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

Big news! I'm so excited to welcome Derek Haswell to the team as a Partner and Founder Coach! 

I met Derek early in my coaching journey, and have wanted to conspire together in some way for years. He's amazing. And now I'm eager to see what we get up to together at IO. 

In 2013, Derek accidentally co-founded a meditation company. He helped build an award-winning product, scaled to 8-figure ARR, and worked with some of the best meditation teachers in the world, including the Dalai Lama.

Today, Derek blends outer work (strategy, goals, accountability) with inner work (self-awareness, resilience, what's actually driving the stuckness).

In his own words:

“I've lived that trade-off as a founder and it sucked... for everyone. Then I discovered they could be part of the same path, and it changed everything. Now I help founders make the same shift.”

I’ve known Derek for years, as a coach, a builder, and a wonderful human being, and I’m so excited to co-create Inside-Out with him, and support our founders in scaling consciously.

Check out Derek's full story in the comments. It's worth the read.

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

I have big news. But first, a story. 

I talk with founders every day who are in the middle of real inflection points.

Co-founder splits. Post-exit identity crises. Scaling without burning out. The weight of figuring out who they are as a leader.

But I only coach 15 people at a time, which means I can't work with most of the founders I speak with.

That's always bothered me, so we're doing something about it.

Introducing: Inside-Out Virtual Workshops.

Small (around 8 people). Led by me and the Inside-Out team using the same frameworks and modalities we use with our 1-1 clients, finally accessible to a broader group of founders.

The first workshop is Getting Unstuck. It's for the founder or exec who knows how to do hard things, but keeps hitting the same wall in one specific area.

Most approaches to this work outside-in: Better habits, tighter systems, more accountability. And if that's worked for you, great. But if you've tried all that and you're still stuck, the problem probably isn't discipline.

This workshop works from the inside-out, using IFS (Internal Family Systems), an evidence-based framework that has become one of the most powerful tools in serious executive coaching.

Give me 90 minutes. You'll leave with a new way of seeing the stuckness and a concrete experiment to take into your life.

WHEN: March 23rd. Noon to 1:30pm ET.
COST: Free

Space is very limited. Click the link in the comments if you'd like to apply.

A client told me: “The single most important thing for my company right now is the fundraise.”

Then he paused. “And it’s the thing I avoid every morning.”

I see founders in inner conflicts like this every day. This type of dynamic can take years to unwind, and kill companies and relationships along the way. 

After nearly a decade of coaching founders, I've found one reliable method for resolving inner conflicts like these: 

Internal Family Systems, or IFS. 

IFS is a leading toolset at the bleeding edge of exec coaching, and is built on the only scientifically proven method to change emotional learnings, Memory Reconsolidation.

It's a core tool in our practice at Inside-Out, and we're teaching founders how to use it themselves live on March 23. 

When we looked inside at this particular issue, we found two competing parts.

One part wanted the company to grow. The other part said, “If this fails, you’ll look like an idiot in front of your investors.” So we work on the problematic part. Once you do that, the system stops conflicting.

This doesn't take weeks of months. The best coaches help clients get unstuck in an hour or less. 

Want to learn how it works? Apply for our first intimate workshop on March 23. Application in comments.

"The moment you doubt whether you can fly, you cease forever to be able to do it."
–J.M. Barrie, Peter Pan

I've played basketball my entire life, and here’s what I’ve noticed. If I step on the court
believing I'm the best player there, I hoop. If I'm uncertain, I play poorly.
Leadership works the same way. If you believe you'll win, you'll win. If you believe you'll lose, you'l lose.
Confidence is king.

But real confidence isn't peacocking. It's not pretending you have all the answers. It's not even earned through success. You can build a great company and still be one bad outcome away from doubting yourself.

Real confidence comes from alignment between who you are inside and how you show up in the world.
The ball’s in your court.

For most of my career, creativity came from pressure. From big problems I had to solve. From outcomes I needed to hit. 

But there's a different kind of creativity that lives underneath all of that. It comes from joy. From play. From love. I call this place presence. And it's where the most interesting work happens.

I see this all the time working with post-exit founders. During the scale-up, every identity shift serves the company. But after the exit? When that crutch is gone and you're staring at a blank page, wondering what's next?

That's when the real work begins.

Because now you're not choosing who to be based on what needs to get built. 
It's terrifying. And it's also the most creative place I've ever been.

There’s a hidden force behind many “productivity problems.”

It’s not laziness. It’s not discipline. It’s not even time management.
It’s fear.

When pressure, uncertainty, or self-doubt creep in, the brain doesn’t lean into bold work.

It looks for safety. Suddenly emails feel urgent. Slack feels necessary. Small,
controllable tasks replace the ambiguous, high-stakes ones that move things forward.
From the outside, it looks like busyness.
From the inside, it’s avoidance, rooted in fear.
And the insane part? It feels rational.

Understanding how fear quietly reshapes attention, decision-making, and execution is
one of the biggest unlocks for founders and high performers.

Because you’re not always fighting a workload problem.

Sometimes you’re fighting a fear problem.

The most defining part of leadership isn’t certainty. It’s the unknown.
Especially now, when AI and systems increasingly handle the predictable, repeatable, “figured-out” work, what remains for founders and CEOs is ambiguity.

Leadership becomes a cycle:
Enter the unfamiliar.
Navigate the discomfort.
Create clarity.
Hand it off.
Repeat.

The lesson is simple, and I’m trying to follow it myself.
Stop treating discomfort as a warning sign.
It’s usually evidence you’re exactly where you need to be.
Learn to recognize it.

Normalize it.
Build the internal capacity to move forward anyway.

Most people have picked a side on AI.
Either it's the greatest tool ever built, or it's an existential threat we're sleepwalking into.

The binary is comfortable. But the leaders I work with who are navigating this most
effectively have learned to hold something harder: Both.

The fear is real. It lives in the gut. It wakes you up at 3am thinking about the world your kids will inherit. The excitement is equally real. As it should be.

The mistake isn't feeling one or the other. The mistake is collapsing into one becausethe other is too uncomfortable to carry. 

The most important things in life are paradoxical. They resist resolution. And AI may be the defining paradox of our time.

As F. Scott Fitzgerald said, "The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function."

Angry seagulls are going to make you a better leader. Stick with me and I’ll
explain.

You"re in a board meeting. An investor cuts you off. "I don't think you know what you're doing. Your strategy is completely wrong."
Do you fight back or shut down?
When this happened to me once, I made two mistakes.

First, I said "okay" while quietly resenting the investor. That didn't work.
Then I pushed back and defended myself. Also a mistake. It took me years to find the third option. Get curious.

Not the kind of curious where you ask questions to trap them. The kind where you stay grounded in yourself while opening up to what you might be missing.

You're going to run into "angry seagull" investors. It's not if, it's when.
You can fight back. You might win the moment, but you won't grow.

You can blindly agree. You'll lead your company somewhere you don't believe in. Or you can ask questions. Really listen. Stay confident while staying open.

How you react when you're uncomfortable dictates the trajectory of your company and
career.

So…

What angry seagulls are in your life right now?
The investor who keeps pushing back?
The co-founder who questions every decision?

The board member who never seems satisfied?

What would it look like to stop resisting them—or blindly accepting them—and start
getting curious about what they're here to teach you?

https://lnkd.in/gHUzHVcZ

The most comforting and terrifying thing I’ve learned in business is the same truth. Here's the story.

My real education happened inside a startup accelerator. 12 intense weeks, surrounded
by founders, mentors, and Thursday night “fireside chats.”

One moment stuck.
A wildly successful executive paused when asked for his single biggest lesson for entrepreneurs. “Nobody knows what the hell they’re doing,” he said.

“The difference between successful companies and unsuccessful companies is that, with the successful ones, you can’t tell.”
That perspective has followed me through every stage of my career.

Do they teach that in school? I wouldn’t know.

https://lnkd.in/g_P32hAy

One late night, I got a call from a board member.

It was around 11pm my time, which means it was probably 3am his time.

What he said stuck with me forever.

Most leaders don’t have a strategy problem.
They have a validation problem.

The most dangerous addiction in business isn’t money or power.
It’s being liked.

Applause feels like progress.
Agreement feels like safety.

Slowly, decisions stop being about what’s right and start being about what won’t upset anyone.

That’s not leadership.
That’s people-pleasing with a title.

Control is the most expensive illusion in your company.

My Zen teacher used to tell me, “Sit down, hold everything still, and watch what moves.”
What moves is everything you don't control. Your thoughts arrive uninvited. Your
emotions surface without permission. The narrative you've built about agency begins to
quietly unravel.

AI is doing something similar at civilizational scale. It moves too fast, builds too
suddenly, disrupts too completely to let you maintain the fiction. But I've come to believe that confrontation is a gift.

The founders who thrive aren't the ones who reassert control in the face of uncertainty.

They're the ones who find a different relationship to power, one that doesn't require control as its foundation.

That's not passivity. It’s a more sophisticated form of strength.

"You have power over your mind, not outside events. Realize this, and you will find strength." — Marcus Aurelius

This video has been making its way around the Internet. You should stop and watch before you keep reading.

Most people think reading 900 words per minute is impossible. Until they do it.
What changed?

Not their brain. Not their intelligence.
Their belief about what was possible.

We’ve seen this before.

Same with running the four-minute mile.
And having smart machines.

Entrepreneurs do this constantly.

We build invisible ceilings and convince ourselves they’re real.
Then a crisis hits. Or something else forces your hand.
And you discover the ceiling was never real.

When people read 900 words per minute for the first time, there’s genuine shock. Like they discovered some supernatural ability.
But they always had it. They just never gave themselves permission to use it.

Most limitations are just untested assumptions.

Question the ceilings. Test the assumptions.
You’ll probably discover you’ve had the ability all along.

An interesting question to sit with:
What limitation are you currently living with that is, in fact, just a belief?

The best CEOs I know have shorter to-do lists than you.

A perk of my work is getting an intimate look into the habits and systems of leaders across the world.

And something I've noticed about the best CEOs isn't what they do. It's what they decide NOT to do.

Most people let their to-do list become infinite. They pack in as much as possible, check off what they can, and roll everything else forward. The list never ends. And they wear it like a badge of honor.

But here's what they're avoiding: The confrontation of choice.

Saying "I'm not going to do this thing" feels permanent and final. Like you're actively choosing failure in that area.

And that's uncomfortable.

So instead, people keep everything on the list. They tell themselves, "I'll get to it eventually" and avoid the psychological weight of consciously letting something die.

The best CEOs do the opposite.

They stack rank their tasks by importance, look at their calendar, and slot only what will fit. Then they consciously move everything else to next week's list, or kill it entirely.

The result? They finish their work most days. And they get exceptionally good at one of the most important skills in leadership, which is saying no to important things.

Because here's the truth…

Your workload never decreases as you grow. You just get better at leading. And having less time forces you to delegate, empower your people, and build your organization instead of just working harder.

Your to-do list is a daily training ground for this.

Every day, you're forced to confront what dies so something more important can live.

That confrontation is the work.

Not the hustle of doing more, not the performance of appearing busy.

The discipline of doing what counts. And ruthlessly eliminating what doesn't.

https://lnkd.in/gbCGxgNW

Open article: Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care by leadinsideout.io

Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care

Scaling a company means giving away the work you used to take pride in.

Watch and listen to why that moment is harder than most founders expect.

I once heard a story that stayed with me.

A little girl walks through a garden for the first time. It was overwhelmingly beautiful, and
she runs inside to tell her mother.

Her mother smiles. “Those are pretty flowers, aren’t they?”
The next day, the girl returns to the garden… and sees “pretty flowers.”

The label stripped the magic. It flattens wonder into familiarity.

I catch myself doing this in business.
A group of complex, brilliant, unpredictable humans becomes “the sales team.”
Or “engineering.”

And without realizing it, I narrow how I see them.

Abstraction isn’t wrong. It’s essential.
But every so often, a moment of awe — in nature, in conversation, in work — reminds
me:

Reality is always richer than the words we use to contain it.

I’m doing my best to remember that.

https://lnkd.in/gxyzemuH

Have had the pleasure and privilege of getting to know Ryan, and +1 to all this

Founder/CEO at HealthBar | Healthcare Delivery & Payor Model Innovator/Entrepreneur/RN

If you don't know Ryan Cummins, you absolutely need to make it a priority!


Having Ryan close our 'Health'care 2026 conference with a keynote address is going to be engaging and empowering

The work he's doing is absolutely incredible 

His curiosity to learn is unmatched

And his focus on future generations is inspiring.....


Don't miss an opportunity to hear from, and meet Ryan at 'Health'care 2026!

healthcare2026.com

#health #healthcare #business #ceo #entrepreneurship #events

Micah Baldwin

Leadership Coach | Senior Executive | Serial Founder

In my work as an executive coach, I work with leaders that are looking to grow as people and managers. I bring 20+ years of tech community experience, where I have founded or been early at six companies (4 exits), which have raised more than $350mm. I have been a mentor/advisor to hundreds of companies over the years, and am a trained coach with more than 3 years of experience.

My work as a founder and senior executive has driven venture-backed startups to achieve large-scale multi-million dollar global growth. I’ve nurtured the growth of several startup ecosystems by leading strategic planning and engagement, with a focus on cultivating strong partner relations and customer success to create intuitive business solutions and products. 

Selected Accomplishments:

* Built an incubator with nearly 300 members who have raised more than $111 million in venture, recruited 15 corporate partners, and produced more than 200 programs with more than 4,000 attendees
* Created and launched a senior-level program for corporate innovation at AWS designed to increase affinity and, working with some of the largest enterprises and hottest startups in the world
* Led growth of key strategic accounts at AWS, often seeing spend increase drastically through onboarding, adoption, and retention
* Was early at or founded six startups, which have raised more than $350 million collectively, including 4 exits
* Successfully launched several companies, including growing a publisher base from zero to 10,000, revenue to multi-millions, and monthly page views from 11 million to 450 million per month within one year

Global Head, Founder Experience

Run a team focused on providing support to Founders throughout their experience building and growing companies. 

Yesterday, Jack Dorsey cut 4,000 people from Block. Nearly half the company. Gone.

His reason? AI tools mean smaller teams can do more. The stock jumped 24%.

Wall Street cheered. And 4,000 people opened their laptops to a severance notice.

I want to talk about the thing nobody's saying out loud:

The existential dread is real. And it's everywhere.

Not just at Block. Not just in tech. It's the person in your office who read that headline last night and couldn't sleep. It's the engineer who's been quietly wondering if the tool they're building is training their replacement. It's the ops lead who just watched their entire function get described as "automatable."

Dorsey said something that landed like a gut punch: "I don't think we're early to this realization. I think most companies are late."

He's probably right. And that's exactly what makes this so terrifying for so many people.

Here's what I know from building companies and coaching founders through hard decisions:

Layoffs are never purely about technology. Block quadrupled its headcount during the pandemic. The stock is down 80% from its 2021 peak. AI is a real force AND a convenient narrative. Both things can be true.

But the fear people are feeling? That's not about Block. That's about the creeping sense that the rules changed and nobody sent a memo.

If you're sitting with that dread right now, here's what I'd offer:

Your worth is not your job title. It never was. The economy will reorganize. It always does. But YOU have to reorganize too. The people who thrive through disruption aren't the ones who pretend it isn't happening. They're the ones who get honest with themselves about what they actually bring to the table that a model can't replicate.

Judgment. Relationships. The messy, human, creative work of leading other humans through uncertainty.

That's not automatable. Not yet. Maybe not ever.

And if you're a leader making these decisions — be honest about why. Your people deserve that. Don't hide behind "AI" when the real story is more complicated.

4,000 people deserve more than a narrative.

In 2011, I started hosting a meetup at Pilgrim Kitchen, a donut shop in Belmont, CA. Every Saturday morning. Nothing fancy. No panels, no pitch decks, no name tags. Just founders and investors sitting around eating donuts and talking honestly about what they were going through.

I didn't plan it as anything important. I just thought people needed a place to be real with each other. Turns out, that was exactly the point.

We did it every Saturday for seven years.

Founders are surrounded by people all day, but the job is lonely. Your team needs you to be confident. Your investors need you to be optimistic. Your co-founder is fighting the same fires you are. There aren't many places where you can sit with someone who actually gets it and say, "I don't know what I'm doing right now."

Pilgrim Kitchen became that place.

People walked in as strangers and walked out as lifelong friends. Not because of some networking exercise, but because they got honest with each other over cheap coffee and sugar. Vulnerability does that. When you stop performing and start telling the truth about how hard this is, you create bonds that outlast any company.

I've help build six companies that raised hundreds of millions of dollars. And the thing that got me through the hardest stretches wasn't strategy or funding. It was the friends who had been through it too. The ones who picked up the phone at midnight. The ones who said, "Yeah, me too."

Seven years of Saturday mornings taught me something I wish I'd known earlier: the companies come and go. The friendships are what last.

If you're a founder and you don't have those people in your life, go find them. Start your own version of Pilgrim Kitchen. Grab coffee with someone who's in the same fight. Be the first one to say something honest.

You don't need another advisor. You need a friend who gets it.
-----
Stoked to be coaching with friends who have been there and done that at Inside-Out Leadership.

The one truth every founder misses before starting a company:

You think the hard part is the idea. The product. The fundraise. The market.
It's not.

The hard part is you.

The thing that nearly broke me every single time I've built a company wasn't the cap table or the competition — it was the version of myself I brought to the work.

Here's what nobody tells you before you start:

Your anxiety will make decisions for you if you let it. It'll dress itself up as "being cautious" or "waiting for more data." But what it's really doing is keeping you from the hard conversations, the hard pivots, the hard calls that your company needs you to make.

I learned this the painful way at Graphicly. I had the information. I had the instincts. But anxiety drove me away from being forceful and steadfast when it mattered most. I avoided the hard decisions I should have made which is my biggest regret as a founder.

After coaching hundreds of founders, I can tell you: the pattern is everywhere. 

The founder who won't fire the co-founder. The CEO who won't kill the product line. The leader who keeps "exploring options" instead of choosing.
It's never a strategy problem. It's a self-awareness problem.

Before you start a company, ask yourself: Do I know what I look like when I'm scared? Because your team will see it before you do.

The founders who last aren't the ones with the best ideas. They're the ones who learned to lead themselves first.
----
At Inside-Out Leadership we have worked through the hard decisions as founders. Struggling with what the right next step is? DM me.

Anxiety almost ended my career as a founder.

It also saved it more times than I can count.

For years I treated anxiety like an unwanted houseguest. Something to manage, medicate, or push through. I never stopped to ask what it was trying to tell me.

Here's what I've learned after six companies and a bipolar diagnosis I didn't get until my mid-30s: anxiety is not the enemy. Confusion about anxiety is the enemy.

There are two kinds.

Signal anxiety is your nervous system doing its job. It shows up when something important is at stake, when a decision deserves more attention, when your body knows something your spreadsheet doesn't. This is the anxiety that made me slow down before a bad hire, reconsider a term sheet that looked too good, or finally have the hard conversation I'd been avoiding. It's data. It's a gift.

Noise anxiety is the other thing. The 3am spiral. The catastrophizing. The story you tell yourself about what everyone thinks of you, your company, your last all-hands. It's not pointing at anything real. It's just fear eating itself.

The founders I coach struggle most when they can't tell these two apart. They dismiss the signal because anxiety feels bad. Or they chase the noise because anxiety feels urgent.

Learning to sit with anxiety long enough to ask "what are you actually telling me?" changed how I lead. It changed how I make decisions. And honestly, it changed how I treat myself.

You don't have to eliminate anxiety to be a great founder.

You have to learn to listen to it better.

--------
Inside-Out Leadership coaches help founders understand how to harness the signals our bodies and minds are telling us. Come learn more!

taplio

The Battle

Ryan H. Vaughn

Micah Baldwin

Followers

Posts

Engagements

Likes

Performance ScoreRyan H. Vaughn's LinkedIn Performance

Performance ScoreMicah Baldwin's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Ryan H. Vaughn

Micah Baldwin

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Ryan H. Vaughn's LinkedIn Performance

Performance ScoreMicah Baldwin's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreRyan H. Vaughn's LinkedIn Performance