YOP090: Hack The Entrepreneur with Jon Nastor

Zephan: What’s going on Year of Purpose Podcast? My name is Zephan Moses Blaxberg, and today, I’m joined by Jon Nastor. Jon has been starting and running businesses for the past 13 years. In 2011, he discovered the internet as a business, and by 2012, he was running a successful software company from his laptop while traveling the world with his wife and daughter, and playing drums in a punk rock band.

He is the host of the Hack the Entrepreneur show where he has done 200-plus interviews, received 1.4 million downloads, and a partnership with Copyblogger Media and Rainmaker FM. He is also the co-host of the Rainmaker.FM podcast, The Showrunner. He just released his first book “Hack the Entrepreneur: How to Stop Procrastinating, Build a Business, and Do Work That Matters.” Today, he’s hanging out with us. What’s going on, Jon?

Jon: I’m just really excited to be doing this with you.

Zephan: Yeah. Thanks for being here today. I love that we got to meet a little earlier in the week and talk on your show and hear about your book and what you’re doing with entrepreneurs, so it’s great to have you here with the YOP crew.

Jon: Absolutely, my pleasure.

Zephan: I have to ask. How does one go from just running businesses to discovering the internet and just saying “Wow, I can run with this and just be a punk rocker and travel the world?” Like what were you doing before you discovered the internet as a business? Do you remember like was there any specific day where like—did somebody just dropped a bomb on you and you’re like “Oh my god, like I have to do this?”

Jon: Yeah, so a couple things happened. I grew up playing in punk rock bands with like people who were older than me, so I was in high school. I remember like getting picked up from my last exam. I think it was grade 10, and my band were all like in college or not in college, but they were that age, some of them. Right after my last exam, literally, like everyone was just going outside to like go do whatever for the summer, and like there was a van there waiting to take me like across the country and play shows.

I learned from an early age this whole DIY, do it yourself, right? If you want something done, you have to just do it yourself. You can’t wait for other people to hand you things, and so I just took this on in life. Bands ended up breaking up, and I just started playing for fun totally. It wasn’t something I was trying to do for money anymore, and then I just started some businesses offline. From like selling fireworks hilariously as like a store, which did really, really surprisingly well, and I missed, but I refused to do anything offline anymore, but I went into—ended up like working in new house construction.

Again, completely wacky, but it was just—like as you go forward through this like journey of life, right, like none of it really makes sense at all ever, but when you look back, you can like “Okay. Well, that led to that, and then I remember that person in that,” and it’s just this cool thing. My daughter ended up being born when I was—10 years ago. Yes. I was 27. Up until that point, time just like—somebody would ask me like “Hey, remember when we did that?” or “Remember when that happened?” I was like “Oh, yeah. That was like 6 months or a year ago?” “Oh, no. That was like 4 years ago.” Like it just doesn’t matter, right? It’s all blurred together.

Then, I had this kid that every year like 6 months leading up to my birthday was like the biggest thing ever. “It’s your birthday coming.” It’s like “Yes,” but when you’re my age, it doesn’t really matter anymore, but it started to matter because I started to have this definite date every year where I was like “I need to do something more,” so the first 2 years still of her life, I didn’t—I had the offline business. At the end of the second one, I was like “This is crazy,” like I have to be somewhere closer to what I ultimately want to be doing, which was just I wanted more freedom, I want to be able to travel with my family as my daughter aged and stuff.

I couldn’t do that with an offline business because you have to be there, and you have to be working, and doing all the stuff away from a laptop, so I sold the business, and we ended up moving across the country, and I had about a year and a half worth of money just to figure out this whole thing, which I’ve been introduced to by some friends. Just the internet as a business, which I had never thought of before, which is hilarious, and so I spent the time figuring—not so much figuring out. Actually, wasting time and not—and just like information overload, and then I ended up—I actually happened to get another job quickly, which led to me almost owning another company offline, but I actually quit that at the end and was just like “No, I’m going all in on what I’m doing online.” That was like 5 years ago now, and I haven’t looked back since.

Zephan: Yeah. It’s crazy looking back though that it seems like it’s a short period of time. You go from selling fireworks to all of a sudden, you look back and it’s like “Whoa, like I had this online business. The fireworks store is long gone.” I’m actually very familiar with how the bands usually function when you were saying it’s very DIY because one of my good friends used to be in a band, and he said “We are the graphic designers, the guys that had to make the flyers to put up. We are the communications people, the guys that have to get people to the concert venues,” and so it really is a lot of DIY stuff that has to happen there. I think it probably sets you up more for the entrepreneurial world than anything. I bet you could probably write an entirely second book on how being in a band prepared you for the entrepreneurial world, right?

Jon: Yeah, totally. That’s the kind of thing that—again, like as I was going through it, it didn’t make sense that this could be like being in a band would, and living out of a van, and like putting out our own shows, and selling t-shirts, and making them. That was a business per se, but now looking back, it’s like “Wow, yeah.” That was like the best education ever for that like you have no resources, and you just have to make things work, and you just come up with an idea, and you create something out of nothing whether it’s a show, or an album, or a t-shirt, or a sticker, and that’s to me—that’s all entrepreneurship is.

It’s just creating something out of nothing, and when you do that, whether it’s in a band, or online, or offline, whatever you want to do with whatever you want to do it, if you can then turn that something into an exchange of money back to you, then now, you can continue this whole game we call “entrepreneurship.”

Zephan: Yeah, definitely. You mentioned in there that—you said 10 years ago is 27. I’m turning 27 this year, so this is a cool opportunity for me to ask you about 10 years ago, the type of advice that you would give to someone say like me. I started an online business roughly a year ago, so I’m 1 year into this, and it’s tough. For a very long time upfront, you don’t make money. There’s a lot of long hours, and much like in a band, I’m making and designing my own websites. I’m making all my own content.

What do you have to say to people as far as …? They get to this point, and they’re right on the cusp of something great like they’re right on the edge of this huge explosion in a good way in their life in every aspect from business to relationships. What if they’re on the edge of giving up? Like what do you have to say to that just as far as …? You’ve owned and ran so many different businesses and just had a lot of experience over the last 10 years. What do you have to say when someone could just say “You know what? I could walk out at any minute and just give up?”

Jon: A lot of people quit when they’re tired, and you should quit when you’re done. You won’t regret it. You won’t regret the extra work, the extra hours, the extra sweat, the extra blood, the extra tears that you put into it, but you will regret it in a year, in 5 years, in 10 years when you look back on that moment, this very moment in time when you know, when you felt that spark that you were on the cusp of something, and you quit. You didn’t quit when you were done. You quit when you were tired. You quit when somebody told you that you should quit. You quit when you didn’t think that you were quite good enough to do it. That’s it.

You just don’t quit. You just literally just keep going because you will not regret the extra work. Even if it doesn’t lead to exactly where you think it’s going to lead to, which it never will, you have to just not quit. You have to keep going because it’s so worth it. I refuse to look back at any point in my life anymore after that change happened about 5 or 6 years ago where I never want to look back and regret not doing something all in and going for it as hard as I can because I don’t want to know what could have been.

I want to know exactly what could have been because I did it, and I did it to whatever logical conclusion or else, the conclusion of “Yeah, okay. Now, I’m on to something else, and that’s totally cool.” Not like—I’m not saying you have to follow this thing through for the rest of your life for the next 50 years. That’s basically impossible, especially online, the way everything changes, and that’s totally cool. That’s part of the journey, but you will regret quitting. You will absolutely regret it. It’s plain and simple. I’ve talked to hundreds of people now about this, and you never regret doing the extra work. You just regret quitting.

Zephan: Yeah. I think there’s no doubt about it that—I think you regret it if you quit in anything, whether it’s sports, whether it’s certain things in your life or business, but something that you had mentioned just previously was when you had sold that one business, you had roughly enough money for like a year, a year and a half. Money tends to be a big fear for a lot of people, right? You’ve invested so much up front, and then making something happen. I guess 2-part question here.

What’s your take on—have you ever gotten to a point where you don’t really have the money to do it and it’s a scary thing? At that same time, is there a point where you should say “You know what? It’s time to quit,” because I’ve seen Shark Tank episodes where they always ask “How much money have you invested yourself in this business?” They’re like “Uh, like $100,000,” and all the sharks like freak out and lose it. They’re like “Are you kidding me? And you’re still going?” I wonder, is there a point where you should decide to try something different? Also, what do you do when the going really gets tough at least financially?

Jon: That’s a great question. When I had that money, right? I then totally just—I had that money in a cushion, and there was no—my back wasn’t against the wall. I hadn’t earned the ships as they said. There was a way out for me, and that out ended up being going through all that time not doing the work I needed to do, and then needing to get a job. As soon as I got that next job, I was like “Okay. Now, my back is up against the wall. This, I don’t want to continue doing. I need to …” So then, I worked all day, and then I came home and worked like 4 to 5 to 6 to 7 hours a night for like 8 months and was like “I’m focused now. This is crazy that I did this to myself, but I will never do this to myself again.”

The money actually doesn’t help in that way. It’s really the work. You have to do the work. You have to be willing to do the work, and you have to change your mindset from like a consumer to a producer, and you have to start to produce things. No matter if that’s content, or if that’s products, or if that’s books, or if that’s videos, or whatever that happens to be, you have to produce stuff and you have to take time doing it.

You don’t spend 3 or 4 hours a night watching Netflix because you are the consumer of the end product, which is the movie or the TV show, which is produced by somebody. Somebody who’s living a really good life because they get to make a lot of money because they are a producer, and you are the consumer, and you have to just go back to work tomorrow because you have to continue to buy and be a consumer. I’m not saying never watch TV, I’m not saying never consume things, but you have to switch your mindset and become a producer of things. Producers also get a lot of money, so they can buy stuff and consume if they want.

This isn’t an anti-consumption sort of rant. It’s just you have to change your mindset and start thinking that you aren’t good enough to produce things, that you aren’t smart enough that people don’t know you, and that you don’t have any money. You just have to do it, and it’s absolutely essential I think to anyone’s growth and success in life and in business is to make that switch because you’ll never be able to get out of the rut or having not enough time or money if you don’t ever make that switch.

Zephan: Yeah. I think it’s so important just to be able to transition your mindset in general. Look, if you can’t turn off the business mind when you’re with your family, then what good is it, right? I’m sure that your personal relationships would suffer if you don’t have that ability to switch over and transition out of that mindset. Now, does that mean that we’re not thinking about our businesses when we’re with our loved ones? Absolutely not. I think that we should definitely always have our mind on our business and new ideas that could come up, but I think you’re totally right that having that ability to shift mindsets is so important.

Jon: Yeah. To me personally, I blur business in life. Like to me, they’re interchangeable. They’re the same thing. I work from home. My wife has like been able to quit her job last few years. She’s at home. Our daughter now stays home to home-school like we’ve created a life around this and that just involves me and a laptop, sometimes working in my office, or not, or working in the hotel, or on the beach, wherever we happen to be, and it’s just part of life. To me, this is like something I’m trying to instill in my daughter. It’s like “This is just me. I’m a producer of things now.” This is what allows us to do all of this, and it’s just part of life.

Like to me, life is creating things. Life is producing cool stuff like I really want to like die with like a pile of stuff behind me even though it’s all digital for the most parts. I just want to keep creating things, and putting them out there, and doing more, and more, and more of it. I don’t want to be like “Well, it’s 5:00 on Thursday. It looks like it’s time to never think about this like project that I’m like freaking out and so excited about.” It’s just not the life I want to live. I want to be excited by things.

Some days like today, I want to sleep in till 10:00am with my family and just like get up and have like a leisurely breakfast because I don’t start till 11:00. That’s awesome, but then I might also work till 1:00 or 2:00 tonight after my daughter goes to bed because I’m really in to what I’m working on right now. There is that blur. You have to find what you’re in to, right? When you’re really in to it, you will go until it’s done, and you won’t just quit because you’re tired.

Zephan: Yeah. One of the things that you found that you’re really into has been—you’ve got Hack the Entrepreneur going on. You’ve wrote a book. You’ve got a podcast yourself, and you’ve got quite a few other projects going on. How did you discover that this would be the right next step for you to take? Like what sort of thought process went into just saying “This is definitely where I should go. This is what lights me up every single day, and this is what I’m going to do?”

Jon: Okay. Besides like put aside all like the branding, and marketing, and positioning of it that I put into it, I ended up—my family ended up in Asia 2 years ago I think next month. We ended up there for the winter, and then we ended that trip with going to Chris Ducker’s first tropical think tank, which is a small conference at that time. It’s like 25 of us, and there was like mastermind sessions, and there were some really smart podcasters such as like Pat Flynn and John Lee Dumas, and so there was all this talk about podcast. My business, Velocity Page, at the time—it still is, but…was allowing me time and freedom to start something new, and I had podcasted in the past, got my—like the feel of it, but I wanted to do a new show by myself, and so I needed to be pushed.

Then, I spent a few months after that just thinking about it, and then all of a sudden was this like ideas with people in my mastermind and stuff. Somebody created the name for me, then I just decided I’m going to start interviewing people. I had this list of 30 people that I want to interview like brilliant business people. There’s nothing I love more than talking business with people. I know that if I just called them up and asked them for half an hour, they’re probably going to say they’re busy, but if I’m hitting record for a podcast, they’ll probably say yes.

Selfishly, I never interviewed anybody in my life. Literally, we were out at a cottage on a weekend when I finally decided “Okay. This is. I’m starting.” When I got back that Monday, I just sent off some email. On Thursday, I did my first interview. This was like early July, and then I set it up to launch September 5th, which is exactly what I did. Then about 7 or 8 weeks into launching, when I thought it would start to fizzle, and that’s when I’d be like “Woo, I talked to everybody I wanted to talk to. Now, go back to business.” It had this moment like you talked about like that spark where I just felt like I was on the cusp of something.

There was engagement. There was audience that I didn’t have before. There were downloads. There were people trying to sponsor my show. There were people trying to come on my show, and it was this weird feeling of “Hmm, I might be on the cusp of something here. Now, it’s time to go all in.” I went from 2 days a week to 3 days a week, and I really, really focused on my show, making it better, and pushing it.

I started to write for entrepreneurs. I’d write for Copyblogger to really promote the show and do more work around it, and it was because I just felt like maybe this is the time. This is it, and I didn’t want to look back in a year or in 2 years and be like “Oh, I should’ve pushed that. I should’ve pushed that harder.” It’s a lot of work. It’s a ton of work, but I absolutely loved it. Then, that all just—ended up interviewing Brian Clark of Copyblogger, and then that led to Rainmaker, that led to The Showrunner, and the rest is history.

Zephan: It’s crazy how you pushed over the one domino and everything else falls into place. I always tell people my story how I always knew I had to go to California, and I didn’t really know why. Going to California led to travel, hiking, and couch surfing around the country for 2 months, which led to starting this podcast, which led to a number one bestselling book. It’s crazy. If you talked to me 2 years ago and said “Would you have written a book?” I would’ve said “No way.” I grew up with a learning disability. Write a book? I couldn’t even write a 1-page paper for school. It’s just absolutely unbelievable to see where you can go if you just keep the momentum up. Keep it going.

You now have well over 200 interviews on your show. You’ve met tons of people. It’s hard to ask this question because I want to say, is there any like 1 or 2 people that really stood out or anything that really jumped out at you as like a “oh wow” moment like “I definitely need to be listening in to this because even though I have learned so many things over the last 10 years, this is still something that’s so new to me?” Is there any one thing just—that has attributed to maybe your success or even where things have gone for you?

Jon: Yeah. I’m going to quote Guy Kawasaki when he was on my show, and it ended up in my book. He was talking about understanding the math of success and how people—especially when you’re working or like when you’re going to become something, you figure out like how you could make so much money or what you can accomplish in life in general. He says “If you believe somehow you’re set to a certain capability and level of accomplishment, then you’ll never achieve anything more. However, if you believe you can do better and do other things, that growth mindset will allow you to accomplish more,” which is super awesome, which is like really just this idea like you said, how you wouldn’t have expected because of a learning disability that you would be a bestselling author, but now you are.

I was the kid who—I still—I’m the kid now at 37, and I don’t even like I freak out over like seeing a comma like “Should I put that comma there, or shouldn’t I put that comma there?” I also just released a book that ended up on a bestseller on Amazon. The book took me 9 weeks from like the idea, the very first email I sent about it to we’re going to write this and we’re going to launch it December 14th. That was like September, I think, 29th that first email went out. I checked this on a call last week with somebody and like literally like 8 weeks later or 9 weeks later like I launched this book to a number one. I had never written a book in my life. I had never thought of writing a book in my life. I’ve been pushed enough to do it, and I still don’t quite know where a comma goes in a sentence.

The book itself is obviously written very well because it’s been edited heavily by really, really awesome editors that make my ideas make more sense, but if I had thought in any way that I was limited by the fact that—“Jon, how can you possibly write a book? You don’t know where commas go,” I wouldn’t have this book, and I wouldn’t be able to help people and push people forward with this book, and that is essential. You need to overcome that like “Jon, how do you become such a great interviewer on podcasts?” First of all, I don’t think I’m a very good interviewer. Second is I’ve done 200 in the last year and a half, but at the beginning of that 200, I had never interviewed anybody in my life.

Even when I record somebody like my daughter doing something on my phone in video and I hear myself talking back, I hate the sound of my voice, but somehow, I’m a podcaster. The podcast is way too much throughout the week on too many shows, and I hate the sound of my voice, but if I had let that stop me from doing it because I thought that I couldn’t accomplish that, if I didn’t think that I could get the partnership with Copyblogger Media because why would he like want to partner with me, somebody whose voice sounds terrible or doesn’t know how to interview? It’s like “Whoa, what if I just do it? What if I just do it anyways and get good along the way then maybe these things will happen?” You have to do it. You have to.

None of us know what we’re doing at the beginning. None of us know how to start. None of us know how to interview. None of us know how to write. None of us know how to podcast. None of us know how to build software until we’ve done it. Until we’ve done it enough times, and eventually, people look at us and like “Wow. How did you get so good at that?” “Well, I just spent the last 2 years doing this only, only this thing, so if you do that, you’ll be probably better than I am.”

Zephan: Yeah. Part of me thinks that Nike got it right. Just do it. It’s safe advice, but I think—everyone ask me too “How do you do it?” “Well, I started.” I think that it’s so important. You just have to get started, and you just have to keep moving. Hack the Entrepreneur is out right now. Maybe just share with us a little bit about what is in that, what people can expect to get out of that, and then maybe just to round things off, I’d love to hear how the kid in you, the punk rocker still gets to stay alive through your business, through your lifestyle, and through everything that you do.

Jon: Very cool. Hack the Entrepreneur, the book is called “How to Stop Procrastinating, Build a Business, and Do Work That Matters,” so interviewing 200 brilliant, brilliant entrepreneurs that are way smarter than I will ever be. On the end of my show, there’s something I call “The Hack” where I pull out a 10 to 30-second slice of the conversation, something they’ve said, and then I do a short essay on it. I took just their hacks, 50 of them, and I broke them into 10 categories—or no, 5 categories in the book, so there’s 50 of them total, broken into getting started to mindset, to ideas like business ideas, to being wrong and failure, and then ending off in growth.

There’s 10 brilliant ideas in each of those 5 categories from entrepreneurs that literally run like brilliant, amazing businesses from their laptop and travel the world to people who have thousands of employees and make billions of dollars a year, so there’s every sort of aspect of it, both female and male entrepreneurs, and showing how they got to where they are and how they deal with each of these things. Then, it’s all wrapped in with my writing and kind of motivation. It’s not a how-to book to start a business.

It’s really for—if you’re starting a new project, you’re getting started on this new project, you should be getting started again because it’s not necessarily getting started in business, it’s getting started on a project. Also in business, but it’s people looking back and being like “This is how I started the next one and the next one,” and what they learned. The idea is that you can pick it up, and if you need business ideas and how to get to them right now, then read ideas again. If you just made a huge failure, which we pretty much do daily and you need just some sort of—somebody to reassure you that it’s okay or how to get through it, then go to fears.

The best way I can explain the book is that really, I try to write and create it, so that it’s like a giant boot that will kick you in the ass and make you live the life that really is available to you with the internet, and it’s really just you in your own way like you standing in your own way for what you want to do. It really is nothing else, and this is—as much motivation as it is tactics to get you there, but it’s really that boot that will just kick you every time you need a kick to keep going because—yeah. I’ve discovered this life and this sort of internet as a business, and I just—I wish everybody would because we live an amazing period in like in time that never has existed before the way you can scale and reach the whole world from your own home. To me, that’s brilliant and should be taken advantage of by way, way, way more people.

Zephan: Absolutely. This “Hack the Entrepreneur,” is up on Amazon. You also have—I’m sure it’s available on your website. What’s the website URL?

Jon: HTEBook.com, if you want. It will go straight to my site or just hacktheentrepreneur.com. You’ll see the book on there.

Zephan: Awesome. The podcast is over there as well?

Jon: That’s exactly where the podcast is as well.

Zephan: Cool. Any final words just as far as staying a kid punk rocker forever?

Jon: Really, create a business that is around the lifestyle like you—from reading my book, you’ll get the idea from people with thousands of employees to one employee or no employees that you really should create a business around your lifestyle and what it is you want to do. You don’t have to have hundreds of employees if you don’t want. Your business should be exactly and can be exactly as you want it to be. You don’t have to wear suit and tie if you don’t want to. You don’t have to have an office if you don’t want to. You can if you want, but you don’t have to.

Business should be created to create the lifestyle you want, so that allows me to work project-based. Meaning, that I get months off at a time if I want it, and I get to pack up my laptop into a backpack, take my family around the world multiple times, and just travel, and I also get to play still drums 3 times a week when I’m in this city right now in 2 punk rock bands at 37 years old. I’d say that’s pretty awesome. We get to record records, we get to play live shows because I have the time, and the freedom, and the energy to do it because of what my business has afforded me. I do not let my business control my life or my lifestyle, and you don’t have to either. It’s totally up to you to determine what it should be.

Zephan: That’s brilliant. I think there’s no better way to end off this episode. Jon, thanks so much for being here. Everyone needs to check out Hack the Entrepreneur, and I look forward to—I’m sure we’ll run into each other soon at a conference or something like that.

Jon: We definitely will. Thank you so much.