Ten Years: The Best Deal I Ever Closed
Today marks 10 years with my wife. It also happens to be International Women's Day.
After a decade of startups, fundraising, exits, and all-nighters — I can tell you with certainty: the best deal I ever closed was at a sushi restaurant in 2016.
I was a vegetarian. She hated seafood. The due diligence should've killed it right there.
Before me, Amanda's operating model was flawless. Applebees on Sunday. TGIF. BJ's on Friday. Asleep by 7pm. Vacations planned 14 months out with a color-coded spreadsheet. Backup plans for her backup plans. The woman ran her life like a Series A company with zero burn.
Then she took a meeting with a guy who had no plan, no spreadsheet, and a pitch deck that was basically "trust me, it'll be fun."
Since then:
📈 Her blood pressure — up
😴 Her sleep schedule — destroyed
📅 Her planning horizon — went from 14 months to "hey babe, we're leaving Thursday"
(she still goes to bed at 8pm tho)
But also:
🎢 Adventure — 100x
👶👶 Two tiny humans who are somehow better than both of us
🌍 A life neither of us could have modeled in a spreadsheet — which is ironic, because she used to spreadsheet EVERYTHING
Every founder talks about the person who makes it all possible. Amanda isn't behind the scenes. She IS the infrastructure. I chase crazy ideas at 2am because she already handled everything that actually matters.
She's still here. At this point I'm pretty sure she stays because nobody else would deal with either of us.
10 years. Best bet I ever made. Highest ROI in the portfolio.
Happy Anniversary, Amanda. Happy International Women's Day. ❤️
After a decade of startups, fundraising, exits, and all-nighters — I can tell you with certainty: the best deal I ever closed was at a sushi restaurant in 2016.
I was a vegetarian. She hated seafood. The due diligence should've killed it right there.
Before me, Amanda's operating model was flawless. Applebees on Sunday. TGIF. BJ's on Friday. Asleep by 7pm. Vacations planned 14 months out with a color-coded spreadsheet. Backup plans for her backup plans. The woman ran her life like a Series A company with zero burn.
Then she took a meeting with a guy who had no plan, no spreadsheet, and a pitch deck that was basically "trust me, it'll be fun."
Since then:
📈 Her blood pressure — up
😴 Her sleep schedule — destroyed
📅 Her planning horizon — went from 14 months to "hey babe, we're leaving Thursday"
(she still goes to bed at 8pm tho)
But also:
🎢 Adventure — 100x
👶👶 Two tiny humans who are somehow better than both of us
🌍 A life neither of us could have modeled in a spreadsheet — which is ironic, because she used to spreadsheet EVERYTHING
Every founder talks about the person who makes it all possible. Amanda isn't behind the scenes. She IS the infrastructure. I chase crazy ideas at 2am because she already handled everything that actually matters.
She's still here. At this point I'm pretty sure she stays because nobody else would deal with either of us.
10 years. Best bet I ever made. Highest ROI in the portfolio.
Happy Anniversary, Amanda. Happy International Women's Day. ❤️
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