Off the Bullet Train
By now, it’s old news that I passed the baton as CEO of Nitrogen (which started life as Riskalyze) on December 4, 2023. Our new CEO is an amazing software veteran and awesome person. I’m really excited about continuing to help an organization and team that I love continue to succeed, while also exploring some new frontiers.
I’m sure I was far from a perfect CEO during my twelve and a half years at the helm, and I’m sure others have found a better way to do it, but after we launched a product and had customers to serve, every single day felt intense. I had a rigorous schedule mapped out on my calendar from 4:45 in the morning to ~10:30 at night when I would fall asleep.
To be clear — some of that schedule was spending time with family, working out, going to movies with my kids, or reading over a cup of coffee.
But a few weeks after we made this decision with the board, my wife said to me “it feels like we’ve been living life on a bullet train…it’s been amazing and wonderful, but I’m actually looking forward to stepping off for a bit.”
I agree with her.
I’m certain I will jump back on the bullet train again in the future — perhaps a really fascinating organization comes along with a compelling role where I could make a huge impact. Or more likely, because I start a new company from scratch.
But in the mean time, I’m trying to be very intentional about structuring 2024 to take advantage of this time off the bullet train — splitting my time roughly into thirds.
Pouring into my family.
My wife is an incredible human being. She has been a true partner in every part of starting and leading a company. She’s been willing to listen to all the problems, give good advice, and yet she doesn’t get nearly enough credit for the successes. She is in school to become a licensed marriage and family therapist with an emphasis in adoption trauma, and she will be between degree programs this summer.
Our kids are senior, junior and freshman in high school this year. One will launch into college this fall. The timing is amazing for me to really create some impact on them before time robs me of the opportunity.
So Cacey and I will do some travel this year that we’ve been wanting to do. I’m mapping out more ski weekends with my boys, and a few more dates with my daughter.
Also under this category is finishing our house — we’ve been building our long-term family home in Idaho, and we hope to move in this March. With a little more time on my hands, I’m coordinating the hardscaping and landscaping contractors.
Looking out at the world and learning.
I’m allocating some serious time to exploration and learning. I’ve been laser focused on one thing for over a decade, and the world has changed a lot since then.
A few of the things that I’m intrigued by…
- Becoming really advanced with Microsoft Excel. I’m a power consumer of Excel models, but I’m definitely a beginner at creating them.
- Dipping my toe back into coding. My coding skills are stuck in 1999. I’m using Udemy to raise my understanding of a few things like Python, React, AWS and PyTorch. I’m definitely not trying to become a full-fledged engineer, but my technical background has served me well in the past.
- Spending time with generative AI. I spent the 2010s as a bear on artificial intelligence, and am bullish on it for the first time in my career. It’s the new platform and is going to redefine how we interact with computers and take human creativity to a new level.
- Reading. I’ve loved books since I was five years old. I’ve created long lists of books on topic areas I want to deepen, areas I want to broaden, and fascinating people I want to learn about.
- Watching interviews. Speaking of fascinating people, I’ve always struggled with podcasts because I’m a visual learner. Then I stumbled upon David Perell’s How I Write interview series, which has such beautiful production quality. I’ve absolutely loved his interviews with Morgan Housel and Marc Andreessen so far. I’m going to consume more of this format, because it works for me.
- Writing. Writing down your ideas can be a great way to reason through things and share those learnings for others to benefit from. I’m not planning on being prolific — no “blog post a day” pledges from me — but I’ve got a few things in the works that I’ll share.
- Non-profit work. I’m going to continue allocating time and energy to making the world a better place. Orphan care, adoption and foster care remains a big area of focus. I’m volunteering at our church with finance and administration. I’ve also joined the board of Mountain States Policy Center, a nonpartisan think tank dedicated to advancing the free markets that have built this great country and driven the prosperity we enjoy.
- Deep diving into different markets and opportunities. I have a blizzard of ideas for new companies that I’ve been writing in my notebook for over a decade. Most of them probably aren’t good ideas. I’m really excited to deep dive and figure out which ones might be interesting.
Helping 4–5 great companies learn how to grow and scale.
I will be spending time helping Dan and the rest of the team at Nitrogen continue to empower the world to invest fearlessly, and given how much I love that organization, I’m really excited to do that.
I’m also going to invest a bit of time this year helping out about 4–5 other great companies — either technology or wealth management firms that have intriguing leaders or visions for the future.
- I was already an investor in one of these companies before the transition, and I’m going to serve as a Strategic Advisor to that firm. We’ll announce it at some point in the future.
- I’m doing some leadership consulting, helping firms to build / iterate / shape the “strategy pyramid” that I used to scale Riskalyze — from figuring out your mission, to determining your core values, to building out a path to your goals, and figuring out how to align that with your go-to-market strategy — and helping CEOs and leadership teams form consensus around those things.
- I’m doing some CEO coaching, doing 60–90 minutes every two weeks helping CEOs think through challenges, and come to strong conclusions about what they need to do to help their organizations succeed.
This is new for me.
I’m getting my “land legs” again after stepping off the bullet train. I’m excited to spend time pouring into my family, deep in exploration, or helping a few companies to achieve great things.
Hopefully I’ll learn some great things this year that I can leverage for the rest of my career and life. I look forward to sharing many of them with you.
