Welcome, Matt

Welcoming our newest Founder Coach, Matt Thieleman

Welcome entrepreneurs! I’m so glad you’re here.

It’s been a minute since my last post, and to be clear, I’m not breaking my newsletter sabbatical. I still plan to dedicate my writing efforts toward a larger project (which is now nearing 200pg).

But we have some big Inside-Out news I wanted to share: we’re welcoming our fifth coach, Matt Thieleman to our ranks!

Matt is the founder of Golden Bristle, and the author of This is Coaching. Matt I first met years ago, when he was running one of the largest executive coaching networks in the venture space, Pilea. Now I’m immensely excited to share that Matt will be joining us both to support early/mid stage founders in scaling consciously, and in helping IO codify the structures we use to support all our founders.

So, for those of you who haven’t yet met him, I’ll leave it to Matt to introduce himself. And if you want to reach out to Matt, the link is at the bottom.

Welcome, Matt!

Growing up outside Detroit, I was what you might call the "achievement kid" - valedictorian, athlete, the one who checked all the boxes. On paper, I was successful by every conventional measure. But underneath those accomplishments lived a persistent question: "Is this all there is?" Despite the accolades, I often felt like I was chasing something I could never get, falling further behind even as I accomplished more.

This disconnect wasn't surprising given my background. In my family, success had a very specific definition. I was surrounded by people who valued steady jobs at large organizations - the kind that provided security and a clear path. Entrepreneurship wasn't just uncommon; it was something "other people" did - people who were somehow different from us. The unspoken belief was that building your own business was for a different class of people, while we were better off playing it safe. 'That's not for people like us' was the subtle message that shaped our choices.

So when I found myself drawn to startups and eventually founding my own ventures, I became something of a family anomaly. I was stepping outside the well-worn path of security that had been modeled for me, into territory that felt both exciting and uncertain.

The Question of Belonging

This uncertainty followed me into my early professional life. Even as I supported startup organizations with marketing, I constantly wondered whether I truly belonged in these spaces. Entrepreneurship seemed like some exclusive club with unwritten rules and secret handshakes I hadn't been taught. This question of belonging - "Am I really supposed to be here?" - has been a persistent theme throughout my journey.

Ironically, it was through this feeling of not quite fitting in that I stumbled into my true calling and demonstrated how much I really am an entrepreneur at heart. Without any formal training or experience, I decided to start teaching meditation and mindfulness (before I had even established my own practice). This spontaneous leap led me to speaking on mindful leadership, which unexpectedly resulted in someone asking me to coach them.

I still laugh remembering my first coaching client. I literally Googled "how to onboard a coaching client" minutes before our first call. Despite my complete lack of preparation, something natural emerged in that conversation - a capacity to listen deeply, to see someone's potential when they couldn't yet see it themselves, and to create a space where transformation became possible.

Finding My Tribe

In the Inside-Out team, I'm what you might call a "coach-founder" rather than a "founder-coach." While many of my colleagues built businesses before becoming coaches, my journey went the opposite direction - I was a coach first, before stepping into the CEO role at growth-stage startup. This reverse trajectory gives me a unique perspective on the challenges leaders face, having observed them first as a coach before experiencing them firsthand.

My accidental entry into business building revealed what had been missing in my professional life: the opportunity to support others in connecting with their deepest wisdom while doing the same for myself. The more I coached, the more I recognized patterns in both my clients and myself - the ways we hide from our power, the stories we tell to keep ourselves small, and the possibility that emerges when we choose differently. And running a company only intensified the opportunity to discover my blindspots.

Even now, it's easy for me to feel like an impostor, wondering whether I bring anything worthwhile to the table, curious if I'll ever truly fit in. But when I'm with Ryan and others on the Inside-Out team, I realize I belong precisely because we're all asking these questions together.

Supporting Founders Today

My startup coaching entry came from a coffee meeting in Detroit with a VC. I'd invited him to chat, and when he asked what we were doing there, before I could think, I blurted out that I believe every founder in the world could use a coach and I want to make it happen.

That impossible goal has fueled the last 6 years of my life and will continue to. Not because there is virtue in coaching itself but because of what it creates. Through inside-out leadership coaching, leaders experience a profound transformation in their relationship with themselves and their work. They develop the capacity to recognize and work with their patterns rather than fighting them, transitioning from fear-based reactions to purpose-driven creation. This inner alignment creates a ripple effect throughout organizations, fostering cultures of trust where vulnerability and accountability coexist.

My journey has taught me that coaching isn't about having answers - it's about creating environments where people can discover their own wisdom. It's not about fixing problems but about seeing possibility. It's not about making small improvements but about creating what once seemed impossible.

Today, my work focuses on supporting visionaries and leaders who know they're meant for more than just checking boxes. My approach centers on helping people rediscover their innate wisdom and power so they can create from that place.

If my story resonates with you - especially the parts about not quite fitting the mold or questioning your belonging - I'd love to connect. The world needs your unique expression, and I'm here to support you in bringing it forward.