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We Were Yahoo!: From Internet Pioneer to the Trillion Dollar Loss of Google and Facebook

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Only someone from the corporate inside could explain how Yahoo!—one of the greatest brands in corporate history—could rise to the greatest height ever seen in American business…and then crash into oblivion.

For anyone paying attention, the beginning of the end for Yahoo! began with decisions made by the first team of executives while the company was on its way up, which set the stage for horrific decisions made by subsequent generations of Yahoo! leadership. Most decisions were either pure incompetence or just lack of vision by CEOs from 2001 to the present.

Twenty-one years after its incorporation and sixteen years after its stock peak, Yahoo sold for 96% less than its value on January 3, 2000, when it had closed at an all-time high of $118.75 per share, resulting in a market capitalization of $120 billion. Wall Street valued Yahoo!, at that time in business less than six years, higher than it did Disney, News Corporation, and Comcast combined . Also on that day, the iPhone was more than seven years away from launch, Google was four years from its IPO, Amazon was hemorrhaging money, and Mark Zuckerberg was still in high school!

At the end of 2016, the top seven businesses on the list of the highest-valued companies in the world by market capitalization include Apple at #1, Alphabet (Google’s Parent Company) at #2, Amazon.com at #5, and Facebook at #7. Those companies combined are valued in excess of $2 trillion more than the price Verizon paid to acquire Yahoo!

Yahoo!’s story is one of missed strategies, failed opportunities, and poor execution. Early decisions to de-emphasize search features, undervalue Google, and overplay Yahoo’s hand in the Facebook negotiations haunted the rest of the company’s existence. In addition, factors outside of Yahoo’s control—most notably how irrational expectations of Wall Street created an environment where short-term decisions were made at the expense of the long-term good.

The story of Yahoo! is a cautionary tale not intended for the faint of heart.

240 pages, Paperback

Published January 23, 2018

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Jeremy Ring

4 books1 follower

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Displaying 1 - 19 of 19 reviews
Profile Image for Andrew Smith.
1,255 reviews991 followers
January 25, 2020
Having recently listened to an audio version of In the Plex: How Google Thinks, Works and Shapes Our Lives it created a desire in me for more information on probably the key forerunner to Google. Yahoo is referenced many times in the Google book, it’s clear they had paved the way for later technology companies to push on and further leverage the opportunities presented by the World Wide Web. In this book a former executive tells of his time at Yahoo and how and why the company later fell from prominence and was ultimately bought by Verizon it what has been called the saddest deal in tech history.

Jeremy Ring joined Yahoo in the mid 1990’s and stayed on for five years. His background had been in advertising and in the course of doing business with Yahoo he’d befriended Jerry Yang, one of the co-founders. At this stage Yahoo was in its infancy and Yang and fellow co-founder David Filo were two of only a handful people working at the fledgling tech company. Yahoo designed a system to categorise web sites, developed a web portal and a search engine and then added an advertising service to generate revenue. They were a pioneer of the internet age in the 1990’s and at its height its website was one of the most visited globally. Ring walks us through his early life and his time at Yahoo and then provides his thoughts on what went wrong with the company after he left.

The autobiographical element (essentially the first half of the book) was interesting enough, particularly a section in which Ring tells of how he was targeted by a blackmailer - a strange and disturbing tale indeed! But the meat of the book is the story of Yahoo. After rising to prominence and creating huge wealth for all the early Yahoo team it started to fall behind other, newer technology companies. According to the author, this boils down to a lack of foresight and innovation, a catastrophic series of missed opportunities (the company, it seems, spurned early chances to buy Google, Facebook and eBay), and a failure to properly integrate the businesses they did acquire. Much of this is blamed on the appointment of a series of badly chosen CEO’s, with Terry Semel receiving the majority of the flak. By the time they brought in a leader that might have avoided the disastrous slide (Marissa Mayer from Google) it was too late.

The format is slightly jumpy and a little repetitive as the author struggles to find a balance between telling his own story and that of the tech giant. The writing style is odd too – a little ‘old fashioned’ and stilted and with many of his points supported by multiple analogies and sometimes a ranting diatribe. The book did, in the end, provide me with what I was looking for, though perhaps not in the way I was looking for it. Therefore, three stars is as high as I can go with this one.
Profile Image for Chris Esposo.
680 reviews59 followers
January 3, 2019
A painfully mediocre exposé on Yahoo, written by a former sales exec who jumped ship right before the tech bubble burst of 2001. Although the title (and release timing of 2018, just a little over a year after Marissa Mayer stepped down from the firm and ended it as an independent entity) suggest it's on the decline of Yahoo in the mid-late aughts, this author didn't witness any of it firsthand. He wasn't connected or a player in the company at the time by his own admission.

The book starts off by outlining the author, Jeremy Ring's youth. It states that he was an average student, who struck rich in the early ad-tech space in the late 90s, first by getting a gig at an early internet ads company in Brooklyn, then pivoting his way to his firm's most interesting client at the time, Yahoo. "The Big Short" or "Moneyball", it is not. it's about a Joe Schmo who got lucky, fair enough.

Except, there's no story. Ring helps w/ sales during the buildup of the 90s tech bubble, sells ads like gangbusters, then splits. What did he do in Yahoo? What was his analysis of what went wrong w/ Yahoo? To Ring, it all has to do with a series of poor choices in M&A. First, by not acquiring Google for $1 million in the late 90s, then not acquiring FB in mid-oughts, then not being acquired by Microsoft in the 2010s.

In short, Jeremy Ring provides the banalest analysis of Yahoo's decline. Any major technology firm has a LONG list of misses and "could haves". From Xerox to IBM on the declining side, to Google and FB on the not-declining side. Specifically, not exploiting the GUI for Xerox (which was itself taken from Licklider), IBM missed the boat when an engineer developed "Paige Rank" before Larry Paige did in 2004 or 2005. That person is now an obscure faculty at Cornell.

In summary, Google and FB have WAY more failed moonshots than successful ones. Yet, they are still very successful. In fact, one could say Google has pretty much failed in almost everything they've done outside of Search, the Youtube acquisition, and the Android acquisitions (with some minor victories and potential future victories in cloud-computing, though that's a toss-up w/ AWS). It's basically ad-revenue from Search that keeps them in the black. Anyone with more than a passing familiarity with recent tech-history can see that a list of should-haves or could-haves is not enough to explain the failure (or success) of a large tech firm.

Could Yahoo's decline have anything to do with the fact that their product was effectively a hand-curated hash-list, whereas what lays at the heart of Google or FB etc. are machine-tuned algorithms? Maybe? But Ring is not equipped to give that sort of analysis or commentary.

Some portions of the book are interesting. A recounts a moment after he left Yahoo when a huckster tried to scam him for 4 million dollars by pretending to be a member of the Mafia for instance. First world problems. Reading about these misadventures was not why I picked up this book though.

Ring attempts to pepper the book with humor, and mostly falls flat. There's liberal use of Star Wars/Star Trek analogies to describe the context of some business situation, Google as the Jedi, Microsoft as the "Empire" etc. The author definitely tried too hard in this aspect.

On the positive side, I do believe Ring's comments on hustling your way in NYC, if you don't come from a "Harvard" or ivy-league is pretty spot-on. His description of the internal corporate politics of large northeastern firms also "rings" (pun-intended) true. Also, his commentary on the early ad-tech space right before Google emerged as the definitive search leader was interesting. There's just not enough of this kind of content and commentary to justify reading parts of this book.

It turns out that after cashing in his options in 2001, Ring eventually ran for Florida state Senate and served for few years. Now he's possibly running for Florida governorship, for the Democrats. running on making Florida the "Silicon Valley" of the South, great.

So essentially, what is advertised as a business/tech-case of Yahoo on the surface, is just a platform for someone to run for office. One day, someone will definitely write a great case-study on Yahoo, it deserves it, and I'm sure we'll all learn from that text when it's written. Unfortunately, this is not that book. Not recommended
Profile Image for Ruth.
Author 7 books120 followers
December 9, 2019
A few actually interesting parts, mostly meh or high-level known stuff. I wouldn’t recommend reading it unless you’re specifically interested in how Yahoo did ads and monetization, the pre bubble choices they made, and why. The overview of CEOs is neither awful nor insightful. Nothing really about infrastructure or things most people in tech vs business might find interesting about early yahoo.

Jerry Ring himself is so boring he put capitalism on his life focus thing along with his children. Yikes. He doesn’t even make this an interesting thing, which even someone I thoroughly disagree with can do. The subject matter as a whole might’ve done better with a better writer or ghost writer.

Also ends with a paen to his time in Florida legislature and uncritical positive Silicon Valley spiel when anyone can see the effects of Silicon Valley on regular folks who lived there and even on tech people being priced out has been awful. Big tips and other supposed positive effects on the community don’t mean much if you’re paying $1600/mo for a 300sq ft studio apt (source, my husband lived in Menlo Park for work in 2017/18 and paid that much). Generally out-of-touch and boring personal stuff interspliced with the history bits. I’d give it a miss or flip through the salient chapters if you find it used. I wouldn’t call it DNF but I did put it down before finishing the last chapter because ...paen.
Profile Image for Rick Wilson.
959 reviews413 followers
May 12, 2021
I don’t know what this book wants to be. Part “fuck you” to people who didn’t hire the author before he worked at Yahoo, part mediocre autopsy of Yahoo. It’s ok. I wouldn’t recommend it to anyone not deeply interested in Yahoo.
Profile Image for Moshe Mikanovsky.
Author 1 book25 followers
December 20, 2018
Rounded up to 4*. I am one of the only people I know that is still using Yahoo email. I got my first email address back in 1995 when I finished my army service and joined my first job. It was great! I remember Yahoo being the first page for everything - the search, the portal to different sort of sites, and the content they started building in. I also remember the first ads they used to put on strategic places on the page. These were the golden days of Yahoo, and since then they fell, and how glorious was their fall. Till these days, still using the same email account from 1995, but I don't think Yahoo ever made any money from me. I never cared about any of their sports or finance content, nor clicked on any of their ads. I replaced, like most of the globe, their "search" with Google, and really, the only thing I kept, mostly out of some nostalgia, is the same old email account.

In his book, Ring describe the early days amazing growth, and the bad decisions made afterwards by all of its leaders, that led to its demise. There is a segue in the middle of the book to the bizarre yet scary ordeal Ring and his family had to endure from a nut-case who decided to blackmail him. A bit out of place for the topic of this book, but I get why Ring included it in. After all, from the day he joined Yahoo, it changed his life for the best and the worst.
Profile Image for Gary.
143 reviews
May 18, 2021
This guy is undoubtedly the worst writer I've ever encountered. His voice oscillated between smug jackass and informed insider with about a thousand gradients in between. He made allusions and then explained the allusion. He tried to sound hip and edgy and ended up sounding like someone you'd be seated beside on a long-haul flight from hell. There was little to no internal consistency within the organization of the book and that too affected the voice: Is this a narrative? Is this an analysis? Is this a diatribe? Is this a tantrum? It's horrible. The only reason I continued was to see just how bad it could get.
1 review
May 29, 2018
Ok but long winded.

I started using yahoo when it first came out. It was great at one time, but now has too many problems and I was wondering why. I was hoping this book would explain that, but it barely touched on the technical aspect of yahoo and instead focused on advertising and shareholder price. And about midway through the book it got long and boring.
Profile Image for Slackorama.
54 reviews4 followers
May 14, 2021
Why use one metaphor when you can use 4 or 5?
Profile Image for Rena Sherwood.
Author 2 books49 followers
June 1, 2025
Around July 2, 2014, I was one of hundreds of freelance writers that received a devastating email from Yahoo! Voices, then my biggest client:

The entire website was being shut down in 28 days. No more articles could be published -- even from contractors like me that had to produce at least three per month. I'd already delivered the articles -- and now I wouldn't get paid for them. It was then I feared that there was no way I could ever recover as a web content writer.

I hung around my industry for ten more years (including one where I couldn't find a single job FOR AN ENTIRE YEAR) and saw all my fears come true.

So, let's just say I hate Yahoo. Nowhere near as much as Google, which killed the entire industry I wrote for, but still I hate Yahoo. This was a company that offered as prizes for writers swag from their company store. As if. I "won" the Yahoo! Writers' Guide. Guess how many times I used it?

That's right -- never. And no one at Yahoo noticed.

I was hoping from this book to see how Yahoo screwed itself up. I was also wondering if it would mention Yahoo buying Associated Content and turning it into Yahoo! Voices, but found out that AC was one of 50 companies bought in a five year span. There was no listing of all of the companies ... and no bibliography or, most of the time, any source cited.

This is basically just the half-assed autobiography of a salesman in Yahoo who later went on to be a Florida Senator. He was about the 30th employee hired. He only stayed for a few chapters in the book. He does not write well. He repeats, repeats and repeats again. Whenever he usues an analogy, he can't just use one. He has to use at least three. Despite the large print and lots of white space, this book could've been half it's length if the dross was removed.

Two years after he left Yahoo, someone tried to extort him for $4 million.

I rooted for the extortionist.
Profile Image for Peter Calano.
12 reviews6 followers
January 5, 2021
The book was painful to get through. Ring’s career is quite interesting, but becomes unbearable to listen to when told through his elitist, conceited lens, coupled with the constant barraging of irrelevant hyperboles. Cool topic. Brutal writing. Ring is also wildly repetitive and hilariously unfunny.
Profile Image for Tom Hespos.
13 reviews2 followers
June 5, 2018
Add a star if you were a participant in the first dot com boom and look back on that period fondly.

Ring was my first Yahoo! sales rep and for that, I will tease him relentlessly until one of us dies. The first several chapters of this book cover a period we lived through with similar perspectives, and that bit of nostalgia riding through his narrative of the go-go 90s was terrific fun.

In my opinion, the writing gets really compelling when Ring describes one of the downsides of all that dot com money coming his way - a dangerous extortionist who threatens Ring and his family. Although he and I are old business associates, I confess that I didn't know about this chapter in his life, and it's absolutely chilling reading his account of it.

Yes, there is a good deal of navel-gazing when it comes to Yahoo! and what it could have (or should have) been in the end. I happen to be a huge fan of Yahoo! and of the folks that comprised Ring's team there, so for me, this was an interesting exercise comparing my own thoughts on its rise and fall with Ring's. In the end, we weren't very far apart with our reasoning.

But the appeal of this book is not in the "woulda, coulda" or the validation of one's thoughts about the Internet darling and what went wrong. The appeal for me was in its earlier chapters as Ring weaves a tale of a series of happy accidents combined with determination and foresight that leads to his working for Yahoo! in the first place. Those types of things happened to many of us during the mid-90s, and I like to look back on those days through the lens of my belief that, at a certain time in American history, you created your own business destiny. That destiny was made more inevitable by orbiting the companies you admired in an industry that didn't yet have any experts, thus creating your own opportunity. Ring shows how he did this with Yahoo! and, in doing so, also reveals quite a bit about what made Yahoo! special.

Although I never worked at Yahoo!, I did do quite a bit of business with them over the years, with a cavalcade of salespeople that started with Jeremy Ring. Some of my best friends in this digital ad industry are former Yahoos, and I think he did an admirable job of showing exactly why. The death of the culture there was certainly something to lament, since it was unparalleled in the industry and hasn't been seen since. Ring helps us understand that there are people out there who still bleed purple and yellow. And there's a number of great reasons for that.
Profile Image for Erik Surewaard.
186 reviews7 followers
May 24, 2018
This person shows what is clearly wrong with society. Somebody who has no real specialist education, was non-performant in his jobs (he admitted himself he did nothing and only played e.g. minecraft), got fired, had four jobs in two years, lived in a “cupboard” in a small appartment in NY, and by massive luck was hired by Yahoo two months before the IPO. And this with 50k stock options.

He got hired by Yahoo because he worked several months by an advertising company (IMS) that worked for Yahoo. That job at IMS he sought not himself by the way... Somebody else introduced him there when he was without a job. At IMS, he was involved in selling banner ads. So nothing special in my opinion.

So by a massive lot of luck, he ended up in the right place at the right time. At any other time he would never ever ended up as rich as he became from his stock options.

So... this author complains about bums in this book. He also goes off topic many times, going so far as dedicating several chapters on a private extortion case.

When discussing Yahoo, it became clear he stopped working for Yahoo just after the IT bubble burst. So much for an insider account until today... I even read that he became CEO of a small company that did not perform well. He is further very determined in downtalking the efforts of one of the Yahoo CEO Semmel. As if Semmel was responsible for major mega-mistakes of not investing in Google, Facebook, ... Like as if Yahoo would have bought the Google patent at the time that it would have automattically have become a business of 670 billion USD. An amount by the way, that the author repeats through the complete book. This book shows nothing on what really went right/wrong at Yahoo in the years after the 2000’s. Maybe the author missed the investment that was successfully made in Alibaba??

As mentioned, this book stands for everything that is wrong in todays society:a growing disbalance between rich and poor. Don’t forget that the millions this author earnt in stock options came also from pension funds and the main street investor. And believe me... I am not jealous on his riches. He just got lucky.

In the end, the book is nothing special. A lot of blabla on himself, whereby the ‘story’ of Yahoo is more one of complaining about and ex-CEO called Semmel. Not worth more than two stars in my opinion. This since this book allows you to see the ego someone can get through luck.
Profile Image for Peter Myers.
29 reviews1 follower
January 20, 2020
I enjoyed this book. Well written from a different perspective. Certainly shows how the nonsense of the dot com boom was fuelled more by good luck than anything else, and showed just how impactful some bad decisions can be
Profile Image for Cory.
15 reviews2 followers
March 10, 2018
I really enjoyed this book. It gives great insight to the workings of s major company. The only thing I didn't like was that it turned into a bit of a CEO bashing towards the end.
Profile Image for Russel Lazega.
Author 20 books121 followers
March 16, 2018
A must read for business enthusiasts. An intriguing story of how the right company can go so wrong and crumble.
Profile Image for David Oxley.
7 reviews
April 29, 2018
4 stars for content, but the author's repetitive writing style and the book's haphazard organization bring it down to 3 stars. Still worth reading.
Profile Image for Doro.
216 reviews2 followers
July 28, 2018
A recollection of interesting times but in parts hard to read. Too many repetitions. An editor would have been a good idea.
492 reviews2 followers
December 11, 2019
This is a decent book. However, even though it may have been fact-checked, it reads as though it was tinged by personal “bias” FWIW.
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