Ryan Rouse

Growth advisor to consumer businesses with a focus on every line of the P&L | Previously, Co-Founder at Factor Meals (acquired), CEO at Highkey

Growth-minded CPG leader with deep experience across finance, brand building, and operational leadership.

After more than a decade in finance—culminating in an eight-year tenure at Merrill Lynch—I co-founded Factor_, a ready-to-eat meal delivery company that went on to be acquired by HelloFresh for $277M in 2020.

I joined HighKey Snacks as Chief Marketing Officer and later CEO, guiding the low-sugar snack brand through rapid expansion and an acquisition in 2024.

I'm currently the President of MALK Organics, a fast-growing, near nine-figure brand redefining the plant-based milk category with its commitment to clean, organic ingredients and uncompromising quality.

And I write a newsletter about what it really takes to grow—your company, your mindset, your tolerance for chaos:
​
​• The unfiltered truth about building a brand
• Why “strategy” isn’t always strategic
• What to do when everything feels on fire
• Mindset shifts that keep you sane(ish)​
• Founder mistakes, market moves, and lessons I’m still learning​
​
​Part playbook, part perspective shift.
For anyone trying to grow something—and keep their head on straight.

Sign up using the link here (or below my profile pic above): https://ryanrouse.me/

Vice President | Partner

Data driven investors in early stage consumer brands. 

We just launched a line of coconut-based creamers and they absolutely slap.

(Shout out to my kids who would cringe hard at that.)

No gums, no oils, no natural flavors. 

Just real, recognizable ingredients and a texture so creamy it'll make your coffee blush. 
​
🥥 Available in 3 flavors: Vanilla, Sweet Cream, and Unsweetened (for the purists)​
🥥 USDA Organic, non-GMO, glyphosate residue-free​
🥥 Clean label, full flavor: proof you don’t need additives to taste good ​
​
Hitting refrigerated shelves across the US as we speak. 

You should try them. For real.

Being direct is becoming synonymous with being rude. 

Which affects our ability to move things forward faster in business. 

You can be direct and respectful at the same time. 

And if you create an environment where people practice both, it has a big impact on how quickly you make decisions and get things done. 

Because the message being delivered is how things move forward in business.


~~~~~~~~~~~~~

If you liked this post, you'll love my emails. No BS musings from 12+ years in the trenches building brands.

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Work-life balance is a lie.

At least the way most people talk about it.

I've done all the "resolutions."

Tried blocking my calendar perfectly. Promised myself I'd be done working at 5:30 every day. Swore I'd never check email after dinner.

All had the same (lack of) success rate that new years resolutions have. 

Because life doesn't care about your color-coded calendar.

Sometimes work demands more. A launch comes up. You're in back-to-back calls, reviewing decks late at night, burning the candle at both ends. 

Other times, family demands more. Gymnastics meet on a Thursday afternoon 4 hours away. Your wife is out of town. The dogs need to go to the vet in the middle of the day. 

The goal isn't equilibrium at all times. 

It's understanding which side needs you more at any given time. And being there when it does.

No guilt. 
No apology. 
No pretending you can split yourself perfectly down the middle.

Entrepreneurs should think in two time frames:

30 years
90 days

I read this in a book by the legendary Dan Sullivan over a decade ago and it hurt my brain.

Because the more common advice is to regularly map out 1/3/5 year plans.

But the older I get and the more time I spend in early stage companies, I've moved more and more towards his away of thinking.

Cast a long term vision.
Execute what's in front of you.

It can be as simple as that.


~~~~~~~~~~~~~

If you liked this post, you might like my emails. No BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

https://ryanrouse.me/

Social media will have you believe if you haven't made millions by 30, you're late.

It's bullshit.

Warren Buffett made 99% of his wealth after 50.
Ray Kroc was 52 when he started McDonald's.
Vera Wang was 40 when she entered fashion.
The list goes on and on...

Know what those extra decades give you?

Pattern recognition. You've seen enough cycles to know which ones matter.

Scar tissue. You've failed enough to know it won't kill you.

The pressure to achieve young is manufactured. 

By people selling courses. By media celebrating outliers. By your own impatience.

You're not late. The game is longer than they tell you.

Good thing too. 

Because big moves develop over decades.


~~~~~~~~~~~~~

If you liked this post, you might like my emails. No BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

https://ryanrouse.me/

I used to think being intense was the problem.

It's not.

Letting other people control that intensity is.

I'm wired hot. Always have been.

It's helped me build things, push through walls, and get results most people won't.

But I also let it burn bridges I didn't need to burn.

The shift came when I stopped waiting for someone else to tell me to dial it down.

I learned to own the dial myself.

Still intense. Still emotional.

But now I decide when to turn it up and when to pull it back (most of the time, not perfect).

It's been the difference between intensity being an advantage vs. a liability.

Self-awareness isn't about changing who you are.

It's about controlling how you show up.

~~~~~~~~~~~~~

If you liked this post, you might like my emails - no BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

https://ryanrouse.me/

Your mood is not private.

It's broadcasting to everyone around you.

Show up to a meeting stressed, and watch what happens.

People tense up. Conversations get shorter. Ideas stop flowing.

Show up calm, and the opposite happens.

People relax. They think clearer. They bring solutions instead of panic.

I used to think emotions were personal.

Something I could feel without affecting anyone else.

I was wrong.

Every time I showed up frustrated, my team got quieter.
Every time I showed up anxious, my team got nervous.
Every time I showed up scattered, my team got confused.

They weren't reading my words.

They were reading my energy.

And matching it.

As a leader, your emotional state isn't just yours.

It spreads.

Like a cold. Like a yawn. Like panic in a crowded room.

The question isn't whether your emotions are contagious.

They are.

The question is: which ones are you spreading?

Because your team is catching whatever you're carrying.

—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

Most CPG leaders think scale comes from distribution.

It doesn't. 

It comes from obsession with the consumer.

Here's a few things to focus on:

- Own one emotional job
↳ Stop trying to be everything. Find the single moment your product owns in someone's life and dominate it completely.

- Build for the shelf, not the deck
↳ Your brand needs to work in 0.3 seconds at eye level. If it doesn't pop in-store, your strategy deck is worthless.

- Let data inform, not decide
↳ Numbers tell you what happened. Instinct tells you what's next. The best leaders use both but trust their gut on the big bets.

And a few to avoid:

- Chasing every retail door
↳ Bad distribution kills brands faster than no distribution. Be selective. Own where you show up.

- Innovation theater
↳ Line extensions aren't innovation. Stop launching SKUs that confuse your consumer and dilute your shelf presence.

- Forgetting you're selling to humans
↳ Your consumer isn't a demographic. They're someone's mom, someone's kid. Build for real people, not personas.

The brands that win don't follow "category playbooks".

They create their own (that everyone else tries to follow for the next decade, unsuccessfully).

So I'll ask directly: what truth about your consumer are you ignoring because everyone else in your category is ignoring it too?

"The consumer isn't a moron. She's your wife." - David Ogilvy


~~~~~~~~~~~~~

If you liked this post, you'll love my emails. No BS musings from 12+ years in the trenches building brands.

Sign up free here:

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5 things founders get wrong about employee motivation:

(From someone who got all 5 wrong)

1. Expecting owner-level commitment from employee-level equity.

You own 40% of the company. They own 0.1%.
You'll make millions if it works. They'll make rent.

Stop acting surprised when they work less hours.

2. Thinking your sacrifice is their baseline.

I worked for no salary for three years. Maxed out credit cards. Emptied my 401k. 

That was my choice. Not theirs.

Your personal bet doesn't become their obligation.

3. Using guilt instead of respect.

I used to send passive-aggressive Slack messages when people left on time. "Must be nice to have work-life balance."

Real asshole moves.

Then one of my best employees quit.

In his exit interview, he said: "Ryan, you chose to mortgage your house for this company. I didn't."

He was right.

4. Believing more equity will change how people work.

I once gave someone more equity expecting it to change their output. It didn't.

That's because everyone has a "work MO." A default gear.

If they're a killer, they'll be a killer.
If they do the bare minimum, they'll do the bare minimum.

Equity won't flip that switch.

(It will help retain the killers, tho.)

5. Confusing presence with productivity.

The person cranking until 9pm isn't always your best performer.

Sometimes they're just slow. Or inefficient. Or avoiding something at home.

Judge output, not hours.


The fix isn't complicated.

Find people who give a shit about doing good work.
Pay them well.
Respect their time.

They won't work until 10pm unless it's truly necessary.

But when it is necessary, they'll be there.

Because you hired people who are wired for it. 

And earned their trust.

—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

I've never been the smartest person at any company I've been at.

But I'm always the fastest.

At Merrill Lynch, I was 1 of 75,000 employees. Could've been the best analyst on the floor. Still replaceable.

At a startup? Different game.

My superpower wasn't an MBA or some fancy framework.

It was knowing how to find shit fast.

When my co-founder at Factor_ asked "How do other meal delivery companies handle returns?"

Everyone else: "Let me schedule some calls."

Me: Ordered from 3 competitors. Submitted returns. Pulled their policies. Built a framework. Done.

Couple of hours, tops. 

Founders already know how to find answers. That's how they got this far.

They're not asking you because they're lazy. They're drowning.

The employee who says "I researched this, here are three options, I recommend X because Y" - and did it FAST - becomes indispensable.

The one who says "I don't know, what do you think?" becomes overhead.

At early stage companies, resourcefulness and urgency beat credentials every time.

No waiting. No deferring. No "I was waiting for you to give me the go ahead."

Run. It. Down. 

And do it quickly. 

Leaders will notice. 

Trust me.

—

I write emails. Unfiltered takes from 12+ years building brands.

It's free. Subscribe (or don't):

https://ryanrouse.me/

I used to think winning arguments made me smart.

It didn't.

It made me insufferable.

Healthy debate has respect and curiosity.

Ego-driven arguing has neither.

One sharpens you.

The other isolates you.

In healthy debate, you ask questions to understand.
In ego-driven arguing, you ask questions to trap.

In healthy debate, you say "I hadn't thought of that."
In ego-driven arguing, you say "Yeah, but..."

In healthy debate, you admit when you're wrong.
In ego-driven arguing, you double down.

In healthy debate, you want to learn something.
In ego-driven arguing, you want to be right.

Here are some things that helped me:

1. Pause before responding. Ask myself if I'm trying to understand or trying to win.

2. Repeat back what I heard. "So what you're saying is..." Forces me to actually listen.

3. Find one thing I agree with first. Even in disagreement, there's common ground.

4. Ask "What am I missing?" Instead of explaining why I'm right.

5. End conversations with "That gave me something to think about." And mean it.

The shift won't be immediate.

But people will start engaging with you differently.

Conversations get richer.

Ideas get better.

Relationships get stronger.

If you catch yourself needing to have the last word, you're probably arguing from ego.

If you walk away from a conversation thinking differently, you're probably debating with curiosity.

Took me way too long to learn the difference.

~~~~~~~~~~~~~

If you liked this post, you might like my emails - no BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

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"Ryan - I LOVE your newsletter. 

Thanks for being real and authentic man! I'm sending your recent email on brand marketing to my whole team its spot on!"

Got this message the other day from the CEO and co-founder of a multi-hundred million dollar brand that I have a tremendous amount of respect for. 

I don't have the largest audience or newsletter subscriber base. And it's easy to get caught in the cycle of chasing numbers. 

But that's not the point. Not for me. 

I just wanna to talk about real shit in a way that's relatable and authentic to who I am. 

And hope it's useful and thought provoking to other people. 

So when I get messages like that it helps ground me in that truth. 

Sign up for free below. 

Or don't. 

https://ryanrouse.me/

In consumer, your customers don't care how smart you are.

They care that their order arrives on time.

That you're in stock when they need you.

That your quality doesn't fluctuate batch to batch.

They're not buying your IQ score.

They're buying your ability to deliver on expectations - some general to the market and some specific to your product and promise.

That's all execution.


~~~~~~~~~~~~~

If you liked this post, you might like my emails - no BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

https://ryanrouse.me/

Learn the rules like a pro so you can break them like an artist.

This Picasso quote gets twisted constantly.

People think it's about tactics. 

But it actually means master the fundamentals so deeply that innovation becomes instinct.

In business, I see this constantly:

The CMO who never ran a P&L trying to "disrupt" pricing strategy.

The founder who skips unit economics to chase viral growth.

The exec who wants to "break the mold" before understanding why the mold exists.

The best leaders I know spent years in the trenches.

Learning why things work before reimagining how they could work better.

They got creative because they got good first.

Master the boring stuff first.

Then go be an artist.


~~~~~~~~~~~~~

If you liked this post, you might like my emails - no BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

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The most frequent question I get from entrepreneurs is "What advice would you give your former self?"

My answer: Pace myself.

They blow me off.

Not to my face, but I can tell.

I get it though.

I did the same thing when I was in their shoes.

Thought I was different.

That I could outwork the system.

That entrepreneurial fire made me feel invincible.

Until it didn't.

If you're putting in 80 hours a week consistently, it's not a matter of if you're gonna burn out, it's a matter of when.

Because you can't sustain that for the time required to play the long game. 

(Which is the only game in town.) 

Find your sustainable pace now before you're forced to. 

You're running a marathon, not a 100-yard dash.


~~~~~~~~~~~~~

If you liked this post, you might like my emails. No BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

https://ryanrouse.me/

Hard work is table stakes, not a flex. 

Your competitors work hard. 

It's necessary, but not sufficient. 

You also need to think in ways others don't. 

Most people default to putting in more hours because thinking hurts. 

It's easier to stay busy than to sit with a problem until you crack it.

I wish success in business was just about working harder. That would be simple. 

But the world doesn't give a shit about your hours.

It rewards people who create the most value. 

Value comes from seeing what others miss. 

From connecting dots in ways that seem obvious after but weren't before.

From working hard *and* smart.


~~~~~~~~~~~~~

If you liked this post, you might like my emails. No BS musings from 12+ years in the trenches building brands.

You might not, but it's free so WGAF:

https://ryanrouse.me/

Most people think they're either risk-takers or they're not.

But that's not really how it work.

Risk isn't something you have a fixed capacity for.

It's something you build tolerance to.

Like lifting weights.

You don't walk into a gym and deadlift 400 pounds because you "have it in you."

You start small. 

Then add weight over time. 

Each rep expands what you can handle next time.

Risk works the same way.

The person who quit their corporate job to start a company didn't wake up one day with superhuman courage.

They made a series of smaller bets first.

A side project. A conversation. A decision to stop playing it safe in one area of their life.

Each one stretched the muscle.

So if you think you're not a risk-taker, you're probably right.

But it's not because you can't be.

It's because you haven't trained that muscle yet.

~~~~~~~~~~~~~

If you liked this post, you might like my emails - no BS musings from 12+ years in the trenches building brands.

You might not, but it’s free so WGAF:

https://ryanrouse.me/

90% of the dietary ideologies are the same.

• Avoid processed foods 
• Reduce sugar
• High quality protein
• Healthy fats

Yet we still have tribal wars amongst the different groups on which philosophy is "best".

It'd be really cool (and powerful) if they joined forces to get as many people as possible to follow the 90% that they agree on rather than argue (with each other) about the 10% that they don't.

The Standard American Diet is still the most widely followed "diet". 

That's the enemy.

Has “Head of” as a title created more clarity or confusion?

I think the latter.

Because it’s used as an analogue/replacement to another, more commonly used, title.

Director in most cases. But not always. 

Some companies use it to replace VP. 

Which begs the question - why not just use the tried and true titles?

This is about the person in the role for me. 

People can look at their background and understand their trajectory. 

I realize Director or VP is not the same everywhere, but it’s more uniform across companies because they’ve been in existence for so long. 

“Head of” is new, and I’m just not sure what the benefits are that outweigh the added ambiguity. 

But what do I know.

You think everyone knows what you do.

They don't.

When you're deep in your business every day, the solution feels obvious. 

You live it. You breathe it. You can't imagine how anyone wouldn't get it.

But your target audience? 

Assume they're seeing it for the first time.

So you have to be clear, not clever.

Clear about what you do.
Clear about who it's for.
Clear about why it matters.

Assume the first time someone sees your message, they're distracted. 

The second time, they scroll past. 

The third time, maybe they pause. Maybe. 

So repetition is necessary.

Most brands don't say it enough.

Different ways. Different angles. Different stories.

If you're sitting on something great but struggling to get traction, ask yourself:

Am I explaining this clearly enough? 

Am I saying it often enough?

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

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.

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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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.

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Few coaches can support entrepreneurs in the radical self inquiry required to level up as leaders. Even fewer can also help entrepreneurs execute the practical steps from founding to exit from experience.

Top entrepreneurs from across the world trust Inside-Out coaches to do both.

We believe that personal development drives business outcomes. We believe that authenticity makes for more effective leaders. And we believe that you shouldn’t have to choose between achieving your business goals and living the life you want to live. 

The founder’s journey can enable us to reach rarified heights of personal and professional success, joy, and purpose. Or, it can alienate us from those parts of life we hold most dear and, ultimately, destroy us. 

Like most founders, I saw the promise of success, wealth and fame when I started my first company, but it didn’t take long for me to experience the downside as well. The stress it put on my relationships, the risk to financial and physical health, and the many small compromises I made in the name of “work,” over and over until I didn’t recognize the life I was living. 

Anyone who hasn’t been there, won’t really understand.

I, Ryan Vaughan, started Inside-Out in 2021, to give founders a platform on which to do their Work. A place to drop their armor, discover who they truly are as a leader, and unabashedly bring that person to their companies and their lives. To help founders learn to consciously and systematically build their companies to suit the life they want, not the other way around. 

Today, I'm joined by fellow coaches Jason Pliml, Santi Jaramillo, and Micah Baldwin. Each of us trained and certified executive coaches, still on our own journey, doing our own inner work. 

We are a coaching company dedicated to the idea that conscious attention and persistent effort on the areas that matter — plus a great deal of bravery when it counts — can change a life. 

And changing the life of an entrepreneur can change the world. 

CEO coaching, for founders, by founders. We help early/mid-stage startup founders scale into executive leaders & build low-drama companies, through CEO-coaching that blends psychological growth and operational excellence.

Founder, Executive Coach

Endeavor is a global non-profit that for 19 years has helped entrepreneurs and their companies in 25 countries reach global scale and relevance.

Endeavor Entrepreneur

Board Member

Helping founders step fully into their lives and scale their masterpieces.

Coach for Scale-Up Founders (via On Deck Scale)

The largest and fastest growing high school sports communication platform in America.  As the exclusive web/mobile platform for over 11million passionate fans across 40+ states (20% of the total US market), VNN is rapidly aggregating the fragmented, multi-billion dollar high school sports market onto an intelligent platform, and transforming high school sports.

Co-Founder + CEO

Helping entrepreneurs in West Michigan connect to the resources they need, while cultivating strategic positioning within the Michigan startup community.

Entrepreneur in Residence

The largest high school sports publication in Michigan.  A tight knit group of sports junkies who made it their business to ensure that high school athletes in West Michigan got the positive coverage and recognition they deserve.  

Founder

Exited founder turned CEO-coach | Helping early/mid-stage startup founders scale into executive leaders & build low-drama companies

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.

Step 2, The Eulogy: Imagine that you are at the end of a long, rich life. You’ve accomplished everything you wanted, behaving honorably and building meaningful connections with your family, friends, and colleagues....

You are proud of yourself for leaving a great legacy and for having led an organization that brought great value to the world.

You’ve done your work here and feel ready to go. 

So when you learn that your days are numbered, you take the news in stride. A lot of people who appreciate and admire you want to pay their respects, so they organize a “living funeral." At the ceremony, a dear friend will stand in front of the audience and read a eulogy.

Here is your instruction:

Spend at least 20 minutes and write the eulogy you would like your friend to give.

Please don't be humble or shortchange yourself by limiting this in any way. If it's possible for anyone, it's possible for you, and you only get this one shot. This kind of eulogy can become a north star for your life. It can help you discover who you want to be and how you want to act in order to feel complete when you leave your life.

Once you're done writing your eulogy, you're done with this step.

Pro tip: Don’t allow yourself to edit; just let yourself flow in a steady stream of consciousness.

The reason most people get stuck doing deep writing like this is that two competing energies lock horns: the Madman and the Judge.

The Madman is the raw, creative energy inside you. He’s full of ideas and writes crazily, driven by pure emotion. But the Judge - that critical, educated voice of perfection - peers over your shoulder and says, "That's trash!" The Madman loses confidence, shrivels up, and the writing stops.

If you want the truth of your deepest purpose to emerge, you have to separate these energies:

The Madman must be allowed to speak freely, without editing or censoring, for the full 20 minutes. He doesn't worry about punctuation or grammar. He just writes.

For this exercise, your job is to bypass the internal critic and allow your deepest, non-performative truth to flow onto the page. The judge can come in after the 20 minutes are up to fix the errors (or he can take a break from this exercise entirely).

Let your legacy define your actions. What are the truths about your character you want to be read from the podium?

The biggest risk to your life is not failure, but the quiet compromise of your own truth. 

Follow along for the next five days as we continue the reflection sequence. 

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

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.

Step 1, A Look Back: In my last post, I talked about creating the liminal space - the gap between who we were and who we are becoming. But, to clarify where you’re going, first you must look at where you’ve been...

It’s easy to focus solely on what to build next. It feels productive. It keeps the high-performer persona safe. But if you rush to the finish line without seeing the patterns that drove you all year, you just end up running the same tired race with a new trophy.

The most potent clarity for your future is hidden in the truth of your past. You have to close the chapter that was 2025, not just slam the book shut.

Give yourself 30 minutes to answer the following questions:

1. What happened this year?

Go quarter by quarter. List the major milestones, professional setbacks, and relational events. Don't curate the list - just the facts.

2. What are you most proud of this past year? Personally? Professionally? In your relationships?

Look past the revenue. Where did you lead from authenticity, bravery, or kindness? Where did you choose the hard, quiet thing over the loud, easy one? 

3. What were you most challenged by this past year? Personally? Professionally? In your relationships?

This is where you drop the armor. Don't self-protect - name it directly. These pressure points show you precisely where your growth is waiting.

4. When did you feel most alive?

These are your signals. For me, it’s rarely when I’m winning. It's often when I’m up against an edge, totally exposed.

5. What would you do differently if you could?

This is less about regret and more about optimizing for wisdom. Name the specific choices you’d reverse. You can't change the past, but you can harvest the insight.

6. How are you different based on what you experienced this past year?

Look for the subtle shifts. Maybe you shed a layer of armor. Maybe you found the strength to say no. Identify the permanent psychological or relational change that was forged in the fire of this year.

7. What behaviors, habits, or people held you back this year? Which helped you evolve?

Be ruthlessly honest. Bring awareness to the negative whilst celebrating the positive.

8. What lessons did you learn this year? What did you learn about yourself? What did you learn about yourself as a leader?

Every event is just data until you extract the salient principle. What are the 1-3 core, non-negotiable truths about leadership, life, and your own patterns that you now know for sure?

9. Tell the story of your year.

Complete this sentence: “When I look back 10 years from now, this year was the year that...” This distills the whole chaotic experience into a single, mythic arc.

The lessons from this exercise are some of the most valuable assets you own.

Tomorrow, we move into Part Two: The Eulogy 

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

Step 6, Setting Goals for Momentum: You’ve brought a clear definition for success in 2026 into focus, and with that, you’ve done the hardest part. Now it’s time to develop the plan to make it a reality...

When building an action plan, the key is to focus on building momentum. Feeling like you’re succeeding can be the difference between going that extra mile or letting “just this one” slip.

Traditional goal-setting processes can actually be demotivating to people trying to make a change because of the uncertainty inherent in the change process.

Instead, build momentum by separating the actions you take from the outcomes they produce and anchoring the success of your efforts to things that are in your control.

Intentionally doing so is the key to creating momentum without burning out.

By allowing yourself to define “success” as having completed the actions, and ignoring the outcomes (apart from regularly scheduled analysis in which you can dial in your actions ⇒ outcomes pipeline), you position success entirely within your control. 

Let's do it:

1. From the three definitions of success you set out, choose one outcome you want to produce (best to do one at a time, though you can return here as many times as you need for additional outcomes).

2. Chunk that 12-month outcome into outcome-based milestones at six, three, and one months.

“What would I need to have accomplished by six months to be on pace for my 12-month goal?” “What would I need at three months to be on pace for my six-month goal?" and so on.

Once you have locked in desired outcomes at one, three, six, and 12 months, shift your focus to actions.

3. Reviewing your most near-term outcome, answer the following question: What actions will I need to take to produce that outcome?

Note: actions must be completely within your control!

4. Check in with yourself: Are you ready to commit to taking those actions?

• If no, own proudly the reality that you’re not yet ready to create those results.
• If yes, put them into your diary, task management software, or however you manage to-dos, and commit to doing those tasks. The important part is to commit to doing the tasks, independent of the results they produce.

This framework is intended to be revisited and iterated upon periodically throughout the year. Many choose a monthly or quarterly cadence.

• At the regular cadence you choose, use actual data to validate your assumptions around actions ⇒ outcomes.
• To do this, once per month/quarter, dispassionately analyze whether the actions you’ve taken have produced the result you expected. 

If so: Continue on with your action plan. 
If not: Revisit this exercise, adjusting the time frames accordingly. 

What is the one non-negotiable action you are taking tomorrow that is completely within your control?

Stay tuned tomorrow for the final exercise of the reflection template.

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

Step 4, Gap Analysis: You have spent the last three days defining two things: The reality of where you are (The Look Back). The highest vision of who you could be (The Eulogy & Five Lives). Now things get harder...

Before moving on to the questions below, review the reflections you made while completing the first three exercises. Then, please answer the following questions as honestly and courageously as you can. Do not limit yourself to what's "reasonable."

1. Thinking back to your Eulogy and Look Back, list the key changes you’d have to make in order to justify such a beautiful eulogy. 

2. After reviewing your Five Lives exercise and your Look Back, list the key changes you’d have to make to ensure you didn’t leave important parts of your life unlived. 

3. Review each of these lists and identify those changes from each that scare you.

4. Ask yourself: “Am I ready to make these changes?”

The relevant commitment is not to the outcome but to the process. Analogously, the question is not whether you want to lose weight but whether you are willing to stick to the diet that gets you to your goal. This is an anthropological exercise, not a creative one. The goal is to really look internally to see if you're ready to do what's necessary. If not, that's perfectly ok.

If you are ready to make the necessary changes from the questions above, write down your commitment to memorialize it for yourself. Share it in the comments if you think that'd help keep you accountable.

If you feel you aren’t ready to commit to the changes you listed above, perhaps reviewing this article will help: https://lnkd.in/gmARwFRQ

Tomorrow, we will cover what success really looks like and how to define it for 2026.

Keep going!

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

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.

Step 5, Defining Success: “What does success look like to you?” “How will you know when you have it?“ Those are two of the most powerful questions for leaders...

When the answers are fuzzy, leaders can feel stuck and uncertain. 

Clear answers, however, create a powerful creative tension between leaders and the results they want to achieve. A clear vision for success illuminates the path and propels leaders in the direction of their dreams.

So what does success really look like to you?

Answer the following questions in order:

1. What would success look like for me in 2026? 

Start this section by journaling free form, allowing ideas to flow. Then, to end this section, see if you can summarize your journaling into 1-3 concrete definitions of success.

Now we’re going to explore those definitions more deeply, to enable all parts of yourself to understand and align around what you really want. 

2. What will having that success do for you?

Answer as many times as you need to drill deeper into what’s behind your desired outcomes.

3. How will you know when you have it? 

4. What (or whom) might you lose, that you value, when you have this outcome?

5. Considering all your answers above, capture the 1-3 specific, measurable outcomes that would constitute success for you in 2026. Each measurable outcome should be no longer than a sentence.

You may think this exercise is about setting aggressive targets... It's not. 

It’s about establishing intentionality over chaos.

When you define success this precisely - drilling past the surface goals to name the cost and the why - you achieve two profound shifts:

• You Build Self-Trust. You stop outsourcing your worth to external expectations and start leading from internal clarity.
• You Create Productive Tension. The clarity itself creates the necessary pressure - the creative tension - to act. When you measure it, you can't hide from it, and the awareness alone begins to cause change.

This work is how you begin generating momentum from a sustainable, powerful source: clarity and truth.

What is the single most powerful, measurable outcome that defines your purpose for 2026? 

Share below - I'd love to hear it.

Follow along for the next reflection exercise. 

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

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?

Step 3, Five Lives: This exercise, modified from Julia Cameron’s The Artist’s Way, is a powerful weapon for injecting nuance back into a one-dimensional life... 

If you had five other lives to lead, what would you do in each of them?

I would be an NBA player, a physicist, an astronaut, a fiction author, and a monk. 

You might be an entrepreneur, a scuba diver, a cop, a writer of children’s books, a football player, a belly dancer, a painter, a performance artist, a history teacher, a healer, a coach, a scientist, a doctor, a Peace Corps worker, a psychologist, a fisherman, a minister, an auto mechanic, a carpenter, a sculptor, a lawyer, a painter, a computer hacker, a soap-opera star, a country singer, or a rock-and-roll drummer.

You only get one shot to experience life. Don’t leave important parts unlived.

Instructions: 

1. List the things you’d do if you had five additional lives. Whatever occurs to you, jot it down.

Do not overthink this exercise. The point of these lives is to have fun - more fun than you might be having in this one.

2. Look over your list and select one life. Then figure out the smallest way you could begin to live it, this week

For instance, if you put down “country singer,” can you pick up a guitar? If you dream of being a cowhand, what about some horseback riding?

"One amazing aspect of another life I want to incorporate into this one is..."

3. Final Step:

Commit to taking the first step listed in step two in January 2026.

"I’m going to take this small step beginning in January 2026..."

Feeling fired up and want to make an impactful change quickly? Consider adding one or both of these bonus credit steps:

• Bonus credit 1: Don’t wait until January. Get started this week. 
"I’m going to take this small step towards beginning it this week..."

• Bonus Credit 2: Pick two lives.
"A second amazing aspect I want to incorporate is..."

Your commitment to your internal life may be the only true competitive advantage you have left. 

The question is, are you ready to allow your life to be as rich and complex as your ambition?

Which part of your true self are you suppressing for the sake of "output"? 
Share your unlived life below.

Follow along for the remainder of the annual reflection sequence.

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

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.

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 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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