Travel News

Mark Cuban Sat in a Southwest Middle Seat – Right After Becoming a Billionaire

Written by Charlie

Right after selling his company for $5.7 billion, Mark Cuban took a flight on Southwest and sat in the MIDDLE SEAT!

I saw this story a while ago and was just reminded of it recently. Being a fan of basketball, Shark Tank, and travel, I wanted to highlight it as a pretty interesting human interest story!

Mark Cuban Became a Billionaire – And Then Flew in a Middle Seat

Depending on your interest – whether it be tech, basketball, Shark Tank, or more – you probably know of Mark Cuban in one way or another. He and his co-founder started and then sold all the way back in 1999. They started it together in 1995 and sold it Yahoo just 4 years later for a whopping $5.7 billion. That acquisition by Yahoo has been called one of the worst in the internet age as they eventually shuttered the audio streaming service.

But, for Mark Cuban, his billions were made! With that, he bought the Dallas Mavericks and something that was his “all-time goal” and that was his own private jet. He purchased the Gulfstream V online for $40 million. According to the Guinness Book of World Records, that is the largest single transaction made on e-commerce. Imagine if he bought that with a credit card that earned some serious points. 🙂

That purchase was in 1999 and the reason he had always wanted to do that, in spite of being frugal in many other areas of life, was because time was money and he valued that time that a private jet would give him. The next year, he bought a Boeing 757 for the Mavericks to fly in (and have since acquired a Boeing 767 as well) and they have even flown in the chartered Crystal AirCruise 777 that has some amazing interiors!

But, before those aircraft purchases, Mark Cuban wanted to celebrate selling his company for $5.7 billion and went to Las Vegas. He bought a ticket on Southwest and ended up in the middle seat – facing backwards (Southwest used to have some rows facing forward-facing rows).

I love this kind of thing! Good for Mark still sticking by his roots even as he went to celebrate becoming a billionaire. His motto had been to “live like a student” and he said that flight was “perfect!”

And There is Another Story!

Another tech acquisition was WhatsApp to Facebook for $19 billion years ago. While you may know that, what you may not know is that founder Jan Khoum was a Flyertalk member. Check out this post here – he ended the post with this: “…and so one of the biggest deals in tech history had to be scheduled around my M&M award ticket

Bottom Line

If you wind up in a middle seat on Southwest, now you can remember that billionaire Mark Cuban did the same exact thing – even though he had enough money to simply buy the aircraft he was flying on! 🙂

Featured image courtesy of Southwest – remember those seats? 🙂

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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.

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