In late 2019, I started working on an audacious project to bring high quality and affordable healthcare to every American.

In the spring of 2018 I lived on a Buffalo Ranch in the Canadian Rockies and became friends with a singing cowboy named Leo. When the snow melted, I camped and surfed my way to San Diego.

In 2017 I drove out of New York City with my backcountry ski gear. I spent the next few months skiing and living along British Columbia’s Powder Highway.

In 2016 my cofounders and I led our startup, Hightower, through a merger with VTS and effectively doubled the size of the company overnight. The Wall Street Journal reported on the deal.

Crain's New York named our young company one of the "Best Places to Work" in 2015.

I moved from Seattle to NYC in 2014, sharing an apartment with my cofounders at 147 Mulberry Street in Little Italy.

Boarding my flight to NYC, I was radioactive enough to set off dirty bomb detectors. I had to carry a note telling Homeland Security I wasn't a terrorist.

In 2013 I got divorced. I spent nine months sleeping on a couch in my cofounder's living room.

I was also diagnosed with cancer in 2013. It was a tough year.

I studied customer development with Steve Blank in 2012. His guidance and advice changed my life.

In 2011 I started an innovation consultancy with one of my best friends. We worked with Nordstrom Labs and the Microsoft Garage to launch products and innovation practices. We were very good at this.

My writing on startups went viral, eliciting the praise and scorn of the internet. The most surreal moment was going to Linkedin and seeing something I wrote as "trending on the web".

In 2010 I facilitated the first Startup Weekend events in the Middle East and Central America. This is some of the most rewarding work I’ve done.

In 2009 I dropped out of a master’s program at the University of Washington in Human Centered Design.

In 2008 I hit 47 miles per hour on a bicycle with a bee in my spandex. I didn't know about the bee until the bottom of the hill.

In 2007 I joined Redfin and was laid off when Lehman crashed. I nearly went broke, coming home one day to find a foreclosure notice on my condo. I tore it down before any (more) of my neighbors saw it.

I was married in the town of Ganges, a small haven off the coast of British Columbia.

In 2005 I crashed my motorcycle.

In 2003 I opened a music production studio and arts space in Seattle, where I got to work with incredibly talented people. When the business failed, I ended up delivering pizzas for nearly a year. This taught me a lot about dealing with failure and setbacks.

In 1999 I snowboarded off a cliff at high speed (on purpose) and hit a tree before I hit the ground (not on purpose). I actually hit several trees and spent the next few months in pain, on crutches, and smoking lots of pot.

I didn’t like high school and graduated in three years instead of four.

In 1994 Ms. Dooley called me out in front of the entire class for filling my math workbook with songs and poetry.

In 1990 I got into the Edmonds School District's "gifted" program – after cheating on the test. On orientation day, I stapled my finger.

In 1988 my parents signed me up for a ski lesson, transforming me into a gravity-powered adrenaline junkie at the ripe age of six.

In 1984 I went to Disneyland for my birthday. They were celebrating Donald Duck's 50th anniversary with "Happy Birthday, Donald!" parades. I thought these parades were for me.

I was born on June 11th 1982, in Seattle’s Capitol Hill neighborhood.

Writing, Talks, and Interviews

Building a company, building a team, and nailing a merger

The one investment most startup founders don't make early enough

Donald DeSantis on discovering what you want

Donald DeSantis on the absolute power of product market fit

Designing your career path

How I fought through cancer to launch my startup

Thoughts on turning 30 in the tech biz

What startups can learn from a crime boss

Everything I need to know about startups, I learned from a crime boss

What being hopelessly single taught me about pitching tech celebs

About

Writing, Talks, and Interviews