1. What have you found most challenging as a leader?

Building a repeatable process to ensure the decisions I am making are the best for all the people impacted by those decisions (clients, team, and shareholders). Getting that balance right is incredibly hard.

2. How did you become a leader? Can you please briefly tell the story?

In high school, I started a tech website that exploded in popularity, and I was suddenly running an informal team of 20+ people. I was just a kid and I had to learn so much. I was leading adults and kids, dealing with high levels of drama, and interacting with the media. It was wild and changed the direction of my life.

3. How do you structure your work days from waking up to going to sleep?

I enjoy my flexibility, so I keep it loose. I pick the three most important things I can do to move the company forward the night before. And I choose my workout routine for the next day, depending on the weather.
In the morning, I jump right into work and start with one of the most important items that sound exciting to me. I eat my first meal of the day at around 1000, and after that, I catch up on emails for about an hour. I alternate between biking and strength training every other day. After that, I pick another of the most important tasks and dig in. I finish up around 6 pm and go hang out with my family.
Luckily I am starting a new business, so that I can limit meetings and phone calls to Mondays. When running larger organizations, I tried to restrict calls/meetings to three days a week and time-boxed them to ensure I had enough time for deep work.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

I was recently reminded of how important it is to repeatedly communicate the vision of where you are going in a way that is specific to that stakeholder. That is something I've learned in the past, but I forgot how many times you need to do it to ensure they really hear you and absorb it.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

"Leaders Eat Last" by Simon Sinek had a massive impact on my leadership style. It articulated my vision of leadership and helped me see all the connecting lines between the pieces. Before that, I had been nervous about my style as it seemed so different from what you read or see in the news. It comforted me to know that my "servant leadership" style was equal to those, and I could fully embrace it. I gave a copy to every employee to ensure they understood our mindset.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Get an excellent executive coach. I can't stress enough how helpful it is to have a non-stakeholder to help you pick apart your decisions, communication, and weak areas.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

I became a C.E.O. of a decent size company when I was 26. The company was going bankrupt, and I was under immense pressure to turn the ship around. It was a massive shock, and I was under tremendous pressure. In hindsight, it was a pretty insane transition as I scrambled to learn to lead a small team. I was pretty hard on myself during this period and didn't feel like I was measuring up.
Many years later, it was an incredible moment when the team I built started to take up the reigns. There was a moment when they told me it was time to leave their "kitchen," I was scared but also thrilled because I had built an organization that was leading itself. It was one of my favorite moments because I realized I was doing a good job after many years of feeling like I was always behind the curve.