17. Steven Comfort – HotWired into the first online ads

Steven Comfort started life — as so many ad tech pioneers did — as a media planner and buyer in NYC for agencies such as DMB&B and Messner Vetere. Inspired by his grandfather, who founded his own successful agency via the G.I. Bill after World War II, Comfort abandoned dreams of playing professional baseball and embraced traditional media, little knowing that a confluence of time and place was about to insert him into the epicenter of the first ads on an entirely new medium, the internet.

As Comfort tells Marty & Jill in this reflective episode, he was tasked by Vetere management to compile a “cheat sheet” to new media testing opportunities (primarily in nascent cable systems such as Time Warner in Orlando). During his researches, he heard about Wired magazine’s plans to launch a website and cold-called them for more info. Shortly thereafter, he had a “mind-blowing experience” (his words) as Wired co-founder Jane Metcalfe showed him QuickTime and the imagery-plus-sound-plus interactivity possible on the new browser-based media.

(For a compelling oral history of the birth of Wired check this out.)

Wired issue from Oct 1994 announcing HotWired

Settling the rumors, Comfort admits the first online ad was sold “by Jane.” And it wasn’t – as widely believed – just an ATT ad but rather a “twelve-way tie” among the first advertisers on HotWired.com, Wired’s new online venture, all of whom went live simultaneously.

Comfort then joined Wired and moved to San Francisco, a move he doesn’t seem to regret, and rode the dot-com boom to its peak and down again. What was that like? “It felt like college,” he recalls, but he believed in Wired’s mission – and also their office building neighbor Organic’s – and it’s persisted.

After Wired, Comfort joined a startup that was acquired by Yahoo, and then a number of high-flying (and less high-flying) media and content companies such as Monster, NexTag, YuMe and Radius. Currently, he provides go-to-market consulting services for tech companies and is based in the Bay Area.

(For more on the layout and approach of the original HotWired site, check out this cool site.)

16. David Carlick – untold story of Poppe Tyson and DoubleClick

David Carlick was a key player in the early years of DoubleClick and lead the Silicon Valley office of the legendary B2B agency Poppe Tyson, which did so much to bring ads to the nascent internet via clients such as Netscape and Silicon Graphics. (Poppe Tyson, a division of Bozell Worldwide, later merged with Modem Media and its name was retired; Modem merged with Digitas and both joined the Publicis Groupe.)

Starting life as a dropout in the Vietnam Era, Carlick kicked off his entrepreneurial life in the waterbed business in a thriving California market. After earning a CPA and working for a bit as an accountant in the Valley, he succumbed to the lure of advertising and started his own business, working with clients such as Intel and Osborne, the first successful PC, honing his high-tech storytelling and sales skills.

Carlick’s work for a once-rocking, now kaput, PC company.

As Carlick tells Marty and Jill in this groovy episode, Poppe Tyson was run by a legendary New York-based raconteur and ad man named Fergus O’Daly – a habitue of steak houses, firecracker for liberal causes, and beloved personality of the old style. O’Daly was the man who came up with the name “DoubleClick” as a label for the gestating digital efforts of his team in New Jersey, then focused on CD-ROMs.

Fergus O’Daly (left) and David Carlick discussing ad strategy

At some point in 1994, Carlick visited Kevin O’Connor in Alpharetta Georgia in the labyrinthian basement office he used to found his company, then called Internet Advertising Network/Systems. Both Poppe Tyson and O’Connor’s company were building an ad server to support a network of pubs; both agree O’Connor’s (built with Dwight Merriman) was “further along.” They joined forces and the mighty DoubleClick, as it was called, was born as part of the Bozell family.

As recounted in our recent #PaleoAdTech episode with Kevin O’Connor, DoubleClick spun out from the agency and went public. Shortly after the IPO, Carlick ran askew of the company’s management due to what he describes as a complicated miscommunication, and he left and began to focus on investment, board and advisory roles.

Those roles took him on many adventures in adland – some of which he shares with us. He takes us behind the scenes at AskJeeves, a highly-valued natural-language search engine represented by Mike Ovitz, and MySpace, which Carlick describes as something of a “cobbled-together product” that ultimately lost to Facebook due to its inability to scale.

These days, Carlick is an independent director working with companies in fintech, sponsorship and digital media among others.

15. Dave Moore – the epic of 24/7

David Moore is the CEO of Britepool, an advertising identity management and resolution company developing an alternative ID for publishers. An affable Midwestern dealmaker, he moved east to join a TV ad sales rep company and then CNN at the dawn of the cable TV revolution. He recalls going on sales calls with an exuberant Ted Turner, who sometimes helped and “sometimes … hurt.”

Dave worked at Petry Media and Lifetime Television before founding 24/7 Media somewhere between 1995 and 1998 (it was a complicated process). The company was an ad network that aggregated about 1,200 publishers at peak and sold to advertisers seeking national scale. As Dave tells Jill and Marty in this nail-biter of an interview, “What I didn’t appreciate at the time was that … ninety per cent of our revenues were coming from dot-com companies.”

That meant of course that when Alan Greenspan proved prophetic and “irrational exuberance” did indeed lead to “prolonged contraction” (as Greenspan predicted), 24/7 was almost wiped out overnight — going from a market cap of $1.8 billion and a stock price of $68 to a market cap of $15 million and a price of $0.15.

How did Moore keep his company afloat?

“It was tough,” he admits. “My favorite quote was from Winston Churchill, ‘Never give up.’ A short quote.” Facing an executive coterie begging to declare bankruptcy and auditors dubious of its solvency, Moore’s 24/7 cut its staff 40%, closed global offices and — in a twisty episode also described in our Dave Morgan episode — acquired Real Media for 19.9% of the company’s stock (the maximum allowed without board approval), after DoubleClick lost a bid by offending the investors.

What followed was a spectacular turn-around, year by year, as the stock rose and Moore managed the company, now named 24/7 Real Media, back to profitability and a $200 million run rate … and ultimately a $650 million acquisition by Martin Sorrell’s WPP holding company.

That turnaround is one of the “underappreciated” feats of the dot-com postscript, Morgan told us.

Moore stayed on at WPP for 12 years as Chairman and later President of WPP Digital until leaving in 2019 to found Britepool.

In this look back on a highly eventful career, Dave displays the humor and candor that have won him the enduring affection of former employees and colleagues. He’s a testament to the power of endurance and the value of that overlooked American salesman’s trait: true optimism.

14. Lou Montulli – building browsers, cookies and more

We’re honored to be joined by the legendary Lou Montulli this week. Some of you hard-bitten ad tech types may not be as familiar with Lou’s legacy as you are with some others’ – but we’d argue he’s more important than most.


He was there at the beginning, working on standards and browsers that established much of the working procedure we take for granted — and some of which we’re trying to change — today. Lou was there in the early 1990s in the minute community that cared about the proto-web, engaging with now legendary characters such as Tim Berners-Lee at CERN, Marc Andreessen at the National Center for Supercomputer Applications (NCSA) and Jim Clark of SGI and Netscape.

While still a University of Kansas Comp. Sci. major working part-time on the computer center’s help desk, Lou combined two open source projects (Gopher for networking and HyperRez for hypertext) into the Lynx browser. Through that project, he got involved with the early web engineers and the NCSA team building the Mosaic browser.

After a disappointing finish at a national racquetball tournament, Lou returned home to find a message on his answering machine from Jim Clark, inviting him to Illinois for what turned out to be the birth of Netscape. “He was very persuasive,” Lou tells Marty in this candid and captivating interview. “Especially in those days.”

Moving to Mountain View to build Netscape, Lou recalls non-stop work at a pace that came to be known as “Netscape time,” 12 Mountain Dews a day, disagreements over code that almost got physical, parties in the shadow of a giant Wonder Woman doll, and a futon room with no windows … a glorious time when a handful of kids really believed they were changing the world for good with their browser.

In that initial development phase before launch, Lou and his team came up with many features we still use today: HTTPS, server push and client pull, various tags, the famous fish-cam (a live web-cam pointed at Lou’s fish tank), animated GIFs … and the browser cookie.

(Lou also described the development of the cookie in another interview Marty did with him a few years ago.)

As he recalls, the cookie was an afterthought at Netscape, a way to maintain state for single domains so that things like shopping carts would remember items from page-to-page and sites could remember you next time you appeared. Ad tech as we know it was not part of the picture — and indeed, Lou is clear (and right) in his assertion that none of it would work unless cookies were combined with JavaScript, headers and a cooperative network (aka a “conspiracy”) of partner websites.

You can read more about the team’s original thinking behind making third-party cookies active by default in Lou’s own words. In sum: they’re a more transparent and user-controllable option than fingerprinting.

AOL acquired Netscape in 1998 at a time when Microsoft was well into a system-wide effort to dominate the browser market, perceiving a threat to its application development business. As Lou says, that threat was real and Microsoft won; he took a leave of absence from the company that same year and never went back.

“It was a blessing,” says the optimistic engineer. Without that prod, he might not have gone on to found other companies such as Memory Matrix (acquired by Shutterfly, where he was CTO for a bit); and Zetta, which does storage and disaster recovery for SMBs. He’s currently co-founder of JetInsight, a management system for chartered airline fleets.

13. Dave Morgan – keeping it Real(Media), TACODA and Simulmedia

Dave Morgan is the CEO and founder of Simulmedia, which provides a scaled ad targeting platform for TV and video games. He’s from the great state of Pennsylvania and is the first former lawyer we’ve had on the show. In the mid-1990s, he founded Real Media — one of the first ad-serving and -networking companies. It merged with the legendary 24/7 agency in 2001 to form 24/7 Real Media (later acquired by WPP and morphed into Xaxis).

Dave also founded TACODA, an early behavioral-targeting platform for digital ads acquired by AOL in 2007. Simulmedia was founded in 2009.

In his charming style, Dave chats with Jill and Marty about his early days in a semi-rural town that had more deer than people; his short career as a big-city Philadelphia lawyer; and his gig as General Counsel at the Pennsylvania Newspaper Association in the early 1990’s, a move that exposed him to media and the theme of his career: aggregating local media to support scaled national ad buys. (That’s kind of what Simulmedia does for TV, now that we think about it.)

He tells the story of a legendary elevator pitch to Brad Burnham, later of Union Square Ventures, and how that pitch got him to New York City. Real Media’s first real offices were in a rug merchant’s building two blocks from his current space at 28th Street and Park Avenue South.

Real Media was an ad server that competed with NetGravity (acquired by the mighty DoubleClick), and it was an intrepid survivor of the crash of 2001, picked up by 24/7 (after a rejected bid by DoubleClick) for a reported $2 million. TACODA started as a behavioral targeting platform but took off after becoming a tech-powered ad network.

In a delightful aside, Dave talks about his brief and wonderous tenure at AOL, where he re-read Machiavelli’s The Prince on a tip to understand his internal political situation, recommended strongly against acquiring the Bebo social network, and left when his advice was ignored. He was vindicated when the network, which cost AOL $850 million, was sold a few years later for around $20 million.

And he reveals the little-known fact that Elon Musk actually started in ad tech, founding a classified ad-serving company called Zip2 with his brother Kimbal, long before he launched himself into space. A future guest? We’ll see.