“Best investment I made was working with Dave.”
Mike Kim
Mycroft
David Cautin
General Partner
David Cautin brings 25+ years of operator experience to founders — from the early days of consumer internet at AOL, to two venture-backed exits, to back-to-back PE CEO seats. His lens is built from time on the operator's side of the table, where the decisions are real and the consequences are immediate.
What David’s founders have to say
“
How does an underdog
become a category-defining CEO?
-
Two-time PE CEO
Led two PE-backed companies past 9-figure revenue, exiting one successfully in 2019.
-
Capital strategist
Raised close to $1B in debt and equity across multiple ventures over 25+ years.
-
Operator's lens
Helps founders see the unconventional paths to scale — and the version of themselves who can walk them.
Dave joined Enjoy The Work because the work that shaped him most was the work of building executive teams. That same operator-first instinct is what he brings to every founder he supports — practical, direct, and grounded in having done the reps.
David’s Appearances
The Struggle is where greatness comes from.
Ben Horowitz, Co-founder Andreessen Horowitz
Dave's career has spanned early-stage and late-stage, public and private, founder and operator. The throughline: finding leverage in the moments that don't look like leverage.
His leadership style is built on directness and reps. He doesn't theorize about scaling — he's done it, on the operator's side of the table, more than once, and at every stage of the company lifecycle.
Talks +
podcasts
The best founders David works with all share one trait: they want feedback that sharpens them, not feedback that flatters them. Underdogs find a way. He's spent a career proving it — and now he spends it helping founders do the same.