If you’re like me, you’re looking to reach FIRE* by any means possible. Side hustles, investing, whatever. We’ll take what we can get, right? If you have read my blog before, you know that I’ve made some extra money through ways that others might consider abnormal. But the most unlikely way I made money was many, many years ago, when I won a March Madness contest.
Yeah, really.
Photo by Markus Spiske from Pexels
Welcome, Camp FIRE Finance readers!
An aside
Let’s start with the elephant in the room: yes, I won a bunch of stuff on Wheel of Fortune a few years ago. (I still drive the car, as of this writing.) But yes, I have actually also won money in a March Madness contest. I’m an extremely lucky so-and-so.
(That I haven’t come anywhere close to FIRE after both those things happening says a lot for either my family’s health problems, my career path, or my extreme lack of planning. Or probably all of the above.)
Yes, people win March Madness contests
For those people who don’t play the lottery, I would imagine that March Madness represents the biggest pie-in-the-sky pipe dream of the year. Can’t you just picture it? Pick 63 games correctly, and take home the dough. (There was a time, which I believe is long gone, when sites offered megabucks for anyone who picked a perfect bracket. No one ever collected on that.)
But do people ever win? Sure, someone wins on each of these sports sites offering a March Madness contest. The odds of winning are astronomical, as they are with most of these things.
Unless things line up just right, I guess.
So how’d I do it?
I have entered brackets into loads of March Madness contests every year for well over two decades. (So have loads of you, probably.) We all know the big sites for this; ESPN is by far the biggest at this point, though others (Yahoo, SI, etc.) have had their contests as well.
In a much younger internet, there were little fish looking to break into the big time. One of them was a now-defunct website called eLotteryFreeway, run by a company called eLottery. In the year 2000,** eLotteryFreeway was a fledgling site presumably trying to drum up a few more players. Their big idea: give away $10,000 in a March Madness contest. Why not?
I, always looking for a side hustle idea, had stumbled across the site, and I convinced two co-workers to create brackets along with me. The winner, out of the three of us, was to be treated to lunch at Wendy’s (the only restaurant anywhere near our office at the time).
The only real reason to enter a March Madness contest, apparently. Image by Michael Form from Pixabay.
Had I watched much college basketball that year? Heck, had I watched any? I doubt it. Did that stop me from creating a bracket? It never had before (or since).
But how did I actually win?
Our story thus far could be anyone’s: guy with minimal knowledge of the teams in the NCAA tournament creates bracket with the hope of free lunch.
Enter dumb luck.
In recent years, a lot of #1 seeds made the Final Four. That was not the case in 2000, though. No, the seeds of the Final Four that year were: #1, #5, #8, and #8. Yes, two #8 seeds made it. And I managed to pick three of the four teams.
Indianapolis, where college basketball players were playing for me to win money. Or something.
(I couldn’t find a royalty-free pic of the RCA Dome, so this will have to do. Image by David Mark from Pixabay)
I’ll pause here to mention that eLotteryFreeway’s scoring system for their March Madness tournament was different from any other site I have ever seen. The points were so high for the last couple of rounds that by way of correctly picking three out of the Final Four, I was sitting atop the leaderboard…but if I got the last game wrong, I could still lose.
You can imagine how I felt watching the final. I think I was on the edge of my seat for two hours, hoping Michigan State would beat Florida. Thankfully, they obliged.
Then what?
I hardly believed I had actually won. I was even more incredulous when, via first class, non-registered mail, a check for $10,000 showed up in my mailbox.
Well, the first thing I did was to take the two co-workers with whom I had been competing, as well as a few other co-workers, out to lunch. It seemed right at the time.
And then the next thing we did was to use the rest for a house down payment. To think: if not for this, we probably would have been stuck in an apartment for another year or so. Maybe longer, since we weren’t saving or investing much at the time.
In the meantime, eLotteryFreeway disappeared about a year later. I did manage to win a little bit more from them before they went away (through other, smaller games), though far less than $10,000.
Why not enter?
I’ve continued to enter my brackets year after year since then, but, as might be expected, lightning has not struck twice. But I enjoy creating March Madness brackets, so I keep doing it. If I ever win again, it’ll just be a bonus.
(I will point out that doing so as part of a pay-in office pool is not always a great idea, particularly if you haven’t been following college basketball. You might just be flushing your $5, or $10, or however much it is. Plus, there’s the whole thing about office pools not necessarily being legal in all jurisdictions. Do your research, and make your own judgment.)
That’s the thing: a lot of these things I do (and the things you can do) don’t offer good chances of winning much at all, but if you enjoy them, what’s the harm?
Of course, I wouldn’t recommend letting such things take over all your time. After all, if you’re like me, you have a day job that needs a lot of attention from you. (A job that, probably, looks down on using company time for March Madness brackets. Not that this stops people from doing that on company time…)
But there’s nothing wrong with taking a little spare time to prepare a bracket or two each March. You never know; you might get really lucky some year. I did.
But I never did get that free Wendy’s lunch.
* Financial Independence, Retire Early. I am nowhere near either of these things.
** If you ever watched Conan O’Brien, you heard that phrase in the falsetto of “La Bamba”, didn’t you?
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