Jared Easley Interview Transcription
Vernon Ross Interview Transcription

Justin Sisley:

I would be lying if I said I had no intentions whatsoever of monetizing it. I definitely had that in the back of my mind, going into it – listening to John Lee Dumas and Pat Flynn, and they were making lots and lots of money!

Harry Duran:
PODCAST JUNKIES. EPISODE 38.

Today I speak to Justin Sisley, he's the host of Driven to Better. It's a relatively new podcast, and what I found interesting was A) the fact that Justin reached out to me, and typically, I don't have people on the show from a cold intro. If you will, I like to meet people through a mutual friend, or [have] people that I've engaged with at a conference or someone that was recommended to me. But I think what struck me from Justin's email was the fact that we were able to have a chat and I was able to find out a little bit more about what he was doing with Driven to Better.

I think the way he articulated how he wanted to have a different kind of podcast, and have people on his show that you wouldn't see elsewhere, and he was really really cognizant of that fact and took that into account with the booking of his guests. It's really a collection of interviews with folks that you can relate to, and it's not people that you've seen all over the podcast world, just appearing on everyone else's show.

We chatted for a bit, and I realized that he would be a good fit, and we scheduled the conversation that you're about to hear. I don't think I was disappointed, because in some ways, Justin reminds me a lot of myself. His attention to detail is apparent in the design of his website, and in the way he approaches his artwork positioned on the site and how he lists out the podcast interviews. I think we found that we approach podcasting in a similar way, and I know that he's just getting started on his podcast journey and is trying to figure out where it's going to end up. But I think that he definitely brings a passion and an interest to podcasting that I think is refreshing, and I was really happy to talk to him. I hope you enjoy the conversation as much as I did.

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Harry Duran:
So Justin Sisley, welcome to Podcast Junkies.

Justin Sisley:
Thank you, Harry, I'm glad to be on the show. Glad to be able to have a good conversation about podcasts with you.

Harry:
So, from everything I've seen online, it'd be safe to say that you're also a podcast junkie?

Justin:
I am! Oh God, yeah. Not only just doing my own, but listening to [them]. I don't really listen to music much anymore.

Harry:
Do you remember what was the first podcast you ever listened to?

Justin:
I do, actually. It was The Foolish Adventure Show with Tim Conley and Izzy Hyman, I think.

Harry:
What's that one about?

Justin:
It's entrepreneurship. It was probably two or three years ago that I started listening to it. They don't produce the podcast anymore, but from that podcast, they actually had Pat Flynn on and that's when I downloaded Pat Flynn's podcast, and that just opened up a waterfall of podcasts onto my phone. Now I'm probably subscribed to damn near 20 podcasts at this point.

Harry:
Yeah, it's so funny that we can't ever listen to as many as we would like to. I start to listen to them at 2X speed because really, that's the only way I can get through the back-catalog.

Justin:
Yeah, I'm at 1.5X, so kudos to you getting up to 2X. I feel like I've got to work up to that.

Harry:
It's like a muscle, I think if you start to do it, you'll get used to it and it might sound weird at first, but then you get acclimated to it and it's hard to go back afterwards.

Justin:
Yeah. Have you ever gone back to 1X and they just sound drunk! It's pretty funny.

Harry:
Yeah, everything moves so much slower at that point, and then you realize – the example I've used in the past is if you're driving on the autobahn at like 150 miles an hour, there's really not much you're going to be thinking about at that point, and you're going to be so laser-focused that, ironically enough, you probably won't have an accident at that speed, at opposed to driving at like 30 miles an hour. Then you figure ‘Oh, I'm not going that fast, but I can check my phone, I can check a text, I can fiddle with the radio or play with the seat', or just anything besides focusing on the road. That's actually a more likely opportunity for you to have an accident.

Justin:
Yeah, that's a good analogy, especially for entrepreneurs who tend to have that shiny object syndrome – we're always fiddling or trying to multitask a little too much, I think.

Harry:
This is such a small circle of entrepreneurs when you're actually in it. You see that other people are doing it, and you start to see the same names over and over, and I don't know if it's the same thing for you, growing up in Madison, Wisconsin, that you noticed a lot of people around you were entrepreneurs, and that's what drove you to have that bug, and led you eventually to the podcast?

Justin:
To be honest, no. I grew up in a fairly small town. I've been in Wisconsin all my life; I was from the Milwaukee area originally, and then I moved to Madison to go to school and I just stayed here afterwards. Around me was no entrepreneurs at all. I went to College for accounting, and I ended up being a public accountant after I got out of school, which didn't last very long. But yeah, up until I was probably 22 or 23 years old when I quit my accounting career, that's kind of when I started hanging out with entrepreneurs. I don't really have any friends from childhood or even High School or College that are entrepreneurial like I am, which kind of sucked! Still, it's hard because I'm trying to find those people, but it's really hard because a lot of people are in a lot of different types of businesses.

You probably have encountered that there's different kinds of entrepreneurs; you've got the guys who just want to run the world, who want a huge company and all that stuff; and then I'm on the other side of that. I'm more of a lifestyle entrepreneur, so I'm happy with some good cash-flow and working from home and just kind of being able to chill and take a week off and go on vacation whenever I feel like it. If that means I only make enough to get by, that's fine, as long as I'm happy. It's interesting to try and find somebody with the same mindset. It seems like a lot of people in Madison are more of that tech-entrepreneur, looking for a huge change-the-world type of business, and I guess that's just not my end goal.

Harry:
What's the equivalent of the tech area within Madison? I know obviously on the West Coast, we have Silicon Valley and even here in the LA/Santa Monica area, we have Silicon Beach. Every major city has a tech hub – is there one in Madison?

Justin:
I don't think Madison's big enough to have a separate area for it, but we have the University of Wisconsin here, and that has 40,000 students, or something like that. Pretty much the whole downtown area revolves around 1) It's the Capital of the State, so there's a lot of government here, and 2) the University. The whole downtown area is very much focused on a lot of entrepreneurial stuff; there's not really one set pocket of it. But there's a lot of tech stuff coming out of Madison and it's been getting some press lately as being kind of the Silicon Valley of the mid-West, if you will.

It's not a big city, there's maybe a quarter million people here, but a lot of tech companies come out of here. Obviously, Chicago's a big hub for that too, but Chicago's also just a huge city.

Harry:
Yeah, I was wondering because I'm trying to figure out where your inspiration comes from, where you would look to for a mentor for something like technology, or in your case, the impetus to start a podcast?

Justin:
If you can figure it out, let me know, because I can't find a really good spot to find a mentor either. There's one other podcaster that I know of in Madison, and I met him for coffee, but he doesn't have the same type of podcast. He's got a different mentality, I think, so yeah, it's tough finding somebody in person. I know, obviously, there's a million people out there who have coaching courses and coaching programs and packages. I'm still hesitant to do that – 1) Because I'm broke, and 2) Because I really like that personal feel of being able to meet somebody face-to-face and talk things through.

Harry:
So for the benefit of the listener, Justin reached out to me probably about a month or two ago, and I tend to get a couple of requests for folks to come on the show. I think, Justin, what stood out from your request is obviously I went to the website and I looked at what you had put together in terms of the podcast so far. Really, what caught my eye was the fact that there weren't a lot of familiar names in the guests you had, so talk a little bit about what your idea was for creating a podcast that would differentiate yourself from what you had currently seen or had been listening to up until that point.

Justin:
Yeah, and I guess I'll preface this with the disclaimer that I love listening to podcasts, I love listening to the big ones. I listen to John Lee Dumas, I listen to Pat Flynn, I love those shows and they provide a ton of value, but you're right when you mentioned before that you see a lot of the same people on different shows. My goal with this was that everybody's creating an entrepreneurial podcast where they interview other entrepreneurs and they'd all love to have Tim Ferris on their show, they all have John Lee Dumas and Pat Flynn, and they're all trying to get the same kind of people on there. And with that, it's hard to differentiate yourself from the hundreds of other business podcasts out there.

So my goal was to really really focus on the entrepreneurs, the really early-stage people, and I don't have a hard, fast rule for that. It's typically been people in the first 3 or 5 years of their business, but I don't think I've really interviewed anybody that's further along than that. The point of that was to 1) provide some press or publicity for these new businesses, because I've done the same thing. I've started several small businesses and several of them have failed already, and I know how hard it is to get your name out there when nobody's ever heard of you. You're not going to get written about in the paper or magazines or anything like that when you're in the first couple of years of your business, unless somehow you created Uber or AirBnB, that sort of thing.

The whole goal is to really focus on the early-stage entrepreneurs, to give relateable interviews with people who are out there, grinding out there business every day, rather than hearing from somebody who is so successful now that it's hard to relate to them. Mark Cuban became a millionaire, what 15 years ago? Maybe even more than that? What he did back then will not work today; the landscape has changed too much. Even somebody who became successful 5 years ago – it won't work today. If you tried to launch an AirBnB today, it's going to be a heck of a lot tougher to be that unicorn that they are now.

Harry:
Yeah, I think it's the big take-away, or idea that really resonates with me, and it comes from a book that I re-read recently, called Blue Ocean Strategy, I don't know if you've heard of it?

Justin:
Oh yeah, definitely.

Harry:
So the concept there is to look for areas that are untouched, instead of trying to innovate on something that exists already, so there's probably a ton of people doing that, and I think you might have thought of that as you were taking that approach because most people would say ‘Okay, let me create a podcast and then I'll just do a variation of what's out there now', which is why you see the proliferation of the [dot]preneur, [dot]onfire podcasts. I have a feeling, especially when you see that they're following a certain template, I don't think that they're going to last long. I'm glad to see you took a different approach, and you really look to highlight people that weren't getting highlighted, and I think in some cases, people that have probably never even been on a podcast before.

Justin:
Yeah, I'd say the majority of my guests probably have not been on a podcast ever, or even done any sort of audio interview.

Harry:
So that must have been challenging. I have the benefit of interviewing podcasters, and as you can imagine, the majority of them have at least a decent mic set-up. I generally tend to have good quality audio from my guests, so I'm lucky from that respect. Have you run into any challenges in bringing people onto your show and realizing that they may have never even owned a USB mic before?

Justin:
Yeah. I mean, luckily, a lot of people have MacBooks these days, and built-in mic on those is actually pretty decent. It's not awful. The thing I've run into the most is actually people wear the iPhone headphones with the built-in mic.

Harry:
Yeah..

Justin:
And that mic picks up any sort of -if it touches your clothing, you hear it. It just has a lot of feedback in it. I can tell, as soon as they get online with me, I can just hear it and I know the exact sound of that microphone, so I'm like ‘Are you using the iPhone earbuds?' They're like ‘Yeah'. So I say either 1) If you have a MacBook, just unplug them and use the built-in mic, or 2) Be very, very conscious of where that mic is and make sure it's not rubbing up against anything as you're talking. There was one that was so bad that after I recorded it – I didn't think it was that bad as we were going along, but I went through and started editing it, and it was so distracting and I couldn't even air the episode. I just had to scrap it.

Harry:
Yeah, it's one of those live and learn episodes. It'd probably be helpful if they just held the mic away from their shirt while they're talking.

Justin:
Yeah, I guess it's one of those things, you're right. You've got to learn as you go.

Harry:
So what's been the most interesting story? You're probably close to 40 episodes in – it looks like you're on 37 on the site now.

Justin:
Yeah.

Harry:
What's been some of the most interesting stories that you've had from the people that you've interviewed so far?

Justin:
I always talk about a failure with every single guest that I have. I think it's really important to bring out the failures that people have had, because I think you learn as much, if not more, from your failures as you do from your successes. We've had some interesting failed businesses come up. One that comes to mind was actually Caleb Brown, who runs a company called Handmade Tea. He got some press for one of his failed businesses, like some heavy press. He started a quarter delivery service for people doing laundry at the laundromat, so it was big on College campuses. All it was, was you basically paid – I don't remember the exact numbers – but you paid let's say $20 to get $15 worth of quarters delivered to your house because you were too lazy to go somewhere and get change. They actually got a bunch of press, mostly negative, like BuzzFeed or TechCrunch saying ‘This is the dumbest business ever, I can't believe people are doing this.'

But ultimately, what killed it was the terms of service for the payment processor. Apparently, selling money is against the terms of service for the big processors like Stripe and Square and all that, so that's what ended up killing the business, but it was just funny to hear that people were actually buying into that. People were actually that lazy!

Harry:
Well it's interesting, because I heard something – I'm a big fan of a lot of the productivity hacks out there, so you're always seeing new ideas come around, and I think there was one which was called Nimbl. It's basically the same concept, but it's like an ATM. I imagine it's an iPhone app, and if you sometimes go to a restaurant and you realize you can only pay with cash, apparently the service will deliver to you at the restaurant, or wherever you're at – they'll deliver cash in hand.

Justin:
That is nuts. I can see that, I suppose, because you might not plan on that. I mean, laundry? Come on, you know you've got to do it every day. Get some quarters next time. Or not every day, but you know you've got to do it every week or whatever. Just get some quarters.

Harry:
Yeah, it's called Nimbl.

Justin:
Okay, that's actually pretty cool.

Harry:
It looks like it's still around, but the first few transactions are free, and then you're charged $5 per delivery, which is obviously an outrageous ATM fee. Again, with all these things, it's really convenience that you're paying for. If you actually try to do the math, it doesn't make sense, but if it really saves time or if you're having a $300 dinner or something like that, and for some reason, the restaurant doesn't take credit cards, you wouldn't mind paying someone $5 to bring that money to you.

Justin:
Yeah, definitely, I can see that. Those subscription box services are getting really huge now.

Harry:
Yeah.

Justin:
There's a subscription box service for literally everything. I somehow came across – I think it was in a Facebook group, I'm in a few groups for entrepreneurs, and there's one for condom delivery. You can get a weekly condom delivery. I can just see guys enrolling for that just to show off, like ‘Yeah, I have to get them delivered weekly!'

Harry:
Yeah, that's funny. I think there was an article from the CEOs of BirchBox – these two ladies that, I think, kicked off the whole idea and I think they deliver make-up. It's a multi-million dollar company now, and obviously, they've had a lot of people steal the idea, or just borrow the idea – like BarkBox for dog food delivery, and there's a couple of others.

I, myself, use something similar. It's not a box delivery, but I use Blue Apron. I don't know if you're familiar with that, but it's prepped ingredients for three meals, delivered to your house every week.

Justin:
Oh okay, no, I hadn't heard of that one.

Harry:
Yeah, there's Blue Apron, there's Plated, there's probably a couple of others that exist now, but the great thing about it is that it delivers these fantastic dishes like tandoori chicken, shwarma and meatballs, and literally fish and every kind of combination of ethnicities and meals from all parts of the world. A lot of times, they involve these crazy individual spices that you would never buy, or you end up buying for one recipe, and then when you try to use them, it's like you use them that one time and then you never use them again.

Justin:
Oh yeah, I definitely know how that goes. Everybody's got that cabinet full of them in the kitchen.

Harry:
So yeah, it's cool because it gives us unique dishes every single week – stuff that we would never even make. You do have to do a lot of the chopping of the vegetables yourself, but what's great about it is that you get this variety of food, and every time you finish a dish, you feel like MasterChef.

Justin:
Yeah, that's one that I would definitely be interested in. I can't cook. I mean, I can physically cook things if somebody tells me what to do, but yeah, usually it comes down to that I don't have the time to really go grocery shopping. I make dinner for myself and sometimes my girlfriend, so when you're cooking for one, a lot of recipes aren't really meant for that. So you go out and you buy a whole bunch of this one item, kind of like the spices, but with everything else. So you get a bunch of peppers or something, and it's like ‘Well now I've got to figure out something to make that has peppers in it every night this week'.

Harry:
Exactly. I'm thinking about all the unique companies that you have on your site, and I'm wondering if you could talk a little bit about the process for actually tracking these down. The fact that they're unknown means at some point, they were unknown to you as well, and you've probably got to do some research or you've got some places to look to continue to ensure you've got a fresh supply of new guests coming onto the show.

Justin:
Yeah yeah. Honestly, Reddit has been a huge source of guests for me. There's the sub-Reddits – are you familiar with Reddit?

Harry:
Yeah.

Justin:
OKay, so there's the specific sub-Reddits for startups and entrepreneurs, and so I'll post there and just say ‘Hey, I'm looking for guests, you've got to be in the first 3-5 years of your business in order to be on the show. Send me a message, let me know what your website is and what your business is. I'll see if it's a good fit, and if it is, we'll get you on the show'. That's probably been the best source so far, but I think that might be running dry because a lot of the people – if you've ever been on r/entrepreneur, you realize that a lot of those people are really ‘wantrepreneurs'.

Harry:
Yeah.

Justin:
They don't have a business or they would say they have a business, but what they actually have does not in any way constitute a business. That well might be running dry soon, but I've actually found that now that I've got, like you said, close to 40 interviews under my belt, it's pretty easy to get past guests to refer other people. I always ask guests on the show, after we finish interviewing, if there's anybody else that they think would like to be on the show, definitely send them my way. Those people, I barely have to vet because the person who's already been on the show knows exactly what they're in for. They're not going to recommend somebody who wouldn't be a good fit, so that's been a great way to do it too.

Harry:
Yeah, it's a good point. It's always key to ask those people at the end of the interview – is there anyone else you think would be a good fit for the show?

Justin:
Yeah, I've got some good people that way. I did an interview with a guy in South Korea –

Harry:
Wow.

Justin:
He lives in Seoul, and after the interview, he actually referred me to another guy in Australia who I interviewed then, so that's kind of how I got international, too. It's been awesome so far.

Harry:
Yeah, I saw you interviewed Kevin Lavelle from Mizzen & Main.

Justin:
Yeah, he was a great interview. He referred me to Adam from Blue Claw, who was, I think, Monday's episode.

Harry:
It's funny because I read something about Kevin – I think it was Kevin; it was definitely Mizzen & Main, so I don't know. Is Kevin the CEO?

Justin:
Yeah.

Harry:
Yeah, so it was Kevin, because he talked about the Tim Ferris effect because he actually ended up advertising on Tim Ferris's podcast.

Justin:
Yeah, that's how I found him. That Medium article kind of went viral a little bit, so I just reached out to him on Twitter. I said ‘Hey, I saw your article, it was a great read, and was wondering if you'd want to be on a podcast about early entrepreneurs?' He's only been in business for about 2 or 3 years now, so it was a good fit for the show, and he was like ‘Absolutely!', and we got him on.

Twitter's been amazing, too, for finding guests and just connecting with listeners. It's been incredible how many people I get. I interact with everybody who follows me on Twitter. It gets tedious sometimes, but it's important.

Harry:
Yeah, one of the things you can do, and something that I've done recently, is create a separate Twitter list of people that have been on your show, because a lot of times, what you want to do is take advantage of the fact that you've established a relationship with these folks who've been gracious enough to be on your show. A lot of times, what we do as podcasters is that sometimes, we are so concerned about moving on to the next step or the next guest that we sort of let our early guests fall – not fall by the wayside exactly, but just kind of ‘out of sight, out of mind'.

One thing I did recently is you can create custom Twitter lists, and I created one that is basically Podcast Junkies guests, or whatever I called it, and it's just a way for me to, every once in a while, see what my past guests have been up to and just continue to re-engage with them. There's a whole concept of networking that says you have to keep these contacts fresh, and so occasionally, you have to reach out to people. Not every two or three weeks, maybe every month, depending on who the person is. I think it's a good way to grow your network, and you want to grow your network obviously from people you've already spoken to, so you've already done the homework on these folks, you've already actually engaged with them. You're sort of half-way there in terms of establishing relationships with them, and you never know how these will pan out, so why not take advantage of the fact that you've already lit that spark and continue to engage with them on a regular basis.

Justin:
That's definitely a good tip, I will put that into action tonight for sure.

Harry:
I think it's important, not because you're waiting to see if any of these guys goes public and ends up being the next big things, but I think it's just that people can understand and relate to you when you take a genuine interest in what they do and you don't ask them for anything when you're offering any help or any services, or any guidance for them. A lot of times, what you can do is say ‘Hey, I remember during our interview we talked about this topic and I just read this article about this. I thought it was great, so I'll send it over to you.' Just kind of send it out there without expecting anything in return. I've done that a couple of times with past guests.

Justin:
Yeah, I've definitely noticed that some of my guests – three of them, actually – have had Kickstarter campaigns going on when I interviewed them, so I definitely keep track of those. I'm happy to say that all three of them completed their goal, and one of them is significantly over. I think his ends tonight. Twitter's been an amazing way to keep track of those people and to find guests and find listeners. I've interacted with a lot of listeners on the show, and that feels so good when you have somebody who you have no idea who they are, and you see them tweet saying ‘This is my new favorite podcast', and it's yours! You're just like ‘Wow, that is so awesome, I want to give this guy a hug!'

Harry:
That's very cool.

Justin:
Yeah, it's been an awesome experience so far. The podcast just allows you to reach people you don't know – more so than, I think, a lot of other mediums would ever allow you to do.

Harry:
What I thought was interesting – I was looking through a couple of blog posts, and I think you'd posted something on Medium as well. One of the things that attracted me to it – it's really an analytical post that interested you, and I think it's probably because of your accounting background, but I know you do the Top 50 Influencers; you've done that a couple of times on the blog post, and then on the Medium, you did a sort of break-down, I think you called it A Numbers Geek's Study of Top Post Titles. Do you plan on doing more of that? More of the posting around stats, around podcasting, or on blog articles?

Justin:
Yeah. The Top 50 is something I plan on doing monthly. I've done it for two months now, and I have been procrastinating for this month's list, but I'm running out of time, so that should be done next week.

Harry:
What was funny about that was like ‘Let me see if my show is on there', and then I started to see traffic of some of the folks that are on there, and the Twitter traffic for some of the folks that are on there is less than mine, and then I realized that my podcast is not in the business category, so that's probably why it doesn't even have the opportunity to show up there.

Justin:
Well, yeah, it's only business podcasts, and it's only those in New & Noteworthy, so going in the same direction as my show, I only wanted to include people who have new shows. Yours wouldn't have been in New & Noteworthy at the time, either, so you would have been doubly disqualified, I'm sorry to say.

Harry:
[Laughs] It was a reminder. I think at the beginning I stayed out of business because it was such a crowded field, but a lot of times, I play around with the categories, and I think I recently actually switched back into business, just to see if it drives any traffic differently. It's kind of hard to measure some of those things, but I think it just speaks that continuing to try different things and different strategies to see what can drive some of that traffic up. I think every podcaster knows that the iTunes algorithm is a bit of a black box.

Justin:
Yeah, it's so weird. There were times when I was in New & Noteworthy – me being as analytical as I am – I was just constantly looking at it and seeing ‘Where do I rank? Where do I rank?' and I'd go from being in the Business category, I think I peaked at Number 3 one day or something, but it wasn't after a big day of downloads, it wasn't after a lot of reviews. I could not figure out how I made it to Number 3, and then the following day, I was down to like Number 30 and I had the same amount of downloads and I got a couple of reviews, and I'd moved down. I have no idea how that ranking system works.

Harry:
Yeah, it's kind of crazy. I think they want to keep it like that, but you were using Moz, right? To determine at least some of the traffic? And I think you were using Twitter traffic to determine the rankings for your list?

Justin:
Yeah, I used Moz's Followerwonk feature –

Harry:
Okay.

Justin:
So it measures interaction on Twitter, not just number of followers, so that way, somebody who has 500 followers but is getting a lot of interaction will outrank somebody with 10,000 who really doesn't do much on Twitter, and we definitely saw that in the list too.

Harry:
So, Justin, stepping back – when you thought about starting the podcast, there's such a proliferation of podcasts out there right now, were you thinking that this was going to be a hobby or because you have the entrepreneurial streak in you, did you think at some point you'd find a way to monetize it? You may have heard already, it's very challenging! Are you thinking about a long game-play here?

Justin:
I would be lying if I said I had no intentions whatsoever of monetizing it. I definitely had that in the back of my mind, going into it – listening to John Lee Dumas and Pat Flynn, and they were making lots and lots of money! Insane amounts of money from, essentially, their podcasts. They make the money from all over the place, but what started it all was them having a popular podcast. That's definitely in the back of my mind. Am I doing anything now to actively try and monetize it? No. Other than the occasional affiliate stuff, you know, www.Audible.com – you can get an affiliate account with them, and that fits well with my show because I always ask my guests, kind of like John Lee Dumas, I always ask them for a recommended book, because I'm a huge book nerd. I love reading and I typically have two or three books in progress at any given point.

I do ask them about that, and I insert a little plug after that for Audible.com, where they can sign up and do all that jazz. Other than that, I'm not monetizing it right now. I'm not seeking sponsors, I'm not putting together any paid service or paid coaching class or whatever everybody goes after. I don't have a big enough audience, even if I wanted to, so at this point, I'm just trying to grow the audience, get on some good guests and really try and interact with as many people as I can.

Harry:
I think you might have an interesting approach, and opportunity, because of the nature of the guests that you're bringing on. You're talking to a lot of early stage companies, and some of them have been successful, like Mizzen+Main, and Beardbrand, is it?

Justin:
Yeah, Beardbrand.

Harry:
Well these folks are up and coming, so you may want to think about ‘How can I provide more help to that area, where it's the 3-5 year startups?' I'm not sure what that would look like, but just sort of focusing on what that niche is so that you're not this shotgun approach entrepreneur podcast, you're really looking at the early entrepreneurs. I know that you focus on a lot of folks that have actual physical products, too, which is something a little bit different than what most of the online entrepreneurial podcasts are doing.

Justin:
Yeah, that was my goal as well, with it. Tech companies – I'm not going to not interview tech companies or tech entrepreneurs, but they do get more than their fair share of press and coverage, and internet marketing is all a variation of the same type of thing, so there's really only so much you can say in an interview and only so many people you can interview about online marketing, that sort of thing.

Yeah, I definitely did consciously put a focus on physical product businesses or just different stuff. I still have a lot of areas I want to get into. I'm actually really looking for a stand-up comedian to have on the show because I think it would be interesting to hear about the business side of that. You go see a comedian and you just go to see them as an entertainer and they're funny, and that's great, but it would be really interesting to me and I think to a lot of other people to hear actually behind the scenes and the business of being a stand-up comedian. How does that work? How do you get into that? How do you promote yourself? I think that would be really cool.

Harry:
Yeah, I definitely think that's a unique path that you should continue down, because like I said, it's different than what I've seen out there so far. Unless there's other people doing what you're doing – but you just got to me first!

Justin:
Yeah, I'm sure there are other people doing it – I know there are! But I just try to differentiate myself by being very focused on interaction. It all comes back to interaction, really. I try to talk to anybody who will talk to me that listens to the show, and my main way of doing that is on Twitter. So whenever people mention the show or whenever people follow my Twitter, I always try to get a genuine interaction there. It's always a ‘Thanks for the follow', but then there's usually a follow-up question after that: ‘Do you have your own business? How long have you had it? What are you struggling with the most?' That sort of thing, so that's how I'm trying to differentiate myself as being very accessible, I guess.

Harry:
It seems like because of your accounting background, and maybe this is your tendencies and the fact that the blog and the site itself is pretty clean – I like the look of it a lot. I like the design elements and how all the episodes are laid out, so is that inherent in your nature? To be very structured in terms of how you organize your day, and do you have a morning routine?

Justin:
Structured is intentional on the website. I can't say that I do a morning routine now, I've just started though. I can't say that before that I really had a super structured day. I now do the Miracle Morning – I'm sure you've heard of Hal Elrod.

Harry:
Mhmm.

Justin:
I'm only in week 2, so it's still a task, it's still a chore to get going on that stuff every day, but hopefully later on it'll become second nature and it'll have a great effect on me, but we'll see. I've got to give it a good fair shake and maybe it'll work out after a month or two, or maybe it won't; we'll see. Do you have one? I'm interested in hearing about your routine.

Harry:
Like I said, I'm a huge fan of productivity. I try to get up around 5.30am/6am and do some meditation. I think the days that I do do it, it definitely helps balance out the rest of the day. And then I just have some positive intentions about what I want to get done overall in my life, that's usually helpful. I try to work on the thing that moves my business forward the most.

A lot of times, there's 4 or 5 things you want to work on – I'm not necessarily always successful, but if I have the awareness to think about what's the one thing that's going to move my business forward, or increase my income, my revenue on the products that I'm offering now, do that. If you do that and you get that out of the way, then you can almost be forgiven for doing some other stuff that's more time-filler stuff. Maybe organizing your social media posts or fixing up your website, but I think what you have to be careful of is not to fall into the trap of busy work just for the sake of doing something that you think is productive. The whole day can go by and then you can look back and say ‘You know, I really didn't do anything to grow – in your case, your show – and move it forward or get it out to more avenues as much as possible'. You have to do that.

Even if you don't have a very very rigid morning routine, and I use Evernote for a lot of my brain dump stuff and everything that I have a note of. I used to use Notepad and Post-Its and things like that, but I make more of an effort in putting it in Evernote so it's always there. It's like my offline brain. My notes are there so I take one note that I read every morning and that's the one with the affirmations and the things I want to work on. Have some sort of structured routine, I think, is my advice, so that there's one major thing. Ideally, if you can figure out what that is the night before and have that ready to go for you in the morning, you're not kind of fumbling around. The worst thing to do is sit at your computer in the morning and say ‘OKay, what do I want to do today?'

A lot of people use their calendar for that. I know a lot of very successful folks. I was talking recently to Jordan Harbinger and Greg Hickman of Mobile Mixed, who's also touched on this before. He said if it's not on his calendar, then it's not on his agenda. He even schedules things like ‘Lunch' and ‘Breakfast' and ‘Meditation' and ‘Exercise' because otherwise, that empty space is sort of a black hole. It gets filled up really quickly with meaningless stuff.

Justin:
Definitely. I'm using Calendly now to schedule interviews. I finally bit the bullet and upgraded to the paid version of it so that I can have a bunch of different types of events. I feel like kind of a – I don't know, I hope people don't see me as pompous or too busy for them, but it's just so damn convenient. You can't argue with it. When someone wants to get a coffee or a beer, I'll be like ‘Yeah, use this link to schedule it'. I literally have a guy who I'm going to get a beer with for happy hour next week on Monday, and I had him schedule it on my calendar because I use it for everything. I set aside time last Saturday for day-drinking and yard games. I scheduled that in my calendar – Noon to 10pm: I am unavailable for anything but beer and yard games. It was like the first over-70 degree day in Madison so I had to take advantage of it.

Harry:
That's hilarious. I think that's the first time I've heard someone use a Calendly link to schedule drinks with a friend, but that's actually a very good suggestion because like you said, I know the most successful people don't even manage their own calendar because they don't trust themselves to not screw it up.

Justin:
Yeah. I was in that boat before Calendly. I've got to shout out to them and promote them, because that's made it so much easier to manage my schedule.

Harry:
Yeah, and from a design perspective, I really really liked it. I know a lot of people swear by ScheduleOnce, and a couple of the others like TimeTrade, and some other sites, but I think just from a look and feel [perspective], I really love Calendly.

Justin:
Definitely. I looked at ScheduleOnce too, and the interface was not something that appealed to me right off the bat, and so I went with Calendly. I think John Lee Dumas even said if he could go back, he's kind of committed now to ScheduleOnce, but there's a guy whose calendar has to be insane. He said he would go with Calendly now, too.

Harry:
That's funny, I hadn't heard that.

Justin:
That reassured me!

Harry:
So what does your family think about what you're doing? It sounds like based on what you talked about with the environment in Madison and maybe the fact that it's not even in your family, are you one of the few entrepreneurs in your family? What do your friends and family think about it?

Justin:
I'm the only entrepreneur in my family that I know of, and one of the only entrepreneurs in my friends. My core group of friends doesn't have another entrepreneur in it. Obviously, I've made those friends along the way because they were other entrepreneurs, but as far as people who were friends first, I can't think of anybody really who's an entrepreneur.

I'll be really candid with you – I went to school and I got in a massive amount of debt to get a Masters degree in accounting from the University of Wisconsin. Even though it's a public school, it's not a cheap public school to go to. My family was a little worried when I was 23 years old and I was making close to 6 figures, which in Madison, for somebody that age is quite a bit, and I quit to start my own businesses. My family was definitely a little worried about me at that point because even though I was making that much money, I was not spending it the way I should have.

When you're 23 years old and you're making that kind of money, you're not thinking about ‘Oh, I should probably pay off all of my school loans right away'. You think the world is just coming to you and you've got plenty of time to get rid of it. So yeah, they were definitely worried. They were a little distrusting at first, but I think now that I've been able to explain it to them and I haven't had to move back in with my parents yet, they trust me enough now that I can make a go of it. Even if I'm not successful, which to be honest, I wouldn't consider myself a successful entrepreneur quite yet, I can at least get by. I do still have a job, actually, but I had to take a job because I knew something had to give. The bills had to get paid, the school loan's had to get paid, so taking a job is sometimes a necessary evil for an entrepreneur, but I realized I can do that now and I've got plenty of time to work something out and replace that in the future.

Harry:
So digging a bit deeper into the personal side, what would you say is the most misunderstood thing about you?

Justin:
Misunderstood thing about me.. I guess maybe that I just like to talk too much?

Harry:
[Laughs]

Justin:
I guess it's good that I'm in podcasting. I do like to talk a lot, and I think sometimes it might come off as arrogance because a lot of times, I'll talk about things that I've done, and it's really just that I get uncomfortable in moments of silence, or if there's not a conversation flowing, I get uncomfortable and I just start talking about whatever I can think of that happened that day. I think that's probably the biggest thing, it's just that people might see that as me being arrogant and wanting to talk about myself. I think I'm just nervous and don't know what else to say.

Harry:
Yeah, you're definitely in the right profession – podcasting – if you like to talk.

Justin:
Yeah, definitely.

Harry:
Well, it's funny because most people – you'll realize when you think about people who are bloggers and writers and the creative types. Some people love to create content; people like photographers and things like that. You find with podcasters that they like to talk, and even in their blog posts they tend to have them dictated or they use a service that will do short videos with them, and they find that they can communicate their message more effectively than having to sit down and actually write out a whole blog post.

Justin:
Yeah, I'm in that boat. I don't like the blog posts that I've written. The list is okay because it's a list, and my analytical mind can handle a list, but the other posts I've attempted writing, I'm not terribly pleased with them. Like you said, I don't feel like I can communicate best through writing. I'm also a bit of a perfectionist so I'll go through and I'll re-write a paragraph like 10 times before I move on to the next one. It also takes me forever to write a blog post, which is why I don't have more up.

Harry:
Yeah. I think we're similar in that nature as well. What other content do you find yourself constantly talking about? Whether it's another podcast or TV shows or movies that you would also recommend?

Justin:
Are you saying non-business related?

Harry:
Yeah, non-business related. A lot of times, you find that you're passionate about a TV show or a movie that you've seen recently, or in our case obviously, podcasts – just so it's not limited to podcasts, I was wondering if there was anything that you've consumed recently that you're raving about?

Justin:
I'm a big fan of stand-up comedy just in general.

Harry:
Okay.

Justin:
My favorite place to go on the weekends is the local comedy club, which I'm blessed because the local comedy club in Madison is actually really really good. They get some big name people there. I'm a big fan of stand-up comedy when I just need something in the background while I'm doing other things for the podcast or whatever. I'll usually just go onto Netflix or Hulu or whatever, and pull up one of the Comedy Central hour-long stand-up comedy conglomerations. They've got 5 or 6 people going through, so yeah, that's a big part of what I do to just relax.

Harry:
It sounds like the podcasting and the comedy and the fact that you like to talk a lot has all sort of come into play together and it just kind of describes another picture about your persona.

Justin:
Yeah. I'm definitely the immature one in the group. I just try to make every situation as light as possible, and I'm definitely the non-stressed guy. I really don't get stressed out very easily – or maybe I do and I just handle it well? I guess I haven't figured that out yet. But yeah, I'm always the guy cracking a joke at probably inappropriate times. It goes back to like I was saying before – I just get awkward or a little uncomfortable when conversation subsides, so then I'll usually crack a stupid joke.

Harry:
Well, I think it fits you well in terms of podcasting because it probably lends itself to you having things to talk about when you're on the show with your guests.

Justin:
Yeah, I sometimes have to restrain myself from taking over the interview too much. This is awesome for me, Harry, being on the other side of the mic and I get to do a bunch of the talking, so this is interesting. I've only done one before where I was being interviewed, or I think maybe it's two before this one, but it's definitely different. But yeah, sometimes I have to stop myself and be like ‘Look, he just made a good point, just say thank you and leave it at that, and move onto the next question'.

Harry:
Exactly. You've just got to let the conversation flow, and I've found that the Q&A formula didn't work for me early on and I sort of ditched it, and now I just let the conversation flow, and I think it just sounds a bit more natural.

Justin:
Yeah, it does. I've listened to several of your shows and they flow really well. It doesn't sound scripted at all – well, because it's not. A full disclosure for everybody listening – I asked Harry if there was an outline before, and he said ‘Nope!', and I was like ‘Alright, if we're gonna do this..'

Harry:
Yeah, exactly. I think what you find is just take an interest in your guests and that's just advice to you and to the listeners as well. I've said it a couple of times, but just take a genuine interest in your guests. Listen closely to what they're talking about; it's no different than if you were to go to happy hour and you'd met someone new that your friend introduced you to. If they start talking about a topic that's interesting, you're naturally going to have a follow-up question and it'll just lead to a longer conversation, and I think that's something you can do when you have guests on your podcasts.

Justin:
Yeah, definitely. Nobody likes the guy at the networking event – well, it can go both ways I suppose. There's the guy who talks about nothing but himself, and then there's the guy who literally will not answer your question because he's responding to your question with a question for you. And that can get a little annoying too, I suppose.

Harry:
So, Justin, thanks for taking the time to come on the show.

Justin:
Yeah, definitely, I had a blast. I thank you for having me on – it sounds like you set a high bar for your guests and I'm glad I was able to get over that.

Harry:
Yeah, I'm really excited about what you're doing and I'm looking forward to getting an update in a couple of months and seeing. I think you're headed on the right path; you're going after guests that are not the normal guests, and I think you're highlighting these folks in a unique way. As you look to monetize the podcast or get ideas for what you can do in the future, it may not necessarily revolve specifically around the podcast.

The more conversations you have, whether you understand it or not, you're going to become a subject matter expert in the art of podcasting itself, and if Madison is not a big hub for this sort of topic, there's a real opportunity for you to take a leadership position in the community and do everything from volunteering, or get paid to teach at a school, or speak at small conferences that are coming to your neighborhood or your city, or even train people locally. You'd be surprised how many people locally may need help with this sort of thing, so I think my advice to you is just to keep your eyes open for any and all opportunities that may tangentially appear as a result of the show you've started.

Justin:
Yeah, that's a really good point, I appreciate it. I will definitely look out.

Harry:
And so the best place to track you down online is…

Justin:
Probably Twitter. I mean, the website for the show is www.DriventoBetter.com, all of the episodes are there, I'll do a shameless plug for my DTB+ club, which is free. It's just a community of entrepreneurs; we have a private Facebook group where we all try and help each other out with business ideas, and I kind of play the teacher, if you will, mostly holding people accountable. We do mid-week accountability posts where I check on people from the last week – what they said they were going to do and hold them accountable. If they didn't do it, there's no shame in that, but it's at least trying to hold people accountable to grow their business and not just do a bunch of busy work and feel like you did something in your business. So that's there.

Twitter is just @DriventoBetter; that's probably the best way to get hold of me.

Harry:
Okay, so folks can follow you there, and keep close tabs, and if listeners know of anyone who has a new business that they're just getting off the ground, about 3-5 years in the making, and specifically someone who hasn't been highlighted before and you think they've got a good story, then I'm sure Justin will be more than happy to speak to them.

Justin:
Absolutely, definitely.

Harry:
Alright Justin, take care and have a fantastic week.

Justin:
Yeah, thank you, Harry, you too.

—-

Harry Duran:
Thanks again for listening in and I hope you enjoyed that conversation with Justin. I really think he's doing something different and you're going to see interviews on Driven To Better of folks that are working hard to get their entrepreneurial endeavors off the ground, and I'm glad that he's highlighting these folks. I'm definitely wishing him luck. I'm pretty sure if he continues on this track, he'll be around for a while. As always, we'd love your support on www.PodcastJunkies.com/iTunes, and leave us a rating and a review. Don't forget to subscribe as well.

One other thing that we're trying to get people to sign up for – we have a PDF that I put together. It's eight tools you can use to be more productive in your podcast production, and I've made it a bit easier for you to subscribe. You can actually send a text message. Text the word ‘PodcastJunkies' (all one word) to 33444 and then it'll prompt you for your email, and you can sign up right away, so you can do it while you're mobile. Do that and I'll get you signed up to the list and get you that PDF right away.

Alright guys, thanks and as always, I appreciate your support and I'll catch up with you next week.

 

 

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