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Start Your Successful Podcast in 2017, with Jon Nastor

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Start Your Successful Podcast in 2017, with Jon Nastor

It’s been a year-and-a-half since I started Unemployable. And it’s just been recently that the show has started to take off.

Many assume because the Copyblogger audience is so large that the show would be massively popular from day one. That’s not the case though — a different format and a different topic does not automatically translate one audience into another.

For some reason, people have a hard time believing me on that. So today let’s talk to someone who has built a successful podcast completely from scratch — Jon Nastor of Hack the Entrepreneur.

Jon entered a crowded and competitive field with his podcast, and yet he’s managed to grow an audience that attracts lucrative sponsors. While there are plenty of other revenue opportunities for Jon to take advantage of, the sponsorships alone bring in enough to comfortably support the Nastor family.

The secret? Finding the gap in the market. Tune in to hear how Jon did it, and how you can do it for yourself. Plus, lots of insider info on how to attract sponsor relationships and price your ads.

The Show Notes

The Transcript

Start Your Successful Podcast in 2017, with Jon Nastor

Voiceover: Rainmaker FM.

Jon Nastor: I’m Jon Nastor. I like my businesses the same way I like my music, fast and independent, and I’m unemployable.

Voiceover: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one, and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs get actionable advice and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our free Profit Pillars course or choose to sign up for the newsletter only at no charge. Simply head over to Unemployable.com and take your business and lifestyle to the next level. That’s Unemployable.com.

Brian Clark: It’s been a year and a half since I started Unemployable and it’s just been recently that the show has started to take off. Many assume because the Copyblogger audience is so large that the show would be massively popular from day one. That’s not the case, though. A different format and a different topic does not automatically translate one audience into another. For some reason, people have a hard time believing me on that. So today, let’s talk to someone who has built a successful podcast completely from scratch, Jon Nastor of Hack the Entrepreneur.

I’m Brian Clark, and this is Unemployable the podcast that provides smart advice for freelancers, consultants, coaches, and entrepreneurs. If you’re digging the show and find the advice useful, please help me out and leave a rating or review at iTunes. Simply use this link, Unemployable.com/iTunes and you’ll magically end up where you need to be. Many thanks.

Jon entered a crowded and competitive field with his podcast, and yet he’s managed to grow an audience that attracts lucrative sponsors. While there are plenty of other revenue opportunities for Jon to take advantage of, the sponsorships alone bring in enough to comfortably support the Nastor family. The secret? Finding the gap in the market. Keep listening to hear how Jon did it and how you can do it for yourself. Plus, lots of insider info on how to attract sponsor relationships and price your ads. If you’re serious about building a business around a podcast, you’ll want to check out the Rainmaker Platform. Both Unemployable and Hack the Entrepreneur are on Rainmaker, because there’s a lot more involved than just audio episodes. That said, Rainmaker’s podcasting features were created with audio entrepreneurs in mind.

Plus, you’ll have all the other elements for growing your audience and generating revenue, such as email, marketing automation, digital commerce tools, membership functionality, an online course builder, and more. Take a no obligation free trial and see for yourself. Just visit RainmakerPlatform.com and discover the power of Rainmaker. That’s RainmakerPlatform.com.

Okay, on with the show. Mr. Nastor, how are things over there in Canada?

Jon Nastor: Things are pretty good up here in Canada.

Brian Clark: Yeah?

Jon Nastor: Yeah.

Brian Clark: Do you have a foot of snow on the ground in front of you?

Jon Nastor: I have zero snow.

Brian Clark: I don’t like you, because I think it’s more than a foot of snow, actually, that I had to scrap off my Jeep this morning.

Jon Nastor: You seem so far south. You are so far south from me, it blows my mind.

Brian Clark: Well, this Colorado thing. Who knew there was snow?

Jon Nastor: In the Rocky Mountains.

Brian Clark: Yeah. How are things, man? How’s the business?

Jon Nastor: Business is good.

Brian Clark: Yeah?

Jon Nastor: Yeah, heading this new year starting … Getting some things in line for the first quarter, it’s good.

Brian Clark: Yeah, that’s what I hear and that’s what I want to talk about today. Because, you’ve built quite the thing going on over there with Hack the Entrepreneur. For a couple years now I guess, we’ve been hearing podcasting this and that and we know some of our friends who started in 2010 and they’ve got these giant audiences. It’s just natural to think, It’s too late. I missed the boat. I don’t believe that’s true, and I don’t think you believe that’s true.

Jon Nastor: I absolutely do not believe that’s true. I actually had a conversation with somebody last night who I hadn’t talked to in about a year and a half. He launched his show almost identical to the time I did and he just reached out to me again. He’s quit all of it and he’s like, “I’ll never be able to do what I did back then.” It’s like, “Well, not if you don’t do it, no. If you absolutely just complain about everything.” Yeah, to me it’s the same as it ever was. It all takes work. It takes a lot of work and dedication and fighting for it.

Brian Clark: Yeah, people breakthrough every year and the thing they have in common, like you just said, is they didn’t quit.

Jon Nastor: That’s exactly it. I don’t know if there’s more to it, I think there is possibly, but

The Birth of a Podcast

Brian Clark: There may be more to it, and we’re going to get into that, but first of all, why don’t we go back a bit before you started Hack the Entrepreneur, what was your entrepreneurial journey up to that point?

Jon Nastor: Yeah, for sure. I actually started sort of offline. I was actually in the construction business for a while out in Vancouver. I believe it was like 2007 or something, I just got completely fed up with that. I had a new daughter at the time and I sold the business, sold our house out there, and we moved back across the country. And I discovered this internet thing, which I had known and used since I was, obviously, young, but I didn’t know it as a place for commerce, and so I decided that I was going to figure it out.

I spent years, two years actually, too much time to the point where I actually had to go back and get a job. Then I just started building stuff, and I spent like, I guess it was seven or eight months working full time building products and then I could finally step away and go full time into entrepreneurship. I did it full time two years before, that would have been 2014, yeah, 2014 in March when I ended up at a conference in the Philippines, Chris Ducker‘s, actually, first one.

I was at a point where I had kind of got to live that cool digital lifestyle, working on a beach, hanging out with the family, working from a laptop, but it got kind of boring. I kind of wanted to be known, or get sort of in the front of it and I was just behind the scenes making good money, but it wasn’t satisfying me in some way. Some smart podcasters where there and they’re like, “Jon, you have to start a podcast.” I was like, “Dudes, I don’t know how to speak into a microphone. I’ve never interviewed anybody in my life and I don’t have a voice for it.” They all kind of talked to me about it and then three months later after ignoring it, and ignoring it, I just started one July day. And I spent the whole summer putting together a show, that I didn’t know what it was called or what it was going to be, exactly, yet.

Brian Clark: That’s interesting. So you were behind the scenes, like a lot of people are and I always tell people that some of the smartest people out there are smart enough not to put themselves out front. I’m kicking myself daily, still. There’s an aspect to it I like, but there are some people like Brogan, Chris Brogan, he thrives in front of audiences, right? I’m not necessarily that way, but I definitely saw the benefit of it and it just happens. If you put yourself out there and you do good stuff, then people are going to start to know who you are. I mean, I guess that’s how it works. Mr. Ducker would know that, right?

Jon Nastor: Exactly. Mentioning like, Chris Brogan and Ducker, Chris Ducker they both … They have something that I don’t have in the fact that they love that audience, right? They’re just natural. I found out now that I don’t … I’m not actually like that and I don’t necessarily … That wasn’t I guess what I wanted. I wanted to be able to I think have just cooler people around me. It was so insular, I was in a tiny city at the time, literally in the middle of nowhere, building a business and there was … I’d be the only person in a coffee shop with a laptop, you know what I mean? That’s what I mean where I wanted to branch out and get known.

I didn’t so much want to build this huge audience around me. That just kind of happened, and then I decided to make a decision to push it or just to ignore it and go back. I decided to push it. That’s something I found out, is that I don’t really want to necessarily be that person who’s just always in front, because I’m really, I think I’m too introverted for that. It exhausts me sometimes. I love having people email me and wanting to talk to me and stuff, but it’s still hard for me, that part of it.

Brian Clark: Yeah. Both of the Chris’s are consummate showman types and I think you and I, we can certainly do the job, but then we have to go hide, right?

Jon Nastor: Yeah, no exactly. I really, really … Like after a business conference that lasts three days, I’m wiped out for a good five days after, where I just need to huddle in my room, listen to a record, read a book, and just drink coffee slowly. But I love it when I’m there, it just it takes a lot out of me.

Brian Clark: Right. Okay, so you’re at Ducker’s Tropical Think Tank, people are saying you need to start a podcast. Apparently, you were convinced. Take us through the process of deciding, “Okay, what does Jon Nastor want to do?” Which we know is important, and I know it’s important to you. You couldn’t … Well, I know I can’t just do anything because it makes money. I have to also be into it, or it’s not going to last very long.

Turning Your Passion Into Action, and Finding the Gap

Jon Nastor: Right, yeah. This wasn’t about money at all. There’s two things that I’m really into, it’s music and it’s business. Two things that I’ll literally sit down over a beer or a coffee with anyone and talk business or music. Unless they don’t like good music, which most people don’t. That’s besides the point. I couldn’t figure out a way to do music, so it didn’t matter. I was like, business, I want to … I’m still in this tiny city in the middle of nowhere. I want to talk to 30 smart business people that I’ve admired for quite some time, so I’m going to do that. I wrote the list out and still didn’t have a name or anything, but I knew there were certain aspects of things that I wanted to sort of incorporate. I knew what I didn’t like about podcasts, or I knew where the ball was sort of dropped on lots of shows, and I wanted to sort of try and alleviate that in my show.

What I’m referring to there is that I find that I tune out a lot of times sort of part way through a podcast, because I’m working out, or I’m walking the dog, or I’m doing something. All of a sudden you come back in ten minutes later it’s like, “Oh.” I wanted to try and tie people in, so that’s where this idea of the hack came, which comes at the end of the show where I try and do my little essay on a part of the sequence and then people email me and argue with me that that shouldn’t have been the hack and to me that’s the greatest thing ever, because they

Brian Clark: No, that’s awesome. Talk about interaction and engagement.

Jon Nastor: Right, and so during this two months, so it started early July when I just decided, I’m doing the show and I’m going to launch it September 5th. I think it was actually July 5th, because it was two months I gave myself and some arbitrary number … I’m going to launch a show. I had some cool smart people around me, and so I was giving them interviews that I was doing and I was working on questions with them and I was just trying to get their feedback.

I incorporated this hack into the show for the first five episodes, but it happened right when the show … Right when it happened in our conversation, all of a sudden I’d put in a rewind sound and we’d replay it and I’d be like, “Oh, and that’s the hack,” and then keeping going. People were like, “That’s really cool.” I was like, all of a sudden I was jostled into paying attention again, but then I stopped paying attention, because it was like, “Well, that was the best part of the show. Why do I … ” I was like, “Oh, interesting, interesting. Okay, we got to move this to the end.”

It was, to me, which is all I had ever done up til then was really create software, so it was iterative sort of process. It’s like, “I got to create a really, really crappy version and I’m going to hand it out to friends that I trust.” Not friends that’ll just tell me that it’s good, but they’re going to tell me feedback and things and tell me questions that could be better, because I’d never interviewed anybody, so I needed to work on this. It was just this process and then some time mid to late July, one of my good friends in Australia came up with the idea called Hack the Entrepreneur and I was like … Looked it up and it was actually available as a domain so I bought it instantly because I was like, “Wow, for ten dollars that’s a pretty good domain, but I really don’t like hacks.” Then I was like, “But it works with this hack thing that I’m trying to create.” That was sort of the evolution of it.

The whole basis for the show, Brian, was that all of the shows that existed until then, so I didn’t go to the whole niche down, like, Entrepreneurship, right? It’s the big sort of business section. I didn’t try and niche down from there to something small, I was like, “No, screw that. If I’m going to do this, I’m going to go big.” I looked for a gap, and everything that I found then and everything that I listened to was very tactical, was very much, How to do this. Here’s the seven steps to this. And you’d have an expert on and you’d talk about how to do … It wasn’t Facebook ads at the time, but whatever it was at the time, right? SEO or something.

I was like, “That’s really, really cool and super, super absolutely useful,” but mindset to me is like the big thing, that’s the … There was this correlation I found with all the people I knew around me doing stuff in business where they just had this different way of perceiving the world. I was like, “That’s the gap in the market. That doesn’t exist, for some reason, in the marketplace.” I didn’t talk tactics at all. We teach through just showing the mindset, showing how people think. I still start my episode, tell people before they’re on, it’s like, “There’s no right or wrong answers. There’s no seven steps to anything. When I ask you a question and you don’t know the answer to it, say you don’t know the answer, and then let’s kind of work through that, because we need … Other people need to know that we don’t have all of the answers all of the time, but the job of us as entrepreneurs is to just continually be learning and growing and trying to stay just far enough ahead of our companies.”

That was the gap. I knew, again, like creating any product, is you just have to find a gap in the marketplace. To me, that was the gap. That gap has now been filled and now there’s 50 other podcasts behind me like that, but at the time that’s what it was. Every market has gaps, always, but

Knowing When to Reveal the Hack

Brian Clark: All right, all right, all right Jon. Now if this were your show, you just revealed the hack right up front and now I’ve got to convince people to keep listening. That was it. I mean, I always tell people, “Look, you don’t want to find … You don’t want to go niche. You don’t want to find something that no one else is talking about. No, you want to go in where there’s tons of competition because you know there’s an audience there and then you want to position yourself in the gap.” That’s it. And you just explained how that came to you. Let’s drill down a little bit, because … Everyone keep listening, dang it.

Jon Nastor: Sorry, sorry.

Brian Clark: What’s interesting, to me, is you weren’t just sitting there in some abstract looking out the window creative mode going, “Hmm? I think I’ll call it Hack the Entrepreneur, and this, and this, and this.” No, you were doing, you were researching, you were bouncing off ideas, and it revealed itself. I cannot stress, that’s how it happens all the time. Roll your sleeves up, dig in, you don’t know what it’s going to be, you don’t know where you’re going to find it, but that’s how you find it. It’s not staring out the window.

Jon Nastor: Right, exactly. It’s I think also taking things as they come, but with imperfections maybe? Like, Hack the Entrepreneur I did not like as a name. I just need to stress that. I had a hard time, at first, being able to get my head around having it … Because I don’t like

Brian Clark: The hack thing annoys me too, but it resonates with people.

Jon Nastor: Exactly, so

Brian Clark: You’ve got to go with it.

Jon Nastor: I know, and to find a dot com that has entrepreneur in it, you know what I mean? I had to, at the beginning, convince myself that, It’s not exactly perfect, but I can get behind this fully. This is cool, all right, let’s go for it. Then the other thing was that once I found the gap I wanted to fill by you’re right, doing a ton of research, listening to way too many podcasts, I 100% completely never listened to another podcast until, I’m going to say, like mid November of that year, because I was in … This is the same way I’ve created anything. If I’m creating a product in any market, I need to know what’s out there, I need to know what’s good, what’s bad, but as soon as it’s time for me, personally, to start creating it, I cannot look at other stuff anymore.

One thing, because I know that as soon as I’ll create an episode or I’ll put in the new music and then I’ll go listen to another one and be like, “Oh, they got so much cooler, maybe I should change mine.” Then it’s like, “Okay, maybe I’ll launch in October, maybe I’ll launch in November, maybe …” It’s like, “No man, just …” I had to trust myself that I had taken in enough stuff, I’d found my gap, and now I have to trust my instinct to market, to create a product, and that I’m at least smart enough and slightly unique enough that people might dig this. I just went for it, and I literally did not listen to anything again and then I actually launched on September 5th, like I said I would.

Brian Clark: I’m the same way. I mean, I dig into everything. I look at everyone. I was thinking, in your case, there’s these shows out there like Entrepreneur on Fire and Smart Passive Income, these guys who started early. I mean, you’re really doing something similar and yet you’re not. I mean, this is definitely Jon’s show, just like … Or your Jon, J-O-N, not J-O-H-N.

Jon Nastor: That was close. John Lee Dumas and Pat Flynn were both at that conference.

Brian Clark: Oh, really?

Jon Nastor: They were two guys that sat across from me and they were like, “Dude, you have to start a podcast.” I’m like, “That’s because you guys are really good podcasters.” They’re like, “No, we weren’t good podcasters. We started two years ago, yes, but you have to.” Pat Flynn actually bought this gear that I’m actually speaking on, so it was kind of like, “Okay, okay, I’ll do it, I’ll do it.” Then it took me three months to get my head around it.

Brian Clark: Yeah, well that’s not too bad. I mean, for a run-up period, that’s … Three months is acceptable.

Jon Nastor: I kind of stopped thinking about it, but I just I was there, and it’s like, the gear was here, and it was kind of like, “It’s going to happen at some point,” but then all of a sudden it was July, that was it. I was like, “This is my summer and I’m launching September 5th.” Yeah, I mean I have to thank those two dudes, they were the guys sitting across the table with 18 other people.

Keeping on Track, and Persevering

Brian Clark: Interesting. All right, well let’s talk about something that relates to the catchphrase for this show, which is keep going. It’s so crucial, as we were disgusting. Disgusting? Nice … Discussing before the show … Unemployable, after a year and a half, is just now getting what I consider some traction and you started Hack the Entrepreneur I think a full year before me, is that right?

Jon Nastor: Yeah, I believe September 5th, 2014.

Brian Clark: Yeah.

Jon Nastor: Two and a half years ago, almost.

Brian Clark: It does take some time and I think people need to understand that. I don’t care if you have an audience to start with or not, when you do something new, it’s a new thing and you don’t know exactly how people are going to respond and at what speed. For podcasting for sure, you’ve got to put the time in. I can remember us having a conversation. It may have been six months ago. You were in this space where, I don’t know what I’m doing next, kind of thing, and we had a couple conversations and I said, “Jon, you are doing your next thing. Keep doing it, right? Where did that come from for you, were you restless or were you not sure that Hack was going to be the thing?

Jon Nastor: I am restless, that thing is still sort of there. Your voice is still in the back of my head keeping me patient. This is … I don’t know, Brian, I think this comes from the fact that I come from software and product, and to me, that was a tangible sort of thing I was creating and enjoying, and now I don’t have that. Now it’s … All of it’s based on me and me talking. Sometimes I have a hard time perceiving that as a product, or as a business. Although, it fully is and completely pays for my family.

It’s something that I so didn’t plan on doing. I mean, it’s that whole, None of this made sense going forward, and looking back it’s like … It makes sense where I am now, totally, but I never would have planned this. There’s no way I ever could have, it’s the way it went. Sometimes I struggle with that, because of it’s uncomfortable for me, the position that I’ve put myself into. Which is a good thing usually, but it is a thing and now … Yeah, I don’t know, maybe I need to create more stuff.

Brian Clark: No, I get it. Sometimes it’s hard to accept that you’re having fun and getting paid, you know what I mean?

Jon Nastor: It’s crazy, it doesn’t even make sense.

Brian Clark: To be you, because as you mentioned earlier, these are the things you would ask these people anyway. Yet, you just hit record. I mean, there’s more to it than that. You’re a great interviewer, and that takes practice, it takes skill, it takes preparation. But still, if you’re curious in what the guest is about and their experience then you’re just having a good time.

Jon Nastor: Yeah, no exactly. I’m fascinated by every single conversation I get to have. I would have it absolutely for free. I would pay for the beer most of the times if that’s what it took, but instead I just get to hit record and put it out to a lot of people that listen to it. Which also, if I can’t think about that every single time, otherwise it’s hard. If every goofy thing I say on my show, I think that it’s going to be listened to by 100,000 people, it’s hard for me so I tend to not do that.

Brian Clark: That’s funny, because I’ll say something, or tweet something, or just something stupid that I think is the end of the world and no one cares. You know what I mean?

Jon Nastor: Yeah, I know.

Brian Clark: It’s not a big deal, we’re just so harsh on ourselves from a self criticism standpoint.

Jon Nastor: Right, I agree.

Brian Clark: Okay, so if your sponsorship page is current you’re up to over 20,000 downloads per episode, right?

Jon Nastor: Yes.

Brian Clark: That’s nice. Ball parking it, and we can … I want to dive into this a bit, because I think there’s a lot of mystery to a lot of people about how podcasts make money, how to deal with sponsors, all that good stuff. Maybe this is how we’ll keep people listening after you revealed the hack too early.

Jon Nastor: I’m terrible at this.

Getting Paid

Brian Clark: No, but so for 20,000 downloads we’re looking at a sponsorship rate of about 1,000 bucks, right? For say the standard 15 second pre-roll with a 60 second mid-roll. Let’s define for people … If I’m wrong, tell me, but let’s define this for people so they understand what we’re talking about here. How do you get paid with these sponsorships?

Jon Nastor: I get paid in advance, first of all. I never do any of it, I don’t even write copy until I’ve been paid in advance for all episodes on the contract. This has been a real sort of fluid evolution with me. I joined about 14 months ago, 15 months ago I joined a company called Midroll. They run sponsorships for companies, or for podcasts, they’re like the intermediary. In the end of November, so just a couple of months ago, I left them. I’m in a real transition sort of phase of taking back control and having more of a direct relationship with my sponsors. It’s a lot different now, it’s more like it was in the beginning, except I have a much larger audience, so I can control things better. I’d lost control is the easiest way to say it and the nicest way to say it, in case you’re listening, Midroll, that’s where I’ll keep it at. I’m in more control now and I’m unemployable, right? I’m kind of a control freak in that way and so I like it.

Now the idea is, right now, as of right before Christmas when I went on the holidays, I took a week off, I was like, “Okay, this is my first time in almost two years that I’m fully in control of my own sponsorships.” I reached out to three companies and I landed three sponsorships and I sold out every episode until the end of March. Then, as of yesterday, actually I sold out into May. Those are all paid in advance. Those are companies that I fully 100% use and endorse. I’ve switched from having a pre-roll and a mid-roll that are different companies, because I think it just messes up the whole thing for my audience and for me.

Now one person sponsors every episode. They do, they get … I don’t really push 15 seconds or 60 seconds, whatever it is, there’s kind of a warm up sort of one at the beginning, which is the pre-roll, just kind of says the URL and tells them about the company really quickly, but leads into sort of the story based main mid-roll. Then that can run anywhere from 40 seconds to two minutes. For the same sponsor, but because I only let people buy a minimum of ten episodes now, that’s just how

Brian Clark: Oh, really? Interesting.

Jon Nastor: Yeah, it’s too much work, Brian, to write copy and stuff for people, like no …

Brian Clark: No, I know. Let me tell you my experience and I know FreshBooks sponsors your show, so they reached out to me and I’m like, “Okay.” I understood generally what the industry CPMs were and it’s really funny, because I negotiated that deal before I got this spike in subscribers from being mentioned in Inc. Magazine. They got a great deal, but here’s something smart. I guaranteed them that … They did nine episodes, okay so the first month I gave them 7,000 downloads, which is what it was at that time, minimum. Then of course now it’s at 14 or 15. Month two and three, or three through nine episodes, I can make up for actual downloads that are actually delivered. Do you have that sort of caveat in your deals, or do you just say, “You’re buying this many downloads and if it’s more than that, then great?”

Jon Nastor: We actually don’t even talk downloads that much, interestingly enough. I don’t know

Brian Clark: Wow, okay.

Jon Nastor: If it’s because I’ve been around a long time. I don’t work on CPM.

Brian Clark: Oh, okay. That’s cool.

How CPM Works

Brian Clark: Let’s back up and explain how CPM works, because we’re talking past some people, I think, right now. Then talk about how you do it.

Jon Nastor: CPM is cost per thousand, right? Per thousand downloads and that thousand is based on six weeks from the date you publish, six weeks out is the industry standard. However many thousand downloads you have in that six week period, then you get paid. Right now I think a mid-roll, they go from anywhere from 15 dollars up to 35 dollars per CPM, so per thousand. Meaning, if I get 10,000 downloads and my CPM is 25 dollars, I’m going to get what? 250 dollars is that? Or 25- I don’t know, I’m terrible at math too.

Brian Clark: Yeah, here’s how I figure it out, because usually … Well, if you’re selling the pre-roll and the mid-roll together, which I think is a good policy, you want that consistency. Roughly, and this, you can set your own prices, but this is just kind of the industry rule of thumb. Multiply 43 times, if you have 10,000 downloads, then times ten, and that is the cost for those two spots in that episode. The actual … The pre-roll and the mid-roll are priced differently. I think it’s 18 versus 25, but that’s just a rule of thumb if they’re grouped together. 43 times per thousand, right? If you have 10,000 it’s ten.

Jon Nastor: Exactly. When I was running through a company, Midroll, the company, it was 100% CPM all the time and I kind of didn’t like it. I’m really into having a partnership with a company that I’m dealing with. I think it’s more effective for me, I think it’s better for my audience, and I think it’s better for the company. The numbers are there, we know the numbers are there, but after that it’s really, we’re trying to create kind of a good, unique, experience that works really well. Meaning, that we don’t have to have that really hard call to action in that first 15 seconds or whatever it is, and everything can kind of flow. It gets me a good offer from the company with a unique landing page so that it shows that this is unique and this isn’t the same one you’re going to get everywhere else, which makes people take more action and it makes people not tune out during those.

Then you can offer things like links into the show notes, obviously, links into your newsletter if you want, which I have never done the newsletter part of it, but I have put … FreshBooks actually right now is in my sidebar of my site and that’s part of just the partnership package that they’ve taken. They bought them for 15 episodes starting yesterday, actually, they started. To me, it’s too, I don’t know, it’s what I wanted to get out of. I wanted to get back to having those partnerships with those companies. I also like to … I’ve lowered my rates a bit right now, just because I wanted to fill them up and prove to myself that I still could, because I’ve been dealing with another company for so long. I didn’t want to just be running without sponsorships and it sold way faster than I expected.

Brian Clark: Without getting too much into your business, would you say you’re charging more or less than that general CPM rule of thumb?

Jon Nastor: Right now I’m charging less.

Brian Clark: Okay.

Jon Nastor: If I was charging per episode, I would be charging what you’re saying or more. Actually, that’s part of my pitch. I show my regular rate, and then I say, “At ten it drops to this. At 15 it drops to this.”

Brian Clark: Nice.

Jon Nastor: That’s just because I get to use basically the same copy. I record new versions, but we work together on the copy quickly and then it’s on a Google Doc. They can change stuff as we go live with different episodes if they want. It’s easier for me, and I feel good doing it, so I feel that it helps … I feel like I was really losing parts of my audience or engagement when it was two wacky sponsors, one in the beginning, one in the end. One’s a mattress one, one’s like … It was total nonsense and I didn’t like it and I should have stopped it probably sooner, but I didn’t. Now I’m getting back to where I want to be and I’m going to take a slight financial hit in the short term for that.

How to Be Smart about Your Income

Brian Clark: Yeah, but I think that’s smart. The idea that a lot of people seem to miss is that you shouldn’t be trying to milk everyone for every cent. You’re trying to establish a long term relationship. That’s more valuable than the exact dollar amount you make this episode, right? Yet, I see a lot of people who have that mindset and I don’t think it’s conducive to succeeding.

Jon Nastor: Oh, yeah. I would way rather have the rate I have right now and have these three people sign on next quarter, and next quarter, and next quarter, because I like it, I think it’s better for my audience, I think it’s better for everything, and it’s less work. It’s easier and I get to build that relationship. I just moved to Toronto where FreshBooks is based out of. I mean, when I first got here it’s like they invited me and I spent the afternoon in their office and that’s pretty cool.

Brian Clark: Yeah.

Jon Nastor: To me, that’s pretty cool, that’s a good relationship to have.

Brian Clark: Right now FreshBooks is getting free exposure.

Jon Nastor: Exactly. They have been for years, they were my first sponsor ever-

Brian Clark: Mine too.

Jon Nastor: When the show was hardly anything, that’s just how it is.

Brian Clark: Yeah. Okay, let me ask you this. Do you experiment at all … See, I would never do the Midroll thing, no offense. I mean, I thought about it and I heard about it, but I think going into it I would feel wary of the very experience that you ended up having, right? Because you almost think, That’s got to be the way it is. You know? I don’t think anyone’s ever dealt with a company like that and said, “This is fantastic.”

Jon Nastor: I did it for a different reason. I did it to potentially help my show grow and I think it did in the short term. Meaning that, it’s really hard to get onto Midroll.

Brian Clark: Oh, is it?

Jon Nastor: They have it right clearly on their site that you have to have 50,000 downloads or more per episode, which I didn’t have. They had reached out to me, so I launched in September, at Christmas time they reached out to me. I didn’t even know who they were, but as soon as I went to their site it was like, “Wow, they have John Lee Dumas, they have Tim Ferris, and they had Hundred Dollar MBA. That was like three shows I totally admire and then me … I actually turned them down. I said, “No, that’s cool. Thank you so much, but I’ve got it under control,” and I had just sold FreshBooks for months in advance. They said, “Cool, if you ever change your mind, come back.”

In June of the following year I did change my mind. I said, “Let’s have the conversation. Let’s see where it can go,” because I had been talking to podcasters at this point. I wasn’t a podcaster, I didn’t think, until then where I kind of entered the market. Talking to a lot of people and Midroll kept coming up and it was like kind of this elite weird thing where people were like, “Yeah, those shows are doing so amazing. They’re … ” I was like, “Man, I could just be on Midroll. That’s kind of cool.” I approached them, we had big long conversations, it took about two months to sort out, and then I got on there. Then I was just flooded with people emailing me like, “Man, can you get me on Midroll? Can you get me on Midroll?” It helped in that way.

Brian Clark: Oh, okay.

Jon Nastor: Completely indirect from how they’re supposed to help me, but that is 100% why I did it. Then after that I just stuck with it too long.

The Potential Benefits of Affiliate Sponsors

Brian Clark: Got you. Okay, so have you experimented at all with affiliate sponsors? The reason I think that may be interesting, as you well know, a sponsor gets the benefit of being in that episode forever and we know that listenership goes way down after six weeks, but people still listen to my old shows, right? As a content marketer, that’s great, we were promoting our own stuff. But what about an affiliate, a perfectly matched affiliate offer to what the topic is and you get the benefit of the fact that that’s out there forever and could be earning you some residual income while a traditional sponsor wouldn’t?

Jon Nastor: Yeah, it’s a really smart idea and the only times that I’ve done affiliate sponsorships, or like ads, is when I didn’t sell the spot. There was quite a few second quarter of last year and then early third quarter. For some reason Midroll just was struggling to sell spots and so I just filled it up with different spots. They kind of work, but they kind of don’t really that well. That’s not to say that the idea of affiliates doesn’t work, it’s just I didn’t target it right, or I didn’t read the spots right, or whatever that happens to be. Right now, Brian, the way I think about it is, it’s like I mean, what am I going to do? Am I going to cancel somebodies sponsorship that they prepaid me for?

Brian Clark: Oh no, it would only be in the event that you didn’t have a spot filled.

Jon Nastor: Oh, 100%.

Brian Clark: Yeah.

Jon Nastor: When I quit Midroll in November, that’s all I said. I was like, “I’m going to quit Midroll and for the first quarter I will probably have to run affiliates and I’ll have to find some cool companies and run that.” Totally cool. I was totally happy with that. Instead, I just went out on a sales pitch for a week and I sold all three month s worth. I didn’t have to do it, but I definitely would have done it and I think if I was starting over and didn’t have a way to get sponsors right away, that’s definitely how I would do it. Because I think that shows should have ad spots.

I think shows should have an ad spot before you get a sponsor, you should be running a thing that sounds like an ad spot, but is an affiliate because it gets people used to it and that’s another whole level of making your show seem more professional. If I listen to Tim Ferris and I listen to Pat Flynn and they have ad spots and now I listen to Jon Nastor and he doesn’t have ad spots, it’s like, “Oh, this guy is totally just a rookie, he … ” All of a sudden you’re on a different level, so you should be running those affiliates. I’m lucky enough that I fill up all the time whenever I try, so …

Brian Clark: See, good thing you stuck with it.

Jon Nastor: Exactly, yeah. I mean, I guess sales don’t bother me, I enjoy sales, so actually-

Tips For the Sales Process

Brian Clark: Yeah, tell us a little bit about that because I’ll write copy all day long and close people that way, but getting me to write an email cold reaching out to someone, I’m just … All of a sudden I lose my nerve. Tell us a little bit about that process. How do you go about selecting companies, approaching them? It seems that it s been successful, you are three of three.

Jon Nastor: Yeah, for sure. I’m terrible at writing copy. I can pick up the phone and phone somebody and I feel like I’m really good at making a sale. I kind of enjoy it and I’ve … When I did it right before Christmas, I actually after that one week I said to my wife, I was like, “Man, I really missed that. I really miss just hustling and getting on the phone with people and just closing them. It was awesome.” It really is … I mean, to find the sponsors, it’s easy. You know, you’ve already found the gap of the market you’re going to hit, you find the gap in between other shows. Look at those other shows and look at their sponsor pages. Who’s sponsoring them? Reach out to those people. There, that’s pretty easy. You just literally reach out, tell them about your show quickly and ask them if they’d like to talk on the phone. Then they get on the phone with you, and now think about it, you are making a pitch.

This is where most people, I think, fail. They don’t want to feel like they’re selling. You are selling something. These people have to buy what you are selling. You’re selling them the ability to connect with your audience who will buy a ton of their stuff. That’s huge, right? Don’t undervalue that and make it like a sales. Not like a sales pitch in that way, but you are selling, you have to close these people. When you send them then … Follow it up with say, an email that sells them everything you said, everything they’re going to get, what they’re going to pay, make it look good. I go on Canva. It takes me 15 minutes, but I go on Canva, I brand it with my show, put some cool colors in there, some graphics, make it look like, “Holy dammit, this thing looks pretty damn pro. Yes, of course I’ll sign for that.” Perfect.

Brian Clark: Excellent.

Jon Nastor: I see what some people do for pitches, it’s like, “Dude, what are you doing? You wouldn’t buy this.” They’re like, “Well, they’re just buying the spots.” They’re not just buying the spots; they’re buying a partnership with you and your audience. You have to know that and you have to sell that to them, because that’s what they’re buying.

Brian Clark: Excellent. That’s good advice. I hope people stuck around after you, you know, did the reveal too early.

Jon Nastor: I’m never going to live that down.

Brian Clark: I’m going to harp on this, like every time I talk to you, see you, anything, I’m going to be like, “Thanks Nastor, way to go.” No, no, this was good stuff. Well, I’m glad you’re rolling with it. It’s a great show, it’s turning into a great business. I think, as you’ve seen with other podcasters, sponsors are just the beginning. There’s so much more you can do with your own products, and I know you wrote a book already, we didn’t even get to that. You can launch courses, all of that. I think we’ll just visit with you again in a year or so and see how the empire is doing.

Jon Nastor: I love it. Thank you so much, it’s been a blast.

Brian Clark: Yeah, thanks Jon so much. All right everyone, if you’re thinking of starting a podcast this is a great way to get started. It’s not too late, find your gap, serve your audience, and stick with it. You know what I’m about to say: keep going.

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Start Your Successful Podcast in 2017, with Jon Nastor

It’s been a year-and-a-half since I started Unemployable. And it’s just been recently that the show has started to take off.

Many assume because the Copyblogger audience is so large that the show would be massively popular from day one. That’s not the case though — a different format and a different topic does not automatically translate one audience into another.

For some reason, people have a hard time believing me on that. So today let’s talk to someone who has built a successful podcast completely from scratch — Jon Nastor of Hack the Entrepreneur.

Jon entered a crowded and competitive field with his podcast, and yet he’s managed to grow an audience that attracts lucrative sponsors. While there are plenty of other revenue opportunities for Jon to take advantage of, the sponsorships alone bring in enough to comfortably support the Nastor family.

The secret? Finding the gap in the market. Tune in to hear how Jon did it, and how you can do it for yourself. Plus, lots of insider info on how to attract sponsor relationships and price your ads.

The Show Notes

The Transcript

Start Your Successful Podcast in 2017, with Jon Nastor

Voiceover: Rainmaker FM.

Jon Nastor: I’m Jon Nastor. I like my businesses the same way I like my music, fast and independent, and I’m unemployable.

Voiceover: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one, and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs get actionable advice and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our free Profit Pillars course or choose to sign up for the newsletter only at no charge. Simply head over to Unemployable.com and take your business and lifestyle to the next level. That’s Unemployable.com.

Brian Clark: It’s been a year and a half since I started Unemployable and it’s just been recently that the show has started to take off. Many assume because the Copyblogger audience is so large that the show would be massively popular from day one. That’s not the case, though. A different format and a different topic does not automatically translate one audience into another. For some reason, people have a hard time believing me on that. So today, let’s talk to someone who has built a successful podcast completely from scratch, Jon Nastor of Hack the Entrepreneur.

I’m Brian Clark, and this is Unemployable the podcast that provides smart advice for freelancers, consultants, coaches, and entrepreneurs. If you’re digging the show and find the advice useful, please help me out and leave a rating or review at iTunes. Simply use this link, Unemployable.com/iTunes and you’ll magically end up where you need to be. Many thanks.

Jon entered a crowded and competitive field with his podcast, and yet he’s managed to grow an audience that attracts lucrative sponsors. While there are plenty of other revenue opportunities for Jon to take advantage of, the sponsorships alone bring in enough to comfortably support the Nastor family. The secret? Finding the gap in the market. Keep listening to hear how Jon did it and how you can do it for yourself. Plus, lots of insider info on how to attract sponsor relationships and price your ads. If you’re serious about building a business around a podcast, you’ll want to check out the Rainmaker Platform. Both Unemployable and Hack the Entrepreneur are on Rainmaker, because there’s a lot more involved than just audio episodes. That said, Rainmaker’s podcasting features were created with audio entrepreneurs in mind.

Plus, you’ll have all the other elements for growing your audience and generating revenue, such as email, marketing automation, digital commerce tools, membership functionality, an online course builder, and more. Take a no obligation free trial and see for yourself. Just visit RainmakerPlatform.com and discover the power of Rainmaker. That’s RainmakerPlatform.com.

Okay, on with the show. Mr. Nastor, how are things over there in Canada?

Jon Nastor: Things are pretty good up here in Canada.

Brian Clark: Yeah?

Jon Nastor: Yeah.

Brian Clark: Do you have a foot of snow on the ground in front of you?

Jon Nastor: I have zero snow.

Brian Clark: I don’t like you, because I think it’s more than a foot of snow, actually, that I had to scrap off my Jeep this morning.

Jon Nastor: You seem so far south. You are so far south from me, it blows my mind.

Brian Clark: Well, this Colorado thing. Who knew there was snow?

Jon Nastor: In the Rocky Mountains.

Brian Clark: Yeah. How are things, man? How’s the business?

Jon Nastor: Business is good.

Brian Clark: Yeah?

Jon Nastor: Yeah, heading this new year starting … Getting some things in line for the first quarter, it’s good.

Brian Clark: Yeah, that’s what I hear and that’s what I want to talk about today. Because, you’ve built quite the thing going on over there with Hack the Entrepreneur. For a couple years now I guess, we’ve been hearing podcasting this and that and we know some of our friends who started in 2010 and they’ve got these giant audiences. It’s just natural to think, It’s too late. I missed the boat. I don’t believe that’s true, and I don’t think you believe that’s true.

Jon Nastor: I absolutely do not believe that’s true. I actually had a conversation with somebody last night who I hadn’t talked to in about a year and a half. He launched his show almost identical to the time I did and he just reached out to me again. He’s quit all of it and he’s like, “I’ll never be able to do what I did back then.” It’s like, “Well, not if you don’t do it, no. If you absolutely just complain about everything.” Yeah, to me it’s the same as it ever was. It all takes work. It takes a lot of work and dedication and fighting for it.

Brian Clark: Yeah, people breakthrough every year and the thing they have in common, like you just said, is they didn’t quit.

Jon Nastor: That’s exactly it. I don’t know if there’s more to it, I think there is possibly, but

The Birth of a Podcast

Brian Clark: There may be more to it, and we’re going to get into that, but first of all, why don’t we go back a bit before you started Hack the Entrepreneur, what was your entrepreneurial journey up to that point?

Jon Nastor: Yeah, for sure. I actually started sort of offline. I was actually in the construction business for a while out in Vancouver. I believe it was like 2007 or something, I just got completely fed up with that. I had a new daughter at the time and I sold the business, sold our house out there, and we moved back across the country. And I discovered this internet thing, which I had known and used since I was, obviously, young, but I didn’t know it as a place for commerce, and so I decided that I was going to figure it out.

I spent years, two years actually, too much time to the point where I actually had to go back and get a job. Then I just started building stuff, and I spent like, I guess it was seven or eight months working full time building products and then I could finally step away and go full time into entrepreneurship. I did it full time two years before, that would have been 2014, yeah, 2014 in March when I ended up at a conference in the Philippines, Chris Ducker‘s, actually, first one.

I was at a point where I had kind of got to live that cool digital lifestyle, working on a beach, hanging out with the family, working from a laptop, but it got kind of boring. I kind of wanted to be known, or get sort of in the front of it and I was just behind the scenes making good money, but it wasn’t satisfying me in some way. Some smart podcasters where there and they’re like, “Jon, you have to start a podcast.” I was like, “Dudes, I don’t know how to speak into a microphone. I’ve never interviewed anybody in my life and I don’t have a voice for it.” They all kind of talked to me about it and then three months later after ignoring it, and ignoring it, I just started one July day. And I spent the whole summer putting together a show, that I didn’t know what it was called or what it was going to be, exactly, yet.

Brian Clark: That’s interesting. So you were behind the scenes, like a lot of people are and I always tell people that some of the smartest people out there are smart enough not to put themselves out front. I’m kicking myself daily, still. There’s an aspect to it I like, but there are some people like Brogan, Chris Brogan, he thrives in front of audiences, right? I’m not necessarily that way, but I definitely saw the benefit of it and it just happens. If you put yourself out there and you do good stuff, then people are going to start to know who you are. I mean, I guess that’s how it works. Mr. Ducker would know that, right?

Jon Nastor: Exactly. Mentioning like, Chris Brogan and Ducker, Chris Ducker they both … They have something that I don’t have in the fact that they love that audience, right? They’re just natural. I found out now that I don’t … I’m not actually like that and I don’t necessarily … That wasn’t I guess what I wanted. I wanted to be able to I think have just cooler people around me. It was so insular, I was in a tiny city at the time, literally in the middle of nowhere, building a business and there was … I’d be the only person in a coffee shop with a laptop, you know what I mean? That’s what I mean where I wanted to branch out and get known.

I didn’t so much want to build this huge audience around me. That just kind of happened, and then I decided to make a decision to push it or just to ignore it and go back. I decided to push it. That’s something I found out, is that I don’t really want to necessarily be that person who’s just always in front, because I’m really, I think I’m too introverted for that. It exhausts me sometimes. I love having people email me and wanting to talk to me and stuff, but it’s still hard for me, that part of it.

Brian Clark: Yeah. Both of the Chris’s are consummate showman types and I think you and I, we can certainly do the job, but then we have to go hide, right?

Jon Nastor: Yeah, no exactly. I really, really … Like after a business conference that lasts three days, I’m wiped out for a good five days after, where I just need to huddle in my room, listen to a record, read a book, and just drink coffee slowly. But I love it when I’m there, it just it takes a lot out of me.

Brian Clark: Right. Okay, so you’re at Ducker’s Tropical Think Tank, people are saying you need to start a podcast. Apparently, you were convinced. Take us through the process of deciding, “Okay, what does Jon Nastor want to do?” Which we know is important, and I know it’s important to you. You couldn’t … Well, I know I can’t just do anything because it makes money. I have to also be into it, or it’s not going to last very long.

Turning Your Passion Into Action, and Finding the Gap

Jon Nastor: Right, yeah. This wasn’t about money at all. There’s two things that I’m really into, it’s music and it’s business. Two things that I’ll literally sit down over a beer or a coffee with anyone and talk business or music. Unless they don’t like good music, which most people don’t. That’s besides the point. I couldn’t figure out a way to do music, so it didn’t matter. I was like, business, I want to … I’m still in this tiny city in the middle of nowhere. I want to talk to 30 smart business people that I’ve admired for quite some time, so I’m going to do that. I wrote the list out and still didn’t have a name or anything, but I knew there were certain aspects of things that I wanted to sort of incorporate. I knew what I didn’t like about podcasts, or I knew where the ball was sort of dropped on lots of shows, and I wanted to sort of try and alleviate that in my show.

What I’m referring to there is that I find that I tune out a lot of times sort of part way through a podcast, because I’m working out, or I’m walking the dog, or I’m doing something. All of a sudden you come back in ten minutes later it’s like, “Oh.” I wanted to try and tie people in, so that’s where this idea of the hack came, which comes at the end of the show where I try and do my little essay on a part of the sequence and then people email me and argue with me that that shouldn’t have been the hack and to me that’s the greatest thing ever, because they

Brian Clark: No, that’s awesome. Talk about interaction and engagement.

Jon Nastor: Right, and so during this two months, so it started early July when I just decided, I’m doing the show and I’m going to launch it September 5th. I think it was actually July 5th, because it was two months I gave myself and some arbitrary number … I’m going to launch a show. I had some cool smart people around me, and so I was giving them interviews that I was doing and I was working on questions with them and I was just trying to get their feedback.

I incorporated this hack into the show for the first five episodes, but it happened right when the show … Right when it happened in our conversation, all of a sudden I’d put in a rewind sound and we’d replay it and I’d be like, “Oh, and that’s the hack,” and then keeping going. People were like, “That’s really cool.” I was like, all of a sudden I was jostled into paying attention again, but then I stopped paying attention, because it was like, “Well, that was the best part of the show. Why do I … ” I was like, “Oh, interesting, interesting. Okay, we got to move this to the end.”

It was, to me, which is all I had ever done up til then was really create software, so it was iterative sort of process. It’s like, “I got to create a really, really crappy version and I’m going to hand it out to friends that I trust.” Not friends that’ll just tell me that it’s good, but they’re going to tell me feedback and things and tell me questions that could be better, because I’d never interviewed anybody, so I needed to work on this. It was just this process and then some time mid to late July, one of my good friends in Australia came up with the idea called Hack the Entrepreneur and I was like … Looked it up and it was actually available as a domain so I bought it instantly because I was like, “Wow, for ten dollars that’s a pretty good domain, but I really don’t like hacks.” Then I was like, “But it works with this hack thing that I’m trying to create.” That was sort of the evolution of it.

The whole basis for the show, Brian, was that all of the shows that existed until then, so I didn’t go to the whole niche down, like, Entrepreneurship, right? It’s the big sort of business section. I didn’t try and niche down from there to something small, I was like, “No, screw that. If I’m going to do this, I’m going to go big.” I looked for a gap, and everything that I found then and everything that I listened to was very tactical, was very much, How to do this. Here’s the seven steps to this. And you’d have an expert on and you’d talk about how to do … It wasn’t Facebook ads at the time, but whatever it was at the time, right? SEO or something.

I was like, “That’s really, really cool and super, super absolutely useful,” but mindset to me is like the big thing, that’s the … There was this correlation I found with all the people I knew around me doing stuff in business where they just had this different way of perceiving the world. I was like, “That’s the gap in the market. That doesn’t exist, for some reason, in the marketplace.” I didn’t talk tactics at all. We teach through just showing the mindset, showing how people think. I still start my episode, tell people before they’re on, it’s like, “There’s no right or wrong answers. There’s no seven steps to anything. When I ask you a question and you don’t know the answer to it, say you don’t know the answer, and then let’s kind of work through that, because we need … Other people need to know that we don’t have all of the answers all of the time, but the job of us as entrepreneurs is to just continually be learning and growing and trying to stay just far enough ahead of our companies.”

That was the gap. I knew, again, like creating any product, is you just have to find a gap in the marketplace. To me, that was the gap. That gap has now been filled and now there’s 50 other podcasts behind me like that, but at the time that’s what it was. Every market has gaps, always, but

Knowing When to Reveal the Hack

Brian Clark: All right, all right, all right Jon. Now if this were your show, you just revealed the hack right up front and now I’ve got to convince people to keep listening. That was it. I mean, I always tell people, “Look, you don’t want to find … You don’t want to go niche. You don’t want to find something that no one else is talking about. No, you want to go in where there’s tons of competition because you know there’s an audience there and then you want to position yourself in the gap.” That’s it. And you just explained how that came to you. Let’s drill down a little bit, because … Everyone keep listening, dang it.

Jon Nastor: Sorry, sorry.

Brian Clark: What’s interesting, to me, is you weren’t just sitting there in some abstract looking out the window creative mode going, “Hmm? I think I’ll call it Hack the Entrepreneur, and this, and this, and this.” No, you were doing, you were researching, you were bouncing off ideas, and it revealed itself. I cannot stress, that’s how it happens all the time. Roll your sleeves up, dig in, you don’t know what it’s going to be, you don’t know where you’re going to find it, but that’s how you find it. It’s not staring out the window.

Jon Nastor: Right, exactly. It’s I think also taking things as they come, but with imperfections maybe? Like, Hack the Entrepreneur I did not like as a name. I just need to stress that. I had a hard time, at first, being able to get my head around having it … Because I don’t like

Brian Clark: The hack thing annoys me too, but it resonates with people.

Jon Nastor: Exactly, so

Brian Clark: You’ve got to go with it.

Jon Nastor: I know, and to find a dot com that has entrepreneur in it, you know what I mean? I had to, at the beginning, convince myself that, It’s not exactly perfect, but I can get behind this fully. This is cool, all right, let’s go for it. Then the other thing was that once I found the gap I wanted to fill by you’re right, doing a ton of research, listening to way too many podcasts, I 100% completely never listened to another podcast until, I’m going to say, like mid November of that year, because I was in … This is the same way I’ve created anything. If I’m creating a product in any market, I need to know what’s out there, I need to know what’s good, what’s bad, but as soon as it’s time for me, personally, to start creating it, I cannot look at other stuff anymore.

One thing, because I know that as soon as I’ll create an episode or I’ll put in the new music and then I’ll go listen to another one and be like, “Oh, they got so much cooler, maybe I should change mine.” Then it’s like, “Okay, maybe I’ll launch in October, maybe I’ll launch in November, maybe …” It’s like, “No man, just …” I had to trust myself that I had taken in enough stuff, I’d found my gap, and now I have to trust my instinct to market, to create a product, and that I’m at least smart enough and slightly unique enough that people might dig this. I just went for it, and I literally did not listen to anything again and then I actually launched on September 5th, like I said I would.

Brian Clark: I’m the same way. I mean, I dig into everything. I look at everyone. I was thinking, in your case, there’s these shows out there like Entrepreneur on Fire and Smart Passive Income, these guys who started early. I mean, you’re really doing something similar and yet you’re not. I mean, this is definitely Jon’s show, just like … Or your Jon, J-O-N, not J-O-H-N.

Jon Nastor: That was close. John Lee Dumas and Pat Flynn were both at that conference.

Brian Clark: Oh, really?

Jon Nastor: They were two guys that sat across from me and they were like, “Dude, you have to start a podcast.” I’m like, “That’s because you guys are really good podcasters.” They’re like, “No, we weren’t good podcasters. We started two years ago, yes, but you have to.” Pat Flynn actually bought this gear that I’m actually speaking on, so it was kind of like, “Okay, okay, I’ll do it, I’ll do it.” Then it took me three months to get my head around it.

Brian Clark: Yeah, well that’s not too bad. I mean, for a run-up period, that’s … Three months is acceptable.

Jon Nastor: I kind of stopped thinking about it, but I just I was there, and it’s like, the gear was here, and it was kind of like, “It’s going to happen at some point,” but then all of a sudden it was July, that was it. I was like, “This is my summer and I’m launching September 5th.” Yeah, I mean I have to thank those two dudes, they were the guys sitting across the table with 18 other people.

Keeping on Track, and Persevering

Brian Clark: Interesting. All right, well let’s talk about something that relates to the catchphrase for this show, which is keep going. It’s so crucial, as we were disgusting. Disgusting? Nice … Discussing before the show … Unemployable, after a year and a half, is just now getting what I consider some traction and you started Hack the Entrepreneur I think a full year before me, is that right?

Jon Nastor: Yeah, I believe September 5th, 2014.

Brian Clark: Yeah.

Jon Nastor: Two and a half years ago, almost.

Brian Clark: It does take some time and I think people need to understand that. I don’t care if you have an audience to start with or not, when you do something new, it’s a new thing and you don’t know exactly how people are going to respond and at what speed. For podcasting for sure, you’ve got to put the time in. I can remember us having a conversation. It may have been six months ago. You were in this space where, I don’t know what I’m doing next, kind of thing, and we had a couple conversations and I said, “Jon, you are doing your next thing. Keep doing it, right? Where did that come from for you, were you restless or were you not sure that Hack was going to be the thing?

Jon Nastor: I am restless, that thing is still sort of there. Your voice is still in the back of my head keeping me patient. This is … I don’t know, Brian, I think this comes from the fact that I come from software and product, and to me, that was a tangible sort of thing I was creating and enjoying, and now I don’t have that. Now it’s … All of it’s based on me and me talking. Sometimes I have a hard time perceiving that as a product, or as a business. Although, it fully is and completely pays for my family.

It’s something that I so didn’t plan on doing. I mean, it’s that whole, None of this made sense going forward, and looking back it’s like … It makes sense where I am now, totally, but I never would have planned this. There’s no way I ever could have, it’s the way it went. Sometimes I struggle with that, because of it’s uncomfortable for me, the position that I’ve put myself into. Which is a good thing usually, but it is a thing and now … Yeah, I don’t know, maybe I need to create more stuff.

Brian Clark: No, I get it. Sometimes it’s hard to accept that you’re having fun and getting paid, you know what I mean?

Jon Nastor: It’s crazy, it doesn’t even make sense.

Brian Clark: To be you, because as you mentioned earlier, these are the things you would ask these people anyway. Yet, you just hit record. I mean, there’s more to it than that. You’re a great interviewer, and that takes practice, it takes skill, it takes preparation. But still, if you’re curious in what the guest is about and their experience then you’re just having a good time.

Jon Nastor: Yeah, no exactly. I’m fascinated by every single conversation I get to have. I would have it absolutely for free. I would pay for the beer most of the times if that’s what it took, but instead I just get to hit record and put it out to a lot of people that listen to it. Which also, if I can’t think about that every single time, otherwise it’s hard. If every goofy thing I say on my show, I think that it’s going to be listened to by 100,000 people, it’s hard for me so I tend to not do that.

Brian Clark: That’s funny, because I’ll say something, or tweet something, or just something stupid that I think is the end of the world and no one cares. You know what I mean?

Jon Nastor: Yeah, I know.

Brian Clark: It’s not a big deal, we’re just so harsh on ourselves from a self criticism standpoint.

Jon Nastor: Right, I agree.

Brian Clark: Okay, so if your sponsorship page is current you’re up to over 20,000 downloads per episode, right?

Jon Nastor: Yes.

Brian Clark: That’s nice. Ball parking it, and we can … I want to dive into this a bit, because I think there’s a lot of mystery to a lot of people about how podcasts make money, how to deal with sponsors, all that good stuff. Maybe this is how we’ll keep people listening after you revealed the hack too early.

Jon Nastor: I’m terrible at this.

Getting Paid

Brian Clark: No, but so for 20,000 downloads we’re looking at a sponsorship rate of about 1,000 bucks, right? For say the standard 15 second pre-roll with a 60 second mid-roll. Let’s define for people … If I’m wrong, tell me, but let’s define this for people so they understand what we’re talking about here. How do you get paid with these sponsorships?

Jon Nastor: I get paid in advance, first of all. I never do any of it, I don’t even write copy until I’ve been paid in advance for all episodes on the contract. This has been a real sort of fluid evolution with me. I joined about 14 months ago, 15 months ago I joined a company called Midroll. They run sponsorships for companies, or for podcasts, they’re like the intermediary. In the end of November, so just a couple of months ago, I left them. I’m in a real transition sort of phase of taking back control and having more of a direct relationship with my sponsors. It’s a lot different now, it’s more like it was in the beginning, except I have a much larger audience, so I can control things better. I’d lost control is the easiest way to say it and the nicest way to say it, in case you’re listening, Midroll, that’s where I’ll keep it at. I’m in more control now and I’m unemployable, right? I’m kind of a control freak in that way and so I like it.

Now the idea is, right now, as of right before Christmas when I went on the holidays, I took a week off, I was like, “Okay, this is my first time in almost two years that I’m fully in control of my own sponsorships.” I reached out to three companies and I landed three sponsorships and I sold out every episode until the end of March. Then, as of yesterday, actually I sold out into May. Those are all paid in advance. Those are companies that I fully 100% use and endorse. I’ve switched from having a pre-roll and a mid-roll that are different companies, because I think it just messes up the whole thing for my audience and for me.

Now one person sponsors every episode. They do, they get … I don’t really push 15 seconds or 60 seconds, whatever it is, there’s kind of a warm up sort of one at the beginning, which is the pre-roll, just kind of says the URL and tells them about the company really quickly, but leads into sort of the story based main mid-roll. Then that can run anywhere from 40 seconds to two minutes. For the same sponsor, but because I only let people buy a minimum of ten episodes now, that’s just how

Brian Clark: Oh, really? Interesting.

Jon Nastor: Yeah, it’s too much work, Brian, to write copy and stuff for people, like no …

Brian Clark: No, I know. Let me tell you my experience and I know FreshBooks sponsors your show, so they reached out to me and I’m like, “Okay.” I understood generally what the industry CPMs were and it’s really funny, because I negotiated that deal before I got this spike in subscribers from being mentioned in Inc. Magazine. They got a great deal, but here’s something smart. I guaranteed them that … They did nine episodes, okay so the first month I gave them 7,000 downloads, which is what it was at that time, minimum. Then of course now it’s at 14 or 15. Month two and three, or three through nine episodes, I can make up for actual downloads that are actually delivered. Do you have that sort of caveat in your deals, or do you just say, “You’re buying this many downloads and if it’s more than that, then great?”

Jon Nastor: We actually don’t even talk downloads that much, interestingly enough. I don’t know

Brian Clark: Wow, okay.

Jon Nastor: If it’s because I’ve been around a long time. I don’t work on CPM.

Brian Clark: Oh, okay. That’s cool.

How CPM Works

Brian Clark: Let’s back up and explain how CPM works, because we’re talking past some people, I think, right now. Then talk about how you do it.

Jon Nastor: CPM is cost per thousand, right? Per thousand downloads and that thousand is based on six weeks from the date you publish, six weeks out is the industry standard. However many thousand downloads you have in that six week period, then you get paid. Right now I think a mid-roll, they go from anywhere from 15 dollars up to 35 dollars per CPM, so per thousand. Meaning, if I get 10,000 downloads and my CPM is 25 dollars, I’m going to get what? 250 dollars is that? Or 25- I don’t know, I’m terrible at math too.

Brian Clark: Yeah, here’s how I figure it out, because usually … Well, if you’re selling the pre-roll and the mid-roll together, which I think is a good policy, you want that consistency. Roughly, and this, you can set your own prices, but this is just kind of the industry rule of thumb. Multiply 43 times, if you have 10,000 downloads, then times ten, and that is the cost for those two spots in that episode. The actual … The pre-roll and the mid-roll are priced differently. I think it’s 18 versus 25, but that’s just a rule of thumb if they’re grouped together. 43 times per thousand, right? If you have 10,000 it’s ten.

Jon Nastor: Exactly. When I was running through a company, Midroll, the company, it was 100% CPM all the time and I kind of didn’t like it. I’m really into having a partnership with a company that I’m dealing with. I think it’s more effective for me, I think it’s better for my audience, and I think it’s better for the company. The numbers are there, we know the numbers are there, but after that it’s really, we’re trying to create kind of a good, unique, experience that works really well. Meaning, that we don’t have to have that really hard call to action in that first 15 seconds or whatever it is, and everything can kind of flow. It gets me a good offer from the company with a unique landing page so that it shows that this is unique and this isn’t the same one you’re going to get everywhere else, which makes people take more action and it makes people not tune out during those.

Then you can offer things like links into the show notes, obviously, links into your newsletter if you want, which I have never done the newsletter part of it, but I have put … FreshBooks actually right now is in my sidebar of my site and that’s part of just the partnership package that they’ve taken. They bought them for 15 episodes starting yesterday, actually, they started. To me, it’s too, I don’t know, it’s what I wanted to get out of. I wanted to get back to having those partnerships with those companies. I also like to … I’ve lowered my rates a bit right now, just because I wanted to fill them up and prove to myself that I still could, because I’ve been dealing with another company for so long. I didn’t want to just be running without sponsorships and it sold way faster than I expected.

Brian Clark: Without getting too much into your business, would you say you’re charging more or less than that general CPM rule of thumb?

Jon Nastor: Right now I’m charging less.

Brian Clark: Okay.

Jon Nastor: If I was charging per episode, I would be charging what you’re saying or more. Actually, that’s part of my pitch. I show my regular rate, and then I say, “At ten it drops to this. At 15 it drops to this.”

Brian Clark: Nice.

Jon Nastor: That’s just because I get to use basically the same copy. I record new versions, but we work together on the copy quickly and then it’s on a Google Doc. They can change stuff as we go live with different episodes if they want. It’s easier for me, and I feel good doing it, so I feel that it helps … I feel like I was really losing parts of my audience or engagement when it was two wacky sponsors, one in the beginning, one in the end. One’s a mattress one, one’s like … It was total nonsense and I didn’t like it and I should have stopped it probably sooner, but I didn’t. Now I’m getting back to where I want to be and I’m going to take a slight financial hit in the short term for that.

How to Be Smart about Your Income

Brian Clark: Yeah, but I think that’s smart. The idea that a lot of people seem to miss is that you shouldn’t be trying to milk everyone for every cent. You’re trying to establish a long term relationship. That’s more valuable than the exact dollar amount you make this episode, right? Yet, I see a lot of people who have that mindset and I don’t think it’s conducive to succeeding.

Jon Nastor: Oh, yeah. I would way rather have the rate I have right now and have these three people sign on next quarter, and next quarter, and next quarter, because I like it, I think it’s better for my audience, I think it’s better for everything, and it’s less work. It’s easier and I get to build that relationship. I just moved to Toronto where FreshBooks is based out of. I mean, when I first got here it’s like they invited me and I spent the afternoon in their office and that’s pretty cool.

Brian Clark: Yeah.

Jon Nastor: To me, that’s pretty cool, that’s a good relationship to have.

Brian Clark: Right now FreshBooks is getting free exposure.

Jon Nastor: Exactly. They have been for years, they were my first sponsor ever-

Brian Clark: Mine too.

Jon Nastor: When the show was hardly anything, that’s just how it is.

Brian Clark: Yeah. Okay, let me ask you this. Do you experiment at all … See, I would never do the Midroll thing, no offense. I mean, I thought about it and I heard about it, but I think going into it I would feel wary of the very experience that you ended up having, right? Because you almost think, That’s got to be the way it is. You know? I don’t think anyone’s ever dealt with a company like that and said, “This is fantastic.”

Jon Nastor: I did it for a different reason. I did it to potentially help my show grow and I think it did in the short term. Meaning that, it’s really hard to get onto Midroll.

Brian Clark: Oh, is it?

Jon Nastor: They have it right clearly on their site that you have to have 50,000 downloads or more per episode, which I didn’t have. They had reached out to me, so I launched in September, at Christmas time they reached out to me. I didn’t even know who they were, but as soon as I went to their site it was like, “Wow, they have John Lee Dumas, they have Tim Ferris, and they had Hundred Dollar MBA. That was like three shows I totally admire and then me … I actually turned them down. I said, “No, that’s cool. Thank you so much, but I’ve got it under control,” and I had just sold FreshBooks for months in advance. They said, “Cool, if you ever change your mind, come back.”

In June of the following year I did change my mind. I said, “Let’s have the conversation. Let’s see where it can go,” because I had been talking to podcasters at this point. I wasn’t a podcaster, I didn’t think, until then where I kind of entered the market. Talking to a lot of people and Midroll kept coming up and it was like kind of this elite weird thing where people were like, “Yeah, those shows are doing so amazing. They’re … ” I was like, “Man, I could just be on Midroll. That’s kind of cool.” I approached them, we had big long conversations, it took about two months to sort out, and then I got on there. Then I was just flooded with people emailing me like, “Man, can you get me on Midroll? Can you get me on Midroll?” It helped in that way.

Brian Clark: Oh, okay.

Jon Nastor: Completely indirect from how they’re supposed to help me, but that is 100% why I did it. Then after that I just stuck with it too long.

The Potential Benefits of Affiliate Sponsors

Brian Clark: Got you. Okay, so have you experimented at all with affiliate sponsors? The reason I think that may be interesting, as you well know, a sponsor gets the benefit of being in that episode forever and we know that listenership goes way down after six weeks, but people still listen to my old shows, right? As a content marketer, that’s great, we were promoting our own stuff. But what about an affiliate, a perfectly matched affiliate offer to what the topic is and you get the benefit of the fact that that’s out there forever and could be earning you some residual income while a traditional sponsor wouldn’t?

Jon Nastor: Yeah, it’s a really smart idea and the only times that I’ve done affiliate sponsorships, or like ads, is when I didn’t sell the spot. There was quite a few second quarter of last year and then early third quarter. For some reason Midroll just was struggling to sell spots and so I just filled it up with different spots. They kind of work, but they kind of don’t really that well. That’s not to say that the idea of affiliates doesn’t work, it’s just I didn’t target it right, or I didn’t read the spots right, or whatever that happens to be. Right now, Brian, the way I think about it is, it’s like I mean, what am I going to do? Am I going to cancel somebodies sponsorship that they prepaid me for?

Brian Clark: Oh no, it would only be in the event that you didn’t have a spot filled.

Jon Nastor: Oh, 100%.

Brian Clark: Yeah.

Jon Nastor: When I quit Midroll in November, that’s all I said. I was like, “I’m going to quit Midroll and for the first quarter I will probably have to run affiliates and I’ll have to find some cool companies and run that.” Totally cool. I was totally happy with that. Instead, I just went out on a sales pitch for a week and I sold all three month s worth. I didn’t have to do it, but I definitely would have done it and I think if I was starting over and didn’t have a way to get sponsors right away, that’s definitely how I would do it. Because I think that shows should have ad spots.

I think shows should have an ad spot before you get a sponsor, you should be running a thing that sounds like an ad spot, but is an affiliate because it gets people used to it and that’s another whole level of making your show seem more professional. If I listen to Tim Ferris and I listen to Pat Flynn and they have ad spots and now I listen to Jon Nastor and he doesn’t have ad spots, it’s like, “Oh, this guy is totally just a rookie, he … ” All of a sudden you’re on a different level, so you should be running those affiliates. I’m lucky enough that I fill up all the time whenever I try, so …

Brian Clark: See, good thing you stuck with it.

Jon Nastor: Exactly, yeah. I mean, I guess sales don’t bother me, I enjoy sales, so actually-

Tips For the Sales Process

Brian Clark: Yeah, tell us a little bit about that because I’ll write copy all day long and close people that way, but getting me to write an email cold reaching out to someone, I’m just … All of a sudden I lose my nerve. Tell us a little bit about that process. How do you go about selecting companies, approaching them? It seems that it s been successful, you are three of three.

Jon Nastor: Yeah, for sure. I’m terrible at writing copy. I can pick up the phone and phone somebody and I feel like I’m really good at making a sale. I kind of enjoy it and I’ve … When I did it right before Christmas, I actually after that one week I said to my wife, I was like, “Man, I really missed that. I really miss just hustling and getting on the phone with people and just closing them. It was awesome.” It really is … I mean, to find the sponsors, it’s easy. You know, you’ve already found the gap of the market you’re going to hit, you find the gap in between other shows. Look at those other shows and look at their sponsor pages. Who’s sponsoring them? Reach out to those people. There, that’s pretty easy. You just literally reach out, tell them about your show quickly and ask them if they’d like to talk on the phone. Then they get on the phone with you, and now think about it, you are making a pitch.

This is where most people, I think, fail. They don’t want to feel like they’re selling. You are selling something. These people have to buy what you are selling. You’re selling them the ability to connect with your audience who will buy a ton of their stuff. That’s huge, right? Don’t undervalue that and make it like a sales. Not like a sales pitch in that way, but you are selling, you have to close these people. When you send them then … Follow it up with say, an email that sells them everything you said, everything they’re going to get, what they’re going to pay, make it look good. I go on Canva. It takes me 15 minutes, but I go on Canva, I brand it with my show, put some cool colors in there, some graphics, make it look like, “Holy dammit, this thing looks pretty damn pro. Yes, of course I’ll sign for that.” Perfect.

Brian Clark: Excellent.

Jon Nastor: I see what some people do for pitches, it’s like, “Dude, what are you doing? You wouldn’t buy this.” They’re like, “Well, they’re just buying the spots.” They’re not just buying the spots; they’re buying a partnership with you and your audience. You have to know that and you have to sell that to them, because that’s what they’re buying.

Brian Clark: Excellent. That’s good advice. I hope people stuck around after you, you know, did the reveal too early.

Jon Nastor: I’m never going to live that down.

Brian Clark: I’m going to harp on this, like every time I talk to you, see you, anything, I’m going to be like, “Thanks Nastor, way to go.” No, no, this was good stuff. Well, I’m glad you’re rolling with it. It’s a great show, it’s turning into a great business. I think, as you’ve seen with other podcasters, sponsors are just the beginning. There’s so much more you can do with your own products, and I know you wrote a book already, we didn’t even get to that. You can launch courses, all of that. I think we’ll just visit with you again in a year or so and see how the empire is doing.

Jon Nastor: I love it. Thank you so much, it’s been a blast.

Brian Clark: Yeah, thanks Jon so much. All right everyone, if you’re thinking of starting a podcast this is a great way to get started. It’s not too late, find your gap, serve your audience, and stick with it. You know what I’m about to say: keep going.

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