Exited founder turned CEO-coach | Helping founders discover who they are as leaders and build high-performance, low-drama companies

Over 15 years I founded and served as CEO to three VC backed companies (one big exit and two learning experiences), all while presenting only the most polished, hyper-competent version of myself and my company, at all times. And then, in 2020 I left it all behind.When I signed the papers, officially removing myself as CEO of the company I’d started a decade prior, it felt like I’d been punched in the gut.Without my persona as the “CEO of VNN,” I realized that I had no idea who I was anymore, or what to do with my life.It was the opportunity of a lifetime.I spent the next 2 years searching, meditating, hanging out with monks, diving into psychedelics, and trying on new identities that never felt right.I was stuck.And then, I finally opened up.I started being honest about my struggles, despite the voice in my head telling me to play a role. I let go of my compulsion to be “Ryan the CEO,” or “Ryan the entrepreneur,” or even “Ryan the guy who’s raised a ton of money and scaled a media company.”I was just, Ryan.And the most surprising things happened.1. The more I opened up, the more everyone else did around me. My network grew and developed into one of deep relationships spanning life and business.2. The more I let go, the more the universe seemed to place exactly what I needed on my doorstep. Things began to happen organically, in ways much better than I could have planned.3. The quieter my mind got, the more I was able to access an innate wellspring of creativity and inspiration that, frankly, made work feel easy and joyful.Me, the guy who’d worked so hard his whole life to be perfect, when I learned to let go and be me, great, meaningful work flowed out of me.And from that foundation, I started Inside-Out Leadership, a boutique executive coaching firm that helps founders transform their companies into their masterpieces and step fully into their lives.Today, in my work as a coach I see the tendency to present that veneer of polished competence in nearly every founder I meet. And while I recognize the need for presentation in some cases (fundraising, recruiting), I also see how that need to look good actually gets in the way of our learning and growth.If you're tired of doing your own impression of the "perfect leader," you're not alone.Shoot me a DM. There's another way. And it's fucking incredible.

Ryan H. Vaughn

Early in my career, I was hesitant to be direct with people. I didn’t want to come across as aggressive. I didn’t want to hurt feelings. I didn’t want to be “that guy.”

So I softened feedback.
I talked around the point.
I hoped people would infer what I meant without me having to actually say it.

It sounded thoughtful.
It felt kind.
And it created more confusion than clarity.

For a long time, I told myself this was generosity. What I eventually saw was that it was mostly fear.

Indirect communication often gets framed as “niceness.” But more often, it’s a way of trying to preserve connection without risking discomfort.

And that’s the paradox.

The key to influence isn’t niceness. It also isn't directness. It’s connection.

Directness only works when it happens inside connection.

Leaders tend to go indirect in the moments that matter most:

Difficult feedback
Missed expectations
Tension that’s been quietly building

In those moments, indirectness becomes a crutch - a way to avoid the risk of saying something true and potentially disrupting the relationship.

But people feel it anyway.

They notice the mismatch between words and tone.
Between praise and body language.
Between what’s said publicly and what’s felt privately.

Standards get fuzzy.
Expectations get unclear.
And psychological safety starts to erode.

Because no one actually knows where they stand.

Or, equally problematic, leaders are overpowering in their directness. Crossing the line into asshole territory, and leaving no room for the other person in the interaction.

This is equally problematic, as it equally erodes connection.

Real influence happens when you can stay in connection and speak truth into that connection.

That requires self-trust.

Learning to communicate directly isn’t just a communication skill.
It’s a developmental shift.

It means trusting yourself enough to stay present when things feel uncomfortable.

To say what’s true without withdrawing or armoring up.
To risk momentary tension in service of long-term trust.

As that fear loosens, you learn to stay in connection with another human within more and more intense conversations. Then, something interesting happens.

Directness stops feeling harsh. It becomes clean. Simple. Human.

If experimenting with directness feels uncomfortable, that doesn’t mean you’re doing it wrong.

It takes practice. The key is in monitoring how connected you are with the other person, while you speak your truth.

That’s where influence lives.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Exited founder turned CEO-coach | Helped early/mid stage startup founders raise over $500m, and create equity value over $12bn (and counting...)

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25 years building companies taught me that creating something meaningful is different than creating something successful.

Most people think meaning comes from getting somewhere.

A clearer vision. A bigger goal. A better version of themselves.

That belief creates tension.

Like a rubber band stretched tight between who you are today and who you think you’re supposed to become.

We praise that tension. We call it ambition.

And to be fair, it works.

It gets people out of bed. It builds companies. It produces results.

It also quietly guarantees dissatisfaction.

Because the moment you reach one version of the dream, it stops mattering.

It’s immediately replaced by the next one.

Not because you failed. But because the dream was never designed to end.

So the bargain most achievers make, usually without realizing it, looks like this:

Progress, momentum, recognition in exchange for contentment.

And we normalize this trade so completely that questioning it feels irresponsible.
Lazy, even.

Here’s what I've learned, working with dozens of founders in transition:

There are 2 fundamentally different ways to act.

1. Functional action

Doing things to get somewhere.
Action in service of an outcome.
Most work lives here.

2. Expressive action

Action taken not to become someone, but to faithfully respond to what’s true right now.

Not “What will this lead to?”
But “What feels honest in this moment?”

Expressive action doesn’t optimize for success.

It doesn’t guarantee status or promise outcomes.

It’s closer to art than strategy.

That scared me.

I worried that if I stopped chasing, I’d fall behind.

That everyone else would keep running while I stood still.

What I found instead was this:

When action comes from expression rather than ambition, there’s more energy, not less.

More precision. More aliveness.

You still work hard. But the work stops feeling like a toll paid on the way to a future life.

It is the life.

This is how you create something meaningful.

Not by aiming at meaning.

But by taking the action that feels most honest in this moment, without negotiating with outcomes.

Meaning is a byproduct of expressive action, never the goal.

This doesn’t mean ambition is wrong. Or that goals are bad.

It means if the only reason you’re moving is to escape the present moment, no amount of achievement will ever feel like arrival.

Meaning doesn’t come from becoming someone else.

It comes from doing what you’re doing as if it were art for its own sake, without needing it to justify your worth.

If this lands uncomfortably, nothing has gone wrong.

You may just be noticing that the ladder you’re climbing was never actually yours.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Once upon a time, I won $500k from a five-minute business pitch, but I still think the business pitch, as currently constructed, is leading investors to fund the wrong entrepreneurs...

I have a friend. Immigrated from a war zone in Haiti with his family. Served in the military with distinction. After becoming a civilian, he founded multiple businesses, including a few aimed at helping vets. I have some high-capacity friends, but this particular friend is a force of nature.

I got to witness him pitch to a couple of angels & seed investors a while back. 

He told his story, explained what he was raising money for, but even as he was pitching, I found myself getting confused. The pitch didn’t follow the format I’m used to, and as a result, it wasn't as clear as it could have been. I noticed this, so I wasn’t surprised when the investors told him he was too early. 

These investors, who will tell you until they’re blue in the face that at the seed stage they bet on the jockey and not the horse, unceremoniously turned down a force of nature because his pitch didn’t match the pattern they’re looking for. 

And it got me wondering: is the investor pitch really the best way to make an investment decision at the seed stage? 

If it really is about the jockey, and not the horse, shouldn’t our attention be on learning about the jockey?

Now I get it. A good presentation at the seed stage is indicative of someone who will be able to give a good presentation at later stages. This is important.

But this is also a learned skill. 

There is a “right way” to present your business, which I or any other experienced fundraiser could teach a young entrepreneur in an afternoon. It’s glorified paint-by-numbers.

At the seed stage, having a great pitch is compelling. But however compelling it sounds, the business is wrong. 

It’ll change a ton of times between then and any sort of exit, so having a good pitch really only proves that you know the combination lock to get investors excited. 

Instead, we should be looking for someone who can create their own path when there is no clear way forward. 

What if, instead of focusing our diligence on the fundamentals of a business that will change umpteen times, we asked entrepreneurs to tell their stories? 
What if we tailored the process to finding the best jockeys, knowing that we can train them to pitch to later-stage investors as we go?

The best entrepreneurs, invariably, have incredible stories from their lives, school, the military, previous companies, etc. Stories of amazing resilience in which they've overcome incredible odds. Learning about how a person has navigated these environments in their past will tell us more about their ability to do those same things than asking them to make up pretty-sounding shit.

If what we’re really looking for at the seed stage is good people, shouldn’t we design our vetting process around figuring out who it is, really, that is pitching us?

I'd love to hear your thoughts below.

Somewhere along the way, many of us lose the ability to pretend.

We stop softening our words.
We stop managing the room.
We stop spending energy trying to be palatable.

What once felt automatic starts to feel exhausting. And then, quietly, it stops working.

This is not bitterness. And it is not a personality flaw.

There is actually some interesting science behind it.

I recently read an article by Ellen Scherr that explored how, as we age, the brain reorganizes itself. Neural pathways tied to constant social monitoring and emotional labor get pruned. Energy becomes more precious. And the brain becomes less invested in managing how we are perceived. 

In simple terms, we become less compelled to please.

The article talks about women in particular, but I see this shift in the men I work with all the time. Founders in their 40s and 50s become more direct. They people-please less. They stop contorting themselves to fit rooms they have already outgrown.

And almost without exception, life feels more intense: More alive, Less numb.

Usually, they often become more effective too, because they are no longer self-limiting just to fit in.

A lot of my clients come to me wanting to trust themselves more and show up as more thoroughly themselves, with fewer filters in their lives.

That transition matters.

When people let go of those filters, everything sharpens. And in our work, we help people get to know themselves deeply enough to trust what wants to come through.

But there's another way this happens: Age

I see it in most clients as they grow older. They care less about what they used to care about, especially socially. They become more direct. They give less fucks.

There are ways to accelerate that. Inner work is one of them. But age is a very reliable indicator. Think of your nana, farting loudly in the middle of dinner and completely ignoring it. It's that sort of thing.

Now, you may not want to go around farting everywhere.

But letting go of all the subtle ways you limit yourself to fit in is, in my experience, unquestionably a happiness and effectiveness amplifier. 

When you stop checking whether you're acceptable and adjusting yourself in real time, you stop outsourcing your authority to the room.

This is not about becoming careless or abrasive. There's a difference between authenticity and unintegrated impulse. It's about reclaiming parts of yourself that were kept hidden primarily to keep the peace.

Age will eventually take you there. Inner work can take you there sooner.

Either way, the destination is the same.

 A life that feels less managed. Less split. More honest.

If this feels familiar, nothing has gone wrong. You may just be growing into yourself.

And that is not something to fix.

-

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

For most of my life, I had a very clear idea of who I was supposed to be. Then I discovered how to really live...

First, it was a professional basketball player.

I practiced constantly. Organized my life around it. Got the tattoos. I lived inside that identity.

And then that dream ended.

When it did, I didn’t stop to ask who I was without it.
I just found something else to become.

That next phase got darker. Drugs. Alcohol.
A few years of trying very hard not to feel the question underneath all of it.

Eventually, that identity collapsed too.
I ended up in jail after my second DUI.

So I did what a lot of people do at that point.

I decided to become someone better.

This was the late 2000s. Facebook and Twitter were just getting started. Startup founders were the new heroes. That seemed like a good thing to be.

So I became one.

I founded companies. Failed a couple times. Learned. Tried again. Built and scaled a venture-backed company over a decade. Raised money. Built a big team. Chased and eventually secured an exit.

And honestly, for a long time, it worked.

Until it didn’t.

A few years before I left that company, I started noticing how much energy it took to hold everything together.

Who I thought I needed to be for investors.
Who I thought I needed to be for employees.
Who I thought I needed to be for customers.

I was constantly managing the room. Constantly performing the role.

At some point, that just became unsustainable.

When I finally stepped away, a question landed that felt bigger than any business problem I’d ever faced:

If I’m not the CEO of this company anymore... who am I?

My reflex was the same one I’d always had.

Start something new.
Build the next thing.
Reconstruct the identity.

But this time, I didn’t.

Instead, I sat in the discomfort of not knowing.
No title. No pitch. No clean story about what was coming next.

People kept asking, “So what’s next?”

And for a long time, I genuinely didn’t know.

That was uncomfortable.
And humbling.

But something interesting happened in that space.

When I stopped trying to become anything, things started emerging on their own.

I started writing again. Not strategically. Just honestly.

That writing led to conversations.
Those conversations led to coaching.
And eventually, to the work I do now.

None of it came from a master plan.
It came from listening.

Entrepreneurship taught me how to build companies.

Letting go taught me how to build a life.

I see this pattern constantly in founders.

They think the next level requires a sharper identity.
A clearer vision.
A stronger version of themselves.

Sometimes the work is the opposite.

Not becoming someone new, but undoing the person you think you have to be.

If the old story isn’t working anymore, nothing has gone wrong.

You might just be standing at the edge of something more honest.

And that’s not a problem to solve.

It’s an invitation.

Most “shitty co-founder relationships” don’t start that way. Here's how they actually go off the rails: They decay slowly.

Every time something matters to you, but you don't say it, "eh, no biggie. I'll let it go."

You’re taking on relational debt. Cruft.

Imagine communication like a pipe.
Early on, it’s clean, you can say anything.

But over years of working together:

Missed expectations
Unspoken frustration
Feedback you meant to give, but didn’t

A little gunk builds up each time you don’t speak.

Eventually, the pipe clogs.

Now you’re arguing about trivial things, when the real issue is years of unsaid truth.

Here’s what I’ve learned from being a co-founder multiple times, and from coaching hundreds of founders:

Hyper-effective companies are built on hyper-effective relationships.

And hyper-effective relationships require clearing.

Clearing the pipe takes a simple (and very hard) 3-step process:

1) Observe what’s true, inarguably

Facts + your feelings.
No stories. No interpretations. No blame.

2) Take 100% responsibility

Not because it’s all your fault but because ownership is the only place you can create change.

3) Commit to doing your part differently

Your commitments are the antidote to the environment you helped create.

Notice what’s missing?

No demand for an apology.
No score-keeping.
No forcing the other person to change.

When you fully own your side, one of two things happens:

• The relationship becomes clean and effective again
• Or it becomes obvious it can’t continue, without drama

Either way, the pipe is clear.

And clear communication is the foundation for whatever you build next.

If you're struggling with your cofounder relationship, comment "gimme gimme" to get the full, comprehensive strategy we share with clients.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Jim Carrey stood on the Golden Globes stage, a two-time winner, looking out at a room full of the most successful people on earth. What he said next is a valuable lesson to us all: 

“I am two-time Golden Globe winner Jim Carrey...
And when I dream, I don’t just dream any old dreams. No sir. I dream about being three-time Golden Globe winner Jim Carrey. 
Because then I would be enough. 
It would finally be true. 
And I could stop this, this terrible search. 
For what I know, ultimately won’t fulfil me.”

He was joking, but at the same time, he definitely wasn't.

This is the sacred, self-inflicted wound that drives every high-achiever.

It starts with a dream. And with the first whisps of the dream, the machine locks in, and the outcome is set.

You create details, bringing the dream to life. And the minute it's real, a tension is born: a taut rubber band stretching between the dream and you. 

The dream is always pulling. 

You feel this tension as the disappointing, unself-actualized side of yourself, which compels you to chase, to change today to conform to your vision for tomorrow. This tension propels you out of bed every day.

We deify this tension as ambition. We call it "making something of yourself." But in addition to propelling us, it permeates life with a generalized dissatisfaction that no amount of achievement can solve. The moment you attain a piece of your dream, it becomes irrelevant, overwhelmed by the necessity of attaining the next piece. If you attain the whole thing, your dream will have receded, sitting as far out of reach from your hard-won perch as it was at the start.

The bargain is this: to succeed in getting closer to my dream, I offer in trade my contentment, in full, and vow to never be satisfied. 

This is the trade many high-achievers make. They get the allure of the chase at the cost of the moment.

Chasing a dream translates roughly to "wishing things were different from what they are." Since they cannot possibly be, our perpetually unfulfilled wishes leave us wanting. The game of chasing an ever-receding mirage is a game you can't win. 

I see this most often with founders right after an exit, to whom I say:

If you can still convince yourself that building a bigger company will finally make you feel complete - considering the last exit didn't - then do it. It is by far the easier path. 

It’s just like Jim Carrey's "dream" of a third Golden Globe. 

But eventually, you realize that no exit is big enough to make you feel whole in a lasting way. 

That is the moment the real work begins. The work that leads you away from chasing achievements to feel complete, and into the actual work of your life.

That transition - from performer to person - is the most exciting part of what I do.

It’s when you finally stop searching. And start living.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

Most companies that implode, do so for the same reason.

I still remember the chair I was sitting in.

Brown leather. Boardroom.
Nine months after our Series A.

We were scaling fast, from 15 to 75 people.
Hitting numbers. Lining up a Series B.

An investor looked at the pitch deck I’d spent weeks on and said:

“This is garbage. No one will buy this. Change it.”

In that moment, my job as CEO was to push back. I knew that.

Instead, something else happened. Fear took over.

And it almost killed the company.

A wave hit my body first, heat in my chest, pressure, shame.
And suddenly I wasn’t a CEO in a boardroom anymore.

I was a kid, scared that if I didn’t comply, someone would leave.

So I did what fear told me to do. I changed the pitch.

The raise failed.
We closed a bridge round instead.
It took years to recover.

At the time, I told myself a clean story: bad advice, bad board dynamics, bad timing.

What I couldn’t see yet was the real cause.

Fear made the decision for me.

This is far more common in startups than we like to admit.

We rarely talk about fear directly. So it hides behind more respectable labels:

Perfectionism
Founder conflict
Execution issues
Being “off your game”
Tone problems

Different symptoms. Same root.

Fear is a reflex. And when it’s unexamined, it runs companies from the background.

I see this constantly now in founders I work with:

• Flinching in negotiations
• Avoiding hard conversations
• Over-polishing instead of shipping
• Defensiveness
• Burnout

All fear-based. Mostly unconscious.

So what actually helps?

1. See fear as a bodily experience, not a thought.
Fear shows up as sensation before it becomes story.

2. Name it directly.
Not “I’m off my game.” But “I’m scared right now.”

3. Wait to make important decisions until fear has subsided.

The ability to sit with discomfort until you can respond instead of react is a leadership skill.

And finally: talk about fear as fear. Unexamined fear becomes fate.

For founders, this isn’t optional inner work.

It’s a business risk.

Ignoring fear and hoping it goes away isn’t an acceptable strategy for technical debt or competition.

It shouldn’t be for leadership either.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Anxiety is the price of the life you were meant to live. James Hollis said that years ago, and I’ve found it to be painfully accurate.

If you’re building something new, stretching beyond who you’ve been, anxiety is inevitable. 

Not as a flaw. As a signal.

Most people treat anxiety like an enemy. Something to suppress, outrun, or eliminate. And when that doesn’t work, they assume something is wrong with them.

Usually, nothing is wrong.

Anxiety is your nervous system doing its job. It’s an alarm designed to pull your attention toward something that matters.

The problem isn’t anxiety. It’s our relationship to it.

When you resist anxiety, it tightens.
When you try to override it with logic, it gets louder.
When you numb it, you mute everything else too.

What actually helps is learning to interpret it.

Some anxiety is functional. It’s telling you to act. Make the call. Fix the problem. Adjust the plan. Once you do, it quiets down. Feature, not bug.

Other anxiety is patterned. Old. Installed early. Designed to protect you from hurts that are no longer present. That kind of anxiety doesn’t resolve through action. It resolves through feeling it fully. Listening to it all the way, until it has nothing more to say.

That’s the part most people avoid.

Because feeling anxiety fully takes courage. It requires slowing down instead of muscling through. Listening instead of fixing. Trusting that the emotion isn’t here to destroy you, but to show you something.

When you learn to work with anxiety this way, it stops running your life from the background. It becomes guidance instead of interference.

The irony is that the leaders who feel the most alive, most grounded, most effective aren’t the ones without anxiety.

They’re the ones who stopped fighting it.

---

Proud to coach with Inside-Out Leadership , CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

In 2014, Microsoft was stagnant after years of success. Then, Satya Nadella took over and did the opposite of what most CEOs do: he didn’t start with strategy, he started with psychology...

For years the stock essentially wouldn’t move.
Key markets, like mobile and early cloud were slipping away.
Internally, teams were siloed.
Competition inside the business was rewarded more than collaboration.

The company wasn’t dying, it was stagnating.

Most leadership plays at moments like this start with strategy:

New products. New org charts. New KPIs.

Nadella’s first move was quieter and much harder.

He called out the real problem:

Microsoft had become a “know-it-all” culture and needed to become a “learn-it-all” one.

That feels soft, but it isn’t.

A know-it-all culture is driven by fear:

• Fear of being wrong
• Fear of losing status
• Fear of admitting uncertainty

That fear doesn’t show up as panic. It shows up as silos.

Avoiding hard conversations.
People optimizing for brilliance over learning.

That wasn’t a strategy problem. It was a psychology problem.

So he started inside.

He modeled curiosity instead of certainty.
He rewarded leaders who learned and collaborated.
He made it safe to say “I don’t know” and ask better questions.

He didn’t just change culture, he changed how leadership worked.

The result?

Microsoft regained relevance.
Cloud became a core growth engine.
And the company went from a decade of stagnation to becoming one of the most valuable companies in the world.

But that’s not the real lesson.

Leadership breakdowns rarely start as strategy problems. They start as fear-driven behavior patterns.

Fear doesn’t announce itself as fear.
It shows up as:

“We need more certainty.”
“That’s not how we’ve always done it.”
“We’re right and they’re wrong.”

Those aren’t causes.
They’re symptoms.

Nadella began with the psychology under the surface:

• how people relate to uncertainty,
• how they protect identity,
• how they choose learning over armor.

Most leaders try to fix outcomes.

The best fix themselves first.

That’s where real transformation begins.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Step 7, The Postcard: The primary risk to any intentional change is inertia. Specifically, that your best intentions get lost within the never-ending sea of life/work/family tasks, and before you know it, another year has passed... 

Don’t let that happen.

Create accountability for yourself, to yourself, by writing a letter to your future self, which you’ll schedule to have automatically delivered at a future date.

This way, whatever happens in the year ahead, you know that at some point in the future you will be reminded of your commitments, and have occasion to reflect on how well you kept to them (remembering that the key is keeping to actions taken, not outcomes produced).

In this letter, share your reflections from these exercises, your learnings, and any commitments you are making to yourself.

Schedule the email to send to yourself on June 30, 2026, using your mail client’s “Schedule Message” feature. 

And with that, brings the close to my annual reflection template.

------------

This is it.
This year.
This minute. 
This moment.

Even if it seems like this couldn’t possibly be it. 

That feeling is it, too.

Thank you for everything you brought to the world in 2025, for everything you are, and for everything you are becoming. 

Thank you for taking the time to reflect on your one weird, precious life, and by doing so giving yourself the opportunity to create it more consciously. 

Thank you for being unabashedly you, and not anyone else.

There will be a lot of moments in 2026. Co-create them with the ones you love.

I wish you the best of luck in diving deep, leading authentically, and bringing your unique story to the world this coming year.

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

There’s a moment in leadership that doesn’t get talked about much - when the role that once fit you perfectly starts to feel heavy.

Not wrong.
Not broken.
Just no longer yours.

Most people interpret that feeling as something to fix. 

Recommit. Push harder. Find the motivation again. 

After all, this role worked once. It made you who you are.

But sometimes what’s happening is simpler, and harder to accept.

You’ve changed.

Most leaders don’t leave roles because they fail at them. They leave because, quietly, the role no longer matches the person they’re becoming.

Howard Schultz is a useful example of this.

He built Starbucks. For a long time, he was Starbucks. The company’s culture and story were deeply personal to him. When he first stepped away as CEO, it wasn’t because the company was broken. It was because the role no longer fit.

Years later, he returned. The company needed him, and at that moment, he was the right person again.

And then, later still, he stepped away once more.

That second departure is the interesting one.

It wasn’t driven by crisis or failure. It came from something quieter. A recognition that staying would mean clinging to a version of himself that no longer felt true.

Most founders struggle here.

They stay in roles long after they’ve outgrown them, not because they’re incapable, but because their identity hasn’t caught up. The company becomes a proxy for self-worth. Letting go feels like disappearing.

But outgrowing a role isn’t failure.

It’s information.

It’s a signal that the work is changing, and so are you.

I see this often in my work. Leaders who are still performing competence long after it stopped being authentic. They’re not failing. They’re misaligned. And the longer they ignore that signal, the more brittle everything becomes.

Stepping away, when done honestly, isn’t quitting. It’s a form of stewardship. Of yourself, and often of the organization too.

The hardest part is trusting that who you are is bigger than the role that once defined you.

But that trust is exactly what makes the next chapter possible.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

I had to die three times before I finally got the hang of it.

The first was at 17.

I was convinced I’d be a professional basketball player. I practiced constantly. Built my life around it. That identity gave everything meaning.

And then it ended.

I didn’t know who I was without it, and I wasn’t willing to stay with that question.
So I numbed it.

Drugs. Alcohol. A few years of running hard in the wrong direction, until I found myself sitting on a stiff cot in a jail cell after my second DUI.

That version of me collapsed completely.

The second time, I responded the way our culture teaches us to.

I decided I could still be great, just as someone else.

This was the late 2000s. Startup founders were the new heroes. That felt like a worthy thing to become.

So I became one.

I founded companies. Failed a couple. Learned. Tried again. Built and scaled a venture-backed company over a decade. Raised capital. Built a large team. Eventually exited.

For a long time, that identity worked.

Until it didn’t.

When I finally stepped away from the CEO role, that identity died too.

But this third time was different.

Every other time an identity fell apart, I rushed to replace it.
New role. New story. New certainty to keep myself moving forward.

This time, I didn’t do that.

Instead, I stayed in what followed.

No title.
No plan.
No clean answer when people asked what was next.

It felt like standing on a plateau, between where I’d come from and wherever I might go next. The old story was gone. The new one hadn’t arrived.

A liminal space.

In the past, I treated moments like this as problems to solve.
Something to fix as quickly as possible.

This time, I let it be unfinished.

That space was uncomfortable. Disorienting. Quiet.
And unexpectedly, it was also the most alive I’d felt in years.

Without an identity to perform or defend, I started noticing what actually had energy. Writing. Honest conversations. Work that emerged instead of being forced.

Not from a master plan.
From listening.

Every major transition creates this in-between moment, when who you were no longer works, and who you’ll become isn’t clear yet.

Most of us rush to close that gap.

But there’s another way through it.

Not by recreating yourself.
Not by rushing to certainty.
But by staying with the space long enough for something truer to surface.

That’s what the third death taught me.

Not how to become someone new.

But how to stop interrupting the moment where life is trying to show you who you already are.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Michael Phelps won 28 Olympic medals across four Games. Yet, after London 2012, despite winning six medals, he was in deep crisis and contemplated ending his life...

He's not alone. Will Smith has talked about "Cliff Top" being just as lonely and hard as "Rock Bottom." Jim Carrey has said similar. The list goes on.

So what's going on?

This is a central paradox of high performers in any field. The fierce drive that propels you to the top of your game/market is the same corrosive force that leaves you hollowed out at the summit. For founders, we chase the exit unquestioningly, so focused on attaining the goal that we never stop to consider what might come after.

What nobody tells you about an exit is that the leaving is its own special kind of challenge. Special, and yet surprisingly consistent from person to person.

Here's the typical process:
1. Exit.
2. Existential vacuum.
3. ???
4. Realigned to purpose.

Some founders, confronted with this vacuum of purpose, jump immediately into the next thing. If you exit your consumer app and can find purpose in an even bigger consumer app, bless your heart, please run with everything you've got. Come read this post back after your next exit. 

If you find yourself struggling, however, know that you're not alone. Many founders struggle with step 3. I did. I experimented, jumping into each project with the same gusto, but I kept finding that I couldn’t recapture that sense of unquestioning purpose. Try as I might, it just felt different.

The salient issue, I've learned after coaching dozens of founders through their post-exit transition, is that as we mature, the way we construct meaning changes. 

At first, we FIND purpose. But eventually, we must CREATE it.

Finding Purpose:

• Purpose is found in the world and brought into yourself.
• Meaning is derived from what, and how much, you get.
• Success is a function of the outcome achieved.

Creating Purpose:

• Purpose is found inside yourself and brought to the world. 
• Meaning is built from what, and how much, you give.
• Success is a function of the work done and the motivations behind it.

Phelps found his breakthrough by checking into intensive treatment in 2014.

He returned in 2016 to win five more golds in Rio, but he swam from a radically different internal foundation. He swam from love for the sport, not the desperate need for meaning. The achievement was the same, but his entire relationship to it had transformed.

Today, he has moved beyond the pool to create purpose as a vocal advocate for mental health. By sharing his struggle, he is building a meaningful life that a gold medal alone never could.

Only you can tell if it's time to start your own work. If so, here's a question for you to get started on your path to rediscovery:
 
How can your career be most useful to others?

In 2017, Uber lost its CEO, its reputation, and nearly its future - because the culture became toxic and turned against itself. I’ve been there, too, without the global brand, but with all the danger...

Uber's early success was fueled by aggression, speed, and internal competitiveness. These traits fueled their rise, but without emotional regulation or boundaries, they became catastrophic liabilities.

I've been in that pressure cooker.

Years ago, I scaled my company from 15 employees to 75 employees in nine months. Our corporate culture was completely unprepared for the stresses of such rapid scale-up.

I talk to founders every day who face the same dilemma. They do what successful people do: they try to fix it. They spend a fortune on consultants, off-sites, and "culture work."

Uber is the masterclass in this.

They hired a former U.S. Attorney General to write a 12-page report with recommendations, fired 20 people in one shot to signal 'change', and ditched their original values for a new list of corporate-approved principles.

But you can't fire or spend your way into a new culture. By pushing new cultural frames without acknowledging the current ones, you breed resentment and cynicism from those who see the culture for what it actually is.

To truly change your culture, first, you must stop trying to build the culture you want and start by looking at the culture you actually have. Only then, working from a foundation of what is, can you begin to make change.

Here's how:

1. Look Inside Your Company

Anonymous surveys are a great tool to understand how your employees view your culture. Anonymity is key.

A survey like this communicates to your employees that you understand the importance of culture and that you will presumably listen to what they say. However, if you take this route and do nothing to address the feedback, it can break trust. 

2. Look Inside Yourself

At some point in every entrepreneur’s journey, they realize that their company is a manifestation of themselves. This offers a shortcut: you can understand your corporate culture by understanding yourself.

Are you late to meetings? That’s your culture. Others are late, too. 
Do you hold yourself to the grindstone, sacrificing holidays to make more progress? That’s your culture. Others do that, too. 

While most entrepreneurs resist this, looking internally is the most reliable route to determine your culture. For those brave few, it’s best done with either a 360-degree survey, or a dedicated coach to help you see your blind spots.

Great. I’ve reconciled with my current culture, and I still don't like it. Now what?

Once you've identified how you're creating the culture you say you don't want, changing it is simple:

Step 1: Change yourself to live by the values you want the company to live by.
Step 2: Write the values you live by on the wall.

And if you’re wondering, yes, that’s what we actually did to transform our culture at speed.

Simple, yes.

But not easy.

I used to be a virtuoso of the "Founder's Glance." In 30 minutes, I could diagnose a hemorrhaging sales pipeline or a toxic board member with surgical precision. It took me 15 years to sharpen these instincts into a blade...

And then GPT-4 learned it all in an afternoon. 

For the modern founder, watching AI automate your "unique" expertise is far more than merely a professional crisis. It’s an existential punch to the gut. 

The standard advice is to pivot - to move from "knowledge" to "wisdom." We’re told that our value now lies in judgment, in knowing which fires to douse and which to let burn. There is some truth there, certainly. 

But here is the deeper rot that no one wants to name. 

Tying your worth to "wisdom" is just as brittle as tying it to knowledge. Because wisdom is still something you possess. It is an accumulation, a trophy case of experiences. And anything you possess can - eventually, inevitably - be taken from you. 

I grokked this the hard way in 2020. 

The day I signed the papers and officially ceased to be "Ryan the CEO," the armor evaporated. Without the title, the expertise, and the authority, I realized with a terrifying clarity that I had no idea who was left standing in the room. I had spent a decade building a masterpiece of a company, but I was a stranger to the person underneath it. 

The only foundation that cannot be automated is your Integrity. 

Not integrity as a corporate buzzword, but integrity as wholeness - the radical alignment between your deepest values and your daily actions. This requires two things that are infinitely harder than raising a Series A: 

1. Ruthless Self-Inquiry: 

Stripping away the inherited scripts of "unicorn status" and "disruptive growth" to find what you actually give a damn about when the world isn't watching. 

2. The Courage to Lose: 

The terrifying bravery to say "no" to the high-status investor or the lucrative exit because it doesn't match the shape of your soul. 

When I finally put down the Successful CEO costume, the world didn't end. 

It began. 

And I became a more integrated human being. 

Inside-Out Leadership was born from that wreck. We help founders find the floor that doesn't drop out when the technology changes. 

If you’re tired of being at war with an algorithm for your sense of worth, let’s talk. 

Shoot me a DM. There's another way.

🤖 My Maven course and AI practice copilot for Meta-style PS and AT interviews (www.benerez.com/copilot) 🔁 Insider Loops: Helping PMs ace their Stripe, Uber, Figma and DoorDash interviews (www.insiderloops.com) I've been a founder, joined three different startups as their first PM, and held senior PM roles at Meta and Attentive. After leading product &amp; design at Continuum, a marketplace for fractional executives, I now partner with early stage founders as an advisor and help PMs land their dream roles. My experience spans business models and stages: - Life360 (Series B+C consumer mobile)- Breathe (consumer mobile in mindfulness / mental health)- Breeze/Canvas (Series A + acquisition automotive consumer, fleet management)- Abstract (Series B+C B2B SaaS for design teams)- Facebook (post-IPO SMB advertiser guidance)- Attentive (Series E marketing tech)- Continuum (Series A fractional executive talent marketplace)- Lettuce (Seed + Series A fintech for solopreneurs) 

Ben Erez

✨ We're LinkedIn official✨ Happy to share that I’m starting a new position as Co-Founder at Insider Loops alongside Marc Baselga!

Here's how you can think about Insider Loops: if you hired someone to interview PMs and successful PM candidates at your target company on an ongoing basis, and then asked those people to deliver their findings in a beautiful, frequently-updated guide...

That's us. And our guides are those findings.

We started with Stripe, DoorDash, Uber, and Figma and are heads down on the next set of guides for the hottest companies hiring PMs.

This requires a lot of unsexy research and synthesis every week but hey, Marc and I weirdly love doing unsexy things that are valuable.

We've sold way more guides than we expected in Q4 and early testimonials are live on our site. We've even had our first repeat customer who bought one guide and then came back and bought another!

As far as we know, there's nothing like this on the market. And there's nobody I'd rather be building with than Marc. 

Here's to a banger 2026 🚀

I help PMs ace interviews at Meta, OpenAI, Stripe, DoorDash + | Ex-Meta | 3x first PM | Advisor

This might be the worst candidate experience story I’ve heard in years.

I recently helped a PM prepare for interviews at an extremely hot company.

Over ~3 months, they invested 40+ hours into the process: take-home, panel presentation, multiple recruiter syncs, several follow ups with future teammates and executives, you name it.

They made it to the very final round. 

They met with the Chief Product Officer. Twice.

They were explicitly told that references would only be checked if the company was moving to an offer.

The company ran a reference check. With a current teammate, who strongly vouched for them.

Then... the company PASSED. No offer. Brutal.

The feedback? The CPO “didn’t like them enough.”

Now the candidate’s current team knows they’re exploring. There’s no offer in hand. Complete waste of time and energy.

This is one of the most despicable candidate experiences I’ve ever seen.

Running backchannel references against a candidate’s current teammates without consent is reckless. Doing it after telling the candidate the opposite is worse.

I’m tempted to name the company and publicly shame them. I won’t.

But if you’re a hiring leader reading this, know that stories like this travel fast. And they absolutely shape who will and won’t trust you with their career.

Our podcast took almost a year to get the first 10k downloads.
It took 3 months to get the next 10k downloads.

2 months to get the next 10k.
1.5 months for the next 10k.

Our last 10k downloads took 2 weeks.

Consistency and quality over time is everything.

The key to consistency is having fun and of course, working with a machine like Marc Baselga. We also get help from an incredibly talented person named Tehreem on Marc's staff at Supra.

Quality is where taste comes in. Marc and I have made hundreds of changes to the podcast over the past two years, each one improving some aspect of the experience by 1%. It adds up.

Many of our guests have gone on tons of other podcasts and tell us that ours was their favorite.

We're just getting started 🚀

Here are 10 predictions for how PM hiring will change in 2026 👇

𝟭. 𝗝𝘂𝗱𝗴𝗺𝗲𝗻𝘁 𝗮𝗻𝗱 𝘁𝗮𝘀𝘁𝗲 𝗯𝗲𝗰𝗼𝗺𝗲 𝘁𝗵𝗲 𝘁𝗼𝗽 𝗾𝘂𝗮𝗹𝗶𝘁𝗶𝗲𝘀 𝗲𝘃𝗮𝗹𝘂𝗮𝘁𝗲𝗱 𝗶𝗻 𝗣𝗠 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝘀
As AI handles more of the heavy lifting, interviews focus less on output and more on what candidates choose to build and how deeply they can critique existing products (taste).

𝟮. 𝗘𝘅𝗽𝗲𝗿𝗶𝗲𝗻𝗰𝗲 𝗲𝘃𝗮𝗹𝘂𝗮𝘁𝗶𝗻𝗴 𝗔𝗜 𝘀𝘆𝘀𝘁𝗲𝗺 𝗽𝗲𝗿𝗳𝗼𝗿𝗺𝗮𝗻𝗰𝗲 𝗯𝗲𝗰𝗼𝗺𝗲𝘀 𝗮 𝗺𝘂𝘀𝘁-𝗵𝗮𝘃𝗲 𝗳𝗼𝗿 𝗔𝗜 𝗣𝗠 𝗿𝗼𝗹𝗲𝘀
Building golden eval sets and operationalizing AI feedback loops becomes table stakes, whether teams train models or consume foundation model APIs.

𝟯. 𝗣𝗠 𝗵𝗶𝗿𝗶𝗻𝗴 𝘄𝗲𝗶𝗴𝗵𝘀 𝗱𝗼𝗺𝗮𝗶𝗻 𝗲𝘅𝗽𝗲𝗿𝗶𝗲𝗻𝗰𝗲 𝗵𝗶𝗴𝗵𝗲𝗿 𝘁𝗵𝗮𝗻 𝗲𝘃𝗲𝗿
As teams internalize how hard AI evaluation actually is, they favor PMs with deep domain intuition who can spot failure modes quickly.

𝟰. 𝗣𝗠 𝗷𝗼𝗯 𝗱𝗲𝘀𝗰𝗿𝗶𝗽𝘁𝗶𝗼𝗻𝘀 𝗮𝗿𝗲 𝗲𝗳𝗳𝗲𝗰𝘁𝗶𝘃𝗲𝗹𝘆 𝗳𝗼𝗿 𝘀𝗲𝗻𝗶𝗼𝗿 𝗣𝗠𝘀 𝗼𝗻𝗹𝘆
Junior PM roles disappear from career pages and get filled through internal transfers, leaving PMs with less than 3-5 years of experience under-qualified on paper for nearly every JD.

𝟱. 𝗧𝗵𝗲 𝗴𝗲𝗻𝗲𝗿𝗮𝗹𝗶𝘀𝘁 𝗣𝗠 𝗵𝗶𝗿𝗶𝗻𝗴 𝗹𝗼𝗼𝗽 𝗱𝗶𝗲𝘀
“Approve for hire first, match later” stops working, and PMs are only interviewed for clearly defined roles with explicit mandates.

𝟲. 𝗖𝗼𝗹𝗱 𝗮𝗽𝗽𝗹𝗶𝗰𝗮𝘁𝗶𝗼𝗻𝘀 𝗱𝗶𝗲 𝗳𝗼𝗿 𝗿𝗲𝗮𝗹
As each JD attracts hundreds or thousands of applicants, hiring shifts almost entirely to referrals, proof-of-work inbound, and targeted outbound.

𝟳. 𝗔𝗜-𝗻𝗮𝘁𝗶𝘃𝗲 𝘀𝘁𝗮𝗿𝘁𝘂𝗽𝘀 𝗵𝗶𝗿𝗲 𝗣𝗠𝘀 𝗮𝗳𝘁𝗲𝗿 𝗶𝗻𝘀𝗶𝘀𝘁𝗶𝗻𝗴 𝘁𝗵𝗲𝘆 𝗱𝗼𝗻’𝘁 𝗻𝗲𝗲𝗱 𝘁𝗵𝗲𝗺
Once these companies scale, someone has to own prioritization, tradeoffs, and decision-making and the PM role becomes unavoidable.

𝟴. 𝗕𝗶𝗴 𝗧𝗲𝗰𝗵 𝗣𝗠𝘀 𝘀𝘁𝗿𝘂𝗴𝗴𝗹𝗲 𝘁𝗼 𝗯𝗿𝗲𝗮𝗸 𝗶𝗻𝘁𝗼 𝗵𝗼𝘁 𝗔𝗜 𝗰𝗼𝗺𝗽𝗮𝗻𝗶𝗲𝘀
Stock-inflated compensation collides with a higher bar for AI judgment, making many PMs feel overpriced and under-skilled unless they’ve worked directly on AI products.

𝟵. 𝗦𝗲𝗻𝗶𝗼𝗿 𝗜𝗖 𝗣𝗠 𝗰𝗼𝗺𝗽𝗲𝗻𝘀𝗮𝘁𝗶𝗼𝗻 𝗵𝗶𝘁𝘀 𝗮𝗹𝗹-𝘁𝗶𝗺𝗲 𝗵𝗶𝗴𝗵𝘀
As each PM is expected to drive more leverage, hiring teams compete aggressively for a smaller pool of top-tier talent, driving up demand & price.

𝟭𝟬. 𝗣𝗠 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝘀 𝗲𝘃𝗮𝗹𝘂𝗮𝘁𝗲 𝗔𝗜 𝗳𝗹𝘂𝗲𝗻𝗰𝘆, 𝗯𝘂𝘁 𝗶𝘁 𝘄𝗼𝗻’𝘁 𝗯𝗲 𝗽𝗿𝗲𝘁𝘁𝘆
Interview loops split into two buckets: building AI products vs using AI to build products, and struggle to fairly assess the first due to limited internal experience.

Did I miss anything?

Our podcast passed 100k downloads this week. Here's why I think it's working:

Marc Baselga and I started the Supra Insider podcast almost two years ago with the goal of bringing product leadership conversations from within the Supra community to a wider audience. 

We've published an episode every week since March 2024. We only missed two weeks ever. Episode 100 airs in a few weeks. 

We've made hundreds of updates to the podcast since its inception: branding, project management, guest outreach, editing, titles, pre-episode guest comms, etc. It all matters.

We've talked to many podcast growth experts and keep hearing the same thing: the key to growth is content quality and consistency. If we can do that for long enough, we'll grow.

Reaching 100k downloads feels like the perfect moment to reflect and try to unpack what's enabled us to be so consistent while improving the quality:

1) we have fun and don't take things too seriously - podcast recording slots are Marc and I's favorite items on the calendar every week

2) we only invite guests if at least one of us is extremely excited about them and prioritize the guests we're most excited about

3) we pick interesting "trailheads" for every episode and go off-roading by letting our curiosity pull us

4) we keep the lift for guests minimal; no pre-recording syncs, scripting, or prep work beyond trailhead selection (<2 hrs total time commitment including everything)

5) we trust that the more present we are in the conversation, the more engaging the episode will be for the audience

6) we aim for each episode to feel like a conversation between three friends who are learning from each other - the guest is an equal owner of the conversation

7) we don't delegate anything we don't do first ourselves - we have an incredible teammate named Tehreem who helps us run the podcast

8) we aim to make episodes that guests will genuinely want to promote and believe a world-class guest experience is a growth driver

9) we believe in making the podcast 1% better every week - the score takes care of itself

10) we treat the podcast as the energy source for everything else we do

Last but certainly not least: Marc. Marc is the key to our consistency. The guy is an operational savage. I admire his discipline and his ability to create systems that hold him (and now me) accountable to necessary behaviors and tasks.

The podcast is a well-oiled machine because of Marc's executional rigor. He makes me better every day. 

Super grateful to all of our incredible guests over the last two years and all the people who bring us along for their commutes, gym sessions, laundry-folding and dish-washing and dog-walking, etc. We appreciate you.

It feels like we're just getting started. Here's to the next 100k downloads 🚀

3,600 people signed up for a recent session I hosted about how to get noticed by PM hiring managers in 2026.

Nearly 600 people showed up live!

This tells you a lot about the PM job market right now.

The old playbook is breaking down, with resumes, cover letters, and cold outreach not cutting through the noise like they used to.

If you’re feeling stuck in this market, you’re not imagining things. The bar has shifted, quietly and meaningfully.

Hiring managers are overwhelmed with seemingly qualified applicants, but aren't seeing the perfect fit. 

They're looking for something very particular: PMs who have very relevant experience AND an ability to throw out what worked in the past because things are changing rapidly. 

In a world where "on paper" qualification is table stakes, the very way *you get noticed as a candidate* is itself a differentiating signal about how you might show up *on the job*.

So how can you actually stand out?

In our 1-hour session, I dove into this with two incredible product leaders who have been deeply engaged in PM hiring for the last few years:

Nickey Skarstad​, Director of Product at Duolingo
Hilary Gridley, former Head of Core Product at WHOOP

Some of the main topics we covered: 

↳ Why the old playbook (generic resumes, cold outreach, etc) is breaking down as AI lowers the effort to meet the old quality bar
↳ What hiring managers actually respond to today: relevance, judgment, effort, and proof that you can do the job.
↳ How cold outreach still works, but only when it feels human, specific, and framed as an offer rather than an ask (bonus points if you can make them smile / laugh)
↳ Why building in public (writing, prototyping, experimenting) increases your surface area for luck and serendipity
↳ How referrals still matter, but only when they’re truly warm and easy to forward
↳ Why doing “too much” is rarely the problem - most candidates don’t do enough

The energy in the Zoom chat made it clear how important this moment feels for a lot of PMs and I'm glad we could offer a shared space to learn together.

We also resolved my accidental confusion about the Duolingo owl being a parrot (it is, in fact, an owl 🦉)

And I think we reached consensus that socks belong in slippers 🧦.

🎥 The recording is now available for anyone who couldn’t make it to the live event: https://lnkd.in/ebDi4UBr

“I’m afraid of hiring a PM who interviews well but collapses under real ambiguity, slows the team down, and costs me months to unwind.”

This is a real quote from a series B 
PM hiring manager who I recently talked with about their interview process for the latest PM hire. 

I found it fascinating that this hiring manager was not as concerned with skill evaluation as they were with 
(1) clock speed/velocity and 
(2) ability to execute confidently in the face of ambiguity

Another big takeaway for me was that the hiring manager didn't make these two dimensions explicit to the candidate in the interview process. 

Instead, they were evaluating these throughout the process, at every step.

A specific example is that weaker candidates asked a lot of clarifying questions about the assignment, whereas the person they ended up hiring just made a bunch of assumptions that were well-reasoned to unblock themselves.

This behavior pattern from the person they hired demonstrated both comfort with ambiguity in the form of making assumptions, but also a desire to optimize for speed by not slowing down to ask clarifying questions.

I have a lot more of these conversations with PM hiring managers lined up and I'm excited to keep sharing what I learned about what's important in this market!

"DoorDash is the kind of place where PMs are expected to go cry in the bathroom and come back swinging."

When we were putting together the Insider Loops​ guide for DoorDash, we realized the company had a very particular culture. 

One way they screen for culture fit in their interview process is through the "Values" interview, where candidates are asked about a big failure.

DoorDash interviewers hold a high bar and want to see four things in a failure story:

(1) The triage - raw version of the problem, your initial reaction, and how you actually operated when everything was on fire. 

(2) The hard call - which options were you evaluating, which tradeoffs did you make and why.

(3) The recovery - how did you correct the failure and what did you learn.

(4) The futureproof - which structural changes did you implement in the system so that the problem never happens again.

This matters because DoorDash has this culture where you're expected to take the punch, regroup quickly, and lead without hand-holding. 

A few things interviewers are grading:
↳ Bias for Action: how fast did you stabilize?
↳ Truth Seek: what data or customer evidence surfaced the problem?
↳ Ownership: how did you make all sides of the ecosystem whole (consumer, merchant, Dasher)?

^ these are all stated DoorDash company values anyone can read about online. Applying the values in interviews is key.

To show a brief example...

❌ Weak: "We missed the launch date, but I learned to build in more buffer time."

✅ Strong: "We missed the launch. That night I called the three merchant partners personally to reset expectations. By Friday I had a shared tracker in place so ops, eng, and BD saw the same timeline. We haven't missed a date since."

If you're preparing for behavioral interviews, make sure you internalize the company culture and values.

Your stories aren't about *you*. 

They're about why *you're the perfect fit* for the company and role.

Get the full DoorDash guide at www.insiderloops.com

Some of your best future PM hires already work at your company. They just don’t have the PM title (yet).

I keep seeing teams say they “can’t find strong PMs” in this market while defaulting to an external search for every opening. 

But what if the perfect PM hire isn't outside of your company?
What if they're already there?

Think about it. 

The main things hiring managers look for include:
↳ Deep domain understanding of the product and customer
↳ Good judgment about tradeoffs and execution
↳ Ability to influence XFNs
↳ An instinct for connecting customer problems to business outcomes

There are people at your company who have these - they're just not PMs.

These people can be easy to miss because they’re probably crushing their current (non-PM) role and busy getting stuff done.

In this week's episode of the Supra Insider podcast, Marc Baselga​ and I dove deep with Michael Chen​ into his experience making the switch from product marketing to product management within Asana and then to PM at DoorDash. 

What stood out to me about Michael's story was how he de-risked the move by framing it as an experiment.

He didn’t ask for a role upfront.
He didn’t wait to “feel ready.”
And he didn’t rely on a single moment or conversation.

Instead, he spent months working closely with product leaders, design, and engineering. He took on PM-like problems in his existing role. He built credibility in the domain. 

By the time there was an actual PM-shaped need, he was already doing the work. The role just caught up and he was the obvious choice for it.

Sometimes the best candidate is not even an option you're considering. But they're right under your nose.

If you want better PMs, look for behavior, not titles.

Your next great PM hire might already be one of your favorite teammates.

If you're considering an internal move into PM, or if you're hiring PMs and want some inspiration on how to think about recruiting one of your teammates, this conversation is for you.

Check out the full episode:

Spotify: https://lnkd.in/euVcUWKR
Apple: https://lnkd.in/evcyC-ne
YouTube: https://lnkd.in/eyBtRVDP
Substack: https://lnkd.in/eMf-wPZ5

Today is my daughter’s third birthday 🎂

She's at the age where real interests are emerging (the performing arts are definitely holding a special place) and we're starting to encourage sparks of passion and interest.

K-12 is right around the corner and before we know it, university will be looming. 

Will college still make sense for my three year old?

I'm excited to share a conversation we published today on the podcast with Stephen Cognetta (co-founder of Exponent Interview Prep) where we dove deep into the future of higher education and it's relationship with the job market. 

This episode was a full-circle moment for me. Back in 2020, when I was preparing for my Facebook PM interviews, I spent an embarrassing number of hours watching Exponent's mock interviews on YouTube. 

I genuinely don’t think I'd land my FB offer without Exponent.

Stephen sits at a really interesting intersection. He runs the leading interview prep platform for tech professionals, teaches at Northeastern, sells to universities, and does executive coaching.

He highlighted that these days many first year students come in with immediate goals around figuring out their plans to land a job when they graduate.

But universities are not particularly good at job placement and they're getting even worse. So what are they good for?

For me, college was an incredible container for self-discovery and fun (time to explore, exposure to new ways of thinking, being surrounded by people who stretched how I saw the world, etc). I wouldn’t trade my time at the University of Florida for anything.

But I keep wondering about a different kind of student:
- Someone who isn’t especially interested in the “college experience”
- Someone who mostly wants a job
- Someone who’s pragmatic, motivated, and outcome-oriented

^ For that person, I’m less convinced the traditional university path delivers the value it promises. 

If the goal is employment, the reality is that students need to develop real skills the market values and get good at telling that story in interviews / getting someone to bet on them.

They don't need courses, degrees, and certificates. They need experience.

I'd love to see universities redesign themselves as experiential learning environments where students can get reps developing the skills employers value.

But I think we have a long path ahead. 

Will college be right for my daughter? I suppose it'll depend on her goals, options, priorities, etc. I'll encourage her to explore whichever environments seem to be the best fit. 

I'm sure we'll cross that bridge when we get there.

For now, I'm going to enjoy having a three year old whose biggest concern is not having enough Disney princess dresses. Happy birthday, Gaia ❤️

🎙️ Check out the full conversation with Stephen

Spotify: https://bit.ly/4qrrwXi
Apple: https://bit.ly/3NxzLlT
YouTube: https://lnkd.in/eVR5ck84 
Substack: https://bit.ly/4qrrCy8

Most PMs applying for roles are doing 𝘮𝘰𝘳𝘦 to stand out, when they should be going for 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵.

More applications.
More cold DMs.
More resume tweaks.

And for a lot of people it’s not working.

But the PM job market in 2026 isn’t broken.

It's just... different.

Tomorrow I’ll be hosting a free live session with two incredible product leaders who are super experienced hiring managers, Nickey Skarstad​​ (Duolingo, Airbnb, Etsy) and Hilary Gridley​ (WHOOP, Dropbox, Nike).

In our session, How to get noticed by PM hiring managers in 2026, we’ll break down:

✍️ Why old PM job search playbooks no longer work
✍️ What “real signal” looks like to hiring managers in 2026
✍️ What actually cuts through the noise to get noticed

This is for PMs who feel like they’re doing everything “right” and still not getting traction.

📅 Thursday, Jan 22
⏰ 2:00pm ET
📍 Live on Zoom
💸 Free

If you’re actively interviewing or planning to later this year, this session should recalibrate how you show up. 

Can't join live? Sign up and get the recording over email.

👉 Sign up here: https://lnkd.in/g-s-CuDC

PS. This isn’t about hacks or resume tricks. It’s about aligning your effort with how hiring managers actually evaluate PMs today.

Magic happens when you hate your own product while your customers deeply want it and are investing in improving it.

One of the defining characteristics of great product builders is that they live in a state of continual dissatisfaction with their product.

Hell, great builders can often rant for hours about the problems with the entire market/ecosystem around their product.

Many of these builders run hyper-successful companies and incredibly fast-growing products.

Yet, they look at the current state of their product/company and think "this sucks and I know we can do so much better".

And they're ALWAYS right. 

What's interesting is that customers aren't blind to the problems. They'll even point out all the issues with a product and why it sucks. And despite the criticism, keep using it avidly and recommending it.

So why do customers look past the problems?

I believe it's because they see something special in the product. It glitters and inspires them to imagine a much better product. There's a seeming inevitability to the changes that need to be made. 

The key is that the customer sees the changes as belonging in *this product*, not another product.

The combination of promising spark and inevitability creates an obviousness that emotionally drives the customer to engage with the builder by suggesting specific improvements. 

Smart builders will engage with those customers to deeply understand them, incorporate the philosophy into the product, and this virtuous cycle mints a true winner. 

Just look at Figma, Linear, and Gamma. Delightful products with real magic. 

Yet, I bet the founders are still deeply dissatisfied with the current state of their products. And I'm sure they're hearing it loudly from customers every day. 

Yet... their charts are all up and to the right.

Whenever I feel frustrated with my own products, I tell myself: this is fuel. 

If I looked at my product and thought, "wow that's actually in pretty good shape"... it's basically game over.

If you're a builder and hate your product, I'll say two things to you:
1) You're in good company
2) Now go make your product better

A surprising number of strong PM candidates turn down free help from recruiters during interviews.

I recently heard this from Anneli Scopazzi, a recruiting leader who’s helped scale teams at places like Palantir, Figma, and Notion. 

She said when recruiters offer prep calls or guidance, many candidates (even experienced ones) don't take them up on it.

This fits with something I've noticed talking to successful candidates who landed offers at companies like Stripe and DoorDash while building our Insider Loops guides: successful candidates nearly always talk about how helpful the recruiter was to them.

Not just polite or responsive but actively helpful: Sharing context, offering prep, flagging where others struggled, etc. Anything to help them understand what “good” looks like in that specific loop.

If you’re a strong candidate, an internal recruiter is usually not sitting across the table from you. They’re sitting next to you. Their job is to make a quality hire quickly. 

Once you clear the initial screen, they’re incentivized to help you succeed, not catch you messing up.

This means the recruiter screen isn’t just a filter. It’s an opportunity to earn an advocate.

Some candidates keep recruiter conversations transactional. Answer the questions, smile, say thank you, dance the dance.

Others treat them as a partnership. They ask how to prepare well. They try to understand what success looks like in this process. They actually try to use the recruiter as a resource.

Those candidates inevitably show up more confident to interviews, making less mistakes and ultimately getting pushed forward behind the scenes.

This isn’t about gaming the system. It’s just good product instincts applied to hiring:
↳ Don’t guess when you can ask
↳ Reduce ambiguity early
↳ Get feedback before it’s too late

So here’s the question I keep coming back to:

Do candidates succeed because some recruiters are more helpful?
- OR -
Are recruiters inherently helpful when candidates actually take them up on it?

Either way, don't sleep on the recruiter relationship. It can literally be the difference between an offer and a pass.

If you're exploring new roles in 2026 and want to get the full rundown of how to leverage a recruiter to your advantage, check out our recent episode of the Supra Insider podcast with Anneli. It's full of gold.

Spotify: https://lnkd.in/ejq-Fh6p
Apple: https://lnkd.in/eDee7FtQ
YouTube: https://lnkd.in/eZNJrYg2
Substack: https://lnkd.in/eTz5B7z6

Uber's PM interviews are designed to see how you handle chaos and constant interruptions. 

When we were putting together the Insider Loops​ ​guide for Uber, we realized the company had a very particular interview style. 

Here are 6 things I find interesting about their PM interview process:

𝟭) 𝗧𝗵𝗲 𝗵𝗶𝗿𝗶𝗻𝗴 𝗺𝗮𝗻𝗮𝗴𝗲𝗿 𝘀𝗰𝗿𝗲𝗲𝗻 𝗵𝗮𝘀 𝗼𝗻𝗲 𝗵𝗶𝗱𝗱𝗲𝗻 𝗴𝗼𝗮𝗹

They're assessing whether you'll survive the jam. If they don't think you can handle pressure, you're out before you start.

Talk about how you thrive in chaotic environments and have been told you're great at handling curveballs.

𝟮) 𝗬𝗼𝘂𝗿 𝗛𝗠 𝗶𝘀 𝗯𝘂𝗿𝗻𝗶𝗻𝗴 𝘀𝗼𝗰𝗶𝗮𝗹 𝗰𝗮𝗽𝗶𝘁𝗮𝗹 𝘁𝗼 𝗯𝗿𝗶𝗻𝗴 𝘆𝗼𝘂 𝗼𝗻𝘀𝗶𝘁𝗲

They personally recruit every interviewer for your loop. There's no central pool and they're calling in favors with busy peers.

This means if you made it to the Jam, the HM is already in your corner. Treat them with gratitude. 

𝟯) 𝗧𝗵𝗲 𝗝𝗮𝗺 𝗶𝘀 𝗳𝘂𝗹𝗹 𝗼𝗳 𝗶𝗻𝘁𝗲𝗿𝗿𝘂𝗽𝘁𝗶𝗼𝗻𝘀 𝗮𝗻𝗱 𝘁𝗵𝗮𝘁'𝘀 𝘁𝗵𝗲 𝗽𝗼𝗶𝗻𝘁

You'll get derailed within the first 5 minutes. This is intentional. They're testing if you can handle chaos while staying composed.

Knowing this changes everything - the curveballs aren't you failing, they're the actual evaluation. Incorporate new inputs into your story and keep moving forward.

𝟰) 𝗬𝗼𝘂𝗿 𝗝𝗮𝗺 𝗮𝗿𝘁𝗶𝗳𝗮𝗰𝘁 𝘁𝗿𝗮𝘃𝗲𝗹𝘀 𝗶𝗻𝘁𝗲𝗿𝗻𝗮𝗹𝗹𝘆

HMs share circulate impressive presentations to other teams even if the candidate is not the perfect fit for their team.

If you're wrong for Team A but crushed the Jam, Team B might grab you.

One PM I know got rejected for the role they applied for, then got pulled into a better role because their Jam deck got forwarded.

𝟱) 𝗬𝗼𝘂'𝗿𝗲 𝗻𝗼𝘁 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝗶𝗻𝗴 𝘄𝗶𝘁𝗵 𝗿𝗮𝗻𝗱𝗼𝗺 𝗣𝗠𝘀 𝗶𝗻 𝘁𝗵𝗲 𝗼𝗻𝘀𝗶𝘁𝗲

Unlike many big tech companies, every Uber interviewer is from your future team/ecosystem.

They're asking themselves: "Would I want to work closely with this person?"

Treat these interviews as meetings with future collaborators.

𝟲) 𝗧𝗵𝗲𝗿𝗲'𝘀 𝗮𝗹𝗺𝗼𝘀𝘁 𝗻𝗼 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝗲𝗿 𝗰𝗮𝗹𝗶𝗯𝗿𝗮𝘁𝗶𝗼𝗻

Each interviewer gets specific guidance from the HM on what to look for, leading to massive variance in what "good" looks like.

Don't assume the interviewer is skilled. Over-communicate and read between the lines on what they're trying to evaluate.

Want more Uber insights? Get the full guide at www.insiderloops.com

The best operators are often the worst at marketing themselves.

I see this all the time with incredible PMs, founders, investors, etc.

Creating an impact requires a relentless focus with sometimes years of heads-down work. I call it the "impact cave". 

People in the impact cave are making hard decisions, putting out fires, and navigating tons of ambiguity. 

Their eyes are fixed on the prize.

And they don't talk about it publicly - the work will speak for itself... Or at least it used to. 

In 2026, if you pop out of your cave after 10 years of incredible work in the cave, nobody on the outside will know about you. 

Your personal brand will extend no further than your colleagues.

As far as the market is concerned, your experience didn't really happen - unless you tell us about it.

In contrast, picture the visible operator who shares publicly while getting stuff done. 

They will attract more inbound opportunities as the market rewards their perceived expertise. 

They're not better. They're just visible.

We dove deep into this dynamic on the latest Supra Insider episode with a rare world-class operator who is also great at sharing his expertise, Casey Winters​ (co-founder & CEO at SuperMe​).

In the episode, we talked about:
↳ Why meaningful expertise has quietly disappeared from public platforms
↳ How knowledge moved into private networks, and why that’s a real loss
↳ The difference between getting an answer and developing perspective
↳ How AI can scale access to judgment without replacing humans
↳ Why peer learning and trust now matter more than ever in career growth

This conversation isn’t about why operators need bigger egos or why we should all become content creators.

It’s about making your expertise available to others and being of service by sharing. People should know what you’re good at without having to sit next to you for two years.

I've been a fan of Casey's work for many years so this was a bit of a dream come true for me to have him join us on the show. So pumped to share this conversation.

Episode links:
Spotify: https://lnkd.in/eCq5-nZQ
Apple: https://lnkd.in/e3xADg7a
YouTube: https://lnkd.in/e9dn422J
Substack: https://lnkd.in/eSnD8Cyb

I keep running into the same debate lately: do moats matter early? Or do moats only matter once you’ve found product market fit?

There are two real schools of thought here.

One camp says moats don’t matter early; ship, find PMF, and worry about defensibility later once there’s something worth protecting.

The second camp says moats matter from day one; if you can’t explain why you’ll stay ahead, success just invites competition.

I've heard both views from equally smart people. I don't think it's black and white.

But in my mind the pendulum has recently been swinging more strongly toward the second view (a good story about moats early on).

We recently hosted Itamar Novick (founder and managing partner at Recursive Ventures) on the Supra Insider podcast and I see him as an unofficial spokesperson for the second camp. 

Itamar has been investing at the earliest stages for 15 years and has backed multiple unicorns. In our conversation, Itamar calmly framed the biggest risk with not having a compelling moat story:

If a founder can’t explain their moat early, they’re often setting themselves up to get commoditized the moment things start working down the road.

Here are some of the dynamics we covered in the convo:

↳ Building has gotten dramatically easier. With vibe coding, competing no longer means raising millions to hire a team. In many cases, it means one strong founder with the right tools.

↳ Product market fit without defensibility is fragile. The moment demand is proven, copycats show up. Market share fragments, margins compress, and momentum stalls before real scale.

↳ Incumbents are watching. They already have customer relationships, data, and distribution. Without a moat, you end up validating the market for them.

↳ The companies that tend to go all the way aren’t just early. They have some structural reason they keep winning as the category fills in.

This doesn’t mean you need a fully developed moat on day one (let's be honest, that's not realistic).

But you probably need a credible story about how you'll establish a moat so that your success doesn't kill you.

If you're a founder, the question Itamar is pushing you to consider is: "If your product starts working tomorrow, what makes it hard to clone next week?"

Check out the full conversation if you want to go deeper 👇

Spotify: https://lnkd.in/e5u3Z9Yy
Apple: https://lnkd.in/eF-A53Bz
YouTube: https://lnkd.in/eg5AF7dm
Substack: https://lnkd.in/eUAJXzup

The gold-per-minute is off the charts in Lenny’s recent ep w/ Matt MacInnis 🔥 

Coincidence that it’s also jam-packed with F bombs and BS drops? Maybeee.

Matt is the rare founder/CEO turned COO who, after watching Rippling’s R&D org struggle from the sidelines for years, raises his hand to take on the Chief Product Officer role, jumps into chaos and slays the dragon.

He said he was super naive in hindsight when criticizing PM and the best way to appreciate the product leadership job is to get your hands dirty on the ground. That 100% tracks.

Also, Rippling has every PM hire (regardless of seniority) tackle the same case study is fascinating to me as someone who studies interview design. 

They’ve intentionally structured the case so that every candidate feels like they failed it. 

The signal is in how far they made it before failing, the depth of insights they showed along the way, and how they respond to curveballs.

The other big interviewing insight is that hiring managers should not suppress their intuition (which some might call bias) but instead force themselves to articulate in words what their intuition is telling them about a candidate.

There’s a story about an incredible candidate who just left him *feeling* like it’s just not the right fit. But he wrestled with putting it into words.

He realizes the candidate is an A+ beta minimizer when they needed an A+ alpha maximizer. Ding ding.

This is what it looks like to think intentionally about hiring.

If you’re an executive looking to understand product leadership and/or just leveling up as a clear thinker, this episode is straight fire.

Domain expertise won't move the needle in Stripe's generalist interview loop. 

I've watched security-focused candidates with deep infra and compliance knowledge get grilled by PMs from growth, platform, and revenue. None of them understood or cared about security.

In some interviews, domain expertise plus strong execution gets you through. But at companies like Stripe, the interview evaluation works differently.

Stripe interviewers value candidates who communicate clearly across domains while demonstrating strong PM fundamentals.

❌ Weak candidates lean on domain depth:
"In my security work, we handled compliance through..."

[Interviewer thinking: I don't evaluate security products. How do I score this?]

✅ Strong candidates build portable frameworks:
"Let me walk through my prioritization approach. I start by understanding the business impact, then evaluate technical feasibility, and finally assess user value. Sound good?"

[Interviewer thinking: Clear structure. I can evaluate this.]

When you translate your expertise into frameworks that any Stripe PM can recognize, you make their job easy.

They need to efficiently collect specific signals for their evaluation. Domain-specific depth doesn't help them do that.

What you can do instead:
↳ Don't over-index on domain-specific knowledge
↳ Build portable frameworks that translate across any interviewer
↳ Align decisions with Stripe's operating principles
↳ Structure answers so PMs can follow, agnostic of domain

There's a lot more where this came from! This is one slice from the Insider Loops Stripe guide which we've already updated dozens of times since launching based on real candidate insights.

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