Hey there

I’m an experienced executive who enjoys applying systems thinking to strategic challenges, as well as designing product platforms and the organizations needed to build them.

I’m currently the CEO at travel-tech company Wanderu, helping millions find and book sustainable travel.

In my writing, I mostly explore how industries, technologies, and organizations evolve as complex systems—and what that means for decision-making, strategy, and adaptation.

I’m also a sometimes-consultant, author, speaker, investor, conference organizer (most recently the PageBreak conference), and startup advisor (currently advising Holloway, Doriot, and PressBooks). Ex-O’Reilly Media, ex-Safari, ex-getAbstract. I’m also a very proud father of two wonderful kids!

Recent posts

Remembering Ben Carnevale

5 minute read

I was honored to give the eulogy for my uncle, Ben Carnevale, at his funeral mass on June 14, 2025

When Tech Goes From Disruption to Deployment

8 minute read

3 Reasons why we’re well into the final ‘deployment’ stage of the technological revolution begun nearly 50 years ago with the first microprocessor, and techn...

Going Home

2 minute read

Why I left a great company to become a work-from-home dad

Ten Great Books for Working More Mindfully

32 minute read

A list of 10 books I’ve found especially useful over the past year in trying to both understand what mindfulness really is, as well as find tactical advice f...