Founder Dating Ritual (beta)
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.