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

90% of startup founders will never need to hire a conflict coach if they just do one thing every single week.

It's not complicated. It's a 30m weekly meeting where you and your cofounder talk about how you're actually doing.

Not the roadmap.
Not the next release.
Not the latest metrics.

But how you're doing as people and as partners.

I call it the Founder Heart-to-Heart

Yes yes I know you already talk to your cofounder all time in standup, planning meetings, Slack, etc

But all of that is operational. It's about the work, the problems, the tactics.

Conflict happens when two founders drift, not on the task level, but on the process, role, and vision level.

You don't clarify things. You make assumptions. You jump to conclusions.

And over time, that drift creates a rift and mistrust.

I did this with my cofounder Wayne with Headlight & MIdgame nearly every week and it saw us through funding challenges, growth plateaus, hard pivots, team turnovers and more.

So what do you talk about during your Heart-to-Hearts?

Up to you but here's 4 questions you can use (or build your own with a deck of Cofounder Mode from Annie Garofalo and Francois Le Nguyen)

1. What are you grateful for?

What your co-founder's been doing that you noticed, what's going well, what's good in life outside work. This is about remembering your co-founder is a full person, not just a function.

2. What's stressing you out?

The rule here is NO problem-solving. Don't jump to fixes. You'll have plenty of meetings for that. This one is for listening and making sure you actually know what's weighing on other.

3. What questions or puzzles do you have for me? This is the closest you get to feedback, but framed as curiosity. "I noticed you said you'd own that hire, but I haven't seen movement — did something change?" Not an accusation. A clarification.

4. What are your hopes and dreams?

End on something positive. Short-term, long-term, doesn't matter. "I really hope this deal lands." "I want us to exit for a ridiculous number." You didn't start a company without big visions — this is a chance to share them.

Two more things to keep in mind:

Change the setting. Go for a walk, hit a coffee shop. Make it feel different from every other meeting on your calendar.

Schedule it and protect it. Don't skip it when things are busy or when things feel fine b/c that's exactly when the drift starts. Don't let it become a venting session or a planning meeting. Keep it about the two of you.

If this sounds a lot like a marriage or couple's check in, you're not wrong. The principle is the same: an important relationship needs time to tend to itself.

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

Sometimes cofounders in conflict talk about wanting to just communicate "like professionals".

While I get what they mean, they misunderstand the nature of a startup.
Being professional is a waypoint to an optimal partnership.

Because great founders are often the antithesis of professional.

They're passionate, intense, unreasonable, impatient, unrelenting, and often delusional (in the best way).

To truly make it through the trough of sorrow that every startup faces, you need to have more than just a "professional" relationship with your cofounder.

You need to feel like this is someone you will fight for, who will have your back, whose life you deeply care about, who you trust enough to put your life in their hands.

That's far beyond a mere "professional" relationship.

Of course constant bickering and fighting does no one any good. But removing that is not enough.

I want you to walk away knowing you have a partner who you can truly count on.

Coach to Product Leaders | ex-Facebook, Instagram, Nokia, eBay, Skype, Microsoft

I spent 27 years optimizing products for billions of users at Meta, Microsoft, Skype, and Nokia. We had rigorous frameworks for shipping code, managing KPIs, and scaling tech.

We had few frameworks for managing the human operating system driving it all.

I watched brilliant leaders suffocate under the "Asphalt."

In my book, I define the Asphalt as the "clearer path to lesser goals." It is the artificial layer of safety, optics, and "good enough" that society paves over our true potential. Most leaders don’t lack skill; they lack alignment. They are trapped beneath the weight of expectation, shipping the org chart instead of the product.

I codified the process of breaking through into a structured system: The S.E.P.A.R.A.T.E. Framework™.

This is a proprietary tool I created to help leaders break through the pavement of convention. Today, I serve as an Executive Coach and Consultant for those ready to stop managing friction and start engineering flow. I use this framework to debug performance with the rigor we apply to code. No fluff, just root-cause analysis and architectural repair.

HOW I PARTNER WITH CLIENTS:

1. LEADERSHIP TEAMS: The "Alignment Diagnostic" & Intervention. We identify the 5 signs of "Destructive Discomfort" that are silently draining your capacity and install the protocols to fix them.

2. LEADERS & HIGH-PERFORMERS: 1:1 Alignment Coaching I partner with Execs, Founders, and individuals to audit their professional lives. We identify where you are buried under the "Asphalt" (Safety/Convention) and build the strategy to break through to your "Steeper Path" (Growth/Purpose).

3. THE MANUAL: Breaking Asphalt My book, Breaking Asphalt: Choosing the Steeper Path to Greater Goals, is the tactical documentation of this system. (Available globally).

4. THE STORIES: The Steeper Path. I host The Steeper Path podcast and newsletter, exploring the mechanics of alignment with other industry leaders.

READY TO UPGRADE YOUR OPERATING SYSTEM?

I work comfortably with a small roster of high-impact clients. If you are ready to break through, let’s have a brief conversation to see if we are a fit for each other.

Book an Intro Call: https://app.paperbell.com/checkout/packages/96280

Newsletter: https://lennpryor.kit.com/75a08a3fcf

Podcast: https://thesteeperpath.buzzsprout.com/

Lenn Pryor

I am losing 3 weeks of productivity this month ... and I am okay with it.

I had a whole calendar planned for February. 

Life had other ideas.

Last week, my entire house was taken down by the flu. Not a "power through it" cold, but a full system shutdown for us all. 

This week began with the start of the Chinese New Year holiday here in Singapore, a time for family and stillness, not hustle. Next week, I fly home to the USA via Germany with a stop over to be with a close friend who is undergoing cancer treatment.

In the old days, I would be freaking out right now.

• “𝘐’𝘮 𝘭𝘰𝘴𝘪𝘯𝘨 𝘮𝘰𝘮𝘦𝘯𝘵𝘶𝘮.”
• “𝘛𝘩𝘦 𝘢𝘭𝘨𝘰𝘳𝘪𝘵𝘩𝘮 𝘸𝘪𝘭𝘭 𝘱𝘶𝘯𝘪𝘴𝘩 𝘮𝘦.”
• “𝘐 𝘯𝘦𝘦𝘥 𝘵𝘰 𝘲𝘶𝘦𝘶𝘦 𝘶𝘱 10 𝘱𝘰𝘴𝘵𝘴 𝘴𝘰 𝘯𝘰𝘣𝘰𝘥𝘺 𝘬𝘯𝘰𝘸𝘴 𝘐’𝘮 𝘨𝘰𝘯𝘦.”
  
Writing 𝘉𝘳𝘦𝘢𝘬𝘪𝘯𝘨 𝘈𝘴𝘱𝘩𝘢𝘭𝘵 taught me that 𝗿𝗶𝗴𝗶𝗱𝗶𝘁𝘆 𝗶𝘀 𝘄𝗵𝗮𝘁 𝗰𝗿𝗮𝗰𝗸𝘀 𝘂𝘀.

In Chapter 14, I wrote: "𝘓𝘪𝘧𝘦 𝘳𝘢𝘳𝘦𝘭𝘺 𝘶𝘯𝘧𝘰𝘭𝘥𝘴 𝘢𝘤𝘤𝘰𝘳𝘥𝘪𝘯𝘨 𝘵𝘰 𝘱𝘭𝘢𝘯... 𝘈𝘥𝘢𝘱𝘵𝘢𝘣𝘪𝘭𝘪𝘵𝘺 𝘪𝘴 𝘢𝘯 𝘦𝘴𝘴𝘦𝘯𝘵𝘪𝘢𝘭 𝘴𝘬𝘪𝘭𝘭 𝘰𝘯 𝘵𝘩𝘦 𝘳𝘰𝘢𝘥 𝘵𝘰 𝘢𝘭𝘪𝘨𝘯𝘮𝘦𝘯𝘵." .

Sometimes, alignment looks like hitting KPIs. 
Sometimes, alignment looks like lying in bed recovering. 
Sometimes, alignment looks like flying halfway across the world to hug a friend.

If I tried to force "thought leadership" posts right now, it would be fake. It would be noise.

So, I’m calling a pause. I’m taking the hit on "productivity" to invest in "humanity."

I’ll be back in my routine in early March. 
Until then, I hope you are listening to your own life when it tells you to stop.

Former Product Leader (Meta, Microsoft, Skype) turned Executive Coach. helping leaders engineer flow and escape the “Safety Trap.” | Author, Breaking Asphalt

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