In the latest episode of Caveat Founder, we hosted Sean Byrnes and Edith Harbaugh. Edith and Sean discuss the importance of directly asking for money when fundraising and ponder why most founders, including serial founders, often underestimate the difficulty of getting early customers. They also consider how companies that struggle and survive often develop a higher level of operational excellence than those that gain success quickly.

In this episode, Russ Smith, CTO at RainforestQA, talks with Guy Podjarny, CEO at Snyk.io. Guy and Russ discuss the realities of distributed teams, how they approach hiring for startups, and finally they dig into the many different roles that fall under the title of CTO.

In this episode we host Sean Byrnes, CEO of Outlier.ai, previously CEO of Flurry, and Edith Harbaugh, CEO of LaunchDarkly.

Edith and Sean discuss how things have changed since Sean founded Flurry in 2005, they talk about how building a startup is just like running a marathon, and finally they share stories of just how easy it is to make the same mistakes twice.

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I’m happy to share the first episode of Caveat Founder, Heavybit’s newest podcast. Caveat Founder is a regular series featuring founders sharing their experiences building developer facing companies. Gain insight into what it takes to build a successful developer facing company by hearing success (and failure) stories directly from founders themselves.

In this inaugural episode, Ilya Sukhar and Fred Stevens-Smith talk through pricing challenges at developer facing companies, the type of investors developer facing companies should look for, and the sometimes difficult transition from Founder to CEO.