The Wealthy Barber Podcast - #41 — Chris Guillebeau: How to Start a Side Hustle

Episode Date: January 27, 2026

Episode #41 is out now! Our guest this episode is Chris Guillebeau — author, entrepreneur, blogger and speaker best known for “The $100 Startup,” “Side Hustle,” and his latest book, “Time Anxiety.” Chris first rose to prominence through his blog “The Art of Non-Conformity,” where he shared stories of unconventional work, travel and building income on your own terms. In this conversation, Dave and Chris dive into the world of side hustles and small entrepreneurship — how to turn skills and hobbies into income, why reselling is one of the easiest ways to start and why action always beats overplanning. Chris shares what successful side-hustlers have in common, how to find your first customers, why farmers’ markets are an underrated testing ground for business ideas, and how knowing when to quit can be just as important as knowing when to push forward. Whether you’re thinking about starting a side hustle, testing a business idea, or just want a fresh perspective on work and time, this episode is full of practical insights and encouragement. Listen now on our website, YouTube, Apple Podcasts, Spotify and all major podcast platforms.   Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Chris Guillebeau (02:05) Chris’s Unconventional Early Career (05:03) The Why Behind Writing “The $100 Startup” (08:06) Turning Skills and Hobbies Into Income (11:04) Reselling is a Great Place to Start for Entrepreneurship (11:56) Action Beats Overplanning (13:06) How to Find Your First Customers (14:45) What Do Successful Side-Hustlers Have in Common? (21:12) The Impact of “The $100 Startup”  (22:09) Knowing When to Quit is Vital (23:40) Farmers’ Markets Are Great for Testing Business Ideas (25:44) Why Enjoyment Matters More Than Scale for Side Hustles (27:16) What is Time Anxiety? (29:02) ADHD & Neurodiversity (33:16) Conclusion

Hey, it's Dave Chilton, the wealthy barber and former Dragon on Dragonstant. Welcome to the Wealthy Barber podcast. Well, we'll be hosting some of the top minds in the world of personal finance. Yes, that's to balance me out. The podcast is about making this subject not just easy to understand, but dare I say, even fun, honest. Whether you're trying to fund your retirement, figure out how to build a down payment, save for your kids' education, manage debts, whatever, will be here to help you.

You do it. Before we jump in, a quick but important note, nothing we discuss here should be taken as investment advice. We don't know you and your personal financial situation. So we're not here to tell you we're specifically to put your investment dollars. We're here to educate, get you thinking, and we hope entertain. But please do your own research and or consult with your financial advisor before taking any action. It's Dave Chiltern, the wealthy barber with the Wealthy Barber podcast. Thank you for all the feedback lately from so many of you. We're up to episode 40-something. Great episode.

I sought this guest out. Aiden and the team normally go and find the financial experts. Of course, I approve them. I often know them. This is a little bit different story. I wanted to get Chris Gillibault, the person you see on your screen, on the show, because I'm a big fan. And also, this sounds corny.

I really felt he could help. I thought it can make a difference with some of the things he was going to talk about. I know Chris through his books. A lot of you know the $100 startup. He said several other books, including a recent release called Time Anxiety. We'll talk about later in the show. I first came across him through his event that he ran in Portland, Oregon, the world

domination event because it drew so much attention. Even the name was very clever. Obviously, it did wonderful things for him on the media front. His background is incredibly compelling. He quit school at 16, but ended up going back, getting two degrees, traveled the world. He's been to all 195 countries in the world. He tells us Canada's his favorite. He actually didn't say that, but I thought I'd, you know, put that.

in to make them look good to start the show out. So a really interesting guy, Chris, start out with the fact that you kind of got involved in the unconventional workspace and then took off from there. You're one of the first people to really go to the blogosphere, do all those types of things and draw an audience that way. Well, thank you so much for having me, Dave. Congrats on 40 plus episodes. And what a wonderful community you have built as well. How I got started. Well, I was an aid worker for a few years in West Africa. as you mentioned, I didn't do so well in high school, though I kind of later went back and, you know, did the college and grad school thing. But from age 22 to 26, I was living in West Africa most of the time and also traveling, you know, to other parts of the world. So those were very formative years for me.

And then I'd also been learning about online business at the time. And this goes back, you know, 25, almost 30 years now at this point. So it's kind of like, you know, the early 2000s. and, you know, the internet and, like, all these new things, like websites and auction platforms where you can go and buy and sell, you know, eBay.com was like this new thing. And, you know, I just started learning about all this. And I really enjoyed just the freedom of being able to kind of construct, you know, my own business, my own life. And I didn't know anything about marketing or copywriting or any of that stuff, but it's just kind of like learned all along the way. And then,

you know, you mentioned the blogosphere. It's interesting because I was coming back. from living overseas and I did this graduate degree and I was like, well, this is kind of interesting, but, you know, I write a master's thesis and I put a lot of work into it and, you know, four people read it, right? Like my four advisors, you know, and I don't even know if they read the whole thing. I was going to say, I bet you're wrong. I bet you two. Exactly. Right. So maximum four people. And around the same time, you know, I saw some friends who later became like mentors and who were writing blogs. I call them friends now, but at the time, I didn't know who they were. It's just like internet famous people. And I was like, maybe there's something I could share as well. And so I wrote

this little manifesto, like an online PDF called A Brief Guide to World Domination. And I just published this. And it's kind of like, you know, some of my experience of living abroad and maybe a different way of thinking about the world and how you can do good things for yourself and for others at the same time. Like, it's not a false choice. And, you know, here's some stories of different people who've done that, you know, just a little thing. And so I put that. And so I put that. manifesto out and it got some attention. And I think over the course of a few months, you know, 100,000 people downloaded that. And, you know, it was a free document. I'm not making any money. But I was very excited because I was like, wow, you know, maximum of four people for the master's thesis, right?

And then I also, I put a lot of work into the manifesto as well and it reached, you know, so many more people. And so that's kind of where I was like, maybe we can do something else with this. Like maybe this is the start of something and not just the culmination of something. So that's kind of, you know, everything kind of developed after that. It seemed like a very giving guy and very passionate and even the way you started out, you know, doing the work you did over in Africa and the difference it made in your life. So you got to that point. But again, where most of us know you or at least came to know you was through the $100 startup. I mean, that book really took off. I believe it got to top 10 in the New York Times bestseller list in times, which is amazing achievement. It had a great looking cover.

I think everybody can kind of envision that cover with the bicycle, et cetera. What led to that book? What was the why behind it? What's funny is, you know, you mentioned the cover, and I haven't thought about this in years, but as you know, probably from your books, covers are a difficult process. They are. We probably had 30 or 30 more covers that did not work for that book, and we didn't like it, and we kind of settled, you know, on the bicycle cover. So I'm glad you think it's iconic.

At the time, I was like, I don't know. Maybe it'll work, but it also shows we never really know. What kind of led to it? So I had a previous book, $100 startup was book number two. I had a book that was kind of based on the blog I was doing called The Art of Nonconformity. And that was the first book. And I did a tour where I went to all 50 states in the U.S. in every province in Canada as well. And I did that just because I had readers in these different places.

And I was like, I want to connect with people wherever they are. So that was also a very formative experience, kind of like living in West Africa, because, you know, I get to talk to all these different people and I hear stories about why they're connecting with what I'm writing, but more importantly, like what they're doing in their lives and like how they're trying to escape, whether it's the nine to five or a conventional life or they want to do something different. They want to travel. You know, they want to start a business. And so I found that really inspiring. And I also felt like nobody was really telling these people's stories because at the time, there's a lot of information about startups, you know, and like

Lean startup was out. Great book, great methodology. But that's not something that a lot of people connect with because it's a Silicon Valley mindset, you know, it's great for some people. But I just noticed, you know, all across Middle America and Canada and elsewhere, there are people who didn't want to attract investors or build out this type of scalable model, but they still like the idea of working for themselves or doing something that they enjoyed and finding a way to make a good living from it. And maybe growing that into a greater business, but maybe not, you know, the whole point is like creating options for yourself. And so I felt like, again, nobody was really telling those people's stories. And so that was what the idea of $100 startup was to tell those stories and to provide

kind of like a case study approach or a case study model that other people could follow. So a little bit of step by step, but also like allowing for creativity, originality, you know, your own personality, whatever is important to you. I thought it was really inspire reading that book. I really did. Like I thought it did everything you just described. It kind of gave you a step by step, but it, you know, there has to be flexibility and creativity, options built in. And but you saw the successes that others had had. And you're right. There's people who want to do that for a living,

but there's also a tremendous number of people in society now in these very tight economic times who want to do it just to make an extra 500, a thousand, 15,00 a month. Because, of course, that can be a huge difference maker for them. In a lot of ways, when I look at what you've talked about, you're teaching people to kind of mix passion and skill and marketing a little bit to monetize hobbies in some respects. Not always. It's not always a hobby, but it often is.

Walk us through maybe one good example to start the conversation that you've seen that kind of captures the thrust. Oh, sure. Yeah. So the thing with hobbies, as you mentioned, not every hobby needs to become like a monetizable activity. It's okay to just do things for fun. But when people are trying to figure out, okay, what is the thing that I'm good at that can be monetized in some way, I do think it's helpful to go back to like what are the things that you like to do and not just like to do, but things that you have a good amount of skill in. And this may not connect to what you studied in. school, it may not connect to what you're doing, you know, in your job. Perhaps it does. So let's see, we've had people who are doing like trading cards. You know, maybe they collected baseball cards as a kid and, you know, later in life they get into like Pokemon or something and, you know, they built, you know, ultimately a six-figure business from that. I had a good story of a guy who learned about drones, you know, when drones like first started, you know, maybe 10 years ago or a little bit more, you know, that was still very new and people are buying drones, but then they

were crashing their drone all the time because it's hard, you know. And so he created this like drone school. And that, I think, actually turned into a million dollar business, ultimately. So, you know, you think about the thing that you're good at. You think about what is it that other people are also interested in, you know, so these are good examples. Lots of people are buying drones. They're crashing their drones, trading cards, big, big market. But it really, it really could be anything. Yeah, that's interesting. I mean, we try to grab examples and I stuck a few in the wealthy barber. You know, we saw somebody who was making bobbleheads. Oh, sure.

Of, you know, six and seven-year-old baseball players. You've seen other businesses doing that now in advertising aggressively, but four and five years ago, it wasn't too common. A local fellow was making crocunole tables. Do you know the game crocunole? Yeah, I don't know it will, but I know it. Yeah. And so he was making crocanole tables and his friends loved them.

He thought, why not start selling these a little bit? And some of the local businesses we've seen thrive, that people are good at building something. And they figured out now that Facebook marketplace and some of these online platforms can be tremendous exposure vehicles. So they aren't spending big money on advertising. They're just reaching out to their local community. They don't have a lot there for in shipping expenses, et cetera. So you must have seen a lot of things like that where people are just good at building a certain something and then they take it to the market. Exactly. Building and then

testing quickly, I think is a really key part of it. So with Facebook marketplace and Poshmark and other platforms, it's very easy and simple, right, to like get something out. And maybe it's not what you are going to do for the rest of your life, and that's okay. I think this is another hangup that people have often. You know, when they're thinking about entrepreneurship with a capital E, they imagine like, oh, I have to make this long-term commitment. And I think it's much more helpful for people to get experience. And with these, you know, marketplaces, you can get experience, you know, very quickly.

I often encourage people to try reselling, you know, if they haven't done anything before. It's just like there's stuff you can buy and sell. And again, maybe that's not your long-term calling in life, but you will get some interesting skill and experience from it. You're going to learn a lot of different little business skills that can be applied in lots of different ways. And it's very low risk. You know, the worst thing that happens is you buy something that's not going to sell for a little while or you lose a small amount of money. But most likely you're going to learn what you like and what you don't like about running a business.

And it will lead you to something different and better. I want to second that one to the end degree. So many of the people who have become microbusiness entrepreneurs started out reselling. and they bought something again on Facebook marketplace, cleaned it up, sometimes didn't even do that, and then resold it. And as you say, you'll learn a little bit about marketing, about positioning, about photo taking, about all of those different types of things. You're very much an advocate of get started.

And so planning matters, but let's do something here. Like the best way to plan is as you go, you're learning from your mistakes, you're learning from what goes well. And I think that's good. I think I've been weak a couple times in my life from over planning, over preparing. And a lot of times you're better to just a job. jump in and get her going. Yeah, and I don't always take my own advice. I feel like I've often overplanned, right? And there are some businesses where it's more important to do some planning

and depending on the nature of your goals. If you want to start a manufacturing, you know, business and there's going to be higher cost and so on. Not everything is going to be a $100 startup, but I do think there's a principle that a lot of businesses can be started very easily and you can learn pretty quickly. I think people get hung up on market testing is another thing that they think, how do I know if my idea is viable? Well, the best way to know, is to try, right? The best way to know is to like, it doesn't cost a whole lot to make a website these days. Also, you know, if you want to go to the next step up beyond Facebook marketplace, pretty easy to make a simple website. You can either do it for free or for a small amount of money. And it might not be the best site in the world, but it's enough for you to, you know, offer a service or a product and see what the response is and then kind of adjust from there. You know, when I talk to people about that, because you're right, you can put together a beautiful website now using AI tools, etc., very inexpensively. But the big question is, I've still got to get to,

people there. And so I've got this hobby that I'm good at. I think that people would like it if they could hear about it. But I can't figure out how efficiently to get in front of them. I don't know how to spend. I don't have big resources here. How do I do that? You found in general that a lot of people, when they just get these products out there, even inexpensively, just the exposure can often build some momentum on its own. Yeah, it really depends on the product, you know, or the service or what you're selling. I think it's helpful to start with who you know. If we're speaking about hobbies, most likely you do know some people in the same hobby or in. industry or you're using Reddit or there's some other forum in which you're communicating with

people. And so you don't want to go on those places in hard sell. But most of the time, if you're active in a community or a Facebook group, it is okay to say, here's my website or here's this new thing I'm doing. I'd like some feedback. Or maybe I'm starting a new service and I would like some test customers or test clients. I'd love to do one audit for free or one, you know, one project for free. I think that's a good start for people. And then, of course, you want to go beyond that. but I think that's helpful in terms of the initial response. You know, you said all that very well, and I find it interesting when you're in chat rooms, and I'm in lots for different, different types of areas.

I like when people are up front, you don't like when people are trying to sell you something or luring you there without being upfront, but when people come on and you can see the passion coming through or they're proud of what they've built or they truly think it can make a difference in your life, I have no issue with that whatsoever. I mean, they're not obligating us to buy. We're going to go and look at the site, and if we're intrigued by it, we can take the next step. And I think, again, being honest and enthusiastic, gets you past some of those burdens.

So what are the common denominators you've seen among some of the successes? I know there's such a wide variety of things people are involved in, but are there certain things you've seen repeat themselves that have led to higher odds of success? Yeah, that's a great question. I think the first thing is curiosity. And so this is a trait. It's not a skill, but it's something you can develop. Like you can develop your sense of curiosity, you know, of asking questions and kind of developing

along the way, like your power of observation, of being able to notice. And you could start by noticing, you know, problems in your everyday life, you know, problems or sources of friction with this particular hobby or this thing you're into or just as you go about your day, you know, what's easy, what's hard. How could this thing be better? And it doesn't mean you're going to start a business, you know, for every problem that you notice. But I think that is a good, like, entry point and a skill to develop that will serve you well

over time. So you have the curiosity, you have the observation. And then the next step is, oh, okay, how can I, you know, how can I learn the skill of, it's not just idea generation because I feel like everybody has ideas and like ideas are just everywhere. And so once you start noticing things and coming up with ideas, you don't have a problem with generating more. I think the challenge is going from idea to ideation or idea to an offer to a service to your product. So it's like, how can you start thinking more in terms of services and products? If you want to have an online

business, that's the fundamental. Like you need some kind of offer. You need a group of people or at least one person who's willing to buy it in some way of, you know, getting their money, whether it's a PayPal account or a Stripe account or something else, right? That's really it. Or Facebook marketplace will facilitate that part for you. So that's what you need. So if you have curiosity, if you have the ability to go from thinking about a general business idea, because every person on the street has a general business idea and that's fine. But what are the steps, you know, to then turn that into a service or product. And then the last thing is probably what you've touched on already is just the willingness to take action, like the willingness to do something about it. Because I'm sure you

hear it all the time from people who have different ideas and they run it by you. What do you think about this day? Maybe you give them some notes or, you know, maybe you say, that's great, go and try it. And you probably notice that only a, you know, a small percentage of people actually follow up, you know, on it. And I have no problem when somebody follows up and it doesn't work. And they come back and they're like, it didn't work. Okay, well, what did we learn from What else can we do? Because a lot of stuff you try is not going to work. Of course.

A lot of stuff you and I've tried has a work. 95% of it hasn't. You know, that really happens with books, by the way. I actually stopped going out for lunches to help people with their books until they're written. Yeah, that's great. Because 90% of my lunches, they never wrote the book. Right, right. And so most of the advice was wasted.

Now if they have the book, I still try to find the time. No, those are all interesting. You know, when I was listening to you talk about that, I was thinking of an example in the wealthy barber. Yeah. One of the characters family member had a dog pass away, but had a beautiful fence yard and they were among a lot of apartment buildings. And so they ended up letting you book online the time for 20 minutes slots to run your dog in a backyard like a dog part, but without other dogs around. Oh, that's great. And it was all automated to get into the fence with the lock. And then

all of the payments went through the PayPal, et cetera. So using the modern technologies for a very old fashioned idea. I liked it so much when I heard it. I stole it and stuck it in the book. And she got to sit inside and watch dogs run around one at a time and didn't have to worry about, yeah, I mean, And there's lots of ideas like that. In fact, it's amazing how many of people tied into pets. In some way, shape, or form, they come up with some idea. Look at all the businesses that have started cleaning up pet messes in different cities, especially in Canada where we have the snow covering all winter.

And then people going in the spring and they tear care of all of that in your backyard. It ended up being quite a lucrative business for people. Yeah, it's also an industry in which people spend money. So you want to think about what are categories, industries, in which inherently you spend money. If you own a pet, then you love your business. pet, but naturally you're spending money on your dog or your cat. Golf is a great example, a lot of fitness, wellness, anything related to self-improvement. Like, you try to think about where do people spend money? Okay, that's a good idea. And I think also maybe another characteristic

is people are not necessarily trying to come up with the most original idea. Or maybe another way to say it is people feel pressure to come up with an original idea. And if you're coming up with something that has never been done before, then maybe you're a genius, right? Maybe you're a genius. And that that could be true, right? It's the iPhone. You know, it didn't exist until Steve Jobs envisioned it, right? Hey, the BlackBerry was out beforehand. Come on. We're from Waterloo. We're from Canada. Fair enough. I think it was, yeah, it was a transformation, but yes, in both those examples. But I'm like, my corner is people feel like they need to make the next Blackberry or the next iPhone. And this is a hang-up, and it prevents them from starting the business where people can come and run their dogs, you know,

in the yard through the automated service, you know, and the woman can sit and watch. Like, that's a great, that's a great idea. That's a helpful idea. Don't be innovative, be useful. It's another good, like way to think about it. Do you see a breakdown the people most likely to succeed, or at least to try this age-wise, or are women more likely than men or vice versa?

Have you seen any patterns like that in the demographics? Yeah, that's a great question. I've always thought in my audience more, like, based on psychographic, you know, than demographic. I hear from people of all ages and backgrounds and a lot of older people, a lot of people who are like into their second act or their third act, you know, and I think that's, that's wonderful. I'm trying to think if there's a commonality. Sometimes there's the sense of, I don't want to say like desperation, but a sense of like I need to make something work.

Like I've come to a point in my life in which I need to make a change. Maybe I'm feeling some pressure or maybe I lost my job or something and now I need to do something. So that can be, you know, one of these things that is hard and challenging but ultimately helpful for the person. and I've heard over and over like if I hadn't been pushed in this way, I wouldn't have made the leap or taken the jump. But I also think it's really admirable when someone is not facing that sort of desperation. And like their life is fine. And they're like everything's okay.

But they also think, well, my life is fine. But what do I want my life to be like? And maybe I even like my job and that's great. But I don't want to have to just depend on my job, you know, for the rest of my life. Like I want to go to work because I want to go to work, not because I have to. So what do I do? do what do I need to do, you know, to be able to create something. So I think that's, as I say, admirable just as much as somebody who's at this point of feeling pushed. You must be very

proud of the fact that you put the book out and a lot of people read it and I'm sure got back to you and said, hey, you got me excited. I tried this idea at his work. Thank you so much. I mean, it doesn't get a whole lot more rewarding than that. Well, you know that as well or, you know, better than I do, Dave, with your work, but I would also just say to what we were discussing a moment ago, I think it's a minority of people that follow up and take action, and I'm mostly excited about that. Like, I like to hear, like, people say, oh, it's a good book. And I'm like, okay, great. You know, I'm glad you thought it was a good book.

It's more exciting to hear from somebody that's like, oh, I read the book and it helped me, like, move forward with this way in my life. Or I had this idea that I didn't know what to do next and you helped me with the next step. I mean, that is the rewarding feedback. And what I always say to those people, I don't know what you say. But for me, I'm always like, well, I'm glad that the book is helpful. but lots of other people read the book and didn't do anything. So you did the work, you know? That's very true.

Good for you. Yeah, no, that's a great point by you for sure. Do you see any common mistakes being made? I mean, it's tough when all the businesses are so different. Beyond not starting, is there anything else? Do some people quit too early? They don't realize that it's always going to have its ups and downs and you've got to fight through some of the troughs? I'm a fan of quitting, not all the time, right?

But I think sometimes people let it go too long. It is tricky, right? Because. Yeah, we saw that on Dragon's Dan. Like I was on the equivalent and you're so right. I mean, some people you're thinking, you know what? No one like to quit or be a quitter here. Right.

It's okay. Wonders quit all the time. Like I have a whole chapter in front of my other books about that because I think it's a false mentality. You know, persistence is like the highest value. I don't think so, you know, I think smart people are willing to walk away from something that's not working. But it's also true that you have to give things like a reasonable chance. So, yeah, what are some common mistakes? I don't know.

Maybe it's just continuing to gather information. you know, obviously you want to educate yourself, you know, you and I are in the business of helping people educate themselves, so we are pro-education, but I think some of those authors that I have met, like, that I've had the lunches with, sometimes, you know, there's a certain group of them that they just come back year after year with, like, more information, but they haven't actually written the book or done the work. And, you know, I understand, I don't mean to judge them, because I think there's things I've been putting off in my life or avoiding that I probably should move forward with. But I think often it's just,

It's easier to just kind of remain in that place of like the pre-stage, like before I start the business, before I write the book. I want to think about it, but not actually do it. No, I think you're right on all of that. Hey, on a positive, no, we were talking about marketing. You know, in Canada, we've seen a lot of these micro businesses initially get traction, farmers markets. So they've taken, they've got the old-fashioned stall at the farmers market. They've seen the sell through. They've seen how much the consumer has enjoyed it.

And then they've started ramping up the distribution to other areas. In fact, one of the big dragons then investments. started that way and then ended up being ubiquitously available on both sides of the border. Yeah. So a lot of times you're just, do I have a product market fit? Are people going to like this? And to your point earlier, be willing to pay for it. Yep. You know, write that check, hit that credit card to get enough value back. And the farmer's market's not a bad testing ground for a lot of this. Absolutely. It's a very real world immediate testing ground, right? Because people are going to wander by and, you know, they're going to get their, the feedback will be in whether they buy it, right? I mean,

If you have everybody wandering by the booth and saying nice things about your product, it's kind of like great book. You know, that's nice, but that's ultimately not going to help you with your business. No, that's very true. And you know what else? You're talking about the immediacy. A lot of the people are coming back to the farmer's market week after week. And therefore, your already existing purchasers can give you feedback.

And you were talking about the importance of continuous learning. Nowhere can you learn more than from your users. Yep. Making sure you're having conversations with them. What do you like about it? What surprised you? How did you use it differently than the original? intentional intention, all these types of things. You can't buy into every opinion. But if you start hearing

certain comments over and over again, you know there's opportunities to grow there. Definitely. And that's a very loyal audience, I imagine, too, that's going to the farmer's market, you know, every week. And they are committed to supporting small businesses. So maybe that's another mistake is, is not listening to some of that feedback. And it's another one of those things where you have to have a balance because, you know, you need to have your own vision and you need to be able to say, like, we're doing this and not this and maybe some people say they want this, but this is not, you know, our core vision. But, you know, if you're, it's also true. If you're like, here's, here's the way I envision it and I'm never going to adjust, then that's probably not. You probably don't have it 100% right in the beginning.

And most successful businesses grow because they do adjust and learn along the way. No question. Before we wrap up in the $100 startup, I wanted to give you one more big compliment. I think that a lot of people read it and came away thinking, I can do this. Or it'll at least be very much fun to try. And that's one thing I love about a lot of these micro businesses. The people are enjoying it. I made the point aggressively in the wealthy barber redo that most of the people I come across who are doing this well, it's not a chore. It's not extra hours they're giving up. They actually really like doing it. In fact, for many of them, it's their favorite part of how they're spending their time. That's great. Well, life is short. I mean, you know, you might as well spend your life

doing things that you enjoy. And it's not to say that there's, I mean, there are things that we all have to do, you know, in life that maybe we don't enjoy 100% of the time, but isn't life about maximization, you know? And so I think, you know, as you believe, of course, you know, the right kind of work is a big part of that. And so if you fundamentally dislike your work, you know, whether it's at a job or what you're doing for yourself, I think something has to change because you're just going to be unhappy. So yeah, you have to find a way to enjoy what you do. And for me, working on my books, working in my projects and things. It's what I want to do.

You know, it's like the old question about like time, if time and money were unlimited, if you didn't have to work, what would you do tomorrow? And for me, it's like, I would do what I'm doing right now. You know, like I feel very fortunate. I didn't like the way you stared me right in the eye

when you said time is short. There was definitely an implication there that, Dave, your time in particular is widening down. It's not directed at you, but it is universal for all of us. I think mine is a lot shorter than yours. Okay, I want to move on a little bit to what you've been doing lately because I find it quite fascinating. And I want the audience to stick with us because it's an area I think needs exploring.

We're going to break it into two. One, the most recent book, Time Anxiety. Talk to us a little bit about the thrust of the book and then I'll go to area two. Time anxiety is about the fear of running out of time and what that entails, how it affects our life. I wrote it just out of my own personal struggle of feeling like, oh, I love what I do, as mentioned. but I also feel like there's not enough time to do it. And it's a world of unlimited choice and options. And it's great that so much information is available at our fingertips, you know,

and I love the Internet and community and such, but it can also be overwhelming. And so how do we decide what to do next? So as I started talking with people about this question of time anxiety, I would just use that phrase. They would say, what are you doing? I'm going to this thing about time anxiety. And almost universally, people would say, oh, I don't know what that is, but I have that. like I am anxious about time.

Like time affects my life and I feel it's running out and I don't know how to spend it. And so I wanted to do a lot of research, you know, similar to how I did $100 to research for a different topic, of course, but just trying to understand how this affects people's lives and, you know, what the root of it is and what we can do to feel better about it. So that's what I've been doing for the past two to three years. You made me a very important point now. There's just so much information, so many options out there. It feels overwhelming. If I just looked at half of it.

of the videos that people forward to me about economics and business and everything else, I'd have to close down my business and never see my family. Like it's just information coming at you and you do feel some guilt and some anxiety around what should I prioritize to? What do I get at, et cetera? No, it's, I think that's a wonderful topic and hopefully the book can be a big difference maker. Now, to wrap up though, I want to talk about your current event that you're running,

but why you're running it and how it ties into a subject near and dear to my heart, ADHD. Okay, great. Yeah. So the new event is called Neurodiversion. Neurodiversion.org. You can check it out. It's meant to be a celebration of all things, neurodivergence, including ADHD and autism and other types of neurodivergence as well.

We're doing this every spring in Austin, Texas. It's a global event. Like we're doing it in Austin, but we have people from all over the world, including lots of Canadians with us. And I started this event because there was nothing else like it. Like as I started learning more about my own ADHD, my own experience and realizing like, oh, this is how this has affected my life, like as a kid, but also throughout my adult life as well.

And in some ways, ADHD can be a strength. And I think it's good that we're looking at a strength-based, you know, approach for that. But it also comes with challenges and difficulties. You know, it's like everything. And so there's no event, in-person event that's bringing together people who are focused on the lived experience of ADHD and autism. And so there's academic events and, you know, research-focused, clinical events. But I really wanted to do something for the community. And so we started it last year, a little pilot project for about 300 people. This year we're growing a lot. We're going to have an expo. We do have a lot of clinicians and researchers with us, but our focus is on people who just want to learn more about themselves. Yeah, I think it's great.

You mentioned earlier you struggled in high school, despite the fact you're obviously very bright. And so many ADHD people struggle with school because you're sitting in that chair all day, trying to stay focused on often subject you're not that interested in. Did that play a role in why you hadn't excelled in high school? Totally. 100%. Well, I shouldn't say 100% because probably I had some behavioral stuff as well and I just was kind of rebellious. So I don't want to discount that. But yeah, a good bit of it. You know, it's like the classic ADHD personality. It's a very entrepreneurial, you know, personality. If you're motivated for something, then you will give 110% you know, to it. But if you're not motivated, then it's really hard to, you know, to give 25%. And so part of what you learn over time, you know, throughout your life is, okay, how can I construct my life around things I'm excited about and also what are some tools that I can learn. And, you know, and also what are some tools that I can learn. And, you know, for those things that I have to do. But, you know, you don't know that as a kid.

At least most kids don't. Right. And so that was, that was, I just thought there was something wrong with me, you know. And that's what that's kind of the message that that I received. And a lot of kids, you know, still probably receive that is like something's wrong with you. And it's really just like your brain is different. And you got to figure out how to do what you're good at and to not worry so much about the other things.

Yeah. It's interesting. I think society were really improving in terms of how we're dealing with this, how we're educating, et cetera. But the school problem hasn't gone away at all. We still have the same approach to school. You sit in a chair all day and are more or less forced to listen to five, six hours of teaching. And that is very difficult to do if you don't have ADHD.

But if you do, holy smokers. What about a lot of these new tools that have come out? There's software tools, reminder tools. Do you think some of them have had value? I do. I definitely do. And I think things are getting better in the school system in North America. But as you know, it's very fragmented.

And, you know, every district has its own kind of situation. So I think things are better. And the tools in such personalized AI. AI is obviously a big, huge topic, but clearly there are some benefits as well. And so I think things are getting better. But I think probably the biggest thing is awareness and just understanding, oh, okay, this is a pretty common situation. And also, as I said, it can be strengths based. If anybody's listening with a kid who's autistic or has ADHD or another type of neurodiversity, the more you can learn about this, the better off you're going to be as a parent and the better off your kid will be.

Interesting. You know, we tie the two subjects together. We go back to the $100 startup. You mentioned, how many ADHD people are outstanding entrepreneurs and how they're also very good at whatever one, two, three hobbies they tend to choose because they can get focused on something they like. They're very good candidates to follow the $100 startup path that you've laid out. Or the wealthy barber path, right? Yeah, exactly. Figuring out, what is that thing that I can do?

It's fair to say that they also struggle. And a lot of them experience difficulty because they haven't understood this pattern of hyperfocus. You can hyperfocus for a time and that's great. but you are going to burn out, you know, by doing that. So you need to understand like, okay, I need to allow for times of rest and such. But yes, absolutely. Well, listen, I'm really glad you're focusing on that field. You seem like a great guy.

I've really enjoyed your work over the years. Thank you, Dave. You definitely owe me a lunch. I have sold you a lot of books over the years. I've told so many people to pick that book up. Because, again, I find very motivating that book. And, you know, what about the, didn't you have a follow a hundred startups or something along that line? What did you, did I have a follow up with a hundred startups?

I don't know. Yeah. Didn't you have a follow-up book that actually gave even more examples? Oh, yes. So I did a follow-up book called Side Hustle, which I was surprised. No major publisher had used that title. This was about eight years ago, I think. And then because I had this podcast Side Hustle School where I was sharing all these different stories,

I did a follow-up book called 100 Side Hustles, a photographic book like showing like all these. I remembered it. You almost forgot it. I know, I did almost forget it. You're right. No, I thought that was good too, because the more examples people get, the more it helps their creativity and to kind of see the possibilities and customer. themize into their situation. Look, you're welcome to come back on any time. I'll give you the final

word. You've been to 195 countries. Would you not rank Canada number one? I would absolutely rank it number one. I love Canada. I went to every province, as mentioned, and continue to come back on all my tours. I've done stuff with Indigo and lots of other great bookstores. I have a wonderful community there. So we'd definitely come back. That's great. Well, listen, thanks so much for coming on, enjoyed it immensely. Cheers. Thank you, Dave.