The biggest risk in your portfolio may be two people who stopped talking.
You can diligence the market, the product and the numbers. The founding relationship is harder to see until it breaks. I help investors see it earlier and give founders somewhere to take it.
You refer. The founders own the work.
Refer a pair, quietly
When you sense strain between cofounders, send them my way. Founders often hear "get a coach" from a board member as a verdict. I make it a conversation instead, and you only hear what they choose to share.
Give your portfolio a resource
Put me on your platform team's list for founding teams who want to stay strong through a raise, a pivot or rapid hiring. Some firms fund this from a founder-development budget.
Run a portfolio cohort
Zero Zero Guild can run a private cohort for your portfolio's cofounder pairs, led by me and Arthur Levitan. Pairs learn from each other, and your firm becomes the one that helped.
Seven questions that show you how a founding pair will hold up.
Ask the first three with both founders in the room. Ask the rest separately, in the same words. The gap between their private answers is the most useful thing you'll collect.
Across all of them, notice whether each founder says “we” or “I.”
1. How did you two start working together, and how long have you known each other?
Follow up with the hardest thing they've been through together. Listen for how they got through it, and whether there's warmth in the telling.
2. Tell me about the last real disagreement you had. Did it get resolved, and how?
Watch the founder who isn't talking. Can each one state the other's point? Any trace of contempt is the strongest warning sign there is.
3. Can you name a dynamic tension between the two of you?
The best answer is that it both helps and gets in the way. It's a bad sign if one founder describes the other's side as the problem.
4. Who does what, and have you written any of it down?
“We don't need it, we trust each other” usually means friendship is standing in for structure they've been avoiding.
5. When you can't agree, who makes the final call, and on what?
Compare their answers with the fight they described in question two. A rule that exists only on paper isn't a rule.
6. How did you decide on equity and titles, and would either of you do it differently now?
Hesitation is data. A split that was settled fast and never revisited is often a conversation that closed too early.
7. What conversation have you two been meaning to have and haven't?
Fast, matching answers are a strong sign. Different answers show you where the first real fight will be. “None” is a flag.
Send the diagnostic to a founding pair.
It's a low-pressure way to raise the subject. Each founder answers on their own, and only they see the results unless they decide to book a debrief.
The strong pair
Proceed. These pairs take to coaching quickly and benefit from it.
The dangerous pair
They look fine together and tell two different stories in private.
The coachable pair
They agree on the facts and are hard on each other. These pairs often gain the most.
Two different companies
The founding team is the main risk in the deal.