“I have to be a little bit skeptical, or I’d invest in everything. But it’s also my job to ask myself ‘What if it works?’.”
If you invest in startups, you have to hit a delicate balance.
You can’t give everyone a check . And yet, you have to believe that some of these little companies will make it.
So lately I’ve been struggling with this question: how much skepticism is too much?
I Wanna Get Cynical, Cynical
I dug into this problem with a friend Saturday night.
We’re in different industries, but we agreed on one thing: when we don’t take time off, we get cynical.
The longer I go without a day off, the more every company starts to sound the same. Instead of seeing the good points, I tend to see the flaws.
For her working in law, unrelenting work gets her snapping at underlings and not being who she’d like to be.
“In 2021, I took only five days off,” I explained. “Eventually, one startup ran into the next and I didn’t even know what I was looking at anymore. That’s when I decided that I needed to give myself PTO days.”
My Boss Is a Jerk…I Work for Myself.
These days, I budget a very generous 20 days per year plus holidays— up from zero.
I used some last year to visit Porto, Portugal.
I wandered around, looked at cool buildings, ate like a prince and read the Elon Musk biography. I did meet one founder — I can’t help myself! 🙂
I came home refreshed and ready to attack. That’s the mode I want to be in.
We Think We’re Rational, But…
As angels and VC’s, we’re surrounded by the new.
It’s super fun! You see all the coolest stuff before most people know about it.
But digesting mountains of new information every day wears your brain out. It needs a rest.
When I’m worn out, I view startups differently. “That’s such a crowded market, no thanks,” I mutter to myself as I read a slide deck.
Had I just come back from vacation, I might’ve said, “Look at that product velocity! I’m in!”
We humans like to think we’re purely rational — especially in tech. But we’re not.
We get tired. We get cranky. And it effects everything we do.
Wrap-Up
Any early stage deal you see will have 100 problems. Minimal revenue, tons of competitors, an unclear sales strategy.
If you want to find flaws, you certainly can.
But as Don Valentine supposedly said, “We are in the business of making investments. We are not in the business of not making investments.”
So I’m making time off part of my strategy. A few well-timed breaks per year can help me stay fresh, ready to see what’s awesome in your company.
Now, when can I find time for one with all these meetings…
How do you balance skepticism and enthusiasm? Leave a comment and let us know!
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