It’s safe to say that only the most famous sharps get interviewed long enough to talk about their wins and victories, so it’s rare to see one talk about regrets in sports investing. Stuck in an airport on my way to an industry conference, I hit the lounge to kill some time and ran into one an industry veteran sharp. So what the hell was I supposed to do but buy him a few drinks and swap some stories.

One of the most memorable points we talked about was his biggest regrets wagering on sports as a profession.  After 20 years in the industry, what I learned that evening was there are still points anyone from the average weekend Joe sports bettor, to the avid sports investor and sharp could learn from this guy. The devil is in the details.

The answers to his biggest regrets over the years as a sharp wagering mostly on the NFL were surprising to me. And in his own words, I promised not to divulge his name and specifics of his character if I shared our conversation to our members at So grab a beer, sit back, and listen up.

1. The one that got away

There will always be that one game that sticks out like a sore thumb. It usually isn’t a loss: losses go away. It’s always one that you made money on. A little bit of money. One that you could have made a lot of money on, because you were that sure, but you doubt yourself and instead of betting $5,000, you bet $500. It will always be a big game, and you’ll even notice those celebrating around you as you realize you hit it exactly and knew you needed to do more. 

When he told me this one, man could I think of a few times I was in those shoes and not walking away from that as a learning experience for the next big opportunity.

2. Not using more sports books on (what you believe to be) sure things

First off there is never a sure thing, so is in life and business. But a sound strategy will give greater confidence and probability of the win. Secondly you should be using multiple sports books anyway. Why?.  Always shop around for the best return. You do it when you go shopping for a TV, car, or latest tech., so why not on your sports betting?

(Side note here, the team at will soon be launching a odds comparison service for free within the members area. You’ll get a one-stop-shop view to compare odds in real-time against multiple sports books, and set alerts on the odds of your favorite game to get notified if and when the odds change. Hold tight – it’s coming soon.)

But there is another reason to make sure to use multiple books on games that you’re sure of: oftentimes bets can be capped with a single bookmaker, especially if you’re a little too successful. Using multiple sports books with a confident strategy helps avoid all that.

3. Trying to be creative too often cost me money too often

It’s a good idea to try to make your betting system as precise and as workable as possible. But there is such thing as being too precise, which begins to start looking more and more like superstition. Don’t make that mistake. Because if you do, you’re going to lose money needlessly, and in the end the name of the game is minimizing loss and risk.

4. Time wasted not keeping cool

It sounds silly, but a bad weekend or a bad run can put you in a slump. It can get in your head. Why do you think the NFL has Monday night football? (entice sports bettors to make up for their losses from NFL Sunday). And a lot of the times when you hit a bad run it and in over your head it could mean the end of a sports investing career.

But for the survivors, it just looks like time wasted. It’s pathetic. It’s not about your luck, it’s about luck overall, and your ability to reduce its influence in predicting outcomes. It’s about sound strategy informed by data that builds confidence outcomes and profitability ‘over time’.

5. Stupid gambling

Everybody does it at one point or another– some at the beginning, some for fun, and some at the end. You lay a bet you don’t know. You’re bored. It looks interesting. It’s like Powerball! It’s a waste of f@$## money.

Sorry boys, I hate to be a killjoy but this is seriously my biggest regret. I can tell you how many times I won from stupid gambling. NEVER. It’s not logical. It’s not sound. It gives no confidence in establishing a profitable approach and betting system. And yes, it does not pay out. Ok, sure you may of had a few drinks and some good chats and in the end and this was your excuse to make you sleep better at night, but you blew money that you could have used effectively to build up your bankroll nest egg. All for nothing.


What is a sharp?

If you’re not familiar with what is a sharp, it’s a sports betting term that refers to a person who is a professional gambler or sports investor, one who can also be called a “wise guy.” The opposite of a sharp is a square – a public bettor. The easiest way to understand the differences between a sharp and a square is just to break some of them down:

  • A sharp bets to make money. Emotions don’t factor into their decisions. They don’t bet because they want action on a given day. If there is a good bet they make it. If there isn’t they will happily pass instead of throwing money at a bad deal.
  • A sharp is strategic about the size of his bets. He has a sound money management plan and he sticks to it over the long term. Square bettors often chase loses, but sharps never will.
  • Sharps use detailed analysis to come to their betting decisions. They may rely on math, statistical analysis, video replay, the application of tested angles, or another approach that they have developed with time and effort. Unlike squares, what they will not do is bet a hunch, bet on teams they like, or bet on a game because they want it to be more interesting to watch it.
  • Sportsbooks are much more aware, and concerned by, sharps than squares