Getting a leg up in the tech industry can be a highly challenging task. Most big companies invest millions of dollars in R&D and innovation, but also have to keep an eye out on the emerging businesses and startups that can give them an advantage over bitter rivals. This has been the case since time immemorial, but only recently has there been a strong spotlight on Internet buyouts. The reason: Bright startups with good products are becoming increasingly ubiquitous these days thanks to concepts like crowd-sourcing and crowd-funding. This has resulted in a spike in the number of acquisitions recently. That said, the enterprise space has been largely neglected. 

Even the likes of Google, Yahoo!, Amazon and Microsoft have had to take the acquisition route to one-up the competition. You may know of the bigger acquisitions that have happened recently, the Facebook-Instagram deal, for instance, but some buyouts slip under the radar. Here’s a rundown of the 10 of the most expensive Internet buyouts in the recent past, complete with our pick for the highest spenders.  

Deal – Microsoft acquired Skype in 2011 

Value – $8.5 billion 

When will it come to the phones?

That billion dollar handshake

The story – After pursuing it for months, Redmond, Washington firm Microsoft finally acquired popular VoIP service Skype in October 2011. The deal was finally sealed for a whopping $8.5 billion, after the European Union (EU) gave it its nod – making it one of the priciest buys of that year. 

It clearly isn’t the first time that the now massively popular service changed hands. eBay, the popular online auctions destination, had in fact acquired Skype in September 2005. However, it announced in April 2009 that it plans to spin it off in a 2010 IPO. From there, Silver Lake Partners acquired it in 2009. As it stands today, Skype is a division of Microsoft called Microsoft Skype Division. Skype though popular, often finds itself grappling in hot waters owing to the nature of the service. 

All in all though, Microsoft seems to have done well for itself by making this purchase. 

Deal – Intel acquired McAfee in 2011

Value – $7.68 billion

For better security solutions

For better security solutions

The story – The semiconductor chip maker took in McAfee, a noted name in computer security space, for that sum, after almost a year of announcing that a deal was coming. Intel confirmed that it wanted to offer security to emerging technologies.

Deal : Yahoo! acquired Geocities in 1999

Value – $3.57 billion 


Picked the third-most visited site in the world in 1999

The story – Geocities, for those who remember it, was really popular back in the day  – it was the third-most visited site on the web. A known web hosting service, GeoCities allowed users to pick a “city” in which they would want to place their web pages. These were named after real cities or regions, depending on the content. It got really popular over time, so much so that by 1999 it became the 3rd most visited website in the world. 

That year, Yahoo! took it under its fold, and like many other acquisitions, downed the shutters on it in 2009 – you can still log on to the Japanese version of the service. #justsaying.

Deal – Adobe acquired Macromedia in 2005

Value – $3.4 billion

Adobe gets flashier!

Adobe gets flashier!

The story  – With this deal, the ubiquitous (irrespective of what Apple says) Flash came under Adobe’s wing. The 2005 deal cost Adobe $3.4 billion. Adobe viewed its deal with Macromedia as a way to fulfill consumers' demands for for making audio and video documents, and images compatible with their handheld devices. The company also received access to the popular animated graphics software that has been making a headway to mobile phones. 

Deal – Google acquires DoubleClick in 2008

Value – $3.1 billion 

Google goes shopping

Google goes shopping

The story – After almost a year of announcing its intention of acquiring DoubleClick, Google finally completed the deal in 2008 for $3.1 billion in cash. In fact, roughly a year later, on April 2, 2008, Google said it would cut 300 jobs at DoubleClick, citing organisational redundancies. A few selected employees, it is known, were to be taken into Google, as per position and experience.  

Founded in 1995, DoubleClick was a noted name in online advertising industry; it provides Internet ad serving services.

Deal – Google acquired YouTube in 2006

Value – $1.6 billion


…and they lived happily ever after

The story – Yes, the two seemed like they have been with each other forever, but truth is that Google acquired the now massively popular YouTube, back in 2006. The two have remained inseparable ever since. Google paid big money – a good $1.65 billion – to get YouTube, and at the time of finalising the deal, it was the search giant’s largest acquisition. Psst! It is said that Yahoo! was in the bidding race right till the end! 

YouTube is the birthplace of the success of the starry Gangnam Style and Kolaveri Di, and is the go-to platform for many of us to discover many cool videos – be it a music album or our favourite show. It boasts of a user base that spans the expanse of the globe. Each year, the site puts out mind boggling numbers for stats; for instance, it now boasts of having over a billion unique visitors and a mind-boggling 4 billion hours of video are viewed each month. 

Deal – eBay acquired Paypal in 2002

Value – $1.5 billion

eBay buys PayPal

eBay buys PayPal

The story – eBay, the popular auction website, picked PayPal for that price and said it would discontinue its own eBay Payments service by Billpoint. PayPal's services were used by many of eBay's loyal customers and hence, this deal made sense. Today, PayPal is one of the largest online payment/money transfer services.

Deal – Symantec acquired VeriSign’s security business in 2010

Value – $1.28 billion


Veri sure about security

The story – Noted computer security company Symantec paid that sum to acquire VeriSign's identity and authentication businesses – its Secure Sockets Layer (SSL) Certificate Services, Public Key Infrastructure (PKI) Services, the VeriSign Trust Services and the VeriSign Identity Protection (VIP) Authentication Service. 

Deal – Yahoo! acquired Tumblr in 2013

Value – $1.1 billion

Yahoo! Tumblr

Yahoo! Tumblr

The story – A quick recap: A mature Yahoo! wanted to be “cool again”, at least that’s what CFO Ken Goldman told the press/whoever (not a speech). Tumblr, one of the coolest places to be in, became the obvious pick for the company, and the deal followed soon after. It wasn’t all smooth though on the user side. Some even started a petition to prevent the sale from happening, while it left some others thinking about switching over to other platform. 

The deal has happened and CEO David Karp has promised to not “screw it up”. We’ll wait and watch to see how this one’s faring. 

Deal –  Amazon acquired Zappos in 2009

Value –  $850 million

Creating a mark!

Creating a mark!

The story – and, two popular online retail entities, came together in a deal amounting to $850 million, in 2009. 

Zappos, like Amazon, is a highly customer-friendly unit with a great culture – just the kind of thing the otherwise self-sufficient Amazon would have been looking for. 

As part of the deal, Amazon was to purchase all of Zappos' outstanding shares, options and warrants from Zappos for 10 million shares of its common stock. Also, it was to provide $40 million in cash and restricted stock, specifically for the employees at Zappos. The service, though, has seen instances of legal troubles in the past owing to the content found on it.  

Deal – Facebook acquires Instagram in 2012

Value – $715.3 million

For a better photos experience

For a better photos experience

The story – This one seemed to many a marriage made in the proverbial “heaven”. Social networking giant Facebook took budding photo-sharing app Instagram under its wide, wide fold last year. Many took to it as an obvious progression by the social networking giant, since so many users share so many pictures each day on the platform.  

When the parties had first agreed to it, the deal was valued at $1 billion. However, around the time of the deal being finalised, Facebook's stock price dropped. Finally, when the deal was closed, its worth was pegged at about $715.3 million – $300 million of it in cash and the rest in stock. 

Many ardent users of Instagram did not take to the big change nicely. 

Months after the deal came through, Instagram made changes to its Terms of Service to the effect that it gained rights to sell users' photos to third parties without any notification or compensation whatsoever, starting January 16, 2013. Needless to add, the news created quite a noise among users, celebrities, privacy advocates. Instagram was eventually forced to rollback the changes. 

Top spenders

Yahoo! wins this one hands down. If you could look at the purchases Yahoo’s made in the years leading to this day, you would agree with us. GeoCities marks the earliest Yahoo! acquisition and Tumblr’s its most recent purchase, and it is said that the company is also bidding for, the international television content website owned by Fox, Disney and Comcast. In the years in between, Yahoo! put the likes of, Flickr, Right Media, among others, in its shopping basket too. 

Who knows? Even as you’re reading this, some new deal may be taking shape, getting ready to change the way you and I have been using some product and service. 

Main image and cover image credit: Getty Images

Tags: , , , , , , , , , , ,