The simple story of Yahoo! Is that they were an Internet search company that came out of Stanford during the early days of the web. They weren’t the first nor the last. But they represent a defining moment in the rise of the web as we know it today, when there was enough content out there that there needed to be an easily searchable catalog of content.
And that’s what Stanford PhD students David Philo and Jerry Yang built. As with many of those early companies it began as a side project called “Jerry and David's Guide to the World Wide Web.” And grew into a company that at one time rivaled any in the world. At the time there were other search engines and they all started adding portal aspects to the site growing fast until the dot-com bubble burst. They slowly faded until being merged with another 90s giant, AOL, in 2017 to form Oath, which got renamed to Verizon Media in 2019 and then effectively sold to investment management firm Apollo Global Management in 2021.
Those early years were wild. Yang moved to San Jose in the 70s from Taiwan, and earned a bachelors then a masters at Stanford - where he met David Filo in 1989. Filo is a Wisconsin kid who moved to Stanford and got his masters in 1990. The two went to Japan in 1992 on an exchange program and came home to work on their PhDs. That’s when they started surfing the web. Within two years they started their Internet directory in 1994. As it grew they hosted the database on Yang’s student computer called akebono and the search engine on konishiki, which was Filo’s.
They renamed it to Yahoo, short for Yet Another Hierarchical Officious Oracle - after all they maybe considered themselves Yahoos at the time. And so Yahoo began life as akebono.stanford.edu/~yahoo. Word spread fast and they’d already had a million hits by the end of 1994. It was time to move out of Stanford.
Mark Andreesen offered to let them move into Netscape. They bought a domain in 1995 and incorporated the company, getting funding from Sequoia Capital raising $3,000,000. They tinkered with selling ads on the site to fund buying more servers but there was a lot of businessing. They decided that they would bring in Tim Koogle (which ironically rhymes with Google) to be CEO who brought in Jeff Mallett from Novell’s consumer division to be the COO. They were the suits and got revenues up to a million dollars.
The idea of the college kids striking gold fueled the rise of other companies and Yang and Filo became poster children. Applications from all over the world for others looking to make their mark started streaming in to Stanford - a trend that continues today. Yet another generation was about to flow into Silicon Valley. First the chip makers, then the PC hobbyists turned businesses, and now the web revolution.
But at the core of the business were Koogle and Mallett, bringing in advertisers and investors. And the next year needing more and more servers and employees to fuel further expansion, they went public, selling over two and a half million shares at $13 to raise nearly $34 million. That’s just one year after a gangbuster IPO from Netscape. The Internet was here. Revenues shot up to $20 million.
A concept we repeatedly look at is the technological determinism that industries go through. At this point it’s easy to look in the rear view mirror and see change coming at us. First we document information - like Jerry and David building a directory. Then we move it to a database so we can connect that data. Thus a search engine. Given that Yahoo! was a search engine they were already on the Internet. But the next step in the deterministic application of modern technology is to replace human effort with increasingly sophisticated automation. You know, like applying basic natural language processing, classification, and polarity scoring algorithms to enrich the human experience.
Yahoo! hired “surfers” to do these tasks. They curated the web. Yes, they added feeds for news, sports, finance, and created content. Their primary business model was to sell banner ads. And they pioneered the field. Banner ads mean people need to be on the site to see them. So adding weather, maps, shopping, classifieds, personal ads, and even celebrity chats were natural adjacencies given that mental model. Search itself was almost a competitor, sending people to other parts of the web that they weren’t making money off eyeballs. And they were pushing traffic to over 65 million pages worth of data a day.
They weren’t the only ones. This was the portal era of search and companies like Lycos, Excite, and InfoSeek were following the same model. They created local directories and people and companies could customize the look and feel. Their first designer, David Shen, takes us through the user experience journey in his book Takeover! The Inside Story the Yahoo Ad Revolution. They didn’t invent pay-per-clic advertising but did help to make it common practice and proved that money could be made on this whole new weird Internet thing everyone was talking about.
The first ad they sold was for MCI and from there they were practically printing money. Every company wanted in on the action - and sales just kept going up. Bill Clinton gave them a spot in the Internet Village during his 1997 inauguration and they were for a time seemingly synonymous with the Internet.
The Internet was growing fast. Cataloging the Internet and creating content for the Internet became a larger and larger manual task. As did selling ads, which was a manual transaction requiring a larger and larger sales force. As with other rising internet properties, people dressed how they wanted, they’d stay up late building code or content and crash at the desk. They ran funny cheeky ads with that yodel - becoming a brand that people knew and many equated to the Internet. We can thank San Francisco’s Black Rocket ad agency for that.
They grew fast. The founders made several strategic acquisitions and gobbled up nearly every category of the Internet that has each grown to billions of dollars. They bought Four 11 for $95 million in their first probably best acquisition, and used them to create Yahoo! Mail in 1997 and a calendar in 1998. They had over 12 million Yahoo! Email users by he end of the year, inching their way to the same number of AOL users out there.
There were other tools like Yahoo Briefcase, to upload files to the web. Now common with cloud storage providers like Dropbox, Box, Google Drive, and even Office 365. And contacts and Messenger - a service that would run until 2018. Think of all the messaging apps that have come with their own spin on the service since.
1998 also saw the acquisition of Viaweb, founded by the team that would later create Y Combinator. It was just shy of a $50M acquisition that brought the Yahoo! Store - which was similar to the Shopify of today. They got a $250 million investment from Softbank, bought Yoyodyne, and launched AT&T’s WorldNet service to move towards AOL’s dialup services. By the end of the year they were closing in on 100 million page views a day. That’s a lot of banners shown to visitors. But Microsoft was out there, with their MSN portal at the height of the browser wars.
Yahoo! bought Broadcast.com in 1999 saddling the world with Mark Cuban. They dropped $5.7 billion for 300 employees and little more than an ISDN line. Here, they paid over a 100x multiple of annual revenues and failed to transition sellers into their culture. Sales cures all. In his book We Were Yahoo! Jeremy Ring describes the lays much of the blame of the failure to capitalize on the acquisition as not understanding the different selling motion. I don’t remember him outright saying it was hubris, but he certainly indicates that it should have worked out and that broadcast.com was could have been what YouTube would become. Another market lost in a failed attempt at Yahoo TV. And yet many of these were trends started by AOL.
They also bought GeoCities in 99 for $3.7 billion. Others have tried to allow for fast and easy site development - the no code wysiwyg web. GeoCities lasted until 2009 - a year after Google launched Google Sites. And we have Wix, Squarespace, WordPress, and so many others offering similar services today.
As they grew some of the other 130+ search engines at the time folded. The new products continued. The Yahoo Notebook came before Evernote. Imagine your notes accessible to any device you could log into. The more banners shown, the more clicks. Advertisers could experiment in ways they’d never been able to before. They also inked distribution deals, pushing traffic to other site that did things they didn’t.
The growth of the Internet had been fast, with nearly 100 million people armed with Internet access - and yet it was thought to triple in just the next three years. And even still many felt a bubble was forming. Some, like Google, had conserved cash - others like Yahoo! Had spent big on acquisitions they couldn’t monetize into truly adjacent cash flow generating opportunities. And meanwhile they were alienating web properties by leaning into every space that kept eyeballs on the site.
By 2000 their stock traded at $118.75 and they were the most valuable internet company at $125 billion. Then as customers folded when the dot-com bubble burst, the stock fell to $8.11 the next year. One concept we talk about in this podcast is a lost decade. Arguably they’d entered into theirs around the time the dot-com bubble burst. They decided to lean into being a media company even further. Again, showing banners to eyeballs was the central product they sold.
They brought in Terry Semel in 2001 using over $100 million in stock options to entice him. And the culture problems came fast. Semel flew in a fancy jet, launched television shows on Yahoo! and alienated programmers, effectively creating an us vs them and de-valuing the work done on the portal and search. Work that could have made them competitive with Google Adwords that while only a year old was already starting to eat away at profits. But media.
They bought a company called LaunchCast in 2001, charging a monthly fee to listen to music. Yahoo Music came before Spotify, Pandora, Apple Music, and even though it was the same year the iPod was released, they let us listen to up to 1,000 songs for free or pony up a few bucks a month to get rid of ads and allow for skips. A model that has been copied by many over the years.
By then they knew that paid search was becoming a money-maker over at Google. Overture had actually been first to that market and so Yahoo! Bought them for $1.6 billion in 2003. But again, they didn’t integrate the team and in a classic “not built here” moment started Project Panama where they’d spend three years building their own search advertising platform. By the time that shipped the search war was over and executives and great programmers were flowing into other companies all over the world.
And by then they were all over the world. 2005 saw them invest $1 billion in a little company called Alibaba. An investment that would accelerate Alibaba to become the crown jewel in Yahoo’s empire and as they dwindled away, a key aspect of what led to their final demise.
They bought Flickr in 2005 for $25M. User generated content was a thing. And Flickr was almost what Instagram is today. Instead we’d have to wait until 2010 for Instagram because Flickr ended up yet another of the failed acquisitions. And here’s something wild to thin about - Stewart Butterfield and Cal Henderson started another company after they sold Flickr. Slack sold to Salesforce for over $27 billion. Not only is that a great team who could have turned Flickr into something truly special, but if they’d been retained and allowed to flourish at Yahoo! they could have continued building cooler stuff. Yikes. Additionally, Flickr was planning a pivot into social networking, right before a time when Facebook would take over that market.
If fact, they tried to buy Facebook for just over a billion dollars in 2006. But Zuckerberg walked away when the price went down after the stock fell. They almost bought YouTube and considered buying Apple, which is wild to think about today. Missed opportunities. And Semmel was the first of many CEOs who lacked vision and the capacity to listen to the technologists - in a technology company.
These years saw Comcast bring us weather.com, the rise of espn online taking eyeballs away from Yahoo! Sports, Gmail and other mail services reducing reliance on Yahoo! Mail. Facebook, LinkedIn, and other web properties rose to take ad placements away. Even though Yahoo Finance is still a great portal even sites like Bloomberg took eyeballs away from them. And then there was the rise of user generated content - a blog for pretty much everything. Jerry Yang came back to run the show in 2007 then Carol Bartz from 2009 to 2011 then Scott Thompson in 2012. None managed to turn things around after so much lost inertia - and make no mistake, inertia is the one thing that can’t be bought in this world.
Wisconsin’s Marissa Mayer joined Yahoo! In 2012. She was Google’s 20th employee who’d risen through the ranks from writing code to leading teams to product manager to running web products and managing not only the layout of that famous homepage but also helped deliver Google AdWords and then maps. She had the pedigree and managerial experience - and had been involved in M&A. There was an immediate buzz that Yahoo! was back after years of steady decline due to incoherent strategies and mismanaged acquisitions.
She pivoted the business more into mobile technology. She brought remote employees back into the office. She implemented a bell curve employee ranking system like Microsoft did during their lost decade. They bought Tumblr in 2013 for $1.1 billion. But key executives continued to leave - Tumbler’s value dropped, and the stock continued to drop. Profits were up, revenues were down.
Investing in the rapidly growing China market became all the rage. The Alibaba investment was now worth more than Yahoo! itself. Half the shares had been sold back to Alibaba in 2012 to fund Yahoo! pursuing the Mayer initiatives. And then there was Yahoo Japan, which continued to do well. After years of attempts, activist investors finally got Yahoo! to spin off their holdings. They moved most of the shares to a holding company which would end up getting sold back to Alibaba for tens of billions of dollars. More missed opportunities for Yahoo!
And so in the end, they would get merged with AOL - the two combined companies worth nearly half a trillion dollars at one point to become Oath in 2017. Mayer stepped down and the two sold for less than $5 billion dollars. A roller coaster that went up really fast and down really slow. An empire that crumbled and fragmented.
Arguably, the end began in 1998 when another couple of grad students at Stanford approached Yahoo to buy Google for $1M. Not only did Filo tell them to try it alone but he also introduced them to Michael Moritz of Sequoia - the same guy who’d initially funded Yahoo!. That wasn’t where things really got screwed up though. It was early in a big change in how search would be monetized. But they got a second chance to buy Google in 2002. By then I’d switched to using Google and never looked back. But the CEO at the time, Terry Semel, was willing to put in $3B to buy Google - who decided to hold out for $5B. They are around a $1.8T company today.
Again, the core product was selling advertising. And Microsoft tried to buy Yahoo! In 2008 for over 44 billion dollars to become Bing. Down from the $125 billion height of the market cap during the dot com bubble. And yet they eventually sold for less than four and a half billion in 2016 and went down in value from there. Growth stocks trade at high multiples but when revenues go down the crash is hard and fast.
Yahoo! lost track of the core business - just as the model was changing. And yet never iterated it because it just made too much money. They were too big to pivot from banners when Google showed up with a smaller, more bite-sized advertising model that companies could grow into.
Along the way, they tried to do too much. They invested over and over in acquisitions that didn’t work because they ran off the innovative founders in an increasingly corporate company that was actually trying to pretend not to be. We have to own who we are and become. And we have to understand that we don’t know anything about the customers of acquired companies and actually listen - and I mean really listen - when we’re being told what those customers want. After all, that’s why we paid for the company in the first place.
We also have to avoid allowing the market to dictate a perceived growth mentality. Sure a growth stock needs to hit a certain number of revenue increase to stay considered a growth stock and thus enjoy the kind of multiples for market capitalization. But that can drive short term decisions that don’t see us investing in areas that don’t effectively manipulate stocks. Decisions like trying to keep eyeballs on pages with our own content rather than investing in the user generated content that drove the Web 2.0 revolution.
The Internet can be a powerful medium to find information, allow humans to do more with less, and have more meaningful experiences in this life. But just as Yahoo! was engineering ways to keep eyeballs on their pages, the modern Web 2.0 era has engineered ways to keep eyeballs on our devices. And yet what people really want is those meaningful experiences, which happen more when we aren’t staring at our screens than when we are. As I look around at all the alerts on my phone and watch, I can’t help but wonder if another wave of technology is coming that disrupts that model. Some apps are engineered to help us lead healthier lifestyles and take a short digital detoxification break.
Bush’s Memex in “As We May Think” was arguably an Apple taken from the tree of knowledge. If we aren’t careful, rather than the dream of computers helping humanity do more and free our minds to think more deeply we are simply left with less and less capacity to think and less and less meaning. The Memex came and Yahoo! helped connect us to any content we might want in the world. And yet, like so many others, they stalled in the phase they were at in that deterministic structure that technologies follow. Too slow to augment human labor with machine learning like Google did - but instead too quick to try and do everything for everyone with no real vision other than be everything to everyone. And so the cuts went on slowly for a long time, leaving employees constantly in fear of losing their jobs.
As you listen to this if I were to leave a single parting thought - it would be that companies should always be willing to cannibalize their own businesses. And yet we have to have a vision that our teams rally behind for how that revenue gets replaced. We can’t fracture a company and just sprawl to become everything for everyone but instead need to be targeted and more precise. And to continue to innovate each product beyond the basic machine learning and into deep learning and beyond. And when we see those who lack that focus, don’t get annoyed but instead get stoked - that’s called a disruptive opportunity.
And if there’s someone with 1,000 developers in a space, Nicholas Carlson in his book “Marissa Mayer and the Fight To Save Yahoo!” points out that one great developer is worth a thousand average ones. And even the best organizations can easily turn great developers into average ones for a variety of reason. Again, we can call these opportunities.
Yahoo! helped legitimize the Internet. For that we owe them a huge thanks. And we can fast follow their adjacent expansions to find a slew of great and innovative ideas that increased the productivity of humankind. We owe them a huge thanks for that as well. Now what opportunities do we see out there to propel us further yet again?
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