Discover more from The O’Daily by Kathryn O'Day
Looking for a Co-Founder? 4 Strategies To Help
You know what’s harder than finding a needle in a haystack?
Finding a dang co-founder!
You know you want one — whether for technical help, sales help, sanity checks, or simply moral support when you’re doing the really hard thing of starting a company.
The magical, ideal co-founder is someone:
you’ve worked with before (bonus: started a previous company with them!)
who balances your strengths and weaknesses (professionally & personality-wise)
you want to see every day for the next 10 years
who will help you weather the ups and downs
Easy peasy 😂
If you’ve already found this person, congratulations!!!! (And pass this article to someone still on the hunt.)
If you’re still looking for “The (Co-Founder) One,” my best advice is to date before you marry!!!!!!!
(Note: actual romantic dating of your co-founder is not recommended! 😂 It’s a metaphor, people!!!!)
It’s possible to unwind a mistake but it’s often expensive, stressful, and time intensive.
All things you don’t want on top of the already expensive, stressful, and time intensive experience of building a company!
Here are 4 ways to de-risk that whole co-founder thang and find your next startup partner!
1. Check References
Hopefully this goes without saying but — for the love of everything — ask around.
Check official references! Talk to unofficial references!
What do previous co-workers, employees, investors, or co-founders say about this person?
What are their quirks, when do they shine, and what stresses them out?
I’d expect to hear 95-99% rave reviews.
If there’s any red flags, get out now!
Those bridges they burned? They’ll light yours on fire too!
2. Contract Engagement
💕Engagement.💕 Ha! I’m hilarious.
But seriously. If you find someone with tons of potential, see if they’d be interested in a 1-3 month consulting gig.
It’s a great way for both parties to understand strengths, weaknesses, goals, working style, and overall compatibility.
Make sure you talk about any concerns or feedback along the way.
This is important because:
EVERY RELATIONSHIP TAKES WORK. Even with the most perfect co-founder, you’ll disagree, get annoyed, and have conflict. You have to be willing and prepared to work through things. Begin as you mean to go on!
You want to see how they communicate and respond — with language, action, and change (or not). Startups are hard. What does someone do in the face of conflict or hardship? Better to know now than later!
See how your conflict and resolution styles work together. It’s not just about how someone reacts to conflict and feedback, it’s also about conflict compatibility. If you both like heated discussions, great! If one of you does but the other would prefer a calm debate, this could be a big sticking point down the road.
If you don’t know after 3 months, it’s probably a no.
If you’re really not sure after 3 months, pinpoint exactly what your open questions are and figure out a way to vet those items specifically and quickly.
3. Start With A Different Role
Not everyone has interest in or the life circumstances that allow a contract engagement.
If you think someone has potential as a co-founder or they express interest in being a co-founder but you want to de-risk it, start them in a specific leadership position.
For example, bring someone on as a CTO or Head of Sales to start.
You can always promote them to co-founder later. (It’s quite common to add a co-founder months or years after the company started.)
This works for any C-level position as well as co-founder.
If you think someone has potential but they’re a little green, give them a general or less senior title to start (e.g. “Head of” or <area of focus> “Lead”).
Explain that titles and responsibilities will grow and evolve as the company does. Then you can promote them or share feedback on what they need to improve.
When I joined Rigor, I was interested in being COO eventually, but I knew the immediate need was in Customer Success. So I started as Director of Customer Success and did a lot of general company organizing and managing along the way. A year later I was promoted to COO. It was a natural transition that the CEO and I both felt good about.
4. One Year Vesting Cliff
This is a fancy stock term.
Here’s what it means:
They get nothing if they leave or get fired before the 1 year mark.
Note: make sure you have a lawyer (or ChatGPT 😂) to get the wording and details right! The O’Daily is not legal advice.
It’s a very, very standard term for startup stock agreements.
It’s LITERALLY been in every startup stock agreement I’ve ever seen from a reputable startup.
If someone pushes back on it, it’s rather suspect.
If someone wants to vest right away or is not planning to be with the company for more than a year (when hired for full time role)…there’s a significant misalignment somewhere!
If someone is with your company for over a year and then things go south, presumably they’ve added enough value to deserve 25% (of a 4 year total vesting timeline, another common vesting term) of their allotted stock/options.
If they didn’t add enough value to earn that, it’s on you as the founder for not moving them along sooner. (But not on Day 364 — bad look. You’ll know way before then. Rip the bandaid off as soon as you know. There’s never a good time and waiting doesn’t make it easier.)
Finding the right co-founder can be one of the most important things you do!
It doesn’t happen overnight.
Give yourself time and some safeguards to make sure it’s a great long term partnership.
What other strategies have you used to find, vet, or “date-before-you-marry” your co-founder?