What a Decade of Entrepreneurship Taught Me

Today marks a decade since I left my comfy corporate job and ventured out to start something new with Paige McPheely. I vividly remember turning in my company car and writing a small check to start our new venture, making a clear and decisive trade — certainty for uncertainty. A scripted path for a wild ride into the unknown.

Not only was it a leap into entrepreneurship, it was also the start of a decade of intense personal growth. Paige and I each had an infant son when we started our first business, and in the following years, we would go on to create families with six (collective) sons, grow into six- and then seven-figure revenue, and pitch a software concept at High Alpha’s Sprint Week to get pre-seed funding for our second business (which we later merged with the first).

Ten years later, I’m reflecting on how this intense, exciting chapter has shaped me. For those of you leaning into your own ventures, here is some of what I’ve learned along this wild ride:

  • You’re not going to get everything “right.” There is no rulebook in entrepreneurship, and try as you may, you’ll never get everything “right.” Instead, you’ll triangulate and gather feedback, you’ll test and fail, test and fail, test and succeed, and you’ll find it’s more about being committed, agile, and open than it is about getting everything “right.”
  • Your best compass is knowing your values. The moments I have felt most clear as a leader were when I sat with my values and made decisions from that place, vs. from “I should…” or “others expect me to…” There are peaks and valleys in building a business, and staying connected to your values will help you navigate the toughest terrain.
  • Success is not all “up and to the right.” It’s tempting to wish for growth upon growth, with your success charted as a perfect hockey stick up and to the right. But in reality, there are pandemics, customer concerns, employment issues, personal doubt, cash flow issues, and difficult decisions that dot the journey. There are also inspiring team sessions, innovative breakthroughs, strong relationships, and huge wins to celebrate. Progress isn’t linear. Celebrate at the peaks and stay persistent in the valleys.
  • Build a trusted inner circle. Leading can be lonely. (I’ve thankfully been co-leading with Paige for most of the last decade!) Surround yourself with coaches, mentors, a group of peers, and dedicated team members. Ask for feedback and be open about what you want and where you struggle. The journey is easier when you realize you’re not alone.
  • You are more valuable than your imitation of someone else. There is not a “mold” for leadership. I’ve tried and failed to match my leadership style to someone else’s or to a “norm” I accepted somewhere along the way. It’s like wearing the wrong clothes – uncomfortable, itchy, and ill-fitting. Invest in a coach and gather feedback from your circle. What are your unique strengths as a leader? Learn and lean on these. You can only build the company you want to build if you’re leading as you.
  • An underrated skill is asking great questions. I thought a strong founder and leader had to have all the answers. But I’ve realized a much more powerful leadership skill is asking great questions. Instead of “Here’s exactly what we need to do,” ask “Why do we do it this way?” Instead of “This will add value for our customers,” ask your customers, “What do you most value? What keeps you up at night?” Then open your ears and really listen for the answers.

I’m celebrating this past decade and all the ups and downs that have defined this wild, invigorating journey. I’m consistently grateful for Paige, the exceptional people I’ve had the chance to work with along the way, and the opportunities that lie ahead.

Here’s to the next 10 years!