Why I became a Cowboy 🤠

While chatting with Cowboy about the opportunity to join their team, Aileen and Ted asked me a number of questions that stood out to me, such as, “how can we help you grow as an investor?” and “where do you think you can use the most mentorship and support as you grow?” For most VC funds, questions like these that are focused on the growth of your colleagues (let alone a prospective colleague) are unheard of. Yet as I spoke to portfolio companies and founders who have worked with the team, it became clear that this thoughtfulness wasn’t just a one-off occurrence, but rather an attribute of the team that motivates how Cowboy operates and core to their DNA.

As my colleague Amanda Robson wrote when she joined, one small detail that exemplifies this characteristic and stood out to me immediately is how the team interacts with potential portfolio companies. Subtle nuances such as changing “how do you” to “how do we” can make a huge impact and are second nature to the team. From day zero, we aim to send the message that we will be part of your team and that we will all work to support the vision as owners.

We are investing at a time in the market cycle where companies are staying private longer and have more options in terms of capital than ever before. How a venture capital team supports its portfolio companies, not just as founders, but as humans has become increasingly important. On our portfolio company page, Cowboy highlights the founder, not the company logo, as we believe this is a human-centric business. Being a stage-focused fund, we have the expertise to support companies from the ground floor (or even just blueprints) to a live product and beyond. We understand the challenges and pitfalls these founders face and use our insight to provide guidance that can be invaluable for entrepreneurs. With over 45 early stage investments, Cowboy has developed that playbook and we lean in to provide their expertise to the success of our founders as we know what it takes to support a company through their Series A and beyond.

The last five years at Anthemis were invaluable, and I am immensely grateful for all that I learned from my colleagues and all of the relationships that I made. I learned how to become a great early stage fintech investor, investing in companies such as Harry, Josh, Zain, and Michal at Pipe, Kaeya at SwayPay, David and Aaron at EasyHealth, and Chris, Rob, and Max at Rally Rd (amongst many other of my incredible founders /portfolio companies), and how critical those early months are to a company. As I feel increasingly more excited about the earliest stages, I see Cowboy as an incredible opportunity to take my sector knowledge and combine it with the platform and stage expertise of the Cowboy team.

When contemplating the prospect of joining Cowboy, a lot of the reasoning behind my decision came down to the team. Deciding where I wanted to spend the foreseeable future of my venture career and at a time when in-person meetings were sparse was not an easy decision. However, with such a small and tight-knit team, the opportunity to get to know my new colleagues (Aileen, Ted, Amanda, and Mae) virtually simply felt right. We work in an industry where everyone says that team is everything and this decision was certainly no exception for me. My colleagues’ different backgrounds and expertise helped display the team’s one motivation that really stood out: to build the best Seed Fund in a human-centric way.

So, while I’m only at week 3, I am extremely excited about being a Cowboy. I will continue to have a special focus on fintech, while also broadening my horizons (although everything is fintech these days, right?). If you’re building anything in the fintech space, I’d love to hear from you! I am excited about fintech infrastructure, the creator economy, fintech for Gen-Zs, or verticalized fintech space. If you work in those areas, please feel free to reach out at Jillian@cowboy.vc. At Cowboy, we are a generalist pre-seed, and seed-stage fund focused on consumer and enterprise startups, and we would love to hear from you.