Chris Guillibeau is back for his second time on the show, this time with the message from his new book, Side Hustle.  He wrote it to the fully employed who want a side hustle to 1) have something they enjoy and have freedom in, 2) want another stream of income, and 3) want the security of not having all their eggs in one basket. Chris is as down-to-earth as they come and is all about practical, step-by-step application. Side Hustle is right now sitting in the top 200 overall books on Amazon’s bestseller list because this is guidance people want. Thanks to SmartBiz Loans and Goddard School for supporting this episode.

Show Transcription

[00:00] Welcome to The Ziglar Show, where we bring you the most powerful pioneers in personal development and the inspiration to take action in your life. I’m your honored host, Kevin Miller, and today Mark Timm and I bring you the launch of a new Ziglar Show format! I’ll tell you more in about 30 seconds. This show features Chris Guillibeau, back for his second time on the show since being with us in show #386, April 28, 2016, titled “How to dominate by opting out.”

[00:29] This time we have Chris back to dissect the message from his new book, Side Hustle.  He wrote it to the fully employed who want a side hustle to 1) have something they enjoy and have freedom in, 2) want another stream of income, and 3) want the security of not having all their eggs in one basket. Chris is as down-to-earth as they come and is all about practical, step-by-step application. Side Hustle is right now sitting in the top 200 overall books on Amazon’s bestseller list because this is guidance people want.

[01:04] Chris is a true friend of Ziglar. He came to fame as the blogger and author of The Art of Non-Conformity, and is a guy on a mission to travel to every country in the world and share his travel hacks, which he has done!

[01:15] Before we start the interview, really quickly, let me tell you about something new. This show is the beginning of a new show format. For about a year now, we’ve posted one show per week. Starting now, we go to three shows per week, always in the same structure.

[01:31] Monday will be the main interview with a premier guest who is a rock star leader in personal development. Harnessing the Ziglar Wheel of Life, we will stay focused on four areas we need strength in for overall life success: The Mind, Our Work, Our Health, and Our Personal Skills & Ability.

[01:53 ] We’ll be bringing you the best of the best. Wednesdays we’ll take that same guest and get into their…personal life. The habits, successes, and weaknesses in their personal development journey. You’ll hear great counsel you can apply, and realize they are striving and real humans — just like you.

[02:14] Friday we’ll give you a ZigBomb, where that same guest again gives their favorite Zig quote and what it means to them. We’ll take that quote to our social media channels and ask questions around how to walk it out, and share them in a Q&A show which I’ll generally do with Ziglar Premier Speaker, Michelle Prince.

[02:39] We really feel this format will give you more direct value for your life. Let us know what you think with great reviews in iTunes, or if you want to offer some feedback on how we can do it better, just email  us at

[02:55] With that said, here, CEO of Ziglar Family, Mark Timm and I bring you…Chris Guillibeau.

[03:03] So, Chris, aside from being an entrepreneurial guru, which is the subject of our talk today, you are a renowned world traveler. So…a question. If you had to get on a plane this moment and fly somewhere outside the U.S. and remain there 30 days, where would you go, and why?

[03:23] Ok, you know I just got off the plane and I will go off on a plane tomorrow, it is kind of a constant thing. But at the moment I am on a book tour, which is its own kind of animal — which I love, so I would love to go Sydney, Australia. It is one of my favorite places. I haven’t been there in a long time, so I would love to go back there.  

[03:48] That place was Zig’s favorite, too. I ask you the same question, Mark. You are a travelling guy, where would you go?

[03:54] The same question has been asked to me by my 17-year-old son, and I told him that I would love to go to China. There are lots of reasons why and I am not digging in but just saying the culture there, the history, is so rich.

[07:36] I came to The Tattered Cover Bookstore for your tour of The $100 Startup probably in 2012 with my friend Justin Lukasavige. My lips were beyond chapped and I couldn’t concentrate; paid the most I’ve ever paid for Chapstick, but it was really good. I think I still have a scrap in a tube. But tell us how Side Hustle differs or continues from The $100 Startup.

[08:13] Great question. I would say it is completely different. The $100 Startup is essentially encouraging people to become entrepreneurs. It is actually a documentary of people who are not entrepreneurs and actually leave their jobs to do that. Whereas Side Hustle is an essential message saying, “Hey, you don’t have to quit your job!”. Lots of people actually love what they are doing, they like to believe in the organization they are working with. But, at the same time, they do realize that they also need an extra source of income. So, it is way to tell people that you don’t have to invest extra, you don’t have to risk, but you can utilize your skills to do extra and establish an extra source of income.

[09:27] You are fond of pointing out you are the consummate entrepreneur who admittedly attests to being willing to work 24 hours a day for yourself rather than work one hour for someone else. At 47, I’ve spent approximately two years as an actual employee. Probably the best it could be as an employee, but still didn’t’ fit me. But the perspective isn’t necessarily attractive for all! With you, is it more…rebellion? I know I have authority problems. Or is it more just…freedom, passion, and creation of your own art?

[10:03] I think it is fair to say both. You know, when I was a teenager, I dropped out of high school. I had a lot of issues, but eventually I got translated into something positive. But I do have something like going my own way, but not everybody does have that, of course.  But the other side, the freedom, the independence I discovered when I do something for myself, I actually love that kind of way of life. I think everybody likes having more options, more choices.

[16:13] You write primarily to people who have a regular day job. Where do you find the most resonance? They

  1. Want to do something they enjoy and have freedom
  2. Want another stream of income
  3. Want the security of not having all their eggs in one basket

[16:45] I think it is those things and also the desire of making different creative outlets. You know, you like your job and you have skills using them in your job, but you have other things you like as well. Also, creating a backup plan and trying to build a bridge for the future. I think the biggest one, through all, is security. And I just wanna create more security for myself. And I think what most of the people respond to is the idea of they can do it while being busy. It is not only for the people having full-time jobs, but a full-time mom, or a single mom or a single dad, they have like less than an hour a day to invest in the project, but they want to utilize that hour in the project.

[22:53] Step number one in your book is build an arsenal of ideas, and you start off in the book with people who took little things they did…writing reviews on fish tanks, photographing a wedding…and turning them into small or large revenue makers. Do you encourage people more to brainstorm any random ideas, or just look at abilities, expertise, knowledge and experience they have as a starting point?

[23:22] You know, I do think it is important, since people have limited time and you also wanna maximize your efforts, to  use your skills towards the directions to make more money. So I do wanna encourage people to go to the path of, you know, self-interviewing not just the things you like, not just the hobbies, but beyond that and working on your skills, all the skills you have, all the different things you know about in the world, or the things people used to ask. So I don’t think it is bad to brainstorms different things, but as people are busy, try to get on the right track and then develop the idea.

[25:51] To connect with Chris, go to You can get his new book, Side Hustle there, or wherever you get books. On Amazon as of this recording, it’s sitting at #237 in all books, that’s impressive. And, again, to submit your side hustle to Chris, go to

 [29:45] You, Timothy Ferriss, Jordan Harbinger, John Lee Dumas, a lot of the influencing names out there as authors and podcasters, I know a lot of folks with families are prone to discount or at least lament guidance because…they have family and such. Would you speak to that?

[30:12] I would say ii’s somewhat…first of all, I will never say to you to get up two hours earlier and write a book. Most of the people never get sufficient sleep, you know, because of kids or they have to go to work. So I am trying to reduce that burden, first of all, and say that you have to spend some time on that, but you can reduce it as much as possible. What you do is actually count — and it is super important. In some cases, being busy is also a benefit, because if you have unlimited time then you are gonna mess around a lot. And I’ve done this myself. I had spent so much time surfing on the Internet, and trying different kinds of ideas in the world, but by having — let’s just say limited of time — as long as you have the right to make the decision, then your work will be more effective.

[33:47] Aside from those results, what is YOUR main motivation for your audience? Is it helping them make money on the side, having more security, or spending time working at something they enjoy, the end goal in and of itself, or the means to a greater end and vision you have? If your book sold 20 million copies and spawned a movement, what would the movement be? How many people who have successfully started a side hustle did NOT also experience some significant personal growth?

[34:30] I would say I am really motivated by stories of positive change, like I have done something that changes other people’s lives: “I have read you book, listened to your podcast,” or something. I love getting emails from people who say, “You know, I read your book and I quit my job,” or “I read your book and started working on this project.” I do find it very motivating, but I also found that I am not the only one who is doing the work. I personally find it encouraging.  

[36:10] So, what is the biggest excuse people most commonly use for not starting a side hustle?

[36:20] The biggest excuse I would say is time. That is what I have heard people saying, that “I don’t have time to start with it,” or “I don’t have time to work on this.” Time is like highly more valued than money.

[36:55] Definitely I hear that, too. I do hear about money, too. That is more like a perceptional thing than more optical. I heard most people saying, “What kind of business you think requires $5000 in investment,” or “In my budget, what kind of business do you think I can start.” It is a wrong approach; it is a wrong action, you know, from the beginning. In the same category after the time, I usually hear people saying, “I don’t know what to do, actually. I had the idea but I don’t know what will be the next step. I got this far but I got stuck somewhere.”

[38:22] You cite that everyone should have a side hustle. There was a book I really liked, published seven years ago by a guy named Matthew Crawford, ShopClass as Soulcraft. A lot of his soapbox was how we as a culture have gone toward higher education and being a “knowledge worker.” We find a specialized task we can fulfill in a big corporation…a big machine, where we are a cog. But then the layoff comes and that one, specialized task that is part of a big machine is all we know and we don’t have a craft, a stand-alone skill. Do you feel that’s a relevant challenge for many people, or they merely need to do a better job of translating their skills to more tangible applications?

[39:25] One of the things that I talked about a lot in my last book is that I don’t think that everybody necessarily need to become an entrepreneur. But I do think that everybody should learn to think entrepreneurially. That is the kind of the mindset you don’t learn in school. It is something that you can learn; it is not rocket science.   

[40:29] Most, if not all, of the stories start with, “So and so wanted ____, so they did _____.” They wanted _________________. I think you know Donald Miller, who we’ve had on the show and are having on again soon… and I have implanted in my mind, “A good story is made up of a character who wants something and overcomes conflict to get it.” How much does that line play out in the stories of people you are involved with?

[41:04] The truth is that you mentioned some of my favorites, and those guys as well. I think for some people, obviously, that’s gonna apply, I think some people are a little bit scared off in some other ways. I think I am trying to just simplify, or take the pressure off, and don’t let you think like this is a huge thing and you have to overcome. Let’s just do something simple. So first-time people get to earn money outside from their jobs, it feels good, it feels empowering. So I am just trying to fast-track people to get to that point.

[48:02] You hit the big question everyone has with their idea or ideas then…is it viable? How often do you truly hear an idea and think… “There is absolutely really zero marketplace opportunity for this idea”?

[48:49] I agree, probably because you don’t know until you try it. I think the other thing that people are worried about is validating their ideas in advance. Also, it is an entrepreneur culture that you must validate your idea before you go to market. But some of the things we are talking about we are not able to validate. So I think the only way to find out if your idea will work or not is not to ask any expert or not to ask your buddy; it is just you can try and see if it works.

[49:50] You give two categories that most ideas fall into, “selling a product” or “providing a service.” Not to dissuade anyone from either, but with most people, which do you find is often more feasible and profitable? Majority from your shows and stories?

[50:24] You know, a lot of things can be your product or service. You can influence people in some way, you can transfer knowledge in some way, you can create product for that, can create a service of coaching or consulting, teaching. I don’t think one category is better than another. I think this is one where we talked about the skills a lot, I think this is one where your personality matters a lot, because this is your side hustle.

[51:40] So you have a literal table to measure which of someone’s ideas are best, the “Side Hustle Selector.” So, the Clif notes:

  1. Feasibility
  2. Persuasion
  3. Profit Potential
  4. Efficiency
  5. Motivation

And you rank them as high, low, and medium. Give a quick explanation of each.

[52:00] Let me simplify a little bit. So, this is called a side hustle selector, and this is the whole process in the book. This is very intuitive. Take you about five minutes to complete or 10 minutes, max. So let’s just take three of the factors to make it easy for the people who are listening. So you got feasibility, which is like relatively how hard you think it is to use the idea of running it 24×7 a day. Can you see a path from where you are? Then profitability, you know how profitable your idea will be, which of the ideas has most potential to make the most money, you know, in the least amount of time? And the third factor you say is motivation. I do think that the side hustle is important for you, but I also think that side hustle should not be something you drift into, but something you are excited about.

[54:05] I want to end by covering three big aspects of a successful side hustle from your book:

  1. Target market
  2. The compelling offer
  3. Tell a story

Out of all these areas, where do we generally miss the step?

[54:38] Let’s take the second one, which you said is the compelling offer. I think when people are developing their first side hustle idea, they are very much focused on the idea which is good, but we just consider that we don’t buy ideas. We buy products and services. So I encourage people as quickly as possible to go with the general idea of what actually you are offering, what product do you have. So the offer includes the pitch, the benefits, and also the price. So I am trying to get people to get the idea of not only income but also the offer.

[57:41] Chris thanks you for giving us your time and sharing with us your thoughts.