It’s too easy to get lost trying to build someone else’s business instead of your own.

Being a founder is hard. There are a lot of unknowns. We all have companies we look up to. An image in our mind of what we want our businesses to be. Someday, maybe. But the businesses we look up to should only be a source of new ideas, not playbooks. We can’t force our companies to be something they’re not.

Recently I’ve been trying to engrain this lesson deeply into my bones, so it becomes instinctual. We’re currently doing some planning for 2021 around what we should do with our company, Arrows. These decisions will have consequences, aren’t easy, and will be difficult to reverse.


Over a decade ago, while in college, I spent 4 days per week packing Field Notes orders. I checked the Coudal Partners homepage most days, while sitting in my school’s design lab, to see what cool new things they linked to. One day they added a link to a job listing and a few days later I was standing in the office of a bootstrapped company run by designers that I greatly admired.

Another blog I checked often was written by another Chicago-based design firm-turned-product company called 37signals, the creators of Basecamp. It turns out they rented desk space from Coudal Partners, so I got to know Jason Fried and some of the employees when they were in the office.

During college, as I was learning to program, I used an app called Beanstalk to keep track of my code changes. Over time I realized the folks who made it ran a pretty cool bootstrapped software company out of Philadelphia called Wildbit, and now years later I’m still a happy customer of their product Postmark.

These were just a few examples of the companies I admired around this time (and very much to this day still). A few months later, I left college early to take my first full-time job as employee 23 at Twilio. I greatly admire the company and Jeff, the CEO, who hired me as a nobody college student. But two years later I decided I wanted to leave Twilio, as well as San Francisco / VC-driven tech culture too, so I could do my own thing.


Over the years 8 years since I left Twilio, I’ve started multiple companies and built many products. The dream was always to be like the companies I admired… the Coudal Partners, 37signals, and Wildbits of the world. I wanted my own fully, purely bootstrapped success story. I wanted it run under my design studio, so we could build multiple products under one roof. Everything was run through this framework because I was so focused on that goal.

Occasionally I’ll find myself thinking about what the companies I look up to did and I’ll try to use that to guide us. But it can be a dangerous trap. They’re only useful guides to know directionally what type of business we want. Specific decisions need to be made about our own situation, and that alone.

The opportunity we have is different than what other companies we admire had. It could be better, it could be worse. The market, our timing, us as founders, our customers, the product, etc. What we’ve got now is what we’re building. I remind myself: Build THIS. Not what they did. Don’t tell yourself the story of your own company before it happens. Create it yourself.

Because what feels true and right for us, in this moment, may be entirely different with that framing. And possibly, if we’re successful, what we do will become inspiration to others later. But only if we follow our own path.

So it’s simple: Build the company that’s in front of you. Not the company you wish it to be.