Adam S.

My life thesis: execution > strategy. Compounding FTW. I'm an optimistic skeptic. Curiosity is the most important quality in life.

I enjoy pattern matching and read widely. The opportunity to learn every day is a gift. Time is precious. The ability to improve what and where I focus and delegate the rest is ideal. 

I [of course] love my family and friends. I believe I am a logical, thoughtful adult and therefore accept my choices. I am content and therefore I have won.

Founder and CEO @Chore. We are a founder's back-office (HR, finance, compliance, equity) operations team. Back-office operations are an undifferentiated tax on success. Focusing on your superpower enables success. Chore handles the rest (i.e. we specialize in ops so you never have to) so you can achieve your dreams. 

Host of the Entrepreneurial Excellence podcast. I dive deep with multi time founders about their key decisions, actions, hires, drivers and more that they use to achieve "excellence." 

General Partner at the Autopilot Fund. We invest in early stage startups. We love obsessed founders who have a history of breaking through walls. I have invested in over 200 startups across multiple funds. 14 are unicorns (8 from seed).

In previous lives, I founded 3 other companies, been a product leader on a big co API team, Chief Revenue Officer (CRO), Chief Operating Officer (COO), and do-it-all janitor. 

I enjoy building great teams, processes, and stories that unify a company around a shared mission. Helping others build successful businesses brings me joy. More successful startups = a better, more dynamic world.

People describe me as energetic, positive, creative, detailed and optimistic. I enjoy rational, logical, data driven debate built on mutual trust and respect. I'm not an engineer but people view me as "technical" and have built companies with the brightest PhDs and brilliant engineers. The best compliment I received was "you ask great questions."

Honesty, trust, fun, a sense of urgency and mission are what I look for in colleagues and places I work. Passion about my product, my company and my team is what drives me. I work hard and enjoy being surrounded by people who do the same. 

"Leave the world (and your business) better than when you arrived..."
"The greatest risk is not taking one!"

Always curious and learning. Subscribe to Entrepreneurial Excellence to learn.

General Partner

The Autopilot Fund focuses on early-stage companies that serve and accelerate how companies operate. 

More about us: https://autopilot.fund/

Operations span various “departments”: could be in engineering, operations, sales, finance, product, customer success… the questions we ask ourselves are:

1. Is this a founding team so capable that others should be afraid to go against them?
2. Do they understand the problem better than anyone, and have special “founder-market” fit?
3. Will they rest until they have dragged the world kicking & screaming into their vision of the future?
4. Is the product “infrastructure” in a manner of speaking: structured data, deeply embedded, sticky?
5. Does the advent of AI exponentially increase or decrease their defensibility?

Our portfolio includes some pretty special companies like AngelList, Pulley, Puzzle, Levels, Disco, among others. 

Smart founders focus. Bad founders distract themselves with all the small, non-product, non-customer work that can easily take up hours but not move your startup forward.

We are sector agnostic and focus mostly on early stage. Our thesis is simple: the best founders come from anywhere, with any background, working in any industry. Focus, joy, dogged determination, and deep knowledge about your product and how you're changing the world is what leads to success.

If you're interested in learning more, drop me a note on LinkedIn.

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.

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