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.

What’s the difference between a $10m, $100m, and $1b lifestyle? Asked this question in Hampton's Slack community since we have people worth $10m - $2b. A few takeaways from the 50+ replies: $50k – $100k liquid • The first “I feel rich” for many in 20s. • Bills stop hurting. You breathe. • $1M net worth rarely changes anything. In high-cost cities, it’s just “comfortable professional.” Still very income-dependent. $10M liquid - This is the first real unlock. • Safety net feels permanent • You stop looking at the right side of the menu • Business-class by default, 5 hotels when you want • You can cover friends’ flights to make trips happen • Life doesn’t run you anymore. $20M–$25M liquid: • “I can spend $50k/mo forever and still compound.” • Nicer primary home (or rent ultra-nice; fewer ownership headaches) • Staff for convenience (nanny, cleaners) • Family support start to be normal, not “splurge” $50M liquid • Cash flow is thick and hard to fully redeploy. • 2nd homes, extended travel • Serious privacy planning begins • You’re learning trusts, tax vehicles, and who to not trust $100M: • Life becomes frictionless. • Fly private often (some buy; many rent because ownership is work) • Full household team + exec assistants + specialists • Family office(s), capital allocation becomes a job • You choose projects; problems get solved without you Past $100M • personal lifestyle doesn’t change much—scale and privacy do. • Land for privacy buffers • Private gyms/courts/spas at home • You’ll never fly commercial unless you want to $1 billion • Money becomes institutional. • You never see a bill • Global properties, fully private travel • Governments, universities, and CEOs court you • It’s legacy season: foundations, endowments, monuments A few real anecdotes from the thread: • A billionaire bought a pro sports team mid-flight on his jet. His right-hand guy became COO. • A friend group dropped $200k–$300k on a yacht week just to get everyone together. • Multiple members set up dual family offices (JPM + independent) to manage life + investments. The biggest trap everyone warned about: • “Coming into money without accomplishing anything is a curse.” • Lottery-winner energy breaks people. Purpose > purchases. Cash flow > net worth (psychologically). • Even people with $50M–$100M feel “poor” during low-cashflow years. Meaning, even if you have a high net worth -- if your business income goes away even if you don't need it, it feels horrible. Mentally brutal. What actually brings joy at scale: • Buying back time (coaches, chefs, pilots, concierge) • Funding memories (fly the whole crew, pick up every tab) • Being present (one member took a year as a stay-at-home dad - “wouldn’t trade it for anything”) What gets old fast: • More “stuff” to manage • Identity tied to net worth • Chasing bigger dopamine (toys) instead of deeper meaning (health, family, service, community) -- Ok, that's it - that's my ChatGPT summary of all the replies!