Why I Became a Cowboy

Amanda Robson
Nov 10, 2019 · 3 min read

People move to new jobs for all kinds of reasons. More responsibility, more upward mobility, more money. For me, moving to Cowboy Ventures was a decision that came from wanting to build something much bigger than myself. It represented the opportunity to join a small group of investors focused solely on seed, who are creating the most transparent, highest integrity, and most inclusive support system for entrepreneurs trying to defy the odds and build something great.

When I was first approached about Cowboy, I was told one of the most important things they were looking for was someone who cared more about the team’s success than their own. That piqued my interest. Many firms talk about qualities like investment judgement, hustle, and sector specialization but this was the first time putting the team above yourself was an active part of the conversation.

Three weeks on the job and I’ve already picked up on how this “we” mentality affects interactions with entrepreneurs. In meetings with founders, Aileen, Ted, and Jomayra will say things like “our company” and “how are we going to think through this”. There is a real sense of communal ownership over everything from making investment decisions to helping portfolio companies to managing the office. This feels rare in the world of venture capital that can obsess over the accomplishments of individual investors by focusing on things like Midas list ranking and the performance of a single partner’s portfolio.

Looking back on the last few years, the professional accomplishments I’m most proud of are the ones that required a strong team. One example that comes to mind is an investment that we made at my previous firm, Norwest, in a robotics company called 6 River Systems, which was recently acquired by Shopify. The founding team had experience across robotics, warehouse management, and software engineering while the board had backgrounds in manufacturing, robotics, and venture. There were multiple things that made the company successful (most notably the hard work from the founders and employees) but the combination of unique perspectives across the team is what gave the company a competitive edge.

I am grateful for my experience at Norwest and the incredible opportunity to learn from the talented investors there. It is a strong and established multi-stage firm and provides investors that are early in their careers the platform and mentorship to be successful. But for me, the opportunity to be a part of building a seed fund like Cowboy was too unique to pass up.

I’m incredibly excited and grateful to be part of a firm trying to set the standard for what it means to be a “team-first” VC. We hope to help champion this mentality across the industry and create the best environment for entrepreneurs who are navigating the earliest stages of building a company.

A little about what we invest in: we’re excited to work with seed-stage founders that have a unique insight into a problem or industry across enterprise and consumer. Particular themes our team is passionate about include unsexy tech, data privacy, mobile health, and learning loop software. I’ll be spending time along with members of our team in applied AI, data, and infrastructure software. If you’re a founder building in those areas and want to join our family, we’d love to meet you.

Also posted on: http://cowboy.vc/blog/