🎙️ Curiosity, Creativity, and Careers with Buster Benson

David speaks with Buster Benson, an entrepreneur and former product leader at Amazon, Twitter, Slack, and Patreon. He writes for Medium and busterbenson.com and is currently the CEO of 750words.com. He is the author of ‘Why Are We Yelling? The Art of Productive Disagreement.’

They talked about:

🌱 Having a positive mindset despite early experiences

💻 The influence of the internet in transforming career opportunities

📝 Buster’s journey in writing and building his career

🔍 The power of following your curiosity

🌐 How the Internet is reshaping our world

💡 The inspiration for writing 'Why Are We Yelling?’

🎙 Listen to your favourite podcast player

🎧 Listen on Spotify:

📹 Watch on Youtube:

👤Connect with Buster:

Twitter: @buster | https://twitter.com/buster

LinkedIn: https://www.linkedin.com/in/busterbenson/

Instagram: https://www.instagram.com/bustrbensn/

Website: busterbenson.com

Book: Why Are We Yelling? | https://amzn.to/3QmkJ1a

📄 Show notes:

[00:00] Introduction

[03:14] Buster's personal background and upbringing

[04:28] Positive mindset despite early experiences

[06:15] Buster as an introvert and his journey to find friendship and authenticity

[07:52] Early discoveries on the internet

[09:12] How Buster used the internet as his career opportunity

[10:17] Becoming a creative writer

[11:39] Career as a novel writer at NaNoWriMo

[12:38] The early days at Amazon

[17:29] The road to become a generalist

[19:57] Having the immigrant mindset

[21:19] The upside and downside of following your curiosity

[21:53] Buster's motivation in following his curiosity

[26:45] How the duality of the Internet can change the world

[29:56] Buster's inspiration to write 'Why Are We Yelling?’

🗣 Mentioned in the show:

David Letterman | https://en.wikipedia.org/wiki/David_Letterman

Trade Wars | https://en.wikipedia.org/wiki/Trade_Wars

Diaryland | https://members.diaryland.com/edit/

LiveJournal | https://www.livejournal.com/

Amazon | https://www.amazon.com/

NaNoWriMo | https://nanowrimo.org/

AdFarm | https://adfarm.com/

HabitLab | https://chrome.google.com/webstore/detail/habitlab/

The Locavore | https://thelocavore.in/

750 words | https://750words.com/

Macintosh | https://www.techtarget.com/whatis/definition/Macintosh

Atari computers | https://atari.com/

Cognitive Bias Cheat Sheet | https://busterbenson.com/pile/cognitive-biases/

👇🏾

Full episode transcript below

👨🏾‍💻 About David Elikwu:

David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.

🐣 Twitter: @Delikwu / @itstheknowledge

🌐 Website: https://www.davidelikwu.com

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📜Full transcript:

Introduction

[00:00:00] Buster Benson: I realized sort of in year five or six that I didn't want to be there. I didn't want to like, climb the, the ladder. For a while, that was interesting, and then I was like, instead of climbing the ladder, going back to like my turning things into games, like I wanted to be a level one everything. I wanted to be a level one marketer, a level one designer, level one software developer, level one project manager, level one manager. And I actually told my bosses at the time and he was sort of like, okay.

So I was like, I love that because you know, that was a big gift for me to first like realize that's what I wanted and then to be in the place that was so perfect for learning all these different skills. And to have a manager that was willing to sort of entertain it, and then to be paid a lot of money on top of that.

This week I'm sharing part of an older episode with Buster Benson, who is an entrepreneur and former product leader at companies like Amazon, Twitter, Slack, and Patreon. Buster has also built and co founded several incredible businesses like 43things, [00:01:00] healthmonths.com and currently he's the CEO of 750words.com which is a writing tool that I've recommended to a ton of people in the past who are looking to build a writing habit online. Buster also writes on Medium and he's the Author of Why Are We Yelling? The art of productive disagreement.

So in this part, you're going to hear Buster and I talking mostly about his career. We talk about how he cultivated a positive mindset, despite some of his early experiences. We talk about the influence of the internet in transforming your career opportunities. We talked about Buster's early journey in writing and building his career, the power of following your curiosity. We talk about how the internet is reshaping the world and the inspiration for his book, Why Are We Yelling? So overall, I think this is a fantastic episode.

You can get the full show notes, the transcript, and read my newsletter at thenowledge.io. And you can find Buster online on Twitter @Buster, and I'll have links to all his stuff in the description.

So if you [00:02:00] love this episode, please do share it with a friend. And don't forget to leave a review wherever you listen to podcasts, because it helps us so much to find other listeners just like you.

David Elikwu: I'm really interested. I didn't know where to start with you actually, because you are extremely, I want to say vulnerable online. I don't know if that matches your perspective, but even just looking at your website, like forget about, you know, like Twitter and all the other spaces that you're on, just looking in your website, there's a plethora of stuff and information. and almost anything that everyone could wanna know about you is there in some form. And it was weird because, okay. I knew we were gonna have this conversation. I didn't wanna look at too much of it. I was thinking of, I think it's David Letterman, who was like this

Buster Benson: It's all there. You wouldn't have to have me here. If you had looked at it all.

David Elikwu: Yeah, exactly. And he just wants to be led by his curiosity and, and see what happens.

And so I kind of wanted to do that, but simultaneously you have this really great, page. I think it's like your about me page, which has like this [00:03:00] graphic with all the, the time of your life. And that seemed really interesting to me. And so I thought maybe we could talk up by out, or could start with your background and your upbringing and then see what threads we can pull on and see where that goes.

Buster's personal background and upbringing

Buster Benson: Yeah, well, I'm old. I'm I'm 45.

And yes, I do have a page on my website that is, has mapped up my entire life up to this week for every single week in my life there's a box. And the boxes start from, you know, when I was born in May of 1976 to when I turned a hundred years old 20 76, because I have a goal to ride a bike around the block on my hundredth birthday.

That's my one, like always always present life goal, because everything else can sort of be hung from that in some ways like my health, my relationships, my mental capacity, my stress. Just get me there, I just wanna have a long life that is by the end of it. I feel like I I'm still living a quality life.

So that was, I think, a lot about death and I think a lot about life as a result of that. And this, [00:04:00] this maps. So I, you know, I grew up in Southern California. I was raised with, you know, a Japanese mom and a white dad, and he was into computer science. He was an engineer. And so I had a pretty standard, like middle, upper middle class life had good schools did okay in school.

I never wanted to get A pluses or A's like I always wanted to get the, a minus for the maximum, like effort to reward ratio there.

David Elikwu: Could I, just double click that quickly?

Buster Benson: Sure.

Positive mindset despite early experiences

David Elikwu: How was that impacted by, you know, was that maybe just your upbringing in terms of like, how you were brought up, where you had a freedom to do that, or was that more just an intrinsic, 'this is how you are' and you wanna impose that on the world?

Buster Benson: I've tried to tease this apart before to understand like what, cause I have a kid now I have two boys, 11 and five, and I'm trying to help them like sort of find the same mindset that I had found early in my life around seeing things that could be a drag, like school as games. And so I saw school as a game where my [00:05:00] goal is to do enough, to get an okay grade and then to also pursue my interests.

So I was always twisting the assignments to do what I wanted to do. And for the most part, teachers or professors have always been pretty amenable to that because you know, the good teachers want you to just enjoy learning. So it worked well for me.

Yeah, so I, I don't know how it came about, but definitely was a formative, sort of pattern throughout my life, throughout my early school, my late school, my early career, my late career. And even now where I think about things, not as like you walk into a university or you walk into a new workplace, you don't just assume that you're gonna take on all of the rules and all the, all the assumptions and the, the tricks that you need to do. Like you have to make it your game first and then sort of figure out what you're gonna do within your own context.

David Elikwu: I'm interested in, like, compared to maybe your peers? I know that Irvine, particularly, maybe around that time is very, you know, like loose and I don't know if [00:06:00] I'm using the right words, but like a, you know, very adoptive place to be in the world at that time.

And I'm interested to know, were your peers like that? Was that something that was just unique to you in terms of like your own perspective or was

Buster Benson: No .

David Elikwu: that was like part of the culture? Okay.

Buster as an introvert and his journey to find friendship and authenticity

Buster Benson: Yeah, no, I was, I would classify myself as an extreme introvert early childhood and all the way up through to probably middle of high school. Like my nickname was silence in school, because I just didn't talk. I didn't want to talk. I was too nervous to talk to anyone. I wouldn't like go up to the counter. I wouldn't ask if I didn't understand the assignment. I wouldn't ask the teacher, you know, those kinds of things.

So my friends, I always was just scrambling to have friends in the first place and by the time I did find my crew sort of like in the middle of high school, it was cross country and track and we didn't really bond on academics so much as lifestyle philosophy, that kind of stuff. And I did finally really like find a really close group of people that did share my values and shared my sort of approach to life. And many of those people, I [00:07:00] think good hand, like five plus of them are still really good friends today. So when I was 16 to where I am now, like I might not have changed a whole lot cause you know, we were all still really close. And we shared some of the same stuff.

So yeah, I guess in some sense, like I spent many years struggling and then when I found my, my people, then I sort of realized, well, I can be this kind of person. I'm not just like trying to survive. I can actually just be myself and that was really important.

So that could going back to your first question it to sort of speak to why I'm willing to be authentic on the internet, because I felt like it was a hard lesson for me to learn, to be authentic in real life with my peers and my family, with my friends. And I saw the internet as sort of an extension of that.

Once I found it is that, there is a lot of reward to being yourself. Like there's a lot more to win or to gain from being yourself and projecting that outwards than there is from hiding it and forcing people to try to guess who you are.

Early discoveries on the internet

David Elikwu: Okay. Maybe the next question that I'd ask off the back of that, I'm really interested to know, what were your first experiences like on the internet and [00:08:00] what were the first places you explored? And I don't mean to ask that in a, like a patronizing kind of sense like, when did you first discover it, but I'm really interested to know, I think there were so many internet subcultures and you were like right in the heart of it, I think pretty much throughout your life.

So I'm interested to know, like, where were the places that you explored and what were the maybe knock on effects of that?

Buster Benson: Yeah, yeah. My father was into computers and you know, that was a job. I was very anti them for a long time. But I, I was around them my whole life. I played a lot of ultimate online kind of games like you know, sort of like these role playing games on the computer that you put an eight floppy discs in your computer and, and play them.

And then when BBSs come out, I played a few like sort of networked. What was the game? Trade wars was a big one of like, just buying and selling stuff in a shared community of people that you don't know. And I was very much into like video games and stuff. So when I believe the first, my first real, I remember I got my first email address after I graduated college.

So I was sort of late, like 98. And then immediately jumped onto Diary Land, Live Journal, and these kinds of journaling [00:09:00] websites that were really just about, like posting gossip on the internet. And quickly sort of learned how to make websites from that. Just like, cause I want my blog or my website to be interesting.

How Buster used the internet as a career opportunity

Buster Benson: So I would just always be trying to innovate on that stuff. And that's what got me into ultimately like web development, programming, computer science, and eventually that be came my job for a while.

I was immediately drawn to not necessarily the commercial aspects, but the community aspects, the year 2000 blogger and movable type and gray matter. And all these things were coming out to like software. We had to download the computer that would FTP files to the websites and usually break.

Yeah, I was really into that, that was my introduction. And at the same time I worked at Amazon. So it was like the polar opposite of like selling stuff on the internet. And those two things sort of just sort of fused into like on one hand it's like publishing, authenticity, people, other hand it's like data, security, transactions expand, just like growth, money, all that stuff.

And those two forces have been like [00:10:00] sort of battling in my life for another the next 20 years until I ultimately got spit out the other side. And I'm now very much back to like my original intent of like wanting to build a web that is more about bringing out the best of people than bringing out the money from people.

Becoming a creative writer

David Elikwu: Yeah, that's you made a really good point and I think there's two threads I'd love to pull on and I'm not sure which to go with first. So you did a degree in creative writing, you mentioned, you know, coming across live journal and starting this, being able to write online and having that creative streak.

Was that where that started, or were you already having like a tingling of writing before that?

Buster Benson: Oh, I was, I was a creative writing. Yeah, like you said, graduate. I was working on my great American novel at the time. Had the whole system, it was my whole identity. Like I'm writing a novel, it's gonna be, I was planning the whole thing out. I had all these notebooks, I would do certain number of pages per week.

And then I really, I don't know, 23, 24 year olds that are like trying to write the great American novel. You realize like, there's just not enough material in your, in your head to do [00:11:00] that. So I ended up trying this thing called NaNoWriMo, which was, I just happened upon it as like this national novel writing month of November and ended up writing a couple novels that way, which I really, really enjoyed, because it was just like these brain dumps of like where I am now, rather than trying to like write something that's, you know, of the caliber that's beyond my reach.

So again, like finding these constraints, finding like what is the right tool to like bring out what I'm best able to do right now? I thought NaNoWriMo, was a great one for that and that sort of translated to publishing online. I love writing. I love, you know, conversation and putting it up on the internet where anyone could read, it seemed like this magical shift in the world. And I was all there for that.

Career as a novel writer at NaNoWriMo

David Elikwu: Can I ask when you started on NaNoWriMo?

Buster Benson: Yeah, I did the first one in 2000 and the second one in 2003. Eventually when I moved down to Berkeley, I was in Seattle. At the time I happened upon someone that knew someone that worked at NaNoWriMo, it was like sort of a nonprofit and it was a few blocks from my house. So I had to go meet them. And I was on the, board, ended up being on the board for [00:12:00] a while because of my work with 750 words and a couple other things.

But I love that organization and I think they're still amazing. Yeah, if only more of us could just put everything aside for a month and write a novel, I think it would be better, you know, it's a big ask though.

David Elikwu: It is a big ask. So I've tried NaNo eight, no seven times. I didn't get my eight-peat, but seven consecutive years, I think starting in 2012 for eight years,

Buster Benson: Wow. Awesome. So you've done it seven times.

David Elikwu: I've tried it seven times. I've completed it twice in terms of writing 50,000 words. And then the third years I was working in corporate law at the time.

The early days at Amazon

David Elikwu: Funnily enough. So, okay, and, and I guess maybe then from here, we'll go back to your early Amazon days. Cause I have some questions about that, but that's one thing I found interesting that I tried NaNoWriMo twice in the two years before I started working in corporate law. One of those years I was unemployed and I could barely write more than maybe 22,000 words. I don't know what it is about having all the time in the world, but I couldn't see to, [00:13:00] to use it productively.

And then as soon as literally my first year in corporate law at one of like the biggest firms in the world where you're doing all these hours, suddenly I write 50,000 words and I do it the next year again, and the year after that, I almost did it. I think I got to like 30,000 words, but that month I was also averaging something like 95 hours a week. And so I just, I shut down, I quit a week early and I was like, this is too much.

But the point is that those three years consecutively, I wrote more than I had maybe even in the two previous years combined.

[00:14:00]

Buster Benson: Yeah. Yeah. I can relate. I think I wrote both my novels while I was at my desk at Amazon. So I think it might have been different because I was working a lot of hours I think, but not working like my heart wasn't into it as much. So I think there was a, a mix of that. There's a lot of people that are, you know, clocking the hours, but not doing the work.

David Elikwu: So what was it like maybe, okay. Coming into Amazon, first of all, like what was that journey of, of getting there? And then the second part is, you know, what were those early days like both professionally in terms of what you were doing for work, but then also, I know you mentioned kind of this maybe tug internally of finding the balance between like your creative pursuits and the things you actually care about. And then the job that is maybe [00:15:00] putting food on the table,

Buster Benson: Well, there's so much, so much there. I was, I was there for five years from 98 to 2006. Yeah, I've been, I've worked closely with them past that. So I sort of see that as like the cauldron that my career DNA was formed and it's not what you might expect from that statement, I guess.

So early on it was a startup. It was, I think there were like 2000 people when I joined. I was on customer support, so I was just answering emails and phone calls and, you know, doing it on the night shift. So I was, you know, doing it for people in other parts of the world.

And it was scrappy, it was just like, everyone was just excited about the internet. And I was there to like help people walk them through how to like use a browser and it was great. I was really into it. I felt like the money was ridiculous because you know, being right outta college as with bachelor's in creative writing, I did not expect I was working at the, at the art museum before that. I did not expect to be making I think it was probably like $20 an hour plus overtime, which there was plenty of and I was like, wow, I'm awash in money. What do I do? But yeah, it was so fast-paced, I was working 80 hours a [00:16:00] week. Like most of people back then it was just books and music and they launched auctions and then video and then more and more of that.

Like I told you, I sort of like, I scrapped myself like into like someone that could write code too. So I was publishing like intranet pages and learning that on the fly and it was fine because nobody in the world was trained as a web developer. And I just happened to be in this place where they were basically internally training everyone how to do this stuff and I just on jump on that bandwagon and I loved it. Lot of those people are still my friends too. Like a lot of those people are like people and some of them still work there.

I saw the shift when my job stopped being like I was on the personalization team. So doing things like similarities and shopping cart recommendations, that kind of stuff. And I just saw the pattern I saw like, okay, the way this works is you just take what people do. You put it into the algorithm, you show them stuff that's slightly like that. And you're gonna make endless money. And I just got bored with that and I was like, my last. I went from customer support to trainer, [00:17:00] to web developer, to program manager like had a technical product program manager to software developer. And then by that point, I was like, I can't do this anymore. I'm too bored. I learned everything. I thought I need to learn to start my own company. So I, I went and did that after that.

The company is now is like so different from what it was back then, but it was, it was formative in the sense of like, I saw this open wide vista of possibility. And even though they chose the path that I didn't want to take necessarily, I still see that there's that possibility there

The road to become a generalist

David Elikwu: And so you touched on the fact that I guess during that time is you were also starting to build your own things and you maybe built a few, projects during that time. And I think you also published one of your NaNoWriMo during that following decade well.

Buster Benson: It's been enough years now. I could tell some of these stories. I built a text ad service for blogs. So like really medium sized blog to be like, a direct, like you could buy for $5, you could buy a text ad to go on other people's blogs, if you have JavaScript. And was running that like, [00:18:00] in some cases like, I'm I know under my desk in some at the time, and I built a thing called the, the idea.

So I was building a lot of, I was learning pearl at the time and I was learning like how this all works and just I loved it. A lot of it was like flashes in the pan, like the text ads was called, what was it called? Ad farm. Like it blew up, it got like featured on um, something ugly and suddenly my servers all melted and I was like, oh shoot, I can't do this. So I had to turn it off.

But many of my, like, I, I was in this pattern of building websites, seeing if they worked, seeing if I could sustain them, seeing if I wanted to keep working on them and then, you know, nine outta 10 of them don't and then some of them did. Some of them are still around.

The last thing I'll say is that, I realized sort of in year five or six that I didn't want to be there. I didn't want to like, climb the, the ladder. For a while, that was interesting, and then I was like, instead of climbing the ladder, going back to like my turning things into games, like I wanted to be a level one everything. I wanted to be a level one marketer, a level one designer, level one software [00:19:00] developer, level one project manager, level one manager. And I actually told my bosses at the time and he was sort of like, okay we can't do that officially, because there's no career thing that says that, but like unofficially, that's your job. And if you want to like go embed yourself on this team and learn marketing, you can do that for a month that you can do it for.

And to this day I still like I think of myself as a generalist. Whenever I need a job, I will like narrow that down into something that can get a job, because people don't like to hire generalists, but that's how I see myself as just someone that's interested in. How the things connect and not, not, I mean, I like the details too, but I tend to hop from vertical to vertical to like understand them better.

Having the immigrant mindset

David Elikwu: No, I love that. And I absolutely agree. I think funnily enough, that [00:20:00] is almost word for word, something that I talk about on the course that I run. But just also in general, maybe like on, on Twitter and, and spaces is this idea era of, first of all, I love the idea of being a generalist, because I think that fits me very well, similarly.

I don't know if I've necessarily had the opportunity to have a boss that says, you know, you can just go run around and learn whatever you need to learn. But I think I've been able to build that in a way like throughout my career as well. Like I started very early on, so I taught myself like some design and I used that design to get into marketing and I did some like very early marketing. But I think okay, long term, this is like the immigrant mindset, I wanted to go into like some kind of profession so I was like, okay, I'm gonna be a lawyer. That's what I'm gonna do, but I'm gonna like pursue all these other things on the side. So I'm still doing like some marketing jobs and still doing some design. I'm building websites, doing all these random things on the side.

And then I think I started consulting for startups. Maybe I launched one or two things of my own. I also like previously built a business. And so I think as you go on, you are like accumulating information [00:21:00] through your role. I think you maybe get some knowhow from what you're doing and, and particularly for you, I mean having the customer success element, having some marketing element, having product management and then building all the projects, you're getting all of the tools and the skillset, and then being able to experiment wildly and, sow some seeds and see what grows.

The upside and downside of following your curiosity

Buster Benson: I think it's a very privileged sort of cursed path that I've taken, but there's downsides as well, I think, but the upsides are really just being able to follow curiosity, you know, to follow, like when you run into a problem, like not having to find a person that can solve your problem, but trying to be having the tools to figure out the problem. Even if it's in a different domain, I think is really valuable in a lot of ways, because life is sort of chaotic and we end up needing to, so it's so much faster to find an answer than to find somebody with an answer sometimes. But that could be also my introvert side speaking a little bit too.

Buster's motivation on following his curiosity

David Elikwu: Yeah, with those early projects, was it more like, what was the motivation? Were you just following your [00:22:00] suriosity and just like, you know, pruning some different, different fields and seeing what stuck or were you actually trying to find one key thing? Like there's something you wanted to knock out of the park and you were just testing lots of different things to see what really struck gold.

Buster Benson: I think while I was at Amazon, I was really trying to find a way out of Amazon. So I wanted to of the start company. I was experimenting with a lot of different ways of, because the internet was still, you know, extremely new. The tools were still barely working but I was at the, the frontier of that and I could sort of see like be the first person to make the connection.

So my first startup was about like it was called 43 things and it was about making a list of goals and then using the internet to help people find people that have to accomplish the goals you want to do and getting tips from them. And it was a pure, like, you know, blank slate, blogging play, like instead of just writing on a blog, write about your goals and organize everything around what people want to do.

And it turned out to be a really good way to target SEO at the time. Because most Google searches are about goals. And so we ranked really [00:23:00] highly and ended up making a successful business out of it, but then got required by Amazon. So that was the other three years of, of that.

Yeah, so, but then after, after that, I think there was a point when I turned 27 and I always think of 27 because in astrology, even though I'm not really astrology person, like it's like the side of returns, like it's a, it was the year that like many of my favorite musicians killed themselves or died. It's like this year of reconfiguration. And I remember like that year, everything was falling apart. I hated my job. I hated my life. I didn't like myself. And so I, you know, ended up, you know, I was married, I got divorced, I quit my job. I shaved my head. I sold all my possessions. I like left my house. And I made this plan I thousand days to like reinvent myself. And a thousand days, yeah, this is, this could be a long story, so cut me off. But yeah, it was like this moment of death and rebirth, right. Of like, okay. I saw that path. I saw where I was going. I didn't wanna be that person. I'm gonna kill that [00:24:00] guy. And I'm gonna start over. And I actually ended up changing my name, like all three of my names, first, middle and last on a whim to names that, you know, were voted on and coin flipped.

So at that point, that sort of, at the end of that phase was when I realized like my question was, how do we change ourselves? Can we change ourselves? And if we can, how do we do it? Like, is it even possible? Cause I was thinking about a lot of these different things. Like technology is being used to persuade people, recommend things like the internet is being used to form communities and to change behaviors and habits. And I got deep into like quantified itself and all that stuff. And then at the same time had this sliver of like doubt of like, is this all working or is it not working? Is this all just a, a racket to like sell things? And so I tried many ways to change myself. Like, you know, I did a month where I was like, I'm gonna gain five, 10 pounds this month and the next month I'm gonna lose 10 pounds. Things like that, where it's like, not change for a purpose so much, it's changed for change itself to understand like, what are the [00:25:00] levers I need to twist? I mean to understand, like, what are the, like, is any of the habit science legit? So that's when like habit labs and health month and locavore and 750 words even.

And so many other websites that have come and gone came from it's like this sort of pursuit of using technology using the web, using social media, I guess, as a way to like, can accountability, help us change? Can various sort of placebo effects help us change, can social unity help us change and trying to find the answers to those questions.

Yeah, that carried me from like, for another 10 years, I think. I think there's always like this central question and then eventually that changed to something that's more about like, who should I be? Like, how do I, how do I exist in the world without harming things? Because it's not about fixing biases or it's about like repairing, I don't know.

So I'm, I'm sort of in the middle of this question right now. Like how do we add something valuable back to the world without hurting it in the process?

Like I came away from the tech world, I quit my tech job in [00:26:00] 2019, 2018? I think. I don't know if I'll go back because like all this time I've had these ideals going through, working at Amazon, Twitter, Slack, Patreon, each time having the best intentions and each time coming away feeling like, am I making the world worse? Like especially to Twitter, like, I made the world worse. I had good intentions, but like I made it worse.

That fear now of like, it's not about like, can I change myself or how do I change it? Like, who's to say that I should change? Like who's to say that the change I do, won't make things worse for other people.

And so now I, I think a lot about like, self reflection and thinking about like, what are the big ways we could participate in the world while accepting it the way it is, and contributing in a way that doesn't end up, you don't end up regretting.

So yeah, long answer, and there's a lot more detail than there, but hopefully that's the gist.

How the duality of internet can change the world

David Elikwu: Yeah. no, there's, there's so much in there. I'd love to maybe just digging in on that last part. And thinking about your experiences, maybe at companies like Twitter, Slack, like all of those companies are in my mind, ones that have huge promise, and maybe that's kind of what you [00:27:00] went in with is this idea that these are things that can change the world in some ways whether that's positive or negative, but also changed the way that we communicate, the way that we interact with each other, all of them in very different ways. Obviously like slack is maybe more generally geared towards organizations Twitter is, I think in some ways democratizing speech and having this like short blog format, or I can't remember what the in original words were, but like a mini blog.

Buster Benson: Microblogging or I know it's, yeah.

David Elikwu: Yeah, just like a few words and sprinkle them out. But I think it's, and again, I'll, I'll get to your experiences, but I do see that conflict, at least in my own life where I can see on one hand, the destruction that can happen when misinformation spreads and false ideas from spread or not necessarily false, but maybe quite potent ideas spread. And through algorithms, people can be dug into trenches that they can't see out of because everything that they see simply reinforces what they are already inclined to believe.

And then that can also go into like maybe things like beauty and fashion and health, and [00:28:00] there's more and more, we are kind of being groomed into identities that are almost built for us. If that makes sense like that there is that perspective. But then on the other side, I also definitely see.

So I came to the UK from Nigeria and I see this huge tech scene that's now booming in Nigeria and across Africa. And I see people in Kenya, people that are getting access to the internet. And I think maybe this is also the difference where in the US or even in the UK, the first computers were the first computers. And that is how people started with computers is like these really old, like the Macintosh or whatever you know, Atari computer.

But in Africa and maybe India and places now, like people's first computer is a mobile phone. so they are jumping in right into that kind of like last third of all of this history of development and people are jumping in right here. And their first interaction with the internet is getting straight into Facebook and straight into Twitter and straight into some of these other things.

And obviously, okay, there are [00:29:00] negatives and we see like these viral threads where loads of misinformation spreads and it's rampant, but then simultaneously it's like people being able to have a voice and people that this is the only device that they have, and this is the only internet they have and they are on Twitter and they can see everything that we see and interact with everything that we interact with.

So I think it's an interesting duality there where there's this magic and then there's also the capability for maybe destruction.

Buster Benson: Yeah, yeah, yeah, absolutely. I certainly don't think anything can be just labeled as evil. It's really just like the line between good and evil goes through every single heart, goes through every single product, goes through every single service out there. And we can sort of be lured in I mean, I think there are ways to use it to sort of, and push people in that direction of evil or good. But yeah, ultimately there is, you can't, can't just cut anything off entirely. Like, I feel pretty strongly about that. Even if it was possible, which is not I think we have to still deal with the fact that we're part of the problem and we're part of the solution and the same goes for everybody else.

Buster's inspiration to write 'Why Are We Yelling?'

David Elikwu: And I think that leads right into, why are we yelling? [00:30:00] Which is the book that you wrote. I think that was published right around the time that you left your last tech job.

Buster Benson: Yeah, yeah, yeah. I left my last job at Patreon to finish this book, so yeah, I think I, yeah, it was published in 2019.

David Elikwu: Okay. Maybe let's just start with, where did the book come from? Like what was the inspiration? I know some of it I could possibly guess, from your perspective, like where did that come from?

Buster Benson: Yeah, it actually started with a viral medium post. So when my second son was born, I took a month or six weeks off and like to keep my mind from rotting. I think I dove into this cognitive biases. Wikipedia page because it had been bothering me for a decade of like, I don't understand biases. I don't understand why they exist. How are we finding them? Are they real? Like, how are they structured? Why do we have them? How do you fix them? All that stuff. And I could also just couldn't remember them. I couldn't remember like all the different ways. And so I thought I would just like immerse myself in the data which I love to do.

The beginning of any problem I'm just like bring on everything, just pile it on and then feel like the overwhelm [00:31:00] of that and let your brain sort of like digest it and try to make sense of it.

And after doing this for like a month. I came out with like this post, which is called the cognitive bias cheat sheet. And it was like a 17 minute read. It was called cognitive bias cheat sheet. It wasn't made to be click bait at all. Like it was like the most boring post. But for some reason, I think, because it promised like this gem of, of like synthesizing a really complicated topic, it blew up and it's like one of the top hundred medium posts, I think.

And that was really interesting for a lot of reasons. One of 'em being, I don't know, I just wasn't used to like my post doing that. Second of all was like, I didn't understand why it was happening. And third of all was like, book editors started emailing me. Like, you wanna write a book? Like here's a deal. And so I pushed them away a bit because I had newborn kid and I was working and books are hard. But eventually sort of was found an editor that seemed to like, understand how I wanted to go about writing a book, which was not necessarily to sell any books.

My, my [00:32:00] goal was to be proud of writing a book. If it was gonna take two years or 10 years like, I was gonna take my time. And they're being a great editor like accepted that, and also like helped me like form into something that was actually a real book and ultimately did sell pretty well.

But it started about being about cognitive biases. The title was thinking is hard, which is like the subtitle of the blog post. And I was like, who cares? Of course thinking is hard. There's already plenty of books about that. Why is thinking hard and when is thinking hard? And I sort of settled on arguments disagreements as the venue, like the arena where all of our biases were meant to be used, right. It's where they go from, like being sort of in the background to being like front and center. This is what we're doing kind of modules in your brain. And so what do they do for us? They help us in a lot of ways when arguments even if we're not right, they do this by like filtering information, that's not convenient to winning. They help us jump to conclusions, When more data might confuse us, you know, they help us sort of [00:33:00] make sense of data points that don't quite connect, but connect them all into a, a coherent narrative. They help us like, you know, make generalizations. They help us sort of remember the right things to like use later.

So it made sense in that context and it also seemed like a novel book. It seemed like, this is useful for me as a generalist, like arguing is something that everyone does. We can all relate to this. And it's something that, for some reason isn't talked about a lot, like, no, one's an expert arguer, like there's expert debaters there's expert sales people, but there's no expert moderators really up there. And maybe diplomats in theory are, but really they're, they're just fighting for their team still. There's no one that's truly out there trying to connect, build bridges, see common, you know, and to bring us back into a coherent, like cohesive community instead of dividing us.

And so that was like, if I wrote that book, I would feel proud about it.

So I did, and it took, you know, it was like, it was difficult, but that was the genesis of it. And [00:34:00] yeah, I still feel very proud about the book because it, it isn't what I could, I could not have written that without the book. Like I couldn't have written that as a series of blog posts, I couldn't have written on my own. It needed the crucible of being on a book deal with a publisher and a really great agent and a really great editor and like having this really compressed anxiety around the election and everything that was just like contributing to it that made it happen.

And you know, I look back on it saying both like that sucked, you know, that was the most difficult time of my life, but also like at least something nice came out of it something useful.

David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.