What if the opportunity you've been waiting for isn't something you can buy your way into? In this episode, I break down the single best investment I've ever made - and it isn't the startup round that's now worth 21 times what I put in. I share how a $2,000 dinner in Los Angeles in 2011, back when I didn't know anybody, turned into the network that still brings me every deal worth having. Tune in to hear why proximity is the asset you can't replace, and what to do about it if you're the smallest fish in the room right now.
In this Episode, You Will Learn
- The investor-call slide that made me stop and reread it.
- Why a 21X valuation still isn't the best investment I've ever made.
- How I went from knowing nobody in Los Angeles to filling rooms with the people I wanted to meet.
- The $2,000 dinner bill that quietly started all of it.
- Why startup investing is one of the worst bets you'll ever make - and why I keep making it.
- The friends-and-family round I'd have never been invited into without one dinner.
- What to build, or buy into, if you want the same kind of deal flow.
01:25 The investor call that reset the math
02:46 The slide I couldn't believe
03:11 Why 21X is not my best investment
03:32 2011: a fish out of water in Los Angeles
04:15 Why I started buying dinner for strangers
05:08 The $2,000 bill that started everything
07:28 The dinner where I met the founder
08:42 The text that opened the round
10:11 Why startup investing is usually a losing bet
10:45 Deal flow comes from proximity, not luck
12:49 The network I still call on today
14:09 Build the room, the table, or the stage
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