Some of the most valuable companies in the world owe their dominance not just to internal innovation, but to a handful of strategic acquisitions that turned modest investments into multi-billion-dollar pillars of modern tech and media empires. A recent infographic shared on Reddit highlights 10 of the greatest acquisitions ever—ranked by estimated return on investment. The graphic reflects not just the raw dollar return, but the transformative impact these deals had on their parent companies.
Here’s a closer look at the companies, purchase prices, and the estimated market cap value they’ve added.
| Company Acquired | Acquirer | Purchase Price | Estimated Return | ROI Multiple |
|---|---|---|---|---|
| DoubleClick | $3.1B | $182B | ~59x | |
| $1.0B | $174.5B | ~175x | ||
| YouTube | $1.65B | $160B | ~97x | |
| NeXT | Apple | $429M | $126B | ~294x |
| Android (via Android Inc.) | $50M | $112B | ~2,240x | |
| Booking.com | Priceline | $135M | $46.6B | ~345x |
| PayPal | eBay | $1.5B | $45.6B | ~30x |
| Google Maps (via Where 2 Technologies) | $70M | $27.9B | ~399x | |
| ESPN | Disney | $188M | $26B | ~138x |
| Marvel | Disney | $4.2B | $13.3B | ~3.2x |
Not Just Numbers: Transformational Impact
1. Android – Google’s Ultimate Buy
Acquired in 2005 for just $50 million, Android is now the world’s most widely used operating system, powering billions of devices. Without it, Google’s dominance in mobile—ads, apps, maps, YouTube—might never have taken off. The estimated $112B return might even undersell its actual strategic value.
2. NeXT – The Deal That Saved Apple
Apple’s $429M acquisition of NeXT in 1997 wasn’t just about the software—it was about bringing Steve Jobs back. The NeXTSTEP operating system became the foundation of macOS, iOS, and everything Apple’s built since. Many commenters rightly argue the return here—listed as $126B—is “wildly undervalued.” Without it, there likely would be no iPhone.
3. Instagram – From Mockery to Masterstroke
Facebook’s acquisition of Instagram in 2012 for just $1B was heavily mocked at the time. Fast forward, and Instagram is now one of Meta’s most valuable platforms, driving ad revenue, creator engagement, and social commerce. Its return of $174.5B puts it second on the list, with an astonishing ~175x ROI.
4. YouTube – The $1.65B That Rewrote the Internet
Google’s 2006 acquisition of YouTube was seen as a gamble. Today, YouTube generates billions in ad revenue annually and is a cornerstone of Google’s ecosystem. With streaming, Shorts, and premium content growing, its $160B estimated return is still conservative to some analysts.
5. DoubleClick – The Backbone of Google’s Ad Empire
Bought in 2008 for $3.1B, DoubleClick evolved into Google’s ad serving infrastructure (Campaign Manager 360). While many casual users may not recognize it, this backend powers Google’s programmatic advertising—arguably the most profitable part of Alphabet’s business. Estimated return? $182B.
Insights from the Reddit Thread
- Undervalued Impact: Redditors pointed out that NeXT, Android, and even DoubleClick are possibly undervalued. These weren’t just products—they reshaped entire business models.
- Missed Opportunities: A few mentions lamented the deals that could have been—Blockbuster passing on Netflix, Yahoo skipping on Google.
- Cultural Shifts: Marvel and ESPN might have lower multiples, but they transformed Disney’s brand from a family-first entertainment company into a cultural juggernaut.
What Didn’t Make the List?
Critics in the thread noted several glaring omissions:
- Microsoft’s LinkedIn acquisition ($26B) is now worth over $100B.
- Microsoft’s purchase of Mojang (Minecraft) for $2.5B is now a billion-dollar IP across media and education.
- Activision-Blizzard, acquired by Microsoft for $75B in 2023, was too recent to be included but may someday join this elite group.
And of course, many argued the greatest acquisition of all time was the Louisiana Purchase for $15M—a different type of empire building.
Internet Acquisition History: A Look Back At Tumblr
Tumblr’s journey through the market has been a roller coaster of valuations since its inception in 2007. It started as a platform for short-form blogs and quickly grew into a popular social media site. Its simple interface and unique culture attracted millions of users, catapulting Tumblr to the top as an online trendsetter. When Yahoo bought Tumblr in 2013 for $1.1 billion, the acquisition continued to the business lexicon as a mark of success in the tech industry.
The excitement was short-lived, however. The platform saw a significant decrease in value over the years. In a startling turn of events, the valuation of Tumblr took a steep dive. After a series of missed goals and strategic missteps, Yahoo marked down the value of Tumblr, citing it failed to meet sales targets. Later, the blogging service was sold to Verizon and eventually to Automattic, the parent company of WordPress, at a fraction of its acquisition price by Yahoo.
Key Takeaways
- Yahoo’s purchase of Tumblr in 2013 for $1.1 billion highlighted its peak valuation.
- Tumblr’s value significantly declined due to not meeting sales and performance expectations.
- The platform changed hands several times, selling most recently for a mere fraction of its peak price.
Corporate History and Acquisitions
The evolution of Tumblr and various ownership changes mark the corporate journey of this social platform. Key acquisitions and deals illustrate how the value and control of Tumblr shifted over time.
Tumblr’s Evolution and Ownership
Tumblr began as a vibrant social media platform founded by David Karp in 2007. Its rise in popularity caught the attention of Yahoo, which acquired Tumblr for $1.1 billion in 2013. The CEO of Yahoo, Marissa Mayer, promised not to screw it up. Despite the optimistic outlook, Tumblr faced challenges. Yahoo was unable to meet the sales goals it had set for Tumblr. This led to a write-down of Tumblr’s value by Yahoo in 2016.
Verizon acquired Yahoo in 2017, and with it, Tumblr became part of Verizon’s media group. This group was first named Oath and later rebranded as Verizon Media. The changes in Tumblr’s ownership did not stop there. The platform once valued at over a billion dollars was sold to Automattic Inc, the parent company of WordPress, for a much smaller sum. Matt Mullenweg, CEO of Automattic, committed to preserving the community that defines Tumblr.
Major Acquisitions and Deals
| Year | Event | Details |
|---|---|---|
| 2013 | Tumblr acquired by Yahoo | Deal valued at $1.1 billion |
| 2016 | Yahoo writes down Tumblr’s value | $230 million write-down announced |
| 2017 | Verizon acquires Yahoo (includes Tumblr) | Yahoo becomes part of Oath, later Verizon Media |
| 2019 | Tumblr sold to Automattic Inc | Sold for a reported $3 million |
The notable sale to Automattic in 2019 marked a significant decrease in Tumblr’s valuation. The acquisition by Automattic brought Tumblr under the same umbrella as WordPress, indicating a potential synergy for the blogging platforms. Despite fluctuations in its value, Tumblr remained a unique platform with a loyal user base.
