A VC shares his favorite question to ask founders

The best investor questions are usually designed to reveal clarity of thinking rather than produce a “correct” answer.

A founder’s ability to reason through uncertainty, priorities, and tradeoffs often says more than polished metrics or pitch narratives.

"Why should it matter whether the entrepreneur had taken five vacations or fifty vacations over the past year, the traction of the business you’re evaluating is what’s important, right?”

Wait, "five vacations or fifty"?? Is five vacations per year the interviewer's minimum conceivable frequency in this scenario?! I've take a total of one vacation in... in I don't even know how many years. Five per year??

I've gotta re-evaluate some things. 😅

TLDR: He asks them when is the last time they took a vacation.

He then prefers to invest in those who have:

a) Taken regular vacations
b) Haven't taken any vacation in years and are ashamed when they say it. He invests in these people because after he gives them funding, they can delegate and finally take a vacation.

So, this VC actually said he’s, “even funded a few founder vacations.” Which, I’ll admit I find it a little hard that he's that committed to founders taking time off. And yet, it’s pretty well known that it is very difficult to raise venture capital between mid-November through January and mid-July through September 7th. Because...VCs are on vacation. So maybe I should be less surprised by this?

I coudn’t get pass the pay wall what's the question!?

There's a conspicuously absent detail here: How successful is this VC? Or more to the point: what are the performance outcomes of his vacation-friendly founders relative to a control group of anti-vacation founders who obsess over their businesses year-round?

Without an answer to this question, this VC's advice is just a rorschach test: pro-vacation people will applaud, and anti-vacation people will boo.

I like his view on taking regular vacations. I honestly hate when people wear the "I haven't taken a vacation in five years," statement as a badge of honor. I don't know whether to believe it's true, I mean, can anyone really go that long without a break? I just can't ever gauge whether people say that because they think I'll admire them more for their "devotion" or whether it's a strange intimidation tactic. Either way, I'm skeptical.

Oh wow, he makes a great point. I've helped a couple of friends prepare for pitches and each time they tried to prepare responses to the VCs' questions. When, in reality, it might have been a better approach to anticipate what they were going to ask so they could cover everything in their pitch as opposed to waiting to be asked about it.