One of the most important decisions you make in start-up life is whether you’ll go it alone or with a co-founder. Neither is inherently better. Some founders need to have the freedom to make every decision, and others want to be part of a team to have more security or subject-matter expertise.
But what if you want someone to take the journey with you but don’t know where to look or how to vet candidates once you find them? Here are my tips, as a serial entrepreneur who launched a business solo and then found my ideal co-founder.
What qualities do you want your co-founder to have? There are some universal answers—resilience, intelligence, kindness—but the right person is also going to complement you. Understanding what gaps you need to fill in your organization means taking a hard look at your skillset. Ask yourself, “What do I do incredibly well?” If you’re creating a start-up (or even thinking about it) this list is probably extensive, so don’t short-change yourself. If you’re having trouble, think, “What do other people think is work that feels more like play to me?”
Then, be equally honest on the flip side. What are you not-so-great at that your business will need (even on the most basic level) to succeed? Yes, you can eventually hire someone to excel in areas where you don’t shine. But you can’t hire until you reach one of two achievements: profitability or outside funding. Think in terms of what (and therefore, who) your business will need to get to either marker of success.
Look to Your Network
Sure, you can post on job boards and outbound folks on LinkedIn. The truth is that a co-founder relationship is such an intimate, intense arrangement that people are unlikely to volunteer unless you (and your company) come with the seal of approval from someone they know. That’s why community groups are so crucial for entrepreneurs, whether they’re accelerators or resource groups, they’re an opportunity for you to get support and to tell the world about what you’re building.
What exactly do you ask your network? They don’t need to know every detail. Just tell them the areas you’re looking to solve for in your business. I originally thought I was looking for help with operations, and told my network that I’d like to work with a consultant. I met my co-founders, Monika, through a mutual friend; she would never have responded to a “co-founder” ask but was very happy to help me think through some problems. It was only after we’d been working together for a while that the inherent fit occurred to both of us.
In the “before times,” prevailing wisdom was that you absolutely needed to meet in person so that you could see if you “gelled.” It’s clear now that that’s not entirely true. One reason I knew Monika and I were a good fit was that we were able to communicate well even with the barriers of an entirely virtual relationship.
Assess Start-Up Fit
Start-up life isn’t for everyone. There’s the obvious financial risk, but the element people often overlook is the lack of predictability. You can be firing on all cylinders and making great progress on your product, and then you learn a piece of crucial information that means that you’ll need to set it all down and start walking in the opposite direction. You’ll need a co-founder who is dedicated to the underlying “What” of your start-up, and can be super-flexible about the “how.”
How do you assess this? Ask open questions. A lot of them. And remember, the best open questions start with “what,” because they’re much less likely to accidentally “lead” the person you’re talking to. Try: “What’s important to you about our mission?” or “What would your reaction be if we had to scrap this part and start over?” And then really listen. This is one part that’s actually a little easier over Zoom; it’s easier to force yourself to leave space for the other person to answer when there’s an actual Mute button.
Make an “If-Then” Plan
So you’ve asked the people you trust, they’ve helped you meet someone, you’ve asked all the open questions: What now? Make two plans: One for if it all goes magically, and one for if, three months from now, you’re no longer speaking.
Open communication is the cornerstone of all relationships, and co-founder partnerships are no different. You need to be able to openly discuss your end goals: are we building this to sell in 5 years, or are we aiming for an IPO? Will we take venture money? Who should be on our board? See if you can navigate these conversations (and if you like their answers) before you even think about signing paperwork.
And, of course, we always wish for the best, but some relationships just won’t work out in the long term. If the person you’re considering reacts poorly to discussions of vesting cliffs and a contingency plan, run (don’t walk) in the other direction. They should be equally invested in knowing exactly what their rights and options are in any scenario.
It helps to know the steps of bringing a co-founder on board; who should you ask and how should you approach the first conversations. But the underlying truth is that it’s also largely a gut decision. Once you’ve checked all your boxes and talked through all the tough stuff, you need to check for that final piece: The energy the person gives you. I knew Monika was “The One” because I got off every call with her feeling buzzy creative energy. She made me an even better version of myself as a founder, and I knew she’d have the same effect on Small Packages.
“Understanding what gaps you need to fill in your organization means taking a hard look at your skillset.”
-Julie Schechter, CEO and Co-Founder of Small Packages
About the author: Julie Schechter is a Harvard Law graduate, TechStars 2021 alum, serial entrepreneur, and award-winning CEO and co-founder of Small Packages, an e-commerce platform and curated care package company offering an easy way to share the love, perfect for any occasion or just because, in the time it takes to brew a cup of coffee. Julie and her co-founder Monika Shah recently became TechStars 2021 recipients for their innovations with Present, a virtual personal relationship assistant that helps you stay in touch, send gifts, and ensures you’ll never miss a loved one’s important dates again.
Featured image by Color Joy Stock.