We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wr

Why do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.

He manages $1.5 billion for other people — and still tracks his own spending in a paper checkbook.

Glenn Ullmann is a former Air Force pilot who left the military at 29 with a couple hundred thousand dollars, cold-called 200 strangers a day out of a Ponte Vedra phone book, and built Ullmann Wealth Partners into a $1.5 billion RIA that has never had a down year — including 2008. He stopped worrying about money somewhere north of $20 million. Now 63, he spends $30–40K a month, flies his own $1.25M Cirrus, gives more to charity than he can deduct, and still shows up to the office every day.

This episode gets into the tension between saving and actually living: why Glenn tells clients with health issues to fly private before their kids do it with the inheritance, how a $10M portfolio pays you $300K a year in "rent" whether markets are up or down, and why he thinks stocks are a bad word. We also cover how he gave up 80% of his own firm to keep his partners, the paper ledger that runs his life, the client who started at $100 a month and now takes the best trips on earth, and why he'd tell a 20-year-old to study English or history instead of finance.

Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mw

Timestamps:
01:46 — Who Glenn is, what Ullmann Wealth Partners does, and why "returns don't matter if you rear-end Melinda Gates without an umbrella policy"
04:16 — Growing up in his grandfather's plastics business, the Robin's-egg Cadillac, and the gold coin that says "your friendship means more to me than a pot of gold"
06:26 — A Morgan Stanley account at 14, paper route money, and his first stock: Sears Roebuck
07:44 — Nobody from his high school went to the military. He went to the Air Force Academy three days after graduation: "the best thing I ever did, other than marrying my spouse"
11:50 — The Cirrus G7, the parachute that lowers the whole plane, and the button his wife can push if Glenn stops functioning mid-flight
13:35 — From AWACS pilot to pharma rep to stockbroker: dialing 200 people a day, 10 conversations, one client
17:45 — Net worth leaving the Air Force at 29 and the million-dollar goal on a piece of paper that "never happened"
19:26 — The $2M–$20M client sweet spot, and why the firm has never contracted in 25 years — even 2007–2009
21:57 — Why he went from owning 100% of the firm to 20%: "How could they not have equity?"
24:03 — The 11x17 "life map," and the client who was stabbed and left for dead in her New York apartment
26:15 — HENRYs who save $10K a month and still need to be told to go enjoy the rest: "People get cancer. People die falling off a ledge."
28:49 — "If you don't spend this money and fly first class, your kids will when you're dead"
30:40 — The net worth where Glenn stopped worrying: "probably above 20"
31:49 — Alimony, fun, and the pen-and-paper checkbook ledger a $1.5B wealth manager uses to track his Amex
33:29 — The $1.25M four-seat plane, $40–50K a year to operate, and a $30–40K monthly burn before philanthropy
35:10 — Giving appreciated stock and exceeding his deduction limit every year
36:21 — Why he still goes to work at 63, the wingman system, three chronic illnesses, and "sometimes a founder needs to get out of the way"
39:40 — The Melissa example: $100 a month in 1993 to the best trips on earth
41:26 — Where to park $10M after a liquidity event: "you're going to collect around $300,000 a year in dividends and interest"
42:55 — Not a real estate guy, the $100K driveway, and "I never invest in things that eat while I'm asleep"
44:48 — 90% in global equity, and why "they're not stocks, they're companies"
45:40 — Reframing an $80K private flight as a month and a half of portfolio income
47:39 — What he'd tell a 20-year-old picking a major: English or history

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Fly First Class Now, or Your Kids Will: Glenn Ullmann's Money Rules

Moneywise

Fly First Class Now, or Your Kids Will: Glenn Ullmann's Money Rules