How Not to Find a Co-founder

Today’s guest writer is Heather Bowden. Heather was comfortable running her biotechnology company until she discovered her passion for copywriting. Next, she expects to complete an MBA in Sustainable Business and work toward her dream of being a guest on the James Altucher podcast. Her blog broadcasts her learnings about success, happiness, entrepreneurship, and relationships. @msheatherbowden

When I started my first business, I tried interns and consultants with no luck. In biology, if something gets contaminated by mold or bacteria, you lose at least 2 months. Let’s just say I lost 4 months. So, I never had full-time people, much less a cofounder. And after 4 years, it was time to close the business.

For round 2, I was going to do things “right. I spent 6 months nursing the 4 Hour Work Week and the Lean Startup, but nothing clicked. I was impatient; I just wanted to get started. The cofounder hunt reminded me of dating, an enormous time suck. But I wanted to share. I wanted to split. I wanted to support. I really wanted a cofounder. I was convinced it was best for a business and me.

I got a lot of the same advice over and over again. A cofounding relationship is like a marriage. Be willing to work with the cofounder for 10 years. Choose someone whose skills are complimentary to yours, and look for a whole lot of chemistry. Chemistry is key. You also have to like the person. Do test projects or sprints with the cofounder. Vest the cofounder. Don’t split equity 50/50 or investors will run away. You need a tie-breaker. Someone should be the obvious decision-maker. Consult a lawyer as soon as equity comes up. Y Combinator, the #1 startup accelerator, specifically asks what hackathons or competitions you have done together. As a general rule, the faster the vetting process, the more time invested.

What I learned during the cofounder hunt: How Not to Find a Cofounder

What worked: doing a hackathon together, whiteboarding together, informational interviews.

What didn’t work: 3-week project sprints.

Example of a 3-Week Sprint:

The Purpose of this exercise is to mutually determine if we would want to work together for the next ten years. 3 ideas shared at 5pm on Friday. Keep track of time and do not exceed 15 hours. It is important that we assess our current states of efficiency.

This project will run over 3 weeks. We can discontinue at any time.

Week 1: Ideation. Are our work styles compatible? Are we committed (to at least the first week)? Do we do what we say we will do?

Week 2: Collaborative Project with digital communication. How well do we communicate? How well do we telework?

Week 3a: Whiteboarding Idea. Do we have chemistry? Do we inspire each another? Do we participate as equals in the conference room?

Week 3b: Evaluate. Are we capable of making decisions together? Are we still excited about working together?

A couple of guidelines for ideas:

1) Solve a problem/frustration, create joy, or some sustainability component (like repurposes waste). All 3 ideas could solve the same problem.

2) Scalable.

In the 3rd week, I requested a candid conversation about where we are at and whether or not we want to keep going. These conversations were so mentally exhausting that I wanted to nap after. But as an entrepreneur, I couldn’t. Push yourself to keep going, especially when you want to nap. Willpower is a muscle. Build it.

What I learned:

Informational Interviews. At first, I treated our first conversation like a typical job interview. I would meet someone, make immediate assumptions, and then spend the rest of the time confirming whether or not I was right. Then I tried a casual coffee date. We walked away feeling great, but learned very little. For the fourth potential cofounder, I listened to a dozen business podcasts to learn how to ask probing questions. This made a huge difference. We had a 2-way informational interview. It didn’t work out for us as cofounders because she realized she wanted to be CEO instead of CTO. But everything else was there, even after 2 weeks of working together.

Hackathons and Competitions. I did Protohack, a non-technical hackathon, with a potential CTO. We formed a team with 4 others and spent 12 hours designing an app. This was an exercise in longevity. It also answered almost everything I wanted to learn with 3-week sprints.

Listen to your gut. Every legendary entrepreneur cultivated a gut they could trust. First, distinguish whether your gut is just your survival instinct protecting you from failure, success, or risk, or that it is telling you something that matters. Discovering your gut saves you tons of time (spoiler: also builds confidence). If your gut says, this person says they want to be a CTO, but they really want CEO, listen. If your gut says, this person isn’t ready to share, listen. If your gut says, this person has too much baggage or is too jaded to work with, listen. If your gut says, this person is doing too many different things and they are not willing to choose, listen.

Delegate. I asked my friends & family for money, only to realize that they were as broke as I was. Out of that failure, I discovered that they wanted to contribute their skills and drive instead. My friend wanted to become an event planner, so I gave her the opportunity to try it out. My other friend was an admin and looking for more enriching work. She welcomed the opportunity. My brother loved spreadsheets, so I asked him to put together a few databases of potential customers. My mom was an empty-nest housewife. She browsed the internet every day for about 12 hours. I asked her to research self-publishing instead and had a report the next day. Incidentally, delegation satisfied my desire to share, split, and support. I’d still like a cofounder, but this did take a weight off.

Outsource. While you are looking for a cofounder, don’t delay on getting customers (like I did). Outsource anything that friends & family can’t do. Only outsource when you have enough customers to justify the expense (post-MVP). Outsourcing is great in the beginning, before you have to rapidly scale. But as your business grows, make sure you know what everyone is doing and why. It will help you maintain your vision. But I digress. Outsource.

Ultimately, I learned that a passive approach works better for me. I still want a cofounder, but I’m not willing to devote 2–4 hours a week looking for one and 8–15 hours a week vetting one. At Protohack, a startup called Bliss presented on what to do when you’re looking for a CTO. They suggested we hire someone and vest them into the cofounder role. I really like that idea, and will try that next.

Call-Out’s

“The cofounder hunt reminded me of dating, an enormous time suck.”

“…learn how to ask probing questions”

“Discovering your gut saves you tons of time”

“…don’t delay on getting customers…”

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