Finding a cofounder: like business dating

Similar to personal life, entrepreneurship involves figuring out what your priorities are, meeting people to see if there might be a good professional fit, discussing your goals and values, and making a call if it’s worth moving forward or not. It’s also a bit awkward, just like in your personal life.

I wasn’t sure what I wanted when I first began my entrepreneurship journey. Did I want to go it alone or find a cofounder? There are pluses and minuses to either approach, and I didn’t have an immediate bias one way or the other. I talked to lots of friends about starting something, didn’t have any immediate hits of timing / interest, and started talking to friends of friends. I guess this was like business blind dating. I went in with an open mind and had lots of coffee chats.

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Key Conversations with Potential Cofounders

A few things I kept in mind were my personal mile markers from last week’s post. Potential cofounders and I discussed this same sets of topics. Aside from the usual background / resume items, here are questions we discussed:

Topic: Income realities (can I live without income for a while?)

Sample questions:

• Where are you professionally right now? 
  • Are you employed, recently laid off, or somewhere in between? 
  • Understanding each other's income realities is essential
• Are you applying for jobs right now? 
  • If so, what’s the timing for applications in the works? 
  • How serious are you about taking a job vs. pursuing a business?
• How long are you comfortable without an income? 
  • This doesn’t have to be “how much $ do you have saved up”
  • You’re trying to understand if you each have a timeline in mind when you need to see a positive signal in order to keep going.
• How are you going to manage benefits, like health insurance?
  • Is it covered by a spouse? Buying out of pocket? Something else?
  • These add up, so what’s the plan? This factors into how long you can go without income. 
• Are you willing to make major lifestyle changes (ex: downsizing, moving, etc.)?
  • If the answer is yes, maybe you have more time
  • If the answer is no, that’s fine. It just tells you both parties kind of know their personal expense run rate and assume that needs to continue going forward
• Are you willing and able to invest your own money in the business?
  • If the answer is no, this might mean you need to raise money
  • If the answer is yes, you may be capable of bootstrapping
  • You don’t have to decide here, but do discuss what happens if you need to invest in people or other expenses for the business

Topic: Why you’re interested in building something

Sample questions:

• Why do you want to build something?
  • Obvious! But double click into the answer
  • For example, “build something real” you’d want to know why. Is it because you’ve been in jobs where your work was very rarely released? You want to make a positive impact on a mission you’re interested in? This one is mainly about the follow up questions.
• What kind of hours / lifestyle are you aiming for?
  • As a mid-career professional, you may or may not be up for 100 hour work weeks. You may want the flexibility to visit aging parents or attend to school pickups. Or you might be excited to work those 100 hour weeks.
  • No judgment, but have that conversation. 
• Are there particular industries you really want to serve (or not serve)
  • This could be general interest (ex: fintech seems interesting) 
  • This could also be industries you’d like to avoid (ex: retail requires lots of $ for inventory, I’d like to avoid)
• What would you want your business to be when it grows up?
  • Are you trying to build space internet (big hard problems) and the next $100B company (big goals), or are you coveting the small profitable business your friend built?
  • You're trying to get a sense of what "success" looks like to your potential cofounder

My strengths and gaps

Sample questions:

• What do you think your biggest strengths are? 
  • This isn’t just what’s on your resume, it’s more like superpowers. Are you highly creative? Have an amazing network? Shockingly good at cold outreach? Great at finding market niches?
  • The goal here is to understand more depth of what you could each bring to a business
• What are the gaps you have?
  • No judgment here, it’s really just your own self assessment 
  • You’re really looking for complementary skill sets. I was definitely not looking for a second me, that's too much.
• How capable are you of getting your hands dirty these days?
  • If it’s been a while since you’ve written code or had to build your own business model / strategic plan, how willing / able are you to revive those skills?
  • This helps understand preferences. We are all likely rusty at many things that used to be core competencies (you should see my lack of Excel shortcuts these days), but if you’re willing to get your hands dirty, you can certainly be useful.
  • It does not mean you / possible cofounder need to do everything or be willing to get your hands dirty. If you’re not, it just means you’d need to plan to hire for missing skills.

Next Steps

This is a good start at seeing if you could be aligned on values. You may not be, and that’s ok. You can keep up the coffee chats, keep testing your ideas with the market, keep prototyping. There are plenty of successful solo entrepreneurs or solo founders.

If it seems like you are generally aligned on values, great! There are a bunch of steps after that. I’ll outline a few in upcoming posts, such as 

• Finally having the bootstrap vs. raise money conversation
• Agreeing on a few starter ideas to pursue
• Discussing economics, like how you would split the business, roles, responsibilities, and titles
• Standing up an appropriate legal structure

You definitely don’t want to rush into anything and want to spend some time understanding your potential cofounder better. Building a business is kind of like an arranged marriage, where you are agreeing to move forward together for better or worse. As in life, you’re best served taking your time and making sure you’re both on the same page about important things. Taking your time to align on values and goals is critical, but don’t forget to enjoy the process. Finding the right cofounder can be the beginning of the next phase in your entrepreneurial journey.

Spoiler: I did end up with a cofounder.