Helping unconventional founders & execs lead through hard pivots · Author: THE PATH TO PIVOT · Uncle Iroh with a side of Genie · 3x venture-backed startup founder · 1st gen immigrant · ADHD · Meta + Etsy alum

You’ve been avoiding a hard conversation with your cofounder. You know the one.

Years ago, I was you. Started a company with two close friends, raised money, hit every milestone. And watched the partnership fall apart in slow motion because none of us could speak honestly about how we felt.

We were “conflict-avoidant,” which sounds peaceful but actually meant unspoken tension and resentment built up silently. By the time we tried to address it it was too late. That company didn’t survive. The friendship eventually recovered.

I became obsessed with understanding why. I studied  with the Gottman Institute and poured over partnership dynamics research. What I found: most cofounder conflicts follow patterns. And they respond to specific interventions if you know what they are.

Now I coach founders through the same thorny problems that took years off my life. 

Hi, I’m Jason Shen - executive coach, author, and ice cream fiend. 

As a 3x founder, YC alum, and former product leader at Meta and Etsy, I’ve lived both early-stage chaos and operational discipline at scale. I bring both to my work.

More on what I do: 

➣ COFOUNDER CONFLICT COACHING

I help cofounders repair their working relationship before they ruin their company. In a 13 week partnership intensive, you will reconnect with your most crucial ally, find common ground, and gain the skills needed to collaborate at full strength. 

Learn more: https://cofounder.repair

➣ 1:1 EXEC COACHING

Not every founder problem is a partnership problem. I also work 1:1 with founders facing pivots, transitions, and the kind of decisions where the stakes are high and the right answer isn’t obvious. Same in-the-trenches perspective, focused on you.

Discovery call: https://calendly.com/jason-shen/discovery

🌱 Jason Shen

I couldn't disagree with OP more. And the data backs me up.

The top 10 tech giants average 2.3 founders 👇

1. NVIDIA: Huang, Priem, Malachowsky
2. Google: Page, Brin
3. Apple: Jobs, Wozniak
4. Microsoft: Gates, Allen
5. Amazon: Bezos (MacKenzie had significant early role)
6. TSMC: Chang (founded as a joint venture w/ 🇹🇼 gov't)
7. Broadcom: Nicholas, Samueli
8. Meta: Zuckerberg, Saverin, Moskovitz, Hughes
9. Tesla: Eberhard, Tarpenning (Musk bought his title later)
10. Tencent: Ma, Zhang, Xu, Chen, Zeng

Oh, and YC had 4 founders, Anthropic has 2, and OpenAI had 11(!)

Bottom line: Being a solo founder to avoid arguments is midwit thinking.

When you know how to engage in productive conflict with your cofounders, your company makes better decisions and executes faster in the long run.

Getting to alignment is a skill issue.

Jason 🧠 Shen

Helping cofounders repair their partnership · Exec coach to ambitious outliers & brilliant misfits · 3x founder & YC S11 alum · Author of ‘The Path to Pivot’ & ‘Weirdly Brilliant’ · Retired NCAA 🏆 gymnast

Founder: "My cofounder is checked out."

Me: "How do you know?"

Founder: "They're not putting in the hours like they used to."

Me: "Have you asked them what's going on?"

Founder: "I don't want to make it weird."

Me: "So you'd rather assume the worst than have a conversation."

Founder: "Umm.."

Me: "Founders don't just become lazy and unmotivated for no reason. Checked out often means quietly drowning or becoming misaligned. Both can be fixed by talking things out."

You might be one honest conversation away from getting your cofounder back.

1. This is what every technology does -- it commodifies human labor and expertise in a given domain so more can benefit

2. This is the wrong way to think about AI getting good at your area of expertise. The new adopters of the technology will never have the same appreciation for the history, craft, and edge cases.

But you do.

Which means you will be able to do more with the technology than they can, assuming you are willing to be less precious about what you do now that tech can do as good or better and act with a beginner's mind.

Technology is how our species advances. There will be mistakes and harm along the way, but we generally figure it out, eventually, for the benefit of more and more people.

Between 20-35% of startups will have at least one founder leave within 4 years.

Not every founder departure is bad.

Differing visions
New interests
Personal circumstances

All can be good reasons for cofounders to split

What's unfortunate is seeing cofounders who complement each other's strengths - and once worked together well - have a falling out.

Often it's due to compounding disappointment or resentment. Related to unspoken expectations or never fully explored misunderstandings.

Startups are stressful and that puts pressure on relationships.

Departure is sometimes the only way forward. Senja is still going strong even if one of the founders is no longer there.

But like a total rewrite of your codebase - it should be a decision of last resort.

Having a cofounder to start a company together with is only net-positive if you trust them 100% and value the relationship over the business.

You are fundamentally giving up control over your company to another person in exchange for their ability, commitment, and aligned interest.

That partnership is the beating heart of your business.

You have to protect it as fiercely as your banking credentials, your product's secret sauce, your production database.

But too often founders take it for granted until they're in crisis.

They skip their founder 1:1's
They blame their cofounder for company woes
They let resentment quietly build

It's like the way we think about health

You can either eat cleaner and move more now.
Or you can get triple bypass heart surgery later.

A pattern I've noticed across several cofounder conflict client calls I've had in the last month:

Friendly and enthusiastic CEO who can inspire / close  customers and investors but is a bit disorganized and unreliable at times

Disciplined and detail oriented CTO who pulls long hours to build a great product but has a bit of a temper and can be resentful of CEO.

Has anyone else seen this pattern? What do you make of it?

I have my own thoughts but I'm curious to see what people thing.

Great companies are built by founders with different strengths, skills, and temperaments.

▸ 10x engineer + deal-hungry salesperson
▸ Slick designer + genius growth marketer
▸ Disciplined operator + creative visionary

It makes perfect sense: get someone who is strong where you are weak.

But here's the problem.

One of you values organization.
The other values freedom.

One of you values craft.
The other values speed.

You are fundamentally going to see the world in a different way.
That's the whole reason why you teamed up.

But there's a real risk of interpreting your differences in approach as a failure of morals, respect, or competence.

"What is wrong with them? How could they think / do / say that?!"

You partnered with this person precisely because they are different from you in a significant way. Even if they shared a similar vision or mission.

You have to expect that you'll disagree and butt heads.
A mature entrepreneur knows this and responds accordingly.

"Oh interesting, you took a different approach. Can you help me understand why?"

Sometimes you'll end up going your way, sometimes theirs, most times it'll be some third option you didn't think of until you dug into the disagreement.

"Grow up" is a lazy way of saying "I don't want to deal with your emotions."

Laziness rarely leads to great outcomes.

Startups are stressful and extended periods of high stress put people in fight-or-flight.

Fight-or-flight (ie sympathetic nervous system activation) significantly impacts the prefrontal cortex, the part of our brain that does rational thinking.

So just having a conversation isn't enough.

What's the answer?

Slow down.
Ask questions.
Listen for the feelings behind the words.
Reflect what you hear.
Validate the parts that make sense.

This is what brings people out of fight-or-flight.

THEN you can try to have a rational conversation about what's wrong.

Holloway

Author

Figma

Content Strategist, Editorial

Wonder Shuttle

We make publications, resource centers, and technical manuals. Selected customers: Shopify, Twilio, Wattpad, Civic Innovation Office (City of Toronto), Skillshare

https://www.wondershuttle.com/

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