Letter to My Younger Self

Dear Kimbo,

You’re growing up in the Cutler Ridge section of Miami and life will not be easy. That being said, the community and stock you come from — specifically your amazing mother — will shape who you are and lead to success. You’ll eventually become one of the most-watched people on the Internet, and, at its height, your viral popularity will be mentioned up there with Michael Jackson, Michael Jordan and Mike Tyson — more on that later though.

First, we have to go back to where it all began. The most reckless part of your career will also be your foundation. Street fighting is dangerous. It’s not sanctioned, it’s simply guys who can fight who also live in the same neighborhood going at it. The risk is always there. What if you see your opponent in the streets and he’s a bit upset about the L you gave him weeks ago? What if you’re with your kids in the store and you see this dude again? It could be a real issue and turn into a real dangerous situation. I wouldn’t recommend street fighting today, but back then, it was necessary.

People in the hood will respect your dedication and love for these fights. You’ll become an inspiration for people. They’ll say, “If Kimbo can do it, it can be done.”

Once you do begin to pick up steam, if you really want to be a fighter, then get professional training and get into an organization. Do it the right way. In the cage, you don’t have to deal with the animosity that comes with non-sanctioned fights held in someone’s backyard. In those fights, someone can pull out a gun and take it to another level — that sort of thing happens.

Also, when you start getting fame from the tens of millions of people watching your videos on the Web — specifically on YouTube — find out a way to get paid for it. Please. Your fame can be monetized, and you’re the one risking it all by putting your body on the line, so please figure out the business side of it.

When you make the transition into professional fighting, learn the jiu-jitsu game. Jiu-jitsu doesn’t seem that big but trust me, it will be soon enough. Jiu-jitsu is a very important part of the MMA fighting style you will become a part of once you leave street fighting. If you take a great boxer — even the best ones in the world like Mike Tyson or Floyd Mayweather Jr. — and put them in the cage with an MMA fighter who’s well-rounded, that boxer will be demolished. There are so many ways to defeat a boxer in this game, from the Kimura and Americana submissions to the rear-naked and guillotine chokeholds. You have to know these things. And it’s your lack of knowledge in these areas that will result in one of the most confusing and frustrating moments of your career being broadcast live on national TV.

On October 4, 2008, you’ll be scheduled to go up against a fighter named Ken Shamrock. This is a moment you’ve been waiting for. It’s at the Bank Atlantic Center in Sunrise, Florida, so you’ll have some of the home-state love. More than four million viewers will tune in for the fight.

You’re ready for the big lights. You’ve beaten the likes of respected fighters like Ray Mercer and Tank Abbott. However, all I can say is, “expect the unexpected.” At the last minute, Shamrock will suffer an eye injury during warmups … Well, actually, let’s be real: He will get scared and cut himself. Everyone knows it. Since when does someone get injured only hours before the fight during warm-ups? It’ll be a complete bullshit excuse.

Being the fighter that you are, you will still stay on the card and fight a man named Seth Petruzelli — a fighter you honestly know nothing about and have not prepared for. You respect him for taking the fight at the last minute, though. However, as weird as things got in the hours before the fight, they get even more crazy once the bell rings. An awkward kick and punch thrown at the same time is what will stun you and ultimately lead to a first-round TKO.



You won’t look back on the decision to fight Petruzelli with regret. You stepped up to the plate and fought someone who you hadn’t trained for. If anything, this loss will lead to more focus and training, especially when it pertains to your ground game. It will be a tough time, but you’ll build up years and years of resentment toward Ken Shamrock for the stunt he pulled. He’s the reason you lost that fight that night.

Be patient, though. Revenge will come years later.

Outside of the cage, get to know the various business aspects of being a professional athlete. Slow down on your spending. Invest more. Put money into real estate. Don’t second-guess yourself. If it seems like a logical business decision, go for it.

Above all else, your family is the most important thing in your life. By the time you get to my age, you’ll be blessed to have three kids over 18 and three younger ones as well. No matter what they choose to do with their lives, just love, cherish and protect them. Spend time. Talk with them. Pick their brains. Your kids are just another version of you.

Also, don’t quit your day job. I don’t mean that as an insult, but seriously. You can work around your schedule. Still do that. As much as you love the world of fighting, you love being your own boss at Kimbo Security, too. You can do both. You work security for adult entertainers and kick ass in the cage? I can’t make this type of stuff up.

When you start in MMA, you’ll have little-to-no ground game. But after a decade of work, you’ll become more dedicated to your craft than ever before. At the same time, a lot of the fighters around you will become systematic. You’ll evolve and become a threat to those fighters, and you’ll eventually get your chance to reap the rewards of that hard work.

On June 19, 2015, future you (that’s me) will have the opportunity to take out the aggression against Ken Shamrock that’s been pent up since 2008. He cowered away then, and he has no idea what’s in store for him. I’ve been holding this in for years. Now, the waiting is over. My ground game back then was not up-to-par like it is now. My goal back then was just to punch him and get the KO. He had a 50-50 chance of beating you then, but now, there’s no way he can beat me. I have evolved. I can still knock out his lights out, though. I can still break his bones. There’s no way he will win this fight at all. It’s been a long time coming.

You take care of your business, and I’ll have fun scratching that seven-year itch,

Kimbo