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

Founder of E Q V I L I B R O | Helping people live with more balance through Coaching, Retreats and Online Workshops

I am a certified Coach with 22+ years of business experience and 700+ hours of business & life coaching experience.  

I help leaders build purposed aligned, sustainable success on their terms, and have coached more than 40 clients in 5 countries. 

After starting 3 companies (1 Exit) and becoming COO of a leading fintech (which scaled 20x to US$80mm in revenue), a 12 month sabbatical in 2022 where I did 9 months of personal work changed my life completely. 

I’ve lived both sides of business intensity and personal renewal.

Today I help ambitious leaders succeed in work AND life by creating clarity, balance, and resilience as the Founder of E Q V I L I B R O: an ecosystem offering 1:1 Life & Business coaching, immersive retreats, and group workshops.

My coaching approach combines operational expertise with transformational tools rooted in experience, not just theory. 

Some of the things I guide my coachees through:
✅  Scaling your business while staying true to your life goals
✅  Setting the right long and short term vision for your business and for your life
✅  Implementing operating systems for your company like EOS and OKRs
✅  Strategy, Operations, Org Structure & Fundraising 
✅  M&A Integration 
✅  Work-Life Integration for High Performers
✅  Habits, growth mindset and limiting beliefs
✅  Finding out your true identity and values
✅  Purpose alignment for long-term fulfillment

Ready to scale your business AND your life? I'm currently accepting 3 new coaching clients per quarter. If you're a leader ready to break through your next level without burning out, send me a message. Let's create some growth and balance. 

Background & Achievements:
→ Founder of E Q V I L I B R O (retreats + coaching for conscious leadership + workshops for leaders)
→ COO at leading fintech in Mexico - Credijusto (now Banco Covalto) - 20x growth, led integration with bank we acquired
→ 2x Startup Founder in Brazil -> one exit
→ Executive role at leading ed-tech in Brazil - Descomplica
→ Former Senior Research Analyst at Citi (LatAm coverage), Analyst at BBR Partners
→ Certified Life Coach (Mindvalley)
→ CFA® Charterholder
→ Currently completing Breathwork Instructor and Certificate of Happiness programs.

For more info on my one-on-one coaching and retreats, click here: https://dt5r2jypp9s.typeform.com/to/i2xw2w0w

Ricky Sperber, CFA

Most coaching happens on a Zoom call.
Last week I coached someone in a sauna, hiking to a waterfall, inside a river, and on top of a 2,000-meter rock at sunset.
 
Tomás Sierra Ventura came to Valle de Bravo for a one-on-one retreat with me. We've been working together for months on his business — strategy, negotiation, leadership. But this time, immersed in nature, we went deeper. Into purpose, identity, and the kind of personal work that most people never make time for.
 
He started with a hot-and-cold circuit at a spa in the middle of nature. Then sat down alone — no phone, no distractions, just a notebook — and worked through deep written exercises on his hero's journey, his values, and his identity.
 
In the afternoon we hiked up La Peña — a rock that rises almost 2,000 meters and overlooks all of Valle de Bravo. We sat at the top watching the sunset over the lake and the mountains, and had one of the deepest coaching conversations I've had in 800+ hours of practice.
 
Saturday morning: a sauna under the trees next to a river. We went through hot-cold circuits between the sauna and the river — grounding the body first, breathwork, meditation, and a full coaching session inside the sauna.
 
Tomas then sat down alone at a café surrounded by nature for his final exercise — writing down and recounting the most significant stories of his life. The ones that shaped who he is.
 
In the afternoon we hiked to Velo de Novia (a 35-meter waterfall), and walked downstream along the river all the way to the lake. The coaching session on this hike was powerful — Tomas came out with clear commitments for his life.
 
To close the retreat: a sound healing session under the trees. The vibrations helped bring everything from the two days into the body.
 
In 48 hours: breathwork, meditation, movement, a sauna, a river, 3 coaching sessions, 5 deep personal exercises, 2 hikes, a sound healing, and a lot of silence.
 
The specifics of what we worked through are confidential — as they should be in coaching. But in his own words:
 
"Disconnecting helped me clear my mind and come back to myself. I could finally see a much bigger picture of what I want to do."
 
"Ideas came up during the hikes and the exercises that I had never thought of before — including possible new projects."
 
These one-on-one retreats are one of my favorite things about what I do. I've organized and facilitated them 7 times now in Valle de Bravo, and every time my clients walk out seeing themselves and their lives differently.
 
If you're a founder or leader who needs to step away from the noise and do some deep work on yourself — DM me.

3x Founder (1 exit) turned coach | I help founders and CEOs scale their companies without losing themselves | 800+ hours coaching

6 months ago, my coaching client owned 0% of the company he built. Now he's about to own half.

He runs a 50-year-old manufacturing company in Mexico. When he took over as CEO 5 years ago, revenue had been flat for over a decade. 

Then he came in and grew revenue 3x in 4 years, professionalized operations, and diversified the business.

But he had a problem. His partners promised him 10% equity when he walked in. Five years later — nothing. No contract, no shares. Just "we'll get to it."

He reached out to me six months ago. And within that time, he went from 0% equity to negotiating a deal that will soon give him 50% of the company. 

Here's how we got there.

The first thing I noticed was how he showed up with his partners. He'd walk into shareholder meetings carrying all the weight and walk out having asked for nothing. Every time.

We dug into this in one of our coaching sessions and uncovered something that had nothing to do with business — a pattern rooted in his childhood that made him believe he wasn't worth what he'd built.

Once we started working through that, things moved fast. In his own words, here's what changed:

→ He found the confidence to actually make decisions in partner meetings instead of deferring
→ He learned to set real boundaries — he told his partners: if this isn't resolved by Q1, I'm out by September
→ He developed negotiation power he didn't know he had
→ He started protecting himself — putting his own interests on the table, not just the company's
→ He gained clarity on what decisions to make, and when

We also worked on the business side — cash flow management, risk exposure, negotiation strategy. But the business work only landed because of the personal transformation he pushed through. Once he stopped operating from guilt, the strategic decisions got sharper.

He recently told me: "The most important thing was that you gave me confidence in myself to make the decisions."

Most leaders I work with don't need more frameworks. They need someone who can work on both the inner game and the business game — because one without the other doesn't stick.

If that resonates — DM me.

Investors were lining up to fund his company's expansion.
He said no to all of them.

My coaching client Franco Capurro-Soler is building one of the coolest community-driven real estate projects in Baja California.

Last year, his project started gaining real traction. Members from different countries bought land. Referrals were bringing new buyers.

Then the calls started coming. Developers and investors asking him to replicate what he'd built in other places like Costa Rica. Real money on the table.

Soon focus started spreading thin, and priorities changing fast. Stress and a sense of overwhelm kicked in.

We worked through these in our sessions. What his company actually needed was simpler than he thought:

→ Sell more to the customers that already trusted him
→ Improve the product they already love
→ Strengthen how he delivers it
→ Only then think about new geographies

He was about to jump straight to step four. Instead, he chose depth over expansion. He doubled down his efforts in Baja.

The results of this laser focus were clear just a couple of months later. He sold out his land in Baja. Bought more nearby and sold out again. Chose the right partners to build and design the homes. Started bringing the community together with events that didn't exist before.

That business traction is great on its own. But the real prize: he felt much more freedom (important to him) and did all of it with much less stress.

The cherry on top: investors are still knocking on his door.

We just finished a 6-month coaching engagement. It's been a privilege, hermano.


Pic with Franco right after our final session last week.

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