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.

Northwestern University - Kellogg School of Management

As a Program Leader for Kellogg's Product Management Executive Education course, I lead dozens of students through content as they transition into and develop as product managers.

Program Leader Instructor - Product Management

Vimeo

Director of Product Management

Principal Product Manager

Lead Product Manager

Squarespace

• Led a new product that will launchd as an add on for Squarespace. The product is the most requested feature from over 4,000 users 
• Led three design sprints with the team to develop new features and Squarespace templates. 
• Worked alongside executive leadership and pricing specialists to conduct a market analysis and define the pricing strategy for this add on product. Surveyed over 800 site owners with a conjoint analysis that resulted in the product being sold as an add on to Squarespace growing portfolio of products.
• Recruited Beta users and ran usability tests to assess the usability and product market fit of the product
• Worked alongside management to descope and reposition the product to be Beta ready after the prior team had stalled on development for over 14 months. 
• Launched Subscriptions for Merchants which is now used by over 13,000 merchants and has generated over $30MM in platform GMV.  
• Launched Apple Pay and PayPal for Donations which have collected over $13 million dollars for non profits on Squarespace.

Product Manager

LiveAuctioneers

A Bessemer Ventures funded company - $47MM

Building product at the world's largest luxury auction market place. Responsible for the majority of core features including absentee and live bidding, Payments, buyer approval, seller tools, catalog and item pages, Saved Items and My Bids.

• Increased year to date revenue 49% by implementing pricing changes to core products and services.

• Built an in-house payment processor, Payments, that helps process millions in transactions per year. Led the design and execution of the website integration, checkout experience, notifications, and externally facing dashboards for reporting and administration. Payments simplified the process of manual billing and collecting commissions.

• Managed a .01% fraud rate, protecting auctioneers and well meaning buyers from inflated prices. Implemented a machine learning tool that analyzes fraud activity and provides a $10MM financial safety net for auctioneers.

• Led a nine month effort to increased site speed and performance. By migrating the front end architecture and server side rendering, site speed increased 70%. Involved migrating over a dozen key features and pages which are core to the business including: the Homepage, the Seller page, the Catalog page, the Item page, Account Settings, Saved Items, My Bids, Auctions Near Me.

• Recovered a 30% year over year decline in search engine rankings by addressing a multitude of SEO issues. 

• Decreased auction approval times by 40%. 200,000 more buyers are approved monthly within an hour of registration.

• Released the iOS app after two years of not being released. Decreased crash rate to .9%.

• Enabled reporting and performance visibility into 500,000 monthly triggered emails by moving to a new email provider.

General Assembly

$119.5MM in total funding. 

• Co-taught and facilitated the 10 week Product Management course. Content and topics covered for 25 students per class include: MVPs, Business Models, wire framing, user stories, metrics, a/b testing, and writing product specifications.

• Received the highest Net Promoter Score (NPS) for student-instructor satisfaction. 76 NPS for the class and 94 NPS for the instructional team.
https://generalassemb.ly/education/product-management/new-york-city

Product Manager in Residence

Maker's Row

A Comcast Ventures backed company - $1MM

Product Manager for the market place/SaaS product that provided a platform for domestic manufacturers to connect with buyers.

• Worked closely with a team of three engineers, two designers and a data analyst to conduct user research, wireframing and QA testing to continually develop the product in meeting roadmap deliverables.

• Revamped the SaaS pricing structure to properly monetize the platform and create a more efficient matching process. Having done this, the new pricing structure successfully tripled (3x) MRR (monthly recurring revenue). The entire process included competitor research, testing, a database migration, 
and a rewriting of our payment scripts. 

• Collaborated with the engineering team to launch the Maker’s Row payment processor written as a stand alone Python application. My role in specifying the product specifications assisted in the technical decision to use said language. The processor was to be used by over 3,000 factory partners and was integrated with WePay Clear as our provider. 

• Redesigned our Projects platform to help buyers outline their requests in an easy to read online format. This lead to a significant increase in our online budgets that grew 20% per week and culminated in $7MM in unactualized budgets. 

• Collaborated with engineering to successfully create a search product called ‘Match Making’. ‘Match Making’ is a refined search algorithm that displays more relevant search results to users by proper key word and stage matching for a users Project. 

• Developed wireframes that were used to launch three landing pages for new product releases.

• Partnered with the designer to continually review UX, wireframes and do usability testing.

• Designed an A/B test for our sign up and activation flow that increased sign ups and activations by 26%.

Lean Startup Machine

• Led internal trainings on lean startup methodology and MVP training for 100s of entrepreneurs and dozens of enterprise practitioners that included The White House, Deloitte, USPS, Lockheed Martin, American Express,  Adobe, and Kauffman Foundation. 

• Worked with clients to integrate lean startup process into their organization and construct MVP’s.
Scaled operations from an initial 21 cities to 41 global cities on 6 continents. 

• Drove an increase of revenue by 51% for the year by successfully identifying and improving key performance metrics.

• Increased profit margins by 10%. New revenue opportunities were derived with costs were normalized across markets.

• Decreased the time to market by 21 days through a refined training program for the sales and operation team.

• Broadened revenue stream by creating the licensee program which set the stage for more global scaling.

Director of Operations

Skillshare Company

Worked with over 100 entrepreneurs to date by teaching them methodologies and frameworks to get their business ideas off the ground. My two classes 'Passion to Prototype' and 'How to Create and Develop a Business Model', were popular classes amongst Skillshare students.

Master Teacher

TechStars

Spring 2013 New York City class as a part of Lean Startup Machine and 'The Validation Board'.

Inductee

Franklin's Lab

Founded and managed a consultancy for startups that positioned founders to better succeed by evaluating their business models and strategy. Leveraged the expertise of several venture partners to deliver on business intelligence and execution.

Founder

Experienced Product Manager and operator who enjoys the craft of building internet technology products for the world. A taste for financial modeling, semi time instructor,  and yogi. 

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🌱 Jason Shen

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