Riley O'Brien


T  +  1 617 526 6097

My favorite part about working with is helping people build something that they're passionate about.

Experience: I represent emerging companies in a variety of corporate matters—solving problems and being able to contribute to people's successes. I love being the lawyer people want to call. And selfishly I also like to see all these products and check in when they're still in stealth mode before the company goes to the public—it tickles my “nerdy tip of the spear” inclinations.

Off the clock: Our new baby girl is keeping me pretty busy, but when I’m not playing with her, I like to cook for family and friends. One passion for my wife and I is sourdough bread—we have a starter named “Frodough” that has lived with us in three different countries and it’s probably around six-years-old. We do a lot of live fire cooking, like woodfired pizzas. I found out a long time ago I was bad at sports, but good at training for them, so we do a lot of weight training and have a pretty active meditation practice on the side. 

Reading recommendations: When it comes to work in , I usually recommend Venture Deals by Brad Feld or anything else by him. I am also a lifelong fantasy and sci fi nerd, and as a Canadian, I end up recommending Canadian authors a lot—I like anything by Guy Gavriel Kay, in particular The Fionavar Tapestry. Another one in the sci-fi world is Blindsight by Peter Watts—especially if you like hard sci fi or musings on the nature of consciousness and what an alien civilization would be like if we ever actually ran across one. 

What I’m listening to: Sam Harris's podcast Making Sense, which spans the vast broadness of every kind of topic from meditation, consciousness, morality, etc.

Choosing a home: My wife and I took a “goldilocks” approach to determining where we wanted to live. We started off in Western Canada, in my hometown of Calgary, Alberta. The first winter my wife spent there, we hit the point where Celsius and Fahrenheit crossed: negative 40—which was too cold for her. So we moved to Bermuda from 2020-2022—that was too hot for me. So moved back to Massachusetts. People always laugh at me when I tell them that the Massachusetts weather is just right. 

Recent Matters

  • WilmerHale Advises Investors in Nasdaq Private Market Series B Financing
  • WilmerHale Represents Alethea in Series A Financing Round


JD, University of British Columbia, 2015

BCom, Business Economics and Law, University of Alberta, Alberta School of Business, 2012

Bar Admissions

Massachusetts, Alberta, Canada (Inactive), Bermuda (Inactive)


Corporate, Emerging Company and Venture Capital, Mergers and Acquisitions, Capital Markets


Life Sciences: Biotech, Pharmaceutical
Technology: Energy, Clean Tech, Fin Tech, Materials Sciences (includes nanotechnology, semiconductors, etc.), Mobile, Telecom, Infrastructure, Software (includes SAAS and Cloud computing)