Amanda “Robby” Robson is a Partner at Cowboy Ventures and the co-host of the Open Source Startup Podcast. In this episode, Robby shares insights on what she’s looking for in open-source founders to potentially invest in, including the importance of being able to manage both your community and your paid model simultaneously. Robby and I also discuss the importance and pitfalls of choosing a monetization strategy, as well as the dangers of having too many monetization models too soon. Throughout our conversation, Robby highlights the specific challenges that open-source founders face, and how she’s seen successful founders either avoid or overcome them.

Highlights:

• I introduce Robby, who is a Partner at Cowboy Ventures and the co-host of the Open Source Startup Podcast (00:22)
• Robby gives some insight into how she evaluates startups from an investment perspective, and the peculiarities that go into evaluating an open-source startup (00:45)
• The nuances of evaluating the market opportunity for an open-source company (05:20)
• A common mistake Robby seeks early stage founders make when evaluating their market size (08:06)
• Robby shares what she’s learned about best practices for seed-stage startups who are looking to determine their monetization strategy (10:02)
• The dangers of having too many monetization models as an early stage startup (13:22)
• Traits that Robby feels are most valuable for an open-source founder to possess (14:48)
• Robby reveals the common traps that open-source founders fall into (17:13)
• Why Robby feels that successfully monetizing an open-source company has more to do with resources than timing (19:46)
• Robby’s thoughts on whether she would ever found an open-source company and how she would approach it (21:18)
• How Robby’s thoughts have changed on whether open source projects need to intentionally become a company or vice versa (23:44)
• What it’s like to advice against the open-source business model as a venture capitalist (29:10)

Links:

Robby

• LinkedIn: https://www.linkedin.com/in/amanda-robson-7227685b/
• Twitter: https://twitter.com/amanda_robs
• Company: https://www.cowboy.vc/