How to Win the $10 to $10K Betting Challenge: The Two Bettors Who Completed It

Ask any recreational gambler and they’ll tell you that the $10 to $10K Challenge is the hardest sports betting journey you can embark on. Beginning with $10 and trying to turn it into $10,000 over the course of 10 days, not only takes skill, but nerves of steel, and a little luck, too. With the popularity of the $10 to $10K Challenge recently being thrown back into the spotlight, there has been an explosion of bettors who have all tried their hand at achieving the ultimate payoff. But how many have actually been able to complete it? The data shows that the  odds of completing the $10 to $10K challenge are stacked against you, but it can, and has, been done before. Dimers.com spoke to two pioneers that were able to win and tell the story.

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What is the $10 to $10K challenge?

Also known as the Ladder Challenge, the concept is simple: a bettor begins by placing a $10 bet on Day 1, generally by putting together multiple short-priced legs to combine for odds of close to +100, then rolling over the winnings into Day 2. And so on and so forth until ultimately, the $10,000 target is reached on Day 10.

Has anyone won the $10 to $10K challenge?

Prior to their involvement as members of the Meezy's Picks VIP Gambling Discord, Hannah, a 28-year-old from Colorado, and Shane, a 33-year-old from Illinois, didn’t know each other. Brought together via the Discord community, they had seen the $10K Challenge attempted online before and were intrigued.

Shane, a capper in the Discord, who is also on Twitter under the handle @lockprops, told Dimers that members of their community had asked him to attempt the feat with Hannah - a Community Star in the chat.

“Our first attempt we failed pretty early into it, in our second attempt one leg was voided so we restarted it over,” Shane said.

The third time would eventually turn out to be the charm.

Originally setting out on the challenge in May 2022, the duo focused on a combination of basketball and baseball props to create their bets, which usually consisted of 1-3 legs, accounting for parlay odds of around +100.

But as many others have found time and time again, succeeding in the $10 to $10K Challenge is extremely difficult. In fact, we recently ran the numbers and discovered that by taking just one straight up bet at odds of +100 for 10 consecutive days, bettors would only reach the $10K figure in 1 out of every 1700 attempts.

STRATEGIES: The best ways to win the $10 to $10K challenge

Hannah, who goes by the Twitter username @BiggerTheBettor and worked with Shane in researching and deciding on which legs would comprise each day’s parlay, said that not thinking too far ahead initially was key.