SEO Podcasts

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 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 bandsIveseenlive.com 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 Jon@hacktheentrepreneur.com.

Jerod Morris: Jon@hacktheentrepreneur.com, 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.

The Transcript

How Joanna Penn Designed the Lifestyle (and Career) of Her Dreams

Voiceover: You are 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.

Jerod Morris: Welcome back to The Digital Entrepreneur. I’m your host Jerod Morris, the VP of marketing for Rainmaker Digital, and this is episode No. 22.

In this episode, we are going to continue our interview series with the esteemed panel of digital commerce practitioners who will be speaking at Digital Commerce Summit this October in Denver. If you missed our recent episodes with Brian Clark and Chris Garret, Joanna Wiebe, Sonia Simone, and Pamela Wilson, they are easily accessible as the previous five episodes in your Digital Entrepreneur feed.

How to Take Your Digital Business to the Next Level

Jerod Morris: If you enjoy those episodes and if you enjoy today’s discussion with author, entrepreneur extraordinaire Joanna Penn, then I highly recommend that you consider joining us in Denver this October at Digital Commerce Summit, where you will discover smarter ways to create and sell profitable digital products and services from some of the most successful digital entrepreneurs in the world. People like those that I’ve already mentioned, as well as folks like Rand Fishkin of Moz, Jeff Walker, Laura Roeder, Tara Gentile, Chris Lema, Chris Ducker, and many others.

Plus, of course, you’ll get to spend a few days hanging out in a theater full of like-minded people who are pursuing the goal of building a successful business around digital products and services–like you may be right now–and, of course, people who want the financial and professional freedom that can come from doing that.

It’s a great way to build your network, and it’s a great way to build your notebook with ideas that, who knows, might change the course of your business. That can happen at conferences like this. I know that because it’s happened to me at conferences that I’ve gone to.

Early bird tickets are still available for the conference for at least a few more weeks, at least as of July 7th, 2016, when this episode first goes live. The early bird tickets aren’t going to be there forever. In fact, we’re taking them away later this month, so don’t miss out on getting the best value. You can go to Rainmaker.FM/Summit for more information.

All About Joanna

Jerod Morris: Well, today on The Digital Entrepreneur, as I said, you’re going to be learning from Joanna Penn. Joanna, if you don’t know her already, is a New York Times and USA Today bestselling fiction and nonfiction author. She’s done it all independently. She’s not just an author. She was also voted one of the top 100 creative professionals in the UK by The Guardian in 2013, a recognition of her success as a not just a creative, but also a businesswoman.

Clearly, Joanna has an impressive professional life and so many essential lessons. She can teach so many essential lessons that we can all learn when it comes to the power of creating ‘intellectual property assets.’ This is a buzz term that Joanna uses a lot, and it makes so much sense once you hear her explain it. This concept is how she’s built her thriving business and how, in her words, she’ll still be making money 70 years after she’s dead.

Well, I had the chance to chat with Joanna about this and much more on a recent members-only case study inside of Digital Commerce Academy. What surprised me about our conversation is that I was actually more fascinated by her origin story–how she went from being a self-proclaimed ‘cubicle slave’ who ‘should have been happy with her life but wasn’t’ to where she is today because it certainly didn’t happen by accident.

She made a series of intentional, strategic, and well-thought-out choices to systematically transition out of her IT consulting job and into being one of the world’s most successful independent authors. It’s a story that so many of us who are aspiring or even current digital entrepreneurs can learn from and relate to because I know there’s so many of us. Maybe we’re in a current job, but we have this dream of doing this over here, this business idea, maybe something creative, and we can’t seem to get to that point, to get to that transition point.

Well Joanna did it, and there’s so much that we can learn from her story. I’ve decided that for this week’s episode of The Digital Entrepreneur, I’m going to play you an excerpt from that conversation because I got a lot out of it, I got a lot out of re-listening to it as I prepped for this episode, and I think that you’ll get a lot out of it, too.

We discuss how Joanna started and failed numerous businesses, actually, before one stuck. We talk about the important decision that she made about how to view her job that actually set the stage for her growth as an author and to her becoming an entrepreneur. We also talk about the book she read that changed her life, how she dealt with her inner frustrated creative–and I think a lot of us deal with a inner frustrate creative–and much, much more.

I will tell you real quick that what I’m going to play for you here right now, it’s audio that is recorded from an GoToWebinar session, so it’s not perfect. Fortunately, Joanna comes through much clearer and much better than I do, so please just suffer through my short question interjections. They’re very short, and Joanna does most of the talking because, as I said, the audio for her is much better than me.

She provides some incredibly useful insight, so I didn’t want less-than-perfect audio to keep me from bringing this to you here on this podcast. I really hope you enjoy it. Here now is an excerpt from my Digital Commerce Academy chat with Joanna Penn.

How Joanna Started and Failed Numerous Businesses Before One Stuck

Joanna Penn: Like many people, I went to university and did a random degree. In England, you can do random degrees. I did a degree in theology at Oxford, and out of Oxford, you tend to get recruited to these big firms, like a bank or a consultancy firm. I became an IT consultant straight out of university in order to pay off my student loan.

Like many people, getting that first job, you’re not so much worried about what it is. It’s just making a living. I never thought, back in 1997 this was, that I would end up doing that job for so long. So many of us, we don’t even make a decision, or we just do something by default, make a choice, and then wake up years later and go, “What the hell just happened?” That’s basically what happened to me. I had a fantastic time. I certainly appreciate my years in business, but it was 13 years before I got out.

Basically, I ended up implementing accounts payable in large corporate financial departments, which is just not at all creative. I did this across Europe. Pre-2000, I did a lot of the Y2K bug, which everyone will laugh about now, showing my age, and traveled all over Europe, Asia Pacific, came to America. Basically, I was paid very well to do a, as we said, corporate-slave-type job.

As I put on the screen there, I should’ve been happy with my life because I was paid well. I traveled. I was doing a job that my mum thought was great, that society thinks is great. I was paying my taxes early. I was the epitome of what a good girl should do out of Oxford University or any university–get the right degrees, do the right job–but I was basically really miserable. I almost felt ashamed of being miserable at work because I had a good job. I should’ve been happy, but I just wasn’t.

I started to try and figure what the hell was wrong. I actually left my job a number of times. I was a consultant, so I could come and go on projects. I started a scuba diving business briefly in New Zealand, which didn’t go very well because the price of fuel, insurance, a boat, and skipper and crew–recommendation, don’t start a scuba-diving business. Then I also did property investment and really just didn’t enjoy that and lost money on that as well.

The Book Joanna Read That Changed Her Life

Joanna Penn: Before I started considering what do I actually want my life to look like, and we’ll get into this in a minute, the turning point for me was always implementing more accounts payable into a train company, rail company in Australia. I was just crying every day. I just couldn’t work out why I was so miserable, so I started reading a lot of self-help.

Just one book–well, I’ll probably mention a lot of books as we go through this–but the book I read that changed my life was The Success Principles by Jack Canfield. The very first principle is take 100 percent responsibility for your life. This is a big deal because I thought I was taking responsibility, but what it said was, all the choices you make over your lifetime that mean you’ve ended up where you’ve ended up. The continued choice to choose a job for money and stability over my happiness was part of the big deal. That was the as-was situation and the point at which things changed.

Jerod Morris: You said to me that you found that you weren’t willing to have the pain any longer, and you’re talking about existential pain here. I think that we find that, for a lot of us, whenever we want to make a big change, we have to get to that point where the pain of the status quo, of not acting, becomes so great that we just can’t, and that forces us to do the hard work of change. You talked about this book being a big influence.

Were there any other moments, big moments that really signaled, “Hey, this is the time I’ve got to really start being intentional about designing the life I want because I’ve got all these things–but yet I’m not as happy as I should be, and I’ve got to do something different”?

What Inspired Joanna to Leave the Job She Didn t Love

Joanna Penn: As I said, I was listening to a lot of self-help audios. I was reading a lot of books, and I guess I just looked at how short life is as well and just wanted to do something that would make me happy. I started researching how to enjoy what you do with your life. It was at that point where I thought I should write a book.

Although I’ve always been a reader and I’ve written journals, I’d never written a book. I started researching that and finding out a bit about that. Probably, another big deal was I got into affirmations. This was around the time of The Secret. I want to say that The Secret was missing a big thing, which is the action that you have to take.

But one of the things that they did introduce me to was this idea of an affirmation. I wrote down, “I am creative. I am an author.” At the time, I couldn’t even say that out loud. So I wrote it down on a little card, and I would say it in my head “I am creative. I am an author.” This is going back to 2006 now. Then, eventually, I started whispering it on my route home when I was out walking and things. Eventually I could say it out loud. I certainly wasn’t creative, and I wasn’t an author at that point. But there was this point where I was like, “I just have to make this change.”

Why Joanna Decided That She Was NOT Going to Go Up the Career Ladder (and What She Means by a ‘Pizza Hut Job’)

Joanna Penn: Around then, I also decided that my job was not going to be a proper career anymore. Everybody knows that, when you’re in a job that you want to stay in, you do extra stuff. You go above and beyond, generally, but you don’t work eight hours a day at most normal jobs. You work longer hours. You do certain things in order to go up the career ladder.

I made the decision that I was not going to go up the career ladder. I was going to treat this job like a Pizza Hut job. I can’t remember where that phrase comes from now. But basically, it was a job to pay the bills, but I was not doing anything more than the basic amount of work in order to keep my job. I did a good job, but I didn’t do anything more than I should have.

If there was a chance to leave early, like at four o’clock in the afternoon, I would go home, and I would start. I was writing, and I was learning and all this type of thing. Essentially, that crux point came when I was crying at work, and I just went, “That’s it. I have to transition out of this,” but it did take quite awhile to transition.

Jerod Morris: I think it will for a lot of people. It’s one thing to have this realization, to start making these affirmations, and it’s quite another thing, then, to take the next step of being truly intentional about what steps you want to take next.

Obviously, you don’t just want to quit your job, have nothing, make this rash decision, and don’t have anything set up. This is what I love, that you did that. You asked yourself, “Okay, I know I need a change. I’m realizing there’s these other things that I want to do more than what I’m doing now, but it’s more than just what you’re going to be doing. It’s what type of life do you want to live.”

As you told me, you decided that you wanted to indulge your inner introvert. You wanted to travel. You wanted to be location independent. You wanted to create things in the world. How important was it that you actually sat down and figured these things out in terms of helping you actually create that reality, which you have now?

The Importance of Embracing Movement and the ‘Zig-Zag’

Joanna Penn: Firstly, I would say it’s very easy in hindsight to look back and figure out these things, but when you’re actually in the moment, I normally tell people it’s a bit like skiing down a hill. Even if you haven’t skied, you know what it’s like in that you don’t just go straight line, top of the hill to the bottom of the hill where you wanted to end up. It’s really zig-zag. You have to zig-zag down the hill, so you’re not always pointing in the direction you think you’re going.

Also, you need to be moving in order to turn, so you actually need some momentum before things appear, before you can turn and try the next thing. For me, the mistakes I’ve made before that–so for example, the scuba diving business–the location-independent decision came from running a location-dependent business, where we’re dependent on a physical boat, a physical island, physical people.

That decision on location independence happened earlier on when making a living on the Internet was not such a big deal. That was back in 2004. I know some people were online, but I wasn’t. That came from that. The introvert thing, I am an introvert, which means I get my energy from being alone. I’d just been working in a department of around 400 in an open-plan office everyone knows what an open plan office looks like, and it was awful.

For an introvert, that kind of noise level and people vibration is very, very tiring, and I had a lot of migraines and a lot of physical pain from just that over-stimulation that introverts struggle with. That was another thing that was like, “Okay, I need to be able to work on my own.” Like many introverts, I’m not a team player.

And if people don’t really know what they are personality wise, I really recommend Quiet by Susan Cain. Even if you’re not an introvert, chances are that your partner or one of your children or parents is. Quiet by Susan Cain, really good book to try and understand people.

How Joanna Dealt with Her Inner ‘Frustrated Creative’ Who Had a NEED to Do Something That Mattered

Joanna Penn: Then the creative thing came from being an IT consultant. Basically, everything you do when you work in a technical space, different to what we’re doing technical-wise, but I was implementing these systems into big companies. What would happen is we’d implement all this stuff, and then a year later, they throw it all out and implement something new. I felt like everything I ever did disappeared, and it really upset me.

It was like, “What is the point? All I’m doing is earning enough money to go out for a nice dinner and pay the mortgage and whatever, but I’m not leaving anything in the world. I’m not creating something original.” That upset me. I just felt that it was all a bit pointless, so that’s part of the existential pain. Maybe I just am, or was, a frustrated creative who was desperate to do something.

Maybe some people listening feel that way–that need to do something and create something, but this seeming inability to do it. The travel thing is I’m just a travel addict, so that was always going to happen. But tax-deductible travel in order to do book research is fantastic.

Jerod Morris: Hey, hey, I like it.

Joanna Penn: Those are the things that I thought about in terms of the life I wanted, and I thought, when I considered this, I wrote this first nonfiction book, which at the time was called How to Enjoy Your Job or Find a New One. I actually rewrote it. It’s now called Career Change, which is a much better title.

Essentially, I thought I was going to be a professional speaker and also make money online selling training courses. Although I am a professional speaker as I’m coming to Denver to meet you guys and speak and I do sell training courses, I’ve ended up being first an author, which I didn’t really think that would happen at the time.

Jerod Morris: That will happen. Like you said, it is to a certain extent like skiing and there’s zig-zagging, but being able to have these overarching things that you wanted to make sure were in your life helps you go from point A to point B–even though there were a lot of zigs and zags in there. It hasn’t been exactly what you thought. You’re doing a few different things than what you thought.

What I found especially interesting is, as you told me, “I’m just going to find out how to get into self-publishing and learn about to do it,” because you made this decision that you wanted to write, that you wanted to create. I love this mindset that you had here because it’s very much the mindset of a digital entrepreneur.

What was it that motivated you to want to do this on your own instead of going more traditional routes to just say, “Hey, I can figure this out. I can learn this, and I can figure out how to do it on my own”?

How Joanna Got into Self-Publishing Without Any Publishing Experience at All

Joanna Penn: That first book, which is now Career Change, I wrote it, and of course, at the time, I didn’t know anything about the publishing industry. I was also in Australia, was learning from people like Darren Rowse at ProBlogger and Yaro Starak at Entrepreneur’s Journey. I was in a blogging space where, of course, the general atmosphere is do-it-yourself, can-do attitude.

Also, queried one agent with that book, so it was a nonfiction book, which generally, if you want a traditional publishing deal you should sell based on a proposal. I finished the book, and I was like, “Now I’m going to publish it.” When I got this email back from the publisher, it was literally just one of those ‘we’re not interested’ emails.

Then I started to understand what traditional publishing was, that it was based on this scarcity model, this gatekeeper model. Also, even if you got an agent and you got a book deal, it would take a long time for the book to be out there. I’d just written this book, and I was just changing my life–and I was not going to wait. I started to look at self-publishing.

I was also lucky in that I was in Australia because at the time, back in 2007, 2008, self-publishing was vanity publishing, even still in America to a point, although the Kindle was starting to emerge at that point. Also, I was amongst professional speakers, and a lot of professional speakers self-publish because they can sell their books at the back of the room. There’s a much more positive attitude towards self-publishing amongst professional speakers, so I was glad for that.

Basically, I went, saw traditional publishing, “I’m going to do this. I’m going to do this quickly. I’m going to make some money”–and then I basically proceeded to make every mistake in the book, which we can talk about in a minute. The upshot of that mistake, and this is why mistakes are so important, the mistake that the scuba diving company made my decision to go online.

The mistake of my initial self-publishing, I started my blog, TheCreativePenn.com, Penn with a double N, and to share what I had learned. That was the beginning of what has become a massive part of my business. These mistakes are important along the way.

Jerod Morris: Yes. Yes, they are. We’ve talked about your timeline a little bit. Let’s go through it just where everybody can understand how you got from where you were to where you are. We mentioned 2006, and we mentioned this decision that you made to change. As you said, you changed your mindset to a Pizza Hut job.

You weren’t going above and beyond. You weren’t doing extra. You were doing what you needed to do for your job, but you had set aside any thoughts that it might be a career. Yet it wasn’t really practical to leave right away. I think a lot of people who have a day job and then maybe a side hustle, they end up daydreaming about just leaving their job right now and being able to just pour all of their energy into this new thing–which sounds exciting, but isn’t that practical.

Why did you decide to take this more deliberate approach, and why do you think it was better than just waking up in 2006 and just saying, “I’m out”?

Why Joanna Took Deliberate Steps to Leave Her Job (and Why It Makes the Transition Easier)

Joanna Penn: First of all, that picture–so people looking at the slides or in the recording, get the slide–I think that’s the last time I wore a pinstripe suit. I really like that picture because I don’t wear a pinstripe suit anymore. I’m one of these creative people who wear colors. It’s really funny to look at that picture.

I didn’t know very much back in 2006. What I did know was how much money I was making in my day job. I’m a businesswoman. I want people to be very clear about that. We’ll come to the timeline, but I left my job in 2011. This year was the first year I made more money than I ever did in my day job. It’s taken quite a long time to build up the business to where it was more than it was when I was at the point.

The reason being, and I always say this to people, how much are you worth in your first year in any job? Of course, not very much. How much are you worth in year five at any job? Still, not massively, but at 10 years in any job, you’re going to be one of the top people around there. I think we have to look at it in that way.

Basically, in 2006, when I made some kind of decision to get out of IT consulting and accounts payable, I was still earning very good money. Basically, my husband, at the time we weren’t even married, we bought a house, so we had a mortgage. We had a car. I think we had a motorbike as well. Financially, it was going to be impossible to just leave my job, but what I also knew was how little I knew about publishing, about online business, about speaking. I started the process of learning the skills I needed.

Although I didn’t have a degree in writing or online marketing or online business, I have spent a lot of money. As obviously people listening are investing in their education, this is what you have to do is invest in what you need in order to change your job a little bit further down the line. That was around 2006. I started to invest in my education with some idea that I would exit my job at some point.

Jerod Morris: Again, you had to sacrifice maybe doing the extra, going the extra mile to continue shooting up the corporate ladder, but then you substituted that time with researching, learning, and doing some of those new things. It’s always a give and take. We certainly don’t suggest that folks just quit their job and jump in.

You’re going to have to take that time from somewhere to learn and to start building it on the side. I think this approach that you’ve shown is a good one. We go to 2008, and this is an example of an important step you took. You started your website. Tell us how that impacted and helped keep you going.

How Going Down to Four Days a Week in Her Day Job Changed Joanna’s Life (and Why Choosing a Website Name Needs to Encompass the Life You’re Going to Lead)

Joanna Penn: Basically, at the beginning of 2008, I self-published that first book, How to Enjoy Your Job or Find a New One. Realized how little I knew. In fact, basically what happened is I had all these boxes of books in my living room. Then I realized I didn’t know how to sell them, so I embarked on this journey of learning about online sales, which is incredibly important and has become the backbone of everything I do now and what all online entrepreneurs have to do.

TheCreativePenn.com was my third blog, and I think that’s a really important thing to tell people. I started the first blog around the book, so I had one book. I thought, “Oh, I must start a blog around my book,” which I don’t recommend if you’re intending to be an author with multiple books.

Then I started another one, which was about what I was learning about online business and the blog about blogging, which we all know can be a dangerous thing. I started The Creative Penn, so my third site, in December 2008. I thought, “It’s crazy. This is the affirmation to reality thing.” My affirmation had been, “I am creative. I am an author.” I didn’t believe I was creative at that point, 2006.

In 2008, I was far enough on the mindset journey that I could call my business TheCreativePenn.com because I thought, “Anything I do for the rest of my life can be under this umbrella because I intend to be creative.” I could become a painter and that website name would work. This is a big tip from me with your main website is go big enough. If it’s a lifestyle brand or a personal brand like mine is, it needs to be big enough to encompass the life you’re going to lead. If I had SuccessfulSelfPublishing.com, that would’ve been a very tiny part of who I am now.

I think that’s important, and then I moved down to four days a week at my day job. I went to my boss and said, “Look, can I take 20 percent pay cut in order to work four days a week?” Everybody knows, if you work four days a week, you still do the same amount of work as five days. I basically said, “Look, I’ll take that extra day,” and taking that extra day made a lot of difference to me because I spent that extra time, again, learning more, building my blog. I started a podcast in 2009. I did more training. I started writing more books. I started writing a novel.

Going down to four days a week is a really massive lifestyle shift for a lot of people, but I really credit that with changing my life because the time has to come from somewhere, basically. Better to give up the money, 20 percent of your income, instead of just ditching it all.

Jerod Morris: Right. That led to 2011 when you left your job and started doing what you’re doing now full time. At that time, you were only making, and correct if I’m wrong, but you were making about $2,000 a month from the side job. It’s not like you had built it up. You even just mentioned, you just reached the point where you’re actually replacing the income that you had been making before.

You may not be able to have that perfect, “Okay, I’ve totally replaced this before I leave,” but you’re still going to have to take that leap of faith at some point. For you, it was in 2011. How did that feel? Did you feel ready? Were you scared? What was going through your mind at that time?

Joanna’s Leap of Faith and Downsizing to Make Her Dream a Reality

Joanna Penn: Basically, my husband was very super supportive, and basically, I’d been the main wage earner and helped fund his master’s degree. Then once he finished that master’s degree and got his job, I said, “I want to try and make a go of this. It’s my turn.” Basically, we agreed that well, first of all, I saved like six months income, so we had a cash buffer in the bank.

Secondly, I said, “After six months, if I’m not making more money, if this is not going in a positive direction, then I will go back to my job.” Pretty much, let’s face it, all of us here are employable people. We can all get another job. It’s one of those, “Oh, what’s the worst thing that can happen?” If the worst thing that can happen is you have to go and get another job, it might not be as good as the one you had, but is it that big a deal?

Basically, I was at this tipping point of, “If I don’t have more time to create more intellectual property assets, make more connections, or learn more, I cannot escape this small figure. I need to have more time in order that I can grow this.” I should also say that we totally downsized. We sold our house, sold our investment property, sold our car. We actually moved back to England from Australia, which some people wouldn’t consider downsizing. We really made our life a financial risk-free zone in order to give this a shot.

Again, a lot of what I’ve done sounds quite radical now, but I think if you really want it, then you will do whatever it takes. Certainly, as I’ve said, I’m a businesswoman. We’ve never been poor, and my husband worked as well. Basically, we’ve worked really, really hard, but we’ve downsized and changed our financial risk in order that I wouldn’t feel like I had to go back. That gave me some real breathing space. But yeah, September 2011, left the job and never went back, basically.

Jerod Morris: Now here’s my favorite detail about this whole story. In 2015, your husband quit his job so that you could work together, which is just the happiest of happy endings. It’s not even an ending to the story, but at least, as we bring up to the current time. I love that.

What Creating the Ultimate Freedom Means for Joanna and Her Husband

Joanna Penn: Yeah, and this was probably my biggest financial goal. I hit the six-figure goal. I had earned six figures before, so that wasn’t quite so exciting. I had a certain figure in mind that, if we hit it, then my husband could leave his job.

He quite enjoyed his job, but at the end of the day, it’s about what kind of life do you want. The getting up and commuting and being on someone else’s terms, and also being told that if I wanted to go travelling for research, he had to ask permission … I know people on the line who are entrepreneurial, asking permission is just the worst thing. I hate asking anyone’s permission to do anything.

I was like, “We have to get you out of your job. Then we just have to ask our own permission, so we can go on holiday when we like.” We were just in Spain last month, walking in the south of Spain. We’re just doing things together now and working together. He’s learning online marketing. That pretty much represented an almost 10-year journey from both committing to go in this direction, and now we’re looking at what is the next step and basically running a global media company, as these things turn into. It’s actually really great for me to have someone else on my team. I have a lot of freelancers, but to have someone on my team here is fantastic.

Jerod Morris: It ends up coming down to freedom. That’s what being a digital entrepreneur is all about. That’s why digital commerce is such a great opportunity for that, for being location independent, for building a business that you own, that you run, and that you make the decisions on. It gives you, then, the freedom to do what you want.

And I imagine that is why you said this to me, which is that, “I am seriously happy in my new life,” because you have freedom now that you had all these things before. When you said, “I should’ve been happy with my life,” the one thing that you didn’t have was freedom, and now you do. We see how you feel about that, which is happy.

Why Joanna Is Now ‘Seriously Happy’ in Her New Life and How ‘Work-Life Balance’ Doesn t Really Apply When You Love What You Do

Joanna Penn: It’s funny, isn’t it? We start talking about freedom there Tony Robbins in one of his books had this, “You must come up with this one word that will help you guide decisions in life,” and my word was ‘freedom’ and still is freedom. So you’re right. That’s the point. Also, I think what is so amazing is I really love what I do.

I love writing fiction. I love writing nonfiction. I love speaking and helping people on the blog. I love the business side. I love the marketing. I get a lot of comments from people who say, “How do you manage work-life balance?” I’m like, “You don’t understand. This is my hobby, my passion, my job, and my income.” When people talk about lifestyle design and also lifestyle business, this is a lifestyle business, but the income is scalable.

I know we’re going to get into this, but what is so exciting about books, courses, and intellectual property assets that you can exploit in all different ways is, that income is scalable. As I said, this year we went over this tipping point of making enough that my husband left and making more than I ever did as a consultant. Now it’s exponential. I’m 41, and I expect to be creating more assets every single year for the next 50 years. That’s what’s so brilliant. I’m seriously happy as a creative, but I’m also seriously happy as a businesswoman. I know that people listening are also interested in that business side.

Jerod Morris: All right. Well, thank you so much for tuning into this episode of The Digital Entrepreneur. I hope you learned a lot from that conversation with Joanna. Again, Joanna will be speaking along with me, along with Brian Clark and Chris Garrett, Joanna Wiebe, Chris Ducker, and all of the other people whose names I mentioned earlier, Rand Fishkin and Jeff Walker. I could go on and on, but all of us will be sharing the stage at Digital Commerce Summit.

We really hope that you’ll join us. It’s in October. It’s in Denver. It’s going to be fun but also really educational. The way that the conference is going to be structured is with a bias for action, a bias for movement. We want every single person who comes to the conference to be further along with their digital business than when they left so that you have some real takeaways and some action items so that when you’re on the plane flying back, driving back, or however you get there, that you’ve got some plans to make. You’re ready to hit the ground running once you leave the conference.

Again, early bird tickets are still there. We’re taking them away later in July, so make sure that you get on them while they’re available. Go to Rainmaker.FM/Summit.

All right, everybody, thank you again for tuning into The Digital Entrepreneur. We’ll be back next week with a brand new episode. Until then, take care.

The Transcript

Is Your Email Marketing Leaving Money on the Table?

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’m your host Jerod Morris, the VP of Marketing for Rainmaker Digital. For those of you scoring at home, this is now episode number 21. I’m joined today by a couple of familiar voices. First we have Brian Clark, the Founder and CEO of Rainmaker Digital. Brian, welcome back to the show that you started.

Brian Clark: Do you really think people are scoring at home?

Jerod Morris: No, it’s a callback to an old Sport Center catchphrase. I’ve always wanted to say it.

Brian Clark: I do appreciate the reference, and I did get it.

Jerod Morris: We’ll see how many other people do. Now, a person who definitely did not get that reference. We also have Chris Garrett, the Chief Marketing Technologist at Rainmaker Digital. Chris, I hope this appearance helps cure your podcasting withdrawal symptoms that I’m sure you’re still going through.

Chris Garrett: Yes, that it does. And I can confirm, I did not get that reference.

Jerod Morris: Yes, that was a sport and goal reference.

Brian Clark: Inside baseball.

Jerod Morris: Yeah, I know.

Chris Garrett: I don’t even get inside baseball. I have to have somebody explain that one to me.

Jerod Morris: All righty. We are not going to talk about baseball today on this episode of the Digital Entrepreneur. We’re going to talk about email. We discussed this topic back when we did our five episode series on the elements of the modern marketing website a couple months ago. We’ll have that episode link for you in the show notes. Email actually kicked that series off. The episode was titled, “How Email (Still) Creates the Profit Engine of Your Digital Business.” If you are not yet convinced that you need to be building an email list, go back and listen to that episode and then get started building an email list.

For this episode we’re going to assume that you understand the importance of building an email list, are in fact already doing so, and are at that next-level stage where you’re looking to become more sophisticated with your email marketing. You’re working with autoresponders, you want to get into tagging and segmentation, and perhaps improve what you’re already doing in that area.

That’s our big idea today, which is to stress the importance of thinking in a more sophisticated and strategic way about what you’re doing with email. Also to discuss how we’re building these tools and features into the Rainmaker platform in a way that no one else has really done because of one key huge difference which we will get to here in a bit. First, Brian, I want to start off by asking you, why have tagging and segmentation become such essential elements of an email marketing campaign?

Brian Clark: It’s all about that providing a more personalized experience. When we’re putting together our email sequences everything depends on the action or inaction. There are usually a couple to several variables that are always at play. Isn’t it smarter to speak to someone based on what they actually do, what they show interest in, than some one-size-fits-all autoresponder stream? That worked great for me in 2001 to 2005, but we’re in a very different world now.

Jerod Morris: Yeah, we are. The message that you are delivering to your audience needs to adapt. We’ve talked about this idea of the right message for the right person at the right time, and that’s what this allows you to do. Chris, Brian and I were actually talking the other day about the difference between tagging and segmentation. What is that difference? Can you explain what tagging and segmentation actually are from a more technical standpoint and what the difference is between them?

Why Tagging and Segmentation Are No Longer Nice-to-Have Email Features

Chris Garrett: Segmentation is what Brian has just talked about, talking to the people who are interested in the topic about that topic, and not sending them information that they’re clearly not interested in. You segment them. You put them into groups. So this group is interested in red widgets and this group is interested in blue widgets. You can do that by putting them on two different lists, or you can have one master list and add information about them. Brian is interested in basketball and Jerod is interested in football. It can be one list called “sports,” but that information about what they are interested in could be a tag. It could be a custom variable.

It’s a piece of information about that subscriber or that prospect. Back in the day, with the early sales CRM processes, you would say, “This is a prospect. This is a warm lead. This is a qualified lead.” You would say, “This person has shown interest. This person is ready to be closed.” That’s a piece of information about them. Just like you would tag a blog post to say it’s about science fiction or romance, you would tag a person to say, “This is what we know about them.”

Jerod Morris: It’s so important to be able to do this to have flexibility. I’ll give you an example from a project that I was working on with a certain email provider. I wanted a way to send messages to the people who visited — this was for The Assembly Call — people who watch the show the most. If people had visited that page ten times I would tag them a certain way, but I actually had to create a separate list for those people and send it to a separate list and pay separately for that list, as opposed to it just being a tag for those people, those subscribers all within my list already that I could just email.

Brian Clark: That’s what I have to do now, and I’m not shy, it’s AWeber. Chris, when are we moving me to Rainmaker? It’s so unwieldy when you have to create a new list.

Jerod Morris: Yeah, I hate it.

Brian Clark: It doesn’t make sense. And I think AWeber has some much more expensive advanced features that may include this, I’m not sure. But my opinion is, this is just email in 2016. This isn’t advanced email marketing. This is just email marketing. MailChimp and AWeber and all these people who are vanguards of the industry are saying, “Sure, we’ll sell you that for this much more.” I disagree with that approach, because I think everyone needs to be doing at least basic segmentation and tagging. It just makes much more sense than creating all these separate lists and, of course, being charged for them.

Chris Garrett: You want to be encouraged to do this. The more you know about your subscribers — the more you know about your customers, especially — the better you can provide the service to them that’s not annoying. It changes how you approach the copy as well, because if you’re sending an email saying, “You may have seen this,” or “I don’t know if you saw this what I’ve talked about last week,” it’s awkward, it’s clumsy. It’s a lot better to say, “You were on the webinar on July the 10th and we’re doing it again.” Being able to say, “I know this about you, therefore I know you will be interested.” Or, “We met at a conference in Denver,” instead of, “Did you see me in Denver?” You’re talking to a person instead of the group as a whole. When you’re talking to a person you get through to them better. You can include the things you know about them.

Brian Clark: Looking at it from a conversion standpoint, if I send out an offer email for a promo and someone clicks but doesn’t buy, that is an important piece of information compared to someone who either didn’t open the email or opened the email and didn’t bother to click. The first person is probably seriously thinking about it. They at least went to check it out.

That’s a very different message that I would send to that person compared to someone who doesn’t seem to be interested at all. Maybe they didn’t see it. With that person you can say, “Hey, did you see this email? Because you didn’t open it.” The person who saw it, clicked, and looked — that’s valuable information. What if you gave them some incentive to tell you why they didn’t buy? That’s incredible information in return that you would also get from knowing that.

Chris Garrett: Also, the majority of the people aren’t going to buy — 95% are not going to buy. If you only focus on the 5% who take the action, what about the majority? What about all the others who might be ready later? They might, as you say, have good reasons why they didn’t take action right now. There’s a lot of money and goodwill sat there that you could be just ignoring.

Simple Examples of Smart Marketing Automation Done Right

Jerod Morris: The other thing that’s interesting too, is how much more you can do when your email is fully integrated into the platform. This is what I want to ask you about in regards to Rainmaker, Chris. As I go through and start using some of these features, I’m finding so many more options available for tagging and segmentation and being able to adapt the content based on what people do on the website. If you’re just using a third-party email provider, you can obviously do a lot based on what they click in the email and all of that stuff, but actually having it integrated into the platform gives you a whole world of other information that you can use to tailor the experience that you’re giving them.

Chris Garrett: Yeah. One of the things that I know you and Brian have talked about a lot is the free member library concept or the free course. We’ve really focused on making that as useful and valuable as possible. Because, if you’re sending people off of your site to a third-party training platform or video hosting platform, you’re losing a lot of opportunity to know about what is really engaging to them — what is really exciting for them, or gets them to take action — or what they want to go deeper into. Having just that website and that training platform in one, that’s huge increase in what you know about your customers or your prospects.

If you look at how we use it — we know if somebody has started Brian’s course versus started the funnel course or Chris Lema’s course. We know if they’re a paid person or a free person. We have a free library because we do what we teach. We know to not send people information based on whether they are free or paid.

We don’t want to send them the stuff that you should pay for, but also we don’t send them things that will annoy them. We don’t tell them to buy what they’ve already purchased, which sounds basic, but how many times would you signed up for something where they should know but they still tell you irrelevant things or they still mistake you for being a prospect when you’re already a customer? If you just go around the web and you see all the remarketing ads for stuff that you’ve already purchased, you know what I’m talking about.

Then, as we add to the platform, we want to look at people who haven’t registered. Maybe they haven’t even signed up for your email yet, but we still want to know information about them to use later. Think about if you’ve got a blog and that blog has call to actions to get people to sign up for the email list or sign up for the free membership, then that free membership gets people to pay. If you’re sending people to separate sites or separate tools all along the line, you’re losing those connections. Once somebody has shown that they’re a human being and a return visitor we want to build up information about them. Then you can start segmenting through your content and through your own site experience. You can have on-site call to actions based on the actions they’ve taken and the interest they’ve shown.

You can have blog post series that lead people to have a deeper interest in a topic and then you can give them the opportunity to go deeper into that by registering for a free course — either as an email course or as a learning management system video-based course with downloads. That’s another opportunity for them to express more interest and show more action. Sign up for webinars — you know if they’ve signed up for the webinar, but did they attend the webinar? That’s all information you can build about them, and it’s all through their actions and their interest rather than trying to infer, spy, or use analytics, which is not really great for drilling down to an individual.

How We’re Building RainMail to Integrate All of These Features Under One Roof With the Rainmaker Platform

Brian Clark: Tagging is an email concept, obviously, but it’s also a CRM concept. You’re actually building a database of informed information. You can review that information, but Rainmaker does most of the heavy lifting for you. I think that the really exciting thing that we’re going to be able to move toward that third-party automation solutions can’t is — because you’re essentially controlling the email list and the site in an integrated fashion, that allows you to truly adapt the site — literally change elements of the page based on topical interest, behavior, and identity. To where, if a certain interest is determined…

For example, we sell a lot of different things, but if someone comes in at Copyblogger through the email marketing landing page, that sends them into My Copyblogger along with everyone else. That’s valuable information, because we know that their point of entry was email. Therefore, the follow-up sequence for that person is different from everyone else, even though they all ended up in the same place based on a tag that is placed right there.

Chris Garrett: If you think about the things we sell on StudioPress, if somebody buys the foodie theme versus the real estate theme that’s good information for us to know. They’re actually expressing that they’ve got an interest in industry in a vertical, and that is really useful information.

We’ve got people in our customer base who are writers, we’ve got developers. They have different needs. They have a lot of overlapping interest, but they also have different interests as well. You can service them better the more you know about them and know what they might be interested in. Also, if you give them an opportunity to express interest and they don’t take the opportunity, that’s also information that you can glean as well.

Brian Clark: Let me ask you this, Chris. You and Nick, one of our developers, were geeking out. We’re trying to extract reasonable deadlines from you — like marketers do — without much luck. Tagging is really the smarter way to segment. But you guys were talking about advanced segmentation and some other stuff that we have coming later in the summer for Rainmaker. Tell us a little bit about that.

Chris Garrett: One of the problems with tagging is that a lot of the time a tag will be a “yes” or a “no.” It’s really interesting to say Jerod is interested in basketball, “yes.” But I think it’s more interesting to be able to say Brian started this course on June 22nd and show a different message if somebody started before June the 1st or after June the 1st. Then there’s things like lead scoring. If somebody downloads a white paper, do you give them ten extra points to say that they are really interested versus somebody who’s got a lead score of one? Is that person now a lead score of 20?

What Lead Scoring Is, and Why It Matters?

Brian Clark: Lead scoring — just so we don’t lose anyone here — this is a way of giving a rating or a numerical value, if you will, to a prospect in which case, if they are more highly motivated than someone else, you might send them an offer or a different message than you would send everyone else.

Chris Garrett: Yeah, exactly. Or you would use that to develop correlations between the activity you’re doing and the quality of the prospects and leads that you’re generating. You might want to know: Did the Google Hangout do better than the white paper? Did the webinar serve you better than the email autoresponder sequence? What is generating the best lead for the money and the investment you make?

Brian Clark: Where did they come from? I guess.

Chris Garrett: Yeah, is a search prospect better than a Facebook advertisement prospect? It might not be just down to picking up the phone and calling your best prospects. It might be, “Okay, this is where our investment is going and this is how it’s paying off.” Down to — once they become a customer — did it take them a long time to become a customer? Did it cost you a lot of money to make them into a customer? This is all valuable information that allows you to tune and tweak things. It’s not just about, “Yes, we can show different messages on screen. We can show different email copy.” It’s also where you’re putting your efforts. It’s the 80/20 rule, 20% is going to be 80% of your payoff.

The Difficulty of Using Website, Email Marketing, and Automation Solutions That Aren’t Integrated

Jerod Morris: Chris, how would someone even try and do something like this with a mishmash of a bunch of third-party providers? As we’ve talked about them, that’s with Rainmaker and it being all integrated. That’s what I was hinting at earlier when I said the one huge key difference — it is that integration having everything in one. How would someone even do this at this level of sophistication when they’re putting parts and pieces together?

Chris Garrett: We tried. We tried to piece all these things together. It didn’t work so well. That’s why we built what we built — we built it for us. If you sign up for a Rainmaker trial or if you sign up for the Digital Commerce, you can actually see us using the stuff we’ve started building. Obviously it’s all going to roll out to everybody who’s our customer on Rainmaker.

We couldn’t really do this integrated thing. We were spending a lot of money and time in development to glue all these things together, and we just thought it would actually save us time and effort to build what we needed instead. The multi-device world we live in — take that alone — where you take a lot of actions on your phone and then you go to the website on your desktop, because bigger screen. You’re ready to use your credit card and it forgets everything about you.

That’s what we want to get away from. We want people to sign up for your free course on the phone being able to follow it on their iPad and then download the PDFs on the desktop and it all be the same person, the same experience, or an enhanced experience. We want you to tell us by viewing the video past 30% that you’re interested. We don’t want to glue all these different tools together. It needs to tell your email subscriber, your member record. It needs to tell your on-screen experience. It needs to tell your experience six weeks down the line that you showed an interest. It shouldn’t forget about you. You can, if you’ve got a big team and a lot of effort, get some of that by gluing a lot of things together. But not what we needed and not to the level we want to take it.

Brian Clark: There’s a ton of businesses out there these days who are essentially one person. They do very well. Of course they have virtual staff and freelancers and designers that are part of the eco system, but you need your technology to be your business partner not a liability.

Jerod Morris: Yeah.

Chris Garrett: How many businesses have got the resources or even the time and bandwidth to have a team of people looking after this? Every extra team member you add — even if it’s a freelancer — is taking mind share away from you as a CEO.

Brian Clark: If your automation solution requires you to hire a consultant, you’re doing it wrong.

Jerod Morris: Yes.

Chris Garrett: Outside of this company. I don’t want to do myself out of the job. The funny thing is how many of these tools are sold as being easy, but really they’re consultant-ware. That’s one thing to be really nervous about. If you have to take a great deal of expensive training and then you have to have a lot of resources to manage the thing, and then you’re so tied in because of all that investment that you’re worried that you’ll never be able to go anywhere else, then you’re not doing your job. You’re not marketing or producing products, you’re not doing customer service. You’re dedicating all that resource and that energy to a tool. The tool should serve you, not you it.

Jerod Morris: Chris, did I hear you correctly? You mentioned earlier — we’ve talked a lot about the importance of the logged in experience and what you can do from a marketing automation perspective when people are logged in. The importance of that will never dissipate. But did I hear you that folks will be able to perform some of those marketing automation functions even when people aren’t logged in?

Chris Garrett: Yeah, I think that’s important for us as a step that we need to work towards as much as possible. Like you say, the logged in experience is going to be the ultimate because we know if they hit that Facebook log in button or that Facebook registration button, we’ve got a lot of information about them and then everything they do. Not everybody’s going to log in and not everybody’s ready to log in. A blog creator doesn’t need to be logged in. Reading an article — we want to know that they are really interested in the 3D printing category versus the basketball category without them having to log in. Then, clicking links — you don’t have to necessarily log in to show an interest, because you’ve clicked the link. All of that needs to be, if they logged in, great, if they are not logged in, to still work.

Jerod Morris: I think you and I need to create a site where it’s possible for someone to take a path of either 3D printing or basketball.

Chris Garrett: Nick and I were actually talking about using these tagging and segmentation rules features to do Choose Your Own Adventure. Do you remember those books?

Jerod Morris: Yeah.

Chris Garrett: We’re actually seriously considering making Choose Your Own Adventure using these tools. I think that will be fun.

Jerod Morris: That would be fun.

Chris Garrett: Ten plus points minus five heath. That kind of thing.

Jerod Morris: All right, can we nail you down on dates when all these stuff is going to be done?

Chris Garrett: No, you cannot.

Brian Clark: We do have one date that we’re fairly …

Chris Garrett: Yeah, we really want to get this into your hands as soon as possible, but at the same time we want it to be great. I really hate promising. But in July we definitely want you to be able to tag people and to be able to show or hide based on those tags.

Brian Clark: Tagging really is the next killer app of the killer app. It’s not necessarily new, but most of the solutions out there that offer this, like I mentioned earlier, it’s an upsell. Remember when we tried out Marketo and they finally figured out that we don’t have a sales team and their solution wouldn’t work for us? We paid a lot of money for that. Of course, that was the moment when we decided to build it ourselves.

The integration in Rainmaker is interesting because it’s a total platform. We don’t have to maximize profit on email. Not only do we not upcharge you for tagging, you’ll see that our email prices — despite world-class servers and deliverability — are cheaper than everyone else out there. That’s simply because it’s all part of one solution. You got all these companies that are SaaS companies that are basically a feature. Rainmaker is the exact opposite philosophy of that.

Chris Garrett: A lot of these systems as well, they don’t understand that one company can have multiple brands. But back to the start of Copyblogger when you started Teaching Sells with Tony, Brian, you had Copyblogger and you had Teaching Sells. A lot of these companies don’t understand that concept that you might want to email from Teaching Sells as Teaching Sells even though the company is Copyblogger. With our solution, your subscribers are your subscribers. It doesn’t matter what websites you have, you can brand it from those different sites. You have the advantage of it being one subscriber going across two brands, but you can also email from that brand.

Showrunner can email somebody. StudioPress can email somebody. We could actually charge extra for that, but it would sound silly to me. It sounds like something that would be obvious for you to be able to do. A lot of those system are set up for, as you say, the sales person to lead them from being a prospect to a “yes” or a “no” and then dismissing them and discard them. We’ve got people going back to 2007 that are still loyal customers. Why would we do that?

Jerod Morris: Yeah, it’s all very exciting. Obviously, Brian and I love seeing these new features and getting to play with them, and we love the ability to share them with you as well. We’d love for you all to go to Rainmakerplatform.com and take a test drive. What was the Rainmaker email service is now RainMail. It is fully integrated in the platform. You can take a free trial of the platform if you go to Rainmakerplatform.com. We’ve also added a monthly billing option now that you can take advantage of. Get in there, test it out, try it out. We got Chris to go about as far as he will go in terms of a promise by letting you know that there will be some new features in July.

Really, there are going to be new features rolled out in July and August and September, because we’re constantly updating the platform with new features and with new updates to be able to do all of the things that we talked about in this episode today. Make sure that you go to Rainmakerplatform.com, get your free trial started, and see how this can take your marketing and your business to the next level. Because the features are great and they will be able to do that. Chris, thank you for your insight. It’s always appreciated.

Chris Garrett: I had so much fun. I don’t want to overpromise, but I’m sure it’s fine.

Jerod Morris: Brian, thank you as well. Always great to have you back on the show.

Brian Clark: I’m pretty sure he hasn’t overpromised.

Chris Garrett: You’ll make sure of it.

Jerod Morris: All right, everybody. We will talk to you next week on another brand-new episode of the Digital Entrepreneur.

The Transcript

3 Simple Hacks for Better Copy and More Conversions in Less Time

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. This is episode number 20 of The Digital Entrepreneur. Today I am joined by Joanna Wiebe, the conversion copywriter for Copy Hackers, where they promise to help you write more persuasive, believable, and usable copy sans pixie dust, so you can boost your website e-mail conversion rates. I’ve had the good pleasure of working with Joanna, so we can certainly vouch for their work. They do a great job.

Something else that I learned recently about Joanna — I actually learned this earlier today — is that she likes making up new words, like indeedly for instance, and using them casually in conversation. I too share in this wonderific pastime, which may be why she and I get along so well. Joanna, welcome to The Digital Entrepreneur, it is great to have you here with us.

Joanna Wiebe: It’s wonderific to be here.

Jerod Morris: Yes, indeedly.

Joanna Wiebe: Indeedly.

Jerod Morris: Joanna’s appearance today continues our series here on The Digital Entrepreneur, where we’ve been talking with some of our esteemed speakers who will be at Digital Commerce Summit, which is coming up this October. Joanna’s going to be a featured speaker, and her session is going to be titled, “How to Make Good Copy Great When Selling Digital.” In this session, she’s going to be discussing real-life examples from actual projects that Copy Hackers has been working on with companies like Buffer, Wistia, and our very own Rainmaker Platform.

On today’s episode, we’re going to explore a few of those projects, some of those ideas here today. But make sure that you come to Denver so that you can hear Joanna and all of our other terrific speakers live. Early bird tickets are still available, so you’re definitely not too late. Joanna’s going to be there. I will be speaking. And, of course, members of the Rainmaker Digital team like Brian Clark and Sonia Simone will be speaking as well, along with a host of our friends from around the digital entrepreneurship space, including Rand Fishkin, Jeff Walker, Tara Gentile, Joanna Penn, Chris Lema, and many, many more.

As we say right there on the website — in the kind of conversion copy that we hope would make Joanna proud — this is the conference and networking event where you will discover smarter ways to create and sell profitable digital products and services. So don’t miss it. For more information, go to Rainmaker.FM/summit. That’s Rainmaker.FM/summit. Again, early bird tickets are still available for now.

Joanna, let’s dive in here, and I would like to kick this off with an admission that I need to make to you.

Joanna Wiebe: Uh-oh.

Jerod Morris: No, it’s okay, and it has nothing to do with the admission that we just talked about before we went …

Joanna Wiebe: Let’s not talk about that.

Jerod Morris: No, you will not. You spoke at the first Authority conference, which was now more than two years from the day that we’re recording this.

Joanna Wiebe: Right.

Jerod Morris: In your presentation at Authority, you spoke about improving our call to action buttons, and you discussed the two elements that prevent people from clicking on buttons, that is friction and fear. To this day, that is one of the lessons from that conference that has stuck with me. Every time I have a call to action button I’m always thinking, “Okay, how do I reduce friction and/or fear to make this as easy to click on for as many people as possible?”

I’m sure the alliteration had something to do with it. You also talked a lot about the lizard brain and engaging the lizard brain. I think just because this little easy framework — friction and fear — it works. So thank you for that lesson. It’s another reason why going to conferences is such a great thing to do. In addition to the networking, you can pick up these little nuggets that really carry through. Maybe everybody will have different ones, but I’m very appreciative of that one.

Joanna Wiebe: Oh, that’s cool. I’m glad you remember that. That’s awesome to hear. That was a really fun conference.

Jerod Morris: Yeah, it was, and this one will be good too. To start, just give us a little background, if you would.

Joanna Wiebe: Sure.

Jerod Morris: Can you explain a little bit more about what you and the Copy Hackers team does?

Joanna Wiebe: Yeah, absolutely. We get to work with some pretty cool companies — present company included — where we optimize copy, essentially, or we aim to, at least. Sometimes it works, other times it doesn’t. That’s the nature, and that’s why we test. We help organizations either write better copy, or copy that’s worth testing and measuring, or we teach them how to do it. Our blog teaches you how to do it. Our courses teach you how to do it. And if you really want to see how we work and to have us go in and help you hands-on, then we sometimes accept clients. Only the coolest clients, obviously. Just kidding. No, we’re really lucky to work with very cool people that we love, so that’s wicked.

That’s what we do, and the biggest thing that we focus on — outside of being really dedicated to copywriting and messaging — is testing. To be sure that we at least know if something’s working or not. Then we can hopefully have a good hypothesis so we know why it didn’t work or why it did work, so we’re not just constantly guessing and then guessing at something else and then something else. Yeah, that’s what we do.

Jerod Morris: Yeah, that’s the thing that’s been so clear in working with you guys, is the culture of testing that you have and the commitment to testing. Do you find with individuals that you work with, with companies that you end up working with, that the people aren’t testing enough or that there isn’t enough of a commitment to it?

Joanna Wiebe: Yeah. I think it’s a scary thing for a lot of people. It depends where you’re at when you’ve heard of it, but testing feels like … If you’ve just heard of it, it sounds exciting. And then you go and you look into it, and you’re like, “Oh man, I need so much traffic to test a page. And then I need to have a big enough change in the conversion rate to close a test. Wow, I need so much, it’s just going to be too hard.” But you try doing one test, you don’t get any conclusive results, and you just throw your hands up and say, “Testing doesn’t work for me.”

Then there’s the other end where it’s like, “Okay, we don’t test, we only engage in marketing automation, behavioral automation, behavioral marketing, and personalization as a subset of that. So if we A/B test, it’s within this really complex system of marketing automation, essentially.” Those are the bigger businesses that look at A/B testing as trying to find a single solution for a whole bunch of people, which we all know isn’t possible in most cases — to find a single solution or way to message something that works for everybody visiting that page or reading that e-mail.

At the other end of the spectrum, people discount it as trying to do too much with too little, and at the first side of it, the newer people coming into testing, it just feels like you need too much traffic to make it work. Naturally people shy away from it, and I certainly don’t blame them for it. When you get into testing there’s a lot to consider. Where the sources of traffic are, should you be including mobile traffic in your test? If not, should you be doing a separate test just for mobile traffic? There’s so much to think about that I think it can be a bit off-putting for people.

When it comes down to it though, A/B testing is really just, “Here’s the page that we’re currently working with. Here’s what we think we might want to replace that page with because we feel — based on a lot of different data points — that this is the stronger message to go with, but we don’t know. So we’re going to A/B test it one page versus the other.” That’s really, at its core, all it really has to be about. But it’s easy to over-complicate that.

Simple A/B Test Anyone Can Use to Gain Valuable Insight Into Audience Behavior

Jerod Morris: For someone who’s listening to this, maybe they’ve thought about testing but they haven’t done it yet, or maybe they have but it’s been kind of complicated and it feels real convoluted for them. Do you have any suggestions for a simple test folks can go out the door with? Maybe dip their toes in the water? Maybe it’s changing just a headline on the homepage or changing a button. Is there a universal first step people can take to start wading into the testing waters if they haven’t yet?

Joanna Wiebe: Yeah, and it’s basically those two things you just talked about, actually. There’s two ways that I recommend if you haven’t done a test before. The first one is to do an A/B test on your highest traffic page, generally. Generally on your highest traffic page, where that new variation you come up with has a new headline and a new button. Not one or the other, but both changed on variation B. That’s because that button is the real site of conversion. It’s where the measuring happens, on the button.

If you only change the headline but the button isn’t improved, then it complicates things a little bit, or it means you’re going to have to really swing for the fences with that headline, or be dramatically different. I recommend if you’re just starting out do a headline plus button test where that becomes your new variation. Another really easy way to start testing is to test the placement of that button or call to action. If you currently have it in your homepage hero section — where basically every digital business on the planet has a button, in that hero space — try moving it.

Now, obviously, any CRO person will absolutely say, “Well, you have to have a reason why.” We can get into that at some other point, but if we’re just talking about, “Here, test it,” just to get into testing, just to dip your toes in the water, then just test removing that from the hero and moving it further down the page. See what happens. Or test it as a sticky button that follows you as you go. Buttons are the absolute easiest test to start with.

Jerod Morris: But don’t move it so much that there’s increased friction.

The Surprising Button Placement That Actually Worked Wonders for One Company

Joanna Wiebe: The question when we’re like, “Okay, where does a button go?” is at what point is our prospect — our one reader, the one we’re actually trying to convert — at what point are they ready to move forward? You put a button in front of people, they will click it. People like to click the button. That’s the lizard brain, right? “Ooh, I see it, I just – Ta-da! I click it! I didn’t even really look at the things that I need to look at yet.”

We actually did a test on Sweatblock.com, which is an e-commerce site. It’s a little bit different. But we tested a variation of the homepage, kind of a one-pager. Our variation B moved the button way down. The control had the button in the hero section. Variation B opened with a problem agitation solution opening, which is kind of odd on homepages.

You usually just lead with the solution on a homepage and then you might try to back up and go into problem agitation solution as a framework. But we were like, “Nope, we’re not going to lead with the solution. We’re not going to put that button in the hero section. We’re going to lead with the problem. No button. We’re going to agitate the problem, still no button. We’re going to talk about the solution, and only when we’ve said enough about the solution will we put the button on the page.”

I actually just wrote about this on the site. We saw 45% more paid conversion when we did that. More products purchased — not just clicks, but products purchased — when we moved that button down and made people feel something first. The question is, where do you need to put the button? It obviously depends on where your prospect is at, but I would say be sure to be confident in your ability to move people to click, but don’t let them click whenever they feel like clicking. That’s part of having that button test.

Jerod Morris: Wow. That’s great stuff, right there.

Joanna Wiebe: It was fun.

Jerod Morris: Yeah, I bet it was. As I mentioned before, your session title is going to be “How to Make Good Copy Great When Selling Digital.” I want to talk a little bit about what that means, making good copy great. But not just for any reason, for any type of copywriting, but specifically when it comes to selling digital goods. Are there specific elements — and I think you just hinted at some right there — but are there specific elements to writing great copy for selling digital goods that may be different from other types of copywriting?

Why Copywriting Fundamentals like the Rule of 1 Still Work

Joanna Wiebe: I have found that selling digital goods has more to do with traditional direct response copywriting than not. Using the old tried-and-true rules that we read about from Shorts and Caples and all those awesome dudes — those still work. Those still completely and totally work. It’s when we pretend that the rules have changed that we harm our conversion rates.

There’s this sense that people buying online or people reading online are these completely different thinking beings that don’t follow any of the old rules and can’t be persuaded the old ways so we’re going to just throw stuff at them. They like to look around so let them look around. But we haven’t found that that’s been anywhere near as successful as controlling the flow of information.

That comes out in different ways. Sometimes it will mean we take a long-form sales approach and we put it into a “palatable” form on the page so it doesn’t look like a long-form sales page. It still acts like those old sales letters, it just doesn’t look like a letter. When it comes down to it, it’s really about those formulas and frameworks and just listening to your prospect and repeating what you heard on the page. That goes a long way. You think back to Great Leads and books like that, where they talk about basically what I’ve summed up. I don’t even know if it was from the book, I read it so long ago.

The rule of one, where you’ve got one reader, one offer, one big idea, and one promise. If you still follow those when selling on a landing page — it’s hard to do that on a homepage because you generally don’t have one reader, but that’s a big discussion unto itself — if you follow those parts and organize your page with that in mind, you can still see great conversion lift. We did something similar with Buffer, which I’ll be talking about at the summit so I don’t want to talk too much about it. Come to the summit if you want to hear the story.

We followed some of that like, “Okay, what do we need to say to the prospect to move them from the stage of awareness they’re at to the stage of awareness we need them to be at on the page in order to move forward to the point of being a paying customer for Buffer? For their business plan?” We did some cool stuff, we saw very cool lift, and that’s all I’m going to say about it because we’re talking about it at the summit.

What the “Stages of Awareness” Are and Why They Matter

Jerod Morris: You mentioned the stage of awareness. How do you know what stage of awareness folks are at on different pages and in different parts of the process?

Joanna Wiebe: Yeah, totally. Generally a good thing is to look at where they were before, and that should indicate in many cases — maybe not all cases, but we’re looking for as much solid info as we can use. Sometimes it’s imperfect, but oftentimes it’s better than nothing. We look at where they were first. That could mean, “What keyword phrase did they use? Or where were they? Was it a Facebook ad that brought them to us? Are they already on our list or are they not on our list? Are they a returning visitor or are they not a returning visitor?”

Those sorts of things can help us say, “Okay, if they searched a branded keyword phrase like ‘Buffer for business,’ or ‘Buffer for business pricing,’ chances are good they’re in product to most aware.” Those are the two places we’d want to put them, so where do we then kick off the page, that landing page for them? Well, we’ll want to mention the product if they’re in product aware. We might also mention it if they’re in most aware, although what the page looks like will probably be different for those two.

A most aware person — it always depends, but a most aware visitor landing on a landing page meant for most aware visitors is probably going to see a shorter page that does more of the things that we see in Cialdini’s Influence. All of those sorts of persuasion techniques that are great for the lowest hanging fruit, like a lot of social proof, urgency — maybe scarcity, if you’ve got it. Those sorts of things that we hear about as persuasive but that might not work as well for somebody who’s solution aware. But for product aware or most aware they could work much better.

Now, product aware — we might find ourselves putting a lot more on the page to get them to the place where they’re ready by the end of the page to pay. I don’t know, is that clear? I feel like I could talk for an eternity about stages of awareness.

Jerod Morris: No, it is. I think it’s important. It’s funny, because I think we got into this on the call that we had earlier today too. You can have this great piece of copy and it feels really well written and it feels good, but you can’t really tell how successful or good a piece of copy is outside of the context. You’ve got to understand when the person who is the target of this copy, the audience, when are they getting it? What do they know? What have they done already? Where are we trying to get them to go?

I think you don’t want to over-complicate it, because I think the fundamentals of copy are pretty simple. But you also don’t want to underestimate the importance of really understanding the context and putting that copy into the right context for the audience member so that they can actually take the next step that you want them to take.

Joanna Wiebe: Yeah, exactly. This is something that any UX person would absolutely agree with, that context is huge. Even as you’re talking, I’m thinking of how these disciplines all come together today and how it’s helping us all, I think, to produce better materials that are — all of these same principles keep coming up. Like you say, where’s the context? Where are they actually at in experiencing our brand or our product?

If you don’t think about that — this is why targeted landing pages are so important. They’re so easy to create today, as well, that it’s shocking when people don’t. If you write and you send everybody to one or two landing pages that are somewhat generic, they’re just never going to work as well. Or you send e-mails that aren’t specific to what a person’s really going through, they’re just not going to work as well. We all know that.

But sadly — and I know why it is, I go through this for business too — it’s like, “Okay, well I have to prioritize what I’m going to do,” and doing something else generally looks better than sitting there and saying, “Okay, well we have to write six different drip campaigns for six different triggers. It’s going to be a 10-week job to get to the point, and we’re going to have one person on it full time.” You’re like, “Holy crap, well what if they don’t work?” Yeah, it’s true. If you don’t know the context or you don’t know where the prospect is at when they’re looking at the page, none of us should be terribly surprised when they don’t convert as well.

The Difference Between What You Care About and What Your Prospect Cares About

Jerod Morris: Do you think that that’s one of the biggest mistakes that you see individuals and companies make when it comes to their copy? What might be some other ones?

Joanna Wiebe: Yeah, it’s a biggie. It’s not knowing the reader you’re talking to so you put down on the page what you think. I hear this a lot, even in our comments on our blog. I’m sure you’ve seen the same for Copyblogger when you’re talking about copy. We had a bunch of comments recently on one of our posts where we asked people to comment on what they would differently with the copy. One thing that kept coming out was, “I would need to see this,” or, “I wonder about this.” The person is thinking that because they care about it, the prospect cares about it.

Obviously as we’re talking about it, everybody listening is like, “Well, of course not.” But how often do we actually sit there and do that? Write a page where we’re like, “Oh, okay, well let me imagine what you want to know in order to move from where you are to where we want you to be. I think you might care about this, so I’m going to make this the headline.” That’s, I think, the biggest problem, and it happens again and again. Imagining that you could possibly know what your prospect wants, or that your prospects wants the same things you want in the order you want them. For me, that’s an ongoing, continual problem.

Jerod Morris: How do you get around that? To start, you have to have some kind of hypothesis. Is it then just refining based on data and what you see? How do you approach that?

Joanna Wiebe: Start with lots of data. I know that that can be problematic for people who say, “Okay, that’s our business before. Data reflects the business as it’s been and the users we’ve had, not who we want.” If you let that be your reason not to use research or data, then I don’t know. I’m sure other people will know how to help you — hire somebody who does. I don’t know. What I know is that if we look at the data — like the analytics, like click-tracking on the site — if we ask questions about the landing page that identifies who you are …

Help me understand. Put a Hotjar poll on the page you want to optimize and ask questions, or a question, to help you figure out where that prospect is at so you can write for them. Then put click-tracking on there to see where they’re not paying attention. Then consult your actual survey responses that you might have that are from a larger survey that you’ve done, where you can split your data up. Do those sorts of things and you’ll be more likely to write a page.

But that’s how you find what you ought to write about. We all know it’s not sitting there, staring at the page, thinking, “Hmm, what do I care about? To optimize this page, what do I want to know differently? What’s not on here that I need to see?” We all know that’s not the way to do it. Usertesting.com — you can send people on and actually pinpoint. I know it doesn’t get that granular, but you can get down to marketing managers and have only marketing managers — let’s say if you wanted to sell a product to marketing managers — have marketing managers on usertesting.com spend 20 minutes. Get 5 of them to spend 20 minutes on your page answering questions, and that alone will illuminate some opportunities for you and some of the things that your prospect might actually care about.

How to Listen in a Way That Actually Leads to Meaningful Results

Jerod Morris: Yeah. As we were working with you, that was one of the things that you guys did early on and wanted to even do more, was talk to actual customers.

Joanna Wiebe: Yes.

Jerod Morris: How important is that?

Joanna Wiebe: It’s everything.

Jerod Morris: Yeah?

Joanna Wiebe: For me, it’s everything. Interviews alone. There’s all sort of stuff that you can go out and do. We talk about this all over the place. I could make a list, and probably just will. Interviews are hands-down — they’re the thing you want to do least, and they’re always the most revealing if you can get somebody to sit there and talk with you on the phone or in person for an hour, and listen like a crazy person. Just listen the whole time and then transcribe what you’ve heard. Yeah, for me — and I know others will say they don’t do it this way and it works for them to do it their way. Cool. All I can speak about is for me. And for me, time and again, I get the best results when I just shut up and listen and then repeat what I heard.

Jerod Morris: I think that’s true for most folks. It’s so important, and it is underrated.

Joanna Wiebe: Yeah.

Jerod Morris: It’s interesting. What would be your biggest general piece of copywriting advice for folks? I feel like what you just mentioned, listen — the irony of that being the biggest skill that you can have as a copywriter, someone who is producing content, is to actually listen … Maybe that is the best piece of advice. But what is your best general piece of advice for folks to take their copywriting to the next step, to get a little bit better today the next time they write some copy than they were before they listened to this episode?

The Oft-Overlooked Importance of Frameworks and Formulas

Joanna Wiebe: Yeah, I would say listening, doing that research, that’s huge. In one hand: research. In the other hand: frameworks and formulas. I took a long time to come around to the idea of not basically starting from scratch, or of letting somebody else tell me how to frame the page or how to organize a headline. I think a lot of us as copywriters — you still identify heavily with the writer side of that, which is nice and great. But I recommend you have something else you’re writing on the side as a creative project and then make copywriting about copy writing. That means take frameworks and formulas and use those.

This is the hardest thing for people to get their head around. Even when they start listening, they’re like, “Oh, cool. I got all these survey responses. There were these long answers, and look at this sticky copy in there, awesome!” They go and start using it on the page, but they use it without any formulas, without any frameworks, without any way to say this is the right way to organize it. And that’s a problem as well. Don’t try to dream it up from scratch in any way, shape, or form. Listen, and then take what you have heard, and use frameworks like PAS, which I mentioned already and which happens to be my favorite for organizing any message or writing anything. PAS comes through for me every single time.

Jerod Morris: Which is problem, agitate, solve?

Joanna Wiebe: Yes, exactly. Sorry. Headline formulas, crosshead formulas, and button formulas. Just use them. I know it feels like, “Ugh, it’s not as fun,” but you know what’s super fun about it? You get to see cool results. For me as a copywriter, that’s where the real fun is, when a client’s like, “Holy crap, you actually brought in twice the number of paid conversions, that’s amazing.” That’s going to feel better than saying, “Oh, those are my words on the page, organized as I think they ought to be.”

Those are the two things. Research in one hand, frameworks and formulas in the other. Put your hands together.

Jerod Morris: Yes, and it simplifies it. Maybe it makes it less art in your own mind, but it simplifies it and you can be more efficient and get better results.

Joanna Wiebe: Yeah, absolutely.

Jerod Morris: It all makes sense.

Joanna Wiebe: I find that, at least.

Jerod Morris: Yes. Excellent. Joanna, this was great. I can’t wait to hear your presentation at Digital Commerce Summit and see what great nugget you say that I’m still thinking about and talking about on podcasts two or three years later.

Joanna Wiebe: Sweet, and I can’t wait to reveal your giant secret.

Jerod Morris: Cut. Yes, it’ll be great. We hope that you will join us at Digital Commerce Summit. Go to Rainmaker.FM/summit. The dates are October 13th through the 14th. We will be in beautiful Denver, Colorado. As I said, on the date that this episode goes live, early bird tickets are still going to be available. I don’t know how much longer they will be, but they are still right now, so go to Rainmaker.FM/summit. Get your ticket and join us in Denver. We can’t wait to see you. Joanna, I will see you there.

Joanna Wiebe: Yeah, thanks a ton, Jerod.

Jerod Morris: Absolutely. We will see you all there and on next week’s brand new episode of The Digital Entrepreneur. Have a great week.

The Transcript

Practical Advice on Turning the Challenges of Building Membership Communities Into Opportunities

Voiceover: You are 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.

Jerod Morris: Welcome back to The Digital Entrepreneur. This is episode No. 19 of The Digital Entrepreneur. I am your host, Jerod Morris, the VP of marketing for Rainmaker Digital. Today, I am joined by a colleague of mine here at Rainmaker Digital, Pamela Wilson, our esteemed executive vice president of educational content.

There are a couple of reasons why I asked Pamela to join us this week and why I’m so excited that she said yes. Here are those reasons. One is that Pamela’s leading our Authority educational content at Rainmaker Digital, and she has spearheaded some initiatives to grow it and make it better. I have some questions I want to ask her about those initiatives.

Number two, Pamela’s going to be a featured speaker at Digital Commerce Summit, which is coming up this October in Denver, Colorado. Her session will be titled How to Cultivate a Profitable, Interactive Member Site.

In addition to what she’s been doing with Authority, I want to get some of Pamela’s general ideas on what it takes to build a membership site that provides value and drives profits because I know that many of you are working toward that goal right now.

By the way, if you don’t have your ticket yet to Digital Commerce Summit, I do hope that you’ll consider joining us in the Rockies this fall. Early bird tickets are still available, so you’re definitely not too late. Don’t worry about that. You’re not too late. You can still get a great price on a ticket.

Pamela’s going to be speaking, as I said. I will be speaking there, and of course, Brian Clark and Sonia Simone will be speaking as well. They’ve been guests on the last two episodes of The Digital Entrepreneur, along with a host of our friends from around the digital entrepreneurship space, including Rand Fishkin, Jeff Walker, Tara Gentile, Joanna Penn, Chris Lema, and many, many, many more.

This is the conference and networking event where you will discover smarter ways to create and sell profitable digital products and services, so don’t miss it. For more information, go to Rainmaker.FM/Summit. That is Rainmaker.FM/Summit.

With that, I would like to welcome Pamela Wilson to the show. Pamela, thank you again for carving out the time to join us on this week’s episode.

Pamela Wilson: I am so happy to be here, and I love this topic. It’s a fun thing to talk about.

Jerod Morris: It’s a good one, and like I said, you have a lot of experience to talk about this, which is why I’m so excited to have you here as the person to share some experience and share some knowledge with the audience.

Let’s start there. You have really extensive experience in online education, dating back to well before you joined the Rainmaker Digital team. Can you give us just a brief overview of what you were doing prior to joining Rainmaker, which was then at the time Copyblogger, and how that informed the work that you’re doing now?

How Pamela Eventually Turned a Childhood Dream into Reality Thanks to the Internet

Pamela Wilson: Right, so I’m sitting over here trying really hard not to laugh at that introduction because I guess I have extensive experience, but I want to share this with people. This might be something they can relate to a little bit more. I actually always wanted to be a teacher. When I was growing up, I wanted to be a teacher. My grandmother had been a teacher. And I was in FTA in high school, which is Future Teachers of America, so this was my dream.

Jerod Morris: That is not a surprising revelation at all.

Pamela Wilson: Okay, so that’s not surprising, but the interesting thing is, my mother actually discouraged me from becoming a teacher.

Jerod Morris: Really?

Pamela Wilson: Well, she saw that I had always been creative growing up, and she really encouraged me to go into a creative career, which I did. That was my entire career. I worked as a designer and a marketing consultant for decades, really.

After doing that for decades, I started to get antsy. I wanted to do something else, and I started looking into building an online platform and teaching online. I ended up moving into that, so I guess I showed my mom, like, “I showed you, Mom.” I eventually ended up doing the thing that I had dreamed of.

Jerod Morris: You know what’s so interesting about that is you find that a lot when you look around, and you look at successful people. Maybe they’ve been successful in business or something in digital entrepreneurship, but so many people have brought a passion from their childhood and found a way to weave it in there.

It’s like you have found a way to combine your creativity and your business acumen with your ability to teach, which is great. I grew up as a huge IU basketball fan, and now I’ve found a way, with the skills that I’ve learned building membership communities and a podcast, to bring that passion back into it. It’s kind of funny how those things will naturally just start come back. It’s very interesting.

Pamela Wilson: Honestly, I think that’s one of the most beautiful things that the Internet offers us. We really can explore those passions in a place that allows it, and we can find other people that have the same passions. It’s a great way to connect with people who have those same geeky interests that we do. You get to draw from all of humanity. Anyone who is connected to the Internet can find you, so it’s pretty amazing.

I ended up looking into how to do this, and right around the time that I was looking for how to build this online platform, I found Copyblogger. That was like 2009, so it’s not like Copyblogger had been hiding or anything. But I just happened to stumble on Copyblogger at the moment when I needed it.

Just a couple of weeks after I found the site, they were re-opening Teaching Sells, which was the seminal course on how to build online courses. I signed up for that, and so my online teaching story is very much interwoven with Copyblogger’s story and how Copyblogger teaches things.

I learned how to create online courses by taking that course, and then built my Big Brand System site, built a course there to teach basically what I had learned to do in my career, but boiling it down so that people who didn’t have a design background or didn’t have marketing experience could understand it and apply it to their own businesses.

Once I did that, I created all of these smaller products, so I created a product called The Ebook Evolution, which helps people to create ebooks by themselves, PDF e-books mostly, Site Setup Kit, which was to help people who had no web developer background build a website that they could control themselves, and then a product called Visual Buzz 101, which was basically to help non-designers create great-looking images for their web presence.

Jerod Morris: What’s interesting about that, you had this formal training with the Teaching Sells, of developing courses, and then you got into it and went out and did it on your own. I imagine from the experience of Teaching Sells, you had a pretty good roadmap to follow. You knew what to expect, but doing it for the first time with Big Brand System and doing it on your own, what were some of the things that surprised you about the experience?

What Pamela’s First Experience Creating Her Own Membership Community Was Like (and How She Prepared for It)

Pamela Wilson: Honestly, that’s one of the coolest things about being part of this team now is that so much of our effort is focused on making the Rainmaker Platform awesome. The biggest surprise to me was how difficult at that time–this is back in 2010–how difficult it was to put together the technical pieces that I had to put together to create the membership site. I felt like I was scaling Mount Everest. It was seriously way beyond my technical pay grade to put that together, so that was surprising to me.

The course part, I felt like the education in Teaching Sells really helped to guide me so that I could put together education that was useful, effective, and all of that, so that part was great. Then the technical piece was just a nightmare, so it’s very cool to be on the other side of that now and helping to contribute, even in a small way, to this product that just makes all of those things so much easier.

I loved it, though. That whole experience of building a community around something that you’re teaching, I loved that.

Jerod Morris: Speaking of that, let’s talk a little bit about Authority. As a I mentioned earlier, you’ve been leading our Authority membership program. I’ve been a really interested observer, watching you systematically, methodically make improvements over there.

Can you provide an overview of where Authority was when you got involved with it and what you’ve tried to do to take what was working and make it even better?

How Pamela Has Approached the Challenges of Running a Mature Membership Community Like Authority

Pamela Wilson: Right. Sonia and I worked together to come up with this plan. We wanted to inject new energy into this program. It was already a solid program, but it had been around for a while. This is one of the interesting things. A membership site at the very beginning of its life cycle and then after it’s been around for a while, it has a different set of challenges.

Some of it is just making the information easy to consume and making it easier for people to get their way through all the information. After it’s been around for a while, you have a lot of information, and people’s first reaction is, they get in there, and they’re like, “Ah, I don’t know where to start.”

It was that, but it was also encouraging people to consume the information. I was looking for ways that we could involve the community more, and I’ll talk about how we did that. Then I was also looking for ways to just simplify the process, the production process on our end, and make it a little bit more predictable. That’s how I came to this idea that I’m going to be talking about at the summit, which is finding this sweet spot in-between your efforts and your profits.

Jerod Morris: Yeah. You mentioned some of these challenges of an older membership site that’s been around a while. It doesn’t have that new car smell and feel. It’s like anything else. You can look at that, and there are challenges there, but you can also flip it around. You can say, “Okay, but what does this make possible?”

Pamela Wilson: Exactly.

Jerod Morris: There are some challenges, but how did you then overcome those challenges, building upon what was already there?

Pamela Wilson: Right. One of the things was to just encourage community. These are all such small things, but one thing was, in our weekly webinar–we have a webinar, a live webinar, every single Friday–and one thing that I’m doing on a lot of those webinars is I incorporate shout-outs to people who have posted in the forum and might have a question. That just helps people to know what’s going on in their community and maybe drives them into the forum to participate a little bit more. That was one thing.

Another thing is just to develop content that highlights our members, what they’re doing, and what their challenges are because so many people have very similar challenges. I set up this schedule of webinars that we do, and it’s basically the first week of the month is always the same kind of webinar. The second week is something else. The third week is something else, so it’s a very consistent … you know me well enough. I like systems and processes. I’m really into that.

I found it made it more predictable for our members, but it also was easier to create content for the program when I had these predetermined buckets that I had to fill. What we’re doing is, the first week of the month, we have this master class educational session. That is no-holds-barred, pure education. We’ve really put a lot of effort you joined us, actually, you and Loryn Thompson joined us last month, or earlier this month, I guess, for the educational session in June.

That’s usually a very high-level and in-depth educational session. We typically create a downloadable worksheet or some kind of handout so that people can apply what they’re learning to their own businesses.

The second week of the month, we’re calling it our ABC sessions, Authority Business Coaching. We invite people to apply to be on these sessions. Then when they are with us live, we do all sorts of things. We look at their websites. We talk about their marketing efforts. We talk about how they could build an email list. We talk about also what’s working because a lot of people have things that are working really well, so it’s a matter of building on their strengths.

That ends up being almost like a private coaching session that others can watch and benefit from. Because so many of us are dealing with the same kinds of business challenges, people have loved those sessions. We’re so grateful for the people who volunteer to basically put their businesses out there and get coaching live. They seem to benefit from it, but then the people watching benefit as well. Those have been a lot of fun.

Then we have always done a live Q&A session every month, and we’re continuing with those. We like to call those mini coaching sessions because it’s an opportunity for people to ask a question directly of staff members from Rainmaker Digital, who are the people manning those sessions. Sonia and I do a lot of them, but I invite special guests in, too.

Then we do this Behind the Scenes session at the end of the month, which is basically highlighting a member who has had some success in some area. We have all sorts of different members with all sorts of different businesses. They might have a product launch that went really well, and they want to talk about that. Or they did something for their email marketing that just made their list grow like crazy, so they talk about that.

It’s just an opportunity to highlight members who have figured something out, and they want to share it with the rest of the membership. Those have also been popular. Basically, 50 percent of our content is highlighting a member of the community inside Authority, and that has been so much fun. It has really helped me to get to know our membership better, and I think members have enjoyed just getting to know one another’s businesses and learning.

Jerod Morris: Yeah. It creates community. It puts people into a spotlight, which people like. And like you said, with the coaching opportunities, the one-on-ones, that’s a great way to provide really significant, specific, one-on-one value to folks, but also value that others can learn from. Those Q&As, even if you don’t have a question answered, a lot of times it can be really valuable.

We’re not going through all of the things inside of Authority here as a commercial for Authority. It’s really more to let you see some of these options that we’re doing. For anybody who’s listening to this who has their own membership site or is thinking about doing it, these are all ideas that you can incorporate into your own.

Why It’s So Important to Find the Elusive Sweet Spot Between Effort and Income–And How to Know When You’re Out of Balance

Jerod Morris: The challenge, of course, is that it’s not easy to do this, and I’m sure, Pamela, as people heard you talking about doing this every week, and this every week, and this every week, it can sound a little bit like this intimidating machine that just needs to constantly be fed. This is where I want to transition into your talk at Digital Commerce Summit. You’re going to be talking about this.

Obviously, you can’t just spend 24 hours of every single day creating new membership content. That’d be perfect, and you’d create, I guess, more value, but the goal is, for gathering a community around you to teach–and to make money doing so–as you said earlier, is finding that elusive sweet spot between effort and income.

How do we find that sweet spot, and how do you do all of this inside of Authority and still make sure that it is a profitable use on your time that’s getting a good return on the investment?

Pamela Wilson: Right. Again, that’s where approaching this as, rather than something that you have to just keep doing week after week, and month after month, I actually find it very freeing to have created these … I like to call them ‘content buckets.’ I know it’s a very technical term, but it’s content buckets.

You know the first week of the month, you’re not starting from scratch. You know what you need to put together, and the second week of the month, you know what you need to put together. Frankly, some of these sessions require a lot more time and preparation than others. For example, the educational session, I put a lot of time and effort into creating those, and I want to make them really, really high value.

We want them all to be high value, but for example, for a Q&A, all I really have to do is to look through the questions. Sometimes I do some minor research on things I want to recommend to people, but there’s not as much prep time.

Having this schedule and this system in place really helps you to pace yourself as you’re creating content for your membership program. That’s where that sweet spot comes into play. You do have to find this place where the time and the money that you’re pouring into your membership program is balanced by your profit. Profit is earnings after you pay all of your expenses.

You have to make sure that any money that you’re spending to keep your membership program alive is balanced with the effort and the time you’re putting into it. You have to do the equation and make sure it’s all worth it.

Jerod Morris: Obviously, a big part of tracking that is knowing your numbers, literally having those numbers there. Are there any other warning signs that you might be able to shed some light on that maybe hint at the fact that this is a little bit out of balance? Anything that you’ve found, outside of just literally tracking the numbers?

The Potential Impact of Tracking Your Time

Pamela Wilson: Yeah. Honestly, I think people have to be willing to do the hard math of saying, “How much time am I pouring into this? How much am I earning from it, and how much does that end up giving me per hour?” for example.

As content creators, a lot of us get really caught up in the content creation process, and sometimes we don’t step back and say, “How many hours am I actually pouring into this, and how much profit am I actually seeing?” It can be hard to do that because sometimes you don’t like the answer, but it’s always better to know the answer and to just say, “Okay, obviously I need to make some adjustments here, and I’ll just make them.”

As much as possible, I love the idea of trying to systematize your content creation for any kind of a program, membership program, any kind of a teaching product. You want to try to systematize it as much as possible. If you own your own business, you always want to look for things that you could hand over to someone who you don’t have to pay as much as what your time is worth.

Look for an assistant-type person, a virtual assistant. Some people use college students who are trying to get experience, and they pay them a paid internship. They’re able to do some things that are important, but maybe can be taught and passed over to someone else once you give them a process. Like any good business owner, you do have to look for ways to do that, that keep your expenses down, and then free up your time so that you can focus on the more high-level stuff.

Jerod Morris: Do you actually track your time?

Pamela Wilson: I don’t track my time now. I used to, though. When I was running my own business, I did. I would track my own time. When I was working for clients, obviously I would track time for them. I never charged by the hour. I always charged by the project price, but I always tracked my time because I just wanted to see. It’s like, “This is what I estimated this project would take me to do. How long did it actually take?” That made me much more accurate over time when I went to estimate projects, so yeah, I did that as a habit.

Jerod Morris: It’s interesting. I hosted a case study inside of Digital Commerce Academy with Andrea Vahl, someone that you know very well. She was telling the story of these two different campaigns she did because she’s obviously very big on testing, which is a smart thing to do.

She had this campaign in February, this launch campaign, and she was going over these different variables and different results for how many people opted-in, different lead magnets that she had, and all these different things. One of the things that she tracked to see how successful this was, was time. For instance, the first campaign took her 15 hours, and the second campaign took her seven hours, and that was all kind of factored into, “Okay, how successful was this?”

It was kind of eye opening for me because we track lots of different variables, like cost per click and all these other different things, and trying to compare the revenue from one to the revenue of the other. In our heads, we understand that we want this to take a little bit less time, but when you actually put the time there, you see the hours that it took.

I hadn’t thought about doing that, but I’m actually considering starting to do that now for myself, just to track the time and see, “Okay, how much is this really taking me? What am I getting out of this?” I’ve never wanted to do it because it just seems a little bit annoying. Maybe not do it forever, but to do it for six months just to see and get a gauge., I think it really could be useful and helpful.

Pamela Wilson: It’s kind of like people who are dieting, and they keep a food log.

Jerod Morris: Yes!

Pamela Wilson: They log every single bite that goes in their mouths, and sometimes it’s very eye opening. Or you start wearing a Fitbit, and you’re like, “Oh, gosh. Maybe the reason I’m not very in shape is because I’m only walking like 1,700 steps every day.”

Jerod Morris: Yeah. You know the funny thing about that is I’ve lost maybe 11, 12 pounds in the last three months, and a big part of it is because I started tracking my calories. When you can actually see it, it does, it helps you eat less because you’re like, “Whoa, I’ve already had that much today. Okay. Let me back off a little bit at dinner.”

Pamela Wilson: Yeah. It’s like knowledge is power.

Jerod Morris: It really is.

Pamela Wilson: Yeah, and that is an old habit from having owned my own business for many years. One of the things that you realize is you are one person, and you only have 24 hours. You can’t manufacture more time for yourself, so you start to become very efficient at using your time, then taking the things that you have to get done, and finding possibly people who can do them more efficiently so that you can focus on things that other people cannot do. It’s an old habit, but I think it’s a good one.

Jerod Morris: Pamela, for the digital entrepreneur who’s out there right now, who’s listening to this episode, and who is considering going down the road of building an educational membership site–they haven’t yet, but they’re thinking about it–what’s the biggest piece of advice that you would give that person about how to get started?

The Single Biggest Piece of Advice Pamela Would Give to People Thinking About Starting a Membership Community, and Those Already in the Midst of Running One

Pamela Wilson: The biggest thing when you’re starting out a membership site is there is this feeling like, “Okay, I’m getting on this hamster wheel, and I can’t ever get off. I just have to keep creating content for my membership program.” Depending on how you structure it, it might be a membership program that doesn’t have ongoing content, but either way, there is this feeling like you have a tremendous amount of work ahead of you.

I would say anything that you can do to simplify your processes and set up systems from the very beginning, you will be very happy to have those things in place. Just look at all of the tasks you have going on, and see if there are things where you could bring in someone to help you with them.

See if there are ways that you can create, like I said, content buckets, consistent content that you create week after week, so you’re not starting from scratch. Find ways to maybe have some weeks that take more time and effort and some weeks where it doesn’t take as much. You’re still delivering the value, but maybe it doesn’t take quite as much time and effort to produce. Even hamsters have to take a break once in a while.

Jerod Morris: That’s right. How about for the digital entrepreneur who already has a membership site and wants to iterate it and take it to the next level? What’s the biggest piece of advice that you would give to that person?

Pamela Wilson: Yeah. I would say, again, if you don’t have systems in place, getting them in place and finding ways to make your job easier is going to help you just keep your momentum and your enthusiasm going over the long haul.

And I’ll share this link with you. There are interesting problems that happen after you do have quite a bit of content on a membership site, and Debbie Hodge actually wrote about that for us on Copyblogger, about what you can do to organize your content to make it easier to get through, easier to find, and things like that. I’ll share that post with you. That’s a fantastic resource. Those are the problems you have once you have a membership site that’s been around for a while, and you have a lot of content.

Jerod Morris: Perfect. You will be able to find those in the show notes. Pamela, thank you so much. This was wonderful. We really appreciate your insights, and I know I am looking forward to seeing you speak at Digital Commerce Summit. It’ll be a good one.

Pamela Wilson: It’s going to be so much fun. I can’t wait to be there.

How to Take Your Digital Business to the Next Level

Jerod Morris: It is. It’s going to be great. We hope that you will join us. Again, the conference is October 13 and 14 in Denver, Colorado. For more information, go to Rainmaker.FM/Summit. There are still early bird tickets, and as I mentioned earlier, it’s going to be a great event, and it’s the place where you will discover smarter ways to create and sell profitable digital goods and services.

Maybe you have a digital product or service, and you want to take it to the next level. Maybe you’ve been thinking about it. You’ve been thinking about getting started. This conference would be great for you as well. Rainmaker.FM/Summit.

We hope to see you there, and we hope to see you on the next episode of The Digital Entrepreneur, which will be here next week. Until then, take care, everybody.