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6 BUSINESS LESSONS 
FROM MORE THAN 8 YEARS OF 
F A N T A S Y 
F O O T B A L L 
ROSS SIMMONDS | WWW.ROSSSIMMONDS.COM
Have you ever thought about how our 
hobbies can serve as teaching tools for 
the skills we apply to our every day and 
professional lives?
Consider a ballerina, for example, 
who learns discipline and hard work 
through hours of practice and 
rehearsal before a live performance.
Or a gamer, who is taught how to gather 
information and solve problems while trying 
to reach the next level in a video game. 
+
For years now, I’ve had a big passion for football. 
In fact, that’s exactly where my obsession with 
social media and technology all started.
I first got involved with Fantasy Football 
during University when I ran a profitable 
blog that ultimately led me on a path to 
entrepreneurship and technology. 
$ $ 
I’ve been a Fantasy Football junkie ever since.
It’s estimated that... 
19 million people 
compete in 
Fantasy Football 
every year.
Studies show that $1.1 
Billion is lost in productivity 
every week of the 17 week 
NFL Season because of 
Fantasy Football.
I believe that while productivity might 
take a hit, there are some quality business 
lessons that can be taken from 
Fantasy Football.
BUSINESS LESSONS IN 
FANTASY FOOTBALL 
Know When to Hold’em, 
Know When to Fold’em 
Never Bench Your Studs 
Remove All Personal Bias 
Identify Potential Issues 
Before They Arise 
Every Week is a New Week 
Be Willing To Take Risks
KNOW WHEN TO HOLD’EM, 
KNOW WHEN TO FOLD’EM 
In fantasy football, you take part in a draft before the season 
to build your team. If, as the season progresses, one of your 
players isn’t living up to expectations or gets injured, you 
must decide to wait and let them shake the rust, or 
trade/drop them before the damage is done.
KNOW WHEN TO HOLD’EM, 
KNOW WHEN TO FOLD’EM 
While in Fantasy it’s often easier to just keep the player, in 
business the stakes are a lot higher and, thus, waiting on 
something, or even someone, that might not pan out could 
result in the loss of dollars and/or your business.
KNOW WHEN TO HOLD’EM, 
KNOW WHEN TO FOLD’EM 
The idea of “hire slow, fire fast” has become a mainstream mantra 
for many entrepreneurs, consultants and professionals. It’s a great 
philosophy to live by and one that you should embrace but have 
the processes in place to know when you can invest in someone 
or something and when you need to walk away.
NEVER BENCH 
YOUR STUDS 
When you’re looking for a win in Fantasy Football, it’s much better to 
play a future hall of famer who hasn’t played well the last two weeks 
than it is to play a no name on a hot streak. 
Likewise in business, you must do whatever it takes to keep your top 
talent passionate, engaged and motivated to achieve success.
NEVER BENCH 
YOUR STUDS 
A star will perform best when he/she is: 
1. challenged 
2. given freedom, and 
3. surrounded by intelligent people 
You never bench them. The studs on your team need to be 
celebrated, invested in and rewarded.
REMOVE ALL 
PERSONAL BIAS 
In Fantasy Football, you come up against an internal battle, 
especially on weeks when your starting quarterback is up against 
your favourite NFL team. 
Business is a place where relationships must be put on the 
backburner in the name of good business and success.
REMOVE ALL 
PERSONAL BIAS 
Internal conflicts will arise in the workplace and, to get 
through it, personal feelings must be removed and 
candidness must be embraced.
IDENTIFY POTENTIAL ISSUES 
BEFORE THEY ARISE 
In Fantasy Football, when difficult situations arise, like 
all of your players having overlapping weeks off, or 
horrible playing conditions during playoffs, you need to 
be able to make trades and moves that put you in a 
good position for the rest of your season.
IDENTIFY POTENTIAL ISSUES 
BEFORE THEY ARISE 
Far too many businesses focus on right now rather 
than next week. They don’t plan ahead and are 
resultantly caught by surprise when they don’t get 
the results they hoped for.
IDENTIFY POTENTIAL ISSUES 
BEFORE THEY ARISE 
It’s important to always be thinking 10 steps ahead to ensure you 
have your bases covered. Don’t get caught red-faced with a 
problem that could have easily been avoided.
Week 
10 
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. 
As soon as you feel relaxed with your Fantasy Football team, 
you need to start to panic.
Week 
10 
EVERY WEEK 
IS A NEW WEEK 
Likewise in business, the moment you become content with 
your own skills is the moment you will start to settle. 
Every week is a new week with the same chance at winning and 
making your team better. And every day is a new opportunity 
to be better than the person you were yesterday. 
Take advantage of it!
The last yet most important lesson from Fantasy 
Football is the importance of taking risks. 
Sometimes you need to ignore the status quo 
and do something that is against the norm.
RULESRULES 
You need be willing to break rules and be 
comfortable with the fact that some people 
are going to call you nuts.
You might fail. 
You might succeed. 
You’ll only know if you try. 
SUCCESS 
FAILURE
Instead of sitting on the sidelines, 
take a leap and build your wings 
on the way down.
And who knows…Maybe it will lead 
to a championship.
@TheCoolestCool 
www.rosssimmonds.com

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Six Business Lessons From 10 Years Of Fantasy Football

  • 1. 6 BUSINESS LESSONS FROM MORE THAN 8 YEARS OF F A N T A S Y F O O T B A L L ROSS SIMMONDS | WWW.ROSSSIMMONDS.COM
  • 2. Have you ever thought about how our hobbies can serve as teaching tools for the skills we apply to our every day and professional lives?
  • 3. Consider a ballerina, for example, who learns discipline and hard work through hours of practice and rehearsal before a live performance.
  • 4. Or a gamer, who is taught how to gather information and solve problems while trying to reach the next level in a video game. +
  • 5. For years now, I’ve had a big passion for football. In fact, that’s exactly where my obsession with social media and technology all started.
  • 6. I first got involved with Fantasy Football during University when I ran a profitable blog that ultimately led me on a path to entrepreneurship and technology. $ $ I’ve been a Fantasy Football junkie ever since.
  • 7. It’s estimated that... 19 million people compete in Fantasy Football every year.
  • 8. Studies show that $1.1 Billion is lost in productivity every week of the 17 week NFL Season because of Fantasy Football.
  • 9. I believe that while productivity might take a hit, there are some quality business lessons that can be taken from Fantasy Football.
  • 10. BUSINESS LESSONS IN FANTASY FOOTBALL Know When to Hold’em, Know When to Fold’em Never Bench Your Studs Remove All Personal Bias Identify Potential Issues Before They Arise Every Week is a New Week Be Willing To Take Risks
  • 11. KNOW WHEN TO HOLD’EM, KNOW WHEN TO FOLD’EM In fantasy football, you take part in a draft before the season to build your team. If, as the season progresses, one of your players isn’t living up to expectations or gets injured, you must decide to wait and let them shake the rust, or trade/drop them before the damage is done.
  • 12. KNOW WHEN TO HOLD’EM, KNOW WHEN TO FOLD’EM While in Fantasy it’s often easier to just keep the player, in business the stakes are a lot higher and, thus, waiting on something, or even someone, that might not pan out could result in the loss of dollars and/or your business.
  • 13. KNOW WHEN TO HOLD’EM, KNOW WHEN TO FOLD’EM The idea of “hire slow, fire fast” has become a mainstream mantra for many entrepreneurs, consultants and professionals. It’s a great philosophy to live by and one that you should embrace but have the processes in place to know when you can invest in someone or something and when you need to walk away.
  • 14. NEVER BENCH YOUR STUDS When you’re looking for a win in Fantasy Football, it’s much better to play a future hall of famer who hasn’t played well the last two weeks than it is to play a no name on a hot streak. Likewise in business, you must do whatever it takes to keep your top talent passionate, engaged and motivated to achieve success.
  • 15. NEVER BENCH YOUR STUDS A star will perform best when he/she is: 1. challenged 2. given freedom, and 3. surrounded by intelligent people You never bench them. The studs on your team need to be celebrated, invested in and rewarded.
  • 16. REMOVE ALL PERSONAL BIAS In Fantasy Football, you come up against an internal battle, especially on weeks when your starting quarterback is up against your favourite NFL team. Business is a place where relationships must be put on the backburner in the name of good business and success.
  • 17. REMOVE ALL PERSONAL BIAS Internal conflicts will arise in the workplace and, to get through it, personal feelings must be removed and candidness must be embraced.
  • 18. IDENTIFY POTENTIAL ISSUES BEFORE THEY ARISE In Fantasy Football, when difficult situations arise, like all of your players having overlapping weeks off, or horrible playing conditions during playoffs, you need to be able to make trades and moves that put you in a good position for the rest of your season.
  • 19. IDENTIFY POTENTIAL ISSUES BEFORE THEY ARISE Far too many businesses focus on right now rather than next week. They don’t plan ahead and are resultantly caught by surprise when they don’t get the results they hoped for.
  • 20. IDENTIFY POTENTIAL ISSUES BEFORE THEY ARISE It’s important to always be thinking 10 steps ahead to ensure you have your bases covered. Don’t get caught red-faced with a problem that could have easily been avoided.
  • 21. Week 10 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. As soon as you feel relaxed with your Fantasy Football team, you need to start to panic.
  • 22. Week 10 EVERY WEEK IS A NEW WEEK Likewise in business, the moment you become content with your own skills is the moment you will start to settle. Every week is a new week with the same chance at winning and making your team better. And every day is a new opportunity to be better than the person you were yesterday. Take advantage of it!
  • 23. The last yet most important lesson from Fantasy Football is the importance of taking risks. Sometimes you need to ignore the status quo and do something that is against the norm.
  • 24. RULESRULES You need be willing to break rules and be comfortable with the fact that some people are going to call you nuts.
  • 25. You might fail. You might succeed. You’ll only know if you try. SUCCESS FAILURE
  • 26. Instead of sitting on the sidelines, take a leap and build your wings on the way down.
  • 27. And who knows…Maybe it will lead to a championship.