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

Dashing Leadership

I'm a CEO turned executive coach that helps founders transform into high-performance leaders by shifting into the mindsets and behaviors that help them handle work with ease. My coaching leads clients to more effective interpersonal relationships, better decision making, and a more enjoyable experience of leading. 

I have a decade of experience as a venture-backed CEO, investor, and product leader. Combined with coaching over 50 CEOs, I bring both masterful coaching and operational experience to my clients. I am a great match for scaling leaders who believe their personal development is central to their company's success.

I help clients to create...
- Lower drama and greater team performance
- Clarity of job, prioritization, less thrash
- Greater enjoyment, less stress
- Less doubt, more confidence
- Seeing leadership blindspots, more self-awareness 
- Better decision making, particularly around making big changes

Learn more: www.dashingleadership.com

Executive Coach

Eaze

Senior Product Manager

Credit Karma

With over 60 million members, Credit Karma is working to make financial progress possible for everyone. Since 2007, we have been knocking down barriers that block the path to financial health, helping our members make informed choices and feel confident about their opportunities.

500 Startups

Venture Partner

Fitocracy

• Cofounded Fitocracy, a fitness social network that helps users reach their goals through progress tracking, social support, and professional coaching
• Grew Fitocracy into a 2 million user global community 
• Recruited and led team of 8 designers and engineers across iOS, Android, and web platforms
• Launched online coaching platform and achieved over $1 million GMV annual run rate in <12 months
• Raised over $2 million in venture capital
• Successfully led company to acquisition in 2016

Co-Founder, CEO

Kantar Retail

Learned the wonders of crusty enterprise software

Client Services Manager

Alvarez and Marsal

Consultant

Helping founders transform into the leaders their team needs them to be

I am a CEO turned executive coach that helps founders transform into high-performance leaders by shifting into the mindsets and behaviors that help them handle work with ease. My coaching leads clients to more effective interpersonal relationships, better decision making, and a more enjoyable experience of leading. 

I have a decade of experience as a venture-backed CEO, investor, and product leader. Combined with coaching over 50 CEOs, I bring both masterful coaching and operational experience to my clients. I am a great match for scaling leaders who believe their personal development is central to their company's success.

I help clients to create...
- Lower drama and greater team performance
- Clarity of job, prioritization, less thrash
- Greater enjoyment, less stress
- Less doubt, more confidence
- Seeing leadership blindspots, more self-awareness 
- Better decision making, particularly around making big changes

Learn more: www.dashingleadership.com

Brian Wang

Vibe coding may be the most seductive avoidance mechanism ever invented for technical founders.

A founder I once worked with had a direct report who was underperforming. The feedback conversation had been on his list for weeks. But instead of having it, he spent a weekend vibe coding an internal tool that automated half the person's job. He came in Monday feeling productive while justifying why the conversation still hadn't happened.

AI tools have made building so cheap and fast that founders can do things themselves in an afternoon that used to require a team and a quarter. And for many of them, this feels like a massive unlock. But it's worth examining what it's actually unlocking.

For some founders, AI is genuinely freeing them to focus on higher-leverage work. They delegate better, think more clearly, and use the extra capacity for the strategic and emotional work of leading a company.

For others, it's doing something more subtle. It's giving them a legitimate reason to retreat into the thing they've always been most comfortable doing: building. Vibe coding a prototype feels productive. Shipping a feature over the weekend feels like progress. Rebuilding an internal system because "I can just do it faster now" is the obvious move. Meanwhile, all of the much messier human stuff, like that difficult conversation with their cofounder, the reorg they've been talking about, or the senior hire they need to make but keep finding reasons to delay, all of it stays frozen.

AI makes the avoidance invisible, even to the founder. After all, they're not scrolling X or playing video games. They're shipping! But the reason they're building at 11pm on a Tuesday may have less to do with wise productivity and more to do with the fact that building doesn't require them to sit with a necessary discomfort.

The shift doesn't start with putting the laptop away. It starts with noticing what you're building *instead of*. If every hard leadership moment gets answered with "let me just build something," the building may not be the unlock you think it is.

Executive coach for scaling startup founders

There's a version of startup culture that looks like high performance but is actually one person's anxiety about "enough" spreading to everyone around them.

The anxious founder inevitably builds a culture in their own image without realizing it. They believe there's always more to be done, more to ship, more to optimize. While there is genuine desire to succeed, there is also a deep belief that stillness means falling behind. And that making stillness the enemy is what got them here.

The problem is the team doesn't experience the founder's drive the same way the founder does. The founder feels purpose, but the team feels pressure.

I've watched CEOs whose habit of saying yes to everything and taking on too much gets modeled by their direct reports. The whole company ends up in an overwhelm cycle, initiated from the top. The overwork has gone from personal pattern to culture.

When a founder's self-worth is tied to output, it will always break containment and cascade. The unspoken belief that "more is always possible" becomes the team's unspoken dread that "we are never doing enough."

Worse, the founder creates a self-reinforcing cycle. They over-direct when the team doesn't show enough initiative, accidentally building the exact dependency they complain about. They fire off quick Slack messages that create priority whiplash, sacrificing focused results that would reduce the "enoughness" issue. They measure every employee against founder-level intensity, producing chronic disappointment. In each case, the founder wants a motivated, hard-working team. But motivation built on anxiety about not-enough is not the same as motivation built on shared purpose.

The shift doesn't start with a new management framework. It starts with a harder question: "Is my drive actually inspiring this team or is it creating exactly what I fear?"

AI tools have gotten good enough that a lot of technical founders are rediscovering their favorite part of the job.

They're shipping features in an afternoon that used to take a sprint. They're prototyping at 11pm for the sheer fun of it. For the first time in years, work feels like it did when they started the company.

Meanwhile, the CEO work has started to feel like an interruption.

I once worked with a founder who spent a weekend building an internal tool his team had been scoping for months. He demoed it Monday morning, excited to get the team's reaction. What he was met with was ambivalence. The PM already had requirements in progress, the designer had started mockups, and engineers already had it on their sprint.

The instinct to build everything yourself is easy to justify right now. But when the CEO is the most productive individual contributor on the team, the team stops developing.

I'm not suggesting founders stop building though. Instead, they should use building as the bridge between the vision in their head and what the team actually ships. For years, the hardest part of being a product-oriented CEO was translating what they could see so clearly into specs, wireframes, and conversations that never quite captured it. AI lets them simply show the team what they mean.

The difference is what happens after the demo. "I built this so you don't have to" creates dependency while "I built this so you can see how I'm thinking, now make it better" accelerates the team's judgment.

The founders who are getting this right may be having more fun at work than they've had in years. And their teams are reaping the benefits too.

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