The super{set} CEO (The {Closed} Session Ep. 3.5)

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Eskalera CEO Dane Holmes is the latest {Closed} Session guest

Episode Summary

Why does the super{set} Studio Model bring on an outside CEO after a company has been founded? How is that CEO different from early product leadership? What are the qualities we look for in CEO talent to level our company up?

Tom and Vivek describe what the ideal CEO looks like in the early stage, why great product people aren’t necessarily going to make great CEOs, and what the division of labor looks like between the CEO and the rest of the early team. They then bring on special guest Dane E. Holmes from super{set} company Eskalera to hear about his decision to join a super{set} company and his lessons for early-stage leadership.

Episode Notes

At super{set}, the money from our venture fund exists exclusively to fund the companies emerging from our studio at inception and give the early team the time and focus to build. At inception, the last thing we want is the wrong CEO showing up, kicking up dust with too much certainty: the art in our model is finding the right CEO at the right time.

The average CEO isn’t suited for the early stage — the soul-crushing ambiguity, the need for collaboration and humility rather than go-it-alone decisiveness. At super{set}, we look for CEOs that can simultaneously scale up and scale down, that can see the big picture while also tackling the point-to-point challenges, all while being the face of company culture and talent recruitment.

This role isn’t for everyone, but what the super{set} team brings is the companionship of those that have done it before and been in the lonely shoes of the CEO. As special guest Dane E. Holmes from super{set} company Eskalera says, “Being a CEO is hard and lonely, doing it with other people who’ve done it makes it a little bit better. It’s still very lonely, it’s still very lonely, I wouldn’t go to happy, I would say, but better.”

Learn more about how we at super{set} found and build data-driven companies at

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