How I "dated" 19 potential co-founders to find the right one

I spent about 18 months "co-founder dating" and met with a total of 19 potential co-founders - 3 through referrals, 2 through CoFounders Lab, 1 through LinkedIn, 1 through Bolster, 12 through Y Combinator's Startup School co-founder matching platform. I met 4 of them in-person.

I moved forward with 2 co-founders (both of whom we met in-person) -- 1 in 2020 and another in 2021. The first one didn't work out after working together for a few months -- not because we didn't work well together, but because we realized that the answer to product-market fit meant changing the nature of the product in significant ways that no longer interested one of the cofounders to continue working on it. We parted ways amicably and still stay in touch.

Trying to find someone to work with on a new venture takes a lot of time and discipline. Not only do you need to work well with this person, you also need to align on a plethora of areas including how long they are financially able to work on the venture without pay, what point the person wants to exit the business, how they think about equity distribution, how long they'd be willing to work on the venture, the strength of the business idea, the amount of market research done to determine whether the potential customers want it enough to pay for it, the ability to create the product or service well, how comfortable you are in communicating openly and transparently with each other about difficult topics, and more. All of these have to align in finding the right co-founder. And no one is perfect, so figuring out priorities and how to mitigate risk across co-founders is also an important consideration. For example, if your co-founder is not very organized, can you help or figure out a good right-hand person to help that person stay organized? Or is the level of disorganization debilitating to an unsalvageable level? Can the other co-founder help shore up any of your own weaknesses so that you complement each other well?

Having previously served as a co-founder for another business venture (and successfully sold it after 16 years), I had learned the power of personality tests. We made better hiring decisions after we started using such tests as part of the interview process. As such, I am a believer of having potential co-founders do such tests to springboard discovery of natural inclinations for discussion. There are many of such tests out there available for free. I have tried many of them out, and they each give a slightly different perspective. Just pick one that you like best. It doesn't provide you with a hard green or red light on the potential cofounder but does provide you with some potential hot and cold buttons to discuss and get to know each other on a deeper level.

The 50 questions for potential cofounders template served as an invaluable tool in my conversations with the handful of potential co-founders that I shortlisted for more serious consideration. Those discussions helped us discover where we align or diverge in mindset and to inform our decision as to whether we're a good fit for each other. For example, 2 of the younger potential cofounders in their 20s told me they would be happy to exit at a $20 million valuation of the company and my mark is well beyond $100 million. As such, we quickly moved on to find better matches elsewhere without mutually wasting more of each other's time.

Next was a trial period to work on a project together for a period of time to see how well we communicate and enjoy working together. After which, we did reference checks. 

"If you can't see yourself working with someone for life, don't work with them for a day." -- Naval Ravikant, co-founder, chairman and former CEO of AngelList 

At this time of writing, venture-backed companies exit within 8 years on average. Starting and running a business is a marathon, not a sprint. As such, red flags to start are almost never a good sign. As it were, yellow flags often morph into red flags over time due to the constant annoyance that grates on a person's nerves. Hence, it's best to try to suss out any day-to-day working issues. There were a handful of the potential co-founders where just speaking with them irritated me till no end; I knew those weren't going to fly. As for the 2 co-founders I moved forward with, I actually enjoy chit-chatting with them about stuff well beyond the business itself. In other words, we enjoy each other's company and would hang out even if we weren't in a venture together. In fact, I found we were -- very quickly -- comfortable speaking to each other about "deep" topics that I haven't been able to do so naturally with others. For me, some of these topics include mental models, game theory, and other controversial topics.

I hope that sharing and outlining my process of finding the right co-founder could prove helpful for other entrepreneurs who have the need to find a co-founder that fits!