Cowboy Venture’s Amanda Robson Is Helping Women Founders Secure Funding

The Ontario-born powerhouse wants to empower the next generation of leaders
Amanda "Robby" Robson of Cowboy Ventures

Amanda Robson, originally from Ancaster, Ont., is a powerhouse in Silicon Valley. In November 2020, she led a US$3.2-million investment round in a securities-software company called Drata, now worth US$1 billion. When she’s not crushing it as a newly minted (and the youngest ever) partner at Cowboy Ventures, a VC fund supporting a diverse array of seed-stage founders, she’s running her organization, Modern Angels, which seeks to democratize funding for women and non-binary people.

Age: 30
Based in: San Francisco
Degree: H.B.A. (Ivey Business School at University of Western Ontario)

My goal in life:

To empower a new set of generational founders. Today, founders of top technology companies are predominantly men and not diverse. That doesn’t align with what the pool of high-potential founders looks like. I want to change that.

I thought I’d grow up to be:

A makeup artist. I always thought I would be in an industry that helps people feel good about themselves.

My biggest mentor:

Different stages of life require different mentors. In university, I had a mentor named Yang He who was working as an investment banker in New York City. He coached me and really believed in my abilities. Now, my biggest mentor is probably my boss, Aileen Lee.

The hardest decision I’ve ever made:

Turning down an offer for a full-time job at Citibank in Toronto when I had no other job prospects after graduating from university. It would have been the safe choice, but I knew I wanted to work in tech in San Francisco and I felt like I could figure it out.

My first major break:

Cold-calling my way into my first job in the U.S. at William Blair, a tech-focused investment bank in San Francisco. They sponsored my visa and really made me feel like it was possible for me to create my own career path.

My biggest growing pain:

Moving to San Francisco at age 22 without knowing anyone and working 80 to 100 hours a week. I learned how to build a life on my own, which was an empowering experience.

My most memorable mistake:

When I worked in investment banking, I was responsible for an operating model for a company we were helping to sell. Every time I made changes to the model, I had to circulate the changes to the team. One night after not sleeping for more than 24 hours, I was so zonked that I made some incorrect calculations, which my co-workers saw. It was embarrassing, but it made me realize that you can’t push yourself endlessly. You have to actually rest and take care of yourself.

I never confuse:

Niceties with kindness. It’s all about what people do, not what they say.

A great leader:

Is vulnerable and not afraid to make mistakes. Showing some of the emotions and pain that go along with struggling to make progress can be inspirational for a team.

My version of a power suit is:

A cowboy hat. To me, it represents being ready to do the work while not taking yourself too seriously. I’d like to be remembered for: Empowering the overlooked and the under-represented to fulfill their ambitions.

The word I most overuse:

“Awesome.”

My current obsession:

Learning how to be a good team builder and how to onboard people in an industry that’s not great at either of those things. Venture capital has historically been an individual sport where investors only focus on their own investments. I want to help build a firm that is truly collaborative at its core.

This article appears in print in the fall 2022 issue of Canadian Business magazine. Buy the issue for $7.99 or better yet, subscribe to the quarterly print magazine for just $20.