I received an email from one of my online business partners right after I published, exclaiming, “NO WAY! Those profiles are absurd!” He’s a big spender, dropping at least a hundred grand annually. I never expected him to doubt the abundance of savvy folks making serious cash in unconventional ways. It hit me then how ingrained our society really is.

Picture yourself without a hint of entrepreneurial spirit, zero creativity to craft your own products, writing skills that are practically non-existent, unable to drive, incapable of putting together IKEA furniture due to poor instruction-following, clueless about reading income statements, zero risk tolerance, no interest in teaching, and zero patience for coaching anyone. Do NOT think you’re doomed to toil away in a job you hate forever!

If none of those apply to you, then you probably possess one of the most prized attributes of all: athletic prowess. What else were you doing all those years in school? If you weren’t a nerd, you were probably a jock. That’s America for you, where sports stars get put on pedestals, regardless of their IQs.

I don’t endorse hustling in sports, but I think it’s fair to capitalize on people who disrespect your skills and have massive egos. If someone’s willing to ridicule you on the field, they should be ready to bet on their words! For those of you keen on earning extra bucks, sports hustling might just be the fresh income stream you’ve been eyeing. Let me share an example.

One of my regular tennis opponents, who was winless in 12 matches against me, proposed a $250 bet for our 13th match. It was a ridiculous proposition I initially brushed off. Out of those 12 matches, I’d won 11 straight sets. But ever since he took me to three sets at 0-7, he’s been fixated on beating me.

My opponent, rated 4.5, questioned my credentials despite my algorithmically earned 5.0 spot over many years of computer-ranked matches. Before our first bet, he scoffed that I’d be an 80% loser against a 4.5 player he beats half the time. What kind of logic is that after losing 12 times in a row to me? It fired me up.

Time to Place Bets!

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With his latest $250 bet request, it seemed like he was just itching to hand over money. In his late 50s, he’s a mediocre 4.5 player (still in the top 5.97% of all players per the chart). I’m over a decade younger and rated 5.0 (top 0.87%). We’d never square off in an official match because it’d be a mismatch. But before every match, he’d always say, “I’ve got a good feeling about today.”

Since he persisted, I took him up on it and handed him a 6-3, 6-2 defeat, exactly how a 5.0 player handles a 4.5. He promptly handed over $250. Then he asked when we could play and bet again. As a gracious winner, you’ve got to let your opponent try to win their money back. He’s now 0-19 and down a total of $1,750, yet shows no signs of quitting!

Naturally, I started thinking about the entire situation from a personal finance angle. In just 1.5 hours of playing, I made $250. That’s $167 an hour. If I kept that pace for a 40-hour week, it’d tally up to over $300,000 a year.

For my opponent, he gets to spar with a superior player for about $167 an hour, compared to the $100 an hour he’d shell out at a private club anyway. Plus, he always has a shot at making some money. Considering he’s wealthy and always insists on these bets, I doubt he minds.

Setting Up the Hustle

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Here’s what you need to understand about yourself and your opponents before diving into sports hustling. Remember, your goal is to defend your honor and prove your doubters wrong!

How to Position Yourself for Sports Hustling:

– People of average or below-average physical stature have it easiest. If you’re seven feet tall, everyone assumes you’re a basketball ace. But if you’re average height or shorter, people won’t know what to expect, which can work in your favor. So either stay small or create that illusion.

– Dress down. It’s wise not to flaunt fancy gear. If you’re decked out like Roger Federer in Nike headbands, sweat-wicking polos, and matching shoes on the tennis court, your opponent might think you’re top-notch or just posing. Opt for a raggedy tee and beat-up shoes to set the stage as just another average player. Looks count.

– Act nonchalant. Scope out the scene. If you’re unsure who the mark is, it’s probably you, as they say in poker. Move to another court or field if that’s the case. But once you spot your mark, act aloof, like you don’t know the rules, haven’t checked out the competition, and aren’t interested in competing at all. Let the fish come to you. That’s when you can start picking your opponents.

– Lose intentionally. If your ego can handle it, lose a casual match with no money at stake. Keep it believable so as not to raise suspicions. Once you’ve let them win, let their ego inflate until you’re ready to challenge them for cash.

Who to Target for Sports Hustling:

– Tall people. When everyone’s always mentioning your height, it’s easy to start believing you’re superior. Tall folks enjoy looking down on shorter ones, overtly or subtly. My 0-12 rival is 6’2” and calls anyone under 6 feet “little guys.” Yet, what good is being tall if all you do is serve slices instead of flat shots? At tournaments, I’ve seen shorter guys take down bigger opponents by being quicker, hungrier, and more consistent. The smaller you are, the more people underestimate you.

– Muscular individuals. It takes hours of gym time to bulk up. Some of the most muscular people suffer from low self-esteem. They may act superior in sports, but deep down, they’re overcompensating for lack of skill. Look across any sport, excluding football; the top athletes are lean and toned, not overly muscular.

– Engineers, lawyers, doctors, scientists. The smarter your opponent, the better, as they’re used to being at the top of their class with everyone praising their intelligence and success. Engineers are prime targets due to their analytical mindset. Over half my MBA class at Cal were engineers seeking to rise from mundane roles into management. Sadly, in sports, brains alone won’t secure victory if you lack skill, stamina, or game sense.

– Wealthy individuals. The richer your opponent, the more they can bet and afford to lose. Betting against wealthy opponents also eases your conscience when you win. It’s like voters backing politicians who hike taxes for others but not themselves. They feel no remorse since they argue others can afford it! My opponent retired early at 50, owns a $1.2 million multi-unit property, and has no dependents or debt. He’s rich enough that winning up to $500 at a time doesn’t faze me.

Sports Hustling: Post-Win Attitude

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Whenever you have over a 50% chance of winning, take the bet. The higher your odds, the more you should push. A 70% chance of winning provides solid odds, but also means a 30% chance of losing. Bad breaks happen, and you should accept them as long as you can keep betting your opponent.

After a win, humility is key. Compliment them on their effort, highlight a couple of their great shots or moves, and avoid sounding patronizing. Then mention how lucky you got with a few of your own shots, making them believe you didn’t really deserve to win.

Harness human psychology, where we credit others’ successes to luck and attribute our own to hard work and skill. If we admit we were merely lucky, our opponents will want a rematch.

Once you’ve identified a mark, hang onto them until they’re tapped out. Then move on to the next skeptic who doubts your worth and milk them dry.

The secret to sports hustling lies in knowing your own strengths while exploiting big egos. The bigger the ego, the better your chances of hustling them out of their money. When you win, don’t feel guilty; their egos will convince them you just got lucky. Everyone goes into a bet knowing they might win or lose.

On those rare occasions when you lose, reassess your approach. If losses mount, you’re no longer the hunter but the prey. Swallow your pride and bet against less skilled opponents!

Related Posts on Sports Hustling:

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