When you’re running a company, you’re deep in your own narrative. Every decision feels unique. Every challenge feels unprecedented. You’re the protagonist in a story you’re writing in real time.
When you’ve invested in 200+ companies, you see the patterns.
The founder who won’t delegate? I’ve seen that movie a million times. It ends badly 999,000 times. The team that pivots every quarter? That’s not agility, that’s panic. I can spot it in the first board meeting.
The market timing that feels like genius? Usually luck. The grinding execution that feels like it’s going nowhere? Usually the path to something real.
Here’s what surprised me most: the best entrepreneurs don’t have the best ideas. They have the best response to failure. I’ve watched brilliant founders with mediocre ideas outexecute mediocre founders with brilliant ideas. Every single time.
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The difference? When the original plan fails—and it always fails—the great ones iterate. The rest rationalize.
I invested in a company that pivoted four times in two years. Sounds like chaos, right? But each pivot was surgical. They’d test a hypothesis, gather data, kill it fast, and move to the next. No emotional attachment to the previous version.
That’s not chaos. That’s discipline.
The company that raised at a $15M valuation because the pitch was flawless? Dead in 18 months. The scrappy team with the messy presentation but relentless customer focus? Acquired for over $200M.
Patterns. Once you see them, you can’t unsee them.
