Companies change hands all the time, and business history is full of expensive acquisitions that went nowhere. But the opposite kind of deal is much more fun to look back on. Sometimes a founder sold because the company was difficult to run, while other times a larger corporation simply spotted an opportunity before everyone else did. A few of these prices seemed perfectly reasonable at the time. What happened afterward made them look very different.
1. McDonald’s
Richard and Maurice McDonald had already created the fast, tightly organized restaurant system that would define the chain when Ray Kroc bought them out in 1961. The deal cost Kroc $2.7 million, a substantial amount at the time but tiny compared with what the business eventually became. He pushed franchising much harder than the brothers had wanted, taking McDonald’s from a successful restaurant concept into a global operation with tens of thousands of locations. The brothers got their money, but they gave up the name just before it became one of the most valuable restaurant brands on Earth.
2. Kentucky Fried Chicken
Harland Sanders had spent years traveling around the United States signing up restaurants to serve his fried chicken when the business finally became too large for him to manage comfortably. In 1964, a group led by John Y. Brown Jr. and Jack Massey bought Kentucky Fried Chicken for about $2 million. Sanders stayed involved as a spokesman, appearing in advertisements and visiting restaurants while the new owners handled the expansion. The chain already had hundreds of franchises, but what followed was on another level, with KFC eventually spreading across more than 100 countries.
3. Coca-Cola
Coca-Cola did not begin as a giant beverage corporation. In the late 1880s, it was a fountain drink being sold in Atlanta pharmacies when businessman Asa Candler started acquiring the rights from the people connected to its creation. By 1891, his total investment in securing control was roughly $2,300. Candler then built a company around the drink, pushed advertising aggressively, and expanded distribution across the country. A recipe and trademark that had changed hands for a few thousand dollars eventually became the center of one of the world’s largest beverage businesses.
4. Victoria’s Secret
Roy Raymond started Victoria’s Secret because he thought buying lingerie in traditional department stores was awkward for men. The idea worked well enough to produce several stores and a catalog, but financial problems followed. In 1982, Raymond sold the company to Leslie Wexner for about $1 million. Wexner changed the emphasis, marketed the brand much more directly to women, and expanded it through malls across the United States. Within a little more than a decade, Victoria’s Secret was producing well over $1 billion in annual sales.
5. Starbucks
The Starbucks Howard Schultz bought in 1987 was not yet the Starbucks most people picture today. It was a small Seattle company with six stores, a roasting facility, and a business still centered largely on selling coffee beans. Schultz raised roughly $3.8 million to acquire it and merged it with his own coffee-bar operation. From there, Starbucks leaned into the Italian-inspired café model Schultz had been trying to build. The company that began with a handful of Seattle locations eventually grew into a chain with tens of thousands of stores around the world.
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6. Pixar
Pixar was not originally an animation studio filled with guaranteed blockbuster movies. It began as a computer graphics division inside Lucasfilm, and Steve Jobs acquired it in 1986 in a deal that involved about $5 million paid to Lucasfilm and another $5 million invested in the new company. For years, Pixar sold hardware and worked on graphics technology while trying to find a sustainable business. Then Toy Story arrived in 1995. Disney eventually bought Pixar in 2006 for about $7.4 billion.
7. Hotmail
Microsoft paid around $400 million for Hotmail in 1997, only a year and a half after the webmail service had launched. That was serious money for an internet company at the time, but Hotmail’s growth made the purchase look much smaller afterward. The service became one of the most widely used email platforms in the world and later evolved into part of Microsoft’s Outlook ecosystem.
8. PayPal
By 2002, PayPal had become so important to eBay users that buying the company started to make more sense than competing with it. eBay paid about $1.5 billion in stock for the payment service and kept it inside the company for more than a decade. PayPal continued expanding beyond online auctions, handling payments for merchants and consumers all over the internet. When eBay spun PayPal back out as an independent public company in 2015, the newly separated business was valued at roughly $50 billion.
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9. Android
When Google bought Android Inc. in 2005, there was no Android phone, no Play Store, and no reason for the average person to know the name. The price was never officially disclosed, though estimates have commonly placed it around $50 million. Andy Rubin and his small team were developing software for mobile devices at a moment when the future of smartphones was still unsettled. A few years later, Android began appearing on commercial phones, and it eventually became the operating system used by most smartphones worldwide.
10. Booking.com
Priceline bought the Dutch company Booking B.V. in 2005 for about $133 million. It was already growing quickly, but the deal barely resembles the scale of the business that emerged from it. Booking.com became the most important part of Priceline’s international expansion and eventually so central to the company that the entire corporate group was renamed Booking Holdings. The platform now handles hundreds of billions of dollars in travel reservations each year.
11. YouTube
Google’s decision to spend $1.65 billion on YouTube in 2006 did not look cheap at the time. The video site was barely a year old, had enormous bandwidth costs, and was attracting plenty of questions about copyrighted material. Google kept it separate enough to preserve the service people liked while gradually building a much larger advertising and creator economy around it. By 2025, YouTube was generating more than $60 billion a year from advertising and subscriptions combined.
12. Instagram
Facebook agreed to buy Instagram for roughly $1 billion in 2012, when the app had only been around for about 18 months. It had a small team, no mature advertising business, and nowhere near Facebook’s reach. Still, its rapid growth made Mark Zuckerberg willing to pay what many observers considered an extravagant price. Instagram later passed 2 billion monthly active users and became one of Meta’s most commercially important products. That billion-dollar check stopped looking extravagant a long time ago.
13. Converse
Converse had been making Chuck Taylor sneakers for generations, but history alone was not keeping the company financially healthy. It filed for bankruptcy in 2001, and Nike acquired it two years later for roughly $305 million. Nike kept Converse as a separate brand while giving it access to much larger distribution, marketing, and international operations. Within a decade, Converse was bringing in more than $1 billion a year.
14. Vans
Vans had already survived bankruptcy, ownership changes, and decades of shifting fashion when VF Corporation bought it for about $396 million in 2004. The brand was strongly associated with skateboarding, but VF saw room to make it much bigger without stripping away that identity. Vans expanded internationally, added more apparel, and became increasingly visible outside skate culture. Less than a decade after the deal, annual revenue had climbed to around $1.5 billion.
15. Marvel Entertainment
Disney spent about $4 billion to acquire Marvel Entertainment in 2009. That was hardly pocket change, but it gave Disney control of a character library containing Iron Man, Thor, Captain America, the Avengers, and thousands of others just as Marvel’s movie strategy was beginning to work. The Marvel Cinematic Universe soon became a steady source of billion-dollar films, streaming shows, merchandise, attractions, and licensing revenue. Looking back, Disney effectively bought one of the most productive entertainment libraries in modern Hollywood before its biggest years had even begun.
16. Lucasfilm
George Lucas sold Lucasfilm to Disney for approximately $4.05 billion in 2012, handing over Star Wars, Indiana Jones, Industrial Light & Magic, and several other valuable pieces of the company. Three years later, Star Wars: The Force Awakens alone made more than $2 billion at the worldwide box office. Disney followed it with additional films, television series, merchandise, games, and enormous Star Wars lands at its theme parks. The acquisition was expensive, but the amount of entertainment Disney received for the price made it look increasingly reasonable with every new project.
In the mood for more?
Check out 16 Companies That Were Laughed at Before Becoming Worth Billions, or take a look at 14 Product Slogans People Still Recognize Decades Later. If you want to see more unusual business history, you can check out 16 Iconic American Companies That Were Started With Less Than $1,000.
