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.

AI Advisor & Enterprise Architect | Guiding Europe’s AI Innovation & Compliance | Board Member, Author, Speaker | Based in Brussels, EU

AI Advisor & Technology Speaker | Top AI Voice | Board Member | Author | Enterprise Architect
Guiding Europe’s AI Innovation | 102K+ Followers | 50K+ AI Daily Nutshell Readers | Based in Brussels, EU

I am an AI Advisor, Technology Speaker, Board Member, Author, and Enterprise Architect based in Brussels, EU, helping professionals and organizations across Europe understand and adopt AI with clarity, confidence, and responsibility.

With a community of 102,000+ followers on LinkedIn and 50,000+ readers of my AI Daily Nutshell newsletter, I simplify complex AI topics and translate them into practical insights that leaders, teams, and individuals can act on immediately.

For over 20 years, I have worked across enterprise architecture, cloud, data centres, automation, and digital transformation. Today, my focus is on guiding Europe through the fast-evolving AI landscape — from emerging tools and responsible AI practices to policy, strategy, and the impact of the EU AI Act.

My mission is simple:
Make AI understandable for everyone, and empower Europe to innovate with purpose.

I speak at global tech summits, advise organizations on AI strategy, mentor startups, and engage daily with a global community eager to learn, grow, and stay ahead of change.

If you’re interested in:
• Simplifying AI in practical language
• Understanding AI trends shaping Europe
• Enterprise architecture and transformation
• The EU AI Act and responsible AI
• Emerging tools, future skills, and digital leadership
— you will find daily, value-driven content here.

📍 Based in Brussels, EU
🌍 Collaborating with organizations and communities across Europe and beyond
💬 Open to speaking engagements, advisory roles, and meaningful discussions on the future of AI

#AIEurope #EuropeTech #DigitalEurope #EuropeanInnovation
#Entrepreneurship #ITAdvisory #BoardMember #AIInnovation #BlockchainStrategist #TechVisionary

ChandraKumar R Pillai

ChatGPT was asked how to live to 140 years.

No biohacks.
No superfoods.
No billion-dollar routines.

The answer came from how people actually live, not what they consume.
The longest-living people on earth don’t obsess over longevity.
They obsess over meaning, connection, and inner peace.

Less stress.
More presence.

Real relationships over digital applause.
A reason to wake up that isn’t money.
And at least one person with whom you can be fully yourself.

Longevity isn’t extended by years alone.
It’s expanded by how alive you feel while living them.

Swipe through the rules.
Not to live longer.
But to live better.

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#chatgpt

ChatGPT

Same talent.
Same opportunities.
Different results.

The gap isn’t luck or timing.
It’s mindset + daily choices.
One path reacts, avoids discomfort, waits for motivation, quits early, and talks about people.

The other chooses intention, controlled discomfort, consistent action, course-correction, and ideas.
Nothing changes overnight.

But the habits you repeat every day quietly decide who you become.
Choose wisely.

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#success #motivation

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Growth

Most people don’t change because they lack information.
They change when reality hits hard enough.

These 11 images do exactly that.

No motivation.
No feel-good quotes.
Just visual proof of how time, effort, pain, patience, and priorities actually work.

You’ll see why comfort delays growth.
Why small choices compound.
Why ego is expensive.
And why most people wait too long to value what already matters.

Swipe slowly.
If one image makes you uncomfortable, that’s the lesson.

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11 IMAGES

10 AI skills that will quietly decide your career in 2026.

Not your degree.
Not your job title.
Not your years of experience.

AI is becoming the default layer of work.

If you don’t sit on top of it,
you’ll slowly fall under it.

AI won’t replace you.
But someone using AI better than you will.

Start stacking these now.
2026 is closer than it feels.

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#success

AI Skills

Everyone you meet is fighting a battle you can’t see.

The quiet one.
The confident one.
The difficult one.
The “always fine” one.

We judge in seconds.
But understanding takes time.

Behind every action is a story.
Behind every reaction is a reason.

Pause before you assume.
Listen before you label.

The truth usually isn’t what it looks like.
Empathy changes everything.

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#leadership #empathy #success

We don’t have broken kids.
We have tired ones.

Under-slept.
Overstimulated.
Over-sugared.
Disconnected from nature.

Before labeling a child as a problem, ask:
What environment did we put them in?

The cure isn’t more medication.
It’s restoring real childhood.

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Kids

They were told no.
Rejected. Dismissed.

So they built anyway. 🏎️

The brands that rewrote automotive history weren’t backed by approval.
They were built by engineers who trusted engineering over opinions.

Obsessive testing.
Relentless iteration.
Mechanical purity when others played safe.

Not rebellion.
Precision.

The world remembers the logos.
It forgets how many times the answer was NO before the breakthrough.

Love technology?
This is how progress is made.

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Rejection ≠ Dismissed

F.L.Y — not a quote. A way to live.

First, love yourself.
Because everything starts there.

Live fully.
Not later. Not after permission. Today.

Face everything. Rise anyway.

Focus.
Follow one course until successful.

When it gets heavy:
Hold on. Pain ends.

One truth never changes:
Effort never dies.

Consistency builds what motivation can’t.
Keep flying.

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Most people scroll images for entertainment.
High performers extract lessons from them.

These 13 images aren’t aesthetic.
They’re uncomfortable.
They challenge assumptions you didn’t know you were living by.

Each frame carries a signal about power, patience, leverage, time, and human behavior.
Miss it, and it’s just another picture.
See it, and your thinking shifts permanently.

Don’t swipe fast.
Pause.
Decode the message.

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13 IMAGES WITH DEEP MEANING

Same 24 hours.
Different choices.

Which dad are you being today?

Your family doesn’t need perfection.
They need presence.
Physically. Spiritually. Emotionally.

That gap between who you are
and who God called you to be?
It closes with daily discipline.

Show up. Every day.

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Time

A wise man once said:

If you apply this, you win.
If you ignore it, nothing changes.

Swipe →

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A wise man once said:

Life before the internet wasn’t empty.
It was full just in a different way.

No algorithms deciding what you should see.
No dopamine hits on demand.
No pressure to perform, post, or prove.

Conversations had eye contact.
Memories lived in the mind, not the cloud.
Boredom wasn’t avoided it created imagination, ideas, and patience.

Time felt slower because it was actually lived.
Connection felt stronger because it was earned.

Swipe the carousel to revisit a world where being present mattered more than being online.

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Life before Internet

High income is loud.
Real wealth is quiet.

Veronika didn’t win the salary lottery.
No shortcuts. No insider edge.

Just boring habits:
▶️ invest a little
▶️ do it every month
▶️ don’t quit

While others spent and scrolled,
she stayed patient.

That’s how wealth is built.
Not with big moves —
but with small decisions repeated for years.

You don’t need to be rich to start.
You need to start to become rich.

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Real Wealth

Freedom feels good.
Competence compounds.

A Chinese mother was once asked
why she doesn’t ask her child’s opinion.

Her answer made many Western parents uneasy.

Kids don’t naturally optimize for long-term returns.
They choose play over effort.
Comfort over challenge.
Now over later.

That’s biology. Not failure.

Different cultures engineer for different outcomes.

One prioritises expression early.
The other prioritises capability early.

Both create adults.
Just… very different ones.

The data shows something uncomfortable:
Training before freedom compounds faster.

Freedom isn’t taken away.
It’s delayed.

And eventually, earned.

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Fun fact that changes how you think about money 👇

If something costs $800
and you buy it on sale for $500…

You didn’t save $300.
You spent $500.

Because savings isn’t about discounts.
It’s about intent.

If you didn’t plan to buy it at $800,
the “saving” never existed.

Sales don’t make you richer.
Better decisions do.

Money grows when you stop confusing
feeling smart with being smart.

Swipe → to see why this mindset matters more than any sale tag 💡

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#success

Fact

Most people aren’t broke on opportunity.
They’re broke on skills.

And the crazy part?

Some of the highest-leverage skills on the planet
are available for free.

No ads.
No fluff.
No “buy my course” nonsense.

Just real platforms that actually teach you something useful.

Here are 7 websites that offer FREE courses
Swipe → Learn → Execute → Win.

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7 WEBSITES THAT OFFER FREE COURSES

Time was never the enemy.
Lack of structure was.

Top performers don’t “manage time.”
They design their days with clear frameworks that eliminate decision fatigue before it even shows up.

While most people react to their calendars, high performers run proven systems that decide:
▶️ what gets attention
▶️ what gets ignored
▶️ and what actually moves the needle

This carousel breaks down 10 time-management frameworks used by top performers to stay focused, calm, and consistently ahead without longer hours or burnout.

Borrow the frameworks.
Upgrade how you use time.

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Time Management

Some images don’t just catch your eye.
They quietly rewire your thinking.

This carousel isn’t about shock value.
 It’s about perspective.

14 images.
14 moments where your brain pauses and says,
 “Wait… I never saw it that way.”

Sometimes growth doesn’t come from new information.
It comes from seeing the same world through a different lens.

Swipe slowly.
Let it land.

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#success

14 Images

A wealthy Sheikh in Dubai once told me:

“Money loves water.”

It took me years to understand what he meant.

Most people believe money disappears because they don’t earn enough.
That’s not the real reason.

Money behaves like water.

When it flows with intention, it grows.
When it sits still, it quietly evaporates.

I’ve seen people with the same income end up in completely different lives.

One kept everything “safe.”
No risks.
No new skills.
No growth.

Inflation did the rest.

The other kept money moving.
Into learning.
Into businesses.
Into boring, real assets.

Not perfect.
Plenty of mistakes.
But always in motion.

That’s the difference no one explains.

Wealth isn’t built by hoarding.
It’s built by circulation.

Move your money with purpose.
Into assets.
Into skills.
Into growth.

Save this.
It’ll make sense later.

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Money

𝗝𝗮𝗽𝗮𝗻 𝗯𝗮𝗻𝗻𝗲𝗱 𝗲𝘅𝗮𝗺𝘀 𝗳𝗼𝗿 𝗰𝗵𝗶𝗹𝗱𝗿𝗲𝗻.
𝗔𝗻𝗱 𝘁𝗵𝗲 𝗿𝗲𝘀𝘂𝗹𝘁𝘀 𝘀𝘁𝘂𝗻𝗻𝗲𝗱 𝘁𝗵𝗲 𝘄𝗼𝗿𝗹𝗱.

No ranks.
No pressure-filled report cards.
No labeling kids as “topper” or “average.”

Instead, Japan focused on something radical:

→ Curiosity over cramming
→ Learning pace over comparison
→ Character over marks

Teachers started observing:
How a child thinks.
How they solve problems.
How they collaborate.
How they handle failure.

And here’s what happened:

✔ Less anxiety, more confidence
✔ Better problem-solving skills
✔ Stronger emotional intelligence
✔ Kids who actually enjoy learning

The biggest takeaway?

Exams measure memory.
Life measures understanding.

When education shifts from proving intelligence
to building intelligence,
everything changes.

Maybe the future of learning isn’t about asking
“How much did you score?”
but “How well did you grow?”

Food for thought.

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🌱 Jason Shen

ChandraKumar R Pillai

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The Battle

🌱 Jason Shen

ChandraKumar R Pillai

Followers

Posts

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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