25. Jeremy Ring – We Were Yahoo!

Jeremy Ring was the first on-staff salesperson at Yahoo!, joining just before the IPO in in 1996. He entered the Yahoo! rocket very early and rode it through its rise and rise until shortly after the dot-com bust of 2001, when he decided “it was time” and disembarked. Subsequently, Ring got into politics in the State of Florida as a State Senator, and he now runs the GTM Group consulting firm.

Jeremy is the second in our (so far) two-part interview series featuring early, early Yahoo! employees and FoJ’s (Friends of co-founder Jerry Yang) who lived to write a book about it. The first was Episode #23’s David Shen, author of Takeover. Jeremy’s own book is called We Were Yahoo!, published in 2018 and spanning the period of Ring’s Yahoo pre-history to a recap of the company’s management steps and missteps since he left.

Starting as a media planner in New York City in the early 1990’s, Jeremy actually replaced our previous guest Steven Comfort at the pioneering agency Messner Vetere and placed some of the first online banner ads for clients such as MCI. He began to work with an agency called Interactive Media Sales, which won the Yahoo! media sales RFP before it had its own sales team.

Eventually, as Jeremy tells Marty in this far-ranging chat [Jill is out this week], Yahoo! decided to hire him as their first sales staffer and his Hoboken apartment became the company’s East Coast HQ around the time of the IPO. Jeremy worked closely with co-founder Jerry Yang – whom he describes as “beloved” and someone who “remembered your name” – and co-founder David Filo, certainly less exuberant externally but “internally … very active.”

The dot-com boom times were fun, of course – “You give a bunch of people in their twenties a lot of money and they’re going to find a way to have fun,” he says – but “we were not ‘The Wolf of Wall Street.’ … It was not a sex and drugs and rock and roll kind of place.” Despite the occasional trashed hotel room and high-stakes poker game.

As he describes it, Jeremy saw the dot-com crash coming around the time that many of his customers, preponderantly venture-backed dot-com companies, stopped paying their bills. He sold Yahoo! stock, left after the crash and never looked back.

Yahoo! had opportunities to acquire rising stars like Google and Facebook, at various points, but Jeremy thinks its biggest preventable mistake during his tenure was its elevation of product over sales, minutely respecting an uncontextual reverence for search-as-editorial that made it much too late to see the business opportunity in paid search and CPC ads.

And what are his feelings looking back at his Yahoo! experience during those extraordinary years? “Mixed,” Jeremy admits. “But Yahoo! definitely changed the world.”

24. Tolman Geffs – banking on ad tech and media

Tolman is a long-time investment banker and advisor to luminaries in the ad tech, media and data-driven enterprise world. He’s the man who sold the mighty AdExchanger to Access Intelligence in 2017, almost 10 years after its founding, and he’s been an observer-participant in the #PaleoAdTech universe for more than twenty years.

As he tells Marty [Jill is off this week] in this wide-ranging and perceptive chat, Tolman has been around long enough to see a number of market cycles, and “we never learn,” he says. “We’re approaching another one now,” he warns, but “sit tight … the universe doesn’t end.” Long-term gains to productivity based on connectivity and data-driven methods are adding meaningful, sustained value into the economy.

Tolman is currently Executive Partner at BrightTower, an investment banking advisory firm, and before that he spent 16 years at the Jordan Edmiston Group (JEGI), also an independent i-bank.

While he was at JEGI — as attendees at IAB and AdExchanger and other conferences will no doubt remember, — Tolman was involved in a number of ad tech, mar-tech and related deals such as Acerno’s sale to Akamai and i-Behavior’s sale to KBM Group.

Starting life as an aspiring physicist, Tolman ended up in NYC at now-defunct Lehman Brothers as an M&A analyst. After a tour of duty through the benighted corridors of McKinsey, he ended up in the media business, eventually as CEO of a company called Internet Broadcasting Systems, which built the biggest network of local TV news sites in the U.S.

At IBS from 1999 to 2004, Tolman experienced the range of boom-to-bust emotions and found himself looking for a transitionary perch by networking with the legendary founding partner of JEGI, Wilma Jordan. Joining the bank in 2004, he saw the rise of programmatic platforms, the twilight of “100% markup, 50% margin” ad networks, and the transformation of the ad tech industry from “a teen dance party” to a “mature, more reliable” set of processes, practitioners and rules.

In this episode, Tolman explains why most ad networks ultimately failed; why the “programmatic gold rush” never quite happened; what’s so special about the Trade Desk and Jeff Green; and why the IAB’s long-time CEO Randall Rothenberg deserves a lot of credit for clarifying the rules of the game.

If you’d like to see Tolman himself in action back in 2010 at an IAB conference, check out this YouTube video:

Paleo Pellet: How DoubleClick worked

In this brief (10:42) episode, Marty explains how the original DoubleClick ad server technology worked, based on a reading of the original patent, filed in 1996 and granted in 2000.

If you’d like to enjoy the patent yourself, you can do so here. It was US patent number 5,948,061 and was assigned to Dwight Merriman and Kevin O’Connor, the co-founders of DoubleClick. Its title: “Method of Delivery, Targeting, and Measuring Advertising Over Networks.”

If you’d like to learn more about the mighty DoubleClick, you can enjoy our podcast interviews with former CEO Kevin Ryan and co-founder Kevin O’Connor in the archives.

23. David Shen – inside Yahoo!’s ad revolution

David Shen was employee #17 at Yahoo!, hired by founders and Stanford classmates Jerry Yang and David Filo to shepherd the user experience — and eventually the ad experience — for the pioneering and absurdly successful directory and portal to the nascent internet.

David is also the author of the best behind-the-scenes look at Yahoo!’s ad evolution, a book called “Takeover: The Inside Story of the Yahoo Ad Revolution” (available from Blurb and Amazon).

A digital ad historian after our own heart, David has also collected and archived a range of important Yahoo! creative executions from the 1990’s and early 2000’s that can be enjoyed on YouTube:

David designed the Yahoo! logo and was there when the first grainy banner-ad image was pushed live in 1995 to the chorus of lead engineer Donald Lobo sighing, “We sold out.”

“I think there was a pervading notion or hatred … of advertising,” David tells Marty and Jill in this reflective episode. “In fact, there were a lot of people who had this dream: Could we build a Yahoo! without any advertising?”

Intriguingly, after a troubled experiment with the ad server NetGravity (later acquired by DoubleClick), Yahoo! chose to develop and use its own in-house technology for ad serving, insertion, scheduling, accounting and measurement. (For a reason David reveals in the interview, these tools were all named after famous Kennedy family members and associated individuals.)

Yahoo! was a bellwether of the dot-com boom, going public on very little revenue in 1996 — only two years after it was founded in a famously messy trailer on the Stanford campus, — and rising up and up to a peak valuation of $128 billion in 2000, more than Ford and Chrysler combined.

That same year, Yahoo! was the most popular website in the world. Soon, things changed.

“You think that something like that’s always doing to last, right?” says David. “Well, you know what? The music stops.”

At its nadir, Yahoo!’s stock was priced at $8 for a valuation of $5 billion, 96% below its peak. It entered a period of rotating CEOs and halting M&A that continues to this day.

After the dot-com bust, Yahoo!’s management became more amenable to ad formats that would have been deemed too intrusive pre-2001. Thus the notorious Yahoo! home-page takeover ad so beloved of upper-funnel advertisers was born, inaugurating an era of D-HTML and Flash-driven creativity that tested (and often broke) the outer limits of home browser connectivity.

Iconic early examples of HPTO’s (as the media agencies invariably acronymized them) were the birdseed-themed Ford Explorer launch, Britney Spears’ beloved Pepsi spot, and creatives for films such as The Incredible Hulk and Pearl Harbor that were perhaps more exciting than the source material.

David left Yahoo! in 2004 while his friends Jerry and David were still very much in evidence. He’d witnessed the glorious rise and thudding fall of the exclamation mark, and he was ready to turn the (web) page.

Today, David is a life and health coach with CoachDShen, LLC and enjoys biohacking, coaching and living his best life in Northern California.

And if you’d like to see early footage of the Yahoo! founders looking like the kids they actually were, this Stanford-produced video is 30 minutes of fun:

22. Michael Provenzano – issuing an Invite (Media) to Google

Michael was one of the co-founders of Invite Media in 2007, with college classmates at the University of Pennsylvania. He and co-founders Nat Turner and Zach Weinberg met in an entrepreneur’s club in college, and Nat was inspired by a summer internship at pioneering video ad network VideoEgg to build a dynamic-creative ad platform. This morphed into a semi-baked idea to develop Facebook apps plus an ad server … until a recruiter connected the quixotic grads with ad tech paladin Brian O’Kelley.

In “typical Brian” fashion – recalls Michael in this lively interview – O’Kelley told them they were snorkeling a suboptimal reef and should build a bidder. Fresh from the Right Media acquisition into Yahoo, O’Kelley was launching his next venture called Adnxs (later AppNexus), and he astutely foresaw an ad market bifurcated into buy- and sell-side platforms on either side of a real-time exchange.

So the idea for Invite actually emanated from O’Kelley and was (so he told me in an interview a few years ago) the recipient of technical guidance from the “godfather” of ad tech himself, Dr. Boris Mouszykantskii now of IPONWeb.

Michael vividly recalls Invite’s sketchy early office space and frat-like atmosphere (43 boy-men, 2 women); the sleepless nights caused by payroll-making agita and rival DSP Turn; and the ultimate fear that the lack of real-time inventory – beyond non-real time Right Media and AppNexus itself – presaged the boys being stuck with a solution in search of a problem.

Then around 2008, things changed. Google released its real-time exchange, AdX; the Ventura-based Ad:ECN from pre-Trade Desk visionary Jeff Green appeared; and other DSPs began to pick up speed. Suddenly, there was inventory for the bidder to bid on – and the business started to grow beyond Right Media connectors, serving mainly ad networks “who wanted more control.”

Google called in 2010 and acquired Invite for a reported $81 million, explicitly as an investment in “exchange bidding.” Coming soon after its acquisition of AdMeld (an SSP), Invite formed the basis for its DSP which was renamed DFA and now DV360. Presumably little of the original code remains, but the ROI on the original Invite investment is staggering.

Shortly after the acquisition, Michael took time off to travel to Italy and came back to co-found Vistar Media, a company that began in 2011 to provide programmatic methods – data-driven, measurable – to digital out-of-home, a slow-growing category with little programmatic inventory. Admitting that getting an “old school category moving” has been “harder than I thought,” Michael persevered into building a 145-person, profitable company.

Then COVID hit. Despite an existentially trying year, Vistar is back to record-breaking quarters, Michael told us and AdExchanger Talks recently. Also in this episode: why TripleLift is a company everyone should emulate; why there were “bodies” in the company’s temporary NYC co-working space; and why Michael doesn’t really think they sold Invite too early.