How I Made $40M

Key Concepts

• Entrepreneurial Journey: The progression of various business ventures undertaken by the speaker.
• Flipping: Buying items at a low price and reselling them at a higher price.
• Monetization: The process of converting something into money.
• Acquisition: The purchase of one company by another.
• App Development: Creating and launching mobile applications.
• Content Creation: Producing and distributing digital content, such as articles and podcasts.
• Newsletter Business Model: A subscription-based model for delivering content via email.
• Peer Groups: Organized groups of individuals with similar professional backgrounds or goals.
• Accountability: The obligation to accept responsibility for one's actions.

Business Ventures and Learnings

The speaker details a series of entrepreneurial endeavors undertaken before achieving significant success, culminating in selling a company at 31 for over $40 million.

Early Ventures:

1. Flipping Sports Gear (High School): Made $2,500 in one summer by reselling used sports equipment from graduating seniors on eBay. This demonstrated an early understanding of market demand and resale value.
2. Southern Sam's Wieners (Age 20): Launched a hot dog stand, generating up to $1,000 per day. This experience taught sales skills but also highlighted the challenges of outdoor labor and the temptation of mismanaging funds (spending on beer).
3. Online Liquor Store (Age 20): Attempted to sell specialty whiskey online. The venture lasted only 3 months due to legal issues, but still yielded $10,000 in profit. This highlighted the importance of legal compliance in business.
4. The AntiMBA (San Francisco): Founded a weekly business book club. While it failed to monetize, it fostered valuable friendships and networking opportunities.
5. Accountability Program (AntiMBA): Tried to sell a $20/month accountability program to book club members, pairing them to encourage reading. This initiative was unsuccessful, indicating a lack of market demand for the specific offering.
6. Bootstrap Live (2014): Hosted a mini-event featuring interviews with three founders. It attracted 150 attendees and generated approximately $1,200. This was an early foray into event organization.
7. Bunk (Initial Phase): A business focused on hosting parties for people seeking roommates. Funded with $15,000 of personal capital, it did not succeed but led to an acquisition after 9 months.
8. Bunk (App Version): Evolved into a Tinder-style roommate app. It garnered tens of thousands of downloads but generated $0 revenue. The speaker realized it was being used more like a dating app, suggesting a misaligned product-market fit.
9. Miracle Craigslist Template: Created a simple email script to assist people in finding roommates on Craigslist. This generated $500 to $1,000 per month for about two years, showcasing the potential of niche digital tools.
10. Juice (Poison IV Treatment): Rebranded generic poison IV ointment and utilized cheap Google ads. This venture was shut down after two months, deemed a "dumb idea" and a waste of time, emphasizing the need for substantial business concepts.
11. Weekend Copywriting Class: Co-hosted a class with a friend, Neville, earning $10,000 each. This demonstrated success in educational workshops.
12. HustleCon: Organized a conference for startup founders, generating around $40,000 in profit. Subsequent iterations saw revenue double each time, indicating strong growth potential in the event space.

The Big Win: The Hustle

13. Pivot to Media Company: With $300,000 saved, HustleCon was pivoted into a media company called The Hustle. After six months of extensive article writing, traction was good, but consistently driving website traffic proved challenging.
14. Newsletter Pivot: The most significant pivot was from a blog to a newsletter. This shift proved highly effective, with the business model described as a "rocket ship." By year four, it achieved $12 million in revenue, leading to the company's sale when the speaker was 31.

Current Ventures:

15. The Hustle's "My First Million" Podcast: The speaker co-hosts this popular podcast, which has over 700 episodes and hundreds of millions of downloads, positioning it as one of the world's most popular podcasts.
16. Hampton: Described as the most impactful and fun venture, Hampton creates peer groups and chapters for founders generating at least $3 million in annual revenue. It aims to combat loneliness and provide a supportive community for entrepreneurs. The company has a team of 20, primarily in New York City. The speaker invites eligible founders to check out hampton.com.

Key Lessons Learned

The speaker distills crucial takeaways from this extensive entrepreneurial journey:

1. Stay Focused: The speaker admits to quitting on ventures prematurely that could have potentially succeeded if sustained focus had been applied.
2. Everything's Hard: Even successful ventures require significant effort and are not without their challenges.
3. Find Smart People: Surrounding oneself with intelligent individuals who provide accountability, maintain humility, and offer a listening ear is essential for navigating the long entrepreneurial path. The speaker emphasizes that this journey cannot be undertaken alone.