6 Business Deals So Bad They Make Bitcoin Seem Like A Sure Thing

6 Western Union Turns Down the Telephone

Imagine you’re the mighty communication mogul known as Western Union. The year is 1876, and you’re sitting pretty on a network of over 7,000 telegraph offices, running almost 20 million messages a year. Suddenly, some jamoke asks you for the astronomical sum of $100,000 in return for the patents on an invention that allows you to talk with people over long distances — very poorly might I add.

You tell that little pipsqueak by the name of Alexander Graham Bell to get the fuck out of your office, and to take his dumb little “telephone” with him. The era of dots and dashes will live forever! Well, that or it will go down as one of the worst business misses of all time, a communications giant passing on the chance to own the rights to the telephone. Win some, lose some!

5 Yahoo! Passes on Google

Speaking of businesses so ubiquitous and world-changing that they’re forever considered a verb, let’s take a look at the one probably storing all of our blood types in an off-shore server: Google. Among the biggest and most important companies on Earth, and one that any intelligent businessperson would leap at the opportunity to acquire, if doing so wasn’t equivalent to a garter snake trying to swallow a sperm whale. Acquiring Google in the year 2023 is basically unthinkable. It would be like someone pitching a plan to annex the entirety of the modern United States. 

When it was no more than an electronic babe with dreams of Skynet sparkling in its eyes, however? It was not only possible, but explicitly offered. Creators Larry Page and Sergey Brin felt their little Google thing was distracting from their studies, and wanted to unload it for one million dollars. Yahoo! passed, partly because it worked… too well? They thought effective search results would pull users away from their website before they had a chance to bombard them with ads, and so, they stuck with their own search engine. They now exist mostly to provide fake email addresses used for sketchy website sign-ups.

4 Blockbuster Shows No Interest in Netflix

Blockbuster Video, once an essential part of most family’s weekly entertainment, now exists mostly in the form of iconic skeletons scattered across the country. If you see their trademark ticket stub architecture today, it’s more than likely half-disguised behind the logo of a Thai restaurant. You don’t exactly need red yarn and a bulletin board to trace the culprit behind their passing either.

Once a company called Netflix debuted, capable of spraying DVDs like buckshot to anyone with a mailbox, why would anyone go to their blue-and-yellow brick-and-mortar counterpart? After all, what can you do when faced with a juggernaut like Netflix? Well, for one, you could buy their company when they try to sell it to you for $50 million. Instead, Blockbuster brushed them off for months, and swallowed laughter at the quoted number. Now, I assume they’re sitting on a couple boxes of stolen Buncha Crunch under a bridge somewhere.

3 Yahoo! Passes on Google, Part Two

Yahoo! had to be kicking itself after passing on the chance to acquire what would become one of the world’s biggest businesses for a comparative pittance. You’d think that, most days after telling Google no, their executives stood sadly staring out of office windows, palms on glass, lamenting what might have been. It’s far from a guarantee in life that you’ll ever get a second chance.

They did, though. Only four years later, Larry Page and Sergey Brin were back in the Yahoo! boardroom, with a sequel to the botched sale on the table. Yahoo! pushed forward $3 billion as an offer, already a $2,999,000,000 testament to terrible value recognition. Brin and Page issued a counter-offer of $5 billion, and Yahoo responded by once again, figuratively slamming their own dick in a car door and turning down Google again.

2 NBC and CBS Fumble Monday Night Football

There might not be a more surefire money printer in existence than the National Football League. You have to already be venomously rich in order to actually get in on it, but if you can, you should shove as much money in as they’ll allow (with the exception of building a shiny new stadium). Dan Snyder bought an NFL team for $800 million, curbstomped it for 23 years straight, and still sold the bloody remnants for over a $5 billion profit.

Especially if you’re a TV network, if the NFL dangles exclusive rights in front of you, you dance like the little piggy they want you to be. A lesson that was learned the hard way by both CBS and NBC in 1970, when they were offered the modern ratings behemoth that is Monday Night Football. They turned it down, banking on the continued popularity of The Doris Day Show and Laugh-In, respectively. ABC, possessing a skull not filled with shit, instead saw the potential. They not only bought it, but invested heavily into production value, creating a ratings monster out of a mediocre time slot.

1 God Dammit, Yahoo!

In 2008, as Yahoo! sat in the stink of their own self-shat bed, they were made a gargantuan offer by Microsoft, which was looking to acquire them. Microsoft, for three months, wheeled progressively larger wheelbarrows of money to Yahoo!’s front door, and each time, they were sent packing. 

When co-founder Jerry Yang turned up his nose at an offer of roughly $47.5 billion, they’d had enough. Microsoft CEO Steve Ballmer stated, “After careful consideration, we believe the economics demanded by Yahoo! do not make sense for us,” which is CEO-speak for “These guys’ heads are stuck so far up their own ass that we feel there is no hope of retrieving them.” Perhaps it was a matter of pride. In which case, Yahoo! got to proudly pilot a sinking ship toward its eventual resting place of being acquired in 2016 by Verizon for $4.83 billion, or one-tenth of the price they’d been offered eight years earlier.

Eli Yudin is a stand-up comedian in Brooklyn. You can follow him on Twitter and Instagram at @eliyudin and listen to his podcast, What A Time to Be Alive, about the five weirdest news stories of the week, on Apple Podcasts, Spotify or wherever else you get your podcasts.