The Biggest Missed Opportunities in Business History
Blockbuster passed on Netflix, Yahoo on Google, and Apple’s third founder sold his 10% for $800.
Last updated November 6, 2026
Every business story has a road not taken. Most are forgotten. A few become legends, because the thing someone turned down went on to be worth billions.
These are the most famous missed chances in our archive. Each one looked reasonable at the time, and that is what makes them worth studying. Every entry links to the full story, where the sources are listed.
1. Blockbuster passes on Netflix for $50 million (2000)
$50MNetflix’s asking price
In early 2000 Reed Hastings and Marc Randolph flew to Dallas and offered to sell Netflix to Blockbuster for $50 million. Blockbuster’s chief executive, John Antioco, declined. Netflix was small and, by Hastings’s account, on course to lose $57 million that year. Blockbuster filed for bankruptcy in 2010. Netflix reported revenue of $45.18 billion in 2025.
Read the full story: Blockbuster Could Have Bought Netflix for $50 Million
2. Yahoo turns down Google for $1 million (1998)
$1MReported asking price
In 1998 Larry Page and Sergey Brin reportedly offered their search technology to Yahoo for about $1 million, and Yahoo said no. In 1999 Excite passed too, even at $750,000, by investor Vinod Khosla’s account. Yahoo discussed buying Google again in 2002 but agreed no price. Its core business sold to Verizon for $4.48 billion in 2017. Google’s parent, Alphabet, took in $402.8 billion in 2025.
Read the full story: Yahoo Could Have Bought Google for $1 Million
3. Ronald Wayne sells 10% of Apple for $800 (1976)
$800Paid for his 10%
Ronald Wayne signed Apple’s founding partnership on April 1, 1976, with a 10% share. Eleven days later, worried that he would be personally liable for the young company’s debts, he withdrew for $800, and later accepted $1,500 more to give up any claims. His copy of the founding contract sold at auction for $1,594,500 in 2011. Apple’s revenue in fiscal 2025 was $416 billion.
Read the full story: The Apple Cofounder Who Sold His 10% for $800
4. Kodak invents the digital camera and holds back (1975)
1975First digital camera
Kodak engineer Steven Sasson built the first digital camera in 1975. Kodak patented it, kept investing in digital technology and sold consumer digital cameras from 1995, but it treated digital as a sideline to its far more profitable film business. When photography went digital and then moved to phones, Kodak filed for bankruptcy in 2012.
Read the full story: Kodak Invented the Digital Camera, Then Went Bankrupt
5. IBM lets Microsoft keep the rights to DOS (1981)
$75,000What Microsoft paid for DOS
IBM needed an operating system for its first personal computer. Microsoft bought one from Seattle Computer Products for a total of $75,000 and licensed it to IBM on non-exclusive terms. That left Microsoft free to sell MS-DOS to every company that built an IBM-compatible clone. Microsoft reported revenue of $331.8 billion for fiscal 2026.
6. Warren Buffett buys a dying textile mill over 12.5 cents (1964)
$200BBuffett’s own estimate of the cost
In 1964 Berkshire Hathaway, a struggling textile maker, offered to buy back Warren Buffett’s shares at $11.375, an eighth of a point below the $11.50 he says had been agreed. Irritated, he bought control of the company instead. In 2010 he told CNBC the decision had cost about $200 billion, compared with putting the same money straight into insurance.
Read the full story: Warren Buffett's $200 Billion Berkshire Hathaway Mistake
7. Two pizzas for 10,000 bitcoin (2010)
$1.26BValue at the 2025 peak
On May 22, 2010, programmer Laszlo Hanyecz paid 10,000 bitcoin, then worth about $41, for two Papa John’s pizzas. At bitcoin’s October 2025 peak of about $126,200, the same coins would have been worth about $1.26 billion. Hanyecz has never sounded sorry: the purchase helped show that bitcoin could be spent as money.
8. Rexall gives up the stores that became Trader Joe’s
6Stores Rexall wanted closed
In 1958 the drugstore chain Rexall asked Joe Coulombe to test convenience stores called Pronto Markets. After he had six running, Rexall changed direction and told him to liquidate them. He borrowed money and bought them himself. In 1967 he opened the first Trader Joe’s. Today there are 661.
Read the full story: Trader Joe's Began With a Store That Lost to 7-Eleven
9. MySpace passes on Facebook at $75 million (2005)
$75MZuckerberg’s asking price
In February 2005 MySpace’s chief executive, Chris DeWolfe, talked with Mark Zuckerberg about buying Facebook, then a site for college students, and turned down the $75 million asking price, according to Wikipedia. Later that year News Corp bought MySpace’s owner for about $580 million. Facebook overtook MySpace in 2008, and in 2011 News Corp sold MySpace for about $35 million.
Read the full story: News Corp Paid $580 Million for MySpace and Sold It for $35 Million
10. Groupon turns down $6 billion from Google (2010)
$6BGoogle’s reported offer
In December 2010 Groupon walked away from a Google offer reported at up to $6 billion. Its 2011 IPO valued it at about $12.7 billion, twice the offer, but by February 2013 the shares were 77% below the IPO price and founder Andrew Mason had been fired. At the end of October 2026 the whole company was worth about $634 million.
Read the full story: Groupon Said No to $6 Billion From Google, Then Fell 77%
11. Monopoly’s inventor sells her patent for $500 (1935)
$500No royalties
Lizzie Magie patented The Landlord’s Game, the ancestor of Monopoly, in 1904. In 1935 Parker Brothers bought Monopoly from Charles Darrow, who kept royalties and became a millionaire, and then paid Magie $500 for her patent. By 1974 Parker Brothers had sold 80 million Monopoly sets.
Why they were missed
Hindsight makes these decisions look foolish, but most were sensible with what people knew at the time: a small start-up losing money, a risky partnership, a product that threatened a profitable business. The common thread is how hard it is to put a value on something new.
For the other side of the story, see what famous companies sold for and the companies that almost went bankrupt.
Every figure on this page comes from the 11 stories linked above, where the sources are listed. Read how we check them in our editorial standards.