Co-Founder Dating 101: Lessons From 60+ Founder Dates
Disclaimer: Contrary to the cover photo’s implication, this article is not about dating your co-founder. I do not recommend you do that 💔
If you’ve spent any time in the early stage start-up landscape, you’re probably familiar with Co-Founder Dating. This refers to the process of searching for your startup partner. These rare kindred spirits are entrepreneurs willing to put in the long, sleepless hours with minimal expected payoff in exchange for the minuscule chance of making an outsized impact on the world.
In November 2020, I had just winded down my first startup and was full-time co-founder dating. Over the next 3 months I met with over 60 founders, which is exhausting enough without factoring in that these were Zoom meetings. I took extensive notes on each conversation, which ranged in length from 30 minutes to 2+ hours. After the first few meetings, I realized that it would be prudent to come up with a more objective framework to benchmark each opportunity.
Just as I enjoy asking my dates what they look for in a significant other, I ask all founders I connect with what they look for in a co-founder. When grouped together, there’s a surprising amount of overlap in desired traits. From these trends in conversations, I’ve evaluated the strongest indicators of good co-founder chemistry and success.
In this post, I’ll outline 6 Co-Founder Dating Questions that will help you find your startup soulmate. If you answer no to any of these, answer no to them. Don’t settle, you can do better. You’re a catch, don’t let anyone tell you otherwise.
1. Do you vibe?
“I’m looking for a co-founder I can get fucked up with.”
— Potential Co-Founder & Partner at an A-tier VC Firm 🍻
The founder above had an interesting idea, a good approach, and a strong background. When they mentioned what type of co-founder they were looking for, I had a good chuckle, but it was definitely off-putting. I’m not sure I’m ready to go the distance with someone who leads with getting fucked up as a requirement. Guess I’m lacking that big VC energy.
Also known more colloquially as the vibe check, for many this is the most important consideration in vetting a potential startup partner. If you plan on going the distance with a co-founder, you plan on spending more time with them than any other person in your life — 8 to 12 hours a day, every day, for the next 4 to 10 years. If you don’t enjoy your first conversation with them, you’re not going to make it to the thousandth.
Here are some key questions to ask yourself:
- Am I excited to have a conversation with them?
- Did we naturally go over the scheduled meeting time?
- Do I respect what they have to say?
- Is this someone I can talk to for hours without wanting a Xanax?
2. Does their technical skillset complement yours?
“I have an idea for an app. I can handle the business side, I just need someone to write the code.”
— GSB, HBS, or Wharton MBA Graduates 🐍
While founders will be forced to wear many different hats throughout the startup development lifecycle, each should specialize in their own relevant skills. At a high level, this includes but is not limited to programming, design, business development, data science, recruiting, and sales. Your co-founders should cover your weaknesses — avoid doubling up on specific areas of expertise.
3. Does their personality complement yours?
“Kylie is a Leo and I’m a Libra, and it turns out these two signs are super complementary and good for each other.”
— Kim Kardashian ♌️
There’s little to no chance you’ve made it this far in life without working on some kind of group project, be it a work epic, a university assignment, or a little league team. At this point you should be aware of what type of person motivates you to do your best work.
For example, I’m the type of person who’s fairly easy-going and tends to improvise when necessary, and my co-founder for my previous startup is similar in that regard. While this makes us great friends, it means that when someone needs to step up to define roadmap and planning, we’re both a little out of our element. The improvisers benefit greatly from the planners. Consider your own personality under this lens. Are you a real deep work type, someone who loves to be heads down developing? Perhaps look for someone with the extrovert energy to seek out conversations.
That’s not to say your co-founder should be totally different from you. There are many traits that benefit from alignment: approaches to conflict resolution, taste in hobbies & entertainment, stances on recreational drug use… you’re just Jobs looking for Wozniak (or vice-versa if that’s somehow more appealing to you).
4. Are they flexible?
“A tree that is unbending is easily broken.”
— Lao Tzu ☯️
I’m cheating a little here, this one refers to flexibility on two dimensions. In some contexts, you’ll need to evaluate both, and in some you won’t need to evaluate either.
Are they full-time on the startup grind? Not everyone you meet is going to be in the unenviable position of searching for a co-founder full-time. For those who are thinking of making the leap, it often makes sense to spend some time proving concept before taking a startup leap of faith. I worked on my last startup with two part-time co-founders, to varying degrees of success —avoid this scenario if possible. Part-time co-founders don’t last too long, so in these circumstances, there are a few things to consider:
- What would need to be achieved before they’re willing to take that leap?
- How comfortable are you with them not being full-time, and for how long?
Are they a flexible thinker? The startup road is never straightforward; there are many twists, turns, and pivots along the way. If they have a specific idea in mind, they must be open to inevitably changing the details. You want them to love the problem not the solution. They should have strong opinions, weakly held.
Many potential co-founders you meet will have a set of problems they’re interested in tackling or even a specific product they’re building out. The final two heuristics can be applied for scenarios where the founder is already working on an idea.
5. Do they have Founder-Market Fit?
“Richard, you’re a fucking rock star, okay? You just don’t know cloud, this tiny, little, shitty area, which is becoming super important, and in many ways is the future of computing.”
— Erlich Bachman, Co-Founder of Aviato ✈️
There’s an argument to be made that given enough interest and passion, you should be able to dive into any vertical and become an expert. I believe there’s some merit to that. I think we can all agree, however, that most verticals will benefit greatly from context.
If you’re interested in building a payments and loans application, you have a big leg up if you have a founder with strong experience in the legal and compliance work that surrounds it. If you’re interested in building a recommendation based product, you better have a founder experienced in Machine Learning.
Relevant work experience also has the added benefit of customer empathy. If you’re familiar with the problem you’re trying to solve, then you can better understand the pain points, the willingness to pay, the preferred features, and much more.
For example, my last start-up attempted to solve the existing information asymmetry between influencers and the brands that hire them by building a Glassdoor for Influencers. However, we were working on a product for influencers when none of us were influencers ourselves, nor had we worked in the creator economy before. User interviews were insightful, but even securing those conversations was an uphill battle. A team of influencers would be much better positioned to solve that problem.
Key insights from relevant experience can take a founding team from good to great, so make sure they’re experienced in the problems they’re trying to solve.
6. Do you care about their core problem statement?
“Running a start-up is like chewing glass and staring into the abyss. After a while, you stop staring, but the glass chewing never ends.”
— Every startup founder profoundly quoting Elon 🧠
The highs and lows of a startup come and go so frequently that you’ll begin to question your mental stability. There comes a point where even the smallest of victories becomes the hope you latch onto. If you don’t have an innate belief in the vision your company is trying to achieve, you’re never going to survive those days when a critical employee leaves, you fail to secure a big customer, and every top tier venture firm has passed on your next round.
Some founders you meet will be committed to a specific problem space. Ask yourself if you’re enthusiastic about the space after talking with them. If you don’t deeply care about solving your customers’ problems, you will not succeed.
This is just the tip of the iceberg in the co-founder dating journey. Roughly 20% of the conversations I had met these criteria, warranting follow-up conversations. Those conversations were much deeper dives into their motivations and values, and the considerations there are more complex as you attempt to build trust in their abilities and conviction, but that’s a conversation for another post.
For those looking to increase their pool of potential co-founders beyond their personal networks, there are many useful communities and tools being built to facilitate those conversations. I’d personally recommend Y-Combinator’s Co-Founder Matching Platform or On Deck’s Founder’s Fellowship for high intent prospects. For product and engineering leaders, consider applying to Fractal.
Follow me on medium (@chongz) or twitter (@chongzluong) to continue listening to me shout nonsense into the tech ether.
