Founder dating ritual

The most important atomic unit of Silicon Valley is a team of two or three building something together out of nothing. I’ve been watching the team formation process over the last ten years and even though it’s more popular than ever to do startups today, finding teammates to work on a startup with doesn’t seem to have gotten any easier. Many people call this process “founder dating,” which is odd because I don’t think we actually treat it like dating. If founder dating were more like regular dating where there is a shared expectation of a sequence of events, I think we’d be able to form founding teams more efficiently. 

Founder dating breaks down into 1) meeting potential co-founder leads and 2) determining if they are the right co-founders for you. For meeting potential co-founders, there aren’t great solutions, but at least there are some things you can do like attending meetups, hackathons and dinners. Some dinners are even curated by experience, interest, skill set and status to help you meet the right people. You spend a lot of time in these events meeting people, hearing about their backgrounds, interests and the ideas they’re tinkering with, but you can’t really evaluate anything. You might click with someone because of shared interest, complementary skill set or personality, but then once you meet up, you’re pretty lost about how to move it forward. Some decide to work together right away. Other people mope around and never get anywhere. What’s certain is no one seems to know how to do it. We need an explicit ritual for founder dating just like in regular dating.

In regular dating, once you meet someone who you think could be a potential partner, you go into the universal dating ritual. Everyone sort of understands what that entails…

Disclaimer: This is obviously different for everyone. The point is that people roughly agree on the sequence of events, even when the details may differ. But still, be ready to cringe.

Regular Dating Ritual

  • Date 1: Have coffee/tea/drinks. Make sure they are who they said they are and they are not crazy. Check for basic chemistry and attraction. (30–60 mins)
  • Date 2: Have dinner. Learn about their values, ambitions, hobbies, quirks, and try to feel for an alignment in expectations (long-term, short-term, casual). Check for more chemistry and attraction. (1.5–2.5 hrs)
  • Date 3: Do an activity. See what they are like in-action: decision-making, sense of humor, attitude, aptitude. This is when most people begin to consider having sex with the person to see if there’s chemistry doing something they both enjoy. (1.5–3.5 hrs)
  • Date 4–10: Spend more time together, either talking, doing activities, or having more sex depending on what you think you need more information on. I have a friend who caps these to a maximum of 10 dates or 3 months, but you could keep this going for much longer. (Varies, but 10 dates over the course of 2–3 months seems reasonable)
  • Define The Relationship: At some point, you define the relationship and begin to put a label on each other and assume the responsibilities. After you are in a relationship, you can “break up.” At that point, it’s typically more painful because there‘s been more of an emotional leap and investment of time.

Because we all know this ritual, all Tinder needed to do was to match the two sides based on some basic criteria like looks, age, occupation and location. We are highly versed in figuring out the rest through dating. What does a universal ritual look like for founder dating? For the sake of more innovation everywhere, here’s my proposal…

Founder Dating Ritual (read this on Github

A ritual or an agreed upon sequence of events that everyone looking to work together on a startup or a long-term, high-commitment project can follow. 

  • Date 1: Have coffee/tea/drinks. Can you develop respect for this person? Would you consider this person potentially “your people”? Do you both want to swing for the fences, build a indie business or something else? Do your timelines match? Do your skill sets complement? Is the person mission-first, market-first or people-first? (30–60 mins)
  • Date 2: Have dinner. Can you hang out with this person? Do you enjoy talking about complex topics with this person? How self-aware is this person? How does this person think about building a startup? What are the motivations, ambitions, risk appetite, quirks, reasoning styles? (1.5 hrs — 2.5 hrs)
  • Date 3: Build and ship a weekend project, followed by a celebratory outside activity. It could be need-finding to convince yourselves a problem exists. It could be sales. It could be building something hackathon style. It has to be real enough with opportunities for tension. It has to ship to a real audience. You could work on one person’s 2nd or 3rd favorite idea so that there’s enough enthusiasm but no one feels too much ownership over it and therefore you lower the stakes. Learn about each other’s working styles. Evaluate the quality of the work. Get a sense of fit in terms of complementary skills. Sunday night, you can go do a fun duo activity to unwind: trivia night, board games, cook, work out. (2.5 days)
  • Date 4: Hang out with friends and family. This helps you feel for the “founder-life fit” to see if you both feel good about being intertwined in each other’s lives. Learn what the other person is like with their loved ones and see what their loved ones say about them. (1.5–3.5 hrs)
  • Date 5–10: Work together for at least four weeks on a project with terms that make sense (Steve Blank’s recommendation). If you worked on one person’s idea for the weekend project, come up with a new project together this time. (30 days)
  • Define The Relationship: At the end, take some time off to reflect and decide if startup life with this person is for you. Have an honest feedback session with each other about everything. Decide and commit. Standard startup vesting is four years with a one-year cliff. 

You can find the most recent version of this ritual on Github. Try it out by sharing this with your potential co-founders to get their buy-in. The more people who buy into the ritual, the more efficient founder dating will be and the more innovation can happen! Happy founder dating!

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