How I Made $40M

I sold my company at 31 years old and ended up making over $40 million.

Here's every idea I tried before my big win.

1.

In high school, I made $2,500 one summer by flipping the graduating seniors' used sports gear on eBay.

2.

At 20, I launched a hot dog stand called Southern Sam's Wieners as Big as a Baby's Arm. I made up to $1,000 a day. I learned how to sell, and I also learned how to blow all my money on beer and realized that doing outdoor labor is not for me.

3.

That same year, I started an online liquor store selling specialty whiskey. It lasted 3 months before a lawyer told me I wasn't doing things correctly. Still, I made $10,000 in profit. 4.

In San Francisco, I started a weekly business book club called The Anti-MBA.

I couldn't figure out how to monetize it, but I met lifelong friends.

5.

I tried selling an accountability program to The Anti-MBA book club. It was $20 a month and you were paired with another member to encourage you to read a book.

No one wanted it. 6.

In 2014, I hosted Bootstrap Live, a mini event interviewing 3 founders. 150 people showed up and I made about $1,200. 7. Then came Bunk, a business where we hosted parties for people finding roommates. We funded it with $15,000 of our own money and it did not succeed, but we did get acquihired 9 months later. 8. We turned Bunk into a Tinder-style roommate app.

Tens of thousands of people downloaded the app, but we made $0.

We should have just made it a dating app because that's really how people were using it anyway.

9. The Miracle Craigslist Template.

I made a simple email script for helping people find roommates on Craigslist. It made around $500 to $1,000 a month for about 2 years. 10.

Itch Juice, a poison ivy treatment. I made a bulk order of a bunch of generic poison ivy ointment and I rebranded it because I knew I could buy Google Ads for cheap.

I shut it down after 2 months because it was just a dumb idea and I learned that little schemes like this are just a waste of time. 11. Hosted a weekend copywriting class with my buddy Neville. We each made $10,000. 12. Then came HustleCon, a conference for startup founders.

Made around $40,000 in profit. Ran it 3 more times and revenue doubled each time.

13, I had saved up $300,000 when I pivoted HustleCon into a media company called The Hustle. I spent 6 months writing hundreds of articles. Traction was pretty good, but consistently getting people to come to a website was very, very hard. 14, the big one, we pivoted again from a blog to a newsletter. The business model was so much better. It didn't feel huge at first, but it was a rocket ship.

We did $12 million in revenue by year 4, and I sold the company when I was 31.

It changed my life.

15, The Hustle published My First Million, a podcast I'm the co-host of.

We now have over 700 episodes, are one of the most popular podcasts in the world with hundreds of millions of downloads, and now Hampton Easily the most impactful and most fun.

We create peer groups and chapters for founders who are doing at least $3 million a year in revenue. It's what I would have wanted all these years building my companies. We have a team of 20, mostly in New York City where I live, and we change our members' lives. If you run a business that does at least $3 million in revenue and you're lonely, you want to be around other people like you, check us out. Joinhampton.com.

Now, the lessons I learned from all this.

Number 1, stay focused. There's been so many times when I quit on something when it potentially could have been great, but I didn't stay focused.

Number 2, everything's hard even when it's working. And number 3, find smart people who can hold you accountable, keep you humble, and hear you out. This is a long journey and you can't do it alone.