Thursday, Sep 5th
Monday, Sep 9th

Never Raquel

Similar to the way OWS provides data-driven analytics week-to-week around specific matchups, my goal through Betting Sharp is to provide statistical advantages in the betting world that can help you make educated and confident decisions.

And we should start by saying this ::

all gamblers lose.

Go in knowing that you are going to lose 40%+ of the bets you wager. But in the same way a baseball player can build a career out of getting a hit 28% of the time, a sports bettor needs to win more than 52.4% of bets, over time, to beat the vig. In fact, when most people read that, the tendency is to think, “52.4% doesn’t seem like all that much. I know a lot about football, after all.” But Vegas is good! (Like…really, really good.) So we want to always be on the lookout for unique angles that may go overlooked elsewhere.

So the big question, really, is: why listen to me?

Honestly? I wouldn’t — not solely, that is. You should always do your independent research and make decisions based on YOUR research and YOUR confidence with such picks. 

But why listen to me anyway?

I’ve been doing this a long time. I began gambling when I was 14 years old in small home games, and at 16 I began sneaking into casinos to play poker at least five nights a week.

Eventually, I graduated into large home games, where guys had built entire 4,000 sq/ft “homes” to house large-scale poker games: cameras everywhere, professional dealers, cocktail waitresses, free food and drinks. I was completely enveloped in a gambling world.

Somewhere along the journey, I began betting on everything from turtle races to spelling bees to 100-to-1 odds on guessing strangers’ names. (Don’t guess Raquel. It’s never Raquel.) My biggest wins came from my biggest losses, because I learned that no bet is infallible and losing is inevitable. The goal is to give yourself a statistical advantage over your competitors. There is inherent risk in any wager ever made (imagine the confidence the Falcons bettors had at 28-3 in the Super Bowl). 

Ultimately, gambling of any sort (poker; football; being named Raquel) comes down to one thing:

What are the odds of winning this bet, in this moment. Obviously, there are some constants and some variables (that’s why it’s called gambling…duhhhhh), but if you play the same consistent strategy over time (assuming it’s a winning strategy), you will win long-term and tell your grandkids about all of the suckers you took money from. However, if you only play your “winning” strategy 50% of the time, the other 50% of your bets become wildly unpredictable. Don’t come back crying because you played the DeSean Jackson Revenge Game expecting him to go for 150 yards with 3 TDs (honestly, I’m a sucker for these bets too; when they hit, they’re a blast). When he hits all of his season averages and only nets you 13 yards on 2 catches, you’ll say to yourself, “shouldn’t have bet that one.”

The first question you need to answer is for yourself. What kind of gambler do you want to be? Is your goal to be a professional gambler? — do you maybe imagine a Darren Rovel tweet going out one week about you moving entire lines with your multi-million dollar bets? Are you trying to enhance your sports watching experience and give yourself more things to sweat on Sundays? Are you trying to hunt for the best angles: betting tight-and-aggressive as you churn out some extra income on the side? Or are you just trying to spice up your life with some thrill, fun, and a little bragging rights amongst the bros? I know it sounds silly, but you genuinely need to answer this question:

Why am I gambling, and what is my goal? 

For me? Each and every bet I win is equitable, in that moment, to hitting the jackpot. I feel, momentarily, like the smartest person in the world. “You idiots didn’t know Jameis Winston was going to put together one complete game, against the 9-point favorite Rams?” Pshhh give me my money! (Okayyy, NO ONE can see that coming; but you get the idea.)

No matter the size of the bet, just knowing that I knew something someone else didn’t and hammering that edge is pure bliss. I get to mix almost everything I enjoy in life: competition, sports, and money. It’s heaven.

So, first — answer that question.

Then once you determine what kind of gambler you are:




Budgeting is more important than picking teams to bet on. Whether you have an annual budget, a weekly budget, or somewhere in between, you HAVE to stick to your budget. (I cannot say that enough.)

I budget according to what I’m comfortable wagering on any bet. I have never been a whale, a shark, or any other euphemism for a throw-my-weight-around gambler. Again, I get the same amount of enjoyment out of winning $1 on a game of cornhole as I do wagering $500 on the Super Bowl. Knowing my why makes it easy for me to budget. My why is pure competition: I HATE losing.

Knowing that about myself, I have two bank accounts dedicated to gambling. One is my immediate bankroll. I’m willing to lose it all in one night, or over a weekend, or by challenging my friend to a 40-yard dash (I’m slightly faster than Tom Brady; come get some). My second account holds my winnings — that is, my “disposable income” — but it’s not up for grabs in the blink of an eye. I’ve had quite a bit of success in my life gambling — whether in poker, fantasy sports, or just betting the games straight-up (mostly NFL, NCAAF, and NBA) — so I am still playing 14 years later off of my original investment. 

You don’t have to use my method for keeping track of your winnings and bankroll, but you need a system of some kind

NEVER risk money that is not disposable. 

NEVER try to bet your way out of a hole. 

NEVER play outside of your budget. 

In my experience, once you stretch beyond what you have budgeted for gambling, it changes the way you play the game. When I was 22, I thought I was ready for the “big game” myself. I was a pretty typical $2/$5 player (these represent the blinds, or pre-flop wagers — for non-poker players), buying in each night around $300-$500 depending on other players. I went on a heater for a few weeks and grew my bankroll to a little over $12,000, and I decided to skip the $5/$10 game and hop straight to the $10/$20. If you’ve seen Matt Damon in Rounders, you know how this story ends.

Luckily, I did not lose my entire bankroll. But I went outside of my comfort zone and donated (lost) about $7,000 to learn a valuable lesson. No matter how good or certain you are, you are going to lose sometimes. You have to budget accordingly. 

Personally, I use my second bank account to “stake” my bankroll account. I ALWAYS have at least 3x backing my bankroll account, and if it shrinks below that, then my bankroll shrinks. No exceptions. I never risk more than 5% of my bankroll on any sports bet. This eliminates my ability to chase losses or throw away my winnings quickly. Weekly betting on sports is different to me than playing craps, poker, or one-off bets (I do wager more than 5% of my bankroll when I’m buying into a poker game; the 5% is just a standard rule-of-thumb that I use as a guide). However, I am hardline on never re-upping my bankroll in the heat of a moment, a 12-hour poker bender, or on a gambling trip (Vegas, Atlantic City, etc.). I recently went to Vegas for a bachelor party and took $1300 with me to gamble with. Before a trip like that I always want to take cash to eliminate any desire to withdraw more from an ATM. If I lose it all in night 1, I am done gambling for the trip. I do not chase losses and that is the max I was willing to wager on this trip.

We have a lot more to get to. And knowing JM and myself, I imagine we’ll end up giving you more than we currently even realize. But we’ll leave it at that, for the moment. And we’ll see you in the free video lesson on Finding Profitable Bets on the next lesson of this course.