My developing thesis: 1. $7 trillion of profitable small businesses will change hands in the next 25 years -- 👋🏻 bye Baby Boomers. 2. Virtually no one is focused on buying these sub $15 million businesses. Too big for an individual. Too small for private equity. 3. You can *still* buy these assets for 3-4x their annual profit. That's a ~30% year 1 return with no debt and no growth. 4. Most ambitious peers are trying to build the next billion-dollar company. There's a lack of sophisticated operators in this space. 5. Content is the flywheel. Sharing the journey publicly attracts proprietary deal flow, the right investors, and the best talent. To be clear: I am not the first to identify this opportunity. Folks like @BrentBeshore @awilkinson @SievaKozinsky @XavierHelgesen are way ahead of me. But hey - I think we're in the 2nd inning of a 9-inning game. There will be many winners.

Broker sent me a CIM this week for a content business doing $450k in revenue and $150k in gross profit. Asking price: $6,500,000 Be careful out there folks...

Recent conviction: I need to ask more/better questions. As the business owner, my job is not to solve problems. My job is to find and motivate great people to solve those problems. Every time I proactively jump in, I toxically undermine their accountability.

Raising equity deal-by-deal is a suboptimal approach for anyone trying to buy multiple cash-flowing businesses. You may lose a deal because you can't raise the money in time. Your investors are concentrated in a single business, rather than a diversified group of businesses. You don't have the opportunity to reinvest pre-tax profits into other businesses you own. A single raise to fund multiple acquisitions is better for everyone, especially when buying volatile small businesses.

If you acquire a business for 3x its annual cash flow, use no debt, and keep the business flat, you would generate a 33% year 1 cash-on-cash return. 4x = 25% 5x = 20% Stop fixating on purchase price. Instead, focus on your ability to mitigate risks and grow the business.

Seems like daily I get asked: "I'm 23 and have $25k in savings. Should I use that to buy a $1,000,000 business?" No. Instead, go find a well-paid job working for someone you admire. Learn to read a P&L, structure deals, manage people and save cash. Jog before you run.