This as-told-to essay is based on a conversation with Aaron Cannon, the 37-year-old founder of Outset, who resides in San Francisco with his wife and three-year-old son. It’s been edited for length and clarity.
I decided to start my company while I was on paternity leave.
It’s very woven together: starting a family and starting a startup happened along a similar timeline. I definitely have a lot of people who think that’s a little insane. It is. I have wistful moments thinking about, “Man, what if I could do all this when I was 25 and single?”
Then I quickly remind myself that I was an idiot when I was 25.
When I was on paternity leave, I maybe had too much time to think. When you have a baby, you are all hands on deck physically, but you don’t have a lot of intellectual stimulation. I was daydreaming about what I wanted to do with my career.
It’s a very intense balance. “Work-life balance” implies a certain degree of chillness. I don’t have that. Every minute of my day matters. Everything gets deprioritized except family and work. That’s painful. It’s really ruthless prioritization.
It’s very weird mentally. In a normal job, you have really intense days, and you come home and you tell your family, “I’ve got to take a breather.” The problem is, every day at my job right now is intense. Our startup is in that crazy growth stage where everything is growing and breaking at the same time.
If I come home and say, “Ugh, this is so intense,” then I’m not going to be as present as a dad. I don’t have that option.
Yesterday, on the way home, I had an intense call after work. I’m negotiating this contract. Then I pick up my kid, and I spend the next 20 minutes explaining seasons to him. I started with, “Do you understand what a year is?” No. Where do you even start? It’s a crazy mental shift.
I pick him up every day, which forces a boundary. Thank goodness, my cofounder and I have different lives. He stays later, I come earlier. As long as the two of us are showing up in the way the founders need to, great.
But I leave. I go and pick up my kid every day from preschool. I take him home. I do dinner. I get him to bed. Then I’m back on for work. Those are a precious couple of hours.
Even if I’m physically present, it is very hard after the most intense day of work to just shut that off. You can set physical world boundaries and still be mentally there or not there. I want to be as deeply engaged as possible.
We went through Y Combinator back in 2023, and I was definitely on the older side. On Wednesday nights, we had speakers and programs, and that was not easy for me.
Being a dad provides perspective. It is easy to take any big thing or small thing that’s happening and obsess as a founder. You are the company, the company is you. When I get home and have to explain what seasons are, it’s a reminder: Why are we doing this? It zooms you out.
It also helps reinforce my motivations. I want my kid growing up, seeing his dad do a big swing in his career and try something crazy. That’s a lesson and an example I want to set for him. You can go build something yourself.
It’s a chapter of my life, but it’s not all of my life. It’s intense. I should expect it to be that way.
The most important thing is that I’m present as a dad. I don’t get these years back. He’s only three for one year.
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