Over the course of my lifetime, apart from episodic deviations for cars, I had two primary goals: first, to raise four kids who are joyful, productive, and socially responsible; second, to empower people to change the world. Here are the experiences that led me to these goals.

1. Honor Counts

Back in the late 1980s, America Online began life as AppleLink Personal Edition, an Apple-labeled online service for consumers that Apple contracted Quantum Computer Services to create. However, Apple blew up this contract for unknown reasons—if nothing else, this proved that Apple wasn’t omniscient, as AOL went on to become a massive success.

On the day that Apple ended the Quantum relationship in 1989, I had dinner with Steve Case, the founder of Quantum, and his team. They were in a state of shock and down in the dumps. But I told them that Apple’s decision could be the best thing that ever happened to them, because they were now free to create an independent company.

Out of desperation more than anything else, Case asked me if I would do some consulting and online conferences for $2,000 per month, plus stock options. I agreed, and for the next few months I helped out, until my contact at AOL stopped asking. I saw Case several years later, and he asked me if AOL was still paying me and had given me the stock options. I told him I hadn’t done much work, so the company wasn’t paying me, and I had never gotten the stock. I told him to “forget about it.”

Nonetheless, he insisted that I get the stock, so I received options for two thousand shares. The stock split several times and the per-share price rose like a rocket, so these options became my version of the proverbial two fish and five loaves of bread in the Bible.

To put this into perspective, I made approximately $250,000 from Apple stock over my career. So I could make the case that the company I did the most work for provided the least money, and the company that I did the least work for provided the most. The only reason I made any money from AOL stock is that Case was an honorable person; he did not have to grant me those options. There was no legal paperwork that proved he ever offered them to me in the first place.

Here’s another story of above-and-beyond honor. This time the honorable guys were Patrick Lor and Bruce Livingston, the cofounders of iStockphoto, a Calgary company that sold stock photos at one- twentieth the price of companies like Getty.

I met Lor at the September 2003 Banff Venture Forum, where I was a speaker. The topic that brought us together was not entrepreneurship, venture capital, or photography. It was ice hockey.

As I am prone to do, I diverged from the topic of my speech to discuss my passion for hockey—what better way to bond with a Canadian audience? I mentioned that I had visited the Graf factory in Calgary the day before and ordered a pair of skates. Nike had given me a pair just before I left my home for Calgary, so I now had an extra pair.

In the middle of my speech about entrepreneurship, I mentioned this extra pair and asked if anyone wanted to buy them. Years later, Patrick told me that he really didn’t need the skates nor did he have the money to purchase them, but he bought them as a way to meet and talk with me at the conference.

We spoke about more than just the skates that day, and he asked me to join his company’s board of advisors. I agreed, but we never came to a formal agreement because of the complexities of Canadian law. Regardless, I evangelized the company for several years.

Getty eventually bought iStockphoto for $50 million (US). Patrick and Bruce made more money than they ever dreamed possible, and they contacted me with the question, “How much stock should we have granted you if we had a formal deal?”

My answer was that a typical advisor would get 0.5 percent for a role such as advisor, spokesperson, or window dressing. I did all three. And what did Patrick and Bruce do? They paid me 1.5 percent of the purchase price from their share of the deal! That was another chunk of money I never saw coming.

As this and the Steve Case story show, I made out just fine without formal contracts. A logical question is, “Why did these two situations turn out so well?” Several reasons:

  • I’m a lucky guy.
  • I was usually in a position of power and visibility, so it would have been dumb to shortchange me.
  • They were honorable people.

Wisdom: Do the right thing. Be a Steve, Patrick, or Bruce. A formal contract with a dishonorable person is worth less than an informal contract with an honorable one. These guys taught me about honor when honor meant giving up hundreds of thousands of dollars.

 

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2. Humility Rocks

In 2008, Richard Branson and I spoke at a conference in Moscow, Russia. This was the first time we met. We were in the speaker prep room, and he asked me if I flew on Virgin—which is what you would expect him to ask. I explained that I was a Global Services–level United Airlines customer—which meant free automatic upgrades and other VIP services (but not repayment of taxi fares). No one except United employees knows what it takes to achieve this exclusive status. Reaching it is not as simple as accumulating lots of miles.

 I explained to Branson that I didn’t want to jeopardize my Global Services status by flying on other airlines. Then Richard Branson dropped to his knees and started polishing my shoes with his coat. That was the moment I decided to start flying on Virgin America. (I never saw Steve Jobs get on his knees to get a customer.)

Wisdom: Be humble—it will help you succeed. If a billionaire knight who owns an island and kitesurfs with Barack Obama can get on his knees and shine your shoes for your business, you can, too. Perhaps his propensity to do this is why he became a billionaire knight. Skeptics would argue that Richard would do this only for people who are rich, famous, or powerful. But my sense of him is that he would have done this for anyone—he’s that kind of person.

 

3. The World Is a Big Place

This story was in my baccalaureate speech to Palo Alto High School, but it merits repeating and further explanation. I made a mistake in college: I graduated early. I entered Stanford with AP credits, and I took a heavy course load. This enabled me to fulfill my requirements by December 1975, even though the school year ended in June 1976.

I attribute my early graduation to my DAA (Diligent Asian Approach), which involves studying hard and forgoing extracurricular activities that don’t look good on a college application. It’s the philosophy of “start violin at two, enter the Kumon math program at five, take calculus in the seventh grade, and start a nonprofit at fifteen to get into Stanford or Harvard.”

I should have taken the full four years—or even more—to graduate. I regret not attending any of the Stanford overseas campuses or at least traveling outside the United States. Today, at sixty-three, with one wife, four kids, one dog, eight chickens, one job, one brand ambassadorship, one fellowship, and one directorship, I have little desire to travel for pleasure.

The theory of seeing the world as a tourist when you’re an empty-nester doesn’t apply, be- cause my youngest child is thirteen. He’ll be in college in seven years, so I’ll be pushing seventy, if not pushing flowers out of the ground, when he moves out. And by then there may be grandchildren from my other kids, so I won’t want to travel.

Wisdom: See the world when you’re young. The time to do this is when you don’t have a mortgage, car payments, or kids (though maybe student loans). There’s not going to be a better time to travel. I have never met anyone who wished they had started working earlier.

I could also make the case that seeing the world will make you a better employee or entrepreneur. This is why it’s good to travel while you’re young and not wait until you’re mid-career or retired. I predict that you’ll come to three conclusions:

  • People around the world are more similar than they are different.
  • Your life is better than most people’s.
  • Traffic where you live is not as bad as you thought.

 

4. What Are You Going to Tell Your Grandchildren?

In October 2016, I went to Berlin to speak to the marketing staff of Mercedes-Benz. The night before my speech, I had dinner with two German friends, and the conversation inevitably turned to the presidential election in the United States. At this point, thirty days before the election, few people believed Donald Trump would win.

The very fact that Trump was one of the two leading candidates astounded us. My friends told me that they still didn’t understand how their grandparents’ generation could let Adolf Hitler come to power, and they saw direct parallels between Hitler and Trump.

They warned me, “If Trump wins, it will be 1933 for America.” What they meant was that before Hitler was Hitler, he was “just” a popular politician. He didn’t start killing Jewish people and invading countries on his first day as chancellor. This conversation had a profound effect on me. I didn’t  want my grandchildren to wonder if I resisted Trump, so I started using my social media accounts to #resist him. Few, if any, social media influencers took such an aggressive stance at the time.

They didn’t want to go off-topic from their usual subjects such as food, cats, fashion, social media, or entrepreneurship, because taking such a stance might affect their brand and cause them to lose followers. But the fear of losing followers  and business were not a strong enough deterrent for me to keep silent, so I turned my Facebook, Twitter, Google+, and even LinkedIn accounts into political feeds—contrary to the wisdom of so-called social media experts. And guess what?

While a few hundred people complained about me getting political and resisting Trump, the feedback was far and away supportive. I may have lost a few thousand followers, but I gained tens of thousands more. Standing up for what I believe was not only the right thing to do,  it also was a good marketing decision, because my brand was aligned with democracy and meritocracy, not the Trump Reich. However, even if my stance had cost me followers, branding, or income, I would have still done it. That is what I will tell my grandchildren.


Wisdom: Do what’s right. Influence comes with a moral obligation to stand up for your principles and to help less fortunate people. This may come with personal and short-term costs—but that’s what a moral obligation entails.

 

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5. The So-What? Test

If you let it, drama can fill your life. My experiences have led me to conclude that trying to eliminate drama is futile—what is important is how you react when drama occurs.

For example, when I joined the board of a nonprofit organization, we experienced drama every week when some part of the organization’s employees and customers didn’t like a board decision.

The sequence was that we would make a decision and then several dozen employees or customers would freak out, then the board would freak out that employees or customers freaked out and rush to try to appease them (never succeeding), then another drama would occur and the cycle would start again. This happened once a month for my entire tenure. The reason the board freaked out is that they imagined apocalyptic, worst-case, or at least bad-case, scenarios: employees would quit, employees would strike, customers would abandon us, and the New York Times, the Wall Street Journal, and the Washington Post would write a front-page exposé. None of these things occurred.

From this experience, I derived the So-What? Test. It means when drama occurs, you ask yourself, “So what?” For example, your daughter got a C on a math test. So what? She won’t have a 4.0 GPA. So what? She  won’t get into Dartmouth. So what? She will not succeed in life. Really? Getting into Dartmouth determines the outcome of her life? I don’t think so.

Wisdom: Ask, “So what?” This may not help prevent or avoid problems, but it will help put “crises” into perspective, and perspective is everything if you want a joyful and productive life. This doesn’t mean you shouldn’t work hard, but if everything doesn’t go as planned, ask yourself, “So what?” a few times and see if it matters.

 

This story is an excerpt from Guy Kawasaki’s new book “Wise Guy – Lessons From a Life” released in February 2019. Find it on Amazon.