How Being a Founder Made Me a Better Parent (and vice versa)

If I hadn't been a Founder, I'd be an awful parent.

Now, I'm already giving myself too much credit here because it's assuming I'm not an awful parent, which let's be honest, many of us just might be. But I've definitely come to appreciate over the years raising my 5-year-old son and 10-year-old daughter how my best parenting traits are directly mapped back to what I've learned as a Founder.

Surprisingly, it really has little to do with "building a startup" and more to do with how I've come to think like a Founder.

The Power to Question Me

The day my son Wil was born, I wrote him a long letter. In it, I gave him all of the advice I had in me about preparing him for the world. The one piece that's always resonated the most was "Question everything, even me. Because we're probably wrong."

As a Founder, I've come to learn that you really do need to question everything, and the more you do, the more we unlock that power, the more you actually learn and achieve. I don't think in most careers that kind of "rage against the machine" vibe is rewarded, and for what it's worth, it's largely punished.

But being a Founder made me understand the beauty in second-guessing things. Does little Wil take full advantage of that request? Yes, daily! But I love that fact and truly believe it will lead him to find the path the's supposed to be on, not one I prescribed for him.

Start with Happy, then Work Backward

When I was growing up, no one ever really cared if I was "happy." They cared if I was "OK", but generally speaking, their focus as parents, teachers, and others foolishly entrusted with my care was just to keep me basically contented.

But I'm not OK with that as a norm for my kids. I want them to find out what makes them happy, then find a system to make it work for them. Sure, not everything is happy-fun-times (chores, homework), but that doesn't mean our kids need to be miserable.

I ask them "How could you do this in a way you'd enjoy?" because as Founders, that's what we're built to do. We build things that are incredibly hard and painful yet find the joy in them. I believe when we start with what makes us happy we're actually better at the task to begin with. Founders know this inherently.

The Innate Sense to Triple Click

Of all the little powers I've developed as a Founder, maybe the one that's serving me best is my innate sense to "triple click" (mouse button metaphor here) into problems that most people skim over.

I do this all day at work. It's not just OK to hear someone complain or raise an issue and respond directly. I have become conditioned to keep asking "Why are they asking that at all? If they are asking that, what other problems may have also cropped up for this one to be an issue?" And so every time I pull that thread, and every. single. time. there is way more to the problem.

With kids it's invaluable. 99% of the time when they raise a concern it has very little to do with the actual concern. My daughter isn't actually upset about her homework, she's upset about how she thinks we'll judge her if she does it wrong. I've learned to source the root of problems, never just the problem itself.

All of these things have combined together to make me feel like I'm doing something truly special as a parent, even though I'm probably screwing a ton of stuff up. Our little traits, while quirky, may just make us even better Founders than we were parents. At least, we can hope.

In Case You Missed It

What Happens After I've Made It? We always dream about our startups making it big. But what happens when they really do? What happens when all of the risks actually turn into the payouts we had always hoped for? Are we actually happier?

What to Expect in the First Year (podcast). As Founders, we think we know how our products and businesses will look and function for years to come, but as with time, it's nearly impossible to expect the unexpected.

Retiring Early is a Broken Concept Retiring isn't really our end goal, so we shouldn't aspire to it. What we really want is to shape our life the way we want them to be.