‘Investing is about optimizing discomfort’ and other gems from Notation Capital’s new podcast

A podcast about the money behind the money. That’s how Brooklyn venture capital fund Notation Capital describes its podcast, Origins.
This week they had on Chris Douvos, a general partner at Venture Investment Associates, a fund of funds based in New Jersey.
Douvos talked about his career in institutional investment (he previously co-led the private equity program at The Investment Fund For Foundations), and his outlook on investing in venture capital funds.
“One of my guiding principles: investing is about optimizing discomfort,” he explained, paraphrasing a business school professor. “If you’re doing stuff that’s too safe, that’s too conventional, you’re not taking enough risk.”
Douvos grew up in the Kensington neighborhood of Brooklyn.
“Brooklyn is kind of a blackboard that keeps getting erased and written on over and over and we’re in the midst of an awesome phase in Brooklyn’s history,” he said. “But I feel like I’m from authentic Brooklyn, back with dock workers and cops.”

One of his biggest points was the distinction between paper money and cash, which he believes are too often conflated in the venture world. Using the unfortunate phrase, “moolah in the coolah” to distinguish cash from valuations, he recalled investing in First Round Capital’s 2007 friends and family fund.
“First Round Capital still hasn’t proven it,” he said of the Josh Kopelman-led, Philly-based venture firm. “Here’s a fund that people think of as a dominant fund, and I would give them my very last dollar, but we’re still waiting for the moolah to hit the coolah. … Performance is a lagging indicator not a leading indicator.”