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…

The way people will work in the future has evolved beyond existing HR software By: Aileen Lee For years at Cowboy Ventures, we’ve been investing in what we call “life 2.0” companies — early-stage software startups that make our work and personal lives more efficient, accessible, and /or delightful. …

Making future marketing more effective By: Aileen Lee In the summer of 2018, John Waldmann, CEO & Co-Founder of Homebase, sent me an email, “Interested in an intro to Jaleh? She was the Head of Marketing at Gusto. Very sharp.” I am grateful for the intro and very glad Jaleh…

Announcing Cowboy Ventures’ investment in Mobile.dev By: Amanda Robson Today, we’re excited to announce our partnership with mobile.dev as they set the new standard for mobile application development. Mobile development has not received the attention it deserves, despite what a huge industry mobile has become. …