It’s not like all this money is going to change hands all at once. Short of a disease that immediately kills 70 million baby boomers, that seems unlikely.” (Ben, 22:05)
- Top 10% owns 87% of the market; they won’t dump stocks in a fire sale.
- Asset values will grow; new generations may wait longer than expected for inheritance.
- Housing turnover will be steady, not a flood: “It’s, again, dribs and drabs as opposed to, like, this big tsunami that's going to happen all at once.” (Ben, 24:12)
- Advice: “Baby boomers don’t wait to give it all away until after you die. How about the kids and grandkids now?” (Ben, 25:11)
5. Emergency Funds & Holding Cash
[26:04–31:21]
- Question from Andy: How do you personally deal with emergency funds and keeping cash when markets are strong?
- Ben’s Perspective:
- Emergency fund size is personal: more risk-averse may keep 12 months, typical advice is 3–6 months.
- It’s also an asset allocation question, not market timing:
“If you can’t accept the volatility of 100%… you need to have some in cash as a volatility hedge or emotional hedge… if you do hold some cash strategically, it's not the end of the world.” (Ben, 27:14)
- Historical data: Going from 100% stocks to 90% stocks / 10% cash reduces annual return by about 0.5–1.0%. Acceptable if it helps you sleep at night.
- Cautions against using emergency funds as a market timing tool.
- Open to riskier approaches (e.g., keeping more “emergency” funds in the market), as long as you're OK with possible losses and have other buffers.
Notable Quotes & Memorable Moments
-
On Real Estate Risk-Taking:
“You're young still… I say put your foot on the gas pedal and see what happens.”
— Ben Carlson [06:35] -
On RSU Diversification:
“You concentrate to get rich, you diversify to stay rich.”
— Ben Carlson [11:13] -
On the So-Called Wealth Tsunami:
“This is going to have an impact, but it's going to take a long time to play out, like two to three decades.”
— Ben Carlson [25:19] -
On Balancing Life and Savings:
“Life is also short. Like enjoy some of that money.”
— Ben Carlson [19:16] -
On Why Women Write In Less:
“The studies all show women are better investors than men because they… act for the long term where men are constantly tinkering… I wonder if that's one of the reasons men are obsessed about [finance].”
— Ben Carlson [16:05]
Important Timestamps
- 03:30 – Real estate concentration vs diversification advice for young investors.
- 09:05 – RSU strategy, concentration risk, and diversification deep dive (Joey Fishman).
- 15:36 – Is it OK to cut savings to enjoy life and buy a first house?
- 20:42 – Myth-busting the “great wealth transfer” headlines.
- 26:04 – Discussing emergency funds and holding cash during bull markets.
Tone and Style
The episode balances expert, grounded financial advice with humor and relatability. Ben tends to play straight-shooting optimist ("Bold Ben"), encouraging risk-taking when justified, while Duncan keeps things personable and light. Guest Joey Fishman provides detailed technical advice on RSUs, always emphasizing practicality and the psychological aspects of financial planning.
For New Listeners
If you’re curious about generational wealth transfer, building or diversifying a real estate empire, optimizing RSU stock compensation, or balancing savings and lifestyle, this episode delivers practical wisdom on all fronts. The hosts mix analytical rigor with clarity and a sense of fun, making even complex financial questions accessible and actionable.