18. Kevin Ryan – up and down and up with DoubleClick

Kevin Ryan was part of the trio that led DoubleClick from its inception in the mid-1990s through its traumatic post-crash chapter and back toward health and the sale to private equity in 2005 — the critical years where it established its product and market dominance and was ready to be spruced up (by others) for its ultimate exit into Google and ad tech legend. Ryan was CFO for a few months and then President, taking over leadership from co-founder Kevin O’Connor [check out our amazing episode #12 with Kevin O] during the tense moments of the early ’00s, when the industry faced an existential crisis.

He left in 2005 and went on to found and co-found a litany of companies including MongoDB with DoubleClick co-founder Dwight Merriman, Business Insider with Henry Blodget and Gilt, among others.

Officially, he is the CEO and founder of AlleyCorp, which is an investment firm based in Ryan’s long-time home town of NYC.

As Ryan tells Marty in this fast-paced reflection [Jill is out this week], after leaving investment banking he was exposed to the nascent internet and the promise of digital marketing and commerce when he worked managing operations at EW Scripps, which gave us Dilbert. Exploring ways to scale ad-selling on the popular Dilbert website, Ryan met with “the five companies” who did web ad sales at the time, including DoubleClick, where he became employee #12ish.

As CFO and then President, Ryan complemented the other Kevin (O’Connor) by focusing on running the business, managing global expansion and rapid growth, while O’Connor and Merriman excelled in product innovation and strategic nuance. One of the first NYC-based startups in the sector, DoubleClick grew to 2,000 employees and a market cap approaching $15 billion within 4-5 years after launch.

It was known for its incredible parties — one of which Ryan tells us cost $200,000 — and indelible branding, as “DoubleClick Welcomes You to Silicon Alley!” imprinted a decade of Manhattan’s jealous youth. They also had an HQ in a former ice rink with a basketball court. Here’s the lobby:

DoubleClick welcomes you to DoubleClick

Ryan shares his take on government investigations in the early ’00s, why he likes Burning Man, why early-stage VCs should probably be close to their portfolio companies, why Hellman & Friedman was “the right winner” in the DoubleClick acquisition stakes, and why he doesn’t get up in the morning thinking “advertising is so great!”

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