For more than a decade, my life moved at the speed of a bullet train.
When I look back at my time with Nitrogen, the company I founded as Riskalyze and ran as CEO, it feels like I worked four different jobs over the course of 12 years.
After first figuring out the market need and building the initial product, the next step was figuring out how to actually sell it. Almost overnight, we were in hypergrowth and my job was scaling the business to keep up. The final phase was all about developing the infrastructure needed to support a large, mature organization.
All four of those phases were interesting and intriguing and challenging and rewarding — all at the same time.
My typical day as a CEO would start at 4:45 a.m. It was the only way I could make it home by 6:00 p.m. to see my kids and spend some time with my wife before I picked things back up to prepare for the next day. Email was like a massive multiplayer online game that I was consistently losing at. I traveled every other week.
It was the life I chose and I don’t have a lot of complaints. But it was intense.
In the midst of it all, I remember telling my wife, ”I don’t know what the finish line looks like for this company, but whenever I hit it, slap me if I do not take six months off.”
Now Arriving: The Finish Line
When Hg Capital, one of the world’s leading software investors, recapitalized our company in 2021, it marked a big shift. Instead of me running the company at the behest of a number of minority shareholders, we were now owned by a single private equity firm. They were an incredible pleasure to work with, and have remained excellent stewards of our culture.
There comes a time when every leader has to ask themselves if they are the right person for the current moment. As the economic cycle shifted and the strategy for the business began to change, we started laying the groundwork for what would be a BIG change — a transition to a new CEO. As emotional as it was to think of stepping out of that role after twelve and a half years, it was clearly time. We hired Dan Zitting in August 2023 and announced the change in November. On December 3, I officially passed the baton.
My wife thankfully never had to slap me, but she did give me some parameters as we prepared for the next chapter.
She would be graduating from her degree program in June 2024 and wanted to travel before her next phase began. Our kids were getting older, which meant it could be the last opportunity for the entire family to take some time off together.
“I really think you need to take the year off,” she said.
“Like, the whole year?” I asked. Six months already seemed like a long time.
“Yes,” she said, and we circled October 2024, after our return from a big “graduation trip” to the Mediterranean, as the time for when we would both start taking our next steps into the future.
Suddenly, I was at the finish line. The bullet train had stopped for the first time in 12 years, and it was time to get off.
Learning to Stop Moving
Even while I was working, the holidays would naturally offer a bit of a lull and a chance for some strategic planning.
But this year, I didn’t have anything to plan for. With no backlogged emails or last-minute projects to catch up on, it was pure rest and relaxation. We had a lot of fun together as a family.
When the new year started, however, I realized that my body hadn’t gotten the memo about the career transition. I continued to wake up early every morning. While I used to carve blocks of time in my calendar for reading, having coffee, working out, and showering, I was now just puttering around after getting all of those things done by 7:00 a.m.
I’d find myself sitting at my desk, shaking my head, and thinking, “What do I do?”
I threw myself into a few different things. I took an Excel class online to get into advanced financial modeling. I started doing a little bit of consulting. A few private equity firms reached out with very flattering offers to join them, and sit on boards of some pretty compelling companies. So yeah, I was a bit of a maniac, I guess.
But deep inside, I knew that I wanted to start another company. I enjoyed the building phase, creating solutions to big problems, and scaling up a company that served customers. I knew I had at least one more of those still in me.
It wasn’t long before I was trying to figure out what it was that I would launch. I remember saying multiple times, “I need to get ahead of it.” I was already thinking about who I needed to hire so we could start building a product. By mid-February, I was frenetically making lists of all the things I could do in anticipation of November. I was ready to step back onto the platform and board the next train.
A call from a mentor changed all of that.
“I thought you said that you were taking a year off the bullet train,” he said. “What kind of break is this?”
He asked me if I was familiar with the concept of the Sabbath, the concept in our faith that God gives a period of time to rest, recuperate, and gain perspective on our life.
“You’ve been given the gift of a Sabbath for an entire year. Why would you waste it by ‘getting ahead of it?’” he asked.
It wasn’t exactly a slap across the face, but it was the wake-up message I clearly needed. After we got off the phone, I went for a walk.
He was totally right.
I decided I wasn’t going to do any of the things I had been talking about. I could think about them, I could write about them, I could sketch them, I could even open up Keynote and build some slides to practice telling the story of the new company, but I wasn’t going to pitch it to anyone.
I wouldn’t raise any money, wouldn’t hire anybody, wouldn’t incorporate, and wouldn’t build any infrastructure.
I wasn’t going to work.
Freeing Constraints
It was a difficult constraint for me, but it became freeing. I found whole days to just sit and dream; to sketch out my thoughts on the whiteboard.
By not diving right in, I realized that I didn’t have to repeat how I founded Riskalyze. While the company was successful, I founded it with a pretty basic understanding of what we were building and where we were going. A lot of it was improvising and learning along the way.
I now had the time to think through everything: to truly map out what a company could look like and where it could go.
The constraints also gave me more space and bandwidth for the things that matter most in my life. All three of my kids were in high school and I got to spend a lot of time with them. My wife and I got entire afternoons for hikes and bike rides, something we had never done before.
I even had time left over to dedicate towards helping other entrepreneurs who reached out for advice. Lots of people helped me when I was still figuring things out. This was my chance to pay it forward.
My wife and I capped it all off with a trip to Europe alongside our friends Brian McLaughlin, who had recently sold his advisor fintech company Redtail, and his wife, Tanya. While I had done some fun vacations in the past 12 years, this was the first time I didn’t have to schedule any time to sit in a hotel room to make calls. The only check-ins were with our kids; otherwise it was three weeks of going around to different islands in the Mediterranean without a care in the world.
All Aboard
My first pitch meeting for my new company, Contio, an AI operating system for meetings, was scheduled for November 1, 2024. We closed our seed funding six weeks later.
I’m definitely back on the train, and it’s fantastic! Only this time, it’s moving at a different speed.
I still love the process of building things that customers love. I’m back to leaping out of bed every morning at 5:00 a.m. because I really believe AI has the potential to fix what’s broken about meetings.
But the greatest thing that I learned during my time away was that perspective matters.
There is so much value in taking a step back to get a different angle and look at the whole picture. I believe it made me better — not just as a husband and a father, but hopefully as a leader and a builder.
I recognize that not everybody has the opportunity to do something as crazy as take an entire year off. It was an incredible and rare privilege. But the same lessons apply whether your break is a year, a month, or even a couple of weeks.
My time off taught me so much about the value of time. And now I’m building a new company that helps others use their time more effectively.
Life… work… it can all become a blur when you’re speeding along. If you want to see your next destination clearly, sometimes you have to stop moving first.
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