Brad Gilbert

Supported by Greenhaven Road Capital, finding value off the beaten path.

pablo (24).png

Brad Gilbert won an Olympic medalist, participated on Davis Cup teams, and coached Andre Agassi. In his book Winning Ugly he writes about winning at tennis. The book is really about winning at anything. Let’s see how.

The first step to winning is to not lose. Warren Buffett’s two rules of investing are, one, don’t lose money and two, don’t forget rule number one. Gilbert has similar advice.

“Don’t be afraid to swing at the ball but don’t try to impress the other player.”

“Unforced error determined results more than spectacular shots do.”

“Make sure your mediocre backhand doesn’t make world-class errors.”

“Hit the ball over the net and into the court. Make that the goal.”

“Playing not to lose’ is pejorative commentary. That might be wrong. Athletes, teams, inventors all need chances to win. More chances more winning. Willbur Wright wrote about this:

“The man who wishes to keep at the problem long enough to really learn anything positively must not take dangerous risks. Carelessness and overconfidence are usually more dangerous than deliberately accepted risks.”

Or as Jason Calacanis said about angel investing:

“What makes the great investors is they can be contrarian, they’re independent. The big cardinal mistake people make when they start angel investing is, they have a three hundred thousand dollar stack and say ‘f-it’ let me put one hundred fifty in this one startup…and soon you’ve blown your whole chip stack. I’ve seen people go through this who were invested in three startups and they quit angel investing.”

To do this well you have to know thyself.

“Don’t ask a skinny dog to fly.”

“Look in the mirror – do you see Pete Sampras?”

What are you really capable of doing, asks Gilbert. If you have a weak backhand, own it. If all you can do is pop it back, that’s fine. Think winning over beauty. This is hard to see in ourselves. We have biases. We’re in too deep. Instead, ask someone how they might defeat you. Gilbert had his coach do some scouting too.

 “Sitting on the sidelines it’s fairly easy to spot a match and see what’s happening; who’s doing what to whom.”

Objectively knowing your skills and weaknesses as well as your opponents allows for mismatches.

“I’ll lose if I go strength to strength. I’m good, however, at working my strengths against my opponents weaknesses.”

Michael Lombardi says that the best NFL coaches “make you play left-handed.” That’s what Gilbert wants too. Advantages don’t always come from your best skill but the biggest delta. The sweetest opportunities are in the largest gaps.

This is all in preparation and the best players plan in the calm.

“When things were getting desperate I had a mental compass that kept me on course and gave me a way to get back in the match.”

“Your body will try to do what your mind tells it to do. In this prematch review, you’re programming your mind to give the body correct information once the match begins and things start happening quickly under fire. You’re setting the course you want to take to arrive at your destination.”

Wesley Gray said that he plans in System 2. “All your (military) training is how to minimize system one errors and try your best to use the system two mentality.” This work will prepare for the storm.

“Psychologically 0-3 seems a lot heavier than it is. It’s still just one break.”

“You have to recognize it (anger) and you have to be able to regain control or it’s like playing with a broken racket.”

“My game didn’t fail me (against Connors). My mind did.”

“If you gang up on yourself there will be two people on the court trying to beat you.”

Tennis is a mental game too. Ken Fisher thought that John Templeton was a great investor because of his stability.

“His spirituality led him to a form of internal calmness that’s rare. He would make investment decisions other people wouldn’t make because he was so at peace with himself.”

Learning all this  requires paying attention.

“Who’s doing what to whom? Have at least a sense of it.”

 “After that (an unexpected loss), I started writing things down. It’s when I started my little black book.”

“I’d watch a match like I was studying for a history test.”

Gilbert wanted to find patterns in play. “Pressure,” he wrote about tight situations, “is the ultimate lie detector.”  What someone did when a point, game, or match was on the line carried weight.  This is the same attitude for finding secrets or gems.

“Most of the time there is a way to win. You just have to figure out what it is.”

I’ve never played tennis beyond a few summer afternoons with a wooden racket and Gilbert’s book isn’t really about tennis. It’s about everything. Knowing your limits but getting better. Being curious and writing discoveries down. Accepting luck, innate talent, and harnassing ambitions.


Thanks for reading. I’m mikedariano.

6 thoughts on “Brad Gilbert”

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.