Side Hustle: From Idea to Income in 27 Days

As a result of having done this so long, I get to see guests multiple times and see how their businesses have evolved. Today, I’ve got a three-time interviewee. His name is Chris Guillebeau.

When I first had Chris on we talked about his blogging business The Art of Non-Conformity. I was in awe of how his mission was both open to different ideas and also very clear. He knew his audience. They were travelers. They were people who were trying to get out of the 9:00 to 5:00.

Now, his business has changed. For some reason, he’s not focused on the guides, which did really well. He’s now got something called Side Hustle School. I want to find out about that and his new book coming out, “Side Hustle: From Idea to Income in 27 Days.”

Chris Guillebeau

Chris Guillebeau

Side Hustle

Chris Guillebeau is the founder of Side Hustle School, everything you need to create a new source of income without quitting your day job.


Full Interview Transcript

Andrew: Hey, everyone. My name is Andrew Warner. I’m the founder of Mixergy, where I interview entrepreneurs about how they built their businesses. I’ve been doing this now for years. We’re coming up on 10 years soon, Chris.

Chris: Amazing.

Andrew: As a result of having done this so long, I get to see guests multiple times and see how their businesses have evolved, see what they’re up to. Today, I’ve got a three-time interviewee here on Mixergy. His name is Chris Guillebeau, a name I’m proud to not just know how to pronounce but how to spell because I’ve written your name so many times over the years.

Chris: That’s awesome. I can spell your name and pronounce it as well, just for the record.

Andrew: Because I changed it to an American name that anyone could spell. If I gave you my real last name Khalili, which is what I was born under, you’d have trouble spelling it.

Chris: I should have done that too.

Andrew: Kjaliki I used to get, Khalali — Khalili. So I changed it to Andrew Warner, much, much easier to spell. Have you considered switching your name to Warner.

Chris: I feel like it’s too late. When I first met Seth Godin like six years ago — I don’t know if I told you this story — I asked him for advice. I was like, “Seth, what can I do better?” He’s like, “Change your name.” I’m like, “Too late. I’m already doing stuff.”

Andrew: You are kind of stuck with that name. But thankfully, there aren’t a lot of people’s names who are Chris G-U-I and then anything after that. So if anyone just types that into Google, it shows up. All right. Plus, I also believe that spelling is going to be outdated in about five, ten years. We’re all going to be speaking to our devices. Our devices will be able to adjust and type. That’s not what we’re here to talk about, though that is very cool technology.

When I first had Chris on here. We talked about his business, which was blogging, which was on a blog called The Art of Non-Conformity. I was in awe of how well his design was, how much his mission was both open to a lot of different ideas, but also very clear. He knew his audience. They were travelers. They were people who were trying to get out of the 9:00 to 5:00, but not in like this dorky get out of the 9:00 to 5:00, more like creatively express themselves and they were drawn to Chris because he wanted to visit every country on the planet, which did you? You got to see them all?

Chris: I did indeed, yeah.

Andrew: Yeah. North Korea?

Chris: Yeah, everywhere.

Andrew: Impressive.

Chris: 35th birthday, I finished three years ago.

Andrew: And I was also in awe of this business that he had, which was, where he sold these — what I liked about it was it didn’t feel like he was just slamming people with expensive products. It had really creative angles on there, titles on there, designs. The guide to building a business was called Empire Building Kit. I just dug that.

Over the years, we’ve talked about his different books. Now, his business has changed. For some reason, he’s not focused on the guides, which I was in awe of, which did really well, which is why I interviewed him. He’s now got something called Side Hustle School, which I want to find out about and he’s got a new book coming out. This guy keeps publishing books, “Side Hustle: From Idea to Income in 27 Days.” This is not the cover you guys are going to get. I happen to get a lot of these — what are they called?

Chris: Galleys.

Andrew: Galleys?

Chris: Yeah, special editions. They’ll be worth at least a quarter on eBay one day.

Andrew: If they survive. What I’ve noticed is, as you can see, I beat up books a lot. I don’t understand when people are delicate with their books like they’re going to save it for their grandkids. You read it. You’ve got to get into it. You can see I mark it up. I fold the pages.

Chris: Authors really like that. I go to book signings and people come up with books like that and they’re apologetic. They’re like, “I’m so sorry.” I’m like, “No, you read my book. That’s the best thing you can do for an author.”

Andrew: Right. I used to be the kind of person who would want to save it just in case I — I’m an entrepreneur who always thinks I’m going to run out of money — so I thought, “If I run out of money, at least I have a clean book I can sell.” This is like the woman who had to sell her wedding ring or engagement ring to survive. Then I realize, “No, it’s much better to get the knowledge in my head.”

So “Side Hustle” is the book. Side Hustle School is the business. Chris, good to have you here.

Chris: Thank you having me.

Andrew: I should say my two sponsors are the company that will help you send out smart email. It’s called ActiveCampaign, and the company that will help you sell more when you’re doing one on one sales, it’s called Pipedrive. I’ll tell everyone about those later. Chris, your whole thing started as a side hustle. eBay was the thing?

Chris: My whole life was a side hustle. My whole life is a series of side hustles. I always said I realized at a certain point I was unemployable, so I’ve got to do something. Unlike a lot of your guests, I never single-mindedly focused on one thing and built it to huge eight or nine-figure revenue or whatever. But I just kind of, from age 19, I’m 39 now, 20 years of just kind of figuring things out, doing things I was interested in.

Andrew: Why side hustles all the time? Why not say, “You know what? I’m going all in. I’m going to have one idea, live or die by this thing, but I’m going to focus on it 100% the way you focused to getting to every country in the world.”

Chris: Yeah. Fair enough. You essentially say that the quest to go to every country in the world was an 11-year focus, but I had to pay for that, so that’s where the side hustles came in. This year, I am almost 100% focused on Side Hustle School, “Side Hustle” book, this concept, this message.

But I guess for me, I’ve always been interested in a few different things. I didn’t want to just kind of pigeonhole myself. I wanted to be able to shift and do things I enjoyed and things I found meaningful. So that was where the side hustle way came to be before that term existed, before it was common for people to start lifestyle businesses. For me, that’s what worked.

Andrew: I see how it works for you. Every one of these little projects has its own special sense to it, like World Domination Summit, your event. I’ve talked a lot about how beautiful it is, how every detail is taken care of. But that’s you. For most people, isn’t a side hustle something that you do on the side, you don’t care enough about it to actually let it grow, and you hope it becomes something? But without investing all that you have in it, will it really be something? If my wife was a side wife, will we really be as engaged as we are with each other? Will we be able to deal with the lows?

Chris: Great question. I wouldn’t suggest that your wife becomes a side wife. I would say that for a lot of people a side hustle, it’s not that they don’t care about it, they don’t believe in it. It’s just something that compliments the rest of their life. Maybe they actually do enjoy their day job or their main business or whatever they’re focused on, but a side hustle is additional security.

It gives you a different kind of confidence. It’s a different kind of creativity, perhaps. I talk to a lot of people who do one thing for their day job or their business because they are focused so much on that, but then they like to go home and do something a little bit different or build some other asset on the side. I don’t think it’s that they don’t care about it, I just think it’s a different way of thinking.

Andrew: I think if you’re talking about a side hustle as something you do on the side as a hobby, I kind of get it. Have your hobby and maybe it develops into something. That’s one approach that you talk about in your book, “Side Hustle.” The other approach seems to be try it on the side and maybe it becomes really big, which is what happened with you, Chris, right?

Chris: Sure. I try to feature stories of different people on the show and the book who do create six-figure or beyond side hustles. Sometimes that’s their intent and sometimes it just, as you said, develops. You don’t necessarily know what’s going to happen, but the idea is you’re not taking on a lot of risk, you’re not going into debt. You’re not walking away from a secure job or whatever your secure position is to do something that’s unproven.

Andrew: Your businesses, which is the one that became the biggest? Let’s talk revenue, not biggest impact.

Chris: Yeah, sure. Actually, writing books is probably more than 50% of my income, like writing and publishing books.

Andrew: Really? You make money from selling these books?

Chris: I know. It’s crazy.

Andrew: How much money can there be in these books?

Chris: Multiple six-figure a year. It’s not millions of dollars.

Andrew: We’re talking a couple hundred at least a year.

Chris: Yeah.

Andrew: Because you have your following, who, like me, just loves your writing. You can put out Andrew Warner sucks-type book, I’ll read it because I like your style. I like your style because it’s quick and you have a lot of freaking examples. It won’t just be, “Here’s what I don’t like Andrew,” and you pontificating for 300 pages. It will be, “Here’s 700 people who don’t like Andrew and I’ll tell you their stories.”

Chris: That’s funny. I try to be helpful. I think that’s a good point. I don’t think if I could put out anything and then people would buy it. It would be nice if you would, but I don’t think most people would. I think it’s been successful because I am trying to feature, as you point out, this barrage of case studies, and I’m trying to show stories of people all over the world in different backgrounds who have done these things in different ways, because if you just write from your own example, people think, “I can’t relate to that guy,” or if you tell one person’s story, they think, “Good for her, but she had some advantage. I’m not her.”

So with the “Side Hustle” book, I’m trying to feature like dozens of stories of people who have done this, very specifically. $100 Startup, which we talked about before, really specific about all these accidental entrepreneurs, about how they built their business, how much money they made, where their mistakes were, etc. That’s why it’s successful, I think.

Andrew: I think that should be a lesson for every author. I don’t need you to pontificate for 300 pages. Some people can pull it off, most people cannot. I’d much rather you show me some examples because the examples not only add credibility, but they teach me. They let me learn about the world outside of my own world.

I thought when I first met you, you had a great model. You were blogging on The Art of Non-Conformity. Then you had this business where you were selling these guides. It was actually producing a lot of money. You weren’t selling them for a lot of money. I think it was $50.

Chris: Yeah. It was like $50 to $100.

Andrew: Maybe I could go to $250.

Chris: That would be the highest.

Andrew: What happened to that business? Why aren’t you focused on that?

Chris: I think I’m not focused on it because I don’t think other people are focused on it. I don’t mean just my business. I feel that model has shifted for a lot of people and maybe some folks are still being successful with it, but I do think starting a few years ago there was a great saturation in that space. Because it was a great business, more and more people got into it. Then the way that people engage with content began to change a lot as well.

Podcasting has been around a lot, of course, but in the past few years there’s been this renaissance with it. So I feel like in a situation like this, for me specifically, I could continue to do the same thing I’ve done. I can beat my head against the wall and I might be able to be a little bit successful at it just because I have a track record and I can evolve, but I think it would just be this slow and steady decline.

Andrew: What you were seeing was what? The business was online education, where you sell —the guides, would you call them guides or courses or a combination of both?

Chris: I call them guides. Online education, I think, also changed a lot too with platforms like CreativeLive, like Udemy, Skillshare, etc. People are just learning in different ways. So if you want to teach and share knowledge online, which you do and probably lots of your viewers and listeners, I think you have to be receptive to how things are changing and always be thinking about the future and not just about the past.

Andrew: So, before, it was possible for someone who was a blogger, who had something to teach on his own site. How did things change? What do you see today?

Chris: Yeah. I think it’s still possible, but I think it’s definitely different and it’s shifted. So, for me, one thing I thought was last year, last summer, I’m like, “I need to wake up and enter 2005 and I should start a podcast.” So, for me, I wanted to do that. That’s why I focused on that this year.

Andrew: Forgive me, I want to get a little more specific. When you say it’s not working because the thing shifted, are you saying people aren’t buying as much anymore?

Chris: Yeah.

Andrew: That’s what you’re seeing.

Chris: I think not buying as much. It’s not ultimately buying. That’s ultimately what it’s about as revenue, but also just lack of interest and lack of, “I’m not impressed. What’s different about this? Why should I care about this when I can get this information elsewhere, perhaps?” That kind of thing.

Andrew: You were starting to see it in your numbers. At your height, where were you? Then where were you when you started to notice a dip?

Chris: It was also like a multiple six-figures business?

Andrew: Can you be more specific? It’s been a few years, so maybe we’re not going to be revealing anything private. At its height, how much revenue did it produce?

Chris: I’m happy to share all the numbers. I think at its height it was like a half-million-dollar business, which was great. It was mostly just me. I didn’t have employees and I had to pay royalties and different things, but that’s what it was at. It was definitely kind of a steady curve. I don’t even remember, last year might have been $100,000 or something. Obviously that’s quite a decline. Part of it is I wasn’t developing new products. To be fair, I wasn’t actively investing in it much myself. But I guess the reason I was not actively investing in it was I sensed that things were changing and I needed to do something different.

Andrew: I see. You see, there’s the difference between you and me. I will — I need to learn to stop. I’ll just beat my head against the wall. I will keep going. I will keep going. I’ve said this forever. I hated school. I had no value, little value out of going to college. But I started out on this educational path, I wasn’t going to stop until I finished it.

I have to get to the finish line. I’m using this bike training app called Zwift. There’s like a special challenge where if you can ride for how long, basically, it’s like a year worth of riding, I’ll get the glowing bike. I’m not going to stop until I get to that, even if I discover that cycling is not that great for me, I have to do it.

Chris: You’re incentivized. In that case, you have a goal line. In that case, you have this destination. I felt the same way with going to every country in the world. Sometimes I was tired of it. Sometimes there was a place I didn’t want to go necessarily, but same kind of thing. I’m motivated because I see a finish line.

With a business like that, it doesn’t have necessarily like this predetermined here’s where you reach 26.2 miles, therefore, you complete the race. I think maybe if I was still motivated to it, I would do it, but I was also shifting my own motivation as well. I had done it for a while, it was fun. But for me, I’m only successful when I’m doing things I’m really excited about. Like if I’m excited about something, I will give 110% to it, if I’m not, then it’s kind of hard.

Andrew: And that’s the other difference too. You’re thinking about this as part creative, part entrepreneur. You could have said, “You know what? I see this being the next CreativeLive for this type of product. I have to get to that level, $1 billion is my number,” or, “Whatever is twice is much as what I have today will always be my next goal,” but that’s not who you are. You want to get excited about the next creative project.

Chris: Yeah. Creativity is a big motivation for me. I love what I do. I work all the time because I enjoy it. I have to set my own goals and my own matrix for it.

Andrew: Yeah. That’s essentially your audience too, I noticed. You talk about in the book “Side Hustle” that people need to describe who their ideal customer is, take them to virtual coffee, I think you say. That means sit down and imagine you’re having coffee with your ideal customer. Who’s your ideal? How do you describe them? I have a hard time describing to other people who it is.

Chris: Yeah. You know, for years, I’ve always focused much more on psychographics than on demographics.

Andrew: That’s fair.

Chris: I don’t care about how old they are. My audience is pretty evenly divided, men and women, which makes me happy. It’s much more like “Art of Nonconformity,” go back to that, the psychographic was like people who are pro-change, people who want something different out of life, people who like to travel, as you said, who want to start businesses, who want to be an artist or something that’s a little bit outside the norm.

Maybe they don’t necessarily live in places like San Francisco or Portland. They live in places where they might feel a little isolated. My goal is to find those people and connect those people. That was my ideal customer for that. With Side Hustle School — I don’t mean to interrupt you.

Andrew: Go ahead.

Chris: I’m much more focused on people who have day jobs and don’t necessarily want to become an “entrepreneur,” but they feel like they’re on the outside looking in with this entrepreneurial movement and they feel like a lot of the resources that have been developed for them are actually not really good for them because they’re encouraging them to quit their jobs and all that.

I’m really focused on people who have day jobs, love the idea of having a different source of income, don’t know how to do it, don’t have a ton of time. So I’m trying to create a process for them. So that’s who I’m focused on now.

Andrew: I don’t relate to those people at all. I don’t understand that.

Chris: Not everyone is like you and me.

Andrew: I get it. Totally fine. Intellectually, I don’t get why you wouldn’t do everything and also kind of pretend you have to go to the bathroom on a date with your wife and go check your phone. How do you not do that? How do you not go that deep into it?

Chris: For years, I had a similar perspective. Then like I’ve traveled the world. I did meetups in all 50 states, every country in the world, etc. I meet a lot of really interesting people. I realized there are a lot of interesting, fascinating people who are fulfilled, living a meaningful life, but they don’t necessarily think the way you and I do. In the last book, I featured a firefighter, like the woman who was the first female firefighter in Mississauga, Ontario many years ago. That was her mission.

So, if you want to be a firefighter, obviously you can’t be a freelance firefighter. You have to be part of an organization. You have to go through a process. She’s still changing the world. She’s living the dream. But she also wants a different source of income, etc. My mom worked for NASA, same kind of thing. You can’t be an entrepreneurial aerospace engineer. Maybe you can if you’re Elon Musk or something, but most people are part of a company or an organization.

Andrew: I thought you had an example in your book. You have so many that I don’t even know how to find it, of a guy who was a NASA engineer who — I know what it is. I’m about to interview someone who was a NASA engineer who said, “Why can I solve this space suit issue for them? They’re using my space suits, but I can’t sleep in a warm bed because the blanket is not warm enough or something.” So apparently she could have if she would have gotten this book.

Chris: I’ll let her know that. She’s just about ready to retire, but she’s got one year left, so I’ll let her know what to do with her final year.

Andrew: Bedding, her riches will be made in bedding. What about this? I don’t even have to hunt deep in your book — page number one of the galleys here, there’s a story about a British guy who works in a construction company who created a website with a series of fish tank reviews, included links to Amazon products. A few weeks later, a check arrived in the mail for $350. His partner couldn’t believe this was real money until he took her out to dinner with the proceeds.

Are we promising people the idea that do what you love, money will come in, you don’t have to pay attention. You explicitly say, “He forgot that he even linked to Amazon,” and then a check for $350 came in and then $700 a month every month after that. Are we promising them too much if they’re not fully focused? Can they really deliver this?

Chris: Sure. Well, it is a true story, first of all. Every story in the book is true. I would never promise that it’s guaranteed. I would never promise that it’s easy. I try really hard to not use that word “easy.” I can say simple. I can say anyone can do it. Anyone can start this kind of project. You’ve got to work for it. You have to be fully focused? How focused do you have to be to write a series of fish tank reviews and put it up on a WordPress site and link to Amazon?

The greatest thing about that, he’s not making like a huge amount of money, but years have gone by, he’s done nothing else for that website. It’s still bringing in $700 a month for him. I think that’s pretty amazing. It’s allowed him to go on an additional vacation with his wife.

Andrew: Is that feasible for a lot of people? Will people be able to read this book and say, “I actually don’t care about fish tanks, but I really do care about Apple Watch bands. I’m going to create a site for that,” and then expect they’re going to end up with $350 coming in and $700 every month?”

Chris: I never tell people to follow their passion. I tell them follow your skill and find a convergence between your passion and what other people are excited about as well. So nothing is guaranteed, like no book or no resource is like if I watch this interview, I’m going to make $1 billion. But I do believe it’s a replicable process.

On the show every day, I do this seven-day a week podcast now, every single day I’m telling a story of somebody who’s done that in different ways. It’s kind of like what you do. I get into their failures as well and their mistakes and what was hard and what didn’t work, but usually in the end, I tried a bunch of stuff and some things didn’t work and some things did. So I do think if people kind of stick with it, they will find something like that.

Andrew: And you do believe it’s a repeatable process. You actually explicitly say to people you can adjust this process a little bit, but don’t adjust it so much that you get away from what I’m telling you. Use this. It will work. So I’m going to come back in a moment and ask you about this process and we’ll start out with where ideas come from. But first, I’ve got to tell people about ActiveCampaign. Do you know about ActiveCampaign?

Chris: Just a little bit. I’d actually like to know more.

Andrew: The thing about ActiveCampaign was I thought I knew about them. They’ve been around for years. They used to send out these plain emails. You could just send out a broadcast email using ActiveCampaign, but from what I understood about them, they didn’t have any marketing intelligence.

When I say marketing intelligence, I mean when somebody buys, your email to them should not be, “Hey, we’re now offering a 10% discount to anyone who buys,” your email should be smart enough to send out messages to everybody, but you should be able to exclude people based on what they did or start sending them messages based on something they did.

So, if someone’s clicking over and over and over and still not buying, you might want to reach out to them and say, “We’re going to give you a 20% discount,” and of course, once they buy, you stop pestering them about buying but you tag them as having bought and you start sending them emails to encourage them to use what they bought. That’s basic marketing automation.

If you want to get even more clever than that, ActiveCampaign will let you do that, like put tags on your site so that when people are touching specific parts of your site, you understand it and then you can send them email based on what they’ve seen. Imagine if somebody comes over to your site and over and over and over again, they’re clicking on like Uber, we’ll get into how you talk about Uber — so if they’re clicking on Uber as an entry point, you might want to send them an email saying, “Here’s a way to start with Uber as a side hustle but actually move on to starting your own business. I want to tell you about the entrepreneur who did exactly that and now he’s got a thriving business.”

You want to notice what they’re clicking on in their emails. You want to notice when they’re buying. You want to notice what they’re doing on your site. You want to do all of that so that you could then send out email that targets what people have done, that changes based on what they’ve done.

So that’s the idea behind ActiveCampaign. If you’re out there and you’re using one of these — there’s one specific software that keeps — screw it. Why am I going to be traditional and not tell you the competitor’s name? It’s MailChimp. MailChimp is a nice company. They offer no marketing automation. People sign up for them right from the start because it’s free, but you don’t want to send out the same email to everyone. It’s nice they advertise on NPR. It’s nice that they’re a good company and successful.

But if you’re really serious about your marketing, you can’t use a company like them. You can’t use a company like AWeber. You have to find something that lets you talk intelligently to your audience based on what they’re done, based on what they’ve told you about them. There are lots of different programs that do this. Most of them are way too complicated and so you don’t use them or you use them but you can’t pass it on to an assistant because your assistant can’t figure out how you used it and you’re stuck.

ActiveCampaign gives you all that marketing automation. They make it really easy for you to use. I’ve noticed something they’ve added that they didn’t have the first time that I was advertising them—free trial. So, I’m going to give you a special URL where you can go and try it for free. After you sign up, they’ll even give you your second one for free. They’re going to do two free one on ones with consultants who are going to help you actually use marketing automation intelligently and if you happen to be with one of their competitors, they will migrate you over.

Here’s the URL, will give you all that, will give you all that. If you have any problems with ActiveCampaign, if you think that what I’ve said—if what I’ve said doesn’t end up becoming your experience with them, I want to know about it. Come to my office here, 201 Mission Street, 12th floor, let me know in person or email me, I will never talk about a sponsor that doesn’t live up to what I promise. So go check them out and let me know if it doesn’t work out, ActiveCampaign/Mixergy.

I got kind of worked up in the middle of that ad.

Chris: You believe in it. It’s good.

Andrew: I do. It’s kind of awkward that I invited you into the ad, but I didn’t address you after the first question.

Chris: It was good.

Andrew: I was like a fire breather on that one.

Chris: I didn’t want to interrupt that. It’s good. I totally agree about MailChimp. I think MailChimp is great for the pizza parlor on the street that’s going to have 300 people on their email list or whatever. I think that’s who they’re designed to serve. But as you said, if you’re serious about your business, you’re probably going to need another solution.

Andrew: For some people in even my audience it’s going to be okay. But frankly, when you’re really ready to do some strong marketing, intelligent marketing, you’ve got to do it.

All right. The first step is figuring out an idea. This is one of the hardest things in the world to figure out an idea, right?

Chris: You think it is?

Andrew: I do. I think that if you’re on the right path as Andy Rachleff, the venture capitalist with Benchmark said, even if you screw up management, the business will thrive. PayPal did not believe in email as a way of sending money back and forth. They did it as a side thing, and then it kept taking off and enveloping their bigger business, which was sending money using those old palm pilots. So how do you find that right idea that will take off?

Chris: I’ve been surprised about this too. What I see is there are two problems. People are trying to figure out their side hustle or probably any business venture. It’s like don’t have an idea, not sure what makes a viable idea and then number two, it’s like I have plenty of ideas, I’m not sure how to make them happen.

When I started this project in January, I thought most people were going to be in that second group, maybe it’s because my own bias. I’m like I have lots of ideas. I just can’t do all the stuff that I want to do. But I started doing these workshops around the country and probably seven out of ten people were like, “I need an idea.” What I’m shifting the focus on is teaching the power of observation, which is essentially about learning to spot valuable ideas.

So it’s partly internal, partly external. The internal part is like let’s take an inventory of myself. It’s not just like, “What am I passionate about? What are my hobbies?” What are my skills? What are all of my skills? Not just the skill that I got in college or what I did for my day job, but like what do people ask me about? What am I a so-called authority on? What’s that weird little thing I like to do?

I’m really into fish. I know a lot about fish tanks. A lot of people need to buy a fish tank. What do they do? They go to Google and like fish tank review. This is the first thing they type in for that if you’re going to buy a fish tank or wrist band or whatever you said. Going down that path is the first thing internal. Then external is just spotting problems in the marketplace or something that bothers you or could be done better or more efficiently.

Here’s the story from the book of a woman who actually works in marketing. She started this personalized candy heart business, like the Valentine’s Day things that say, “Be mine,” or whatever. She wanted to make them for companies as a client gift and couldn’t find a good solution.

Basically, she ended up starting her own thing and that actually became more than a $100,000 a year side hustle. It’s seasonal. She just does it mostly around Valentine’s Day. She still likes her job, so she does that. That’s an example of like, “I saw something that wasn’t working well. I found a way to do it myself.”

Andrew: Yeah. You have a whole chapter here about how to find ideas and you say I want you to get ready to — this is not your words. I’m paraphrasing. You want us to be aware of what are people doing and what do they need? So if we start to see as we’re driving down the street a line of people waiting to get to a coffee shop, we want to know what are they trying to do really? What are they really trying to accomplish, not just the facts of trying to get coffee, but are they trying to accomplish? What do they need?

You give an example of a guy named Steven, who happened to be a web developer. He noticed a clear need, which at the time was that people in San Francisco did not know how long they were going to spend in traffic. There wasn’t traffic information built into Google Maps. So he leveraged it to serve an active market, which is San Francisco commuters. I guess he created a website for them to see how traffic was doing every day?

Chris: He created an app, like in the first year of the iPhone when the App Store launched, basically, he created an app for that called Routesy, which maybe you or some other SF folks are familiar with. It actually ended up doing really well. So he saw he’s a commuter. He’s struggling with getting data or information about how to make his commute easy, a ton of commuters in the Bay Area, of course, and traffic is a major issue. So since he’s a developer, he has that skill. He learns how to make an app.
By his own admission, the first app was really crappy. It looked terrible. It had all these errors, etc. but he put it out anyway. It ended up doing really well. I think the first month, he made like $2,000 and he was like, “Oh my god, didn’t expect that at all.” The advertising was like an afterthought, like at the last minute, he’s like, “I should sign up for a little campaign that puts banners on my app or something.” After that, he started paying much more attention to it, and now I forget what it’s doing. I think it’s something like $7,000 a month or more.

Andrew: In the book, you left it off with $7,500 a month. I imagine that’s got to have gone down.

Chris: He made more. Great.

Andrew: Sorry?

Chris: Go ahead, it’s good.

Andrew: No, what?

Chris: I was like $7,000, $7,500, something like that. He’s doing well.

Andrew: Yeah. I just wanted to show you that I read the book, that I remember the small details.

Chris: That’s amazing.

Andrew: I really like that I read my guest’s books before they come on. What I notice though is it helps me ask better questions and guide the guests to talk about what my audience is curious about most, but it also makes me into a bit of a know-it-all and I find myself either saying the story on behalf of my guest or interrupting them with small little details that aren’t that important. You said $7,000, I say $7,500. I have to show you in the audience that I read the book. I have to get value out of the fact that I spent time reading it.

Chris: Andrew, it’s probably better than the alternative, because sometimes there’s like a big delay between when I write the book and when I’m like out promoting it and stuff. So I do these radio interviews, especially when the book first comes out, it’s not as fresh in my mind as it should be. They’re like, “On page 276, what did you mean?” “I don’t even remember what I said.” So this is better than that.

Andrew: I’ll even take that over people that say, “What’s this book about?” You know they didn’t read it and they come out with this idea that my audience didn’t read it either.

Chris: Yeah.

Andrew: You do talk about —

Chris: That’s why Mixergy is legit.

Andrew: That is why it’s legit. It’s also why it might kill me here. I needed so much time. I just needed an extra five minutes after the interview started, but I felt guilty for having pushed myself to get this done on time and then needing another five minutes. I demand a lot of myself. I have to be aware that what I’m demanding of myself is always going to be beyond what I can achieve, and I can’t be upset with myself for not being there.

Chris: That’s a good lesson. I need to absorb that myself because I struggle with that too, and I beat myself up and that whole thing.

Andrew: You don’t seem to. You seem like the most sane person I know.

Chris: I do.

Andrew: How does it manifest itself in you?

Chris: Self-doubt, negative talk, just frustrated with myself, comparison to others, which is a terrible thing.

Andrew: Who do you compare yourself to negatively that’s almost embarrassing for you to admit here?

Chris: I don’t know anybody that’s embarrassing to admit. Gretchen Rubin is a good friend of mine. My podcast is on her network. She does a fantastic job. She’s sold like a ton of books, but she’s on all the social media all herself for the most part. She doesn’t have a team. She’s got like one person who works for her. She’s also got a family. I don’t quite know how she does everything that she does. People probably say that about you, they say that about me. But then you and I, we also probably know people who are like, “I do a lot, but I feel like she or he or whoever does so much more.” So that’s one person. She’s great.

Andrew: The worst are when people achieve a lot and they’re so mellow because it’s all easy for them.

Chris: Hate that.

Andrew: I recently read a book, “Letterman: The Last Giant of Late Night,” that showed me how I need to be aware of where I’m beating myself up too much for not hitting my vision of myself. It talks about why so many comedians reverse Letterman. He really was a risk taker as a performer. He would go on daytime talk, which he got fired from, which is why he’s not known for that, and he’d bring a television set out and show you his competitors to see what was on that was better.

He had such rapport with his writers. He was actually dating really seriously his head writer, but such rapport with them that they would physically lock him out of his stage when the show was starting. So the announcer would call David Letterman and he was stuck and you can see him being pissed at himself and at the world and that was funny. He threw things down a building to watch them explode on the ground, really daring, interesting person.

Chris: I’m going to go read this book.

Andrew: It made me go back and watch old YouTube videos of him to see why he was such a good performer. But to me, I don’t remember him as a great performer. I remember him as the guy who came in second to Jay Leno. What I realized was when he went to CBS after he didn’t get “The Tonight Show.” He was competing against Jay Leno and he was actually winning.

But he was constantly competing internally with who he thought he should be, constantly saying, “I’m not where I want to be,” and it used to be internal and then at some point, it came out. It started to be out more on his show. He started to feel more what he calls self-loathing, but to me, it’s more comparing himself to his vision and where he wanted to be in the world. You get it, that worked for him. Most people wanted to be on Johnny Carson — I’m going to go off for a little bit on this book, sorry.

Chris: It’s good.

Andrew: I’m passionate about it. Most people wanted to be on Johnny Carson. They would spend years just trying to get a set on Johnny Carson. He got it pretty soon after he came to Los Angeles, but not only that, he got to be the guy who took over for Carson when Carson wasn’t around. So this pushing himself to be something bigger than most people would ever dream they could be helped him. But then it started to work against him. He started to feel like why didn’t I get “The Tonight Show,” what’s wrong with me and the way that I pursued the business part of show business? He started to say things like, “I screwed up the Oscars.”

This became a big turning point for him. The author of the book, Jason Zinoman, said the Oscars actually when he hosted the Oscars, he had the second biggest ratings of the night. He looked back to see the reviews of the Oscars and the reviews of his performance were all great the next day, they were solid.

But night after night, Letterman beat himself for not doing a good job with the Oscars. I guess he had a vision of something else it could have been. He just kept letting this bleed into his show, and the audience bought into it and the popular understanding of his performance on the Oscars was that he bombed because he set that in motion and he did that over and over until he couldn’t stand himself anymore.

So the reason I bring that up is I have big visions of where I want to be. I can’t allow where I am today in comparison to that to be a drag, to be like the thing that I talk about, which I have in my past interviews.

Chris: Interesting. Yeah.

Andrew: It’s a turning point for me to have read that book.

Chris: The whole time you were telling that story, you kind of went back and forth between whether it was positive or negative. He was like so driven and he did this and this was really good and so committed to his cause because of that and that helped him to be good. Then it kind of shifts. Is it that it’s healthy for a time and you can’t let it — it’s healthy when it’s internal but it shouldn’t be external?

Andrew: I think it’s healthy when you use it in a healthy way, but it can really be something that you get carried away with. I thought the fact that I kept pushing myself to do a better job in my interviews in the early days of Mixergy meant that I could read a book within an hour so that I could prepare to do a good job with the guest and be okay with the fact that maybe we don’t get to 99% of what’s in the book, but that’s fine.

Where I think it became a problem was I started to say I want to be this big thing. I’m only a podcaster. Podcasting is too small compared to where I want to go, and I didn’t seize it for the opportunity it was. So I didn’t recognize it. I remember even having guys like Tim Ferriss on going Tim Ferriss sees the fact that I’m interviewing him, this is a little thing for him. He’s doing bigger things than this.

Podcasting is so small in comparison, and I let that become a distraction. Meanwhile, Tim saw this and loved what he was doing. Soon after he started podcasting, he came and asked me about what I was doing and how I was doing as a podcaster. The fact that he even got into podcasting is an example of how warped my vision was. So I can’t allow that to happen. I can’t allow myself to do to myself what Letterman did to himself later in his career.

As a result of it, not only did he lose to Jay Leno, but he had a kind of miserable life later on, constantly full of anxiety and self-loathing. I wonder if he was even on medication. I don’t remember whether he was or not. So it doesn’t sound like that’s an issue for you.

Chris: No. This sounds like it’s very much an issue for me, Andrew. So if it doesn’t —

Andrew: So how do you deal with it?

Chris: If it doesn’t sound like it’s an issue, then I either haven’t been honest with you, which I don’t think is the case. I think I’ve been pretty open and transparent, or maybe we just haven’t talked about it.

Andrew: Let’s talk about it now.

Chris: Which part?

Andrew: What do you do when you deal with it? When you see Gretchen Rubin, she’s got incredible fame, do you just brush it off?

Chris: Yeah. I don’t know if she’s the best example because, like I said, I love her and she’s been very good to me. I don’t know if there’s a single person that I look to that is like that. It’s more just like what I feel about my own potential, which sounds kind of inflated, but what I feel like — it’s just like the last book didn’t hit the way that I would have liked it to. So then it’s like I’m concerned about my stature or status in the industry. That’s such a bullshit thing to care about, but I do.

So there’s this ego thing and anxiety. Then I also get emails from people like, “I read this thing and it changed my life.” I gloss over it, but then I have some kind of negative experience, even if it’s just my own perception, kind of like the Oscars thing, I just hosted WDS, World Domination Summit recently and for the most part, I thought it was pretty good. The team did a fantastic job. I felt like it was really solid. There may be like two points in the facilitation that I did that I walked away and did not get across the thing I wanted to get across.

That’s of course what I go away with. We had this amazing experience, thousands of people in town in the biggest theater putting on all these parties. Then I think, “I forgot to say that thing that was important for me to say.” Probably nobody else cares, but I do. I do think it’s good to challenge yourself. Use this as fuel for fire or something, but not beat yourself up. I don’t know the difference between the positive side, like it’s good when you use it in a healthy way, but how do I know when it’s healthy and when it’s not? I think that’s my problem.

Andrew: I think for me, it’s what do I do with it and what’s the self-talk that comes as a result of it. If it’s something like I’m not doing enough as a podcaster — first of all, I need to make sure is that true? Often, those things are lies I tell myself. The other is what do I want to do with that? Do I want to obsess on it, or is there something I can do as a result of that? Is there something I can do, figuring out the better questions to ask? What do I want?

Unfortunately, I don’t have enough time to sit and think about it. I don’t think we do a good job of thinking about stuff on our own in isolation. If you and I were talking about, I can actually realize what this negative talk is, question it together with you and deal with it.

I recently signed up for an app that’s like a therapy app just so I can say, “Here’s my process. I do really well when I do it on my own, but I don’t do it on my own enough. I do really well when I do it with my wife, but we have two kids now, we don’t have enough time. Will you work through this with me and let’s go through this process?” This app stinks. Talk space — they’re so bad. All they have to do is match me, just connect you with someone. It’s too bad.

Chris: Somebody needs to make that app, make a better version of the app.

Andrew: I do think so. I think that as a company, I get the sense that they don’t care that much. If you go to their Glassdoor ratings, you can see that they don’t care about their therapists. I always thought, “Well, then their therapists will still care about the people.” But when they don’t care about their therapists, they don’t set their therapists up for success with people. But I do think that model of online coaching, online therapy, that kind of thing actually makes a lot of sense.

Back to your book, “Side Hustle,” so you come up with a bunch of different ideas, which is another issue, frankly, Chris. People do have a lot of ideas and especially if you alert them to have to come up with new ideas, they’re going to have way too many. Then you have this grid right here where you help them figure out which idea to pursue. Can you describe like what are we doing with this grid? How do you want people to come up with the right idea when they have too many?

Chris: Yeah. This is a very simple process. It’s meant to be intuitive. You can do it in five minutes. I call it the Side Hustle Selector, something like that. You can do this for other ideas in life as well. Like I’ve got five ideas. Okay. Write down my five ideas. I know I can’t do all five right now, and then I’m going to come up with a set of criteria. I forget exactly what criteria I used in that particular matrix, but you probably have it all memorized. It’s like five different things there — profit potential, feasibility, something like that.

Andrew: Feasibility, persuasion, profit potential, efficiency and motivation. You want us to think in all five in those categories are we — high, medium or low? So is it high feasibility, medium feasibility, or maybe it’s something I really can’t do? Profit potential, is there enough profit potential, medium profit potential and so on?

What’s interesting to me about your approach is you’re not coming up with a solid number for each of these ideas. You’re not even coming up with something I could compare idea to idea. You’re just saying be aware of these five categories. Once you are and you could see where your idea stands within each of those five categories, then you can pick an answer and understand you’re not committing to this for life.

Chris: I feel like some trends will emerge as you do this. I think that’s the important thing. So, yes, if you want to assign a number. You can make it more complicated if you want to, but we’re just looking for something simple. I think when you have five ideas, one good thing you can do is eliminate two of them. This might help you do that really quickly. It might help you see there’s a front runner or get down to the final two and then you make your choice.

That’s why I use motivation as a factor. I know a lot of business analysis wouldn’t do this, but I think it’s important in a side hustle or even really in your real business, but that’s a different conversation. You should love what you do. You should be passionate about it. You should look forward to going home from work to working on this project. So if your motivation is low, maybe that’s not the right thing at this time.

Ideally, you want more highs and mediums for all the categories, but we’re each in different seasons in life. So sometimes you have to make more money, so that profit potential is more important. Sometimes you’re trying to just start your first project because you’ve never done this before. So feasibility is super important. You have to be able to see a path from where you are now to where you are 27 days later with this project started.

Andrew: All right.

Chris: It’s a way to help you make decisions.

Andrew: Let’s talk about launching. How do we find the right people to launch to, and how do you want us to sell it?

Chris: There’s all kinds of different ways to do that. I guess for me, I’ve kind of gotten away from an extensive pre-launch model like building like all this hype. For me personally, I’ve done it before. I just feel like speaking of saturation, speaking of fatigue, I feel like people are little bit tired of that kind of stuff, generally speaking. If you do it like amazingly, sure. If you do it in some different way, that’s great.

Otherwise, I’m much more focused on how can I make something that’s really great? How can I find that group of people, even if it’s a relatively small group of people at first that kind of prove my model and then from there, let’s grow by referral, let’s grow by word of mouth, etc.?

Andrew: Sell like a Girl Scout. What does it mean to sell like a Girl Scout?

Chris: There’s a story about this little girl who was eight years old and set the record for selling the most Girl Scout cookies ever. I think it was $80,000 or something. She basically said my secret was I went to people’s doors and I asked them if they would buy $10,000 worth of Girl Scouts and everybody said no. So then I said, “Buy five boxes.” Everybody said yes, basically. Obviously, that’s like an old school sales strategy, but it’s funny when you hear about it from a Girl Scout cookie selling perspective. So my encouragement to people is be creative. Don’t be afraid to be creative and don’t be afraid to ask for the sale.

Andrew: Yeah. You give examples of other people who are also doing things for nonprofits and for good causes, but instead of asking for the sale, they’re a little bit pushy and they’re trying to impose their desire on you.

Chris: Yeah. Like walking down the street in Portland or other cities, these people that stand on the corner and they’re very aggressive about trying to get you to talk them. I hate that. I feel like it’s manipulative even if some of the causes they represent are good causes. I feel like that strategy is manipulative.

Andrew: Yeah. I didn’t realize until recently that most of those people are just paid employees of some company that represents a nonprofit. I had some who worked here on my floor. They would do these rallies. They would talk about how to persuade people, how to stand in front of them. I didn’t realize that that was a thing.

Chris: Yeah. It’s guilt marketing. I guess they justify it because the end justifies the means or whatever, but I don’t know. There’s got to better way.

Andrew: I think it’s one thing when you’re getting paid to do that, but when it’s your own product, I think not being clear about what you’re selling and asking for the offer is a way of being embarrassed by the product and not actually getting the feedback, not telling people what you want and so you don’t get what you want and you don’t get the feedback and it doesn’t do well.

Let me do a second sponsorship message for a company called Pipedrive. Do you know Pipedrive?

Chris: Actually, I don’t. I’m looking forward to hearing about it.

Andrew: I freaking love Pipedrive. Here’s the problem that most people have. You want to sell one on one to people. So what you do is you fire up a CRM, you start adding contacts into there and you start sending out email. You can’t keep track of where people are in your sales process. Who did I email yesterday? Do I follow up with them? Then after the follow up, what happens? Worse than that, we start playing mind games on ourselves. We say, “Nobody loves me. Nobody wants to buy from me,” because I emailed everyone and no one responded.

What Pipedrive does is says I’m going to give you a set of columns, one column for each step of your sales process, so you do have to articulate what it is and you can keep editing it and changing it and improving it as you learn, but come up with something. Whenever you send out an offer to somebody, put a card that represents their name in the left most column. What that gives you is a visual representation of how many people you contacted and they also give you stats so you know not nobody loves me, but you only sent out three offers yesterday.

You only sent out five in the last month and you think that you sent out a lot because it took a lot of willpower to do it or it took you a lot of time to write the email, but you’re actually very unproductive, you need to do more. It gives you stats. Then once you get your numbers up, like actually send out ten offers a week, then the next step in your process is very clearly laid out. You look at a screen that shows you all step. Each step has its own column. You realize, “I have a whole lot in the left most column. Nobody in the next column over. Let’s start moving.

So what do I do after that? The next column over is send a follow up email. Let’s start sending follow up emails to everyone. I only get the right to move a card from the left most column to the next column to the right of that after I take that action sending the follow up and so on. So you get to see exactly where everyone is. You get to see how well you’re doing.

We had a problem where we could not book enough guest and organize them in Mixergy. We fired up Pipedrive. Boom. Now I know exactly where everything is. I know how many people we’re sending out offers to. I know where we’re screwing up. Well, it turns out for a long time we weren’t sending out follow-ups.

So that’s the idea. Then once you start hiring people to help you, they get to see your board and they get to help you out too. So if I don’t send out a follow-up to Chris about would you come do an interview with me, Andrea would see it and she can follow up because she knows what the next step is.

All right. If you guys are out there and making sales, this is for one-on-one sales via email, via Facebook Messenger, via text, via phone, wherever it is. If you’re doing one-on-one sales, you need a system to keep you organized and Pipedrive is that system. I urge you to not just go to largely because I will not get credit for it, and I like getting credit for it because I’m competitive. I want to be their best source. I have been their best source even though they also are now advertising on NPR, I’m their best source of new customers as far as podcasts go.

But if you go to the special URL, you’re going to get 14 days free, 25% off of the next three months after your 14 days’ free trial and frankly, you’ll get tagged as a Mixergy listener and I know the company over there very well. I’ve interviewed the founder. I’ve gotten to know him and other people at the company, when you come in as a Mixergy person, they know that you are someone that they better take care of, largely because it will hurt my friendship with them if they don’t take care of my people. So here’s the URL. Go check out That’s

I have a few other questions here to get into in the book. As you can see, I’ve circled stuff, like 10 people to ask to help and so on. Is there something you think is important that I should not leave out before I start getting carried away with my next set of question?

Chris: I like your questions. Go for it.

Andrew: What about pricing? So now, I know what I want to sell. I know that I’m going to be really clear with it. How do you charge, especially when you’re charging for services?

Chris: Yeah. This answer might be different from what some of your other guests might say. Again, I’m focusing on this side hustle model. People get really overwhelmed with this. They really have no idea because they don’t know how to do a pricing analysis and all that kind of stuff. I would say first thing’s first, when you’re doing this for the first time, let’s figure out what your baseline income should be. Think about how much you make for your day job, kind of break it down like here’s my hourly wage or whatever.

For your side hustle, it should be no less than that, I would suggest. It ideally should be more, but you want to make x-dollars an hour or whatever. Kind of figure out here’s the service, how can I then price the service minimum, like it could be higher, but minimum is like whatever I need to see to succeed and call myself a success with this side hustle. That’s what I encourage people to do.

Andrew: Yeah. I think what you’re referring to is how many guests will say price based on how much money you’re saving or making your customer if it’s a service or if it’s a product, price on what competing products are selling for.

Chris: Sure.

Andrew: You can go cheaper or way higher, cheaper so you compete on price, higher so you can compete on prestige. But you don’t say that. You’re saying you guys are starting out. This is a side hustle. Think about your needs. What’s the bare minimum that’s going to make this useful for you and then build on that.

Chris: I do think value-based pricing is a good approach. I always encourage people to think about what are people getting out of it. I think that’s good. When people are just starting out, like how do I do this, that is kind of a hang-up. I’ve seen people that had everything developed except the price. They just feel paralyzed by it. That’s why I’m just like start with this. Then if it goes well, then that’s great. You raise your price.

Andrew: You mentioned Lyft and Uber a lot. This idea of side hustle is a really great name. It’s a great name for a book, great name for a movement because it’s a thing now, right? Everyone wants a side hustle either because they’re admiring entrepreneurs and they want to get into this entrepreneurship thing just like when we were kids, maybe we saw people who were rock stars and we wanted to play music and be rock stars too.

It’s entrepreneurs that are now those new rock stars, and so people want a side hustle for that or because their job isn’t paying enough money for them to live and so they need a side hustle. That’s why companies like Uber are now capitalizing on it. I think Uber or Lyft has an ad that says, “This is your side hustle.”

Chris: Yeah.

Andrew: I was surprised when you kept referring to Lyft and Fiverr. Why do you want people to do that? I kept wondering. Then I saw the difference between a starter idea and the next level idea. This was a big part, I believe, of your approach. What is the starter idea and what is the next level idea?

Chris: I actually am kind of critical of the ride sharing movement or the gig economy as being a side hustle. I think those are glorified part-time jobs.

Andrew: Not even glorified. It may be glorified on the way in, but they’re worse than part-time jobs in many ways.

Chris: You have the option to set your own schedule. That is a major benefit. That’s about it. Everything else, it’s not different from anything. I talk with a lot of Uber and Lyft drivers. I do think those folks tend to be more creative and more entrepreneurial than the average taxi driver. Think they are thinking about their future, trying to invest in themselves, but that’s good. But I see that as a starter idea.

I make this distinction between yes, you can go on If you’ve never done this before in your life, you can go on, sell some kind of service and people are going to pay you for it tomorrow or next week. They might not pay you very much money, but they’re going to pay you for it. Actually, when you’ve never made any kind of money for yourself before, that actually feels really cool. It feels great. It actually feels fun. I’m doing something for fun like I would do online except I happen to get paid for it. So, great. But that’s not really what I want to take people to. I want people to get introduced to that if that’s helpful.

But then my whole model with the side hustle is to help people create assets. So if you’re driving for Uber, you’re not really creating an asset. If you’re helping other people drive for Uber, like this guy we talked about briefly. There’s a guy who built a business called the Rideshare Guy and he’s consulting and coaching other rideshare drivers. He’s built a membership site. That’s a whole business. That’s an asset. That’s a growing industry. That’s a distinction I make there.

Andrew: That’s a really important one to make. I didn’t pick up on that in the book, but you’re right. I picked up on the fact that you want people to start with something simple and if has to be an Uber thing on the side, that’s fine. If it has to be a Fiverr gig, that’s fine, but that’s the thing that gets you thinking about side money, that opens up your eyes. Don’t look at it as the way you’re going to pay the bills on an ongoing basis.

Chris: Exactly.

Andrew: You know what I want to talk about that I don’t think people are going to appreciate it but that’s why I’m here? They can flip through the book to get the things they think are important. I’ve got to give them something I think is important for them and they won’t recognize — the origin story. The origin story is so important. How many entrepreneurs do I interview here who when we pre-interview them about where the idea came from, they give me like an a, b, c thing, “Well, first I just sat and made a list of things and then I came up with an idea and now I started.” What’s the problem with that, with just giving you the facts?

Chris: It’s just the facts. It’s not that it’s a problem. It’s just very descriptive. It’s very basic. It’s generic. You can be basic. You can be generic, but isn’t it so much more powerful to have a story like it wasn’t just that I discovered this thing, it’s I had this problem and my life was negatively impacted for this thing and I kept looking for solutions and I was disappointed. I found this app and I was like, “This app is going to be my solution,” but then this app actually kind of sucks.

Then I found some website, but no, I was disappointed. I thought maybe I can make it. Then I’m not just making it for myself, but I realize there’s all kinds of other people out there that also struggle with this. This is much more of a community story. I found my first customer and it really did change their life and I was like, “I’m going to make this my mission for the next decade or however long,” I feel like that’s so much more impactful and powerful.

Andrew: Yeah. You give this example in the book about a couple that goes to Nepal and as they’re in Nepal, they get cold, decide to get warm clothes. It turns out the warm clothes are much cheaper than what you get at home and more interesting than what you get at home. They start to wonder can we bring this back to — I think they were from Canada. So they bring back this stuff to Canada. Now it’s an interesting story. It’s got Nepal connected to it. We understand why they’re doing this as opposed to them just saying we wanted to make some extra money on the side, which is also true.

Chris: Exactly.

Andrew: So we found this cheap stuff to sell Canada.

Chris: It’s fine to say that, but isn’t it so much better to be like, “We actually met the mountain shepherds in Nepal making this stuff and a percentage of the profits actually go to girls education in Nepal. We are excited about this as a company but also as a mission. Isn’t it better?”

Andrew: One of the reason why I think it’s important to talk about this and to have an origin story is people are going to ask you where the idea came from until the whole idea is gone and then even afterwards. So you have this opportunity to actually promote yourself. Why not take it?

Second, nobody connects with the facts. What they’re asking for at that point is why? Why should I care? What’s exciting about this? Why do you care? It’s an opportunity for you to infuse some of your message. I know most of us when we’re thinking about starting a business don’t connect with our message. We connect with the fact that I was trying to make some extra money on the side.

But we should think about why this was to make money on the side. How does this connect to who we were? How does this connect to one of our customers? And don’t miss this incredible opportunity. The other thing I’d say having done these interviews, over a thousand of them, don’t lie. I know you think it’s cute when you lie and make something up because you think telling a story means telling a lie. It always comes across as disingenuous, and it can be discovered at some point and it ruins your origin story.

Now your origin at the core is a lie, and it tells people something really damaging about your business. So just search inside yourself and find it. I wish I could spend more time teaching people how to do it, but frankly, most people don’t value it enough for me to spend time teaching it to them.

Chris: Interesting.

Andrew: Here are two small things. I like to spend time on the big picture, but there are two small things that are important. You say you don’t even need a website to get started. Number two, you say frame your first dollar. Why not a website and what would you have people do instead of a website?

Chris: I think a lot of people are going to want to have a website. I’ve built websites. That’s normal. It’s not hard to build your first website, etc. I just always try to think about objections. I try to think about I can’t do this because I don’t now how to build a website. There’s a number of people I’ve featured on the show who have sold something on Etsy and they started selling something on Etsy randomly, like Fiverr or whatever, but they actually ended up building a pretty successful, sustainable side business from it. So there’s more than one way is what I’m saying with that.

Then the frame your first dollar, I’m encouraging people to celebrate their achievements and to celebrate their accomplishments. This is something I struggle with too. I’m always onto the next thing. But because I know how empowering this is, I get emails all the time of like I made my first $150. I had to work 30 hours for it. But I’m really excited about it. It changed my life, etc. Just take that moment, the pizza parlor again, you walk in there and there’s the framed dollar from their first sale or whatever, whatever that is for you, do something for that because it is important.

Andrew: Yeah, not just the pizza guy. Warren Buffett has his first dollar on his desk and he shows it in tons of interviews. The other thing I know that he has on his desk is his graduation diploma from Dale Carnegie & Associates. I know because when we worked for Dale Carnegie, they used to talk about. I like to go and check, “Are they real or not?” I saw a YouTube video. He has his Dale Carnegie certificate behind.

Chris: That’s great.

Andrew: It made me prouder to work for Dale Carnegie when I saw that. You were talking about people who started their businesses on Etsy. I’m thinking about Mary Lynn Schroeder, who interviewed who sells journals now on her own website. It’s called In Blue Handmade. But she did start just on Etsy. I thought what you were getting at with the start on Facebook thing is there’s a movement here, a change in the way the world works, just like my dad would have thought of a store as the heart of your business or the factory and maybe a website is a way to promote that.

Then we told him a website could be a place where the business is, it could actually exist here. I think there’s a new shift in the world, and that is you could actually have a whole business that functions on one of these platforms. Yeah, it’s a little risky, but it’s not as risky as it was five years ago because they recognize the value of supporting people on their platforms.

Chris: Exactly, Instagram, people selling direct on Instagram, building a whole business out of that. It really surprised me, but it’s true.

Andrew: All right. The book is called “Side Hustle.” It’s coming out when?

Chris: September 19th.

Andrew: Do you want me to publish this interview before — I wonder if we could even publish it before September — would you want it published before the publication of your book?

Chris: Around that date would be good, but I want to accommodate what’s best for you.

Andrew: If anyone wants to go see you in person, I see that you’re around the country. You’re still doing these sessions.

Chris: At the time that we’re recording this, I do not have my tour schedule up, but by the time people watch it, it will be up. I’m going to do a 100-city tour.

Andrew: You are?

Chris: So I will probably be in your city. If you live in a major city, at least in North America, I’m going to start with that. Then eventually it will go international as well. That should be on at some point soon.

Andrew: Is this like a book signing thing? Are you going to be teaching something? What are you going to do there?

Chris: So I try to keep it light and fun. I give a talk and then we do question and answer, but there’s also like a chance to connect with other folks who are there, try to make it fun.

Andrew: I went to one of your tour dates before.

Chris: In D.C.

Andrew: I loved it. I like it because I like the audience that you bring in. You’ve got kind of a literate, educated, creative group of people around, which I enjoy spending time with, but they don’t take themselves too seriously, which I also enjoy. for all that.

Don’t forget my two sponsors are the company that will actually help you organize your email properly so you send out intelligent marketing automation. It’s called ActiveCampaign. Check them out at And if you want to do some sales one on one and not kid yourself about how many emails you’re sending out, go check out Pipedrive, Chris, thanks so much for being here.

Chris: Andrew, thanks so much for having me again.

Andrew: Thanks. Bye, everyone.

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