An in-depth guide to co-founder dating and how to find success by partnering with the right people.
If you’re chasing the startup dragon, one of the most important decisions you’ll make will be choosing the right co-founder(s).
Every potential co-founder relationship is different, but after going through this process half a dozen times, I’ve learned some extremely valuable lessons that I wish I would’ve known years ago.
The most important lesson is that it’s really useful to view this as a “dating process” which can be broken down into four distinct phases:
This is what I'm doing right now 🙂 If you're reading this, then you're aware that I'm actively looking for co-founders as well as getting a feel for who I am as an author and as a person. Feel free to reach out & say hi 👋
I believe this phase is critical and is often overlooked by aspiring founders. I'm hesitant to view this process as a marketing funnel, since it introduces some odd power dynamics into the mix whereas the best co-founder relationships tend to form naturally — but to some extent it is a marketing funnel. What you're marketing is yourself and your vision for the type of company you want to build, and what you're selling is the opportunity to build that company together.
It's so critical for founders to "start with why" at this stage and clarify their own vision, expectations, and goals early on. I'd encourage founders to write this down (ideally in public) since this will help you articulate your answers to these foundational questions as clearly and succinctly as possible. If you write publicly about your vision, you'll be able to scale yourself so much better than you could ever hope to do on your own.
As you speak with potential co-founders, customers, advisors, investors, and future employees, you'll find it invaluable to have taken the time up front to articulate your views on these keys questions (more on this below).
So what can you do to increase awareness and attract awesome potential co-founders? Here are a few ideas that've worked well for me:
- Reach out to your existing network; LinkedIn, former colleagues, existing advisors, etc. Let them know what you're looking to build and the type of people you're looking to work with.
- Join related communities — the more niche the better — and engage with people. Niche communities are self-selecting in that they do a lot of the hard work for you by attracting people who're already proactively interested in your space. Try to spark conversations with these folks, share what you find genuinely interesting, and see where those conversations lead.
- Explore accelerator, incubator, and startup programs that are focused on helping early stage founders. Some examples include On Deck, Write of Passage, and other niche cohort-based courses.
Open up your DMs and prep your calendars. You're going to be having lots of meetings...
I believe this is the single most important phase that many co-founders skip past too quickly.
The main goal of this phase is to get a feel for each other and to ensure that you're aligned on what I refer to as hard constraints.
A hard constraint is a factor which is a must-have for you to work together. Soft constraints, on the other hand, are factors which are nice-to-have but not necessarily deal breakers. Identifying your hard constraints up front will make the co-founder dating process much more efficient and enjoyable.
For example, here's a breakdown of my personal hard constraints:
I personally only want to partner with co-founders who have a strong intrinsic motivation to work on the same problem, space, and target audience.
This is because many of the best co-founders tend to be convergent; e.g., they're independently working on similar problems and end up joining forces along the way.
Questions to ask:
- What are this person's motivations & goals?
- Are they opportunistic or do they have a clear view of what they care about?
- Are this person's values compatible with mine?
- Does this person have founder-market fit?
I want to build a high impact company that may raise some initial capital, but I also want to be conscious about not jumping on the VC hype train. My ideal company in 5 years would have millions of customers while remaining extremely lean ala Sahil Lavingia's approach with Gumroad.
- E.g., I'd rather be surrounded by 10 world-class generalists than have 200 employees. The people I want to help monetize on the supply-side of the passion economy could potentially be viewed as lightweight consultants, but they wouldn't necessarily be my coworkers.
Questions to ask:
- How much equity are you both expecting? (talk about this up front and set some basic expectations like a minimum %)
- Are you looking to raise VC or bootstrap? What's your timeline? Do you want to continue raising on the VC rocket-ship or grow more sustainably?
- What are your expectations on full-time vs part-time?
- Are you open to joining an accelerator / incubator?
- What type of company do you want to build in 5 years?
For co-founders, I value working with extremely flexible generalists over people who are only capable of specializing in one area.
Questions to ask:
- Are they capable of wearing many hats?
- Do they get shit done?
- Are they proactive?
- How are their communication skills?
Questions to ask:
- Do I feel like this person is a peer and someone who will make me a better version of myself? Or do I feel like this person would make a great employee?
- Would this person make a better angel vs advisor vs co-founder vs colleague / supporter?
- Does this person have a solid understanding of how the game works?
- E.g., I believe it's important to be on a similar page in terms of your understanding of world-view and industry-view. I prefer working with people who understand the bigger picture of how the startup world operates w.r.t. things like the VC ponzi scheme and that the only validation that matters is from your customers.
- Fwiw, a younger version of myself would've whole-heartedly failed this test, which is why it's important to consider where potential partners are at in their career and personal development.
I need to trust this person to have my back no matter what, and for me it's essential that I could see us chilling outside of work because they're a genuine person who I can learn from and vibe with. 🤙
Questions to ask:
- Would I be excited to hang out with this person outside of work?
- Does this person have an ego?
- Is this person genuinely interested in getting to know me? Or am I just another meeting on their calendar?
- I've met with dozens of people who have given me various degrees of bad vibes. Maybe they were just not very engaged. Maybe I got the feeling they were probing me for information. Or maybe they liked to hear themselves talk just a little too much.
- My advice is to be open & engaging by default, but keep an eye out for frenemies and potential competitors. Unfortunately, the promise of getting rich quick via startups does attract a subset of people with questionable morals. Don't get brain raped.
- If you get asked to sign an NDA during the co-founder dating process, I would view this as a strong red flag. Advisors, angels, and investors almost never agree to sign NDAs (which can only potentially hurt you) without having some type of compensation in exchange (most of the time via equity). There are very rare exceptions to this rule mostly related to hard sciences and patentable IP.
- Can I see myself trusting this person with a large investment?
- Most importantly, do you get good vibes when hanging out with this person?
My soft constraints that are nice-to-have but not necessarily deal-breakers include:
- complementary skillsets
- good background on paper
- solid network
- access to funding
- geographical location
You might have a different set of hard constraints, but I'd encourage you not to deviate too far from these broad strokes. Another common hard constraint that you'll see is co-founders looking for complementary skillsets, which is totally reasonable. It's just less applicable in my case as a technical founder.
The most important thing you should be looking for in these initial meetings is figuring out whether or not potential partners align with your particular set of hard constraints. Write your hard constraints down ahead of time. Take notes in these meetings. Stick to your hard constraints. And don't be afraid to follow-up with background research on people.
Joining hands as co-founders is an important decision. You could totally end up getting lucky by meeting the right person and doing none of these things — but I'm a firm believer in making my own luck.
One concrete piece of advice that'll really help you stand out in intro meetings is to put together and share some initial thoughts & research ahead of time, especially for connections that you're really excited about.
For example, one of my senpais, Li Jin, introduced me to a pair of non-technical co-founders awhile back who had solid traction, had already raised a pre-seed round, had great backgrounds, and most importantly were working on a platform directly related to my core mission.
So before my first meeting with them, I put together a one-page Notion doc and shared it with them. The doc gave my honest feedback on their current product, my concerns, and then focused on a series of key questions that I wanted to dig into during our meeting.
This approach has a few really amazing advantages:
- You immediately stand out from any other networking meetings they’re having.
- You set the tone up front that you know what you're talking about, that you care about this space, and that you value their time.
- You end up having a much more productive conversation that's focused on the key areas that you want to flesh out instead of doing the whole awkward intro thing.
This isn't always possible, of course, especially with people who don't have much of an online presence, but imho it's generally a bad sign for startup founders to not already be digitally native.
At some point during the consideration phase, probably after a number of meetings and some async back & forth, you'll want to start working on something concrete together.
The main goal of this phase is to get a feel for how well you work together in practice, what your respective roles might end up being, and whether you like spending time with this person.
I recommend scoping out a few time-boxed project ideas. They shouldn't be at the scale of building your startup MVP, but rather something isolated and fun that you can launch quickly.
Some ideas include:
- Doing market research together and analyzing the results.
- Writing an in-depth blog post or mission statement together.
- Launching a lightweight, no-code website or resource aimed at your target audience.
- Executing on some aspect of a potential MVP, whether it be speccing out user flows, creating some wireframes, or jumping into some code.
Things to look out for at this point in the process:
- Is this person proactive or are you leading the way?
- How do you handle disagreements & compromise?
- Can you communicate effectively together?
- How does your work cadence & expectations compare with theirs?
- How do they handle themselves professionally?
- Would you feel comfortable having this person run important meetings as a stand-in for yourself?
- Are you a better version of yourself when you're working with them?
- Would you be excited to hang out with this person outside of work?
The final stage of the co-founder dating process is actually joining together as partners. This is where the real work begins... 💪
Whether your partnership starts with a handshake agreement, or with an application to an accelerator like YC, or with incorporating and officially splitting equity, you're making a commitment towards building a company together. Hopefully that's a commitment that you feel strong enough about to potentially spend the next 5-10 years of your life working towards.
Many people compare founder relationships to marriage. That's a bit of a hyperbole, but it's not too far off. Some of my closest friends in the world are my former co-founders, and I think part of the reason why I'm so close with these folks is because we've worked through some really, really difficult times together. It's a bonding experience that you won't soon forget. Starting a high growth company with someone is guaranteed to be a roller coaster ride where the highs are incredibly high and the lows are incredibly, devastatingly low. But at the same time, you won't change the world without taking risks...
So before making your relationship official and having this person join your journey, ask yourself this: are you confident that you can trust them to have your back when nobody else does?
... :crickets: ...
Ultimately, I don't think you can answer this question for sure without taking a leap of faith and making a go of things together. No matter what happens, though, you're guaranteed to learn a lot about each other — and even more about yourself — along the way.
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Update: Also see our 40-minute interview on this topic. Picking a co-founder is your most important decision. It's more important than your product, market, and investors. The ideal founding team is two people, with a history of working together, of similar age and financial standing, with mutual respect.