The Winner's Dilemma


In its most basic form, sports betting markets are very much structured like traditional financial markets - exchanges and sportsbooks offer a price for a stock or team that you wish to bet on, and if the stock or team you bet on outperforms expectations or wins, you make money. If you are wrong and it underperforms, you lose money.

However, there is a significant catch. Having a winning betting strategy in sports betting is not enough to make a living out of sports betting. Maintaining a good relationship with your sportsbooks is critical to long-term sustainability. Unlike financial markets, sports betting markets are not exchanges - the person you are betting against is always the sportsbook, and one of you has to lose. In the financial markets, brokerages that you buy and trade stocks on generally only facilitate transactions without having a position. This is problematic for us - while a brokerage that holds your money is agnostic to your financial performance (and would probably prefer that you make money), sportsbooks only make money when you lose money. It is in their best interest to identify and limit or remove winning players. Therefore, if we are cleaning out a sportsbook, we will get flagged quickly and have limits placed on our account. For those interested in becoming more serious about sports betting, here are some keys to long-term sustainable betting.

Keys to sustainable betting

  1. Have a winning betting model and strategy

Like financial markets, sports betting markets offer derivatives/ancillary products that can be highly profitable - prop bets in particular are easily beatable. Finding softer and less liquid markets is a key ingredient to any winning sports betting strategy. We estimate based on our current prop betting strategy, we can generate 20% ROI on every prop bet we place with a win probability between 60-70%.

For further details of our prop betting winning strategy click here

  1. Multiple Accounts - dilute your profits across multiple books

By signing up for multiple accounts and spreading your bets across multiple sportsbooks, you can decrease the chances of getting flagged because it spreads the concentration of your profits across multiple operators. It also gives you options - if one book shuts you out, you have other outs to work with. The offshore books we recommend you sign up for first are BetOnline, Bookmaker, and Bovada. After that, YouWager and Heritage are also reputable alternatives. We do not have any affiliation or relationship with these operators, but in our experience we have found these sportsbooks to be the most reliable.

For instructions on how to set up and fund a sports betting account click here

  1. Diversification - Maintain a good relationship with your sportsbook by decreasing your margins and placing less profitable bets

Yes, you read that right. You have to place bets that are breakeven or even slightly unprofitable. Betting sides is like eating your vegetables and a necessary evil to maintain a good standing with sportsbooks. There is no reason for a sportsbook to keep you around if all you are doing is betting the maximum limit on prop bets and other soft markets. You will quickly get limited. We have to balance our high-margin bets with less profitable bets in their core markets, called sides and totals. This is when you bet a side of the game - usually against the spread in games, or a total - taking the over or under. While we believe we still have an edge betting these markets, our expectation and goal betting sides is merely to  put enough volume down that books do not shut us out of the derivatives/prop markets.

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