The Winner's Dilemma

The Winner's Dilemma
Aaron Chou
November 19, 2020
Inside casino, screens of sportsbooks stats and sports betting picks
Maximizing Profits from your Sportsbook


In its most basic form, sports betting markets are very much structured like traditional financial markets - exchanges/sportsbooks offer a price for a stock/team that you wish to bet on, and if the stock/team you bet on outperforms expectations/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 printing money and cleaning out a sportsbook, we will get flagged quickly and have limits placed on our account. Here’s what you have to do to maintain your money printing operation:

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. 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%. That means, on average, your money doubles after just four rounds of betting.

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.

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 and avoid suspicion. We have to balance our profitable edges 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 break even and put enough volume down that books do not shut us out of the derivatives/prop markets. You should target a split of at least 2/3 sides and 1/3 prop bets.  In other words, for every dollar you bet into the prop market, you should bet two dollars into sides and totals.

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