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Inside-Out Leadership

Inside—Out is a leadership development agency, helping high-performing entrepreneurs to step fully into their lives, and transform their companies into their masterpieces.

It’s why every elite athlete in the world works with a coach — seeing your best work requires more than one perspective.

Combining decades of high-growth entrepreneurial experience, centuries of developmental psychology, and millennia of contemplative wisdom, at Inside—Out we help entrepreneurs see their work — and themselves — from a more complete perspective, and wake up to the possibility of extraordinary success and fulfillment.

Inside-Out supports some of the fastest growing companies in technology. We can say from experience that even at the unicorn level, nobody has it all figured out.

The best leaders acknowledge this, and consciously develop themselves to meet the challenge of ambiguity and uncertainty inherent in leadership.

Maybe you’re looking to improve the effectiveness and cohesion of your team. Maybe you’re looking to build the kind of corporate culture that eats strategy for lunch. Or maybe you simply want your company to serve your life, instead of the other way around.

Whatever the reason, if you’re looking to grow into the best leader you can be, reach out to schedule a complimentary strategy session, to see how we might support you in your journey.

Ready to stop pretending, and get to work?

Reach out to learn more about what we do

Ryan Vaughn

Hi, I’m Ryan.

I spent 15 years trying to be the perfect CEO, and lost myself in the process. Now I teach and coach founders how to scale their companies without losing themselves.

Here’s my story:

Over 15 years I founded and served as CEO to three companies. I raised $20m, scaled a team of 150 amazing humans, and captured over 20% of the US market.

All while doing everything I could to present only the most polished, hyper-competent version of myself and my company, at all times.

And then, 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.

There's another way. And it's fucking incredible.

Let’s talk.


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Subscribe to Inside-Out Leadership Development

Bi-weekly newsletter on entrepreneurship and leadership for those who want more than just success. Written by Founder/CEO turned Executive Coach Ryan Vaughn to help leaders step fully into their lives and transform their company into their masterpiece.


Ryan Vaughn

Exec coach for startup ppl 🙏 3x founder/CEO (raised VC 5x, failed 2x, market-winner 1x) 🚀 trying to make “Zen Blitzscaling” happen