Sublime

However, remember that we want your first ten investments to be $1,000 syndicate-level swings at bat so you can learn at the low-stakes table, where mistakes aren’t devastating. After that, in this book, we talk about making twenty $25,000 bets and quadrupling down on the winners with a $100,000 follow-on investment.

The company's strategy is simple. Acquire small vertical software businesses with little competition, apply best practices from past experience and repeat as often as possible.

Perhaps more important than the venture firm itself is the specific partner that leads the investment—because, almost always, the partner who leads the round will join the startup’s board of directors. “We have always, always, always solved for the person joining the board,” Michelle Zatlyn, the co-founder of Cloudflare, told me. “It didn’t matter

you’re looking to do something super simple, we’d recommend buying a Facebook group or a podcast, a social account, or some other bit of media. Those are easy deals to find and close quickly.

Leo Melamed, Man of the Futures: The Story of Leo Melamed & the Birth of Modern Finance

1. the need for cash to grow; and 2) the desire to avoid dilution.

Startup founders often sell too early, leaving money on the table. VCs often force founders to hold out and swing for the fences, risking blowing up companies and locking in gains. We angel investors are generally along for the ride. The good news is that our industry has figured out this divergence of interest and has come up with an effective way