I sold my company for over $40 million when I was 31. Here’s every idea I tried before my big win: 1. In high school I made $2,500 one summer flipping 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. Made up to $1,000 a day. Learned how to sell - and how to blow all my money on beer. 3. That same year, I started an online liquor store selling rare whiskey. It lasted three months before a lawyer told me I wasn't doing things correctly. Still made $10K in profit. 4. In San Francisco, I started a weekly business book club called The Anti-MBA. Couldn't figure out how to monetize it, but met lifelong friends. 5. Tried selling an accountability program to The Anti-MBA. $20/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 three founders. 150 people showed up. Made $1,090. 7. Then came Bunk - parties for people finding roommates. We funded it with $15k, it didn't succeed and got acqui-hired 9 months later. 8. We turned Bunk into a Tinder-style roommate app. Tens of thousands of users, zero revenue. Should’ve just made it a dating app - that’s what people used it for anyway. 9. Next, The Miracle Craigslist Template. A simple email script for finding apartments on Craiglist. Made $500–$1,000 a month for two years. 10. Itch Juice - a poison ivy treatment. I bulk-bought generic ointment and rebranded it as I knew I could buy Google ads for cheap. Shut it down after two months. Dumb idea, smart lesson: schemes are dumb. 11. Hosted a weekend copywriting class with @nevmed. We each made $10k. 12. Then came Hustle Con - a conference for startup founders. Made $40k in profit. Ran it three more times, revenue doubled each time. 13. I saved $300k and pivoted Hustle Con into a media company called The Hustle. Spent six months writing hundreds of articles. Traction was good, but consistently getting traffic was hard. 14. The big one: we pivoted again - from a blog to a newsletter. Biz model was so much better. It didn’t feel huge at first, but it was a rocket ship. $12m in revenue by year four, sold the company when I was 31. Changed my life. 15. Inside The Hustle we launched Trends - a $300-a-year community for entrepreneurs. Great revenue, tough margins. Lesson: low price, high volume = hard business. 16. The Hustle expanded our events. $1.5M in revenue, almost no profit. Then Covid killed it overnight. 17. The Hustle published My First Million - a podcast that now has 700+ episodes and millions of downloads. 18. Bought a ranch in Texas to turn into an Airbnb. Broke even. Bought other real estate...lost money on all them! And now…Hampton. Easily the most impactful. We create peer groups and chapters for founders doing at least $3m in revenue. We have a team of 20, mostly in NYC where I live, and change our member's lives. Lessons from all this: 1. Stay focused. Many times I had something good but didn't stay focused! 2. Everything's hard, even when its working! 3. Have smart friends, peers around you who you can rely on to hold you accountable, keep you humble, and hear you out.