In short
Podcast Summary: The James Altucher Show - Episode with Scott Adams: The Advice I Still Think About
Overview In this episode of *The James Altucher Show*, James Altucher interviews Scott Adams, the creator of the iconic comic strip *Dilbert*. The discussion delves into Adams's unique perspective on success, creativity, and the dynamics of goal-setting versus systems thinking. Following Adams's recent passing, the episode also serves as a tribute to his life and work.
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Key Themes and Discussions
Tribute to Scott Adams
- Personal Connection: James Altucher shares a personal anecdote about his long-standing friendship with Scott Adams, highlighting his influence as a mentor.
- Legacy: Adams's work is celebrated for its deep insights into success, persuasion, and the struggles that lead to creative breakthroughs, with specific emphasis on his books *How to Fail at Almost Everything and Still Win Big* and *Win Bigly*.
Life Philosophy
- Goals vs. Systems:
- Adams argues that setting specific goals can be detrimental; instead, he advocates for building systems that allow for flexibility amidst changing circumstances.
- Quote: "Build systems instead of chasing goals, because the target will move before you get there."
The Power of Persistence
- Rejection and Resilience: Adams recounts his journey into cartooning, including numerous rejections and how a single nudge from a mentor helped him to persist.
- Acceptance of Failure: Emphasizes that failure is part of the process and underscores the importance of trying multiple ventures to increase the odds of success.
The Emotional Side of Success
- Disorientation after Achieving Success: Adams shares his experience of feeling lost after achieving financial success, which he describes as a disorienting moment that led him to seek new purpose.
- Quote: "As soon as it happened, my life purpose evaporated."
Creativity and Risk
- Writing with Danger: Adams discusses the importance of incorporating risk and authenticity into writing. He believes that safe content often gets ignored.
- Quote: "I don't publish unless I'm scared or embarrassed."
Energy Management
- Maximizing Energy: The discussion includes strategies for managing personal energy through diet, sleep, and exercise, highlighting their importance in maintaining productivity and creativity.
- Quote: "If you care about success and you haven't taken care of your physical tool first, you're not even trying."
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Key Takeaways
- Focus on Systems: Rather than being fixated on goals, cultivate systems that allow adaptability.
- Embrace Rejection: Use failure as a learning tool and a step towards eventual success.
- Manage Energy: Prioritize health and energy management as foundational elements for sustained creative output.
- Perception of Ideas: Understand that not all friends or peers can accurately judge the merit of an idea; trust your instincts and persistence.
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Timestamped Highlights
- [03:04] James Altucher's introduction and personal tribute to Scott Adams.
- [06:50] Discussion on the concept of "systems beat goals."
- [12:26] Insights into Scott's daily routine and creative process.
- [22:12] The importance of incorporating risk into writing.
- [30:09] Reflections on the emotional challenges of success.
- [41:53] Discussion on the unpredictability of judging good ideas.
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Additional Resources
- [Scott Adams - Coffee with Scott Adams](https://scottadams.locals.com/)
- [How to Fail at Almost Everything and Still Win Big - Scott Adams (Amazon)](https://www.amazon.com/How-Fail-Almost-Everything-Still/dp/1591847745)
- [Win Bigly: Persuasion in a World Where Facts Don’t Matter - Scott Adams (Amazon)](https://www.amazon.com/Win-Bigly-Persuasion-World-Matter/dp/0735219710)
- [Dilbert (official site)](https://dilbert.com/)
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This episode serves as a poignant reminder of Scott Adams's influence on creative thinking, resilience, and the importance of pursuing one's passions amid the complexities of life.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Impact of Success on Life Purpose
0:45 to 2:45
Scott Adams discusses how achieving success can lead to a loss of purpose.
“You did a thousand things, and every one of them had a 10 % chance of working.”
Lessons from Failure and Dilbert's Success
2:45 to 5:00
Exploration of Scott Adams' journey and the lessons learned from failure leading to Dilbert's success.
“And I have to say Scott Adams has more recently become known for his, his political musings.”
The Philosophy of Persuasion
5:00 to 7:27
Discussion on Scott Adams' insights into persuasion and the nature of self-help books.
“But I have to say, as much as I enjoy your Dilbert comics, I enjoy even more everything else you write.”
Living by Systems vs. Goals
7:27 to 10:55
Scott Adams shares his perspective on the importance of systems over specific goals in life.
“So if you went back 100 years, let's say you were a farmer and you had a goal to clear 40 acres before winter, that was a simple, accomplishable goal.”
A Day in the Life of a Cartoonist
10:55 to 12:25
Scott Adams describes his daily routine as a cartoonist and the creative process behind his work.
“I do the finished art when I don't have to use any brain power.”
The Birth of Dilbert
12:25 to 14:03
Scott Adams recounts the story of how Dilbert was created and his journey into cartooning.
“And you started your first Dilbert cartoon you drew in 1989?”
Journey to Cartooning Dreams
14:03 to 16:43
Learn how Scott Adams navigated the challenges of becoming a cartoonist.
“So I started thinking, well, maybe I could try my hand at cartooning just on the side because I'd always had an interest since childhood.”
The Breakthrough Call
16:44 to 19:21
Discover how Scott received a life-changing call from a syndicate editor.
“And I remember thinking, well, maybe he knows something I don't know.”
The Balance of Cartooning and Work
22:52 to 28:01
Explore the tension between Scott's corporate job and his passion for cartooning.
“You wrote something very interesting a few weeks ago on your blog where you basically said that a writer should have an element of danger in their writing.”
The Value of Entertainment and Dilbert's Impact
28:01 to 30:09
Explore the role of entertainment and Scott Adams' Dilbert in the workplace culture.
“But I also can't help thinking as important things go, it's at the bottom of the important list.”
Show all 27 chapters
Perseverance and the Journey to Cartooning Success
30:10 to 33:04
Understand the importance of perseverance in achieving success in cartooning.
“And suddenly, it wasn't so dangerous for them because they're not saying this is my opinion, but obviously they're sharing the opinion or they wouldn't pass on the comic.”
Creating Your Own Luck Through Experimentation
33:05 to 35:00
Learn how diversification and trying many things can lead to unexpected successes.
“But any way you look at it, it's very demotivating, right?”
Combining Skills for Success
35:01 to 37:52
Discover how combining different skills can lead to unique career opportunities.
“So in that sense, you can't control when the luck happens, but you can guarantee that you get a payoff.”
Energy Management Over Passion
37:53 to 41:06
Learn why managing your energy is more important than simply following your passion.
“And, you know, another another point you make, and I'm kind of going through all the all the things that I think are also the most important is more important than passion is is energy.”
The Importance of Hiring the Right People
41:07 to 42:01
Understand the critical role of hiring the best talent in business success.
“And I've been involved in all aspects of the hiring process, whether sometimes I would have to hire a CEO, but sometimes software developers, sometimes designers, sometimes head of sales or business development.”
The Importance of Hiring Right
42:01 to 42:51
Learn why hiring the best talent is crucial for business success.
“I used to think I was frugal because I would try to find employees as cheaply as possible.”
Navigating Criticism and Ideas
44:06 to 46:01
Understand how to handle criticism and recognize valuable ideas.
“maybe sometimes people want to have an excuse why something hasn't worked out.”
Finding Value in Bad Ideas
46:01 to 48:24
Explore the concept that bad ideas can lead to good ideas.
“So it was a company initially called Odeo and they were setting up software for podcasts, ironically, given that we're on a podcast.”
The Launch of CalendarTree
48:24 to 50:52
Hear about the inception and purpose of the CalendarTree app.
“And in that process, I think people say, I don't agree with that, but you're making me think differently than I was before, and maybe that leads to something good.”
Strategizing for Growth and Funding
50:52 to 53:59
Learn about strategic approaches for funding and expanding a startup.
“one - or two-man startups, everybody's got different calendars.”
Creative Intersections in Business
53:59 to 56:03
Discover how creativity links various aspects of business development.
“where not everybody's going to have the same calendar system.”
The Indirect Benefits of Blogging
56:03 to 57:22
Discover how blogging can lead to unexpected opportunities.
“You're not saying if I blog this much, I get X dollars.”
Personalization in Creative Work
57:23 to 59:36
Learn how personal experiences shape creative expression.
“Well, you know, Dilbert is a big part of my personality put into the character.”
Navigating Controversial Topics
59:37 to 1:00:48
Explore how addressing both sides of an argument can provoke strong reactions.
“Yeah, they can't handle that because unless you agree with them, you're wrong.”
The Risks of Hedge Funds
1:00:49 to 1:02:02
Uncover the dark side of hedge funds and investment risks.
“oh, he's just a loser who wishes he could make it in the stock market.”
Rethinking Education and Politics
1:02:03 to 1:05:06
Examine the evolution of education and political systems.
“Like, what do you actually, people don't realize the kind of history of the university.”
The Case for Internet Voting
1:05:07 to 1:07:46
Discuss the potential benefits and challenges of voting online.
“You know, and if you've read the blog, you know that I've talked about lots of different governmental tweaks and ways you could fix things.”
Transcript
Automatic transcript. May contain errors.0:00Today on the James Altucher Show. My boss literally told me in these words quite directly, I can't promote you because you're male because we have a very balanced senior management. We don't have any diversity in management. It's like I don't publish unless I'm scared. Yeah, or embarrassed. The first time I got that big check, the one that you say, you know, I could stop working right now if I wanted to. I mean, if I wanted to, I could. Just, I'd be done. It actually is a terrible feeling. As soon as it happened, my life purpose evaporated. You know, I wasn't married, didn't have a family at the time.
0:39I suddenly lost my entire reason for waking up. So it was actually a sad, depressing, disorienting thing. You did a thousand things, and every one of them had a 10 % chance of working. You're pretty close to a guarantee that something's going to work. So I like to think of life as like a strange kind of casino with a slot machine. that instead of a slot machine that takes you money every time you lose, it's free. You just pull all day long. All right? This isn't your average business podcast, and he's not your average host. This is The James Altucher Show.
1:26You know, I've known Scott Adams for probably 12 or 13 years. He was one of the first guests on this podcast. And, you know, he's the creator of Dilbert, which was my favorite cartoon strip for decades. But then, you know, starting around 2013, he started writing about his life and his opinions and his approach to life and what made him a success. Like the first book he did in this genre was How to Fail at Almost Everything and Still Win Big. He also wrote another book, which was very influential, called Win Bigly, Persuasion in a World Where Facts Don't Matter. Both of these books are must reads.
2:07like win bigly is the best book ever about real world persuasion and scott adams himself was kind of an i don't i want to say he's an amateur hip hypnotist but really more like a professional in terms of how he used hypnotism techniques for persuasion and how to fail at almost everything and still win big this comes from the very first podcast i had with him how his story of how Dilbert became a hundred million dollar success. He was failing constantly. And the story of it, of the success of Dilbert, which he tells in this episode, we're going to show you now is just amazing. And I have to say Scott Adams has more recently become known for his, his political musings.
2:51And he had a daily podcast coffee with Scott Adams, which I regularly listened to. I would say over the past decade or 13 years, 12 years, he has not only become like a great friend and even somewhat of a mentor to me. We've talked a lot, you know, on and off the podcast and his podcast, my podcast, and really helped me out through some times when I was a little upset about different things. And he really knew how to reframe problems so that they would become successes. And I really just, when I first heard he was sick, like this is last June, I was devastated. And of course, you know, he prepared us all that he was going to pass away, which he did a few days ago.
3:40And it was really upsetting. And, you know, I'm not, I hate when people kind of take advantage of someone's death by saying, oh, I knew him great. He was my best, blah, blah, blah. I just want to tell you, put aside all your opinions. He was a great artist. He was a great storyteller. He had opinions you may or may not agree with. But he really knew a lot about the DNA of success and kind of the real mechanics of persuasion. like no BS, no academic stuff, just really how to do it. I would really encourage you. You could better your life if you read his books. I love this guy. I'm really sad he passed away.
4:27And I've learned so much from him. And I want to share a little bit of that in this episode. Maybe we'll even do another one at some point. Rest in peace, Sky Adams. And please, if you haven't learned from him in the past, or even if you have, we had a great time whenever we talked. And, you know, here's a piece of that.
4:52So, Scott, I just pre-ordered your latest book, Go Add Value Someplace Else. So I'm looking forward to getting that. Yes. But I have to say, as much as I enjoy your Dilbert comics, I enjoy even more everything else you write. Like your book from last year, How to Fail at Almost Everything and Still Win Big, kind of the story of my life, is one of my favorite books. Thank you. I appreciate that. It hasn't gotten nearly the public acceptance that I would hope, but the small group of people who are reading it seem pretty excited about it. So that's meaningful. Well, let me ask you a question. Given that you're read in 2 ,000 newspapers or more now for all I know, how come this book didn't really get all out there?
5:39you know i think it's in a genre that tends to be more of a fashion type of a business because it used to be the self-help books were everything you know everywhere there was a self-help book now i think you'd find that probably there are very few self-help books of any type that are being sold part of the problem is that people figured out that you can't read a self-help book and then it changes your life and everything's good so i i tried to make a big point in mind that I wasn't giving you a recipe because everybody's case is different, but rather I was giving you an example, a template, if you will, that if I did this and this is what turned out, that maybe you could compare that to what you're doing and what other people are doing and find something that works for you.
6:22Well, you know, I always say the greatest marketer ever had the exact same technique. So Buddha said, don't believe me. This is just what worked for me. Be a skeptic. Can you try it for yourself and see if it works for you? And that viral marketing spread, of course, all through India within years. I wish I had a nickel for every time I've been compared to Buddha. Maybe you'd have a dime or something by now. That's right. Yeah, but who markets better than Buddha? So, yeah, I can see that. So, what I really liked in this book, and I really subscribe to this as well, this idea that goals are bullshit.
7:01You say live by systems. I call it something similar. I say live by themes. But I really think so many people come to me and say, oh, I have to find what my goal is in life. And that's just meaningless. And the idea of living by a system or a theme is much more valuable. And so what do you mean by systems? Well, first of all, I think that this sort of snuck up on society because society became more complicated. So if you went back 100 years, let's say you were a farmer and you had a goal to clear 40 acres before winter, that was a simple, accomplishable goal. And by the time winter came, it was probably still a good idea.
7:45So you'd be glad you did it. Now you fast forward to 2014, and I have more complexity in my smartphone in my pocket than the farmer had in his entire operation. I don't know what the world looks like next year. I don't know what my industry looks like next year. I don't know, as a cartoonist, I don't know if newspapers exist next year. I mean, there are a lot of things I don't know. So if I pick a goal and say, five years from now, I want to be here, what are the odds that that's still a good place to be in five years? So rather than taking that pinpoint approach and trying to shoot at something that probably isn't even a good target to begin with, because the world will change before you get there, I say do things that improve your odds in a fairly general way so that no matter what the future looks like, you're in a good position to take advantage of it.
8:36The most obvious and common example of that is simply stay in school, go to college, get a degree. Obviously, it matters which degree you get. But the general idea that if you become more educated, you're in a better position to take advantage of whatever opportunity, people get that. But I think there are lots of other ways to exploit that same phenomenon, which is if you just put yourself in a position where the odds are better, you can't predict exactly how that's going to turn out, but you're probably in a better position. Well, it's interesting because I think people almost limit their odds when they are, when they're goal oriented at all.
9:13So like, take the example you said, like going to college, then going to grad school, then getting a job and having as a goal promotions and then eventual retirement. That's sort of like the natural path of the past 100 years. And that path is totally destroyed, you know, millions of lives, like more lives than war destroys. Yeah. You've got that problem that not only do you not know what the future is going to bring, but the moment you say, this is my goal, then the whole point of having a goal is focus, right? And the point of focus is to tune out all the rest of the noise. Now, the problem is that there might be more value in the noise than in the goal.
9:51And that's what I'm proposing here is that the world is full of opportunities. There may be plenty of things that were not your goal, not something you anticipated, that were way better than what you imagined. I mean, there was a point in my life where I was dead set on becoming a corporate lawyer. I thought that's where I was at. Now, had I kept that goal and been kind of laser-like focused on that, I'm sure I could have accomplished that. But would I be happy compared to how things turned out? I don't think so because I wore my pajamas all morning doing my work today, and I don't think I could do that as a corporate lawyer.
10:25So let's talk about your day. So you woke up and you're in your pajamas and you started drawing a cartoon. Well, yeah, I get up around six, get my coffee, and then I usually either read my email or maybe write a blog post on Dilber.com or do something. Then I kind of get into my cartooning. Usually do about two comics on a typical weekday in rough form. I write them and I draw them in rough form. and then sometime later at night or the afternoon when there's some slow time, I do the finished art when I don't have to use any brain power. It's pretty much just skill. And how long does it take to do one cartoon, you think, to write it out and come up with the idea and so on?
11:10It varies a great deal. So one of the things I learned when I was working my day job when I first started cartooning, and I was getting up at 4.30 in the morning and I had to be done with the cartooning by about 6, and I had to do one every day, I found that sometimes I'd have a good idea right away and I'd have a full hour and a half to develop it. But other days, I'd have 10 minutes left, I had nothing. And I would just say, okay, I don't have any good ideas, so I'm going to have to write down something because it's not an option to do nothing. So I'd quickly throw together what I thought was a bad idea, and then I would wait to see how the audience reacted.
11:46And what I found is that I could not predict the good reactions or the bad reactions based on the work I'd done. In other words, I didn't have any power of prediction. And that freed me from thinking that it's only a good idea if I am dead certain it is at the moment. So rather now I say, I'm pretty sure this will work, and I put it out there, and then I'm surprised. But that's a long way to say that sometimes I can knock it out in 10 minutes, meaning that I got the idea and I rough out the art in 10 minutes. But that's unusual. More likely, it's closer to 40 minutes or an hour, I would say, to rough a cartoon, and then another 40 minutes to finish the art some other time.
12:28And you started your first Dilbert cartoon you drew in 1989? That's the first time it was published, yes. And how long had you been drawing them before they got published? Well, it was a doodle that I did in my day job. I was working at Pacific Bell, that was then the local phone company. And probably two or three years, it was just a doodle that I would draw on my whiteboard at work. Sometimes I'd work him into my presentations I gave at work. And then one day, my manager at the time suggested that his name, he didn't have a name. He said, maybe you should call that guy Dilbert. And that's kind of when it all came together.
13:08And then you started submitting it to syndicates or newspapers? Yeah, so the process, I could give you the interesting longer version or the tight, short version. Let's do interesting. Oh, interesting. Okay. So one day in my corporate career, when I'd been told for the second time that I couldn't hope to be promoted because of my gender. So it was a weird little time in San Francisco when there was reverse discrimination. And my boss literally told me in these words quite directly, I can't promote you because you're male because we have a very balanced senior management. We don't have any diversity in management.
13:50So until that gets fixed, which could be 100 years, there's no hope of you getting promoted. So I started thinking, well, what can I do that's not in corporate America where I can do something where my talent alone makes a difference? Or better yet, move to somewhere where being who I am is an advantage. instead of a disadvantage. So I started thinking, well, maybe I could try my hand at cartooning just on the side because I'd always had an interest since childhood. But I didn't know how. Like, how do you become a cartoonist? Where's the starting point? Now, the interesting thing is that just as I was thinking this, I came home one day and I was flipping through the channels on TV and it was the end of a TV show about how to become a syndicated cartoonist or how to become a cartoonist.
14:35but I missed almost the entire show. I just caught the last few minutes and I figured out what it must have been about and I wrote down the name of the host and where it was broadcast from as the closing credits went by and I wrote a letter to the host and I said, I missed your show but I've got some questions about how to become a cartoonist. A few weeks later, I get a handwritten two-page letter from the host of the show. His name is Jack Cassidy And he gave me instructions on what book I should buy that tells you how to submit your materials to syndication companies and what materials you should use and a few other tips.
15:12And he gave me this advice. He said, it's a very competitive industry, and you're going to get a lot of rejections, but don't give up. So I thought, oh, this is great. I know exactly what to do now. So I bought the books he recommended. I got the materials he recommended, put together some of my finest comics. This was before Dilbert. They were single-panel comics. and sent them off to the major magazines, Playboy, The New Yorker, anybody who paid the most. They came back rejected, as you might imagine. I was an unknown cartoonist, and the comics were fairly terrible at the time. But I figured, okay, I tried.
15:45I gave it my best shot. I did what I could. It was my best effort. It didn't work out. Like, that's life, right? Not everything you do works out just the way you want. So I felt good about it, but I took all my materials, my drawing supplies, and I put them in a closet, I just forgot about it. I just moved on. About a year goes by. One day I walk out to my mailbox, and there's a letter. And it's from Jack Cassidy, the cartoonist who had helped me with the first letter. And I hadn't even thanked him for his advice. And I felt bad about that. I really owed him a thanks. And I wondered why he would write a second letter a year later.
16:25And I opened it up, and it said that he was cleaning his office. and he came upon in one of the piles, my original samples I had sent him when I asked for advice. And he said he was just writing to make sure that I hadn't given up. That was the only reason he was writing. And I had given up. And I remember thinking, well, maybe he knows something I don't know. Maybe he's seeing something with his experience that is invisible to me and invisible to the editors at Playboy and the New Yorker. and so I thought well I'm going to increase my effort rather than trying to become a mere gag cartoonist for magazines which would be good but not the lofty level of a syndicated cartoonist I decided to try to become a syndicated cartoonist and then if I got rejected I would be rejected at a higher level which would feel like progress in a way you know so I followed the directions in a book called Artists Markets.
17:24It's probably still available. It might be online now, I guess. And it just says, where do you send your samples? And I sent my samples out to the major syndicates. I thought most of them rejected me. I got all the rejection letters and said, thanks, but no thanks. One of them helpfully suggested that I might find an actual artist to do the drawing for me, and that might work out better for me. But I thought I had all the rejections. And again, I said, well, second time. I've tried. Didn't work out. I put my materials away. A few months go by, and I get a call out of the blue from a woman who said she was an editor for some company I'd never heard of, some company called United Media.
18:07And I hadn't sent my samples to anybody by that name, so I was confused that she was calling me, especially when she offered me a contract to be a syndicated cartoonist for newspapers. And now for the viewers, the way syndication works is that if you get a syndication contract, that's your big break because it's the syndicate, which is a company, that sells to the newspapers. They do all the marketing and turning things into licensed products and such. So that seemed like a big opportunity, but I'd never heard of this United Media Company. I didn't know where they got my number from. So I was playing it kind of cautiously and I said you know I'm flattered by your offer but frankly I've never heard of this United Media Company do you work with any cartoonists that have been published?
18:54Is there anybody perhaps I've heard of? And there was this long pause and then Sarah Gillespie was her name she said yeah we handle Peanuts and Garfield and Rubberman and Nancy and when she got to about the 12th name on the list I realized that my negotiating position had been compromised. And so I did end up signing that contract with them. It turns out that United Media was the parent company of United Features, where I was then, and so I didn't recognize the parent company name. That's why I was confused. Since then, I've moved to Universal. Andrews McNeil is publishing the books, so everything's good now.
19:41Take a quick break. If you like this episode, I'd really, really appreciate it. It would mean so much to me. Please share it with your friends and subscribe to the podcast. Email me at alcatra at gmail.com and tell me why you subscribed. Thanks.
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22:51So you started the cartooning with United, but you still stayed at your job at Pacific Bell and you were cartooning every morning and how long before you said okay you know what this is i'm gonna take the jump this is it uh well that decision was made for me by my boss when dilber was just starting out i had a little bit of a target painted on my back i learned later i didn't know that but i found out later from people in the know that the senior management wasn't happy that I was making fun of the corporate environment. You wrote something very interesting a few weeks ago on your blog where you basically said that a writer should have an element of danger in their writing.
23:36And I'm paraphrasing, but I thought this was extremely valuable writing advice. Like probably now the internet is filled with top 10 reasons to, or top 10 ways to be a better leader, top 10 ways to be happy. And no one actually takes risks in their writing, even though there's much more writing than ever before. And you said that Dilbert, there was this danger because you're essentially making fun of the work environment that you worked in. Yes. First of all, I would say that you actually put danger into your writing, which is why I like it. That's why it resonated so much with me, that advice.
24:13Like I don't publish unless I'm scared. Yeah. Or embarrassed because when I read your writing, What I'm reading is, God, how many times did you rewrite that sentence? Because I know you're looking at it and saying, I don't want to say this, but I have to say this. So I'm feeling you. When I was first doing Dilbert, I think people sensed that I was in financial danger. And I was. Now, it turns out that my personality is such that I tend to run toward danger. It's not a good thing. I'm not proud of that. But you're wired the way you're wired. So I kind of naturally was attracted to the dangerous part of it.
24:49I look for that in writing that I read, but it just came to me naturally and accidentally in my case. So you said you had a target on your back. Did they fire you eventually? Toward the last year or so, when Dilbert was getting pretty big, my co-workers came to me with an offer. In fact, one of my co-workers is the real-life inspiration for the character Alice. So she was an engineer at Pacific Balance. She was probably one of the best engineers and tough as nails. So she became the Alice character. But she came to me with this offer. She said, a lot of the customers like seeing you because they come in and we show them our technology in the lab and try to get people to buy our stuff.
25:26So we like keeping you around and we'll do your work for you if you just show up to work once in a while when a customer is here. So in the final year, I worked on a deal with my coworkers and with my boss where I said, I'll do what I can, but it's no longer my priority to come to work. But anytime you need me to leave for budget reasons or any other reason, just let me know. And one day, just for standard budget reasons, my boss said, yeah, I think I need an employee who does real work more than I need this guy who just shows up and customers like him once in a while. So then you were home alone, essentially.
26:00And now your goal, quote unquote, was achieved. Like you're a professional cartoonist. You had no more role in the standard corporate workplace. Was that like this amazingly happy feeling or were you scared? Oh, you're asking a good question. because I think you already know the answer to this question, which is, I'll tell you the moment that's the most interesting. So I got my first publishing deal, book publishing deal, and those tend to be, if you're lucky, it's a multi-book contract and it's a very big number. And the first time I got that big check, the one that you say, you know, I could stop working right now if I wanted to.
26:37I mean, if I wanted to, I could, just I'd be done. It actually is a terrible feeling. And I did not expect that because my whole life I was working toward that objective, you know, to have enough money that I could do what I wanted to do. And as soon as it happened, my life purpose evaporated. You know, I wasn't married, didn't have a family at the time. I suddenly lost my entire reason for waking up. So it was actually a sad, depressing, disorienting thing. and what grew out of that is when I started the Dill Burrito vegetarian food product that I was working at on the side because I was trying to figure out some way to do something useful for the world so that I could get back my sense of meaning and I thought well the world of nutrition is a mess if I could make a product which has all the daily nutritional needs and it was simple then I've contributed something to the world.
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27:32Why didn't you think the strip contributed something to the world. Basically, you were opening up the window on what I call corporatism is really like, as opposed to capitalism, for instance. Yeah. I've had this conversation a lot. It's the question of whether entertainment is sort of a real value. Now, on some level, of course it is. People like to be happy. You need to manage your attitudes as well as any other asset you have. So sure, entertainment's an important real thing. But I also can't help thinking as important things go, it's at the bottom of the important list. You know, like if you had to downsize the important things, what would you lose first?
28:16It's always the entertainment, right? No, I don't know because look at comedy in general, the world of comedy. You take a guy like Louis C.K., you know, who I would say is a similar genre to you, this observational humor that really sheds light on things that people don't normally think about. People normally just go through their daily lives without thinking of these issues. Like, oh, what Scott Adams just pointed out, what Dilbert just pointed out, is something really stupid that happens in my life every day that I never would have thought about before. Yeah, I'm not going to say it has no value.
28:49I'm just saying that among the valuable things, it's at the bottom. All right. And maybe that's because I'm too close to it. You can't really see it the way other people see it if you're the one producing it. but I'm shocked and amazed and humbled that people read it every day. I'm happy about that. People read it, and unlike many other comic strips, people hang it up on their cubicle walls. You know, I used to work in an IT department in the Time Warner family, and every cubicle had like Dilbert cartoons hanging up in it. Like it had an effect on people. It had an effect on cubicle life. Yeah, I hear stories all the time.
29:26This is anecdotal, so I can't put any science on it, But the number of people who say, my boss was starting to roll out a program, and then he caught himself and said, uh-oh, this could appear in a Dilbert comic strip, and then he completely rolled it back. So I think that before Dilbert, management had a free pass. They could do literally any ridiculous thing and say, oh, I read a book that says this new process, this new system is going to change the world. And they could get away with anything. But as soon as you have the threat of public mocking, and in effect, I gave employees a voice because they could take my words in the comic strip and cut it out and slip it under their boss's door, you know, pre-internet and then post -internet.
30:09They could email it to them. And suddenly, it wasn't so dangerous for them because they're not saying this is my opinion, but obviously they're sharing the opinion or they wouldn't pass on the comic. So I think I gave employees a voice, and it's a mocking voice, which I think does put some control on management. You know, and the fact that it's a cartoon as opposed to, let's say, an op-ed in the Wall Street Journal, actually puts some distance between kind of the opinion and the danger of it. So it could be both dangerous and opinionated, but hey, it's a cartoon. So people could say, hey, don't take me so seriously, but look, there is this opinion that's valid.
30:49Yeah, and that's part of the phenomenon that the funnier something is, the more you can get away with. A related phenomenon is that there are some topics, some subjects that you would never be able to publish in a comic because people would get too angry. Unless it's really, really funny, and then you can totally get away with it. And that's true with making any kind of serious commentary about the world. There are things that people would jump all over you if you said non-funny. but if you put it in a funny context, people are willing to absorb it. So it seems like from the beginning, the system here was there was perseverance.
31:28And what I know from your book is that you were interested in cartooning when you were a little kid. So you kind of took out these passions and we all have these passions from when we're like 10 years old that we kind of leave in our 10 year old history, but you took it out and you You persevered with it. You handled rejection. And you kept doing it until it was time to make a break. You didn't rush it. You didn't leave cartooning once you got all rejected. So there was a system there. Well, you know, my background was economics. I was an economics major, then business major. So I tend to look at things in the most practical way you could go.
32:11One of the things I reject is the notion of passion or chasing your passion. So that's also what I wrote about in How to Fail Almost Every Time and Still Win Big, is that I think passion comes from things that work. So my system was to try lots of stuff and see which ones just are going to work on their own because it was the right time, it was the right combination of skills. I got lucky, something happened in an environment that I didn't know about, and it was just the right time. So I tried lots of things, and that's mostly what the book is about, is how many things didn't work. So if you looked at just cartooning in isolation, and I worry that when people looked at my career, it was actually demotivating because they didn't have the context of how many things I tried that didn't work.
32:55So if you look at just the cartooning part of my life, it looks like I shot an arrow and hit a running rabbit at 100 yards. And like, wow, that was either amazingly skillful or incredibly lucky, but probably both. But any way you look at it, it's very demotivating, right? Because you can shoot a lot of arrows in the direction of a lot of running rabbits, and you're not going to hit one. But if you look at it in this context, which is cartooning is just one of the dozens of things that I tried, and all of the other dozens of things were reasonably good ideas, which I had the ability and resources to expect some sort of execution that wasn't terrible.
33:36But most of those didn't work out, and most of the things that didn't work out were because of bad luck, bad timing. Things just didn't come together. But it's that kind of diversification of opportunity that creates the luck. So you play a lot of tennis, and I'm sure you've had this phenomenon where you play someone in tennis and you win, and they say, oh, you just got lucky. And there's a saying in chess, so I play a lot of chess, there's a saying in chess, only the good players get lucky. It always seems like the good players are the luckiest ones. So the same thing happens in life. It's not quite like you create your own luck, but you leave yourself open for the opportunity of luck.
34:16Yeah, it's just math. I mean, there's a reason that people diversify their portfolio. There's a reason that buy and hold works. It's a reason that index funds work. It's just math. And the fact is, if you try one thing once, probably things aren't going to go your way, right? Because the odds of any one thing working, even if you do everything right, is about 10%. But if you did a thousand things and every one of them had a 10 % chance of working, you're pretty close to a guarantee that something's going to work. So I like to think of life as like a strange kind of a casino with a slot machine that instead of a slot machine that takes your money every time you lose, it's free.
34:58You just pull all day long. All right. So in that sense, you can't control when the luck happens, but you can guarantee that you get a payoff. off i mean this also goes along with the concept that you could even be fairly mediocre at all the things you're trying because if you try lots of them it's like what you said in your book once you actually got syndicated you found your cartooning skills got much better because people do tend to become let's say more passionate at what they're good at as opposed to the other way around yeah i had a total wizard of oz moment if you know the wizard of oz you'll know what i'm talking about, when I first got the contract to become a syndicated cartoonist, my level of drawing skill went from abysmal to just a little bit terrible.
35:42I mean, for me, that was a big increase. And I would say since then, I've improved through brew force and practice to, that's pretty good. That's about as good as I'll ever get. But yeah, it turns out that people are not great at knowing what they're good at. You know, another thing that you point out, which I believe very strongly in, is the idea of combining systems or combining skills. Yes. So you don't have to be great. Not everyone's going to be the best mathematician in the world. But if you combine some skill in biology and some skill in mathematics and you become a biomathematician, then it's much easier to be the best in the world.
36:25Yeah. So in my case, I use myself as the example of that point. which is if you look at my artistic skill, there's no one in the world who would accuse me of being a real artist. And yet, that's my job. I draw stuff for a living, and I'm not a good artist. But it turns out that when you combine my mediocre drawing skills with my writing skills, which again are not Pulitzer Prize winning writing skills, but they're pretty good. They're accessible. My points are usually clear. So it's good enough. Now you put those things together, still not enough, right? I've got a little bit of drawing, a little bit of writing skills.
37:01Still not enough. A lot of people have that. But then I was lucky enough to have this corporate background. And again, lucky enough that I discovered somewhat accidentally that pulling from that experience was what the audience wanted to see. None of this was something that I had cleverly constructed as a plan years ago. It was just a combination of mediocre skills, mediocre business, writing, and art skills. Now, I would argue that over time, all of those skills have improved quite a bit. I would say I'm a reasonably good business person now. Not great. I mean, I'm not Warren Buffett. I'm better than the average person who never put any effort into it.
37:41And I draw better than the average person, and I write better than the average person. But you put those three things together and get a little luck, a little timing, and it's magic. You are quite self-deprecating, though, as well. I mean, you are. I've earned all that self-deprecation. Fair enough. Fair enough. And, you know, another another point you make, and I'm kind of going through all the all the things that I think are also the most important is more important than passion is is energy. And, you know, we're sort of allocated this amount of energy each day and maximizing what you do when you have the most energy is incredibly important as opposed to having passion for something.
38:24And that's when you talk about nutrition and exercise and sleeping and all the things we do to maximize our energy. I think this is incredibly important. Stress is another thing too that takes away energy. Yeah, I got lots of criticism from folks for including in a book that's about success, diet and exercise. And interestingly, I guess that's just a social, cultural kind of thing that people like to put that in a different box. It's like, okay, that's just what I'm doing personally as opposed to what I'm doing to try to get success or whatever. And if you separate those things, you've missed your biggest opportunity because, you know, I'm 57.
39:04I'm in perfect health. I can work all day if I want to. I get up at six when my energy is best and I do the things which require the most energy, the creative stuff. and then I wait till later in the day when my brain is kind of mosh and I do the mindless drawing and filling in the lines of my art. And if I were to just simply reverse those two things, I wouldn't even have a career. I mean, it's a gigantic impact. The difference between your best moment of the day, you know, when your brain is clicking, you've got it, everything's happening, what idea you come up with then, your inspiration then versus, you know, your dull-brained three o 'clock in the afternoon, I ate too many carbs, I need a nap, kind of thinking.
39:47I mean, those are, it's not even the same person, you know, there's such a difference. You know, I think people, like look at the popular self-help books of, let's say the past 15, 20 years, you know, you have the secret. So people, people want a secret. They don't want to simply be told that the magic equation is sleep eight hours a day, which is probably the most valuable thing you can do to have energy. That's what sleep is for, is to connect the, re-energize the brain completely for the next day. And there is no secret to it. Yeah. Yeah. In a sense, it's funny, the two criticisms I got in the book were opposites.
40:27One was, you know, don't include that stuff, you know, about diet and exercise and energy in a book about success. And another group saying, you're saying things that are too obvious. You We already know this, but I know that they don't know that because you just have to walk down the street in America and look at people and they haven't figured out the whole, if I get my body working, then everything in my life is better. If your body is working, you're fit and you're healthy and all that. Your social life is better. You get more job opportunities. You can work better hours, create better things.
41:00It all kind of starts with that. So if you skip over that part, are you really even trying? I would go so far as to say, if you care about success and you haven't taken care of your physical tool first, you're not even trying.
41:27So I have started many companies. Some did well, some did not do as well. I've also run many companies. I've advised many companies. And I've been involved in all aspects of the hiring process, whether sometimes I would have to hire a CEO, but sometimes software developers, sometimes designers, sometimes head of sales or business development. I've been involved in basically every aspect of running a business. And hiring is maybe the most important thing you could do when you start a business. So I'm going to give you one piece of advice and it's related to what I'm talking about here. I used to think I was frugal because I would try to find employees as cheaply as possible.
42:07Someone young, just starting out, whatever. But what I've learned is you do so much better as a business finding the best person in your field. If you want a head of sales, find the best head of sales. If you want a software developer, hire the best software developer. It ultimately will save you money, but it'll also save you so much time, so much aggravation, so much anxiety. These are all things you need to preserve. It's really important to hire correctly. When you're running a business, your mind is on your business 24 hours a day, seven days a week. That's the problem with being an entrepreneur is you never leave the work at the office.
42:43So when you're hiring, you need a partner that works just as hard as you do. I have found that a great hiring partner is LinkedIn Jobs. When you clock out, LinkedIn clocks in. LinkedIn makes it easy to post your job for free, share with your network, get qualified candidates that you can manage all in one place. And I find this is such a great platform to find people for your job because millions of people are on LinkedIn, millions of qualified people. Here's how it works. You post your job. LinkedIn's new feature helps you write job descriptions and then quickly get your job in front of the right people.
43:15Post your job for free or you pay to promote it. Promoted jobs get three times more qualified candidates. You get qualified candidates. At the end of the day, this is the most important thing to your business is the quality of those candidates. Based on LinkedIn data, that 72 % of small and medium businesses using LinkedIn say that LinkedIn helps them find high quality candidates. So that's good information. You share with your network. So when you're on LinkedIn, your whole business network knows you're hiring. So find out now why more than 2.5 million small businesses use LinkedIn for hiring today.
43:46Find your next great hire on LinkedIn. You can post your job for free at linkedin.com slash Altature. That's linkedin.com slash Altature to post your job for free. Terms and conditions apply.
44:05I think people in many cases, and this is not really a criticism of people, but I think maybe sometimes people want to have an excuse why something hasn't worked out. So for instance, I had one person write me and said, I'm following your advice about writing down 10 ideas a day and I'm exercising and sleeping. and then on Friday night, I go out drinking with my friends and my friends laugh at all my ideas. And he said, what should I do? And I wrote back and I said, stay at home Friday night. Like, don't go out anymore on Friday night. And I never heard from him again. Yeah, I might have added find new friends.
44:45Yeah, find new friends is another one. Although maybe on Thursday night, those same friends would have been supportive of him. I didn't have, I don't know. I just know on Friday night, they specifically were trashing him. One of the pieces of advice I give to people is based on my own experience. When I was first assembling my Dilbert comics to submit to syndication, I had about 50 of them in sample form, and I wanted to only send the best ones. So I would have my friends come in one at a time to help me sort my 50 comics into the good ones and the bad ones so I could just send the good ones. And it turns out that my friends were all over the map.
45:21They couldn't tell, or they all had different opinions about what was a good one and what was a bad one. So in the end, I just sent them all. But I've learned from that and a million other examples since then that people cannot tell a good idea. All right? Just no one is that smart. You can't pick a good stock. No one's that smart. You can get lucky, but you can't know. And nobody knows a good idea when they see it. So when you tell your friends your idea and they all laugh at you, what you should be registering in your mind is not, oh my god, I guess this is a bad idea after all. The tape that you should be playing in your mind is people don't know what are good ideas.
45:58It's really true. Do you know the story of the very beginning of Twitter? I might refresh my memory. So it was a company initially called Odeo and they were setting up software for podcasts, ironically, given that we're on a podcast. And it wasn't really working out. So they worked on this project on the side, which people sending messages back and forth and 140 characters. and they decided, look, this is getting interesting. We have 10 ,000 users or whatever. Let's devote ourselves to this. So Ev Williams, who was the CEO, he went to all the professional venture capitalists that had invested in Odeo and he said, look, Odeo's not working out, but you're welcome to stay in and we're gonna focus on this other little project that we've been working on or I will take you out completely at cost.
46:44You won't lose a dime and it's up to you. And 100 % of these professional investors all took their money out of Twitter. Well, so yeah, there could not be a better example because if you had come to me and said, I'm going to develop this thing that lets you send the message to people, I'd say, stop, already exists. We have something called email. You go, no, wait, wait, it's better than that. It really limits how much you can write to an annoyingly small amount. And I'd be like, mass, how can I get my money out? I'm out of here. I mean, there's nothing about that that on the surface would make sense.
47:19And you can go right down the line and find so many examples of things that you would not have predicted or that you predicted wrong. And yet this doesn't stop you from pursuing ideas, of course. As you mentioned, you've opened restaurants, you did the Del Burrito, you've done other things that, you know, you've had other ideas that you thought were good. Yeah, lots of other ideas, but I find value in the idea. So one of the things that I'm pretty serious about is that bad ideas have value. In other words, if I give you 10 bad ideas, those probably didn't have any value. But if it made you think of one that was good, it's like, oh, those 10 ideas were bad, but that makes me think of this idea.
48:00So the way you get to good ideas is through bad ideas. There's almost never a time when somebody just sits there in a blank room and says, ah, good idea. You don't go from here to there. You go through the bad ones first. So the more bad ideas, the better, as long as they're well explained. And I try to do that on my blog in particular. I make no claim that anything I write doesn't even make sense. It's a good opinion, good for the world, or anything else. But I do explain myself clearly. And in that process, I think people say, I don't agree with that, but you're making me think differently than I was before, and maybe that leads to something good.
48:38Also, the thing about, let's say, a list of bad ideas is it could be what I call idea sex. Two bad ideas put together, it actually could be the case that negative one plus negative one equals three. Yeah, I mean, I can't think of an example of that right offhand, but I feel like I should be able to. I can't think, well, 140 characters plus the internet. I don't know, maybe that turned out to be a good idea. Now, you've been doing this, you've been doing Dilbert for 25 years or more, Is this going to continue forever? Do you ever think about like, okay, I'm going to take a break. I'm going to stop.
49:17I think about that literally every day. And I have mixed feelings about it. I mean, since it isn't hard to do, it would be hard for me to stop because first of all, a lot of people depend on the things I do. And this is one of those top one percenter problems, which is that I'll call it the Spider-Man problem. You know, that with great power comes great responsibility. I'm in this weird situation where if I spend an hour of my time working, I produce more economic activity and value, I guess, than the average person working an hour. And it's a lot more because I'm in this lucky position. So I feel like this responsibility to continue to be productive, both as in a role model way, I don't think there could be anything worse than getting rich and quitting.
50:06Yeah, like what would you do? What would I do? Yeah. So I may have mentioned before that now I'm involved in a startup called CalendarTree, CalendarTree.com. I signed up for it. Thank you. All that does is solve a universal common problem, which is that somebody sends you a schedule of a long bunch of events for some sport or activity or whatever organization. You don't want to have to retype it manually into your computer. So instead, we turn it into a link calendar tree, and then you can use the link to add it to the calendar you already have. So it solves a very small problem, but I found that very satisfying because it's a real problem and there's not a other solution.
50:47So we took that out and solved it, and that's meaningful to me. And also, in a world where people are moving towards solopreneurship, one - or two-man startups, everybody's got different calendars. So everyone that you're trying to schedule with has different calendars, and the fact that you're sort of calendar independent is valuable. Yeah, so it's a complicated world and we just built one little product that simplifies just this one little part of it. Now, we hope to expand to solve a bunch of related problems in the scheduling field, but for now it feels good that we've done this one thing, people are using it and they're happy.
51:26And how many users do you have? It's in the low thousands right now. We're in the process of rewriting the code from the bottom up to make it more scalable now that we've discovered that people like it and it works. So we're going to wait for a big push until that's done, and we hope in another month or two. Would you have it as an app? I'm assuming for a mobile, you have it all set? Right now, we don't have an app because the most popular use for it would be you'd create a schedule that you're sending out to someone. So it works if you're the receiver. You can receive it on your smartphone and just click the link and add it to your calendar.
52:03But if you're the one creating it, you probably don't want to create a long schedule on a phone because it would just be too tedious. So at the moment, it's just a web app, but someday we'll have a mobile app. Or if I'm receiving, though, I could be like, let's say I'm on a bus and I have my phone and I'm receiving a calendar request. Well, I guess would I be receiving it on Calendar Tree or what if somebody sends me a Google Calendar request? So the way Calendar Tree works is that if the organizer creates a schedule, they can turn that into a link that they can send out any way you can send the link.
52:37So they can send it through social media, Twitter, Facebook, or email. Email is the most common. So on your bus example, you would check your mail and there would be an email and say, somebody you know has sent you this. Click here to add it to your calendar. And then you just click and say, I'm an Apple calendar or I'm a Google calendar or I'm an Outlook calendar and it adds it. So it was for multiple events. Obviously, if somebody sends you one event, you don't really need anything. Yeah, so that's interesting. So you basically like the business world. You write about it. You blog about it. You're starting a business.
53:11You've started other businesses. Have you thought about raising money for this? Well, right now we're adequately funded. We've started having the conversations, but until we do the rewrite in a month or two, I don't want to get too serious about asking for money because I want people to know what they're getting and we'll have a much better thing to show them in a couple months. It would be good also to get one good, maybe even corporate client to accept this as their calendar versus using Google Calendar or Microsoft or whatever. Well, we're not a calendar replacement. We're just a way to get whatever schedules you'd like to get on calendars onto any different calendar.
53:49But yeah, we're looking at corporate types as a way to get kind of a big footprint right at once. Or even something where they don't expect everybody to have the same software, like let's say a meetup type situation or a church or whatever, where not everybody's going to have the same calendar system. Yeah, that's ideal. In fact, what we do right now on calendartree.com, we put some of the major sports schedules up there. You don't have to be a member of Calendar Tree. You don't have to sign up. You can just go up there, click, and add it to your calendar. We're showing that someone like the NFL, NHL, or Major League Baseball could tweet out a link, and anybody who got it could say, hey, let me add the Giants schedule to my phone.
54:30You should do a deal with, I'm sure everybody says you should do this or you should do that, but you should talk to a company called Ticketfly. They're like Ticketmaster, but they deal with tens of thousands of events, and they are much more savvy with social media than Ticketmaster. They're just an interesting company. Yeah, we've talked to the companies that are in the event space and the ticketing space, and it's pretty crowded. And at the moment, we're not going after that ticketing kind of world. I could see maybe that happening someday down the road. But right now, we're going for a pretty limited problem and a full solution to a small problem.
55:04And again, it's kind of combining your economic skills with probably your experiences on the internet over the past 20 years. You know, it's actually interesting how much of the startup and the cartooning and the other stuff I'm doing is related because it's all creativity and it's all engineering in your mind. It's like the thrill I get from thinking of a new business model, a way to create money and value that had not been thought of before is exactly the thrill I get when I have an idea for writing a blog post or writing a comic. Yeah, it's interesting because I find, like, let's say I own a stock and the stock goes down, I'm disappointed.
55:44But if I wrote a good blog post that day, even though they're completely unrelated, like in one case, I'm actually losing money. In another case, it almost means nothing to any aspect of my career. But I feel so good from the good blog post that it outweighs the bad feeling of losing money. By the way, I would argue that your blogging is a system in the sense that you don't have a specific monetary goal. You're not saying if I blog this much, I get X dollars. But the only reason that I agreed to this podcast is because I've read your writing. So I'm here because I'm a fan of your writing. Otherwise, I wouldn't be here.
56:24So you have increased your odds of something good happening in some indirect way through your blogging, which is exactly why I do it, by the way. So I blog because it has produced requests from the Wall Street Journal to do things. Book deals have come out of that, licensing deals. And I don't really plan any of that. Those are just the things that happen. You're absolutely right. And it's specifically, by the way, when I added the danger component that all my opportunities opened up. Before then, I would kind of write about business or stocks or whatever, but it was very mainstream and nothing.
57:02It meant nothing to anybody. But once I was really kind of revealing personal things and like you say, embarrassing things, suddenly everybody wanted to, you know, opportunities were literally thrown at me. I had to learn how to say no before I was saying yes to everything. Yeah. Yeah. You made it personal. That really made a difference. And how personal is Dilbert to you? Well, you know, Dilbert is a big part of my personality put into the character. So these socially awkward parts, the part of me that's, you know, half robot half the time and I tend to look at the rational side and discount the emotional, you know, magical side.
57:42So he's a lot of me in there, but he, you know, I don't have his engineering or math skills. So, you know, I'm not compatible that way. And then the other characters have some aspect of my personality that I exaggerate because it's hard to rate someone else's personality. You have to find something about you that works for that character. No matter how ambitious you are, you certainly can relate to trying to get out of work and being lazy. So I put that into Wally. So there's always some flawed part of my personality I can capitalize on. It seems like with your blog, the way you kind of inject danger in there, is not necessarily being too personally revealing, but you really play with ideas.
58:29And you take ideas to an extreme and kind of see how people react to it. Whether you're talking about Israel or are we a two-dimensional experiment or whatever, you play more with ideas and kind of test the reaction of people. And I'm curious how much you take it to an extreme on purpose to see if you get huge reaction versus little reaction. Well, some of it is, of course, theater in the sense that if it's not interesting, no one's going to read it. So, yeah, I do pick headlines, for example, and blog titles that try to draw people in. So there's a little bit of sensationalism. But I try within the body of the thing to stick to facts and to stick to reason and to call out when I don't know something.
59:15But what's interesting about my writing and the thing that gets me in the most trouble is that the world is so accustomed to people being on one side or the other side that typically what I do that causes the most trouble is I say, well, there's a little bit of a point on this side. There's a little bit of a point on this side. And maybe there's something in the middle you hadn't thought about yet. And man, both sides hate you when you do that. Yeah, they can't handle that because unless you agree with them, you're wrong. Yeah, it really doesn't go beyond just what you said. So that's the danger.
59:49And it took me a while to drive away the blog readers who couldn't handle that. But I think I have at this point. It's interesting because I specifically do more of the personal stories as opposed to the opinion stories because people just go insane. It's almost like you're contributing to the mental illness of society by forcing them to argue with you. My favorite in the making trouble genre was recently when I hypothesized that the stock market could go to a new permanently higher earnings multiple and stay there if you drove out some of the risk. and the risk that I identified was the risk of all the professional advisors who were largely scammers and idiots and using luck and trying to sell it as a skill.
1:00:40So, I mean, that got me invited on CNBC to talk about it more. And people can't handle that. I've written that exact topic. There'll be thousands of comments saying, oh, he's just a loser who wishes he could make it in the stock market. Like when it's so clear, I've actually run a fund of hedge funds investing in other hedge funds, maybe nine out of the 12 hedge funds I invested in were shut down by the SEC for being criminals. So yes, I'm a horrible investor in hedge funds, but also they're mostly criminals. That's funny. I've never heard that statistic, but from the first probably week I heard the phrase hedge fund, I remember my BS filter going, huh, it's a thing that's not terribly well-defined, that involves a lot of money, and maybe there's some secret algorithms.
1:01:32Just saying. Just saying it might be bullshit. Well, I mean, I had one hedge fund where the guy specifically admitted and the filings are all there. He stole$10 million from the hedge fund. He paid a$50 ,000 fine to the SEC. And now he's on Facebook posting pictures. He's on the beach. He's having fun. Life is good. Well, I think the moral of the story is start a hedge fund. I think I might do that as soon as we're done with this podcast. The Dilbert Fudd. I have to say, ever since 2011, I've had your essay, How to Get a Real Education, hanging up near my desk, because it's so in line with how I think about education.
1:02:13Like, what do you actually, people don't realize the kind of history of the university. Back in the Renaissance, they used to have guards surround a university, but the guards would face inwards because people knew that who committed violent crimes? Young men. So the guards would have to keep people in the university so they wouldn't go out and commit violent crimes. Then the university became something other than what it was then. But I still think the same thing. Like, what do you actually remember from college? Like, you wrote about what you learned from college. It has nothing to do with what you learned in classes.
1:02:52Yeah, I mean, I'm a fan of the general idea that anything you do that's kind of difficult is going to make your brain a more capable tool. So from that sense, it didn't matter that I remember too much specifically from college. It just mattered that it made my brain a better instrument. But I do ask the question, is it necessary that I learn nothing? I mean, couldn't I at the same time, couldn't I have learned something useful? I mean, was that against the rules? Or maybe something I would remember. Yeah, so I think there's a, like you say, almost everything in our world right now is some kind of legacy system that if you were to imagine it and invent it today, it just wouldn't look like what we're living.
1:03:38No, and you bring up that point, too, in your essay on running for president. When you announced you were going to run for president in 2011, you brought up a lot of ideas that, you know, politics is almost an incremental system. Nobody ever thinks of actual, real, let's start from scratch and make this better. People say, oh, let's just make a bill to reform it. And they don't actually do anything. I'll tell you, nothing makes me crazier than hearing somebody argue, usually on the internet, that something is in or not in the Constitution. Because it's a piece of paper written by a bunch of guys 200 years ago who were pooping in holes in the ground.
1:04:20And Mosul-Mond slaves. Mosul-Mond slaves, right. So the question is, what should it be? Not what somebody wrote down 200 years ago. I don't care. I have to deal with that because that's my reality today. But why can't we talk about what it should be starting from scratch? Because we can start from scratch if we want to. It's funny. Last year, just as a spoof to market a book, I was going to run for Congress. And I actually seriously looked into it. But my whole thing was I was never going to go to Washington, D.C. I kept trying to explain I'm going to stay here. And the idea is I'm not I'm never going to go to D.C.
1:04:55So no lobbyists can find me. And but I ended up not doing it. But then I made the not doing it the marketing trick that I did for my book. So I like that. You know, and if you've read the blog, you know that I've talked about lots of different governmental tweaks and ways you could fix things. But I have thought it would be interesting to run for president under the idea that you would just support the majority on all social issues, period. And when the majority changes, you'll change with them because, you know, it's social. And the fact is, the majority is going to get its way, right? So you might help argue against the majority while supporting it at the same time.
1:05:35I mean, you might have a moral problem with the majority. But I think as president, you ought to support it, at least for the internal stuff. And then for defense stuff, of course, you've got to be a little more independent to react to media threats and stuff. But for the domestic stuff, why couldn't you have a president who just says, show me the polls? That's what I support. Yeah. I always wonder why we're not voting on the internet. Like, why do we have to go someplace to vote now? Well, you know, the argument is usually that it wouldn't be secure. And again, I go, ah! First of all, like it's secure now, because I don't know where all those votes go to, but I'm sure it isn't like infinite monkeys with a tally sheet and a piece of paper.
1:06:17All that goes into a computer somewhere, right? I mean, ultimately, I don't know how the system works, but somewhere there's a computer that's all going into. Now, maybe you create more opportunities for problems if you make internet voting, but I would think as long as the news media could do polling in the same places that are doing the voting, that discrepancies would jump out, obviously. I think the main thing is people are really against majority rule. They actually think that having elected officials solves the problem of how bad it could get if there was majority rule. Well, yes. I think there was a time when majority rule would have been the worst thing in the world because you have mob rule.
1:06:58And there's a reason that the United States is a republic and not a true democracy. But I think that the internet makes a lot of those things lesser important, meaning that I can't think of anything that the majority is in favor of that would be awful. Can you? I mean, because there's no majority saying, there's no white men who are saying, let's kill all the Ethiopians who are in this country, or whatever, I'm just making up stupid examples. But we imagine that could happen, but I don't see any signs of that happening, because at this point you couldn't go public on the internet and say, I'm against any group, because you would be smashed.
1:07:46Well, let me ask you a question. Do you think there are even more than three issues that are domestic issues that people even care about? Well, individually, yeah, if you count taxes as everybody's issue and then throw in maybe abortion as the next one, yeah, you run out of issues pretty quickly. Yeah, so okay, taxes, abortion, and then for some small amount of people, for people who live in Texas, immigration. Yeah, or gay marriage, I suppose, for some people. Yeah, but yeah, it's around three. It's a different three maybe for different people, but yeah, probably three. And think about it. All those issues don't actually affect you, like you personally.
1:08:25Well, yeah. Except for maybe taxes. Yeah, some of them affect me personally. Well, Scott, I really appreciate you coming on the show. It's been such a pleasure. I've been such a fan for so long of Dilbert and all your writing, and I'm really grateful you came on the show. Thanks, James. This was a lot of fun, and it was great meeting you, and thanks for having me on the show. Yeah. All right. Good. I will talk to you soon. All right. Take care. Bye.
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From the publisher
A Note from James:
You know, I’ve known Scott Adams for probably 12 or 13 years. He was one of the first guests on this podcast, and he’s the creator of Dilbert, which was my favorite cartoon strip for decades. But then, starting around 2013, he started writing about his life, his opinions, his approach to life, and what made him a success. The first book he did in this genre was How to Fail at Almost Everything and Still Win Big. He also wrote another book that was very influential, called Win Bigly: Persuasion in a World Where Facts Don’t Matter. Both of these books are must-reads.
Win Bigly is the best book ever about real-world persuasion. And Scott Adams himself was kind of an—I don’t want to say he’s an amateur hypnotist, but really more like a professional—in terms of how he used hypnotism techniques for persuasion. And How to Fail at Almost Everything and Still Win Big...when this comes from the very first podcast I had with him—how his story of how Dilbert became a hundred-million-dollar success… he was failing constantly. And the story of the success of Dilbert, which he tells in this episode we’re going to show you now, is just amazing.
Scott Adams has more recently become known for his political musings. He had a daily podcast, Coffee with Scott Adams, which I regularly listen to. I would say over the past decade—or 13 years, 12 years—he has not only become a great friend, and even somewhat of a mentor to me, but we’ve talked a lot, on and off the podcast—his podcast, my podcast—and he really helped me out through some times when I was a little upset about different things. He really knew how to reframe problems so that they would become successes.
And when I first heard he was sick—this was last June—I was devastated. And of course, he prepared us all that he was going to pass away, which he did a few days ago. It was really upsetting.
And, you know, I hate when people kind of take advantage of someone’s death by saying, “Oh, I knew him great. He was my best…” blah, blah, blah. I just want to tell you: listen, put aside all your opinions. He was a great artist. He was a great storyteller. He had opinions you may or may not agree with, but he really knew a lot about the DNA of success and the real mechanics of persuasion—no BS, no academic stuff—just really how to do it.
I would really encourage you: you could better your life if you read his books.
I love this guy. I’m really sad he passed away. I’ve learned so much from him, and I want to share a little bit of that in this episode. Maybe we’ll even do another one at some point. But, you know, rest in peace, Scott Adams. And please, if you haven’t learned from him in the past—or even if you have—we had a great time whenever we talked. And here’s a piece of that.
Episode Description:
Scott Adams (creator of Dilbert) explains why he thinks goals can actually make you worse off—and why systems, energy, and probability are the real tools for building a career that lasts.
He tells the story of how he broke into syndicated cartooning after repeated rejection, and how a small nudge from a stranger kept him from quitting too early.
James and Scott talk about writing with “danger,” why people can’t reliably judge good ideas, and how persistence becomes easier once you stop expecting a perfect plan.
They also get into the emotional side of “making it”—including why success can feel disorienting when you hit a milestone you thought would solve everything.
What You’ll Learn:
- Build systems instead of chasing goals, because the target will move before you get there
- Increase your odds by trying many small bets, rather than staking everything on one “perfect” plan
- Write with an element of risk—if you’re not at least a little scared, it’s probably too safe
- Don’t trust friends (or investors) to recognize a good idea on sight—nobody can predict outcomes reliably
- Protect your energy and schedule your hardest creative work when your brain is actually sharp
Timestamped Chapters:
- [03:04] A Note from James: why Scott mattered, and why this still holds up
- [06:50] Scott’s new book, Dilbert, and why “systems beat goals”
- [12:26] Scott’s daily routine and how he actually creates cartoons
- [15:22] The real Dilbert origin story: rejection, Jack Cassidy, and persistence
- [22:12] “Danger” in writing: why safe content gets ignored
- [25:01] The strange downside of success: when purpose evaporates
- [30:09] Passion is overrated: why momentum beats motivation
- [33:02] The math of luck: a thousand 10% chances becomes a near guarantee
- [34:45] Talent stacking: combine mediocre skills into a rare advantage
- [37:03] Energy as the real multiplier: sleep, food, exercise, and timing
- [41:53] People can’t judge ideas: why “bad ideas” still have value
- [45:13] The Spider-Man problem: responsibility after you’ve “made it”
- [46:01] CalendarTree: solving a small scheduling problem well
- [52:42] Why James’s biggest opportunities came from writing that felt risky
Additional Resources:
- Scott Adams — Coffee with Scott Adams (official community site)
- How to Fail at Almost Everything and Still Win Big — Scott Adams (Amazon)
- Win Bigly: Persuasion in a World Where Facts Don’t Matter — Scott Adams (Amazon)
- Dilbert (official site)
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