Co-Founding is not a Marriage

4 minute read

I write new articles and publish them to Substack if you want an easy way to keep up. I hope you’ll subscribe!

Read more product and company-building articles


  1. Founder dating is a stupid concept.
  2. Look for signals around responsibility, accountability, and cultural alignment (and whose ego comes first).
  3. Make sure you are on the same page about the company you are pursuing and risk tolerance.

A reader asks…

Well, let’s knock out a few of these at once.

How did you decide to work with Greg as a co-founder?

How do you vet a person as a co-founder, especially if they’re not technical?

What happened at Xobni?

90-Day Co-Founder: Happily Ever After?

sure, let's get married

Potential founders often asked me how to find a co-founder while I worked on Dropcam and did angel+VC investing. Some would mention founder dating, as in “I met someone, worked with them for a few weeks, and now we’re co-founders.”

There is a whole Silicon Valley subculture focused on this problem, and they have events and networking opportunities to bring people together. Usually it’s “business” types looking for “engineer” types, or vice versa.

I would usually roll my eyes at this concept because of two things:

  1. Working on one project is not enough, even if it’s for a few months. Everyone is on their best behavior when you’re explicitly dating, and the obstacle you’re facing is usually some sort of engineering or product milestone, not a holistic business or company problem.
  2. Bringing together complementary skillsets is difficult because everyone wants to be a visionary.
  • Business types think they need “coders” who will listen to their product vision.
  • Engineer types think they need “someone to handle the copy and cold email” and will listen to their product vision.

At the beginning, everyone should be gathering information about the business and product and synthesizing the results together.

If you don’t want to do that, it’s okay! Then just say you’re a solo founder, hire your first employee, and give them explicit tasks.

Looking for a mind at work

Ideally, you’ve worked with your co-founder before. That’s obvious - school, office, siblings, whatever. Hopefully you’ve worked together enough that you can figure out:

  1. Do you respect each other’s complimentary skills? And could those be separate responsibilities when it comes to your co-founding team?

  2. How do you each respond when things go sideways on a project? Do you act like a team or point fingers? Have you held each other accountable?

  3. Are you culturally aligned with where you want your careers and lives to go?

Greg and I met at Xobni1. All you really need to know about the company is that it was a blown opportunity with negative responses to the above questions.

Over the course of one year, Greg and I worked on a few projects together, so we saw how his coding prowess melded with my organization and project management skills. And we both really wanted to build stuff that people would pay for (like a CRM in Outlook - this is 2007 remember), not just gather eyeballs and wait to monetize in the future.

hamilton is amazing

While dealing with founder fighting, a belittling CEO, a failed acquisition2, and the resignation of our head of engineering, Greg and I kept working and launched an invite system for the core product. And I tried to keep the small team running while dealing with shady promises3.

And going to Starbucks. Lots and lots of Starbucks.

Tip: If your ICs are leaving the office to get coffee, they’re plotting.

Pro Tip: If everyone in your office is leaving the office to get coffee, you have a culture problem4.

Getting verklempt

Coffee fueled three things we saw as lessons from our Xobni experience.

  1. Build a product people would pay for.

We didn’t want to capture eyeballs and pray for monetization later. If we had to hold a car wash, we’d do it to make $1 in revenue in our first year.

  1. Respect our employees and be transparent.

If we were unwilling to talk to employees about something as founders/board members, we would say so instead of lying or obfuscating.

  1. Avoid burnout and build a long-term culture.

At the beginning, everyone at Xobni worked long days and weekends. By my sixth month there (and especially after the acquisition attempt), everyone was burned out.

At the same time, Greg was married and wasn’t getting time with his wife. So we agreed on wanting a culture that respected family, as that external support would be necessary to have happy, engaged employees when we were in the office.

We had seen egos destroying a company and realized we wanted to nip that in the bud. It led to the napkin discussion I mentioned in the last post.

90's SNL reference!

And one more thing…

Greg and I left Xobni at different times, and we kept meeting up for coffee. During this time, we discussed product ideas and aligned around one more thing.

This was it.

We were going to start this company and it was going to be a place we figured things out. We weren’t looking for a quick exit. We weren’t looking to be acqui-hired.

We were going to get big or die trying.

  1. Still a joke link. 

  2. This is when you learn TechCrunch was shitty reporters and a shill for Silicon Valley. Microsoft walked away. 

  3. If you really want to hear about anti-mentors, let me know! 

  4. Why are people leaving the office? Is it to find a way to clear their heads or to get away from the shitshow?