By: Jillian & Robby At Cowboy, we believe in the power of learning from the past. Since 2012, we’ve invested in 100+ companies, starting at the earliest stages, and have helped founders lead through good and challenging times. And we’re always looking to sharpen our advice to our portfolio companies…

By Jillian Williams The fintech sector has gone from one of the hottest sectors to struggling in the public markets, leading to uneasiness in the broader fintech startup market. While markets may be rocky, we still see a lot of room for innovation in the fintech landscape across B2B and…

Thrilled to share our awesome Cow-lleague Amanda aka “Robby” Robson has been promoted to be a Partner at Cowboy Ventures By: Aileen (on behalf of Team Cowboy) Thrilled to share our awesome Cow-lleague Amanda aka “Robby” Robson has been promoted to be a Partner at Cowboy Ventures. If you haven’t…

By: Robby Breaches, downtime, and more in our Q1 2022 Software Infra Review At the end of every quarter at Cowboy, we do an internal review of the most important things that happened in the areas we focus on, and their implications for our founders and future investments. …

By: Aileen In his recent post, my longtime friend and Cowboy pardner Ted Wang shared that he’s blazing a new trail as a business coach. I’m thrilled for the founders who will work with him in this new capacity — he is exceptional. …

By: Aileen & Robby Hiring technical talent in today’s environment can most accurately be described as “brutal.” It’s expensive, time-consuming, and extremely competitive. To add insult to injury, many companies are still using age-old technical hiring practices, which include spending engineers’ precious time quizzing candidates about arcane computer science problems…

One investor’s framework for evaluating early-stage developer tool startups By: Robby Over the past 5 years, I’ve talked to and evaluated hundreds (if not thousands) of developer tool startups. Given the number of paid and free tools available, the bar for investing in a team that’s building something new is…

Announcing Drata’s $100M Series B, fuel for putting security & compliance on autopilot By: Ted & Robby It’s October 8, 2020, the day our team first (virtually) sat down with Drata CEO Adam Markowitz to discuss potentially partnering for their seed round. That meeting can be summarized by the following…

By: Jillian Williams The growing embedded finance space has laid the foundation for the next generation of consumer fintech-enabled companies. With the idea that “every company will be a fintech company”, founders are building incredible fintech infrastructure companies, the “picks and shovels” that will create the financial service industry’s future…