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.

I love nerding out about startup fundraising

(I know, that’s kinda weird)


After leading fundraising at multiple startups, here’s the question I kept returning to:

- "Why can some founders run a high-momentum, high-leverage fundraise process?"
=> (resulting in a term sheet & VC partner they were proud of)

- "While for other founders (often with strong backgrounds!), fundraising is chaotic… a never-ending ordeal of chasing investors, endlessly updating the pitch deck, and timelines dragging out for months”


...and so a few years ago, I left my full-time job and embarked on a solopreneur journey, with a mission to help startup founders run high-quality fundraises.

I feel like I've found my calling and love learning every day, constantly trying to better understand the craft of startup fundraising. But most of all, I love working 1:1 with founders to help them raise from VCs, Angels, etc.


.....


By the way, if you've made it this far and you're wondering "who in the world is Jorian?" then here's a very quick background:
→ I grew up a math nerd in the US, spending time on AoPS and MathCounts. I even went to a math camp for a whole summer!
→ I went to UNC (Go Heels!) for undergrad, studying Economics and Education. Made some of my best friends for life there.
→ Started working at Microsoft - which was an amazing training ground - but I was often restless and looking for startup experiences. I helped build a startup with some friends, partnered with Msft engineers to build new products, and took a half-year leave to lead a startup fundraise.
→ I studied at Harvard for my MBA. During this time, I made a full pivot to startups, and begun helping any startup I could with its fundraising. Also spent some time sourcing deals at Owl Ventures, the largest EdTech VC in the world.
→ Since becoming a startup fundraising "sparring partner," I've coached 50+ founders who've raised over $190M. It brings me tremendous joy getting to work with great founders, day-in, day-out.

Jorian Hoover

You're raising $3M from VCs on the back of $500K in ARR. You have a list of 80 target VCs ... but only TWO have responded to your emails:

Now you're scratching your head. Everything felt like it was in the sweet spot — you're building in AI, you've hit $500K ARR quickly, and your raise amount is reasonable.

Yet only TWO VCs responded to request meetings with you.

The problem is, you cold emailed all 80 VCs.

Worse yet, while everything felt "in the sweet spot" to you, your deal came across as plain vanilla to the VCs. Tens of thousands of startups have $500K ARR and are building in AI.

I'm not here to tell you that cold email can't work.

But I am here to tell you that warm intros work 100x better than cold intros when reaching out to VCs.

Why?

Try stepping inside the shoes of a VC and you'll realize they're bombarded with thousands of startups reaching out across email, LinkedIn, and Twitter each year.

These VCs need a sorting mechanism, and so receiving a deal from a trusted source (aka a warm intro) makes it more likely they'll schedule a call.

So if you're considering reaching out to 80 VCs for your upcoming fundraise, try and secure warm intros to those VCs. If you don't know people who can introduce you, then go make connections with VC-backed founders who can introduce you.

And if you must cold email, try to personalize your message and appear spikey in some way — after all, VCs want to know why you'll be the 1 in a 1000 that becomes a unicorn.

You've got this, founders.

______________

Hi, I'm Jorian Hoover - I work 1:1 with founders to run high-quality fundraises and have helped 50+ founders raise over $190M. Every week, I share the latest top venture deals & tactics to raise from elite VCs. If you'd like to receive this weekly briefing, subscribe to my "Into the Ring" newsletter at https://lnkd.in/ezj_zYXz

I help founders run high-quality fundraises | Harvard MBA | $190M+ raised

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