Gambling Strategy: What Is the Best Way of Winning the $10 to $10K Challenge?

If your social media feed has been swamped this week by content creators trying to achieve greatness with the $10 to $10K Challenge, you’re not alone. After being brought back into the spotlight recently by Prop or Chop contributor, Calling Our Shot, the gambling craze has exploded with hundreds of others all out to make a name for themselves by hoping to accomplish the feat. But what is the best way of winning the $10 to $10K betting challenge? We enlisted the help of a math nerd in the Dimers office to help us figure out which method of the challenge really gives you the best chances of winning.

If you haven't already, you should consider signing up for DraftKings ➡️ here ⬅️ as you can turn a $5 pre-game moneyline bet on any game into $150 in free bonus bets if your team wins. 


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.

1 $10 +100 $20
2 $20 +100 $40
3 $40 +100 $80
4 $80 +100 $160
5 $160 +100 $320
6 $320 +100 $640
7 $640 +100 $1,280
8 $1,280 +100 $2,560
9 $2,560 +100 $5,120
10 $5,120 +100 $10,240

While the challenge has come back into popularity over the past week due to the exploits of Calling Our Shot - who was eventually bundled out on Day 9 - we saw some big winners during the past summer ,with a successful completion of the ladder climb by members in popular sports betting Discord Meezy’s Picks, and more recently by Twitter user @stick_wit_it540, who chronicled his daily journey via his profile page.

What is the best way to complete the $10 to $10K Challenge?

Let’s be blunt here. Winning the $10 to $10K betting challenge is really hard. If you’re thinking about embarking on your own journey up the ladder, it’s worth your time to strategize first.

We asked data analyst Gregory Tabor to run some equations for us, based on a variety of different methods and approaches that we’ve seen to complete the challenge. 

But before we get into the nitty gritty of what our calculations uncovered, it’s important to remember that betting is, in fact, a numbers game. While you may see odds when you login to your sportsbook app, those odds have an implied percentage figure assigned to it; something professional bettors will use as part of their models (like the prediction models you see at to marry up their data projections against the odds of the ‘books to find the edge. For example: a straight bet that equates to odds of +100 has an implied percentage probability of 50%. In other words, when you’re betting even money, there’s half a chance you’ll win, and half a chance you lose. It should also be mentioned that sportsbooks build in a 5% hold into their markets -  i.e: making the odds worse in order to turn a profit, regardless of whether a prop market hits on the over on under. That's why in standard markets where only one of two things can happen (such as an over or under), both options will be listed at odds of -110. 

Scenario 1: The Four-leg +100 Parlay

Let’s look at the method we’ve seen deployed recently by Calling Our Shot and others in the past week, who have elected to pool together four short-priced legs into a parlay to get to odds of +100. The average odds for a four-leg parlay to get to the magical even-money sum is -526. Isolated, that leg has an 84.03% chance of hitting. Sounds like a lock, right?

Well, when you start putting together multiple legs that all have a 16% chance of losing, you’re increasing your risk that something could go wrong. Using this method, over the span of 10 days to reach $10,000, our calculations say that you’ll only hit the target in 1 out of every 8049 attempts. This is factoring a standard 5% bookmaker hold.

RELATED: The Best Sportsbook Sign-Up Promos

Scenario 2: The Two-leg +100 Parlay

Another popular method is creating a two leg parlay at odds of around -250 (71% chance of hitting in isolation) to get to +100 and continuing to roll from there. Our calculations show this is a much smarter option, cashing the $10,000 in 1 out of every 2300 tries. Essentially, less legs equals less risk.

Scenario 3: The Straight +100 Bet

Okay, so we now know that the less legs we put into our challenge, the less chance we have of something going wrong - so this is for you old school gamblers out there that look at a parlay like it’s some kind of scarlet letter. Betting singles in this challenge is actually your best chance of ascending to greatness.

Based upon our data, hitting just 10 single bets over the course of 10 consecutive days would see you hitting the $10,000 mark in 1 out of every 1700 attempts

Scenario 4: Start With $20

Now that we’ve established that betting single bets is the most effective way of hitting the $10k ladder challenge, let’s throw in another variable. What if instead of the $10 to $10k challenge, it was the $20 to $10k challenge?

Our calculations show that by just removing one day from the 10-day challenge, you dramatically increase your chances of winning.

If a bettor was to start with a bankroll of $20, betting a single bet at odds of +100, you would cash the challenge in 1 out of every 806 attempts.

So there you have it. There are many different ways you can climb the ladder to $10,000, but some ways are better than others. Completing the $10 to $10k challenge is do-able, but having a strategy is key. As they say, failing to prepare is preparing to fail.
Thinking about starting your own $10 to $10K Challenge? Check our the Dimers' Best Props page for our data model's best bets and prop projections.
Related Articles
More Articles
More from Dimers
About Dimers
icon 22,000+
Events covered in 2022
icon 2,700,000+
Visit our partners