"You can't play four-dimensional chess when you can't see the board."
Here's the scenario: A founder, brimming with ambition, asks, "How can we make this VC invest?" or "What's the secret to making this enterprise buy faster?"
My response? "You f***ing can't."
You can't force people to buy anything. All you can do is make what you have look appealing.
Why?
Because in the world of startups, especially when dealing with VCs or large enterprises, you're living in a state of highly imperfect information.
It's like trying to play chess blindfolded.
- Is the VC partner you’re talking to coming off a run of iffy bets?
- Is the enterprise swamped with other priorities?
- Is there a crisis or strategic shift you're unaware of?
You simply don't know. And without seeing this metaphoric chessboard, any move you make is a shot in the dark.
So, what's my advice?
In a world where both sides have imperfect information, the best thing you can do is create more perfect information for the other side. You can't force them to divulge anything, but you can divulge anything you want.
So, be radically transparent:
✅ This is exactly what's going on.
✅ This is why we want to work with you.
✅ This is why time is of the essence.
The hope? If they have perfect information, they'll make a choice that's good for both of you. At the very least, they'll make a choice that's good for them.
And that's better than no choice at all.
Some might call this naive. I call it strategic trust-building. By being radically transparent, you create an environment where people WANT to work with your company.
And the assholes? They self-identify, and show themselves to the door.
In the high-stakes game of startups, you can't see the whole board. But by sharing your own moves openly, you are more likely to turn the game from competitive to co-op.
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PS. Startup founder?
I've got some time free on my calendar in the coming weeks and I'm dedicating it to helping people grow their startups.
Send me a DM saying “obvious” and we’ll have a chat - if what you do is in my wheelhouse, I'd love to spend an hour seeing if I can help you move the needle.