About Inside-Out

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.

For 15 years as a founder/CEO, I often felt like getting the job done required me to present only the most polished, hyper-competent version of myself and my company, at all times. So I kept my struggle hidden, and played the role of the “perfect CEO.”

I saw what the outside world wanted of me, and did my best to make my insides match. And it “worked.” I built, scaled, and eventually exited my company. But it cost me dearly. In the name of success, I nearly lost myself.

You may think that you’re alone in this struggle. But as a coach, I see this in nearly every founder I meet.

There is a reason for this type of polish in some cases (fundraising, recruiting, etc), but over time I also saw how my need to look competent actually got in the way of my learning and growth. How it stifled innovation, created rifts between the leaders of my company, and eroded my confidence.

And I began the process of coming home. Thanks to many wonderful coaches, teachers, and mentors, I learned to do the Work. To unlearn all the ways I created a life that didn’t serve me, all the ways I sacrificed myself at the altar of unimportant things. I summoned the bravery to lead as myself, rather than the person I thought my employees and investors wanted from me.

I 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.

It didn’t take long before the others found me.

My fellow coaches — serial founders Jason Pliml and Santi Jaramillo, both of whom had built, scaled, and exited their own companies, and both of whom had gone through their own dark night and found their way home through the power of transformational coaching. Each of us, trained and certified executive coaches, still on our own journey, doing our own inner work, integrating all the pieces and parts of ourselves into whole, holistic human beings, builders, and leaders.

And founders from around the globe, including those leading some of the fastest growing companies in tech. General Partners from some of the world’s most successful venture capital funds. Each reaching out with their own struggles and achievements, and their own masks of competence hiding real, vulnerable, human beings. And their own goals to use their lives for the greatest good.

I-O is 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.

I hope that you will join us.

— Ryan