In this book, LOL stands for Laugh-Out Lessons. These are the funny things that happened to me – or that I caused. There is humour in these stories, but they also embody interesting, and important, life lessons.

Simplest Is Best

Here are three anecdotes that illustrate the concept that simplest is best.

(1) In 2016, I was on the board of trustees of the Wikimedia Foundation, and I attended the Wikimania conference in Esino Lario, Italy. (Wikimania is the annual meeting for worldwide members of the Wikipedia community.)

Some participants came from countries where the government frowns upon, if not prevents, the free flow of information. Thus, they did not want to be photographed and were able to use a special fluorescent green lanyard to hold their badge to signal this desire.

I saw a woman from a country whose government was in a state of flux wearing one of these lanyards. Later I overheard her say, “I picked the green lanyard because it matches my earrings better.” So much for the assumption that it was a personal safety concern over the fear of government reprisal.

(2) Heidi Roizen is a big-deal venture capitalist and tech guru in Silicon Valley who’s been a friend of mine since 1983. Her father gave her a hard time about driving an expensive BMW. One night she took him to MacArthur Park, a restaurant in Menlo Park.

When they came out of the restaurant after dinner, her car was still in front where she had parked it. She told her father, “Do you see why I drive an expensive car? They leave it out front, and this means we don’t have to wait for the valet to get it.”

A second later, a pissed-off valet came up to her and told her that because she had taken her keys with her, no one had been able to move her car all night.

(3) In September 2017, I received an unexpected Amazon shipment of wart-removal medicine. When I asked Beth about it, she said that she hadn’t ordered it, either, but that she had been doing online re- search about wart removal. Could it be that someone had hacked her computer, figured out she was looking at wart medicine, found our address, and ordered it for us? That was scary – though nonsensical. Hackers don’t order medicine for you.

The next day, I went through the trash and found the box the shipment had come in and saw that it was ordered by someone else named Guy who lived on the same street. No hacking was involved.


Start with the simplest explanation. It’s often the best – this principle is otherwise known as Occam’s Razor. For example, a badge to match the colour of your earrings, a valet who needs your keys to move your car, and an incorrect delivery were all the simplest explanations.

Sinister plots, hacking, and conspiracies are seldom responsible. Stupidity and luck – good or bad – are usually the most likely reasons that something happened, so don’t think too much and don’t be paranoid.

Showing Weakness Is a Sign of Strength

Zatoichi was the name of a blind masseur in a series of Japanese movies. He wandered the countryside minding his own business, but he inevitably wound up righting wrongs with his sword. (Think: blind Japanese Robin Hood.)

I saw many Zatoichi movies when I was growing up in Hawaii. This was before the movie industry was concerned about damaging minors with violence and gore, and I guess my parents reasoned that samurai films were part of our culture.

I survived the cinematic trauma and even learned a valuable lesson. In one movie, as I recall, a criminal gang captured Zatoichi, and the boss of the gang forced him to have sex with a prostitute in front of him and his henchman at a Japanese inn.

The gang members consider Zatoichi to be weak because he agreed to this humiliation, and they laugh their heads off (literally). Then the innkeeper points out that it’s difficult for a man to have sex if he’s scared – in other words, Zatoichi wasn’t scared, so they should be. Shortly after, Zatoichi killed them all.

Fast forward to June 11, 2007. Another samurai, by the name of Steve Jobs, proclaimed at the introduction of the iPhone, “Our innovative approach, using Web 2.0–based standards, lets developers create amazing new applications while keeping the iPhone secure and reliable.”

In May 2008, the samurai’s company issued a press release with this headline: “Apple Executives to Showcase Mac OS X Leopard and OS X iPhone Development Platforms at WWDC 2008 Keynote.”

Let me translate these statements. The first meant that iPhone was a closed system; developers could not create stand-alone apps for it. All they could do was write plug-ins to add functionality via Safari, Apple’s browser on the phone.

The second statement was a complete reversal of the first. Now Apple was permitting and even encouraging stand-alone iPhone apps. Developers went on to create hundreds of thousands of them, and it was these apps that were crucial to the ultimate success of the iPhone.

While Apple’s statements are not as dramatic as sex and decapitations, they illustrate the same concept: strong people can show weakness. Zatoichi was forced to have sex in front of the hoodlums. Steve Jobs had to reverse his position on the closed architecture of the iPhone.


Don’t be afraid to show weakness. Strong people can admit a mistake, change their minds, and tolerate humiliation. Often this is the first step toward building strength.

Weak people are afraid to show vulnerability. They think this gives their competition the advantage or positions them poorly. Strong people don’t see it this way.

When you encounter weakness, flexibility, or the willingness to compromise, don’t underestimate your competition and don’t overestimate yourself.

When you encounter what appears to be strength, don’t overestimate your competition and don’t underestimate yourself. In short, be kind, flexible, and humble when you are in a position of strength. This communicates true power better than brute force does.

Wise Guy

Excerpted with permission from Wise Guy: Lessons from a Life, Guy Kawasaki, Portfolio.