Write the Check, Then Watch Yourself Perform

Our first anchor client lays it out plainly. The building gets its certificate of occupancy on a fixed date, seven months out. Either our system is running by then or the deal is gone, and so is the roughly six-figure investment it takes to build it.

I write a personal check to front it.

Here's the line I've used ever since: write the check, and then you'll watch yourself perform.

Why does skin in the game change how you perform?

Before the check, a decision like that lives in your head as a debate. Should we, shouldn't we, what if. Every hour you spend in that debate is an hour you aren't spending on the work. Once the check clears, the debate is over. The only question left is how to deliver, and that's a question an operator knows how to answer.

That's my read on it. When your own money is on the line, you stop hedging. You make the call today, and you go looking for problems early, while they're still cheap to fix. Seven months is not a long time to stand up something new in a building, and there was no slack in it for indecision.

The client wired payment the day after grand opening. They're still a client, many buildings later.

Was writing that check reckless?

Someone asked me that on LinkedIn, and it's a fair question. It didn't seem aggressive, even in hindsight. I had lost on other ventures before, so I knew what a bad bet felt like. This one had very hard lines on all edges. Customers were already telling us they'd pay for it. I knew the market and I knew the upside. And I trusted the team to deliver.

The only risk was in not delivering.

When the outcome depends on things you can't control, like a market turning or a buyer changing their mind, personal money on the table is a gamble. When the outcome depends mostly on execution, and execution is in your hands and your team's hands, the check is a commitment device. That's the distinction I'd ask any founder to make before he writes one.

We didn't make money on that first project. It was the relaunch of a great company, and the client's feedback shaped the roadmap that came after. A first project that loses a little and teaches you a lot is a good trade.

How do you know when to bet on yourself?

Run three checks before the money moves.

First, set the hard lines. Know exactly what success looks like and when you'll know. A certificate-of-occupancy date is about as hard as a line gets. If you can't name the line, you can't size the risk. This is the same discipline as Keep or Kill: decide the timeline before you start.

Second, find out where the risk actually lives. Is it in demand, or is it in delivery? If customers are already saying yes, the demand question is answered and what's left is on you.

Third, look at the team. A bet on yourself is really a bet on the people next to you. If you wouldn't hand them the keys, don't write the check.

One more thing. I've had investors in many ventures, and I treat their money just like it's mine. The check discipline doesn't change when the money belongs to someone else. You size it the same way and you perform the same way.

What's the decision you've been debating that a little skin in the game would settle?

~b