Currently: Early stage investor. Always learning. Sometimes writing.

Previously: Investor @ a16z | Founder @ Frank.

Always: Tortured Maple Leafs fan.

Writing: Cool, I Can | Tweeting: @dcoolican

Select Writing:

How to do a Reference Call

I've done >1000 reference calls. They can be the most valuable data for hiring & investing. But the reality is most "references" are a waste of time. Four principles for making them helpful. (June 2022)

The ___ Economy

Ever notice how there is always a new “The ____ Economy” trending? While the instinct might be to roll your eyes at the lack of creativity, there is a lesson for founders and investors in its incredible longevity. (Dec 2019)

Product Zeitgeist Fit (Video)

If you want to build or spot the next big thing really early, don’t look for what’s working — look for what isn’t but people still really care about. (Dec 2019)

T-shirt Theory

Hypothesis: early test for founders on whether you’re building something interesting is if people are trying to affiliate with your project. Call it the t-shirt theory (July 2018)

“I’ve seen this before, it didn’t work”

If you’re a founder you’ve probably heard someone say “oh, I’ve seen this idea before - it didn’t work” or “isn’t this just like that other thing that person/company X tried?” (July 2018)

As More Workers Go Solo, the Software Stack Is the New Firm

The next generation of great companies will provide integrated, vertical software for individuals going solo. (Sept 2021)

Platform vs. Verticals and the Next Great Unbundling

Looking at verticals within the broad horizontal platforms that are near their breaking point is like a cheat code: if you’re paying attention, it will point you to the next great unbundling and where the next wave of opportunity and innovation will come from. (Feb 2019)