Wynn-ing Ways: Winning Marketing Strategies to Conclude an Epic Season One

So, where are you after reading this series?

Have you determined what your Wynn-ing Way forward will be?

The psychology of marketing

I’ve got one last story for you this season. It’s about a guy named Amarillo Slim.

Amarillo was a cowboy gambler and an original personality in Las Vegas.

If you want the full details on him and his stories, you can get a copy of Amarillo Slim in a World of Fat People. This is one of the books I read for next season.

If Slim made a bet, it was already won.

You see, he didn’t leave things to chance. In some respects, he was a bit of a con man. Words mattered when you agreed to a bet with him.

This story starts with Amarillo making a bet with Bobby Riggs, a notorious tennis hustler and the 1939 Wimbledon Champion.

Slim didn’t like to sucker just anyone. He wanted to sucker champions—those that were un-suckerable.

Now Slim knew he didn’t have a chance in a straight-up tennis match against Riggs. While he liked rackets, he’d never been much for courts. To make matters worse, Riggs was a hustler who had won tennis matches with poodles tied to his legs or while holding an open umbrella.

They finally agreed to play ping-pong on the condition that Slim got to choose the paddles. Bobby agreed, as long as the paddles were identical. The bet was set, and money was posted for a match in thirty days.

On the day of the match, Slim pulled two cast-iron frying pans out of his bag.

The result was Slim won, 21-8.

Slim had been practicing for months playing table tennis with a pan since he saw Bobby Riggs play Billie Jean King in the battle of the sexes.

The funny thing was this wasn’t the first time Slim had set up a champion. Ego had led a champion to step into one of Slim’s proposition bets yet again. Slim used their behavior against them. The Soviet KGB called this “reflexive control,” and Slim knew its power well.

table tennis 1708418 1280

This story is just getting started…

News of the Riggs match got out, as Slim knew it would.

A few months later, he was in Tennessee at a poker game. There were some wise guys there, and one named Lefty (I can’t confirm if it was Lefty Rosenthal) said he had a guy who could beat Slim at table tennis.

“Not if I can pick the paddles,” said Slim.

“My friend will be here in a couple of days,” replied Lefty.

“Well, I’m going to do a bit of fishing after I bust these poker players. If he wants to play me, let me choose the paddles, and he’s got a game.”

“What if he’s a good player?”

“I don’t give a damn if he’s a good player or an aviator. If I get to choose the paddles, we’ll play.”

A few days later, when Slim got back, he met Lefty’s ringer. A professional table tennis player from Taiwan.

“Let’s get it on,” said Lefty.

“No. Let’s post our money and play thirty days from now. I need a little practice now that I see you got yourself a real-life ping-pong champion.”

Now, “posting the money” means both parties give the cash to a neutral third party. If Slim failed to show up thirty days later, Lefty would get the money, no-contest. (And yes, by the end of season two, you’ll be up on all the gambling and grifter slang.)

The day before the match, Slim got word that the ping-pong champion was seen playing with a skillet and had mastered its use.

On match day, every rounder, hustler, and wise guy was there. Slim recounts there were eleven private jets on the tarmac. Besides his bet with Lefty, he took anyone’s money that would bet him at even money. Then, he took bets at 6:5 (meaning he would pay $6 for every $5 bet if he lost).

After all the betting was done, the match was to begin. He walked over to a soda machine and put in ten cents. He selected a bottle of Coca-Cola. He then repeated the act to get a second Coke. He opened both and poured out the contents.

He walked over to the Taiwanese champion.

“Pick your paddle.”


“Yeah, these Coke bottles are our paddles. Have your pick? I’ll even give you a choice—to serve or return first.”

Slim beat the ping-pong champion 21-0.

Slim knew that someone would like to teach him a lesson after the Bobby Riggs bet. Every step of the way, he set the stage to win the bet and do it on an epic level.

The bet wasn’t who could win ping-pong playing with pans but that he could beat anyone if he picked the paddles.

Slim had been practicing ping-pong with a Coke bottle well before his first meeting with Lefty.

He knew he could have beat the champion when he first learned who he would play. He had already had enough practice serving a ping-pong ball with a Coke bottle. He purposely pushed it out so Lefty would tell all his goodfellas about how he had Slim in a squeeze. They all wanted to be there to win money from Slim.

Lefty and his champ would only get more confident as the athlete practiced with his skillet.

Slim knew Lefty would get greedier, and the champ would get worse, as the skillet was heavy and rough with a flat surface. They would be playing with a smooth, lighter, rounded “paddle.”

When you patiently and deliberately design outcomes and turn probabilities in your favor, you win before the game is played.

Slim was a natural at slow-cooking a mark. He’d thought through not just winning the first bet to teach Bobby Riggs a lesson, but he knew someone would try to win playing ping-pong with a skillet, and that guy would lose even more money.

How did he know it would work?

Because of human nature. Grifters and hustlers are PhDs in psychology. They learn how people behave in pool halls and the hardscrabble streets where they ply their confidence games.

Why don’t most authors have the optimal business system?

Because they don’t do the work to get the outcomes, and they don’t have the patience. They focus on ego or sales rather than a long-term business outcome.  They haven’t developed Wynn-ing Ways.

Slim didn’t know who the big mark would be after Riggs; he just knew there would be one, and he had a plan. This wasn’t the first time. As a pool hustler, he had learned how to set the honey pot for a big win.

Final thoughts

Envisioning this big, profitable, optimized, anti-fragile publishing business can get overwhelming. It might seem like it’ll never happen. Start taking small steps today and patiently set yourself up for as many positive probabilities as you can, and someday, it will all fall into place.

You’re not pulling off some scam to sell some books. Instead, you are writing books that satisfy a substantial unmet market desire and delivering them to that market.

This concludes season one.

I appreciate the attention you’ve given me throughout this series, and I hope you came away with inspiration to find your Wynn-ing Ways.

Joining us in season two will be Amarillo Slim, cult leaders, one of Chicago’s most notorious swindlers, and the father of propaganda. Tune in to hear how you too can play the big con on the publishing market.

And if that’s not your game, remember, if you sit down to play at that table and can’t identify who the sucker is, guess who’s the sucker?

Let me show you how to be the one setting up the market for the big score rather than a mark.

Up next: Season 2