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Categories Betting 101

How to Win By Tailing Sports Betting Experts

Updated January 19, 2025 | 8:04 am CDT by Sam Smith
How to Win By Tailing Sports Betting Experts

In sports betting, the goal is simple: Consistent wins and long-term profitability. Getting the job done, however, requires navigating a world of complex odds, ever-changing lines and relentless competition. One path to success is tailing a sports betting expert — a strategy that is made easier upon using Tails By OddsShopper. Here’s how you can leverage expert picks to win consistently.

How to Win By Tailing Sports Betting Experts

Tailing a sports betting expert means following the bets of someone with proven expertise in identifying positive expected value, aka +EV bets. Experts often excel because they understand two critical principles:

Market Inefficiencies: Not all sportsbooks price games the same way, and many markets — especially smaller or niche ones — are prone to inefficiencies. Sharp bettors thrive by exploiting these inefficiencies before the market corrects itself.

Access to Better Information: Experts often combine advanced tools, deep research and years of experience to identify value that casual bettors overlook.

By tailing experts who operate with these principles in mind, you effectively outsource the most challenging parts of sports betting: Identifying which bets offer true value.

The Tails By OddsShopper Advantage

Tails By OddsShopper is a game-changer for anyone interested in tailing sports betting experts. Tails is a database of sports betting experts willing to share their expert picks and insights, and you can follow one, a few or all of the experts to get the best-quality information possible. Tails experts offer:

Market-Based Modeling: Many of our experts use Portfolio EV, which scans sportsbook odds and compares them to market-derived “true” odds, ensuring every recommended bet has value.

Expert Insights: Every pick is vetted by experienced analysts who understand how to exploit market inefficiencies effectively.

Transparency and Trust: With a track record of success and detailed EV results tracking, you can always be sure you’re betting with confidence.


We’re even offering Tails By OddsShopper for FREE (as in $0) if you sign up with one of our partners.

You can select whatever sportsbook or DFS site is your favorite from the offered list, then claim Tails By OddsShopper to help increase your odds at making +EV decisions and growing your bankroll.


Tips for Successful Tailing

Trust the Process, Not the Outcome

Betting is inherently streaky. Even the best experts go through periods of losses. Instead of focusing on short-term results, trust the process that identifies +EV bets. Over time, mathematical edges compound into profitability.

Bet Consistently and Within Your Means

Bankroll management is critical. Decide on a flat bet size — our users often prefer 1% to 2% of their total bankroll — for each bet and stick to it. This prevents emotional decisions and protects you from large swings.

Diversify Your Bets

Don’t put all your eggs in one basket. Experts often recommend a variety of bets across different markets, and Portfolio EV recommends placing as many bets as possible within your bankroll management via the Mass Entry Tool. Building a portfolio and following it in full, rather than cherry-picking a few, increases your likelihood of long-term success.

Act Quickly

One of the most valuable lessons is that +EV opportunities don’t last long. Sharp bettors and line movements can quickly erase value. Our tools provide real-time notifications, so you can jump on profitable bets before they disappear.

Open Multiple Sportsbook Accounts

To maximize your access to the best odds, you need accounts at multiple sportsbooks. Odds often vary across books, and having options ensures you’re always betting at the most favorable line.

How Tailing Differs from Blindly Following Picks

Tailing a professional isn’t about blindly trusting their judgment — it’s about leveraging their edge while understanding the underlying principles. When experts recommend bets, they rely on data, analysis and market insights to make informed decisions. By following these picks through Tails By OddsShopper, you’re effectively joining a team that has already done the hard work.

The Long-Term Edge

Learning how to win sports betting is a long-term grind, not a get-rich-quick scheme. Tailing an expert is one of the most reliable ways to secure that edge. By focusing on +EV bets, practicing disciplined bankroll management, and using Tails By OddsShopper, you’re setting yourself up for sustained success in a field where most bettors fail.

Portfolio EV Free Trial: Get 7 Days of +EV Betting Tools FREE!
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Sam Smith

Author

Sam Smith

Sam Smith is a writer and editor with Stokastic and OddsShopper. He has been immersed in the world of professional sports data since 2015 while also writing extensively on the NFL for a multitude of blogs and websites. With OddsShopper, Sam looks to blend his sports and editorial expertise with OddsShopper's data to bring you the best betting information possible.

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