Do the crazy thing

About

I build high performing teams. 

 

In 2017 I left a company I started and grew to 200+ people. I now spend most days writing or coaching startup founders, splitting my time between the mountains, the ocean, and in Brooklyn with my cat, Kauai.

I spent the first part of 2018 living on a Buffalo Ranch in the Canadian Rockies and became close friends with a singing cowboy named Leo

In 2013 I cofounded a technology company and in 2016 led it through a merger with our largest competitor. I am incredibly grateful for this experience and the people who came into my life as a result.

Before moving our headquarters from SoHo to Bryant Park, I skateboarded to work through the East Village and Nolita nearly every day. I only crashed once, right in front of the uber-trendy Bowery Hotel. If you're going to crash, make it count. 

Crain's New York named our young company one of the "Best Places to Work" in 2015. If you're going to start a company, make it a great one. 

I moved from Seattle to NYC in 2014. My cofounders and I shared an apartment in Little Italy at 147 Mulberry Street. We had no customers, no employees, and no office. We had no idea how quickly that would all change. 

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 were key to the success of the company that followed. 

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. I'm happy to say that the company is still going strong and employs some of the best software developers in Seattle. 

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 Turntable.fm. That was a big deal for a few weeks.

In 2010 I brought some of the first Startup Weekend events to the Middle East and Central America. This is the most rewarding work I’ve ever 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 HCI.

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 to scale their real estate sales operations. I was laid off during the 2008 recession. This accelerated a rewarding but challenging career pivot from sales to product. Over the next 18 months I nearly went broke, coming home one day to find a notice of foreclosure on my condo building's entrance. Printed on it were my name and unit number. 

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

In 2005 I bought a motorcycle and crashed it – three times. I got good at fixing motorcycles. Later that year a friend died in a motorcycle crash. I sold my bike. 

I delivered pizzas for about nine months and thought it was a great job. The unbelievably wealthy neighborhoods were the worst tippers, followed closely by the unbelievably poor ones. Folks in the middle were the most generous. 

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. Many went on to find great success, including wins at the Oscars and Grammys. 

I studied music production in college and promoted hip hop shows. Around this time I also played keys and rapped in a live hip hop band based in 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 tore my MCL. I 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 my math teacher, Ms. Dooley, called me out in front of the entire classroom for filling my workbook with songs and poetry. I felt oddly satisfied by the sudden realization that I had a readership of one. 

In 1990 I got into the Edmonds School District's "gifted" program... after cheating on the test. On orientation day, I managed to run a staple through my finger. I was not even attempting to staple any paper. 

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