47. Larry Braitman – fishing for dot-com dollars with Flycast

Larry Braitman was co-founder of Flycast, a dot-com-era digital ad network known for its direct-response focus, lower entry costs for advertisers and publishers, relative ease of use and optimization, and explicit embrace of what the Wall Street Journal called remnant (or unsold) inventory.

Larry founded Flycast — named for his co-founder Richard Thompson’s precision piscine pasttime — in the summer of 1996 in San Francisco, where he’d relocated from his hometown of Philadelphia. Flycast IPO’d in 1999 and sold to the roll-up holding machine CMGI in January, 2000.

This proved to be excellent timing, of course, just months before AOL-Time Warner and the end of days, and CMGI’s all-stock deal, priced at a reported $559 million, rose at the peak of the dot-com bubble to a staggering $2.2 billion. (CMGI’s own IPO was put on hold in 2000 and it was out of the internet ad business by 2003.)

At the time, Flycast had revenues of about $25 million, up from less than $5 million in 1998, and was running at a loss. In total, it raised $20 million and had about 800 publications in its ad network, 75 employees and 300 advertisers, according to public filings.

Larry started his professional life as a corporate attorney and tax partner in Philadelphia. Seeking a second act, he met Rick Thompson through a VC who’d rejected an earlier newsletter startup he’d pitched. At the time, Thompson was a student at Wharton Business School.

As Larry tells Marty in this reflective episode, Flycast emerged from multiple brainstorming sessions as the last in a string of previously-discovered ideas. From the beginning, it stressed self-serve automation and practical tools for ad buyers and publishers, a down-market DoubleClick for the DIY domain.

Candid photos (shot on film!) of the early Flycast team hard at work in their SoMa offices in SF (mid-1990s)

Components of its solution included:

  • AdAgent — desktop tool for ad buyers to schedule up-front and “opportunistic spot buys”
  • Media Templates — automation tools for common requirements like A/B tests, day/time buys
  • AdReporter — measurement tool

In the pre-programmatic era, Flycast offered the ability to prepopulate prices within an ad server to meet reach targets. The “Blind Buy” was a lower-cost option, familiar to ad network users even today: you don’t know where your ad’s running, but it’s cheap.

Tactics such as the “Tonnage Buy” and the “Media Blitz” reveal the company’s unpretentious tone and tilt toward usability, giving buyers an option to set a high CPM and get a virtual “ton” of impressions.

Pricing was a percent of media with a limited freemium/try-before-you-buy model. Larry says Flycast started its fees at 15% of media spend, and its website ultimately broadcast a list price of 30% (presumably negotiable).

Not long after CMGI acquired Flycast, it shut it down. CMGI itself was a victim of the dot-com meltdown. In all, it had rolled up (and then down) some 50 companies, including Engage, AdSmart, AdForce, AdKnowledge and Flycast. Its last bold venture was acquiring the search-engine AltaVisa in 2002 and selling it a year later at a 94% discount.

In 2005, Larry was back at it, co-founding Adify Corporation. Adify was a white-label solution to build vertical ad networks, going to market based on an anchor-tenant and long-tail model. Ultimately, it helped power 100 networks, including Martha Stewart’s lifestyle sachet and Forbes’ business-financial mesh, and was acquired by Cox in 2008 for a reported $300 million.

These days, Larry is an early-stage investor who likes to work with companies across a range of industries, advising on practical matters such as strategy and helping to line up initial funding rounds. None of these companies is in ad tech.

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