37 min read

    37 min read

    This is a transcript of Episode 42: Chris Guillebeau On Using Uber To Be A Better Entrepreneur (Transcript) You can find show notes, comments and more by clicking here. You can also listen to the podcast in iTunes, Stitcher or wherever you get your podcasts.


    Announcer: Welcome to the Rideshare Guy Podcast, the site that’s dedicated to helping drivers earn more money by working smarter, not harder. So whether you drive for Lyft, Uber, Sidecar, or anything in between, we’ve got you covered. And now, here’s your host, Harry Campbell.

    Harry: What’s going on everybody? Harry here, and welcome to another episode of the Rideshare Guy Podcast. We’re all the way up to episode number 42, and today we’re talking with Chris Guillebeau on using Uber to be a better entrepreneur.


    So I’m pretty excited for today’s guest. I’m actually excited for every guest that we have, but I’m definitely excited to have Chris on because he has a pretty cool story. He isn’t a rideshare driver, but he was a normal guy with a blog and ended up turning into a New York Times bestselling author. Has a huge community of entrepreneurs, and now he’s a speaker and just really just an all-around good dude. I really enjoy talking to him and learning from him, and I think that you guys will too. He’s definitely someone that I look up to, but he’s also someone who I think you guys are gonna learn from, and that’s the main reason why I had him on the podcast today.

    Now, this isn’t a nitty-gritty kind of rideshare podcast that’s gonna go super in-depth about Uber or the rideshare industry, we’ll just touch on it here and there. So if this is your first time listening, not every episode is like this, but I still think that there’s gonna be a ton of value for pretty much anyone listening to this right now.

    By nature rideshare driving is just a very entrepreneurial endeavor, and there just are so many parallels between being a real business owner, being an entrepreneur and being a rideshare driver. And that’s why I wanted to bring on someone who’s literally an expert in that field of entrepreneurs.

    Chris has a huge community of entrepreneurs and budding entrepreneurs and has given tons of different career advice, and really just someone who has helped a lot of people. So you guys maybe familiar with his name if you’re kind of involved in the entrepreneur scene or community or anything like that, you’ll definitely be familiar. And I mean like I said, he is a New York Times bestselling author, so he’s a pretty legit dude, and also just a good all-around guy, so I’m glad to have him on and hopefully you guys will be able to learn a lot from him.

    So, you know, once you guys do have your business up and running though, obviously you’ve gotta take care of the housekeeping. And a product we mentioned before is Xero TaxTouch. It’s gonna make it pretty easy, right? That’s X-E-R-O. And I mean for me the one thing I really like about a lot of these new products is that they’re simple, right? They’re really easy to use. And I’ll leave a link in the show notes, to a cool new video they have that really explains their product well, but just to kind of give you an overview. What it’s gonna do is once you sign up and add your bank account, that’s really all that you need to do. If you have a credit card, you can add a different bank or something like that, you can also link that. But once you link up your one or two accounts, it will automatically import all your new transactions going forward, and it even auto-categorizes them, right?

    So if you guys are going out there and you’re spending money on car washes or meals and entertainment, Xero will categorize those for you, and then you can go through when you have some free time, when you’re in between rides, when you’re on the toilet, whenever you want, whenever you guys have some free time, and you can basically swipe left, swipe right depending on whether the transaction was personal or whether it was business. And it really just helps separate your personal and business life.

    And if you guys talk to CPAs or tax experts in the field out there, documentation is huge. And this is one of the first things they’ll say is you really wanna keep your personal and business, you know, accounts separate, right? You really wanna keep those transactions separate. And Xero makes this really easy because you don’t need to sign up for new accounts or anything like that, you can just do it all from right there within the app really. So it’s definitely a nice handy feature. And you can take a look at your profit and loss for the year, have a nice little report that you can send to your CPA, or use for your taxes yourself. So you guys can go check it out,, and that’s X-E-R-O.

    I also wanna give a little thanks to a couple of five star reviewers in iTunes. You guys know that five star reviews are a big help for me. Help me get guys like Chris Guillebeau on the podcast, lots of other important people. They see all those five star reviews and they say, “Hey, man, this guy Harry must have a good podcast.” So it’s definitely a help, and thank you to everyone who’s left a five star review, I really, really appreciate it. So recently we got a five star review from Dane Kirk, K-Matics [SP]. Hey, I think I know that guy. JayMcken02 [SP], Charming Kate, and Montage98PG [SP]. So thank you guys and girls. So thank you guys a lot for leaving those reviews. I know that it’s not, you know, the easiest thing to do. It’s not a ton of work, but if you haven’t done it, you can go to, and I’ll give you guys a future shout out in the next upcoming episode.

    So like I said, this episode and show notes can be found at I don’t know why I said that so weirdly. But just like any other episode, just hop over to the site and you can find it. Pull it up pretty easily. Make sure you stay tuned to the end too because I’m actually gonna share a cool story of how I actually came to meet Chris, and I even ended up giving him a ride home in my car. So he sort of got the full Uber and Rideshare Guy experience. But yeah, so hopefully you guys enjoy this interview and talk to you soon.

    Interview with Chris Guillebeau

    Hey, Chris, how are you doing today?

    Chris: I’m great, Harry. How are you?

    Harry: Doing well here in Southern California. Not quite sunny, but I think ready to start the day.

    Chris: Rock and roll. Sounds good, man.

    Harry: Awesome, cool. Well, thanks for coming on the podcast. And for those who don’t know you or may not have read some of your work, first of all, why don’t tell us how to pronounce your name so I don’t screw it up.

    Chris: Yeah, it’s Chris.

    Harry: Chris.

    Chris: It’s like C-H-R-I-S. No, the last name is Guillebeau.

    Harry: Guillebeau. Okay. So I know I’ve read it before on your site, and I wanted to ask you before I screwed it up. So thank you for that, Guillebeau. So why don’t you tell us a little bit about who you are and what you do briefly?

    Chris: Yeah. Sure. So, you know, I’ve been an entrepreneur my whole life. I’m 38 now, and I’ve kind of worked for myself since I was 17 basically, just because I wasn’t a good employee. You know, I was much, much, much better at doing something that I built myself. And so for the past 10 years in particular, I’ve had this community called The Art of Non-Conformity. I publish my work through books. I wrote a book called “The $100 Startup” which some people may be familiar with, and I wrote a book called “The Happiness of Pursuit.” It was about the quest I had to visit every country in the world. So that was an 11-year quest that kind of overlapped with some stuff.

    I was an aid worker for a few years in West Africa, and now I’m just fortunate I have this great community of people all over the world. And a lot of them are entrepreneurs, a lot of them are aspiring entrepreneurs, some of them are artists, some of them are students, travelers, nomads, just all kinds of creative unconventional people doing really fun stuff. So I kind of see it as my job to serve that community, and to serve that audience, and to help connect them and maybe give them tools and resources and show them, you know, how to improve in whatever it is that they’re trying to achieve.

    Harry: That’s a really good explanation of what you do. Have you practiced that before?

    Chris: No, it’s always different each time. I kind of say different things depending on the context. But yeah.

    Harry: That’s awesome. No, that actually sums it up really well. And I think one thing you said that stood out to me was that you weren’t a good employee. And I think that a lot of people in my audience and a lot of drivers out there in general, and people working in the on-demand economy, that’s kind of what they found. Maybe they weren’t necessarily a bad employee, but I think that a lot of the aspects of entrepreneurial life is what they value, right? Whether it’s the flexibility or being on your own, right?

    Chris: Yeah. I think I was kind of charitable when I said I wasn’t a good employee. Actually I was a pretty bad employee. And the thing is that I wasn’t lazy. Like this is the distinction. You know if I was motivated to do something, I would love to work, and I still love to work. Like if I believe in something, I’ll give 110%. But it’s just if I don’t believe in it, then I give 5%. So I had to find a way to craft a life around things that I cared about, things that I believed in.

    And probably like a lot of rideshare drivers, I craved independence, I craved freedom and choice. Like being able to decide for myself, and I placed a very high premium, you know, on that value. And I was like I wanna do anything I can to create that in my life and, you know, once I got it, then it was like it’s very hard to go back. You know once you have this freedom it’s really hard to say, “Okay, you know that was fun for a while but now I’m gonna go and work a day job.” No, it’s just you can’t do it.

    Harry: Yeah, that’s definitely one thing I’ve found with drivers is that they kind of start and they get going, and I like to call it the honeymoon period when they first start. The first two to three months are awesome. You’re driving people around, you’re having a lot of fun. You’re not even thinking about how much money you’re making, or taxes, or expenses or anything like that. And then you start to maybe have some challenges or some problems, but it’s often that a lot of those problems still are a lot less worse I guess you would say than kind of what you faced in your old job.

    Chris: Right. Right. For sure. I think there are different levels and stages of these things. And you know, like you said, you experience one thing and you’re like, “Okay. Like this is fantastic, this is the honeymoon period. What’s next? You know how can I parlay this experience into something else?” And that to me is what the greatest thing about Uber and Lyft is in terms of, you know, the entrepreneurial opportunity that it offers to people. I don’t know that, you know, it’s the best choice for someone to become an Uber driver and then do that for the next 20 years. Maybe it is for some people, but I do think it’s a fantastic like entry point into this whole world of being able to choose for yourself which, for years like people have seen some people on the inside of the system and they feel like they’re outside, they can’t get in. Well, here’s an easy way to get in. And once you’re in, then yeah what’s next? What are you gonna build? What are you gonna make for yourself?

    Harry: Yeah, and I’m kind of finding myself focusing in on a few of the keywords you’re saying right now because I really like the term entry point. You’re right, that if you’re gonna go out and be a full-time Uber driver and think about doing that for the rest of your life, there’s probably a few people who may wanna do that and who that may work for. But I think a majority of the people are looking at it more like an entry point, something to kind of get your toes wet.

    Chris: Right. Right. And it’s a good entry point. Of all the entry points you have in life, this is a pretty good one because the wages are pretty good. The average wage, I mean depending on your route and your city and all that stuff. But then also the tremendous flexibility it affords you. And I think, as I said, that that is worth a lot. You know that flexibility, it’s hard to put a dollar figure on that because you know, you maybe you could make even a higher hourly wage somewhere, but then if you have to be there from X to X time every day, then that’s just kind of, you know, it affects your whole life.

    Harry: Yeah, definitely. And I mean I guess kind of along the theme of your first book, “The $100 Startup,” there’s pretty low cost to getting started as a driver. I mean most people already have a vehicle, most people already have a smartphone, and it’s something that they can really basically get started with in the same day and apply and maybe be driving by the end of the week.

    Chris: Right. And you get incentivized to start, right? I mean like you get certain bonuses like when you’re starting out and all that.

    Harry: Oh, yeah, there are some pretty crazy bonuses and they definitely vary. We’ll talk after the show, maybe there’s a good bonus in your city. But yeah. So I definitely think you’re right on point. So what’s your experience with Uber been like so far, just kind of using it as a consumer and just talking to people about it in general?

    Experience with Uber as a Rider and Observer

    Chris: Yeah, I use Uber or Lyft every single day. I live in Portland, Oregon when I’m not traveling, and Portland I think together with Las Vegas, I mean you would know this better than me, but I think we were the last city in North America or at least in the States to get it. And I had used it all over the world in different places as I travel, and so I was kind of advocating for it to finally come to Portland. And so once they finally broke the  taxi mafia there, I was really happy that it showed up. So I’m a huge fan. I mean it has changed my life for the better as a consumer.

    I lived in Portland for two and a half years without a car and I just took public transport everywhere, and that was fine. I rode my bike. And then I’ve had a car for the past couple of years, but I don’t like to drive it. I actually prefer to just kind of go point to point, so I use car2go which is great, and then of course once Uber and Lyft came, and I used it as well. So I’ve had very, very few negative experiences compared to the hundreds of very positive experiences that I’ve had. I’m a huge fan.

    Harry: Cool. So when did you first realize that your audience had a lot of crossover with rideshare drivers? Uber and Lyft drivers?

    Chris: I think it was probably when I started meeting a lot of Uber and Lyft drivers and realized that a number of them were either familiar with my work already, or like we would just get to talking. And I’m not like a salesman, I don’t ever go like, “Oh, here’s what I do.” You know?

    Harry: Yeah.

    Chris: But it would just sometimes come up. They would say, “What do you do?” “I’m a writer.” You know, “What do you write?” “Well, I write books.” You know. I noticed that a lot of them would be really interested and would actively follow up with it. So it wasn’t just they were being conversational. Like I would get emails, you know, pretty much every 7 to 10 days or so from somebody who was like, “Oh, look, you know, I had this conversation with you the other day and now I read, ‘The $100 Startup,’ or the new book, ‘Born for This.'”

    So I thought that was interesting. You know not that they’re interested in me, but they’re interested in these concepts and how they wanna apply to their life. I used to take taxis all the time too. I mean I met some good taxi drivers of course, but I would say very rarely did a taxi driver ever follow up on you know, “How can I learn more about entrepreneurship? How can I improve my life in this way?” So it’s a very different market I think. You know drivers for Uber and Lyft.

    Harry: Yeah. And I mean I think that’s the thing that’s so unique is that really I mean let’s be honest. I mean it’s basically exactly like driving a taxi. You’re taking people from point A to point B, but it seems to attract these entrepreneurial types and the types that, you know, are interested in what you’re doing, and what you’re writing about, and what you’re working on. Do you think there’s a reason for that? Is it the style of work, the money, the flexibility, or what?

    Chris: I think it’s probably all those things. And I think like to be a taxi driver, like that is essentially a career of sorts, and, you know, there is this whole process you go through, and most of the taxi drivers at least in my city they would work 12-hour shifts. I mean they would start at 4 in the morning go till 4 in the afternoon, and certainly some Uber drivers do that too, but you know, that’s a pretty big commitment, you know, to go through, whereas obviously with Uber you can turn it on, turn it off. If you’ve got something you need to do, you go and do that and you come back. So I think it’s just a whole new world which obviously you know and most of your listeners know.

    Harry: Yeah. And I guess you would say no one really grew up thinking that they’d be an Uber driver when they’re older, right?

    Chris: Right. Exactly, because it’s such a new thing, but you know, it seems like it’s here to stay. At least as long as everybody can keep their act together and not get kicked out of cities or get mad at some city and decide not be there or whatever.

    Harry: Yeah, definitely. So we’ve talked a little bit about flexibility so far, and I kind of wanna focus on that for a second because that’s the one thing that I hear over and over from drivers that it’s the most flexible job in the world. Whenever they survey drivers, it’s always a numbered thing. And why do you think flexibility? I mean you’ve interviewed a lot of people about, you know, who are happy with their jobs. Maybe you can talk a little bit about that, and why do you think flexibility is so important to people?

    What Is It About Flexibility That Makes People Choose Entrepreneurship?

    Chris: You know flexibility isn’t important to everyone, but I would say it is a core value that more and more people are identifying with. And it’s not that I think, you know, 30 years ago people didn’t value flexibility, it’s that I don’t think they saw an alternative. And they didn’t realize like you know, “Oh, there are other ways of life.” And I would say even going back, like I’ve worked for myself for 20 years now as I said mostly online stuff, and 20 years ago when I was doing online work, I didn’t know a lot of other people who were doing it. And obviously some people were but it wasn’t common. It wasn’t like I could go into a coffee shop and there’d be like five people there like working on freelancing projects, or it’s like everybody had a side hustle on everything.

    So I think the more and more people have realized, “Oh, this is kind of…” It’s not quite mainstream yet, we don’t wanna exaggerate. You know it’s not quite mainstream, but like most of us, we know other people who have found a way to like create this life in which their work is kind of integrated but it’s also done you know according to their own terms, their own preferences. You know they are kind of managing that. So I think the more that we see like, “Oh, this is possible, then the more people desire flexibility.”

    And then as I said, you know, when we started, it’s like once you have it, it’s kind of hard to go back. And I think that was really a key point. So once you start your first entry point, whatever it is, if it’s driving for Uber or Lyft, great. You know great example, then you’re like, “I chose today to drive for three hours, I made X dollars. You know tomorrow I might work, you know, seven or eight hours or whatever.” It’s just so much fun. And it’s almost like playing entrepreneurially but then you also get paid for it. So what’s not to love?

    Harry: Definitely. I mean that’s one thing I kind of found when I first started driving was that man, I would almost do this for free just because of social interaction and networking. So when you’re looking at that entry point though, what do you think are the best ways to kind of build upon that entry point? Like what’s the next step once you’ve taken that first leap?

    Chris: Yeah, great, great, great question. So you’ve taken this leap, now you’re like driving around, you’re meeting people. You know I mean one approach might be to focus on that networking thing that you’ve talked about. Another approach might be to just kind of start observing a bit more. And start observing and asking yourself, “Okay, you know, what is out there that doesn’t exist? What problem is there that I can solve?” And don’t necessarily try to think about like, “I’m gonna start the next Uber, I’m gonna create the next iPhone.” Like that’s great if you have that vision, but I think, you know, most of us have a vision of solving some kind of problem for someone, being helpful in some way.

    You know something that I talked a lot about in “$100 Startup” is to pay attention to the questions that people asked you. And if people are asking you the same kind of questions over and over, it’s kind of like they’re identifying you as this expert and they realize like, “Oh, you know, Harry knows about this and like, you know, not only is he an expert but I actually have a demand for this information.” So I would say like keep asking yourself, “What is that thing? And what is the convergence between the different things that I’m good at, the different skills that I have,” which may or may not have anything to do with what you went to college for if you even went to college, and may or may not have anything to do with the traditional work experience you have. But the things that you’re good at or the things that you’re knowledgeable in, what is the overlap between all those things, and then what other people, you know, are also interested in what other people also care about.

    And I think this really is like the…it sounds like a secret. This is the next level of step to go from, you know, entry level entrepreneurship into the next thing where you’re actually kind of building something for yourself. Where you’re like, “I actually have ownership over this.” And for all of the amazing things about Uber and Lyft, which as I said, like you know 98% awesome, maybe the one downside is ultimately you’re still kind of trading time for money. And so maybe like the next step is, how can I build something that is more of an asset that will earn money for me whether I’m driving people around or not? And that’s the question I would encourage people to think about.

    Harry: Yeah. And that’s a really great way to look at it. And I also like that you kind of highlighted that it doesn’t necessarily have to be, you know, even something related to Uber and Lyft. Obviously with my own story, I kind of started driving and realized that it wasn’t quite as easy as getting people from point A to point B, so I started telling people how to do it better. But I guess there’s also the opportunities from kind of interacting with your customers or just solving those problems and those needs that people have.

    Chris: Absolutely. I mean this is how so many micro businesses start, and those people don’t go to business school, they don’t write an extensive business plan, they don’t go into debt. I mean that’s what “The $100 Startup” story has always been. And that to me is really exciting and interesting. It’s completely different from the Silicon Valley model of entrepreneurship as well.

    It’s not about like going to angel investors and like raising these rounds of capital and all that kind of stuff. It’s like, “Hey, what are good at? How can we find a way to parlay it in this knowledge economy where everybody is kind of buying, and selling, and trading all the time, and we can connect with people all over the world, you know, based on shared interests which is also very new, right? You know we used to be able to just trade with people like in our area or something, but now it’s like there’s this global community. So that is the interesting thing and also the thing that’s worth trying to figure out how to solve for your own life.

    Harry: Yeah. And I also like the term kind of solving a small problem, right? You can create a pretty killer business just by solving a pretty small problem. You don’t need to go out and start an Uber or a Lyft, you can go out and start a very small something that kind of solves a very specific problem, right?

    Chris: Solving small problems can make a lot of money. So it’s good.

    Harry: I think that’s a good way to put it, right?

    Chris: Definitely.

    Harry: Yeah. So you know I think we definitely talked about the fringe benefits and, you know, kind of everything that is good about driving for Uber. So I’m gonna put you on the spot right now. If you were an Uber driver today, what do you think you would do?

    Advice for Current Rideshare Drivers

    Chris: Okay. Wow. That’s great. Actually I have not thought about that. I would start with all the basics. I would try to be familiar with like my area which I wasn’t for the first two years I lived in Portland. I didn’t drive, so I didn’t know my way around at all. And you know now it’s interesting as I see like lots of Uber drivers coming into the market some are definitely better than others at knowing like the main streets. I don’t know if I have a big thing. To me I don’t care about somebody who offers me a bottle of water or gum or something. I don’t know. I wonder if there’s something different. I guess now that you asked me this since I wasn’t prepared, I’m wondering if there’s something…

    Harry: Well, that’s why, I’m gonna let you kind of talk it out.

    Chris: No it’s good. It’s good. I like it. I like it. I wonder if there’s some kind of…There’s gotta be something different that could be done. I don’t mean like a wild and crazy thing. Like I talked to somebody the other day who has like a karaoke Uber he does like in the middle of the night like with drunk people. That’s kind of fun I guess, but I don’t know, there’s gotta be something different.

    Harry: Something that makes you stand out, maybe.

    Chris: Yeah, a little bit. Just a tiny bit. That doesn’t push the edge too much, or doesn’t like, you know, frighten anyone or something, but I wonder if there’s some kind of like handout or something I could give that again wasn’t salesy, it wasn’t like, you know, because people are always wary of that stuff. But I do wonder about something like that, some kind of branded experience that people would actually, you know, either like or it just wouldn’t be for them but they won’t be kind of repelled by it. And I don’t know what it is but that’s the direction I would go in.

    Harry: Well, I think that’s definitely something and kind of in line with a lot of the work you’ve done, right? Making yourself stand out.

    Chris: Yeah, one way or another.

    Harry: Definitely. Cool. So you know, kind of wrapping up here, just one or two more questions. One thing that I wanted to ask you about is using Uber because you have a lot of entrepreneurs out there who are really just people pursuing their passions. And I’m kind of curious just to get your take on whether you think kind of using Uber and Lyft or just working in on-demand economy in general is good as sort of a crutch, right? You know some people kind of go with the theory that, “Hey, when your back is against the wall and you have to make something succeed, you devote 100% of your time to it. That’s great. You go and start a business, and if it fails it fails,” or do you think that strategy kind of approach where you have sort of a backup plan. You have Uber and Lyft to cover your basic expenses and then you kind of go out and work this job. What do you think is better? Do you think there’s a right answer?

    Chris: Yeah. I actually do think there’s a right answer. I’m a big fan of the second thing. I’m a big fan of the backup plan. And the thing about the backup plan is like you don’t have to tell people what your backup plan is, you can still commit yourself fully to something else. But then it’s actually great to have that peace of mind and say, “Okay, I am committed to this. I am gonna do everything I can to make this succeed. But you know, I have this crunch.” I think there’s a lot of value in that. So I think we tend to celebrate people at least in these like inspirational stories you kind of like go all in, and like they’ve almost failed, and like, you know, their whole life is falling apart, but then at the last minute they succeed.

    I mean it’s like a great movie, but then I think the reality is that backup plans are actually very safe and very comforting. And maybe backup plans actually allow us to take more risks. So backup plans can actually get us closer to that really big thing, you know, than like having to worry every day about, you know, providing for our basic needs or something. So I think that’s yet another benefit of this entire economy.

    Harry: Cool. So my last question for you is what’s the biggest takeaway? I mean you’ve interviewed a lot of…I kind of like to think of you as like a happiness expert. You’ve interviewed a lot of…and what I mean by that is like you’ve interviewed a lot of people who are really happy with their jobs and really content with their jobs and like figured things out. So what’s the biggest takeaway for someone looking to get to that level kind of with the work that they’re doing.

    Chris: Yeah. I would say, you know, from the latest book I wrote, “Born for This,” which, you know, features Harry Campbell, the Rideshare Guy. You know I saw…

    Harry: Page 262.

    Chris: That’s great. That’s great. I saw that most people who are successful and happy, in the way that they decide for themselves, they don’t actually know from a young age like, “This is what I’m going to be.” And they actually do a lot of different stuff, and they tend to experiment. They tend to change their major in college, they tend to work different jobs, they tend to, start something on the side, and then eventually they do kind of find this focus.

    But I think the mistake that we make in our society is we look at these people who have found that focus and we don’t see everything that came before that. We think like they had been working toward that all this time, and maybe they were but not in a linear, you know, fashion.

    They’ve actually been jumping around and doing stuff, and that was not a negative at all, that was actually a positive and that everything that they did informed their thinking and their process going forward. So I’m a big fan of experimenting, I’m a big fan of going down different paths. If you go down a path and it doesn’t work for you, that’s also okay, you can just turn around and go back. And people who are willing to adjust, and to tweak, and to adapt I think are much more successful than those who say, “I’m just gonna stick with this no matter what. Even if it’s not working out, I’m gonna keep doing it.” I don’t think that’s a good idea.

    Harry: Definitely. Well said. So awesome. Well, Chris, thanks for coming on. And before I let you go, we talked about a couple of your books, so where can we learn more about you, more about your work?

    Chris: Yeah, awesome. Well, thank you. The new book is If you go there, you can learn about it, and all my work is Chris Guillebeau on social or So that’s G-U-I-L-L-E-B-E-A-U. If you type something close to that in Google, it’ll probably bring you to me.

    Harry: Awesome. Sounds good. And we’ll link up to all that in the show notes and everything that we mentioned during the show too. So, Chris, thanks again for coming on. It was a pleasure.

    Chris: Awesome. Huge honor. Thank you.


    Harry: All right. Thanks again to Chris for coming on the show, and hopefully I didn’t butcher his last name too bad. I think I’ve said it differently about five times now, but I’ve never been that great with challenging last names. So my apologies to Chris, if I didn’t say it right.

    I really enjoyed that interview. And I mean I think I really liked a lot of the advice that Chris gave because I think it’s very practical. I mean, you often hear about these big and crazy extravagant stories of people solving big problems and then you know kind of that go big or go home mentality. But I don’t think there’s anything wrong with starting small.

    And you’d be pretty amazed at how we talked about solving a small problem can turn into a pretty sustainable and pretty successful business that’s gonna keep you really energized and you’ll be really passionate about and lead to a more fulfilling life.

    I definitely think it’s a good idea starting with that mindset, right? Doing one or two things, right? Starting small. Let’s say you have another job and then you’ve gotta hustle and make something happen on the side, right? Build up from something small. You know there’s no reason that you kind of have to go all in and make this work or nothing is ever gonna work. So I think that, you know, that strategy that Chris talked about is something that I’m a big fan of, something that I’ve used.

    And I mean really it’s pretty rare, right? We see a lot of things publicized about people kind of hitting these home runs. But I mean most people don’t do this on their first try around, right? I mean even with my own story. This isn’t the first website that I’ve started, I had three or four that you’ve probably never heard of before I started The Rideshare Guy. And it takes some skill, it takes some luck, but at the same time if you keep putting yourself in a position to succeed, I think that’s when you’ll have the most success.

    So you know, like we talked about on the podcast with Chris, I think there are a small number of people driving for Uber as a career. I mean I think that according to my latest survey and some of Uber’s own numbers actually confirm this that about 20% of people, 20% of my audience is doing 40 to 50 hours a week driving for Uber or more. And I mean I think that’s great, right? If you can make it work, go for it. But I think most people, right, 50% of drivers or more in some cities are actually doing 10 hours a week or less. So that means they have other things going on. They have side projects, maybe they’re entrepreneurs, maybe they work day jobs. I don’t really think that it matters.

    I know there are a lot of entrepreneurs in the audience and just in general, because that’s the type of person that being a driver attracts. But I think that you don’t have to be an entrepreneur, right? You can still learn a lot from this job and apply it to other industries. I think you can be just as happy being an entrepreneur or being a fulltime…you know working a full-time day job for someone else but you still have to kind of employ a lot of these principles and think about things in a lot of the same way.

    So I think that you can honestly actually even learn more from people in other industries. So that’s why I’m a big fan of bringing guys like Chris on the podcast because although he’s not a rideshare driver, he still has this really unique mentality and this cool mindset that we can now as drivers go and apply. And now when you’re out there driving, whether you’re trying to network or whether you’re trying to find investors for your business, or whether you’re just trying to find a job, I think that you can apply a lot of this stuff.

    Now, I mentioned at the beginning of the podcast that I’ll tell you guys a quick, little story about how I actually came to meet Chris. And it was pretty funny because one of the other podcasts that I’m a big fan of called The Art of Charm Podcast, which is a really cool show that kind of touches on lots of different business and entrepreneurial, and just life and relationship topics in general which I think you guys can definitely check out.

    I was a big fan of that show, I’d been tweeting back and forth with the host every time I listened to an episode that I liked. And one day he tweeted me out of the blue and said, “Hey, I just read about you in Chris Guillebeau’s new book, ‘Born for This.'” And I said, “Really? That’s cool.” I didn’t know who Chris was. I had maybe heard of his name once or twice, but you know I wasn’t an active follower.

    And I ended up reaching out to Chris and I said, “Hey, apparently I’m in your book, you wanna send me a copy?” And it hadn’t been released yet, so it was kind of a pre-release. And he ended up mailing me a copy. And sure enough, there on page, I don’t know, 262 or something like that, there I was and kind of just a short little blurb about my story.

    And it was funny because he actually caught me when I was just getting started with The Rideshare Guy and I was actually offering coaching services to drivers. So I had this blog, and one of the ways I was trying to monetize it was basically through providing one-on-one coaching with drivers as far as strategy and getting things set up. And obviously I’ve progressed a long way since then and we don’t really do that anymore.

    But it was funny that Chris kind of found me at that point and I ended up emailing him, and he had an event in Orange County, and I actually went to his event and ended up giving a quick little two to three-minute sort of testimonial about my story. So that was kind of a cool experience for me. I got to meet him in person, I got to talk to him a little bit, and then I actually gave him a ride home to his hotel because he was on his book tour. So that was pretty cool. And I think there in the car I pitched him on coming on the podcast, and he kind of had to say yes since I just gave him a ride home. So that’s kind of a funny story, and I just wanted to share that with you guys real quickly. We’ll leave a link to his book in the show notes. It’s definitely something I think you should check out.

    And remember that this episode is sponsored by Xero, that’s spelled X-E-R-O. It’s a cool Cloud accounting software, and their new app, Xero TaxTouch is a freelancer’s best friend. So basically no matter where you are, you can actually capture and categorize all your business expenses with a single swipe just left or right, and you can gather everything you need for your Schedule C. So come tax time, you’ll be prepared and your CPA won’t charge you extra, or if you do it yourself, you’ll have a nice and easy route. And basically you can turn your iPhone into a tax prep machine without any of the surprises. So make sure you save yourself some time, and you’ll also thank yourself come tax season if you go ahead and download a 90-day free trial of Xero in the App Store. You can head to, that’s X-E-R-O.

    And make sure that you check out the show notes. That’s You can also subscribe to the email list, you’ll get notified of new articles and podcasts. And of course if you have any questions, don’t hesitate to reach out on Twitter @TheRideShareGuy or just shoot me an email and just say hi, I’d love to hear from you, [email protected] All right, take care and stay safe.

    This is a transcript of Episode 42: Chris Guillebeau On Using Uber To Be A Better Entrepreneur (Transcript) You can find show notes, comments and more by clicking here. You can also listen to the podcast in iTunes, Stitcher or wherever you get your podcasts.


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    Harry Campbell

    Harry Campbell

    I'm Harry, the owner and founder of The Rideshare Guy Blog and Podcast. I used to be a full-time engineer but now I'm a rideshare blogger! I write about my experience driving for Uber, Lyft, and other services and my goal is to help drivers earn more money by working smarter, not harder.

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