Twenty-five years ago this week, Doug Weaver was the Eastern Advertising Director for Wired Magazine when he and his team sold the first banner ad to AT&T.

From little things, big things grow. This year brands will spend over half a trillion dollars on digital advertising, representing over 60 per cent of the total worldwide advertising pool — viva la revolucion.

These days Weaver is the CEO of Upstream, a business he founded in 1998 as the first dotcom boom was inflating rapidly and which is almost as old as the internet advertising sector itself.

Doug Weaver, Founder & CEO at Upstream Group, led the team at Wired that sold the first banner ad to AT&T

To commemorate a quarter-century of digital advertising, Which-50 asked Weaver and a dozen other international and local industry leaders for their perspectives on the predictable and unpredictable ways in which the industry has emerged.

But we started with Weaver, the man who was quite literally there at the birth of the sector. He told Which-50, “I’d been a print seller for about ten years when I joined Wired. During my interview, the owners/publishers Louis Rossetto and Jane Metcalfe told me ‘… and you’ll be selling ads on our web site too!’”

Nobody had much of an idea about what a web site actually was, he concedes. “This was the age of the closed BBS systems like America Online, CompuServe and Prodigy.”

Indeed, the idea that the worldwide web would be a successful platform for advertising and commerce was no foregone conclusion, says Weaver.

On October 27, 1994, the worldwide web was only three years old, and the first commercial browser release was still several more months away, while the first ad server was still more than a year from release.

“So … the ads. With no way to dynamically serve, we could only offer hard-coded sponsorships. The web site — which Wired called a ‘cyberstation’ — was made up of original content and graphics across several sections. NetSurf, Signal, Digital Alchemy and On the Road were a few of them,” he recalls.

“Each section had a single sponsor whose small banner ad would appear at the top of each page of its section and link to the client’s jump page — many of which we built as well or handed off to Organic Online to build. There were no metrics, no reporting. You bought the sponsorship for a month and paid $15,000 to be there. Why? Because that’s what a four-colour bleed page in the magazine cost.”

The more things change

25 years on, there are still some things about the internet that haven’t changed. Weaver says the early web could get pretty weird and dark. “As we explored and promoted it as a marketing medium, it was impossible not to see the colourful nature of the denizens of the web.”

Like today, there were trolls and dark corners. “While the web has obviously brought so much to the world, I’m not surprised by the darkness as well — the data breaches, bullying, privacy issues, trolls and more.”

We also asked Weaver if there was a trend he simply didn’t anticipate, and he touched on a theme that recurred throughout many of our interviews.

“Having seen the collapse of the closed environments like AOL, Prodigy and the early Microsoft Network, I wouldn’t have predicted the rise of closed ecosystems like Facebook. That a consumer would choose to surrender so much of their data and privacy to participate in a closed, controlled environment didn’t seem possible in the days of the early web.  And the wholesale surrender of data and privacy for convenience — that’s been a bit of a shock.”

Over the last few weeks, we have been hunting down executives from those early days both internationally and locally, as we have asked them the same two questions we asked Weaver: with the benefit of hindsight, what was predictable and what was unexpected, as well as what they were doing at the time.

Amobee ANZ Managing Director Liam Walsh, for instance, was working at Lintas, and later did stints as the Managing Director of Microsoft Advertising and then as the MD of Facebook in Australia. Walsh says the fact that digital would overtake print was predictable, but the emergence of auction-based pricing took him by surprise.

Michael Gill was the Deputy Editor of the AFR in October 1994

Michael Gill (an occasional Which-50 contributor) was the Deputy Editor of the Australian Financial Review and later became that newspaper’s CEO and Editor-in-Chief, a post he held for over a decade. Gill says the scale effect of aggregation driving ad yields down should have been obvious (though it wasn’t to many of his peers).

Indeed for a time the AFR was reportedly more profitable than the Wall Street Journal, the Financial Times and the New York Times combined — but only because they were all losing money while the AFR maintained strong profits right up until the GFC by avoiding the commoditisation trap. Gill meanwhile (along with the co-author of this article, Andrew Birmingham) controversially introduced Australia’s first large-scale media paywall.

Gill says the thing he didn’t predict was the impact on the actual editorial product and what he describes as “The conversion of traditional media to populist rhetoric.”

The emergence of search

In October 1994, Tony Faure — now Chairman of Ooh Media — recalls he was in London publishing technology magazines about the growth of PC networks and bulletin boards. “If you couldn’t see the digital revolution in media coming from there, you would have to have been blind.”

Tony Faure, Chairman of Ooh Media, and employee number one at Yahoo! in Australia in the mid-nineties

On returning to Australia he became Yahoo! employee number one down-under, building the business from scratch into one of the top two portals in the country. His last executive role was as the CEO of Nine Entertainment Co between 2006 and 2008. These days he is a professional director and advisor. 

In Faure’s views, it was always likely that digital would evolve into a direct response model rather than a brand one. “Even from the earliest days the designers focused on consumer UI and were not at all sympathetic to what brands needed. Only after the emergence of Google did that change, and that change was too late.”

And as to what was unexpected, “This will sound crazy, but the emergence of search advertising surprised a lot of people at the time, particularly at Yahoo! They believed that the users of directory/listings services would never accept advertising in the product mix.”

This online thing won’t take off

As a measure of how insignificant digital advertising was in those early days, the IAB only started tracking local digital ad sales in 1999, five years after that first AT&T placement.

Growth of digital advertising in Australia. Source: IAB Australia

When that first banner ad appeared, Gai Le Roy — now CEO of IAB — was working for the marketing team at London Business School.

“We had recently launched our first web site which was basically one page with a ridiculously beautiful and heavy image that took forever to load and then really just gave our email address for inquiries.”

Le Roy started working in digital advertising specifically in 1998, joining Australia’s first digital consultancy www.consult helping to compile data on the local ad market when there were about six publishers.

Gai Le Roy - CEO of IAB Australia
Gai Le Roy, CEO, IAB Australia,  started working in digital advertising in 1998 joining Australia’s first digital consultancy www.consult

“The whole market was worth $400,000 a month. It was an amazing time of growth, trying new things, every second person telling you that this online thing wouldn’t take off and Telstra execs wearing black skivvies.”

That early era was dominated locally by what was often called the “top 5”: Yahoo!, ninemsn, f2 (Fairfax’s digital business) News Interactive & Sensis and MediaSmart (Telstra directory business).

She also recalls a range of wonderful and sometimes weird smaller sites. “I remember in the late ’90s and being pitched in market to advertisers & VCs as the next big things. Strangely a lot of the late ’90s/early ’00s trends wouldn’t be out of place today — youth publishing (Scape), women’s sites (iVillage), cybercurrency (Beanz) and auctions (”

She says the growth of video content and advertising was a predictable trend. “Working at ninemsn in the early days I witnessed first hand how much people wanted to catch up on things they had missed on A Current Affair, Getaway or even cricket on CricInfo. This, combined with the inevitability of faster connection speeds (eventually), really did point clearly to a future where video advertising would be a huge opportunity for publishers and marketers.”

On the other hand the local IAB boss says she was surprised by the growth of social media. “Messaging as a communications tool (MSN Messenger was huge) I totally understood, but I was an early sceptic and slightly dismissive of the idea that people would want to share information about themselves publicly.”

Tremendous growth was predictable

“I was working as an IT administrator at a financial services company, Copper Mountain Trust. I had proudly just installed my first email server (Microsoft Mail) and had just built my first corporate web site using my trusty Vi editor, “ says Darren Guarnaccia, Chief Product Officer, Crownpeak.

Darren Guarnaccia, Chief Product Officer, Crownpeak

He would go on to spend ten years with Sitecore in strategy, product, CX and partnership roles attime when marketing technology was just taking hold.

Asked about the most predictable trend, he told Which-50, “Its tremendous growth. Looking at what we now call traditional media, it also expanded massively. From its humble origins of three channels to the explosion of hundreds of TV channels and 24 hour news should have prepared us for the massive explosion of digital advertising.”

Like others we interviewed, he alluded to the unintended consequences of digital marketing when asked about what he hadn’t expected.

“The sheer creepiness of it all. I never thought I’d have conversations with my wife about how Facebook is listening in on her conversations. As many times as I’ve explained why this really isn’t happening, so many people believe it is happening. The reality is that ad platforms have access to so much data, including who you are standing next to, and what friends in your network are looking at, to predict what you’ll want to see next.”

The Omni-fog

In late 1994, Liz Miller, now the SVP Marketing at the CMO Council in the US was the PR manager for the Continental Indoor Soccer League selling indoor soccer to Americans in the days before Major League Soccer. “We would shout down the hall that we were “going on the internet” and then we would fire up the AOL disk and the modem. We were very ahead of our time!”

Senior Vice President, Marketing at the Chief Marketing Officer Council

According to Miller, one of the sadly predictable outcomes of digital advertising was the misuse and failed application of omnichannel marketing. “Marketers are living proof of the concept of the Fog of War. The entire concept of a total lack of situational awareness by those on the frontlines engaged in war is the absolute picture of modern advertising as we have saturated digital channels with random acts of advertising.”

This, she says, has created a fog that blocks the view of the customer and, conversely blocks the customer from a clear path to their needs. “Every channel we see, we shove advertising into it….look at email. Email was going to save engagement. It was going to remove the waste, clutter, and madness of the junk mail crammed mailbox. Yet here we are in the year 2019 and print is a disruptor being leveraged by brands to grab attention. Why? Because emails were made to be ignored.”

As to what has surprised her, her answer is succinct. “Snapchat. I still don’t get it. I mean I get it is a channel people love and some brands are leveraging effectively, but yeah, I don’t get it. Still can’t imagine ever getting on board.”

The death of the banner ad

Six months after that first banner ad, Pippa Leary was working as a freelance journalist in Los Angeles and was commissioned to write a piece for the Australian magazine 21C, which was created by the Australian Commission for The Future. 

She was writing a rags-to-riches startup story about the founders of a CD-ROM Magazine company, Electro Media, who asked if she wanted to join them to be trained in digital production. That was the basis of her introduction to digital media. Leary subsequently worked in senior executive roles at Nine and Fairfax, and was a board member of the IAB in Australia from September 2017 to July 2019. These days she is the CEO of Swift Media. 

Pippa Leary CEO, Swift Media

“It was obvious to me that display advertising would become completely commoditised when ad networks started aggregating and monetising the long tail. We went from limited, high-quality inventory from professional publishers to unlimited, user generated and non-professional inventory — guaranteeing the de facto death of the banner ad. I’m amazed some people were surprised by this,” she says.

On the other hand, the emergence of search as the dominant category was a surprise. “I remember sitting at my desk at Ninemsn talking with Christa Davies when she said to me, ‘you’ve got to take a look at this new search engine called Google, it’s really good’. Good as it was, I don’t think either of us could have imagined it would become the dominant advertising powerhouse of today.”

The Internet is going to be big

These days Daniel Benton is the General Manager of NEO, part of GroupM, and a global performance agency that works across programmatic, social, paid search, analytics, technology, organic search, affiliate marketing, e-commerce and across traditional channels. When that first ad appeared he wasn’t even in the industry.

“My first exposure to digital was selling the first ad on New Zealand’s online Yellow Pages in 1997. These were the days of dial-up internet when page load speed was measured in minutes, email chain messages were a thing and brands like Lycos, Alta Vista, and Dog Pile were trying to crack search. Back then, I had a vague sense the internet was going to be big.”

Unlike Leary, Benton sees the rise of search as inevitable. “Google elegantly delivered great utility for users by democratising access to information while allowing marketers to tap into user intent with precision and scale. And measure the outcome. This is a seductive and powerful combination.”

Yet Benton concedes he was blindsided by the rise of vloggers and influencers. “I would never have imagined back in 1997 that an eight-year-old could earn $25 million a year making videos of toys being unboxed and played with.” 

Denial and ego

These days Denise Shrivell, founder of Mediascope and the manager of Peggy’s List, is a leader in online social activism (and has earned the acrimony of publishers like News Corp for her troubles). But in 1994 she was just back from London where she worked for DDB Needham. After a time planning and buying ads for Halmarick Media Services she worked with BRW Publications as an ad sales rep for Personal Investment magazine. “No banners back then but we couldn’t stack that magazine with more high yield, double-page spreads if we tried,” she says.

Denise Shrivell, founder of Mediascope and Peggy’s List

On the matter of predictability, Shrivell suggested “That the advertising supply/demand ratio would blow out through low barriers to entry from other publishers and platforms.” More to the point, the disruption of media markets that followed was likewise inevitable.

“There was a lot of denial and ego by the big publishers, thinking they held a unique position in the changing publishing landscape. Online content was of course largely given away for free and opportunities were missed. I recall the infamous story Eric Beecher (now at Private Media) tells, where he tried to tell the Fairfax Board about the issues ahead of them and the then-Chairman [Roger Corbett] threw a very thick Saturday edition of the SMH on the table basically saying ‘don’t tell me people will use anything other than this to find real estate every Saturday’. Audiences clearly had other ideas.”

Fairfax, it’s worth noting, no longer exists.

The unpredictable outcome she describes reflects the work she does today.

“Disruption, digital data and volume-based business models have played a fundamental role (not the only role) in publishers and digital platforms being used by various forces to exploit vulnerabilities in our community and negatively impact our democracy. Also the lengths some publishers are going to hold back the inevitable tide of digital evolution. As we’ve seen before, audiences have other ideas. Actually maybe all of this is imaginable and it’s history repeating. We live in interesting times.”

The exponential growth of adtech and martech

These days Scott Brinker is one of the most recognisable names in the marketing technology industry, by virtue of the annual marketing technology landscape map which he and his team at publish.

Scott Brinker, Editor at, VP Platform Ecosystem at HubSpot

But back in October 1994 he was running a company that made BBS (bulletin board system) software, to let companies and individuals run their own miniature online services with dial-up connections. “It was a precursor to the commercialisation of the internet, and we were in the process of being totally disrupted by the web.”

Brinker, like others we spoke to, said the extraordinary growth of online advertising is actually one of the more predictable outcomes. “Where the audience goes, the advertising dollars will follow. In 2019, US digital ad spend finally surpassed traditional ad spend on print, TV, and radio.”

But the man whose name is synonymous with the exponential explosion of adtech and martech software — over 7,000 solutions globally in 2019 — still finds this trend surprising. “No business software market in the early ’90s looked anything like that,” he told Which-50.

Mobile changes everything

“My memory of 1994 is a little fuzzy, but I think I had just left IDG and was just getting started at Doing Words, which was basically anything I could do to make money,” says Alan Jones, General Partner at M8 Ventures and Entrepreneur-in-Residence at UTS. Jones is ubiquitous in the Australian startup community, and his corporate credits include Microsoft, IDG, and Yahoo!

“For me at least, it was absolutely predictable that as an industry we would gradually learn how to find out more about our audience and target ads based on their online behaviour, using algorithms to do all the work. Though before the invention of the cookie, I wasn’t sure how we were going to do it (my assumption was your ISP would subsidise your access in return for you responding to customer demographic questions).”

Alan Jones, General Partner, M8 Ventures.

He tells Which-50, “When we first got started serving ads at Yahoo! (and for a few years after) scheduling ads meant basically uploading a huge CSV file you’d created in Excel that included all the scheduling information and referring to a GIF file name for the ad creative that was included in a big zip file. It could take all night to process that CSV and start the ads serving, and there only had to be one error in one line of a few thousand lines of ads to make you have to start again.”

He recalls there were many times the ad scheduling team was up all night, grabbing only a few hours of sleep in the middle of the day before starting again. “There was so much money to be made from these ad campaigns.”

Much less predictable was the impact of smart mobility. “I don’t think anybody could have predicted that the smartphone was coming and that one day the majority of our online ads would be served on mobile apps and browsers.”

He says that too many innovations were required in too short a period of time for that to be easy to predict.

“I was working with an Australian-founded mobile startup that developed a mobile-native social network while Facebook was still only available on desktop browsers and within US college campuses, so we thought we knew a thing or two about mobile app behaviour. Our goal was that one day, the world would wake up in the morning and the first thing they’d do would be to check their phone to see what their friends were doing. So while we couldn’t have predicted the smartphone was coming, as soon as we saw the iPhone on launch day, we immediately knew that this would be huge.”

It was going to democratise access to online services and it was going to allow us to have the internet with us in our pockets, all the time, he says.

Where to from here?

To mark the end of our review of 25 years of digital advertising we asked the man who helped to sell that very first banner what he believes the digital ad industry needs to get right to ensure it’s around for another 25 years

Looking for someone to blame, here is a good place to start — a reunion of sorts of the Wired team. Left to right: Far left (unidentified), Carl Steadman, early Hot Wired developer and founder of; John Plunket, Head of Design for Wired; Kevin Kelly, executive editor; Jonathan Nelson, former Wired Intern, founder of Organic Online and now global head at Omnicom; Louis Rossetto, founder and editor of Wired and Hot Wired; Doug Weaver, Wired #1 employee in New York in the tie; Jane Metcalfe, cofounder and Wired president; Andrew Anker, CEO of Hot Wired; Barbara Kuhr; co head of design for Wired (along with John Plunkett) and design lead on Hot Wired; and Rick Boyce, VP of Sales for Hot Wired. Image source Doug Weaver.

“The digital ecosystem has gone through its own version of the subprime mortgage crisis over the past few years. There’s been a real lawlessness in the rush to cash in. As a result, we’ve cared about nothing but more — more data, more impressions, more ads served to more people more frequently.”

According to Weaver, “We ended up with rampant fraud, Cambridge Analytica, fake data, a bad user experience and a minor rebellion among marketers. We’ve got to get back to what’s real. Real consumers engaging with real content and experience forming real data relationships with media and brands. If we don’t, it’s just dystopia.”

Previous post

Oracle Co-CEO Mark Hurd dies at 62

Next post

Which-50 Awards: Verimoto — Best in Digital Commerce