Right now, I coach 20 startup founders and executives, lead in-person roundtables for startup peers called Lonely Island, and write a short weekly newsletter on leveling up as a founder called Hoo Boy.
I became a coach on accident after a decade building software companies. After my last company, I was doing some soul searching when a friend asked me if I’d ever considered being a coach. I hadn’t. I had always been frustrated when I asked people what I was good at and they told me I was a great listener… not a great CEO, COO, designer, and so on. I never put two and two together that being a great listener could be a career. But I’m thankful that I did, because I love working with my clients to help them navigate the challenges of being a founder with a bit more help than I had.
On top of the listening part of coaching, though, I’m also a teacher (when asked to be). Just like Richard Feynman redeveloped his own physics from the ground up to better understand how the world works, I’m studying management, leadership, human motivation, and more to better understand—and teach—how these things work.
I’ve been starting businesses since I was a kid, although my judgment has hopefully gotten better over time. My first business was a neighborhood lawn mowing operation called “All American Mow and Blow.” My Mom was gasping for air laughing when she found the flyers with the name all over the street.
In college, I began homebrewing beer and selling it to my friends, but the ATF wasn’t hot on a nineteen year old brewery CEO.
Since then, I’ve spent my entire career making it easier for people to find the knowledge they need to do good work. Most recently, I founded Holloway, a digital book publishing platform where we hoped to build the best reading experience on the web and help authors widen the reach of their books.
Before Holloway, I co-founded Mattermark, a business analytics and database company where we enabled VCs to take a data-driven approach to sourcing investments.
Writing has also been a big part of my career. In 2016, I published The Holloway Guide to Raising Venture Capital, a 310 page book that helps founders both decide whether venture capital is the right path for them and demystifies how to raise money from VCs. I’ve also written several newsletters, most notably The Mattermark Daily (100K+ subscribers at peak).
Work is a big part of my life, but what about the rest?
I live in San Francisco with my partner, Kate. We met at our friends’ wedding, spent a year long-distance, and moved in together thanks to the pandemic.
I’m a Humanist. That means I believe it’s up us people to give meaning to our lives, and we don’t need to invent a god to do that for us. Kurt Vonnegut believed, “We are here on Earth to fart around, and don't let anybody tell you any different,” and I don’t think he’s wrong.
Friendship is huge for me. While everyone knows “it takes a village” to raise a kid or however the quote goes, I believe a village full of friendships with real depth is the real stuff of life.
I love a good conversation over a few beers, but I’ll settle for coffee, too.
I love reading (and talking with my friends about what we’re reading). When it comes to fiction, epic science fiction and fantasy novels are my favorites. In 2022, I’m working through Ian M. Banks “Culture” series. I’m a huge fan of The Expanse series by James S.A. Corey, Brandon Sanderson’s Stormlight Archive, and I’m anxiously awaiting Patrick Rothfuss’s third book. My latest favorite non-epic is Callaghan’s Crosstime Saloon.
As for non-fiction, I’m really into history, human psychology and motivation, and reading about whatever it is I’m struggling with personally. In 2022, I’m reading a lot about back pain, how to be a great partner to Kate, what makes a good vs. bad manager, the nature of genius, and the origins of human civilization before Greece and Rome.
I also love real-time and turn-based strategy games. I’m currently playing a lot of Age of Empires IV, and I’ll always be hooked on the latest version of Civilization. If you want to play, my gamertag on Steam is SparksZilla.
I have cartoon tattoos. One is of Calvin and Hobbes and the other of Merlin from The Sword in the Stone. Both are reminders not to take myself too seriously.