The Two Biggest Keys to Consistently Doing Work That Matters

This week, we talk to a man who describes himself as “unable since birth to settle for how things should be.” He’s a proud dad, a husband, and an online entrepreneur who loves creating, marketing, and selling cool things online. And he’s learned that simplicity and depth are the keys to consistently working on what matters so you can make the impact you desire.

In this episode, Jonny Nastor and Jerod Morris discuss:

  • How being a digital entrepreneur has allowed Jonny to be intentional about building his lifestyle
  • The pride he felt when his wife was able to quit her job
  • The humbling experience of an acquisition gone wrong
  • Why he said “Yes” to a recent project (after getting so good at saying “No”)
  • The technology that is most vital to his success
  • Why he is striving for simplicity and depth

And much more, including our new Rapid Fire round of questions at the end (relevant links below).

The Show Notes

Rapid Fire Resources

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 this can go,” to, “Wow, that was brutal.” It shouldn’t have — but in hindsight it actually was a huge part of the whole team falling apart after that. Because it was weird. It was a weird thing that we didn’t expect, we weren’t looking for, and we didn’t know how to deal with it.

It was amazing to have my show Hack the Entrepreneur, because I got to talk to so many really smart people who had been through VC funding — just on my show. So many of them were just, “No, man. Most deals fall through, even right at the last second when the paperwork’s being signed. It’s just how it works, man. It’s not you.” And I was like, “Okay.” It wasn’t devastating in that way, but it was definitely humbling.

Jerod Morris: Wow, I would imagine so. What was the hardest part in the moment? Was it that this whole thing came out of the blue and you were maybe swimming a little bit out of your depth? Did you feel like that? Or was it just that it didn’t happen and that maybe caused you to question whether you were as valuable as you thought? What was it about the actual experience when you were going through it that was the most humbling?

Jonny Nastor: I thought I was kicking ass. I was the one doing all the negotiations and it was really cool talking to so many different people within the company and escalating my way through. It went from total acqui-hire like, “You’ll work for us in San Francisco.” It was like, “No, we’re not, because we’re three people who are all about having our own freedom and being autonomous. We’ll work with you and we will fly there, but we’re not going to be coming to your office 9 to 5. It’s just not what we’re doing.” That was all pushed back against but then accepted — and so many things. It went from, “Wow, this is cool. I can really do this part of the business,” to — it just totally fell apart and I didn’t see it coming.

It was humbling in that way. And then to be like, “But this was my main job and the rest of the team were totally leaving it to me.” We’d talk about things after we get off calls and emails and stuff, but they were like, “No, man you got to run this. You got to do this. You got to do this.” Then it just fell apart and I had to go to them and be like, “Dude, it’s done.”

It was hard man. It was super hard. It is still right now saying it because I don’t talk about it, but it was something that definitely — I don’t know what an MBA or something would cost in business, but to me this obviously cost probably more and I think taught me more about myself. About some bigger aspects of business that I never pushed myself to and I just got pushed into. I had to learn a lot of stuff quickly about that whole world which I know will come back and help me a lot. I’ll be so much better going to it next time.

Jerod Morris: It’s interesting, because I think to really be successful — especially in something like digital entrepreneurship where you do have so much freedom but chart your course, you really have to have a North Star that helps you make tough decisions. I’m wondering if you regretted it then and if you regret it now how that happened.

You talked earlier about how the biggest benefit to you of digital entrepreneurship is the ability to intentionally design your lifestyle. You talked about being proud of the fact that your wife got to quit her job and here it seems like it fell through in part because you guys were holding steadfast to this idea of designing your lifestyle. You didn’t necessarily want to move and then you wanted to keep some of those things, and that maybe was a reason why it fell apart. Do you regret it at all? Would you do it differently if you could? Or did it really turn out the way that it was supposed to and then had the benefit of being a learning experience?

Jonny Nastor: I guess there’s two answers to that. It’s a multi-part question. I don’t have regrets, just in general. I refuse to have them, because to me there’s no point. I can’t go back and it doesn’t change anything. But then if I could go back, obviously I would play it different only because I know what I know now about the process. But I don’t blame myself for it. There wasn’t something that I typed into an email or said that dropped it. It’s literally just part of the process. I’ve been talked through with enough people that are way smarter than me and have been through this way more times than me successfully and unsuccessfully that this is just part of the process.

The biggest thing that I’ve actually learned, and anybody could take this if you ever end up in that opportunity — which we talked about actually doing at one point because there was a slight bit of interest — the thing to do apparently, is if you have someone and you’re in serious talks with them, you should start conversation with somebody else at the same time quickly and try and get two offers rather than one because it shows interest and it puts a pressure. Otherwise they hold all the cards and you don’t, which is weird.

That seems a weird backhanded way to do things, but apparently that’s just how negotiations can be done. That’s why when you’re going out looking for VC funding, you go out for a round and you just talk to a lot of people at once. You might have 10, 20, 30 meetings, and then people can just tell you. Everybody else knows that you are going to a whole bunch of people. There’s a general interest in you, not just a one-off, “You have nothing, we have everything. Do you want it?” Kind of thing. I would change it because I know more now. But, no, I don’t have regrets, man.

Jerod Morris: Okay, let’s fast forward to now. You’ve got this burgeoning Hack the Entrepreneur empire with your incredible show that you have, the Hack the Entrepreneur book that came out, and the online community that you’re starting. What is the one word that you would use right now to sum up the status of your digital business as it stands today?

Jonny Nastor: I guess I can’t say freedom. I’m gonna say, I don’t know, man.

Jerod Morris: You can say freedom, but you have to say it like William Wallace in Braveheart.

Jonny Nastor: I don’t know this one. One word that would sum up the status of my business right now … is cool a word that I can use?

Jerod Morris: Cool is a word.

Jonny Nastor: My business right now is so just a part of my life and what I do that it’s really awesome in that way. To the point where I almost don’t even consider it a business. It’s funny because when I talk to people like that, especially with my mastermind, they stop me every time. “Dude, a business is something you create something and you get paid for. That’s a business.” I’m like, “I know, but it doesn’t seem like it should be a business.” “You get paid for it.” “I know, but I’m just having conversations with really cool people.”

It doesn’t really make sense. I don’t know, man. It’s cool. It really is. It feels crazy that I can get paid to do this. I get paid fairly well to do this, something that I enjoy doing so well and it becomes a product, a piece of media that I can then sell advertising and stuff around. It’s crazy and really cool.

Jerod Morris: It is, it’s very cool. Clearly. What’s at the top of your priority list right now?

Jonny Nastor: The top of my priority list right now is launching a new product, my first ever product in the music industry. It’s got me staying up at night and not being able to sleep and really excited.

Jerod Morris: What’s the next step? Obviously I know you probably don’t want to get into all the details, but what’s the next step for that project? What are you doing next to take it to the next step?

Jonny Nastor: We’re launching — in hopefully two weeks — the MVP version of it. Right now I’m obsessed with being a product guy. Like with Velocity Page I was the product manager. I’m really obsessed with product and on-boarding processes within software, so I’m obsessively reading things and getting ideas and going over it with the designer. Going through the actual product and creating a cool on-boarding process for this new product.

Jerod Morris: There’s that word again, cool.

Jonny Nastor: Yeah, man. It is cool. It’s going to be cool.

Jerod Morris: It is.

Jonny Nastor: It’s music, so it’s bringing together something I’ve never done. And it’s completely separate from everything I’ve ever done. It’s weird how I stumbled across it and how obvious of an idea it seems to be now but it doesn’t exist. I’m excited. It’s going to be fun.

Why Jonny Said “Yes” to a Recent Project (after Getting so Good at Saying “No”)

Jerod Morris: How did you make the decision to say yes to this? Obviously that means that you have to take your eye off the ball. Maybe not take your eye off the ball, but that diverts resources that you could be using on Hack the Entrepreneur and some of the other stuff that you’ve already built. I know that you’re very careful with what you say yes to — as any successful person is. How did you make that decision to say yes to this?

Jonny Nastor: Took a long time. Six months ago or so. The idea is called Showlist. It’s literally going to be where you can list all the bands you’ve ever seen live and the bands you want to see live and the bands you’re going to see live. Then you can share it socially. It’s basically a Goodreads, but for shows and concerts instead. So there’s going to be discover-ability.

I created my own, “Showlist,” in a Google doc six months ago while I was at a music festival with my wife in Austin. I wanted to share it with people so I started Googling, “Where do I put this?” There’s people who just had it on Facebook. One guy had it on some weird blog — he had his own list. There’s hundreds of comments anytime somebody put their list of bands. I was like, “Wow, that’s cool.” So I immediately bought Showlist. No, I didn’t, I bought right then.

Then I just let it sit. I let it sit for 4, 5 months because I was doing some other things. Then Velocity Page shut down, which gave me some free time, but then I still didn’t jump on it. Then it just seemed like the right time. I kept avoiding it almost intentionally because it seemed like maybe I was saying yes too quickly because I came up with the idea, I bought the domain. So many things I’ve done before really quickly, “I got to do this project.” Then it fizzles. I really let it sit and stew. It just kept coming back to me here and there, then finally it was just like “No, this is exactly what I should be doing.” Then I worked on a name. I worked on finding a developer who’s a good friend of mine and was really good at launching MVP products. I just decided to go for it, man.

Yeah, I definitely defaulted to no for many months and when it just kept coming back enough times and then when my plate just naturally cleared, it seemed like the right thing to do. It’s so separate from Hack the Entrepreneur that it doesn’t seem like it’s muddling anything. It’s not going to divert attention because it’s completely separate to me. Just completely separate. I’m either focusing on one or the other, but it’s not where I’m half doing this and half doing that. To me, it really make sense business-wise. And personally it feels really good to be back with a team building some cool software.

Jerod Morris: Tell me a little bit about the biggest challenge that you’re facing right now.

Jonny Nastor: The biggest challenge I’m facing right now? It’s a good question.

Jerod Morris: Don’t say working with your Showrunner co-host.

Jonny Nastor: Biggest challenge, I’m going to say finding simplicity. I just spent a full week in Lisbon, Portugal with two super smart dudes. They are the guys in my mastermind. Tearing apart my life and my business for them for 24 hours. It’s been brought to my attention and made very clear and I fully agree and it makes sense that I needed to find simplicity. Simplicity within Hack the Entrepreneur and simplicity within whatever I do outside of that — this being Showlist right now.

But I lost focus on Hack the Entrepreneur I think. I was trying too many different things. I think I had lost what had got me to where I was with my people a little bit. I hadn’t been writing my weekly newsletter as much just because I’d been muddled and confused by a bunch of stuff. It was because I was overthinking too many things.

My biggest challenge right now is getting simplification within the business. Cutting out things that aren’t either furthering me or furthering my business or furthering my audience in any way. I need to just be better. I need to be a better writer and I need to be a better interviewer and have better conversations. Those are the things that people want from me and need from me. Those are the things that I want too — to grow — and will grow the business. Simplification is the biggest thing right now. Rather than trying to add anything else right now, I’m looking at every different aspect of everything I’m doing and trying to just hit delete on as much of it as possible.

Jerod Morris: One area that can simplify our lives if we’re smart about it or that can definitely overcomplicate things if we’re not is our tools. The set of tools that we use as we go through every day. Do you mind if we open up your tool box a little bit and take a peek inside?

Jonny Nastor: Yeah, let’s do it.

The Technology That Is Most Vital to Jonny’s Success

Jerod Morris: What is one technology tool that you think contributes the most to your success as a Digital Entrepreneur?

Jonny Nastor: You’re going to hate me for saying this.

Jerod Morris: Am I?

Jonny Nastor: I’ll say the Rainmaker Platform.

Jerod Morris: I don’t hate you for that.

Jonny Nastor: I’m going to say it especially because this past week — and I know when I say this that anybody listening is going to be like, “Oh, yeah.” I have — I don’t know how many other domains that I don’t use. Whatever, we all have them. They all run WordPress. It was Saturday or Friday or something night, and those emails started coming in, “Your WordPress site has been updated.” I used to hate that so much because it was literally like, “Oh my god, what broke?” I’d have to go and update plugins and then some of them wouldn’t work because they don’t have updates yet. It was the biggest nightmare. They always do it at night, it seems. Then my whole night is ruined and I’m trying to do it. Now they come, I’m just like, “I don’t care,” because I don’t have to deal with any of it. It’s so awesome.

Jerod Morris: You don’t have to worry about the plugin updates.

Jonny Nastor: I see them and I got so excited, “Oh, I remember I having to worry about this two years ago.” To me that’s not freedom. Having to worry about that kind of stuff. It doesn’t fit into what I’m trying to do. Definitely the Rainmaker Platform.

Jerod Morris: Very cool, very cool. What is the non-technology tool that contributes the most to your success?

Jonny Nastor: Small, little, yellow Post-it notes.

Jerod Morris: How do you use those?

Jonny Nastor: I write three things max on the top one every single day. Those are the three things that I need to do today and I just do them. No apps. No fancy things. Just literally, “What do I have to do?” Write it on a Post-it note, stick it on my desk in front of me and don’t stop until that’s done. Then I can start going and playing on Facebook and Twitter if I want to.

Jerod Morris: Let me ask you a question. Something like this — we had this interview scheduled — does that count for you on those three things or this something extra? I find that to be something of a challenge when I’m trying to plan my to-do list and what am I going to do when you have certain things scheduled. Do you count those?

Jonny Nastor: No. This to me is, “production” is what I call it. Interviews — whether I’m being interviewed or doing the interview — are absolutely necessary for what I’m trying to accomplish with Hack the Entrepreneur. But it’s production, it just has to happen or else nothing else exists. It’s not a to-do. It’s on my calendar, it’s there. But yeah, not at all, man. It wasn’t on my list today.

Jerod Morris: So there’s a distinction between production and then to-do’s? To-do’s are more like three big things that will move you forward or help you take the next step. Production is like, “This stuff just has to happen.”

Jonny Nastor: Yeah, you stop production and the media business that you’re owning no longer exists. It’s not a matter of, “Well, I got to do this today.” No, it’s understood that I have to do production. It’s just how it is. That’s not every day, because it’s not on my calendar every day. But the day that it is, it’s just essential that that’s what I do.

Jerod Morris: Even when it is, even when you’re overloaded, do you still have three things? Do you try and say like, “Okay, I might have a little bit less time so let me pick three things that are a little bit smaller that I can fit in?” Are you making those decisions each day?

Jonny Nastor: For sure. Tuesday’s my big production day and I’ll have three things tomorrow, but I won’t have three big things at all. If I have one big thing on the list that’s going to take me an hour or two hours or three hours to do, I’ll put two small things on there. But that’s it, man.

Why Jonny Is Striving for Simplicity and Depth

Jerod Morris: Cool. All right, moving forward. I asked you earlier for one word that you would use to sum up the status of your business as it stands today, and you said, “Cool,” which is a great answer. If we talk again in a year, and I certainly hope we do — something would have gone very wrong if we’re not talking in a year. What would you want that one word to be then?

Jonny Nastor: Depth.

Jerod Morris: Why depth?

Jonny Nastor: It goes with simplicity. So Showlist and Hack the Entrepreneur, I’m going to simplify both of them so that I’m only working on the things that really, truly matter to me and to my audience, but I’m going to go deep on those things. Right now — or up till a month ago — I was going wide on too many things, and it was like 10% Jonny on this, 3% on this. I want 100% on the things I’m doing. The couple of things I’m doing, I want to go all in. I want to be the best writer I can be. I want to be the best interviewer I can be. I want to take Showlist to as many thousands of people as I can.

Jerod Morris: By the way, I want to get on Showlist. I’m not real big on sharing a lot of things on social media, but I think you may really tap into a nerve there. I would love to share shows I’ve been to, especially little shows of smaller bands, and be able to review them. That be great. You’re right, there’s no great way to do that.

Jonny Nastor: I know. One of the sticking points that came back to me during that six-month process was that conversation that I had with you and Demian last summer. During the conversation — I was interviewing you guys and then you guys each mentioned like a show you had seen and both of you astounded me. How did I not know this about you guys? I, all the sudden, saw you in a completely new light. I was like, “I want to know that about people. I want to know that they’ve seen these bands.”

Jerod Morris: It does. It can tell you something about somebody. It does.

Jonny Nastor: Yeah, that’s what I think is really cool. It’s not just bragging. It’s really interesting to me to see those kind of things.

Jerod Morris: Yeah, very cool man. Very cool. All right, are you ready for the new Digital Entrepreneur rapid fire round of questions?

Jonny Nastor: Absolutely.

Jerod Morris: All right, here we go. If you could have every person who will ever work with you or for you read one book, what would it be?

Jonny Nastor: Difficult Conversations: How to Discuss What Matters Most. I believe Harvard Business put it out. There’s like three or four authors, but it’s Difficult Conversations.

Jerod Morris: I have Crucial Conversations. Is that different authors?

Jonny Nastor: Yeah, I never heard of Crucial.

Jerod Morris: Okay, yeah. I was thinking that I had read that before, but okay, I have Crucial. Difficult Conversations. All right, and why that one?

Jonny Nastor: I think every relationship that takes any depth and really goes anywhere meaningful through employees or creation of stuff — products, services, whatever it is, business — it takes a lot of difficult conversations. Being able to understand that on one side is one thing, but if I could do that and also the person on the other side could bring those conversations to me, I think we would be able to achieve much greater things.

Jerod Morris: Yeah, okay, Difficult Conversations. If you could have a 30-minute Skype call to discuss your business with anyone, anywhere in the world, tomorrow, who would it be?

Jonny Nastor: Wow. I should have prepared. Let’s say Pieter Levels.

Jerod Morris: Pieter Levels.

Jonny Nastor: Yeah.

Jerod Morris: Why Pieter?

Jonny Nastor: Because he’s got a real knack for scaling for himself to cool web apps that do really well, and he has a really good knack for creating a good story around a product that could be kind of boring and therefore getting PR. The thing is that I probably could talk to Pieter tomorrow if I wanted, but he is a super smart dude from Holland. He created Nomad List and a few other things that have really taken off, and he’s just a really smart dude. I think he could help me a lot right now.

Jerod Morris: Nice. All right, question number three. What is the one email newsletter that you can’t do without?

Jonny Nastor: Hiten’s SaaS Weekly, Hiten Shah.

Jerod Morris: That’s a good one.

Jonny Nastor: Yeah, it comes out every Monday morning so I got one today, and it’s a curated list. I’m into software so it’s the one for me.

Jerod Morris: Yeah, that’s a really good one. I highly recommend that one. What non-book piece of art had the biggest influence on you as a digital entrepreneur?

Jonny Nastor: That’s one’s easy. Frank Turner is a musician from London, England. He has a song called Eulogy. That one, to me, is it. It’s all summarized by all the things that he might not become but he wants to at least know when he dies that at least he blanking tried.

Jerod Morris: Yeah, nice.

Jonny Nastor: That to me is creation — to at least know you tried.

Jerod Morris: Yeah, very cool. All right, what productivity hack has had the biggest impact on your ability to get more meaningful work done?

Jonny Nastor: Definitely doing only three things a day and only doing one thing at a time. Simplification. Not jumping around to things. Don’t move until you’re done.

Jerod Morris: You mentioned getting one thing done at a time. That can be an issue for folks with focus and distractions. How do you make sure that you focus just on the one thing and get that done without getting distracted?

Jonny Nastor: I think it just takes practice. I’m the most distracted, most erratic, most want-to-get-up and just do or move to the next page person. I think I’ve just been doing it long enough because I know that that’s what it takes to do the work that I want to do and achieve the things I want to achieve. I don’t want to spend eight hours a day or ten hours a day working when I know that I’m actually only doing an hour and a half worth of work anyways. I’m not that kind of person that just wants to brag about how much I worked. I’d rather work for two or three hours and then go do something else but know that I feel so accomplished because I did so much. It really just takes practice.

It’s like meditation to me. When you feel your mind start to wander, just bring it back. When you feel yourself wandering to Twitter, just bring it back. Don’t curse yourself. Don’t tell yourself you’re no good or you can never focus. I’m the least focused person ever, and if I can do it, anyone can do it. Don’t be hard on yourself. Know that it’s going to take a few weeks to get into that habit of staying focused.

That’s why I use the yellow Post-it notes and everything. It takes technology, obviously, to be on a computer to work, but I don’t want to be on a phone checking the Wunderlist app or something so that I can see and then it’s like, “Oh a tweet came,” or, “Oh, that’s a message from my wife.” You know what I mean? I have to outsmart myself in that way. I really, truly do. I just know that this is how to get the work done I want to get done.

Jerod Morris: Yeah, okay. Finally, what is the single best way for someone inspired by today’s discussion to get in touch with you if they want to?

Jonny Nastor: Email me

Jerod Morris:, very good.

Jonny Nastor: That’s it.

Jerod Morris: Johnny Nastor, thank you for joining us on The Digital Entrepreneur. I almost said Hack the Entrepreneur. Thank you for joining us on The Digital Entrepreneur, man.

Jonny Nastor: Thanks.

Jerod Morris: It was exciting learning more about your story. You said some things today I didn’t know. That was good, very interesting.

Jonny Nastor: Cool, man. Hopefully it wasn’t a difficult conversation.

Jerod Morris: No, it wasn’t, but it was a crucial conversation. I’m glad that we had it. It was deep and it was cool.

Jonny Nastor: Yeah, it was fun, man. Thank you so much for having me.

Jerod Morris: Cool. Thanks, Jonny.

Thank you very much for tuning into this episode of The Digital Entrepreneur. A reminder: go to Rainmaker.FM/summit and make sure that you check out what Digital Commerce Summit is all about so that you can decide while the early bird prices are still in effect whether or not you want to attend. I sure hope you will.

I will be there, many folks from our Rainmaker Digital team will be there, and we really hope to be able to meet you and discuss your project with you and discuss all the great presentations that you’ll see. Go to Rainmaker.FM/summit. Also, just a quick note, we should be here next week with another episode, but I do want to let you know that my wife is pregnant. We are down now to the final couple of weeks. Obviously our daughter is now the one who is in control and she can come whenever she decides to.

At that point whenever she does come, I will probably take a little bit of time off, which will mean that The Digital Entrepreneur will probably go a couple of weeks without a new episode. If you come here next week and you’re looking for an episode and it’s not there, that will be the reason why. I had to go to see about a girl in the immortal words of Sean in Good Will Hunting. In this case the girl, of course, will my new daughter, whom I’m very excited to meet. If she has not come yet then we will be back with a new episode next week, so stay tuned for that.

Either way, I’m very excited to continue on this new path with The Digital Entrepreneur. Talking to Digital Entrepreneurs like you and me. Learning about their stories. Learning about their journeys. If there is anyone that you think would be great to profile that you’d love for me to interview, just send me a tweet @jerodmorris, J-E-R-O-D M-O-R-R-I-S. I’d love the input and always would appreciate your thoughts on the show. Connect with me over there. All right, everybody. Talk to you soon.