6 Business Lessons from 8 Years of Fantasy Football


Never Bench Your Studs | Fantasy Football

What many people don’t know is that my obsession with social media and technology all started with Football. It was my first year of University and because things like Facebook didn’t exist, I procrastinated by writing a daily Fantasy Football blog for SportingNews.com. In fact, my blog brought quite a bit of success and generated a loyal following. After about a year of blogging about Football and helping people all over the world win their first championship, I decided to start a business from it.

I integrated my blog with an eCommerce platform selling Football Memorabilia and had enough to cover tuition for two more years. To be blunt, I’ve been a Fantasy Football junkie ever since and have learned a lot along the way. Many of the lessons I learned through this journey I’ve applied to my marketing and entrepreneurship career.

Here are some of the most important insights and tips I’ve learned over the last few years from playing Fantasy Football. Use these insights wisely and take your business to the next level while start getting closer to achieving success.

Know When to Hold’em, Know When to Fold’em

In Fantasy Football you go through a draft before the season begins to build your team. You instantly feel a connection to these players because you chose them over hundreds of other players in the league. For me, I put a lot of effort into my pre-season and make sure that my choices are well thought out and always strategic. Once in a while however, you draft a player who doesn’t live up to your expectations and you have to make a decision:

  1. Wait and let them shake the rust or
  2. Trade/Drop them before the damage is done

More often than not, it’s easier to just keep the player and keep your fingers crossed. In business, the stakes are a lot higher and thus, waiting on something that might not pan out could result in the loss of dollars and/or your business. If you have an idea that you’re pouring your heart and soul into and are simply generating no traction, no revenue, no results and no interest – It might be time to fold’em. If you have any of the above then you’re in luck cause there’s a reason to hang on. The same issue arises with talent, if you’re trying to build something amazing you need not worry about your team – If there isn’t a good fit, cut them. Trust me, it’s definitely worth it.

Never Bench Your Studs

When you’re looking for a win do you put in a no name on a hot streak or a future hall of famer who hasn’t played well the last two weeks? Always go with the latter. It’s more likely that your overnight celebrity puts up a goose egg than it is to see a repeat of a disappointing week from a top caliber player. Often in Fantasy Football we’ll play too much attention to the media and match-up and as a result bench our first round draft picks. Very rarely does this approach not bite you in the backside.

In business you do whatever it takes to keep your passionate, top talent. In fact, once you’ve given everything but the kitchen sink for this talent you need to identify the importance of keeping them motivated and excited to play. A star will perform best when (1) she’s challenged (2) is given freedom and (3) is surrounded by people who are just as, if not, smarter than they are. From there, you never bench them. The studs on your team need to be celebrated and rewarded. Will this cause the C-Players or B-Players to get upset? Who cares. Focus on your studs and cut the fat.

Remove All Personal Bias

I’m a huge Philadelphia Eagles fan and when I have an opportunity to draft an Eagle, I draft an Eagle. I once almost traded my entire team for Donovan McNabb (Former Eagles QB) simply because I’m such a fanboy. In Fantasy Football you really do come up against an internal battle especially on weeks when your starting QB is up against your favourite NFL team. I can remember one year having Tony Romo on my team and making the decision to bench him solely because he was playing the Eagles (See Rule #2). That game Tony Romo scored three touchdowns and would have put me into the Fantasy Football Playoffs.

In business you also come across conundrums where internal conflicts arise. For example, you will often find situations where you must put personal feelings towards an individual aside and put the business first. Whether you hate someone you need to work with our like someone you need to fire – business is a place where very often, personal opinions and relationships must be put on the backburner in the name of good business and success.

Smack Talk Must Be Used Sparingly

Fantasy Football Meme

The gift of gab is definitely something I have used on a regular basis to get in the head of my opponents in Fantasy Football. In fact, the gift of gab has been something I’ve used throughout my entire life when it comes to sports or any type of competition. The thing about smack talk is that there’s a thin line between being funny or poking fun and taking mean jabs and sparking fights. Not going to lie, in Fantasy Football ~ it’s no hold bars. In business however, smack talk should be minimal.

There are many organizations, CEO’s, and professionals who think it’s cool to berate and rip into colleagues or competitors. While we can look at Ari Gold for Negotiating tips, he’s far from someone you would look up to for inter-office relationship advice. He’s built his reputation for being an asshole and that’s far from an attribute you should strive to develop.

Identify Potential Issues Before They Arise

The NFL Season is 18 weeks long as a whole but 17 weeks long for an individual player (injuries and suspensions excluded). Each team is provided with a week off and this can cause big problems for Fantasy Football if you have 5 players with the same week off. It’s actually the recipe for a disaster week and one that can quickly lead to a line chalked up in the “L” column.

Beyond the fact that players get time off, there is also the Fantasy Football playoffs. The Fantasy Football playoffs just so happen to be during the winter and are in week 14, 15, 16 and 17. If your players are up against (1) Tough teams or (2) teams that play in horrible conditions – This is something that should lead to a red flag. When situations like these come to the surface you need to be able to plan and make trades and moves that put you in a situation that won’t hurt your season.

This idea links back to the importance of planning. At the time of this post, I’m working on a start up dedicated to bringing unique social experiences to awesome people looking for things to do in Halifax. We’re essentially in the business of developing, designing and delivering unique events. When you run outdoor events in Halifax you always have the risk that the weather will make a list minute decision to change on you. Thus, we’re always thinking 10 steps ahead to ensure we have our basis covered.

At the same time, the importance of planning can be seen in a variety of other industries. In the communications industry far too many businesses focus on right now rather than next week. That is, they don’t plan for the fact that a huge marketing initiative could increase the amount of traffic to their site by 500% and exceed the power of their dedicated servers, even with log monitoring in place. Often times companies don’t plan ahead and are caught by surprise when they realize their contest can easily be manipulated to damage their brand.

Every Week is a New Week

While it’s important to plan ahead, you most certainly need to focus on each week and never take your opponent for granted. There are many times when you will feel relaxed because your team has been on a roll and your opponent has been doing horrible. As soon as you feel relaxed over an upcoming week, you need to start to panic. Every week you know your password is a week you have a chance to win and furthermore is a week you have a chance to make your team better. This is how you need to look at your Fantasy Football team and at your business.

The moment you become content with your own skills is the moment you will start to settle. I don’t think I’ll ever settle. I believe that the majority of people don’t reach their full potential and highly doubt that even I will be able to reach mine. Thus, I’m striving to constantly push myself to learn new things and build my skills so when I take my last breath I can say it was time well spent. Every day is a new opportunity to be better than the person you were yesterday and it’s our choice whether or not we want to take strides to make that idea a reality.


As you can see from the insights above, Fantasy Football really is more than just a little game NFL fans play to waste valuable time. The insights above can be applied to any Fantasy Football looking to become successful. In fact, these insights can be applied to any business, organization, non-profit or startup looking to find success.

I do want to point out that another part of success for fantasy football is taking a risk. Sometimes you need to ignore all the traditional rules of the game and do things your way. You need break rules, make people made and have them call you nuts. Only then will you truly be able to find great success and come out the champion.

Know any Fantasy Football tips that can also be applied to business? Or maybe you think you have what it takes to be in the same league as me? I’d love to hear from you below.