Learning From Success | Floyd “Money” Mayweather

Tldr; Success = A Game of Adjusting + Calculated Risks + Eyes on the Prize & how it applies to business

I think Floyd Mayweather will always be underestimated by the public purely due to the nature of how he fights. He plays safe. He plays patient. And he plays focused. For the instant-gratification-seeking masses, this is not a fun fighter to watch.

As fans, we miss out on the ferocity that we may get from Pacquiao or Tyson, but what we get in return is the best fundamental winner of all time (imo). Let’s shine the microscope on a couple of those fundamentals and see how they can apply to the business world.

A Game of Adjusting

I think what Floyd understands about the game of boxing and the game of winning in general is that it’s about adjusting, reacting, listening… and then acting.

I think what a lot of people do, whether it’s boxers, businesspeople, or even gamers, is they try to set a strategy beforehand. They come out of the gate and they’re either swinging freely, holding back a bit, or just executing on whatever strategy they set for themselves.

What Floyd does very well is he doesn’t have any strategy other than watching what his opponent is trying to do and adjusting accordingly.

The way I see this applying to business is when entrepreneurs are able to create products without being attached to their creative vision. So when your product goes live, it’s like you stepping into the ring with your opponent. Whatever you believed about your opponent before stepping into the ring, now you play the game of listening and adjusting.

Calculated Risks

Never bet the farm on one delicious opportunity.

I love watching Floyd in his first few rounds. His opponent usually comes out with the mindset, “I won’t be able to beat him on the defensive game so I need to knock him out in the first few rounds.”

These first few rounds, Floyd is widely considered a boring fighter. He sits back, focuses most of his game on protection, and waits for small openings to land a strong punch.

Look through any of Floyd’s past fights and watch his punches in the first few rounds. They’re all counter-punches based on openings he finds in the opponent’s stategies.

Oftentimes, he loses the first few rounds.

Even at his current age, Mayweather is arguably in the best shape out of any boxer in the ring. So he absorbs the punches and waits for his opportunity in the later rounds.

For me, I see this as an ideal model for company growth. When you just start a company, you have many vulnerabilities. The industry giants may use their money and influence to squash you before you even have a chance, your timing could be off, or you can’t find product market fit and run out of runway.

So when you first step into the ring, protect yourself and systematically eliminate risk with any bit of capital that you have.

As you grow start peeling back the defensive strategy and start looking to go on offense, taking jabs at the market only when you see a clear opening.

As you get into your power, you will be able to take bigger and bigger risks that can have bigger and bigger payouts. However, never forget the cardinal rule: never bet the farm.

When you have a robust structure that you’re sitting on, ask yourself how much you could bet on a new project or a new investment without risking everything and going to 0.

Eyes on the Prize

If you go back and look at any of Mayweather’s tapes, I recommend looking at how few punches he takes, but where those punches land.

He knows the sweet science of boxing: hit and don’t get hit. So his opponent may land 2 jabs to the body, slightly catch him in the jaw, and then miss 5 times. However, during one of those misses, Floyd delivers one uppercut to the head.

Floyd won. He knows that boxing is a long game of attrition so he’s not worried about any tiny losses here and there, as long as he can get the big win.

Go watch him and watch his extreme focus. He never takes his eyes off of his opponent and no matter what happens mid-fight, he always stays focused on what’s important — dodging big hits and landing big hits..

For business, I think the lesson here is understanding what your core competency is, and never letting anyone or anything take your focus away from it.

I think Uber has done this extremely well. Uber knows they’re the best in the world at mapping and pricing cars efficiently. So when Lyft entered into the market and started paying customers to use their inferior product, Uber could have been tempted to play the marketing game too. Instead, they’ve put almost all of their money back into their core competency and setting up a smaller scale marketing campaign to remain competetive in that department.

As a result, they’ve built a far superior product than Lyft, and they have a robust piece of technology that they’re sitting on rather than tons of wasted marketing dollars.


There’s a lot of talk about working hard vs. working smart. I think what Floyd Mayweather does best is he trains furiously on improving his intangibles — speed, reaction, adjustment, focus, etc. — so that when he’s in the ring, he is able to think and fight on a different level than his opponent. Work hard and smart, bitch!