026: From Side Hustle to Award Winning Podcast with Nick Loper

Share with a friend!

026: From Side Hustle to Award Winning Podcast with Nick Loper

00:00 / 40:55

On this episode I’m talking to Nick Loper from Side Hustle Nation and The Side Hustle Show. Nick has published over 220 episodes over the past 4 years and his podcast has received millions of downloads in that time.

[podcast_motor_player url=”https://episodes.seriouslysimplepodcasting.com/PodcastMotorShow/026_-From-Side-Hustle-to-Award-Winning-Podcast-with-Nick-Loper.mp3″ title=”026: From Side Hustle to Award Winning Podcast with Nick Loper”]

He has used podcasting as a content marketing tool for several years and created an engaged community around his podcast niche.

Join us as we discuss the business of producing and growing a consistently successful podcast.

Topics Discussed in this Episode:

  • Evolving The Side Hustle Show content over time
  • Podcasting as a content marketing tool
  • Creating content lead magnets for each episode
  • Adding a Facebook group to your podcast community
  • Metrics and production of Side Hustle Nation
  • Nick’s process and recommended content marketing tools
  • Podcast conferences and industry networking
  • Challenges to long-lasting success as a podcaster
  • Experiences getting sponsorship


Side Hustle Nation

The Side Hustle Show

Lead Pages

Podcast Hackers Facebook Group

Craig: This week, I have a really special guest on the show. I’m really excited to have Nick Loper from Side Hustle Nation and The Side Hustle Show.

Nick, how are you doing?

Nick: Doing excellent, Craig. Thanks for having me.

Craig: It’s my pleasure. It’s embarrassing when I think about how long I’ve been listening to business and entrepreneurial related podcasts because for a long time I was a dreaded entrepreneur and just listen to a bunch of podcast and thought into a bunch of stuff before got my toes in the water. But yours has been one I’ve been following maybe for all the four years that you’ve been podcasting. It’s great to finally catch up.

Nick: Wow. That’s crazy. You’re there from the very early days, probably one of the very few people from those early days.

Craig: Definitely within the first year. It’s so cool to see the arc that a show like yours takes after 220 something episodes. I think that you’re definitely the first one on the PodcastMotor Show here that we’ve had that has so many episodes.

I guess to not dig right into it, can you give folks an idea of who you are and what your podcast is all about before we dig in?

Nick: Somewhat stubbornly persistent apparently who wouldn’t even make it through those early years of the Libsyn chart, being pretty low.

I’m Nick. I run the Side Hustle Show podcast. It’s become my main focus over the last few years. The show and even the sidehustlenation.com site really started as a side project to the main business that I was running at that time which is a footwear comparison shopping site. That started as a side hustle, it’s helped to my main corporate job. It’s been a lot of years in the making or in the entrepreneurial journey but what I’m doing today would be unrecognizable too to the me of five years ago. It’s like a constant evolution but it’s been a blast doing the show.

Craig: Speaking of the evolution, I think there’s a certain amount of staying true to yourself that you have to stay disciplined too when your show is evolving and you’re letting it evolve over time. Have you run into that either personally or with listeners saying, “Hey Nick, what happened man? You used to be over here and now you’re over there. You are losing me. Has your compass had to be recalibrated at all as you evolved?

Nick: I just this took this annual member survey and had 1,200 responses and found of those, 40% where in entrepreneur category. They haven’t started anything yet and another 20% had started something but were still in startup terms pre-revenue. That was eye opening to me because it’s like, “What have you guys been doing for 200 episodes. Just pick one thing and go to town. 12 months later you might be working on something completely different.” But that just momentum and motivation of starting anything, putting this stuff into action all of a sudden, the light bulb start to go off and you start to see these different ideas. That was really surprising to me so I don’t want to be producing only beginner level content because there is this segment of the population that is already making money in the segment that’s already even full time entrepreneurs.

It’s good see to see like, what are people working on? Where are they at today? Even in the criticisms. What would you change or what would you like to hear me cover a little bit more?

Craig: Not to give away the inside scoop on your survey but in that feedback was the content feedback geared that do you want to hear more advanced things or were you spot on with the level of advancement of your content?

Nick: That probably correlated pretty closely to where people are at, the people who are already making $1000 to $5000 a month and more. They’re like, “Let’s learn more higher level marketing stuff.” And other people were like, “I just need to figure out what idea to start. How do I focus? How do I use my time to actually get something done?” There’s a mix for all of that and try to find that balance is probably a constant challenge like we did.

The Amazon FBA Business Models are probably the hottest side hustle going right now and has been probably for the last couple of years. We’ve got several episodes talking about that. For the people who are interested in it, fantastic! But some people are like, “I just skip those because I don’t care.” I was like, that’s fine. It’s like on demand choose your own adventure kind of thing.

Craig: What is about the stick-to-itiveness that is so hard for a lot of entrepreneurs? Myself included, I may have Shiny Object Syndrome worse than most people I know and fortunately, I’ve been able to stay focused on PodcastMotor as my main business pretty since it started. I’ve strayed a little here and there but I’ve stayed true to it. I think because we had some success early so I was beholding to our customers and to the people that worked on our team. I think that was part of me being able to stick with it. You’ve done 200 plus episodes with successful entrepreneurs who have mastered the side hustle to some degree. What have you seen that’s like a common trait with the successful entrepreneurs that are able to stick with it like you said for 12 months and make something happen?

Nick: I think the common thing is starting anything and not being married to that idea like my lifelong passion or goal? My friend Julie puts it this way, your first steps as an entrepreneur really like the first move in a game of chess. You’re going to move your pawn out into the world and just see what kind of reaction it gets. Probably chess players are like, of course it matters which pawn you move. I don’t know enough about the game. That’s your first step, it’s not your commitment, you’re not going to get checkmate on the first move but it’s just like this one tiny baby step, it doesn’t really matter. It’s all about trying to figure out what reaction that it gets.

In the case of hosting the show, I positioned it in my mind as an experiment. Hosting was $15 a month. Had it been $25, $30, the show might not even exist because I was like, what am I signing myself for? I don’t want to commit to being this extra server fee. I had no idea how it even worked. It was just like even seeing a little bit of momentum, a little bit of positive feedback in first episodes are horrible. Those are the ones, I emailed everybody I knew, like download this, leave me a review. They’re horrible. I’m super embarrassed by them now.

Over time, it’s become my art. It’s sounds cheesy but this is the highlight of my week, putting together the show and try to do the intros and outros and stuff. It’s like Cal Newport, too good to ignore, I forgot the title of his book. It’s stressful, I don’t know if I have an undying passion. Start a business around your passion, his argument is like, “No. The passion comes from the continuous practice and it’s a journey to mastery.” I found that to be true. I think a lot of people that have the honor to have a show have found that to be the same way. Like if you have a podcast editing business, it’s like you just start out not having this major passion for it but I imagine you learn different tricks and you improve you trade over time and it becomes something that you’re passionate about.

Craig: Yeah. I think for sure that you can start out being passionate about whatever your business is, podcast editing or running your podcast or whatever but in the end, for me at least and for a lot of people I know that runs big successful businesses, it’s not about a time tracking app, or podcast editing service, or running a successful podcast itself, it’s about the business and the goals and the creative process around the higher level stuff.

I think you’re spot on, at the beginning, the best way to make sure you stick with it at least for that first iteration, that first version of what your business is going to be is have some success. Because if you don’t have any, that’s super easy. Just be like, “Let’s do something else and go chase that other shiny object.”

Nick: If I can get people to that first dollar, whether it’s just flipping some item from a garage sale, or selling something out of your own garage, or just landing that first customer, even selling your first gig on Fiverr. If I can get people to that first dollar of job free income, of side hustle income, then the light bulb start to go off and it hooked and that’s what I want people to feel, that rush. I am more than what it says on my business card. I have worth to this outside world. I can make money outside of just my 9:00AM to 5:00PM and then hopefully we can scale that from there.

Craig: Yeah. The Side Hustle show is obviously very successful, top of the marketing funnel, if you will. Potential customer acquisition and everything but how does it fit in with everything else you do around community building and interacting with your listeners for your overall brand?

Nick: Surprisingly, to me, I thought of myself as a writer first but it’s probably been the number one avenue of discovery, the number one growth driver for Side Hustle Nation. The inflection point of the show is a little over a year deep into it, I realized like, “Look, this is never going to be entrepreneur on fire. This is never going to make thousands and thousands of dollars from sponsorship money. It’s not going to be a stand-alone business.”

Once I recognized this is just a content marketing arm and started behaving as such, that’s when things started to take off and the specific tactic that really worked for me was producing an episode specific lead magnet or opt in offer based on the content of that episode. It’s like okay, we just talked about how to sell courses on U2Me even if you’re not an expert. If you want Scott’s top tips for everything we’ve talked about during the show, you can go to sidehustlenation.com/scott or whatever episode number is. That’s how I had an email list of probably 1,000 or close to it. Within 3 months it’s 3000, within 6 months it’s 6000. I really accelerated the growth of everything. It has continued to work pretty well.

That’s the problem with podcasting, it was such an anonymous medium. You told me you’ve been listening since almost the early days but I know I’ve seen your name around but this is the first time that we’ve been talking. It’s hard to gate a gauge on who’s on the other end of the mic because it’s just like the production process is me in my living room and it has been the same since day one, whether that’s going out to 10 people or to a 1,000.

Getting people in the email list has been years because then you can send people back to your website or back into you, what we set up is the Facebook group actually came out of the member survey from a couple of years ago. Would this be valuable? I don’t want to set myself up to be moderating spam and do all those stuff.

The Facebook group has turned into a pretty cool community. People supporting each other and answering questions without my direct involvement in a lot of the threads and I do like to spend some time in there because it’s cool to interact with people and see what everybody’s working on.

Craig: The community building aspect is huge. We had a guest on a couple of episodes ago that was in the gardening niche and talked about Facebook groups and how she leveraged her business on Facebook groups as her main community building and engagement. Yes, it was a fantastic interview but I think it’s the secret for building a really engaged following because email is great and it’s easy as a business owner or somebody who runs a podcast or whatever content marketing you’re doing. Email is easy because you feel like, okay, I’m going to send this email and everyone is going to read it. The reality is, if you’re really good, I don’t know, Nick, 30% of the people actually read your email.

Nick: I’ll aim for 30% open rate. I’m happy with the 30% open rate. How about that?

Craig: We get done on some emails and a Facebook group post I think will get real engagement of 50 %. They’ll see it many more than 50%. We’ll see it but 50% will see it and think about and click on your link or whatever. I think it’s fantastic. We have Facebook group for Podcast Motor. We’re not quite as community engaged in there. I’m the one spurring some of the engagements here a handful of months into starting the season organic dialogue that you’re talking about, I think that’s where the community takes off.

Nick: It’s a long time coming, so I always said hey this is the community for part time entrepreneurs but there was no interaction. I’ll tell them, commenting on the blog there was no interaction amongst the community until finally putting that group together. So it’s like, “Whoa, should I have started it earlier? Would it have been a ghost town?” I don’t know since I was trying to find the balance.

Craig: What do you think really kicked the Facebook group off successfully because I think even with a good following like you have, you can build a Facebook group and then it’s crickets in there as well. What did you do when you launched the Facebook group for it to be successful and have that organic dialogue?

Nick: What I’m trying to do at the beginning was like, and I still trying to do it today is like seed conversations. For example this week, I say I’m going to experiment with this theme day productivity system. Tuesdays is meeting day, Monday is finalizing the content production day, finalizing this week’s podcasts and doing some writing. Wednesday, I’m working on my various Side Hustle projects and some administrative stuff. On Thursdays, is for the longer term, growth and strategic stuff, strategic projects and that generated a pretty decent conversation. Do you guys do something similar? Have you tried this? How did it work? We got a good conversation going there but like what are you working on this week? Sharing your wins on Fridays kind of a tradition inside the group. A lot of people now are asking about, hey I’m a student, I’m 17 years old and I play two sports. What kind of Side Hustle should I be working on? It’s interesting to hear what people are coming up with.

Craig: Interesting. That’s great. I think that’s testament to people being so passionate about following what you’re putting out on the podcast and then taking that conversation over to Facebook, which is as a content creator, the ultimate goal.

Nick: That’s right. I guess more touch point but less sales-y touch points, if that’s a thing. The more they can interact with your brand and have a positive, helpful experience. It’s like the jab-jab-right hook stuff. Try to get in front of people but do it in a non-sales-y way.

Craig: Sure. For folks who aren’t familiar with your show, can you give an idea of where the show is in terms of downloads and some statistics that people can give a sense for. I know you are a finalist two years in a row for best business podcast award. Can you give us some framework of where the show stands these days?

Nick: That’s right. I lost to Start Up and I lost to Smart Passive Income. I’m in pretty good company up there.

Craig: Not bad.

Nick: Almost four years deep into the show. 220 something episodes, new episodes are seeing around 20,000 to 30,000 downloads per show and 220,000 downloads a month and later this month we should cross the 3,000,000 mark in lifetime downloads which just over a year ago was at 1,000,000 so you can see that compounds over time.

Craig: People are going back in listening to 50 or 100 episodes, I guess.

Nick: That’s what is surprising. Episode one for example, it’s fine. It’s an okay episode. I’ve had an email list of 11 at the time that it launched and nobody heard it, probably had 20 downloads in the first month or something. Now it has 14,000. It’s like, okay, people are going back and binging on the archives which I think is a cool value ad for sponsors. Because they are looking at what are your numbers today, it’s like, let’s look at what if we fast forward two years again and see how many more people are going to be listening to this that you didn’t even bank on. Some of those other ones have become pretty valuable real estate and there is no monetization on there.

Craig: Right. Those are big download numbers, that’s really impressive and not surprising for anyone who can get to 200 plus episodes. I sure would think that your numbers would be something like that but I think 200 episode, it’s quite the achievement, I’m in awe. On my personal podcast, we have 86 episodes now and I feel like we’ve been beating the drum pretty hard.

Nick: Let me ask you, what kind of time you think goes into producing each of those 80 episodes? I imagine it was probably more at the beginning and maybe less today. What kind of time commitment does it take you to produce the audio?

Craig: It’s a co-host show. It’s me and my co-host almost every episode. It’s maybe one out of five, we’ll have a guest or something like that. When it’s just he and I, we’ve done 75 episodes together so we’re really good, we don’t have much editing at all. I like a very conversational style podcast anyhow. It’s just he and I talking about businesses, we’re roughly the same scale of business at this point. I talk about in multiples of like raw audio times. If we record for 45 minutes, it takes me an hour to do the whole thing.

Nick: On top of the 45?

Craig: Total. It’s 45 minutes of raw audio, it takes me an hour to put it all together.

Nick: That’s not bad.

Craig: But at this point we’re a well-oiled machine. I think that the tough one really is an interview show, like most of yours where you are talking somebody who’s not a veteran podcaster, a lot of the times. They don’t want have the gear, they don’t want to have the setup, they don’t know when not to talk over somebody and mute their microphone when they’re coughing and misspeaking a lot and stuff like that. For me and for our audio guys, that’s where they just go in and chop the hell out of an episode. Just because they have to make it sound good. But for Dave and I, we’re pretty good at it these days, in think.

Nick: I’m going back and forth with that. There was a segment but probably a pretty good stretch of episodes where it’s like, “Hey look, it’s a podcast, people say, uhm, it’s fine. Just roll the tape.” I’m going back after a conversation at Podcast Movement, I think was 2015 where it’s kind of the influx of the NPR crowd, of the heavily produced, really well edited shows. This is what we’re competing with in people’s ear buds and it sounds a million times better than anything that I’ve ever put out. It’s an eye opening or ear opening moment to be like wow, it’s time to step up the editing game a little bit and try to produce a tighter sounding show and thus taking some time and if we had some editing help lately to do it but still take the final pass myself, make sure like okay, this is going to be a tight listening experience.

Craig: I definitely think for anyone looking to start a podcast or up their game there is definitely a minimum threshold above which your podcast has to live, has to sound good, has to be even in both ear buds and the volume levels have to be normalized and if you can get there, then people won’t stop listening. But I think what you’re talking about is your upping your game to the part where you’re drawing people in because of the production value  of the show. Is that what you’re go list?

Nick: Trying to. One of the very first show that got even into podcasting and I was probably annoyed, I think I clicked the link from Twitter and was annoyed to find it was like audio and not a blog, was a Tropical MBA formerly the Lifestyle Business Podcast. Diane, Ian, and those guys have really done an awesome job in the last year and a half or so in stepping up their production game, where it’s like they’re fading in and out. They’re having multiple guests and multiple people on each show and they’re like sprinkling in their own thoughts and it started to become really well done. In the early days, they’re recording from some café in Vietnam and there’s a background noise and all these nonsense.

To your point about make sure it’s the same level in both ear buds, in the first 6 or 10 episodes, I didn’t know any better. I exported it as a stereo and people will be like, every time you stop talking, I can’t hear what the guest is saying. So bad. You make a real mistake when you’re new and starting out but figuring out how it all works is part of the fun.

Craig: I know for sure. I think people are pretty forgiving with podcasting and the nice thing about it is your continually putting out new content like you are doing in your survey, keep putting out content, talk to your audience and hear what they like and don’t like. And then you can adjust it from there. I think it goes to the point about the NPR style podcast is for the topics that you’re talking about or the topics that I’m talking about on my personal podcast.

I don’t “need” to sound like NPR because the people who listen to my show just want to hear what I’m doing and who listen to your show want to hear what you’re doing and the guest that you have on. I’ll say it’s more content driven than entertainment driven, like a startup or a serial.

Nick: Hopefully it gives me a little bit of a fast but some of the comments on the survey are like the audio quality sucks or one of the most common ones are like the intro, the voice over guy, they are like, I would’ve ripped my headphones out every time I hear this super cheesy voice over guy. It might be time to bid him farewell and redo the intro because we wouldn’t want to have anyone ripping off their ear buds.

Craig: Sure. Going back to a little bit of the content upgrade that’s specific for each episode and growing that email list, how did you start implementing that? I think it’s a fantastic idea that I don’t hear a lot. How did you start implementing that, at this point talking about your process and systems, what does that look like when you’re doing an episode?

Nick: You bet. The tech that’s being used to deliver it is Leadpages. You click on the link, it opens up a lead box form name and email and then they’re actually delivering the file as well, upload the PDF to the Leadpages and then they deliver the file and then that interfaces with AWeber, my email service provider and of course, it gets added to my list as well.

The advantage is if you’re already in the list, it sucks as a user experience thing to have to enter your email again, we’re trying to figure out how to make it so you don’t have to do that but they are able to just get the file and you’re not going to get extra email from AWeber or anything like that.

My process at the beginning was just summarizing the episode and if I did it after we recorded, if I didn’t have a meeting or another recording right afterwards, I could bang this out probably 1,000 to 1,200 words. Today, this is the most important stuff that we talked about. I already start each episode with outline so that give a little bit of structure to that file but just calling it the highlight reel, like here is the most important tactics and take aways that we covered.

Now I’ve got a writer in the UK who listens to the episode in advance and summarizes those shows for me. I go through them and do final edits and then upload it to Dropbox which triggers if this then that recipe to email my VA and it says hey, there’s a new highlight reel, ready for you to install on the website. She gets that and she can now do all of the Leadpages in WordPress integration on the show notes. I was excited when I figured out, like okay, you can use, if this then that recipe, when a new file hits this folder in Dropbox, it trigger this email and so that’s fun.

Craig: That’s great. That’s the driving the most of the new email sign ups on your site as opposed to the pop up or the main opt in widget on the side.

Nick: Some of these episodes have thousands of opt ins, I think the most popular one is over 6,000 opt ins just on one podcast episode. Some of them are duds, some of them are well, that wasn’t a super tactical nitty gritty episode. I don’t need to go download the summary of that if it’s a more high level stuff, but some of the words were, do we get in down at the weeds. Look, don’t take notes, we’ve already done it for you. You can just go here. Those ones tend to convert really well. I don’t have the exact numbers in front of me but I would guess easily 2/3 of the list has come through those lead magnets or those content upgrades rather than the site wide lead magnet offer.

Criag: That’s fantastic! We see really good conversions on our content upgrades on our blog post, PodcastMotor. The hardest part for me a little bit, is I’m sort of left brained. It’s tough to put something together that looks good. I think I can write the stuff or create the checklist or whatever but the tech of creating a nice looking downloadable PDF is a little bit difficult for me. We usually send some of our staff to grab a designer. I do use anything or is it just a straight PDF to download the content upgrade.

Nick: I definitely won’t claim that it looks good. It’s just a word doc saved as a PDF.

Craig: Got you. InVision as one of the tools that you can create some fancy looking stuff with but once somebody gets to that point, they want the nitty gritty details of what you talked about in the episode. Giving it to them in a straightforward manner is fine.

Before we started recording, we’re talking about Podcast Movement which is the big podcasting conference that sure it’s in LA in early summer. Is that right?

Nick: Yeah, I think it’s in August.

Craig: I’m not able to go but you’re definitely going from what I understand. Talk about what Podcast Movement is all about? Why are you going? What you get out of going?

Nick: For me, at this point, it’s become a little bit of a family reunion amongst internet friends as my wife calls them. Go and have fun hanging out with your internet friends.

I just got back from a Traffic & Conversion Summit and that was in San Diego. It was a real contrast to the Podcast Movement show and that it was much bigger. I think there were 4,000 people there versus maybe 1,500 at the last Podcast Movement. It’s a smaller community and everyone has this in common like, what’s your show about and you can instantly start that conversation versus in T&C, it was like what do you do? Where do you want to hang out? I’m a paid traffic generation, conversion, optimization specialist. Like okay, I still don’t know, okay, can we work together? How could I help you? It was just not as hype of a community, not as fun of an event from that working standpoint.

Last year, the content, I thought was a little bit weaker than it had been in years past and part of that could this be like well, I’ve been doing this for three years. I’ve been to three of these now. It’s like I already know that, I don’t know what sound like pretentious in that way but it’s like where is the advance track or where is the veteran track and stuff like that. It’s a cool event. I think Dion and Jared do an awesome job with it and looking forward to see what they have in store for this summer.

Craig: You touched on something that struck a chord with me. People come to us at podcast where they say hey, how do I start a podcast and we know that well because we do it every day. We get people started with what I think is a good recipe for getting started, iTunes, Stitcher, Google Play, launch with three episodes and ask for ratings and all these things that, I don’t want to say a lot of people know, but a lot of people know.

After that, you hit the upper bound of podcasting knowledge. This is my naivety, but I feel like a little bit quickly, there’s not so much you can do with your podcast to make it extraordinary, in terms of audio. You’re talking to the mic and you record it and you put intro and outro music with it but from there, it’s like brand building and community building. As the podcast goes itself, I feel like it’s a well understood box that you need to operate in. Is this making sense at all?

Nick: Right because it’s like you’ve given yourself the constraints of your own show and the format and the stuff and not to say you can’t ever change that up. But to a certain extent, it is what it’s going to be and then it’s like unless I want to start a new show to play around with this new style.

Listeners have come to expect to certain consistency and that’s important for branding like the voice over guys being at the front of just about every episode. It’s like an important branding thing, like I try and start with consistent language like lead into the interview with consistent language. It’s just like taking a play from traditional radio, it’s like that consistency on that morning commute. It’s like that familiarity where the station that I grew up listening to while getting ready for school, it’s like I know at 6:45 every morning, it’s the Beat the Producer trivia game. There’s something to that consistency and having different segments, it makes sense but it can be tough to grow beyond that as an artist.

I haven’t try out different formats down that path. Passive Income I think is a great example like experimenting with the narrative style that he has before or is more recent one where you talked about his journey as a public speaker or he laced in clips from all these different speeches. I thought that was cool. Just taking us down this six or seven year journey of him as being intimidated to get up in front of people on the stage, to being a really polished and professional public speaker.

Craig: Taking the box that you’ve set your show to live in and then experimenting a bit around that is the way that it stays fresh for you and interesting and exciting and engaging 220+ episodes.

Nick: Yeah, it’s like give the people what they want. If it ain’t broke don’t fix it. For them like you still want to experiment with everything as you have different ideas for it. One of the episodes I’m trying to map out, trying to plan out for this spring is taking the round up style of blog post and making that into audio form and try and get people to record their answers into SpeakPipe which is a lot more intimidating than answering an email. We’ll see what kind of take rate that I get on that but I think that might be a fun one. We’re coming up on the four year anniversary of the show and also, episode 250. We’ll see if people want to participate in that one.

Craig: I love the concept a lot because that’s the secret of podcasting. In a lot of ways, it’s a one way content medium, you are talking and they’re listening and then to give people the voice to participate back on the show is powerful.

Nick: We’ll see how it goes.

Craig: That will be interesting. I’d stay tuned to hear how that one goes.

Just to wrap up the thought of keeping the show fresh and reinventing yourself a little bit within the context of what you’re doing. At this point, four years into the same podcast, what have been some of the challenges with sticking with something for this long? How have you managed to be continuing to be so successful at the show after four years?

Nick: The challenges have turned out to not be the challenges that I initially thought. I initially thought, if I commit myself to doing a weekly show, am I going to run out of guests? I might run out of people to talk to. That hasn’t been the issue at all. There’s always going to be plenty of interesting people out there to talk to and who are willing to talk to you. The initial challenges that I didn’t see at the time is converting listeners into subscribers but I was able to figure that out and found something that works there.

Challenges today are like trying to fill out the sponsor calendar, trying to mix up the content in a way where it’s like, we just had an episode about self-publishing so, we don’t want to talk about that for a little while, or we just did an episode about Amazon, we don’t want to talk about that for a little while. Trying to mix up the level, beginner, intermediate, advanced stuff and trying to keep the listeners happy, keep them coming back for more and moving up that value chain from people who have never heard of you to listeners, to subscribers, to fans and hopefully, try and grow that whole pyramid as well too.

Craig: Nick, last question, just talking about sponsors real quick. Any advice for folks who are looking to get sponsors or round out their sponsorship profile with their podcast?

Nick: I’ve been doing a little bit of proactive outreach. I thought it was super smart so I had my VA go through like, hey, go through the last six months of EntrepreneurOnFire, for example, and just create a spreadsheet of all the companies that sponsor the show and list them out on the show notes because it was easy to find. I can go through like okay, that company is not a fit, I don’t like these guys. I do like this company and their products and stuff. Trying to find a decision maker or trying to figure out while we buy through an agency or do we work with mid role. That part is been a lot more difficult than I imagined or that I guess I thought it would be at this point.

I’m still trying to figure that out and a couple people have reached out and be like, “I’ll help sell sponsors on your show.” Go for it, bring me deals and I’m happy to pay you a finder’s fee or whatever. It’s still a new medium for a lot of people and that’s why I thought it was smart to target companies that you knew are already advertising on podcast versus cold pitching some other company that you like and be like, “Hey, I’m a fan of your company. I think my audience would love you too.” It’s probably a bigger hurdle to overcome.

Typically, what we do is maybe a four episode, call it a trial run, test the offer, test the response and say like, okay, now we can buy it off, a bigger chunk of episode, a bigger placement, now that we have some data behind it but even then, like you saw, it’s just a download, the analytics are horrible. A download doesn’t necessarily mean a listen. I might download something today and not listen to it for six months. It’s on my phone for that long and I was like, oh, I’ve been meaning to check this out. I think with better analytics it’ll become easier to sell sponsorships and create a win-win for everybody.

Craig: Do you see better [00:40:02] in reality. I might think the technical nature of podcasting were once the file is downloaded from the server and is on your phone, there’s not a lot of visibility into what happens then, right?

Nick: There really isn’t. Half the market is iOS. It’ll be interesting if Apple ever opened up that data but I don’t know if they will anytime soon. For Stitcher where it’s streaming, you can get some more interesting data or even plays that happen on your website, you can get some more interesting data but from the book of this stuff like happens on a local device and it’s like they’re going to send that data back to Apple to publish out to the world, probably not. That’s one of the frustrations.

Craig: For sure. We looked at trying to tackle that technically with third party app makers. Those guys have a lot of privacy concerns themselves with everyone measuring everything about every user in the mobile world. I think the podcasting world, the producers and the consumers want to keep some of the anonymity of podcasting. The advertisers want all the visibility but everyone else wants to keep it just like it is which I can’t argue with. I might think it’s nice to say hey, this is our show and I had 10,000 downloads, that’s what we know, I know that I want to start tracking, did you listen past 12 minutes? That’s a little weird.

Nick: It’s like where did you fall off because that would be valuable information as a host, be like well, this part of the conversation was a little slower and you lost people there. That would be good to know or just like if they bailed right after the intro, clearly, you didn’t give them enough reason to stick around like what’s in it for me. It’s lessons learned.

This was at New Media Expo presentation where it was like with radio, people are always coming in at the beginning or always coming in, in the middle. There’s no beginning to any radio broadcast versus podcast like everyone starts at the beginning like how quickly can you get to the point, how quickly can you explain what’s in it for me for listening to this and try and keep people engaged. I think Michael O’Neal does a good job of that after studying traditional interviewers and stuff. Bringing people up to speed in the middle even though they probably started at the beginning, hey, once again we’re talking to so and so from this website and he’s the author of blah, blah, blah. He’s trying to give them plugs in the middle. I think he does a great job.

Craig: Yeah, interesting, awesome. Nick, thank you so much for your time today. Can you share with folks where they can learn more about you and The Side Hustle Show?

Nick: sidehustlenation.com. It’s the best place to find me. Of course, you’ll find The Side Hustle Show in iTunes or wherever you find podcast result.

Craig: Awesome. Nick Loper, thanks so much for your time and for coming on the show.

Nick: You bet man!