$60M Exit, 25+ Deals, and Why Angel Investing Isn’t For Most | Auren Hoffman

Moneywise

Hampton

Business, Entrepreneurship, Investing

4.8 • 674 Ratings

🗓️ 3 June 2025

⏱️ 37 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Auren Hoffman reveals the unglamorous truth about angel investing—why he still does it, what he’s learned, and why it’s not for everyone.

Here’s what we talk about:

Auren Hoffman made $60M—and then became an angel investor.
He shares why angel investing isn’t as sexy as it sounds.
The truth about money: yes, it did make him happier.
How he tracks spending (only big and small stuff—never the middle).
Why he never sets goals and doesn’t chase happiness.
His step-by-step guide to being unhappy (for real).
How trash-talking saved LiveRamp from a PR meltdown.
The right way to invest after a big exit (hint: take it slow).
Why most people shouldn’t even think about investing before hitting $3M.
Sam and Auren go deep on process vs. planning—and what really drives success.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
Auren’s Twitter https://x.com/auren

Chapters:
(00:00) Auren Hoffman's Big Exit
(00:17) The Reality of Angel Investing
(00:53) Introducing Moneywise
(01:02) The Hampton Community
(02:23) Auren's Early Entrepreneurial Journey
(03:39) First Million in the Twenties
(06:47) LiveRamp and the $60 Million Exit
(07:52) Handling Wealth and Lifestyle Changes
(12:00) Navigating Business Challenges
(13:56) Entrepreneurial Mindset and Resilience
(15:33) The Importance of Community for Founders
(17:17) Navigating Uncertainty in Business
(17:40) Insights from Successful Founders
(18:26) Auren's Journey Post-Big Exit
(19:44) Balancing Work and Personal Fulfillment
(21:05) The Philosophy of Happiness and Success
(28:52) Advice on Angel Investing

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Sam Parr

Founder of Hampton, a private community for CEOs.
Sold his last company, The Hustle, for tens of millions.

Transcript

Click on a timestamp to play from that location

0:00.0	I think I ended up with like $60 million after the exit.
0:05.3	Arn Huffman's big exit was, well, really big.
0:09.1	That wasn't the goal, though. In fact...
0:11.3	I don't set goals. I never, I've never have.
0:14.2	And that first $60 million, it was just the beginning.
0:17.4	You see, these days, Arn exits companies all the time, but they're not his
0:22.1	own companies. He does so as an angel investor. But those exits are, frankly, a bit boring.
0:28.2	I don't get that much satisfaction investing, period. Angel investing, it sounds awesome. Big exits,
0:36.1	big checks, but it's not for everyone. Personally, I'm not the biggest
0:40.2	fan, but it works for Arn. In this episode, we're going to talk about why he loves to Angel
0:45.3	invest and if it could work to you. And also, he's going to share his easy step-by-step guide on how
0:51.4	not to be happy. I'm Sam Parr, and this is MoneyWise.
0:55.5	And this is a show where we don't talk about how to get rich.
0:58.3	We talk about what happens next once you already have money.
1:01.9	A lot of the conversations that I have for this podcast, they're inspired by a community that I
1:06.5	own.
1:06.8	It's called Hampton.
1:07.7	Joinhampton.com.
1:09.1	We have a thousand plus members. And the average company
1:12.1	does something like $25 million a year in revenue, which means the average member is incredibly
1:16.9	wealthy. And so I'm able to see all types of incredible conversations. And a conversation that I see
1:22.0	happening a lot lately is from people who have recently sold their company and are asking if they
	...

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