Why I Decided to Start a Startup

Why I decided to start a startup.

Why I decided to found a firm.

Why I decided to commence a conglomerate.

Why I decided to create a corporation.

Why I decided to begin a business.

Why I decided to launch a venture.

Why I decided to do a startup.

Why I decided to produce an organization.

Why I decided to setup an outfit.

Why I decided to generate an enterprise.

Why I decided to undertake a establishment.

Why I decided to make a firm.

Why I decided to instigate a venture.

Why I decided to originate a organization.

Why I decided to bring about a business.

Why I decided to embark on a journey.

Sorry, “start a startup” is such a funny phrase to me. I can’t help but think of all the different ways to phrase it. Anyways, I recently did this. I wanted to write down my thought process.

What do I want?


I want the opportunity to die by my own sword. I’ve worked at startups my whole career. I’ve even had the privilege of leading teams with a high degree of autonomy at some of them. When I reflect on my career, the most frustrating parts were when I disagreed with the company’s direction. I want the buck to stop with me this time.


I want my day to day to be fun. I love the energy of small teams where ideas are flowing, memes are flourishing, and people are able to play off one another like a jazz band. On top of that, I find myself energized by all the minutiae you’re presented with as a founder (what’s our culture, what health plans do we offer, should we get an office, etc).


I want to be well compensated. At a glance, this seems at odds with starting a startup. This isn’t my first rodeo though. After a decade of working at startups, I know I have the skills to win. I think you probably shouldn’t start one unless you have deep conviction you’re capable of winning. It will carry you through the moments of doubt.

Other considerations


I’m 31. I’m not getting any younger. I might have children in the near future. My window of being able to pour everything I’ve got into something seems like it’s closing. I felt the right opportunity came my way and that I should take it.

Opportunity cost

I could go work at a large tech company and make a bunch of money, but I’d be lacking in the ownership and fun departments again. I figure if this doesn’t work out, they’ll still be around after.


To be honest, this was a decision I struggled with. I was coming off really weird time at Better (a story for another day perhaps). I had a lot of interesting opportunities available. I was stuck in analysis paralysis trying to decide what to do. I asked a friend for advice. They told me to think about what I might regret not doing. After that, everything became clear.