Barry Diller’s System, Part I: Diller’s Roots.

"You won’t be able to imagine the level of energy and commitment and the things you have to give up if you really want to do something like this."

This is the first piece of a two-part deep dive on Barry Diller. Part II.

Why Diller? Yesterday, I heard a quote by Dan Zwirn: “the best value investors are as comfortable with securities as they are with operating companies.” I agree. Great businesspeople often straddle the worlds of investing and operating. They are capital allocators, leaders, and creators. Guided by a set of principles they defy the labels of the investor, the entrepreneur, the Chief Executive, the operator. They are multi-faceted and multi-dimensional: they express themselves and their craft in public and private markets, through control and minority stakes, by building, acquiring, and selling assets.

I found Barry Diller to be a great example of someone who married the operating and investing worlds. After rising to the top of Hollywood, he left to take a road trip to the future and built IAC, the “anti-conglomerate,” which acquires, incubates, operates, and spins off technology companies. He has been highly succe…