Cowboy Ventures
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Cowboy Ventures

Becoming a Cowboy Partner!

Today, I’m excited to share my promotion to Partner at Team Cowboy as we get ready to start investing our 4th fund, and our new Mustang fund for follow-on investments 🤠

When I started in venture capital 6 years ago, it wasn’t the most welcoming place for someone like me. This was 2016, before organizations like All Raise existed, and there weren’t many female partners at venture funds. I was also investing in technical enterprise companies, where fewer female investors spent time. I loved the job, but it wasn’t clear what my long-term place would be in the venture ecosystem.

Fast forward to the summer of 2019: I get introduced to the Cowboy team and immediately fall in love. Cowboy was a seed fund I had long admired for its track record, reputation with founders, and incredible culture. It was founded by Aileen Lee, one of the most prominent female investors in the world, who is widely known for her contributions to the venture ecosystem as the co-founder of All Raise and coiner of the term “unicorn”, in addition to being a world-class investor. Venture capital has long had an apprenticeship model and, for me, Aileen was the best person I could learn from.

Investing in seed-stage companies is different from other kinds of venture investing. We typically invest pre-revenue and pre-product so have less information to predict how a company will perform. There’s nuance involved in identifying the best teams and opportunities at this stage. Focusing solely on seed, with a team of Cowboy’s caliber, has pushed my ability to identify and support the best early-stage teams. On top of that, Cowboy is a place I’ve been able to be my authentic self in a way I didn’t think was possible in this job.

In addition to Aileen, I’ve learned an immeasurable amount from sitting on boards and investing alongside Ted Wang, as well as watching our team grow with the additions of Jill Williams, who leads FinTech investing for Cowboy in New York, and Allegra Simon, who supports our team as a phenomenal Chief of Staff.

I joined Cowboy as our first sector-focused investor after 4 years of early-stage B2B investing at Norwest Venture Partners. At Norwest, I worked with incredible B2B companies including 6 River Systems (through their acquisition by Shopify), Dremio, Fossa, and Productiv.ai.

At Cowboy, I have continued investing in B2B companies with an eye toward developer tools, data platforms, applied AI, and security. I’ve been fortunate to partner with incredible companies including Drata (Cowboy’s fastest seed-to-unicorn company ever 🦄), mobile.dev, Byteboard, LaunchNotes, SVT Robotics, Mutiny, and Arcol among others.

Within developer and data tools, open source has been a major focus for new investments. Because of that, I started the Open Source Startup Podcast with a good friend (and frequent co-investor) Tim Chen of Essence VC. The podcast has grown to ~10K listeners across 30+ episodes with learnings from top open source companies such as Chronosphere, Airbyte, Vercel, DBT, Kong, and MongoDB.

For Cowboy’s 4th fund, we’ll continue backing technical B2B founders. Key themes we’re excited about are the democratization of software development, cloud data usability, automation of back-end infrastructure, and the ‘shift left’ of many functions including testing and security.

Since many of our investments focus on developers, we shared our framework for investing in developer tool startups here which will continue to guide our investment thinking.

We would love to partner with more technical female founders. At Cowboy, we see potential in founders from all kinds of backgrounds and our investments are a reflection of that. In Cowboy’s most recent fund, 48% of investments have been in female founders and 35% have been in underrepresented minority founders*.

While the venture ecosystem has become a more inclusive place over the past few years, there is a lot of work remaining to level the playing field for investors and founders from underrepresented backgrounds. In addition to our work at Cowboy, our team will continue building the Female & Non-Binary Operator Angel Network that today includes 160+ operator angels.

Our team is also involved in a number of organizations that help further the venture industry and, for my part, I will continue working on the All Raise VC Champions Program which matches principal-level investors with general partners for mentorship opportunities, as well as serving on the board of NextGen Partners to help up-and-coming VCs learn how to become world-class investors.

My years at Cowboy have been the most enjoyable of my career. I’m excited to continue serving our current and future founders, the Cowboy team, and our broader community for many years to come 🤠

A special thank you to Aileen for taking a chance on me, Ted for being a “wise owl” through many situations, Jill for being an incredible partner and sounding board, Allegra for being the ultimate teammate, and Mae for being a superstar EA for our entire team. Cowboy is a special place because of them.

If you’re a founder building in the spaces I cover — I would love to hear from you. Shoot me a note at amanda@cowboy.vc!

Read more from the Cowboy team on the promotion 👉 here

*Based on number of investments in Fund III

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