Do the crazy thing


I build high performing teams. 


In 2018 I spent a month living on a Buffalo Ranch in the Canadian Rockies and became friends with a singing cowboy named Leo

In 2017 I purchased a property in one of my favorite places: Nosara, Costa Rica.

In 2016 my cofounders and I led our real estate tech startup through a merger with one of our largest competitors. 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.

My cofounders and I moved from Seattle to NYC in 2014. We shared an apartment in Little Italy at 147 Mulberry Street. 

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. 

In 2010 I set a goal to own 300 things or fewer. I got close, but it turned out harder than I expected.

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".

I teamed up with a few friends to create the first “live” party in That was a big deal for a few weeks.

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.

I dropped out of the University of Washington twice. Once as an undergraduate Art Major. The second time as a master’s candidate in Human Centered Design.

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 subsequently laid off during the 2008 crash. I nearly went broke, coming home one day to find a foreclosure notice on my condo. 

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

In 2005 I crashed my motorcycle. I was young, dumb, and lucky.

I delivered pizzas for nine months. It was a good gig.

In 2003 I opened a music production studio and arts space in Seattle, where I got to work with incredibly talented people and some incredibly dangerous ones

I studied music production in college and promoted hip hop shows. I also played keys and rapped in a live hip hop band based out of Bellingham, WA. 

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 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, on Capitol Hill in Seattle WA.


Writing, Talks, and Interviews


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

Giant and Crowns, January 5th 2018 


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

Fast Company, April 4th 2017


Donald DeSantis on discovering what you want

Entrepreneur Takeover, June 20th 2015


Donald DeSantis on the absolute power of product market fit

Growth Hacking Podcast, June 11th 2015


Designing your career path

Design Driven NYC, April 17th 2015


How I fought through cancer to launch my startup

Inc, February 5th 2015


Thoughts on turning 30 in the tech biz

Geekwire, June 11th 2012


What startups can learn from a crime boss

New York Times, January 17th 2012


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

GigaOm, January 7th 2012


What being hopelessly single taught me about pitching tech celebs

Geekwire, November 6th 2011