Sports Hustling As A Way To Make Extra Money

Hustling For MoneyNo sooner had I published Income Profiles Of Financially Free People, did I get an e-mail from one of my online business partners saying, “NO WAY! Those profiles are absurd!”

Since he pays many full-time bloggers at least a hundred thousand dollars a year, he was the last person I thought to not believe there are plenty of enterprising people making lots of money in different ways. It was then that I realized how institutionalized our society has truly become.

Let's say you have zero entrepreneurial drive, zero creativity to produce your own products, can't write for crap, don't know how to drive a car, are unable to assemble IKEA furniture because you don't know how to follow instructions, can't read income statements, don't have any risk tolerance, don't want to start a website, and have no patience for teaching anybody anything. Do NOT believe you are screwed to work a job you hate forever!

If you don't have any of the above attributes, then surely you must have one of the most coveted attributes of all: a sports skill. What else were you doing with all your time in grade school? If you were not a nerd, you were a jock. This is America, where sports players are put on pedestals, regardless of their intellectual capabilities.


I don't condone sports hustling. I just think it's OK to take advantage of people who disrespect your abilities and have large egos. If someone wants to mock you on the playing field, then they should be willing to put their money where their mouths are! For those of you looking to make extra money, sports hustling might just be the newest extra income stream you're looking for. Let me share with you an example.

A regular tennis opponent who was 0-12 against me asked if I wanted to bet him $250 for our 13th match. It was an absurd request that I did not initially accept. Out of the 12 matches, 11 were straight set victories. But ever since he went three sets with me at the 0-7 mark, he's become obsessed with beating me.

My 4.5 opponent doesn't believe I should be a 5.0 player, even though I earned my spot based on dozens of matches algorithmically ranked by the computer over the years. Before our first betting battle, he disrespected me by saying I'd be an 80% loser to a 4.5 guy he beats 50% of the time. What kind of perverse logic is that when you've lost 12 times in a row to me? I was motivated.

USTA Tennis Rating Distribution Chart
USTA Tennis Rating Distribution Chart Up to 5.5

With his latest $250 bet request, it just felt like he wanted to donate money. He's in his late 50s, and is a mediocre 4.5 player (still, a top 5.97% of all players per the chart above). I'm 10+ years younger and rated a 5.0 (top 0.87%). We would never play each other in an official match because it would be an unfair fight. But like he says before every single match, “I've got a good feeling about today.”

Given he insisted, I took him up on his offer and beat him 6-3, 6-2, the way a 5.0 rated player should beat a 4.5 rated player. He paid $250 right away. Then he asked me when we could play and bet again. Like any gracious winner, you must let your opponent try to win their money back. He's now 0-19 and has lost a total of $1,750 so far with no signs of quitting!

Of course I got to thinking about this entire scenario from a personal finance perspective. After just 1.5 hours of a good workout, I made $250. That's $167 an hour, an amount if kept up for 40 hours a week, would equate to over $300,000 a year.

As for my opponent, he gets to play with a better player for ~$167 an hour, compared to the $100 an hour he would have to pay at a private club anyway. Meanwhile, he always has a chance to make some money too. Given he always insists and is wealthy, I really don't think he minds.


Here are some things you need to realize about yourself and your opponents before you initiate the sports hustle. Remember, your main goal is to defend your honor and prove your opponent's insults wrong!

How to position yourself:

  • People of average to below average physical stature can pull off the hustle the easiest. If you are seven feet tall, people will automatically think you're a good basketball player. But if you so happen to glide in at the average male height of 5'10” or shorter, nobody will have any idea how good or bad you really are. The smaller your stature, the more you can win because people will underestimate your abilities. Therefore, either be small or make yourself look smaller than you really are. Think Kyrie Irving turning into Uncle Drew and schooling everybody on the blacktop.
  • Downplay your attire. It's always best not to wear the fanciest gear when playing. If you've got the Nike headband, sweat-wicking polo shirt, black shorts, and matching shoes on the tennis court like Roger Federer, your opponent will probably think you are pretty good or a big time poser. It's best to wear a ratty t-shirt and beat up old shoes to set the expectation that you're just another chump. Looks matter.
  • Be naturally aloof. Look around. If you don't know who the sucker is, it's you, as they say in poker. Move on to a different court or playing field if this is the case. But once you've identified the sucker, you've got to become the naturally aloof player who doesn't understand the rules, hasn't scoped out the players, and seems totally disinterested in competing against anybody. Let the sucker fish swim to you. That's when you can start to pick and choose your opponents.
  • Lose. If your ego can handle it, it's best to first play an opponent with no money on the line and lose on purpose. Do your best to keep the match realistic so no suspicions are aroused. Once you lose, let your opponent's ego grow to the point where you're willing to challenge them for money.

Who to target:

  • Tall people. When you grow up with people constantly telling you how tall you are, it starts to get in your head that you must be better. Tall people love to look down upon shorter people, whether overtly or subtly. My 0-12 opponent is 6'2″. He calls everybody under 6 feet, “little guys.” Yet, what's the use of being 6'2″ if all he does is slice his serve instead of hit a flat serve? Nothing. At every tournament I see “little guys” beating up on bigger guys because they're faster, hungrier, and steadier. The smaller you are, the more people will underestimate your abilities.
  • Muscular people. In order to get muscular, you've got to spend hours and hours in the gym. Some of the fittest people have the lowest self-esteem. As a result, they might act like they are better than you in a sport, but deep down, they are trying to overcompensate for their lack of skills. Check out every single sport in the world. Except for football, athletes aren't overly muscular people because having too much muscle negatively affects your performance. Instead, people at the top of their sport are lean and toned.
  • Engineers, lawyers, doctors, scientists. The academically smarter your opponent the better because they, too, are used to being at the top of the class and having people tell them how smart and successful they are. The most common target is the engineer because there are more of them. They are good in math and science and always think there's an analytical solution to every problem. More than half my MBA class at Cal were made up of engineers who wanted to move beyond their boring jobs and get into management. Unfortunately for them, in sports, if you don't have the skill, stamina, or acumen, no amount of brains will enable you to win!
  • Rich people! The more money your opponent has, the more they can afford to pay, and the more they are willing to bet. Betting against rich people will also help your conscience when you win. It's like people who vote on politicians to raise taxes on other people without having to pay more themselves. They have no conscience because they just say that other people can afford to pay more! My opponent retired early at the age of 50. He owns a $1.2 million multi-unit building and has zero dependents and zero debt. He's rich enough where I don't feel bad winning up to $500 at a time.


Whenever there is a greater than 50% chance you will win, you should bet. The greater your chance of winning, the more you should press. A 70% chance of winning is good odds. But that also means that you have a 30% chance of losing. Bad beats will happen, and you should be fine with it so long as you can keep betting your opponent.

Sports Hustling Income Financial Samurai

It is very important to be humble after a win. You must compliment them on their great effort and highlight at least a couple fantastic shots or moves they've made without sounding patronizing. Then you must tell them how you got lucky with a couple of your shots as well to make them believe that you really didn't deserve to win.

Take advantage of human psychology where we like to attribute other people's success to luck, and our own success due to hard work and skill. If we say we were just lucky, our opponents will want to try again.

Once you've found the sucker, you want to hold on to him or her for as long as possible until they are milked dry. Then you move on to the next sucker who believes you aren't worthy and take them for all they've got.

The secret to sports hustling is really being attune with your own skills, while taking advantage of people with big EGOs. The bigger the ego, the greater your chance of hustling them out of their money. When you win, don't feel bad. Their egos will tell them you just got lucky. Everybody goes into a bet knowing they will either win or lose.

When on those infrequent occasions that you do lose, you should always evaluate whether your original assessment needs to be recalibrated. If you start losing a lot, then you no longer are the hunter, but the hunted. It's time to swallow your pride and start betting with lesser skilled people!


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Are You Smart Enough To Act Dumb Enough To Get Ahead

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25 thoughts on “Sports Hustling As A Way To Make Extra Money”

  1. the idea of putting “sports hustling” on my income streams makes me LOL. but hey, if you have the ability to do it (I am a terrible athlete and would get destroyed if I tried to play sports), then more power to you.

  2. Part of me wonders if he enjoys playing against you and learning from you, the “bet” is more tuition than actual bet. It’s also, to a small extent, an extrinsic motivator.

  3. This was a funny post. I am a lousy athlete – I actually really can’t even call myself any type of athlete – so I have no experience in sports hustling. This post does make me wish I was better at sports though. :)

  4. Just watch out if he wants to bet the farm on a match. Maybe he’s in it for the long hustle. If he wants to bet you $5000, watch out. :)

    1. Haha, you are right. Max bet is $500. And if I lose that, the cat is out of the bag!

      Nothing more exhilarating and wonky than playing a sport with money on the line. A 3 foot putt for $100 suddenly feels excruciatingly difficult!

  5. Hilariously fun article. I (a petite, short, underdeveloped, underestimated-my-whole-life-female) enjoyed it!

  6. Really liked this post but as a former college baseball player it would be tough to find a hustle in a team sport. Fantasy baseball provides somewhat a similar option as a side hustle and since I finished 2nd in my league last year and won $200 I decided to try and calculate my hourly fantasy wage below:

    ~2min a day to make sure all players (pitchers especially) are playing that day
    ~30min a week looking for new players to add/current players to drop

    That equates to ~45 minutes a week and for a 22 week fantasy season that equals 990 minutes = 16.5 hrs.

    With my $200 winnings I get the following hourly rate:
    200/16.5 = $12.12 an hour

    Not bad considering I would still play even if it weren’t for money. Since baseball is the longest season something like football would provide and even higher hourly rate.

    1. Apathy Ends

      $250 a match – seems like a pretty awesome deal, hope you buy the beers after!

      I stick to mens softball and fantasy sports these days, not much more than a reason to get together with buddies and have a few beers.

  7. Crystal Ball

    Good, good stuff here – maybe I’ll bet my boss a day’s salary that I can work less than him. Not quite a sport, but hey, live pigeon shooting was an olympic event in 1900, so there is some precedent for weird creativity here…. Anyway, you sorta left out the booze angle. I think the most lucrative hustling is in the Booze Sports category…which is pretty much any sport that doesnt require significant movement and allows proximity to alchohol…golf, billiards, foosball, beer pong, cornhole, bocce, catching flies with one hand, drunk yoga positions on one foot…the sky – and your creativity – is the limit the drunker your opponent gets. Hell, I won a $100 bottle of whiskey last weekend while driving a buddy back from a hike because he thought he knew more about trucks than I did (its not hard to tell a F150 from a F250 even at 90mph). I left the bottle at his house so he’ll invite me over to drink it while I use his hot tub and eat his food. It’s a win that keeps on winning!

    1. Will be tough to do unless I really focus on sports hustling. But the idea is to give people who don’t want to do other gigs or start a website other means to hustle if things get really bad.

      A lot of people who weren’t into writing, creating, playing music etc were jocks. So this post might give jocks some hope!

  8. Prof. Services Consultant

    Sam, I like the idea of making extra side money, but I struggle to figure out what the practical application would be for me.

    After all, if I’m going to disrupt my work-life balance by working more than 50 hrs a week (40 hrs of work plus 10 hours of air travel/security checkpoints/etc) then I would want it to be a really good hourly rate to make it worth my time.

    Ideally, it would leverage my existing skillset in IT/consulting. Currently I’m a technical consultant for a software company. I travel to each customer’s office for 3-5 days, teach them the software and assist them as the expert I am. So, between work, sleep, eating, and flying, there’s only so much time left to relax, work on personal projects, and finally, to side hustle.

    Driving for Uber? well, my personal car has a rebuilt title, can’t use it. Can’t drive a rental car for Uber during my business trips either. But honestly, the hourly income is way less than my day job unless I was selling jewelry in the car anyway like the one guy you told us about.

    Writing a blog? I have no passion for writing, I don’t enjoy it much at all.

    My best bet is likely to do flexible, remote consulting work of some kind which would leverage my existing skills. However, I no idea how independent consultants find these types of gigs, where I could work an extra 2 hours each weekday, maybe some hours on the weekend, and earn maybe $200 or more an hour.

    Afterall, my employer’s customers drop $9,500 for 5 days of my time, which includes all travel expenses. Subtract the travel expenses and $200/hour is basically what’s left. I only receive a portion of that:

    My salary+bonus is $75k + $10k respectively. I sold back 10 days of PTO for around $3k. My tax-free per diem in 2015 was $12k and mileage reimbursement was $10k. So, all-in my take home pay was about $90k. (which includes $18k in the 401k to save on tax)

    If I could work an extra 10 hours a week for $200/hour, I would add an extra $100k to my annual income! The problem is, I have no idea how to find that type of work, especially on a consistent, predictable basis. Any advice for me? Hell, if I could make $200 an hour I would be tempted to work 20-30 more hours a week! why not make it $300k/year :) in fact, I would be highly tempted to switch full-time to such a high-paying hustle.

  9. Anonymousinbk

    I bowl and golf for money to make it more interesting and have no problem losing 20, 30 a match to a better player. I consider it the price to pay to improve.

    1. Golf. Putt for dough, drive for show. Now that is a great sport to bet on. We’d always play Wolf when playing golf, and have Aloha presses etc. Made the game so much more fun!

    1. He’s just eccentric. He’s a nice guy. Perhaps lower on the EQ by being so blunt and insulting sometimes. But, I hand it to him for being so consistent in his desire to kick my ass! :)

  10. Have you considered that he may simply feel $250 is a fair price to pay for a serious match against a 5.0 player?

    1. Yes. $250 is about $150 over a fair price to pay as top tennis pros charge about $100/hour at the private clubs. But absolutely. In his mind, he’s think he gets a “free hit” and a chance to win money as well. I’m sure he sees the $250 bet as a discounted rate.

      I see him as a good guy to play with during the week. He’s always available no matter what time of day b/c he is retired. He’s an interesting guy who is nice and has plenty of excess cash and time on his hands.

      At least he brings new balls!

  11. I’ve been in situations like you stated above before. When I was in college, there were two A+ grade tennis players in my school. I called them A+ grade because they were always on top of every single play there was in the school. They happened to be taking the same tennis class as I and my friend were. We weren’t good compared to them. Of course, one day my friend and I went against these two players (as part of the exercise for our class). Of course, these two stoogies bet with us for like $20.

    Little did they know that I was observing how they played because I really wanted to beat them up in their game (just because they’re just bragging about it constantly). To make the story short, my friend and I played against them and won by a stretch. We didn’t say anything after that. We just took our $20 and bought some food to eat.

    Lesson learned here is that anything can be learned. Even the mightiest of the mightiest can fall because they are into themselves too much.

  12. I have done this with swimming a couple of times before. I’m short, but I used to be a serious competition swimmer when I was younger. Think Olympic trial, but not quite Olympic team.

    Twice I was steady-state cardio swimming in a lap pool. Got in conversations with some tall swimmer with expensive goggles, suits, and caps. Why you would wear that stuff for leisure swimming I have no idea. We would do some sprints, and twice I was made a bet on a race. Only $5 once and $20 the other time. I think they thought they were sandbagging, because we held tight on the sprints. Maybe they were hustling me. They never asked my swimming background.

    I politely declined both times, but with pressure … screw ’em. I won. Both times. I don’t think would would seek those opportunities. Plus, I’m a lot slower now.

  13. Distilled Dollar

    I never thought about sports hustling, but then again, my entrepreneurial spirit is just beginning.

    I have played some billiards with a few dollars on the line. Typically loser buys next round of drinks, so nothing serious.

    While I will not likely start up a side business at the bar, I do appreciate your approach to identifying opportunities. This is an excellent framework (analyzing probabilities, understanding $/hr, looking for weaknesses in a market, etc.) to work with.

    1. The entrepreneurial spirit………… this is exactly a key takeaway of this post. How to solve problems and turn bad situations into revenue opportunities.

      Hope folks can think outside the lines w/ this post, and not thing I’m some evil guy taking advantage of a millionaire tennis buddy.

      Whenever someone puts you down or challenges you, always make them bet if you think you can win. There is no point spouting bullsh*t if you aren’t willing to put your money where your mouth is!

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