Introducing Camerado

Why I’m trading solopreneurship for partnership

My coaching practice has given me an incredible amount of freedom for nearly a decade. I’ve been able to set my schedule, choose who I work with, follow my curiosity and creative impulses, and move at my own natural pace—slow. That independence has allowed me to deepen my craft as a coach, publish Where the Road Bends, study Hakomi and other depth psychologies, and be present for my family.

As I deepened my spiritual practice last year, I became obsessed with relationality, the notion that we’re always in relationship with something, and how we relate shapes our experience. Through this exploration, I began noticing how lonely I felt most days, especially at work. I spent hours on Zoom each week with clients and was nourished by this work, yet still felt alone in the day-to-day running of my practice.

I longed for deep partnership and the chance to contribute to a cause bigger than myself. I wanted teammates I could learn from, create with, and count on to challenge me as a practitioner and entrepreneur. I missed the camaraderie, the shared responsibility, and the satisfaction of being on a team.

Last fall, I was at a retreat in the Catskills for Founder Satsang, an online community for entrepreneurs on the spiritual path. Dozens of friends and founders I respected were there, including Ryan Vaughn and Derek Haswell. I admired the depth and commitment they brought to their coaching and always left our conversations wiser and more inspired.

On the second night, the three of us peeled off from the larger group and sat on the porch, watching the sun slowly slip behind the Gunks. We talked about our lives, our practices, and how technology might change human development over the next decade.

As our conversation deepened, an idea began taking shape: a small studio of deeply committed practitioners who had built and led companies and spent years doing their own inner work.

We imagined a firm with both coaching and building in its DNA. We could bring our different strengths and gifts to supporting clients and help one another create innovative products, services, and experiences we couldn’t bring to life alone.

We went our separate ways after the retreat, but the idea had taken on a life of its own. Earlier this spring, we met on Zoom and began exploring whether a partnership made sense and what it would take to build the studio together. That conversation led to a daily text thread, a weekly Zoom, an offsite at my house, and eventually a commitment to become partners and launch a coaching studio.

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After six months of working behind the scenes, I’m excited to introduce Camerado, an executive coaching studio founded by Ryan, Derek, and me.

We serve founders, leaders, and investors at the frontiers of their work and lives. That could be leading a company that’s scaling faster than they are, finding the courage to leave the startup they’ve poured their life into, or pursuing their ambitions without missing their kids growing up. These frontiers challenge us, awaken our curiosity, and reveal possibilities we hadn’t imagined.

We’re guided by a belief that the company we keep shapes who we become and what becomes possible. A camerado is a fellow traveler on the open road.

Inspired by Walt Whitman’s “Song of the Open Road,” the name captures how we want to support our clients: as companions who see them clearly, challenge their assumptions, and help them discover new possibilities and greater freedom in how they move forward. It’s also the commitment Ryan, Derek, and I are making to each other.

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In Ryan and Derek, I found two partners I hope to build with and learn from for many years to come. We bring different strengths and experiences and are in a similar season of life, raising kids and nurturing strong relationships at home. We share a vision for what this studio could become and a commitment to building it in a way that honors the lives we’re already living.

I’m honored to join with Ryan and Derek because of who they are and what they bring out in me.

I first met Ryan during COVID when he was running coaching pods for one of my portfolio companies, On Deck. He spent fifteen years building venture-backed companies before becoming an executive coach and has since worked with more than 100 founders. He brings a directness and operational rigor that inspire and stretch me. He can take an idea, give it structure, and drive it forward in ways that don’t come naturally to me.

As a coach, he cuts through bullshit with candor and kindness. He’s spent years committed to sobriety and his own inner work, and he brings that same dedication to his clients and our partnership.

We share a desire to build a business that supports a full life, and he prioritizes time to coach his sons’ sports teams and go on adventures with friends. He’s a natural leader and builder, and I’m excited to see him bring those gifts to the studio.

I first met Derek in 2023 through our mutual friend David Spinks. I was drawn to him from our first conversation, and we quickly became close friends. Trained as an engineer, Derek co-founded Ten Percent Happier and spent a decade building one of the top meditation brands in the world. He brings that experience and a product builder’s mind to the studio. He’s organized, methodical, and obsessed with details in a way that I’m not. I’ve watched him build internal tools and processes and found myself thinking, how the hell did he do that?

He’s also a deeply skilled coach, shaped by more than a decade of contemplative practice and years studying Internal Family Systems and other approaches to inner work. With him, I feel a level of support, compassion, and love I haven’t experienced with a work colleague before. I’m free to be myself around him, knowing that I’ll be accepted exactly as I am.

He and his wife, Tess, have a small farm in upstate New York, where they’re building a nonprofit school that helps kids connect with the land and their own humanity. Knowing that our work at Camerado will help support those efforts makes building together even more meaningful to me.

With all that admiration and respect for Ryan and Derek, I struggled to find my own place in the partnership. I kept telling those close to me I had found the best partners in the world, yet I wasn’t sure where I fit or whether I could contribute in the ways they expected. Maybe I was meant to be a solo practitioner after all.

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As we set up the studio and worked toward launch, I spent hours each week in internal Zoom meetings, trying to keep up with Slack threads, learning new processes, and working through partnership agreements and insurance applications. This was on top of a full coaching practice. I was completely overwhelmed.

I was eager to help get the studio off the ground, but had less time for what I love: coaching, facilitating, writing, and evangelizing what we’re putting out into the world. Watching Ryan and Derek ship at a breakneck pace week after week, I felt like I couldn’t keep up. I began to question whether I was contributing enough and felt I needed to do more to earn my seat at the table.

One week in September, I woke up several nights and couldn’t fall back to sleep. I lay in bed, flooded with doubts and questions. Was I cut out to be an entrepreneur at this stage in my life? Could I be the partner Ryan and Derek needed me to be? Should I just go back to being a solopreneur? For the first time in years, I didn’t want to get out of bed and go to work.

Later that week, during one of our recurring meetings, I told Ryan and Derek I wasn’t having fun and was struggling to find my place. I wanted to be their partner, but I felt stuck and unable to build momentum. I told them I wanted to spend more time coaching, teaching, writing, and evangelizing our work. That was where I felt most alive and had the most to offer. Saying that felt risky. I worried they would question whether I was the right partner.

I expected them to push back or tell me that keeping up with the meetings, paperwork, and operational demands was part of being a partner. Instead, they helped me see what I was already contributing.

Derek understood that I was struggling, but wasn’t worried about my place in the partnership. He could already picture me leading the room at our upcoming retreat with Hampton, a private community for founders and CEOs, and knew he would learn from me. He reminded me that being a great partner didn’t mean doing everything.

Ryan pointed to the heart I brought to our partnership, my care and vision for the brand and writing, and my ability to build relationships and bring people together. He saw those qualities as essential to what we were building. What they valued most in me came so naturally that I barely considered it work.

Their support was hard to take in. As we sat together in silence, I started to cry. “We’ve got you, Steve,” Derek said. I felt supported in a way I hadn’t experienced at work before. I didn’t have to contort myself or do everything to earn my place.

It dawned on me that being part of this partnership could help me become more fully myself.

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I want Ryan and Derek to feel that same support from me. I want to challenge them, learn from them, and help them do the work that brings them joy.

In just six months, we’ve built the partnership I had been longing for all these years. We can speak openly about what’s hard, disagree, and repair when we need to. We don’t always get it right, but we’re committed to learning together. We can help one another think through a tricky client situation, build the systems that keep the business humming, or design a new retreat or workshop. I love that we get to be friends, coaches, and colleagues while building something awesome together.

The work we do on ourselves and with one another shapes how we support our clients. We help each other question assumptions, see a difficult situation differently, and recognize when someone else’s expertise would better serve a client. Each client works closely with one of us and can draw on the experience of our partnership and a broader network of trusted practitioners and operators. We help our clients have the conversations they’ve been avoiding, make decisions they’re proud of, and discover ways of living and leading they hadn’t imagined before.

We want to build a special firm and a calm company, with plenty of energy left to care for ourselves and our families. The lives we’re creating matter as much as the work we’re doing. We see ourselves as stewards of a studio we hope can endure, and we want to have fun building it together.

We’re building Camerado around a question: what becomes possible when we approach human development as a shared endeavor? We don’t have all the answers yet, but we’ll keep exploring that question through our partnership, our work with clients, and the experiences we create together.

This is a new frontier for me. I’m excited, a little scared, and proud to be taking this step with Ryan and Derek. I’m grateful I don’t have to navigate it alone. I have my camerados beside me.