The Transcript

The Two Biggest Keys to Consistently Doing Work That Matters

Voiceover: You’re listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs. DCI features an in-depth, ongoing instructional academy, plus a live education and networking summit where entrepreneurs from across the globe meet in person. For more information, go to Rainmaker.FM/digitalcommerce. That’s Rainmaker.FM/digitalcommerce.

Jerod Morris: Welcome back to The Digital Entrepreneur. I am your host, Jerod Morris, the VP of Marketing for Rainmaker Digital. his is episode number 23. This week represents a bit of a shift here on The Digital Entrepreneur. As I have gotten my feet wet hosting the show and talking in-depth about digital entrepreneurship and building digital business, it’s made me even more curious than I already was about the individual journeys and stories of digital entrepreneurs, people like you and me.

There are so many of us out there doing incredible, inspiring things that we can all learn from. We’re going to spend some time on The Digital Entrepreneur diving deep with successful digital entrepreneurs to learn more about their stories and their journeys and find out what’s working for them and what hasn’t been working for them, so that we can take little parts and pieces and add it to our own toolboxes as digital entrepreneurs.

Today on The Digital Entrepreneur, we’re going to talk to a man who describes himself as, “unable since birth to settle for how things should be.” He constantly aims to satisfy pains and frustrations with products that make people’s lives easier. He’s a proud dad, a husband, and an online entrepreneur who loves creating, marketing and selling cool things online. He’s also a punk rock drummer, a connoisseur of vintage t-shirts and a showrunner. If you listen to my other podcast on Rainmaker.FM, you might already know who I’m referring to. I will tell you real quick who our guest is going to be here in just a moment.

First, I actually have worked with this guy now for over a year. We spent about the first year of our time working together and hosting a podcast together without ever having met. We had never met before. We finally met in person last year at Authority Rainmaker, which was the conference that Rainmaker Digital put on last year. This year we are not doing Authority Rainmaker, we have changed our annual conference now to be focused entirely on digital business. It’s called Digital Commerce Summit. Digital Commerce Summit will be the premier live educational and networking event for entrepreneurs who create and sell digital products and services.

It’s happening in October — mid October, the 13th through the 14th — in Denver, Colorado. If you’re wondering why Digital Commerce Summit will be worth your time, in addition to the great people who will be there, the cool parties, and the musical performance by Cake, what I think really separates our conference — and I’ve had a lot of people tell me this and so I know that’s a view widely shared by people who have been to our past conferences — is that instead of going to a conference where you’ve got six choices at all times for different presentations to go to and it’s hard to choose and you’re not really getting a coherent educational experience, we do it the complete opposite way. It’s a single track. You go from one speaker to the next and everything is curated.

Brian Clark spends a lot of time choosing the speakers, choosing the topics, and then the order that they will present in. What’s cool about it is everybody has the same experience. There’s a different energy to the conversations in the hallways and at the networking events, and a different ability for you as a conference attendee to actually be able to go from step to step to step with your own project, with your own idea or business that you have in your mind and to really work on it.

You don’t always get that at a lot of conferences. You do get it at Digital Commerce Summit, and that’s why we want you to join us. For more information, go to Rainmaker.FM/summit. Don’t wait to do it because the early bird prices are going to be gone soon. This episode is going live on July 14th. The early bird prices will be gone on July 27th, that’s when they expire. You’ve got a couple weeks from the date this episode goes live. Go to Rainmaker.FM/summit to get more information. That’s Rainmaker.FM/summit.

All right, who is my guest on today’s episode of The Digital Entrepreneur? He co-founded VelocityPage. He now runs Hack the Entrepreneur, one of the most popular business podcasts in the world. He’s also my co-host on The Showrunner and he wrote an Amazon bestselling book about his podcast called Hack the Entrepreneur. So let’s talk about the journey of digital entrepreneurship of Jonny Nastor on this episode of The Digital Entrepreneur. Jonny Nastor, welcome to The Digital Entrepreneur.

Jonny Nastor: Thanks for having me, Jerod.

Jerod Morris: It’s great to see you over here, man.

Jonny Nastor: Yeah, totally.

Jerod Morris: Very nice. All right, let’s dive right in. Are you ready?

Jonny Nastor: Cool, man. Yeah, it’s a nice spot over here.

Jerod Morris: It is. It is very nice. Jonny, I’ve always believed — and I think you and I even talked about this before — that the number one benefit of digital entrepreneurship is freedom. The freedom to choose your projects, the freedom to chart your course, and ultimately the freedom to change your life and even your family’s life for the better. What benefit of digital entrepreneurship do you appreciate the most?

How Being a Digital Entrepreneur Has Allowed Jonny to Be Intentional about His Lifestyle

Jonny Nastor: I’m going to say lifestyle and freedom.

Jerod Morris: Nice, why those?

Jonny Nastor: I like hanging out with my family. I like playing drums. I like traveling. Those are all things that don’t do well if you’re too busy and if you are constrained by other people’s decisions and schedules.

Jerod Morris: Do you make a distinction between lifestyle and freedom? I know you mentioned them both. Or do they go hand in hand?

Jonny Nastor: The lifestyle I want right at this very moment and for the last couple of years has been very freedom-based. I don’t know if that will stay necessarily like that. There are going to be times — and there have been times — where I’ve been really focused on growing something and building something. It’s still lifestyle, it’s the lifestyle I choose at the time. But right now it’s really freedom-based. I like to be able to just pick up and go.

Jerod Morris: You love that ability to intentionally chart out your lifestyle, and even as that changes be able to evolve with it.

Jonny Nastor: Definitely.

Jerod Morris: Cool. Let’s go back. I want to go back to the beginning of your journey to becoming a digital entrepreneur, because every digital entrepreneur — as with any entrepreneur really — has unique story and unique things that happened that bring them here. Take me back to before you became a digital entrepreneur. What were you doing and what was missing that led you to want to make a change?

Jonny Nastor: I did a lot of different things in my 20’s. But then in my mid-to-late 20’s I ended up starting a business in construction, which is weird, putting artificials called Cultured Stone on to new houses and things. It was something I discovered. I had moved across the country and was in a band and I had found out through somebody in my band’s sister about this stuff you could do. I had experience in construction because I grew up — my dad’s a contractor. I was like, “Oh, I could make some money on the side while playing drums.” But then, of course, instantly it went from, “You could come in and work for us, learn how to do this.” I looked at it and I was like, “I could figure that out.”

I went and started doing it myself, and then I hired employees and started doing it. It was cool. But then my daughter was born a few years later. By the time she was about two, I was working a lot even though I had employees. We lived right in the city of Vancouver and all the work I did was in the suburbs so I had to commute a lot. I was gone like 10, 12, 14 hours a day, like 6, 7 days a week. It was cool because we owned a house in Vancouver and stuff like that, but it was terrible. I didn’t want to be gone like that anymore.

I had no idea, actually, of the Internet as a business thing at that point at all. But I sold that business. We sold that house. And then we moved back to the middle of the country and I spent a couple of years fumbling my way through some business things. It was only a couple of months when I was back here that I discovered the Internet as a business. Then it took me a couple years to fumble my way through. But I knew that that was what I needed to do, because it was business to me. And it was the same way, where I could leverage things and create, but I could literally do it without leaving the house for 10, 12, 14 hours a day. With my daughter being almost two at the time it was like, “This is totally what I have to do.” That was eight years ago. I guess the rest is history at this point.

Jerod Morris: Even before you started fumbling through things, as you say, you saw that opportunity or the potential for the freedom? Because we talked earlier about designing that lifestyle. You saw that as the outcome if you learned how this whole Internet thing would work. You saw that from the beginning and then worked toward it?

Jonny Nastor: Yeah, totally. It was crazy. I guess I’m one of the old guys of the Internet now, but it’s crazy how different it is now even from then. Going into a coffee shop, you would be the only person in there with a laptop working unless there were students. Now I can’t go anywhere in the world without going to a coffee shop and just looking around, and there’s 10 other people and I can see them all in WordPress sites or just working. I’m like, “Man, this is so cool.” This has happened so fast.

There was something about it, man. I guess it was the freedom at that point too, but it was really the scale and the reach. I was in a small town — I still am for the next month and a half. I’m in a really tiny city in the middle of nowhere. I didn’t want to start a business that was just doing local stuff, because it was way too small for me. It wasn’t exciting. It wasn’t cool. There wouldn’t have been a commute because it’s a small town, but I wanted reach, I wanted leverage and that was that. I could literally create stuff and have people anywhere in the world consume it. It was amazing to me. I just went for it and fumbled my way through and here we are.

The Pride Jonny Felt When His Wife Was Able to Quit Her Job

Jerod Morris: Part of fumbling your way through — you were part of the team that developed Velocity Page, you obviously launched a very successful podcast, Hack the Entrepreneur. You’re now developing an online community to go along with that. So you’ve obviously done a lot online, achieved a lot online. I’m curious, of all those things — or maybe another one that I don’t even know about — tell me about a moment or a milestone or something that you’ve achieved online during your career as a digital entrepreneur that you are the most proud of.

Jonny Nastor: Three years ago next month, my wife got to quit her job. To me, that was the first stepping stone of, “Wow, this is real. This is cool.” And then it was two months later and we went and spent a couple of months down in South America and it was like, “Wow, this is all being paid for by a software business. I’m the only person who works and I don’t really have to even work while we’re here that much.” That, to me, was it.

The following year after that, my daughter dropped out of school as well and became home/unschooled. So now it’s all of us. I don’t know why, that was something I just really pushed for. My wife had a “good job” as she would call it, but she didn’t like it at all. She was in finance at a bank. It’s just something she had gone into, but she wasn’t in any way turned on and excited by it. It was really more of a goal of mine almost than of hers to even quit, and it was hard for her to quit when she could because she just thought she shouldn’t. But now there’s not really any turning back for us.

Jerod Morris: When did that become a goal, because you said that was three years ago? You’d been working online for what, about five years before that happened?

Jonny Nastor: Yeah.

Jerod Morris: Was that a goal from the beginning? When did that hit you? “Man, this would be great if this could happen.”

Jonny Nastor: That was a goal from the beginning. When we were in Vancouver and I had the business and my daughter was just born, my wife got the one year of maternity — whatever it is in Canada, I think it’s about 9 months or 10 months, or a year or something. She took all that, but then at the end of it she just quit her job and didn’t go back. That was cool because I had the business and it was great, but then I sold the business. We moved and she took another year off, but then she went back to work because I didn’t have a business at the time.

Then it was like, “Okay, now I have to step this up until the point where she feels secure to leave again.” This time digitally, not with literally a brick and mortar business. That was my goal. It took a few years to do that. It was really huge to me. We’ve made concessions to that, obviously. You give up a whole bunch of income anyways either way, but it’s still about the freedom. It’s about being able to do what we want and when we want. That’s what we have done.

The Humbling Experience of an Acquisition Gone Wrong

Jerod Morris: Very cool, man. Very cool. Okay, let’s take the flip side of that then. That’s the moment that you’re the most proud of. Tell me now about the most humbling moment in your career as a digital entrepreneur, and more importantly, what did you learn from it?

Jonny Nastor: That’s a hard one. I don’t even know if I’ve ever said this before. I guess I won’t say actual names maybe. You mentioned Velocity Page — cool team, great product. It was a lot of fun. About the first year into it — somewhere around 9 or 10 months — we almost got acquired by a really big company that was going to basically acqui-hire us as a team and bring us into their company. It was cool. The negotiations went on for almost two months, there was papers drawn up and everything. At some point it literally just fell apart via email after we thought it hadn’t. We didn’t know that at the time, but that’s how things worked. We weren’t looking for this or anything, it just came to us.

It was really cool, but it was the most humbling deflation of, “Wow, this is what we’re going to do for the next two years. It’s going to be really cool. I have amazing resources around us and we’re going to see where...