No 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.
SPORTS HUSTLING FOR EXTRA INCOME
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.
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.
SETTING UP THE HUSTLE
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.
ATTITUDE AFTER WINNING
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.
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!
Recommendation To Build Wealth
Manage Your Money In One Place: Sign up for Personal Capital, the web’s #1 free wealth management tool to get a better handle on your finances. In addition to better money oversight, run your investments through their award-winning Investment Checkup tool to see exactly how much you are paying in fees. I was paying $1,700 a year in fees I had no idea I was paying.
After you link all your accounts, use their Retirement Planning calculator that pulls your real data to give you as pure an estimation of your financial future as possible using Monte Carlo simulation algorithms. Definitely run your numbers to see how you’re doing. I’ve been using Personal Capital since 2012 and have seen my net worth skyrocket during this time thanks to better money management.
Updated for 2019 and beyond.