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Mark Cuban talking to Shannon Sharpe Club Shay Shay/YouTube

‘What a deal’: Mark Cuban once drunkenly purchased a $125K airline package after earning his first few million — was he on to something?

Many of us make impulsive financial decisions from time to time, but most people don’t spend six figures while under the influence.

When Mark Cuban sold his software startup MicroSolutions to CompuServe at 32 years old for $6 million in the early 1990s, he brought his friends together for a night of revelry, Cuban told Shannon Sharpe on the “Club Shay Shay” podcast.

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It was Cuban’s first big deal, and he was a newly minted millionaire. So one of Cuban’s friends asked him what he was going to do with all his money —that’s when the wheels started to turn in Cuban’s head.

“I don’t care about cars or houses, but boy, you know, I fly a lot for work,” Cuban told Sharpe.

Cuban drunk dialed American Airlines to inquire about a lifetime flight pass from the biggest carrier in the country.

“Initially, it was $125,000 and then I upgraded it. I forget how much I paid, but it gave me almost unlimited miles for me and somebody else for the rest of my life,” Cuban told Sharpe. “What a deal, right?”

Adjusted for inflation, that now works out to around $300,000, a price that was based on the purchaser’s age when buying the lifetime pass.

While American Airlines no longer offers a lifetime pass and recently ended its flat rate for business travelers, some airlines still offer unlimited, long-term packages that can be a good investment for the right flier.

How do airline packages work?

Even though you can’t buy a lifetime pass from American Airlines anymore, sober or not, carriers still offer packages for frequent travelers.

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Frontier Airlines has a GoWild! All-You-Can-Fly-Pass which covers all domestic and international flights. The carrier travels throughout the U.S., Mexico, Central America and Caribbean.

But there’s a catch. The non-transferrable pass only lets customers book domestic flights one day prior to takeoff and only 10 days before departure for international flights. There are also extensive blackout dates when you can’t use the pass during busy holiday travel periods.

And you still have to pay for bags, seat choice, taxes and fees. Frontier’s pass costs $149 per month, with options of $399 per year for just fall and winter travel, or a $599 annual rate for year-round travel.

Meanwhile, Alaska Airlines offers a Flight Pass from $69 to $129 a month that includes up to 12 roundtrips per year to 15 destinations in California, Arizona, Nevada and Utah — with no blackout dates and the option of upgrading to first class free of charge.

Southwest Airlines also offers a Companion Pass to bring someone along with you on flights almost free of charge, but not just anyone can qualify for this package. Customers must take at least 100 one-way flights or earn 135,000 Rapid Rewards points in a year to get the Companion Pass.

Companions will fly for $5.60 plus taxes and fees for one calendar year. And you don’t have to stay loyal to the same companion either. The carrier allows you to change companions up to three times per year and the pass can be used for all Southwest flights.

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As you can see, each package operates differently and can benefit certain travelers more than others.

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Are flight passes worth it?

Flight packages should be seen as an investment only if you’re a frequent flier.

After calculating how much you spend on airline tickets each year, you can decide if the flights you’ll be taking next can be with the same airline and if your destinations align with the package.

If you’re already spending more on air travel than you would on a flight package, then you’ll likely save money by buying a pass.

But if you fly to multiple destinations that aren’t all served by the same airline, then these passes probably won’t help you.

Even when you make a smaller investment like this — that could save you money in the short-term — you can start to open your mind to other, alternative ways of investing that you may not have thought of beyond your typical IRA contribution.

The more you think about how you can make your money can work for you, the closer you’ll be to building long-term wealth.

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William Koblensky Varela is a Staff Reporter at Wise who has worked as a journalist for seven years covering finance, local news, politics, legal issues and the environment.

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