43% of Founders Are Forced to Buy Out Their Co-Founder. Here's What They Skipped.
The one conversation most co-founding teams keep avoiding and a 90-minute exercise to have it this week.
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This issue was inspired by my recent conversation with Mona Jawad and Ayesha Kazi, co-founders of ASL Aspire, a gamified STEM platform for deaf students. If you haven’t listened to that episode yet, it’s worth your time.
One question before you read this
What’s one conversation you’ve been avoiding with your co-founder?
You don’t need the full story. Just the headline. Hold it in mind as you read.
What this issue is about
The co-founder relationship is the one thing most founding teams leave completely undesigned.
You’ll obsess over your product roadmap, your hiring process, your pitch deck. But the hard conversations about roles, about money, about whether you’re still on the same path, these keep getting pushed to after this launch, after this raise, after things settle down.
They rarely do.
In this issue:
Why the co-founder relationship deserves the same deliberate design you bring to your product
A real story from two founders building something meant to last 10–20 years — and how they think about this
A 90-minute 1–3–5 Life & Startup Check-In you can run this week
Questions to catch misalignment before it becomes resentment or a surprise exit
What it actually looks like (and why it’s easy to miss)
I recently sat down with Mona Jawad and Ayesha Kazi, co-founders of ASL Aspire, a gamified STEM platform for deaf students. They met through the Undeclared Engineering program at University of Illinois during COVID, bonded over a “really horrific electrical engineering course,” and ended up building a company they intend to run for the next decade or two.
They’re also best friends, which makes the co-founder relationship both easier and more complicated.
Here’s how Mona described it: “She’s my friend, but she’s also the person I need to fill out tax forms with. She’s someone who I love playing Nintendo Switch with, but she’s also the person who I need to go nag about an email.”
What struck me in our conversation wasn’t the tension, it was how deliberately they’d learned to name it. A few things they shared:
On the fear of a co-founder leaving: Ayesha was direct about this: “You never want a co-founder to up and leave. Everybody has autonomy to get up and leave and it’s really scary to think that could happen.” Their response wasn’t to avoid the subject, but it was to build enough trust that the conversation could happen early. “If I’m applying to grad school, Mona knows. If I want to get a full-time job, Mona knows. We have that kind of communication set up.”
On the money conversation: “In the beginning, it was really hard for us to talk about it. We had a lot of tough conversations where no one was speaking and we were just really trying to put something on the document of like, “where’s our life going?” Because we didn’t know where our life was going.” Ayesha didn’t dress it up: “I still need to pay rent. Say you have projections to be successful in X amount of years, we don’t know if that’s actually going to happen.”
On throwing yourself into work when life gets hard: Mona identified a pattern in herself: “When we get stressed by externals, sometimes we try to throw ourselves into the work to deal with that, maybe I can just make some progress in one part of my life, even if everything else is on fire. And often what that leads to is subpar work in both domains and burnout.” Ayesha has gotten good at catching it. And Mona tries to reciprocate.
On the 1–3–5 check-in: This one stopped me. Without any prompting about frameworks or exercises, Ayesha described what they actually do: “Once or twice a year, just like regrouping and being like, what’s our one year, three year and five year plan for our lives, not about our company. That includes relationships, where we’re living, sustainability and keeping the lights on at home. Where does ASL Aspire fit in our lives?”
That’s it. That’s the whole thing. And they’ve been doing it since the beginning, not because someone told them to, but because they learned the hard way that the alternative is having people “up and leave” without warning.
None of this required a perfectly designed relationship from day one. It required a willingness to keep having open conversations, even when it was uncomfortable, especially then.
If this made you think of your co-founder, send it to them and propose running the 90-minute check-in together. Compare what you’d each add to the agenda, that conversation alone is worth having.
What the research actually shows
Two things from the research worth knowing.
Co-founders often aren’t having the same conversation, even when it sounds like they are. Research on founding team formation (Gray, Howell & Sackett, Organization Science, 2024) found that when two people are deciding whether to build something together, they’re typically evaluating entirely different things without realizing it. One person is thinking about skills and resources: can this person do what we need? The other is thinking about the relationship: can I trust this person over the long haul? Neither says this out loud. So the team forms believing they’re aligned, and they’ve never actually been in the same conversation.
That gap doesn’t close on its own. Founding teams are building trust and a working relationship at the exact same moment they’re under maximum pressure, which makes explicit conversation not just useful, but structurally necessary. The same researchers found that up to 43% of founders are ultimately forced to buy out their co-founder due to interpersonal rifts and power struggles, not because the idea was wrong or the market wasn’t there, but because the relationship underneath the company was never explicitly designed.
Recovery and detachment aren't optional. Longitudinal research on psychological detachment from work (Baktash & Pütz, Journal of Happiness Studies, 2025) found that mentally switching off from work during off-hours is a key driver of well-being, across emotional responses, job satisfaction, and life satisfaction. For founders, this is counterintuitive: the instinct is to equate constant presence with progress. But a nervous system that never recovers makes conflict feel more personal, erodes patience with your co-founder, and quietly degrades the quality of every decision you make together. (I went deeper on this in Rest Isn’t a Nice to Have, It’s a Distinct Advantage.)
The inner game in three lines
Most founding teams treat the co-founder relationship like infrastructure, ignored until something breaks.
The shift is to design the relationship like a product: explicit roles, honest horizons, and built-in repair.
The exercise below is how you start.
If you want a complementary lens on running small, low-risk experiments inside your company, the Why Your Biggest Moves Stay Stuck in Drafts issue is worth a read alongside this one.)
The 90-Minute Co-Founder 1–3–5 Life & Startup Check-In
Format: 90 minutes | In-person or video | One shared doc, personal notes for each
Goal: Make explicit (a) where each of your lives are actually going in 1, 3, and 5 years; (b) how the company fits into that honestly; and (c) what that means for roles, trust, and operating rhythms right now.
Step 1: Set the frame (10 minutes)
Answer together:
“Why are we doing this now?”
“What do we hope feels clearer by the end of 90 minutes?”
Write down ground rules:
“We’re here to understand, not to convince.”
“We can disagree on paths and still respect each other’s constraints.”
“We’re allowed to pause if something gets heated.”
Step 2: Share your 1–3–5 Life Maps (30 minutes | 15 each)
Each founder takes 5–7 minutes to jot notes privately, then 8–10 minutes to share while the other listens without problem-solving.
Prompts for 1, 3, and 5 years from now:
Where do I ideally live?
What does my work week look like: hours, travel, focus?
What do I need financially to feel “okay” vs. “good”?
What relationships or family realities shape my time and energy?
What do I want to be building toward personally: skills, identity, reputation?
The listener’s only job: Ask clarifying questions (”Can you say more about that?”) and reflect back what you heard (”It sounds like in three years, X matters most and you’re worried Y will get in the way”). No advice or solutions yet.
Step 3: Map the company against your lives (20 minutes)
Now ask: If our lives actually look like this in three years, what does that imply about:
Our roles in the company
How long each of us can afford to be underpaid and what “afford” actually means
Whether full-time vs. advisory roles make sense at different stages
How we think about equity, titles, and transitions
Capture tensions explicitly rather than softening them:
“I want to be in City A in three years, and most of our key relationships are in City B.”
“I’d want to take a real break around year five, what would have to be true for that to work?”
You’re not solving everything. You’re making constraints visible so they stop operating underground.
Step 4: Clarify ownership and trust (20 minutes)
Each of you privately completes these, then share:
“In the next 12 months, I will own…” (3–5 concrete areas: enterprise sales, product vision, fundraising, hiring, etc.)
“I need you to own…” (3–5 areas where you want to fully trust the other to lead)
“I feel most supported when you…” (specific behaviors: “tell me early when you’re overloaded,” “push back on my optimism when the data doesn’t support it,” “flag it when you see me spinning”)
Then ask each other:
Where do our ownership lists overlap in ways that could create friction?
What’s one decision type where we’ve agreed you make the call, even if I’d weigh it differently?
Agree on 3–5 specific trust behaviors, written down:
“We’ll name it within 24 hours if we’re quietly resentful about something.”
“We won’t surprise each other with major life decisions: job opportunity, move, grad school, even if it’s just a maybe.”
Step 5: Set rhythms and red flags (10 minutes)
Rhythms to commit to:
A monthly 45-minute non-work conversation about life, not metrics
A twice-yearly 1–3–5 check-in like this one
Weekly check up for 15-30 minutes to sync
Red flags to name:
“What are two or three early signs we’re drifting?” (One founder stops sharing concerns; you cancel all non-urgent check-ins; you only talk in Slack)
“What’s the protocol when we see a red flag?” (Example: “We schedule a 30-minute repair conversation within 72 hours.”)
Step 6: Pick one experiment for the next 7 days (10 minutes)
End with a single behavior to test this week:
A shared “energy check” at the start of your main meeting
A standing agreement that either of you can say, “You’re in everything’s-on-fire mode, take the afternoon”
A 20-minute Friday debrief: “Where did we feel most aligned or misaligned this week?”
Keep it small. The point is to build the habit of designing the relationship, not waiting for the next blow-up to force the conversation.
The bigger picture
Leadership starts with this relationship. The dynamics you and your co-founder model: how you handle disagreement, how honest you are about capacity, how you repair when something goes sideways, are the template your team learns from, whether you intend it or not.
Mona and Ayesha didn’t have a sophisticated system for any of this on day one. Their leadership roles were decided by who raised their hand in a room. But they built something more valuable over time: a habit of not stonewalling each other, of naming the uncomfortable thing early, of checking in on life, not just the company, at least twice a year.
As Mona put it: “Whatever happens, we’re willing to talk it out, even if that takes a while, even if we’re disagreeing on something. Because it’s really worth it.”
That’s the whole framework. The 90-minute exercise above just gives you a structure to do it deliberately, instead of waiting for the pressure to force it.
Founder Circle
I work with a small group of founders who want three things:
Clarity on what actually moves the needle, not just busyness.
A space to think through the hard decisions (co-founder dynamics, team restructuring, fundraising trade-offs) without having to perform with confidence they don’t yet feel.
A peer group that gets it: other founders who are doing the inner work alongside the operational work.
Our next circle meets soon. Grab your spot today.
P.S. Hit reply and tell me one conversation you’ve been avoiding with your co-founder. You don’t need to write the whole story, just the headline. I read every response.
If you want to go deeper to check out the references used in our research:
¹ Gray, S.M., Howell, T., & Sackett, E. “Talking Past Each Other: Construal Level, Utilitarian Motives, and Entrepreneurial Team Formation,” Organization Science, 2024; and “Why Cofounder Partnerships Fail — and How to Make Them Last,” Harvard Business Review, June 2024 — on how co-founders evaluate entirely different things during team formation without disclosing this to each other, and the downstream finding that up to 43% of founders are ultimately forced to buy out their co-founder.
² Baktash, M.B., & Pütz, L. “Detach to Thrive: Psychological Detachment from Work and Employee Well-Being,” Journal of Happiness Studies, 2025 — longitudinal evidence that psychological detachment during off-hours is a key driver of well-being across emotional, job satisfaction, and life satisfaction measures.
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