Most diligence starts with the pitch and looks for reasons to say yes. I do the opposite: I start by building the strongest possible case against the company, and only invest if the idea survives it.
The move
Before I form a view, I write down the version of "this fails" that a smart, informed sceptic would give. Not a strawman — the steelman. Then I put the founder's thesis next to it and see which one bends.
The strongest counter-argument is the best diligence tool you have. If you can't beat it, you've just saved yourself a cheque.
The checklist
- What would have to be true for this to be a big outcome — and how many of those are already true?
- What's the failure mode the market will find before the founder does?
- Why now — what changed that makes this possible today and not three years ago?
- Why this team — have they felt the problem first-hand, or read about it?
Draft — to finish
*(Outline notes for later: add two real examples from the portfolio; contrast a bet that passed the steelman with one that didn't; close on why conceding fast is a competitive advantage.)*