Does Making $100M Make You Happy?

Moneywise

Hampton

Business, Investing, Entrepreneurship

4.7 • 701 Ratings

🗓️ 28 April 2026

⏱️ 40 minutes

🔗️ Recording | iTunes | RSS

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Summary

Chapter Timestamps

00:00 — Homeless at 26, $100M exit at 32 02:22 — Building Mutesix: one of the first productized Facebook ad agencies 09:39 — The 2019 sale and what Steve actually took home 11:52 — The wire hits — at the Western Wall in Israel 14:46 — "The money didn't change my life": post-exit identity crisis 16:31 — How Steve actually spends: the chef, the donations, the Birkin he never bought 19:55 — Why he's obsessed with insurance (and what he tells founders) 23:18 — Post-exit on a Tuesday: the daily search for meaning 25:07 — Did the $100M exit actually make him happy? 32:03 — Looking back 15 years — and what the next 5 look like

At 26, Steve Weiss was homeless in Los Angeles, sleeping in his car in a 24 Hour Fitness parking lot with $200 to his name. Six years later, his Facebook ads agency Mutesix sold for $100 million to Dentsu. The day the money hit his account, he was standing at the Western Wall in Israel — and got a phone call that made him realize money doesn't fix what's broken inside you.

In this episode of MoneyWise, host Daniel Berk sits down with Steve Weiss to walk through the parts of a nine-figure exit nobody puts in the press release: how much he personally took home, if the wire made him happy, and what post-exit life actually looks like on a random Tuesday when you've already "won."

In this conversation:

How Steve built Mutesix from 4 clients in 2013 into one of the first productized Facebook ad agencies — and sold it to Dentsu in 2019 for $100M
The emotional moment the wire hit at the Western Wall, and the tragedy that hit the same day
His real spending today: a private chef 3–4 days a week, why his wife asks for nonprofit donations instead of Birkin bags, and the cause they're funding
Why he over-indexes on life and health insurance — and the advice he gives every founder
The post-exit purpose vacuum — what he calls "almost impossible to replicate" — and how he's filling it now with family, angel investing through SGD, his podcast, real estate, and possibly politics
What he'd do differently if he could rewind 15 years
The honest answer to the question every founder secretly asks: did $100 million actually make him happy?

If you've ever wondered whether the exit really fixes anything, this is the episode.

MoneyWise is the personal finance podcast for high-net-worth founders. Hosted by Daniel Berk and produced by Hampton — a private, vetted community for founders and CEOs running businesses doing $2M+ in revenue. Apply at joinhampton.com.

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Transcript

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0:00.0	At 26 years old, Steve Weiss was homeless in LA, sleeping in his car in a 24-hour fitness parking lot.
0:06.4	He had $200 to his name.
0:08.9	Six years later, he sold his company for over $100 million.
0:12.3	The day the money hit his account, he was standing at the holiest place on Earth and got an unexpected and tragic phone call.
0:18.7	He says the exit gave him one less thing to worry about, but I asked if it made him happy. There's a ton of podcasts out there and resources that teach you how to be wealthy and how to make money. But there aren't that many resources that try to teach you how to handle the life changes that wealth brings. This podcast is brought to you by Hampton, a private, highly vetted community for CEOs, business owners, those types of people. Most of the people do, on average, around $25 million a year in revenue. And so I'm able to see tons of conversations about wealth, how to handle all the changes that come with it, how to spend, how to have all these types of conversations that typically just aren't happening in public. And by the way, if you're a CEO of a company, or you own a business that does at least $2 million in revenue, check out this community at joinhampton.com. In this podcast, Money Wise, we talk about real numbers and real people who are doing things that typically are only spoken about behind closed doors. The people who come on, they're going to be radically transparent about their numbers. Sometimes they're anonymous. Sometimes they're not. In today's episode, we're going to talk about whether or not a $100 million exit makes you happy. And today's episode of Money Wise is Steve Weiss. Welcome back to another episode of Money Wise. Thanks for joining us today. Steve Weiss, we have as a guest in the show. Thanks again,
1:27.8	Steve, for joining us. Sounds like you just got done with a workout today. How you feeling?
1:42.7	Feel great. Drop my kids off at school when you did a quick workout. Now I get to hang out with you, Dan. Let's do it. And it was chest day, which is always night. I know there's a, there's a whole a whole group of people that avoid leg day like it's a like it's the plague but
1:44.4	I'm actually one of those people that goes
1:46.4	to the gym for leg day like it's a like it's the plague but yeah i'm actually
1:45.2	one of those people that goes to the gym for leg day because i'm a long distance runner so you have to i'm the opposite of most people you got it you got to force me into a chest day but i know i'm i'm the weird one in that sense i love the let i did leg day uh two days ago we did a little backwards dumbbell lunge, which is pretty cool.
2:01.2	We did some deadlifts.
2:02.4	Nice.
2:02.8	I love, I'm with you, man, but as you, as you, like the two days ago. We do a little backwards dumbbell lunge, which is pretty cool. We did some
2:01.5	dead lifts. Nice. I love, I'm with you, man, but as you get older, in my opinion, it gets more and more important to do weight training. I think that weight training is the way you retain balance, the way you, you know, make sure you're working optimal recovery. I mean, I just feel like it's the greatest thing you could do.
2:17.8	100%.
2:18.7	Well, I appreciate you joining the show today.
2:20.5	I'd love to open up just with your exit.
2:23.4	Mute 6 is a company.
2:24.7	I'd love for you to tell us more about what Mute 6 was and kind of walk us through the build
2:29.3	of the company and then ultimately the exit back in 2019.
2:32.8	So one thing to know about me is I'm a veteran of natural disasters.
2:38.2	I know that sounds like, what do you mean by that, Steve?
	...

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