The Entrepreneur Test

I have a question I ask people and it has cost me at least two friendships. ;)

Not because the question is offensive. It's actually a pretty reasonable hypothetical. But there's something about being cornered at a barbecue and asked to evaluate your relationship with sacrifice that people find, at minimum, weird.

The question is this:

Would you give a year to get a year?

Here's the setup. Imagine your dream job. Not a lottery win. A real position, doing work you actually want to do, paying what you deserve. The catch: you have to make it your full priority for one year. Long hours. Work comes first. You miss some things.

In return, you get that exact salary for a free year. No job. No strings. Go wherever you want, do whatever you want. A full twelve months of complete freedom.

Would you take it?

I've asked this to everyone. Friends, family, people I've known for twenty years who apparently did not anticipate this becoming part of our relationship. Most say no.

And here's the part that still gets me: it's a good deal. By any reasonable math, it's a great deal. But they can't get past the soccer games, the weekends, the balance. I sweetened it to two free years. Then three. One person looked me dead in the eye and said, "Gil. I just want to watch TV sometimes."

Which is, honestly, a complete answer.

That's fine. It's not a judgment. It's information.

What the question is really measuring is this: do you see a year of sacrifice as a cost, or as a down payment?

Entrepreneurs see it as a down payment. The question isn't "what do I have to give up?" It's "what can I build with this?" That free year the test promises? A real entrepreneur isn't lounging on a beach with it. They're hiring, building, already setting up the next thing. Freedom and building aren't opposites for these people. They're the same activity wearing different shoes.

One honest note before I make this sound too clean: the test assumes you're well paid during that year. Most entrepreneurs starting out aren't. They pay themselves little or nothing for longer than they planned. The actual deal is harder than the hypothetical.

Now. Stanford.

Stanford Business School ran an exercise that has stuck with me since I first heard about it. They gave student teams an envelope with $5 and two hours to make as much money as possible. No other rules. Come back in two hours, present what you made.

One team sold restaurant reservations to people waiting in line on Saturday nights. Hundreds of dollars in a couple of hours. Clever.

Another team set up a free bike tire pressure station, then switched to donations. Turns out customers paid more when they felt like they were giving back than when they were paying for something. Also clever.

The team that made the most never touched the $5. They never touched the two hours either.

They sold their three-minute class presentation slot to a company recruiting Stanford students. $650. Highest return in the room.

Everyone else was looking at the $5 and trying to multiply it. This team looked at the whole situation and found the thing nobody else had noticed was for sale.

Same resources. Completely different results. The only variable was how they framed the problem.

That's the entrepreneurial mindset. The skill is spotting the real asset in a room full of people who are all staring at the $5.

So. Back to the barbecue.

Would you give a year to get a year?

If your answer is yes without a long pause or visible wincing, you might already be thinking like an entrepreneur. If the answer is "it depends," that's worth sitting with. There's no wrong answer. There is, however, an honest one.

Not everyone should start a business. But the ones who should already know. They answered before I finished asking.

— Gil