21. Mark Zagorski – eXelate, Telaria & DoubleVerify

Mark Zagorski is a tenured ad tech CEO, having led eXelate (acquired by Nielsen), Telaria (later Magnite) and currently DoubleVerify. But more than that, he’s a true ad tech O.G., joining pioneering agency Modem Media/Poppe Tyson as an A.E. in the mid-’90s right as digital ads were getting started. (For more on Poppe Tyson, check out this episode.)

As Mark tells Marty and Jill in this career-spanning saga, he started life in NYC wanting to work for Spin magazine, going so far as to sneak into their offices to drop a resume. Spin looked elsewhere, so he joined some brands after business school as a manager. At Honeywell, his boss asked him to help build a website for this new thing called the Internet, and he enrolled in a class at the Learning Annex.

Visiting Honeywell’s agency one day, he heard that an upstairs neighbor was hiring — this was the legendary Poppe Tyson, which merged with Modem Media to bolster its media buying capabilities. At PT/MM, Mark saw the explosion of the scale and scope of the web — and got an idea.

His next chapter (which he jokingly called “The Dark Era”) was an attempt to bring digital advertising to the websites of local linear media. At WorldNow (1999-04) and later MediaSpan (2005-08), he tried to convince local media owners that their businesses were threatened by the web and to rev-share ad spots on their websites. He admits he may have been a bit early, in an era of narrow-band and early broadband.

Getting stations online
Mark Zagorski at WorldNow

After an arm-waving meeting in a Manhattan coffee shop, Mark made the leap to join an early-stage startup called eXelate in 2009 as CRO. eXelate was similar to BlueKai and TACODA as a data-oriented behavioral targeting company and later DMP. He became CEO in 2010 and helped steward eXelate through an acquisition by Nielsen in 2015. He was head of Nielsen Marketing Cloud until 2017.

That year, he became CEO of Tremor Video, which changed its name to Telaria and merged with Rubicon to become today’s Magnite. And in 2020, Mark joined DoubleVerify as its CEO to lead its CTV expansion strategy.

20. Ari Lewine – going native with TripleLift

Ari is the co-founder, along with Eric Berry and Shaun Zacharia, of TripleLift, a programmatic ad platform that helps advertisers and publishers to do native advertising. And native of course is a space that was identified in 2011 in an OMMA keynote by investor Fred Wilson, inspired by in-stream social ad formats (particularly on mobile) that blend in with the surrounding publisher context.

Ari and his co-founders met at then-white-hot-DSP AppNexus (now Xandr), where Ari was a young account exec with a specialty in handling Israeli ad networks. He left AppNexus with his co-founders (aka friends) in 2011 without a clear idea of what kind of company they were going to found, joining an accelerator in Times Square with little heat and light-deprived due to a New York Times billboard on the window units. An early idea to automate Pinterest marketing fizzled when Pinterest “didn’t return our calls and emails,” as Ari recalls.

By 2012, the team had identified the native opportunity — originally calling it ‘organic’ and ‘sponsored images’ — and set about trying to sign up publishers. Their first success was with a blogger who ran a site called FoodGawker, which led to a vertical-focused strategy starting in food. The team assembled enough publisher scale to enlist its first ad customer, Chobani, and from there expanded into fashion and other industries.

TripleLift co-founders Ari Lewine, Eric Berry and Shaun Zacharia

In contrast to many of our other episodes, TripleLift’s is a story of great timing, rising markets and ultimately happy outcomes. In March of 2021, private equity player Vista Equity acquired a majority stake in the company for a reported $1.4 billion, more than either YouTube or PayPal enjoyed. Native ads perform well, are adapted to mobile and other platforms, and TripleLift’s tech seems poised to succeed in CTV as well.

In this entertaining and eventful discussion, Ari tells Marty [Jill is out this week] why his childhood dreams of being a brain surgeon derailed; how his parents encouraged entrepreneurialism; how a brother-in-law in the printing business may have jump-started his ad tech career; why 2012 was such a great time to be an ex-AppNexus startup; the secret to building momentum when you’re a tiny team outnumbered by rivals; and how to get gorillas like Google’s DV360 to pay attention and integrate (hint: get their customers to request it).

19. Scott McCorkle – hitting the ExactTarget at MetaCX

Scott McCorkle was a long-time leader and visionary at ExactTarget, a pioneering ESP and mar-tech hub that was acquired by the mighty Salesforce in 2012. He’s currently the CEO and co-founder at MetaCX, an outcome-based collaboration tool for software buyers and suppliers.

As Scott tells his former employee (full disclosure), Jill, and his former tough-minded Gartner analyst assessor, Marty, in this charming episode — the first mar-tech episode in this thus far ad tech-focused podcast, — he originally nurtured dreams of playing professional baseball, abandoned them rapidly for computer science at Ball State University and an MBA at Indiana University’s Kelley School of Business.

He joined firms such as Eli Lilly in product roles and ended up at IBM in 1997 when they acquired an artfully-named firm called Software Artistry, where he was V.P. of Engineering. A subsequent startup called Mezzia rode the dot-com boom up and then had a somewhat lackluster exit but still lives on in a facilities planning suite, an exhibit of stamina of which Scott remains justifiably proud.

Having met for a number of years with the co-founders of another Indianapolis-based startup called ExactTarget — Scott Dorsey and Chris Baggott, — Scott segued to a role as as President of Technology and Strategy in 2005. He was part of the team that brought ExactTarget public in 2012 and sold the company to Salesforce in 2013 for a reported $2.5 billion. He was CEO of the Salesforce Marketing Cloud until 2016, when he left to build his new journey (get it? BUILD his JOURNEY? heh heh ? … heh? … is this thing on?).

In this episode, the Indiana-based McCorkle tells Jill and Marty how he grew up in a rural area with “modest means” but loved to play around with his Apple 2e; why he never actually moved his home away from Indianapolis (and why that wasn’t actually a problem); why Salesforce made its move in 2016; and what’s so special about the time period of 2007-2008.

That latter point is one we’re going to explore in future episodes, not all of which will be about email. Enjoy!

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!”

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.)