Scott Adams is comfortable going out on a limb. One day, 30 years ago, on a whim, he decided to take up cartooning because he was unhappy with his job working in the budget and financial analysis department of Pacific Bell, a phone company. Today, he’s best known as the creator of Dilbert, one of the most recognizable comic strips, which is published online and in 2,000 newspapers in 57 countries. But, that’s just one of the things Adams has been up to in the last 30 years.
He’s written a few books, including one on how he’s gotten to where he is, called How to Fail at Almost Everything and Still Win Big. He invested in the restaurant business. And he even dipped his toe into blockchain with his most recent project, WhenHub, a platform with products to serve freelancers and contractors. It offers services like a software that builds shareable visual calendars and schedules, and a video chat function that can be used to connect consultants with their clients. Payments can be made in fiat currencies or crypto.
But most notably, Adams has emerged as something of a celebrity in conservative internet circles. In 2015, when President Trump announced his candidacy, Adams started blogging about him, citing what he calls Trump’s distinct techniques of communication, which has more than doubled his following on Twitter.
In 2017, Adams published a book about Trump’s mercenary (if idiotic-sounding) linguistic tactics and how to use them to your own advantage. It’s called Win Bigly: Persuasion in a World Where Facts Don’t Matter. Inadvertently—or at least that’s how he describes it—he’s become a popular figurehead for Trump evangelists. And Adams is convincing—just ask his 289,000 Twitter followers, and viewers of his daily Periscope videos, where he talks Trump, politics, and the news of the day.
Adams spoke with BREAKER about his startup, WhenHub, the future of Dilbert, and how his career is holding up after endorsing Trump. Turns out, Adams is something of a mercenary himself.
Are you surprised that Dilbert is still going after almost 30 years?
The surprising part was getting into newspapers in the first place, but once you’re in there and you’ve made an impact, the lasting is actually the less surprising part. The funny thing about comics, at least comics in newspapers, is if you’re successful at all they tend to last 30 years. So it’s a weirdly binary kind of a job you either last like 30 years or you don’t last very long at all.
How has it changed over that time? I know that you’ve mentioned blockchain and crypto in a few recent installments.
The basic setup is always the same. It’s always the people at a big company, but everything from the introduction of blockchain, robotics, artificial intelligence, so there are a lot of topics that are more driven by technical changes. Obviously, the comic has been running for 30 years. So you have to understand that in the beginning, even a picture of a laptop in the comic would have been unusual and there were no smartphones. So yeah, as the fabric of life changes the comic changes with it.
How did you first become interested in blockchain?
It was just something that was in the news and I followed. I knew a few people who got filthy rich, getting in bitcoin early, several of them. I live in the Bay Area, so people tend to jump on stuff earlier. So I wasn’t quite interested enough to get into it myself until the CTO at WhenHub, my startup, mentioned that he had an idea for incorporating it in the product.
Tell me about WhenHub. I know your new product connects people to experts, right?
There’s this enormous gap in trying to figure out how to do stuff, whether it’s business or personal. You can Google just so much, but 10 minutes talking to an expert can can change your life in a way that you just can’t find on Google, and you might not have the resources to hire your own personal consulting. So, we’re looking to fill in that gap. We also have some other products on the platform.
How does blockchain fit into that?
You can pay the experts using our WHEN tokens. There might be a lot of situations where people didn’t want to use a bank, or they don’t have one or they’re in another country and don’t want to pay banking fees.
When did you decide to start writing about Trump?
When I saw him giving speeches, I knew that I was recognizing a technique that would be invisible to other people because in my 20s I trained to become a hypnotist. I started following him, like everybody else in the world. I started getting interested in everything he’s doing, because that’s another part of his gift.
Wait, why did you train to become a hypnotist?
I was influenced by the fact that my mother gave birth to my younger sister while she was under hypnosis. She reports being awake and feeling no pain while having no pain killers. I wanted to get that superpower.
I'm not a conservative, I'm not a Republican. I describe myself as being left of Bernie, but I couldn't ignore his technique.
And that made you more qualified to write about Trump?
I started writing blog posts about it, and by that time he labeled Jeb Bush, “low energy Jeb.” The very same day I blogged that that was the end of Jeb Bush, and it was. I think it was either my first or maybe second blog post about the president, or the candidate back then in 2015. It was one of the most viral things I’ve written, so I thought to myself, ‘Wow, I guess people like that.’ And I get paid for how many people go to my blog, because it’s an advertiser model. I thought, ‘Oh, I’ll write some more of that.’
What makes Trump different from anyone else?
He speaks in a visual language. And if you don’t study persuasion you might just think, well, it’s just sort of a grandfatherly way to make fun. People would just think it sort of a grandfather effect, but it’s not. He’ll talk about the wall instead of just the concepts of immigration. He’ll talk about specific criminals instead of talking about the concept of crime. You know, half of persuasion is making sure that you’re paying attention and you’re not paying attention to the other people. But, I’m not a conservative, I’m not a Republican. I describe myself as being left of Bernie, but I couldn’t ignore his technique.
I know that you describe yourself that way, but I’d assume the vast majority of your followers are Trump supporters.
Well, it makes perfect sense because I write primarily about Trump’s persuasion talents and because he’s good at it. Ninety percent of what I say about him tends to be positive because I’m focusing on the part I know and the part he does well. So, people follow me for that and then I also play to the audience. Because once you have an audience, you know, the temptation—and maybe that’s the wrong word—but let’s say the natural way that these things work is if you have an audience that likes a certain kind of content, you’re more likely to give it to them because that’s good for you and it’s good for them.
I thought that I needed to double down on the side that was working, because I couldn’t redeem myself on the other side. So at least I could expose myself to more people who liked what I was doing. And that was a more fruitful path.
How has that affected your business?
It probably cost me 30 to 40 percent of my income, on the Dilbert side of things. I could no longer do a public speech for money, like a corporate speech. I’m too radioactive. There’s a lot of things you can’t do if people think you’ve taken a side.
Have you ever clashed with your followers?
You follow the Q situation? You know, there’s a hoax person or persons pretending to be a deep insider?
Yeah, I do.
Well there’s a subset of some supporters who were buying into all of that and I’ve quite aggressively been trying to talk them out of it for their own good and for the good of the country. But they push back pretty hard. So this week I’m just getting savaged by the believers of Q, because they think I’m some kind of a traitor to the cause. So, whenever there’s a good reason, and there is reason to make an exception, I do it quite aggressively and publicly.
How did that evolve into writing Win Bigly?
So my publisher had been asking me for another book since “How To Fail at Almost Everything and Still Win Big” was very successful and changed a lot of people. My interests had sort of moved to this area. And so it was really the only thing I wanted to write about because I was I was pretty immersed in that since the election, the “persuasion take.” And so I proposed that, and they said yes, and “Win Bigly” is doing even better than the last book. So because I was a writer, I knew persuasion, I could do Twitter, I can do interviews. I knew how to get a book published. I had the opportunity to take my career in a different direction.
Do you think all of these ventures—WhenHub, and Dilbert and your writing on Trump—are connected somehow?
I wrote about that in my [first] book. One of the key points that I recommend that has served me well is the idea of a talent stack. So my life’s strategy, which I started probably in college days, was to compile as many skills as I could, especially ones that work well together. Because that’s how I could be special without being genetically special or born into a lucky circumstance. And most of the things I’ve been able to do are because of that weird combination of skills I put together. So cartooning for example, is a little bit about drawing, a little bit about writing, a little bit about being funny, a little bit, in my case, about knowing about business, so I have something to write about and then a whole lot about marketing and sales and persuasion and all the things that make something that’s good enough to be big. So, it’s a combination of skills that makes a difference.
The greater good that I’m trying to pursue is to help people understand their reality a little bit better. Because if you can understand why persuasion works and facts don’t work in terms of persuading people, you could be a much more effective person. Suddenly, a lot of your frustration disappears, because you’ll understand why things are the way they are. It’s sort of become a mission.
This interview has been edited and condensed.