How to Make Fantasy Football a Legitimate Side Business


Fantasy sports is a growing industry in North America. In 2015, 56.8 million people in the United States and Canada participated, investing a whopping average of $465.

While these numbers account for every type of fantasy sport, an overwhelming 73% of these players are making bets within their fantasy football leagues.

The History of Fantasy Football.

The first fantasy sports venture was started because of football, in fact.

In 1962, Bill Winkenbach and a few friends, who were part of the Oakland Raiders Organization, decided upon the basic rules of fantasy football. The next year, the first draft was made. Six years later, the first public fantasy football league opened for the customers at the Kings X Sports Bar in Oakland.

Fast-forward to 1999, and Yahoo! Inc. started offering the Fantasy Sports Trade Association, a free fantasy sports system. FanDuel, one of the most popular fantasy football sites today, wasn’t founded until 2009, and in 2011, the second highest-ranking site, DraftKings, started operation.

Why Fantasy Football Has Taken Off.

Fantasy Football Side Business and How to Make Money Playing Fantasy Football

Participants in fantasy football buy $800 million worth of fantasy football media products each year, including television channels and magazines that provide information about it.

There’s an exploding industry powering the fantasy sports industry. For research, participants watch games, read up about how their favorite players and teams are doing, look at opinions from trustworthy commentators, discuss the sport on forums, and use online mathematical tools to determine the possible outcomes for their leagues.

Fantasy football’s popularity outshines that of other sports for a few reasons. First, it’s easy to follow. There is a wealth of football stats and data out there online, on television, in newspapers, and on social media.

Fans can get information anywhere, anytime, and chat with one another easily through online forums and chat platforms specifically designed for fantasy footballers. Plus, the season is short, lasting for only a few months. Other sports like basketball and baseball, run for much longer and are a larger investment of time.

How to Make Fantasy Football a Side Business.

If you want to make fantasy football as a legitimate side business, you’ll need to get serious. For starters, there are many different websites you can check out and you’ll likely want to have many different games and seasons of varying durations going on at a time, if you hope to generate some serious revenue with the sport.

Above all else – you’re going to need some extreme domain expertise in what’s going on with players, teams, and league politics. That means researching, making insightful decisions based on data and real-life events, and planning for if-then situations that will inevitably come up throughout the season.

Making Fantasy Football a Profitable Side Business

The number one site for fantasy football right now is FanDuel, where you don’t have to commit for a full season. To get started, you choose a one-day contest, pick your team, and then earn instant payouts if you win. There are thousands of leagues to choose from, and different entry fees and prizes. You can enter as many games and teams as you want, to increase your chances of winning.

DraftKings is similar to FanDuel, in that you don’t need to enter for the season. It offers various contests, including ones called “Head-to-Head,” where the winner takes all, and “Multipliers,” where you can win 3 to 10 times the amount of money you paid to enter the game.   

To play fantasy football through CDM Sports, all you have to do is register, create your roster, and attempt to rack up stats. The site offers budget games, where you pay less than $2.50 per week to participate. For $14.95, you can have the chance to win up to $5,000.

Real Time Fantasy Sports, like CDM Sports, requires you to register before the season starts. You can play in a 12-team league throughout the season for $29.95, and receive $200 if you win. To go for a bigger prize, the website offers “King of the Mountain,” a contest in which your team must finish in the top 2/3’s of teams every week. If you’re the last one left at the end, you win $25,000.

Resources for Researching Fantasy Football Stats and Topics.

The best players out there don’t bet using their pure instincts. Instead, they do research, utilize mathematical formulas, predictive models, and line-up optimizers to win.

The first thing you must do, of course, is actually watch the games. If you don’t have time for that, watch ESPN Video for game highlights, and keep up-to-date with the news on Bleacher Report.

Playing Fantasy Football as a Side Business

If you don’t have a forum on your fantasy football league, join one online. On these forums, you can discuss opinions about the football players, hear about other fantasy football players’ strategies, and seek out actionable advice from seasoned professionals. You can start conversing at The Huddle Forums or

If you want to pursue a more precise method for daily fantasy football predictions, try an NFL Lineup Optimizer. Another site, Fantasy Football Analytics, allows you to input your data and receive projections for your teams.

The Legality of Fantasy Football.

Unfortunately, you can’t play fantasy football and win money if you live in Arizona, Arkansas, Louisiana, Montana, Iowa, Tennessee, or Washington. Nevada recently ruled that fantasy football is gambling, and requires websites to retrieve gambling licenses if they want to stay in operation. New York has banned DraftKings, FanDuel, and other daily fantasy sports sites from the state. However, DraftKings and FanDuel are both trying to fight this ruling.

If you win money playing fantasy football, you must report your earnings to the government (as with any legitimate side business). You need to report it as miscellaneous income if you win more than $600 throughout the course of a year. The good news is that you can deduct the entry fee from your total annual income. That means if you paid $100 to enter a game in which you won $1,000, you’ll only have to pay taxes on $900 of the winnings, your net positive income.

Before you start any new side business, it’s crucial to look at all the legalities behind how it operates, and we encourage you to do more research before jumping in and making it a serious pursuit. Though fantasy football may sound like a fun hobby, you really can earn a healthy side income from it, and get well on your way to saving up toward launching a more scalable self-employed career in the near future.

Looking for more ways to start a profitable side business? Check out Money & Business For Creatives with Ramit Sethi and get started today.

Kylie Ora Lobell FOLLOW >

Kylie Ora Lobell writes for brands, blogs, and print publications. She covers content marketing, digital marketing, and runs Kylie's Tips for Writers, a blog about writing.