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.

MMK Marketing, The Retail Experience Agency

• 𝗣𝗿𝗼𝗯𝗹𝗲𝗺: Multiple clients struggle to distinguish noisy data from meaningful signals, leading to slow or misguided decisions.
• 𝗔𝗰𝘁𝗶𝗼𝗻: Research, conceptualize, and pitch a metrics framework (incorporating metric standardization, metric trees, XmR charts, and Weekly Business Reviews, among other tools) to help teams systematically test growth hypotheses and measure results.
• 𝗥𝗲𝘀𝘂𝗹𝘁: Strengthened MMK’s data-driven reputation—sparking a series of client conversations and earning internal recognition for initiative—while continuing to develop frameworks that help teams systematically test growth hypotheses.

Senior Data Analyst

• 𝗣𝗿𝗼𝗯𝗹𝗲𝗺: A B2B CRM client was channeling ad spend into leads who rarely converted, suggesting major misalignments between marketing and product usage data.
• 𝗔𝗰𝘁𝗶𝗼𝗻: Led an exploratory analysis using product usage, web analytics, and ad performance data (using SQL + Python) to identify friction points in the onboarding flow. Presented an “activation funnel” concept that spotlighted critical user drop-offs and underperforming channels.
• 𝗥𝗲𝘀𝘂𝗹𝘁: Drove a cross-functional repositioning involving marketing, product, customer success, sales, and leadership that doubled monthly customer acquisition while cutting ad spend by 50%, achieving 4x improvement in CAC efficiency through rapid experimentation and channel optimization. Provided weekly insights that fueled continuous website, landing-page and email-campaign optimization.
• Additionally, supported 4 other B2B and B2C clients by assessing project opportunities, refining growth strategies, and providing data analysis to inform marketing optimizations.

Marketing Data Analyst / Growth Analyst

Omdena

• 𝗣𝗿𝗼𝗯𝗹𝗲𝗺: ESG (Environmental, Social, Governance) reports were largely unstructured, making it hard for stakeholders to measure corporate sustainability performance.
• 𝗔𝗰𝘁𝗶𝗼𝗻: Helped build a custom ETL pipeline (Python, text-extraction libraries) to transform dense text into structured data. Leveraged language analysis to rank companies' ESG factors.
• 𝗥𝗲𝘀𝘂𝗹𝘁: Accelerated the development of an ESG benchmarking system, enabling project leads to compare corporate reports more efficiently.

Junior Machine Learning Engineer

SpaceLab

• 𝗣𝗿𝗼𝗯𝗹𝗲𝗺: Difficult to identify planets due to noisy, high-volume NASA and Caltech data.
• 𝗔𝗰𝘁𝗶𝗼𝗻: Leveraged Python (TensorFlow, scikit-learn) to optimize a convolutional neural network’s hyperparameters, improving feature extraction from time-series data. 
• 𝗥𝗲𝘀𝘂𝗹𝘁: Enhanced the ML pipeline for exoplanet detection by refining the CNN architecture and hyperparameters, resulting in noticeably improved detection accuracy.

Data Scientist | Machine Learning Engineer

General Assembly

• Collected, cleaned, and integrated diverse datasets using Python and SQL, ensuring quality data for analysis.
• Conducted exploratory and statistical analyses to uncover trends and validate hypotheses.
• Engineered predictive models using machine learning and natural language processing techniques.
• Employed systematic frameworks from hypothesis generation to outcome validation to achieve repeatable analytical success.
• Synthesized complex findings into intuitive visualizations and narratives, while managing data workflows with Git to maintain reproducibility and collaboration.

Data Science Fellow

ElephantBlack

• 𝗣𝗿𝗼𝗯𝗹𝗲𝗺: Clients lacked evidence-based approaches to validate ROI for multi-channel marketing campaigns (search, social, email). Many relied on guesswork and saw inconsistent results.
• 𝗔𝗰𝘁𝗶𝗼𝗻: Co-founded agency with a data-first approach—integrated quantitative analyses (e.g., sales trend analysis, segmentation) into brand positioning, creative strategy, and multi-channel CRO efforts. Designed test plans to optimize ad copy and landing pages across paid search, social, and email channels using A/B testing frameworks.
• 𝗥𝗲𝘀𝘂𝗹𝘁: Achieved up to a 52% uplift in marketing returns across key accounts and secured 12–13x ROAS for select eCommerce clients through multi-channel analysis and optimization recommendations.

Co-Founder

Sean Atkinson

• Provided high-quality copywriting services for digital campaigns, websites, and marketing materials, collaborating closely with diverse clients to capture their brand voice and drive engagement. 
• Managed the complete content lifecycle from concept to delivery while consistently meeting project deadlines.

Copywriter

Terapeak (Acquired by eBay Inc.)

• Drove sales for a specialized SaaS analytics platform by leveraging data-driven strategies and digital selling techniques to secure new customers and expand market share. 
• Delivered compelling product demonstrations and managed the entire sales cycle in a dynamic, competitive tech environment, contributing to Terapeak’s market growth.

Sales Executive

Info-Tech Research Group

• Developed new business opportunities, grew pre-existing accounts, and resurrected dormant accounts across North America, Europe, and Africa using strategic prospecting and consultative selling. 
• Ranked in the top 10% in both prospecting and daily productivity.

Business Development Manager

University of Toronto

• Managed circulation, inter-library loan services, and resource organization at the Gerstein Information Centre, University of Toronto, while providing exceptional support to librarians and addressing patron inquiries. 
• Streamlined processes and maintained accurate records to enhance the library’s operational efficiency.

Assistant Library Technician

• Supported a professor’s research by conducting literature reviews, collecting and analyzing data, and assisting in the preparation of academic reports, papers, and publications. 
• Collaborated on project planning and logistics to ensure timely and high-quality research outcomes.

Research Assistant

BL Clark

• Identified and secured private financing deals for publicly traded micro-cap companies by negotiating and structuring tailored financing packages designed to fuel business growth and broaden market presence. 
• Facilitated cross-functional communication among financiers, lawyers, and bankers to ensure seamless deal execution and expand the customer base.

• Conducted comprehensive market research and financial analysis to track global trends and identify promising investment opportunities, maintaining a detailed watchlist of over 15,000 companies. 
• Produced insightful reports and strategic recommendations that informed key investment decisions for global investors.

Research Analyst

Data Analyst | SQL + Python + Tableau + Excel | 12 Years in Sales & Marketing | Transforming Complex Data into Insights

During my 6th birthday celebration, mom burst into my room. I had some close friends over, and we were playing with my new gift—my very own LinkedIn account. Oh my.

I’m still waiting for people to accept the connection requests I sent out that day.

𝗠𝘆 𝗯𝗿𝗮𝗶𝗻 𝗱𝘂𝗺𝗽𝘀 𝗼𝗻 𝗵𝗲𝗿𝗲 𝘂𝘀𝘂𝗮𝗹𝗹𝘆 𝗿𝗲𝘃𝗼𝗹𝘃𝗲 𝗮𝗿𝗼𝘂𝗻𝗱:

1. Data-Driven Growth Strategy
2. Strategic Thinking + Operational Excellence
3. AI + Analytics
4. Personal + Professional Growth
5. Marketing + Product + Experimentation

All served up with a generous side of business-building brilliance.

Some of my posts are 𝘴𝘭𝘪𝘨𝘩𝘵𝘭𝘺 unhinged but in a haha funny way, not in a someone please check on this man sort of way.

If you're still reading this, you're either intrigued or accidentally clicked 'see more.' 

Either way, welcome.

taplio

The Battle

🌱 Jason Shen

Sean Atkinson

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taplio

The Battle

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Sean Atkinson

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Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}🌱 Jason Shen's LinkedIn Performance

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Performance Score🌱 Jason Shen's LinkedIn Performance