Why I’ve Decided to Start Coaching Startup Leaders

I spent 7 years running my last venture-backed startup. I don’t know if I would have survived without the help of the leadership coaches who came alongside me and helped me transform the way I understood the role of a leader. The work changed me as a person, as an adult, as a partner, and as a father. I’m humbled to begin my own exploration of how I might help other leaders in a similar fashion.

Too many companies fail. Too many founders feel alone in the process. Too much misalignment exists among CEO’s, their leadership teams, their employees, their boards, and their investors. Today begins my earnest journey of pitching in to more directly facilitate a large-scale change.

While the title ‘coach’ still weirds me out,  I’ve decided to roll up my sleeves and begin coaching. (I’m anticipating coaching alongside angel investing and exploring additional founding projects, but more on that later.)

During my first few years being a venture-backed CEO, I lived under the common misconception that I needed to have all the answers. My way of managing was to have others bring me problems, ask them to share data or recommendations, and then make the decision. I thought the job of a CEO was to make decisions alone.

What’s more, I thought CEO was suppose to be a solitary job. After all, I couldn’t share all the information with my team, like how much money we had in the bank or who made how much money, so how could I possibly trust anyone but myself to make informed decisions?

This fit nicely with a lifelong internal schema wherein I believed that, even with people around me who loved me, I was ultimately alone. And that when things were hard, I needed to trust only myself.

I grew up in a family where my parents, although well-intentioned, were too preoccupied with their own suffering to hold space for me. At an early age, I learned that it was my job to be the stable one in the family, the one who held the family together.

I’m not alone in this experience.

In fact, I’m shocked how many startup CEO’s are children of a similar marriage. Kids who were forced to grow up too soon. When you come up in a family where you’re asked to take on leadership responsibilities at 6 or 8, the role of CEO fits nicely. At least the role that many first time founders think is the CEO role. Taking on everyone else’s problems. Sacrificing one’s self for the safety of the tribe.

The mold fits. Bright young person, takes on responsibly at an early age, grows up to be trusted with the responsibility of leading a company. The problem is that the pattens we learn in such an arrangement bite us in the ass down the road. They might cause others to turn to us as co-founders or to ask us to step up in a CEO role. They might even catch the eye of opportunistic venture capitalists who, typically subconsciously, like entrusting capital to founders hungry for paternal approval. But when it comes time to really lead, these patterns cause big problems.

When we lead believing we must have the answers, when our sense of self is tied up in pleasing our investors or employees, when we lack the ability to care for our own well-being before attending to the company, we end up unable to show up as the leaders our companies need.

At least, that was the case for me.

I wasn’t trusting my team. I wasn’t giving them clarity on what mattered.  I was living inside my own head. Yes, I held weekly leadership meetings and all-hands. But I didn’t invite my leaders into our deepest challenges and questions. And I didn’t share information transparently with the entire team. As a result, I built a culture that left me isolated as a leader and that reinforced the childhood messages I’d carried about my own aloneness.

The pattern began to shift when I started to work regularly with an experienced CEO coach. He helped me to see the way I was complicit in creating a company culture that I despised. And he showed me how that approach was having catastrophic consequences for my family, my sense of well being, and my health. Working with a coach, and a therapist, helped me to see that I was playing out these lifelong patterns in my role as CEO, and that if I didn’t learn to move beyond these patterns the company would not survive.

This is not work that one can do alone.

When I dug in on the work, the results were life-changing for me. I learned how to open myself up to the team.  I learned I wasn’t alone.

For example, when our revenue model struggled early on and we had to reshape our entire pricing and sales model, at the behest of my coach, I stepped out of my usual pattern of locking myself in a conference room with the financial model. Instead, I told the team we needed to make a shift. But that I didn’t know what we needed to do. I asked them to pull together all of the data and learnings of the last six months. The entire board and leadership team, along with two outside advisors, gathered for an all-day brainstorming session offsite. We invited the board members, the advisors, and the leadership team into the difficult questions. And together we devised a path forward. I remember how nervous I felt that morning; that day represented a tremendous shift in my way of being a CEO, and I think it was one of my single best days on the job.

Coaching saved me.

More than giving me strategies and tactics for the hard challenges of building a company (which it also did), coaching helped me to evolve as a person and a leader. It gave me space to step back from the crazy week and reflect on how I was experiencing what was going on, why I was showing up the way I was, what was driving me, and what the team really needed.

Over time, coaching also helped me to explore how to align the business with the life I wanted for myself and for my employees. It taught me as well how to invite the team into such questions. The result was a massive shift in the company, from the isolated, top-down experience I outlined above to a closely-knit team of people building a legacy business together.

I’m deeply excited to be stepping into coaching myself. Finding a great CEO coach is really fucking hard. And there aren’t enough ex-founders doing the work. It is also a field fraught with charlatans. 99 out of 100 people presenting themselves as coaches are full of shit. They’ll take your money, prey on your imposter syndrome, and provide no real assistance in the journey at hand. I know I have so much to learn, but even now I know I can show up with an open heart and a deep, honest care for the founder in front of me. I know I can do good and not harm. And I know that much good is needed.  So I’m deeply excited to be beginning this work, and many thanks to the founders who have already stepped up as my early partners on this journey! I wouldn’t have had the courage to begin without your trust.

I’m excited for the road ahead. There’s never been a time where we more critically needed heart-lead, human-first companies. Our kids need more examples, not fewer, of companies where the leaders, teams, and investors are aligned. They need to see their parents going to work in places where their hearts are invited into the craft.

Founders and leaders have tremendous challenges at hand. Yes, there’s currently a lot of capital out there, but the expectations and responsibilities are tremendous. We’re handing nearly unlimited resources to young founders but leaving too many tremendously under-resourced. We may teach them how to hire, but we don’t teach them how to lead. We teach them how to scale teams, but not how to scale themselves. We teach them to bring their minds to their work, but not how to align the work with their hearts. And then we wonder whey we end up with the toxic cultures and multi-billion-dollar dumpster fires we’re seeing of late.

I am deeply excited for this work. If there’s a way for us to work together or partner together in any part of this work, please reach out.

Wishing you peace today on your own journey.

Matt