Lily D is an ASMR YouTuber. What does that mean? Listen to the podcast to find out.
ASMR helps with anxiety and insomnia. Lily started making ASMR videos in 2013 and has racked up over 65 million views of her videos. In this conversation, Aaron and Lily discuss how she got started, the positive & negative messages she receives, and what the future holds for a brand built around an individual. Never miss one of our best episodes by subscribing to the newsletter. Lily’s Challenge; Try deleting Instagram (or your most used social network) for a week. 
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YouTube Lily's Book Mettle by Lilliana Dee If you liked this interview, check out episode 386 with Jon Shanahan where we discuss men’s fashion, learning from working in a corporate environment, and how he’s built a YouTube following.
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TRANSCRIPT
Watson: Thank you so much for doing this. I'm excited to be speaking with you. Lily Whispers: Thank you for having me. Watson: I want to start with a very specific question that I get a lot. I see a lot of people struggle with, and taking your life back to 19, you first heard, I believe, was Lana Del Rey do an ASMR video. Lily Whispers: It was actually Appreciate ASMR doing a Lana Del Ray makeup tutorial. Watson: At that point, that was a catalyst for you to go start creating your own videos in this very distinct space, but even just to take that and actually take it in the action of making the thing, and then to take the thing that you made and publish it. So many people see that as a significantly daunting, uphill battle. What was that process for you before the first time you press publish? Lily Whispers: That's so funny that you asked that because I remember realizing that if I thought about it too much, I wasn't going to do it. I'm pretty much a perfectionist with most things that I do. I was like, you know what, if I don't jump in, how do you swim? You jump in the deep end. You figure out how to doggy paddle, and God forbid, you know, you just figure out how to swim. I just remember I was to go to work, and I propped my iPhone up on, God, I don't even know where it was propped up on, probably like a cup or or something. I filmed, and my first video is 15 minutes long, and it was so rushed. I was so nervous, and I remember I published it and I was just like, ‘Yolo. Let's see what happens.’ To be honest, I don't know what mentality I was in, but I just realized that if I didn't just do it, I wasn't going to do it. I kind of thought about my channel name, which was officially or before it was Lily Whispers. ASMR, it was Whispers Lily because Lily Whispers was taken. It was Whispers Lily, and I didn't even have any graphics on my channel. I think I just uploaded it, and I was like ‘let's see what happens.’ It did kind of well, and everyone was really supportive and receptive of it. I think the feedback is what kept me going, but it was just kind of like a last minute, ‘okay, I have 15 minutes before I have to leave my house for work, I might as well just do this.’ Watson: Yeah. It's so interesting that you said that there was some of that feedback because the other element is someone creates, someone publishes, and then there's going to be negative feedback. There's gonna be negative critique. Then there's also this untalked about section of like, there was just no feedback. I put it out there. Nothing happened, no one said anything, and there wasn't a reaction, but for you, it seems like there was a response or feedback pretty quickly after putting out there for the first. Lily Whispers: Yeah. This was, God, so long ago. This was when ASMR content was just beginning. So everyone was just absorbing as much as they can. Now, everyone, you know, not everyone, but a lot of people have ASMR channels now. Everyone's thinking about making one and everything. So back when there wasn't a lot of content out there, people were constantly searching for it and finding it. So from an SEO perspective and a video SEO perspective, I kind of was in people's feeds. Because it's such a niche audience, I feel like that first video, I think I got 3000 views on it in the very first couple of months, or whatever it was. I was thrilled. I was like, ‘oh my gosh, this is like the best video I've ever done. This is amazing.’ I had dabbled in YouTube before, so I kind of had an understanding of the platform, but yeah, getting no feedback, which I've had projects where I've gotten no feedback on you're like, ‘oh my God, I'm presenting to a wall.’ It's kind of daunting in that way. I lucked out with getting immediate feedback and immediate good feedback. People were very constructive. Watson: Maybe before the first day of ASMR came out, maybe that's kind of what was happening to some degree with the stuff that you had put out before was like, if it elicited such a response the first time you did that, it kind of speaks to from a comparison standpoint where the stuff was before that, is that accurate? Lily Whispers: Yes, exactly. Watson: So take me through comparing and contrasting then and now. For me, what was absolutely eye opening was to see the Michelo Ultra commercial, where it was completely out of left field. Some people try to ruin the ads beforehand and see what's coming. I had no idea. I was like, did they just do an ASMR ad during the Superbowl? Lily Whispers: So funny, my friend from Florida called me two weeks ago, and he was like, ‘Lily, did you see the Michelo Ultra commercial?’ I'm like, ‘listen, buddy, you're a little late. I've definitely seen that.’ He was like, ‘man, that’s so awesome.’ I was like, ‘yeah.’ Watson: So, the first time you did it, you made it on the phone, but now the gear and just the standard competition has raised. When more people come into the space, it's no longer, you know, maybe, you could get away with it, but the standard for the equipment that you have to use is much, much higher. Lily Whispers: Much higher. When I started, there were no binaural microphones. People were using their iPhone, and people still do that. There is a type of ASMR that has a lot of white noise and we call that Lo-Fi, low frequency, like Lo-Fi music and radio stations. ASMR has a similar thing. I personally love those videos, but then you see these people actually making their own microphones. This guy made this microphone with actually four ears on it. To build that, you think of where technology has grown of, okay, you’re lucky if you had a microphone on either side of the camera to kind of give a binaural effect, but now you have microphones that are mimicking the human ear in four places. That's crazy. Watson: Can you define binaural? Lily Whispers: Yeah. Binaural means on either side. So, when you're listening to music on your headphones, you hear it on the right or the left side. Watson: How have you thought about that for yourself? Now, I'm getting back to just all these kinds of themes of content creation, regardless of vertical, of someone who just pursues having to have the best. I don't quite have the right camera set up, things, or the other thing before I go and make the thing when, you know, that's a part of the equation. That's not really the core of anything that you would ever create. Lily Whispers: No, it's not. You have to think about what you're going to bring to the table that's going to set you apart from everybody else, whether it's what you talk about, whether it's your personality, whatever it is, it can't just be about technology. Anyone can come out and buy the newest, greatest things. Unless you, I kind of have a taste for it, unless you bring something new to the table, it's just going to be like everything else. So, the technology can only get you so far. That's half of it. Watson: Yeah. So, what I'm really curious about as it pertains to the growth, there was an appetite for ASMR. You even alluded to the SEO strength when you were first getting off, and how that video got discovered, but you have a real comprehensive digital marketing skill set. I think the other mistake that an outside observer can make is to say, ‘well, right moment, right time,’ or ‘she's done it consistently and therefore worked,’ but there had to be some strategy behind the growth of what was going on. It's informed by a career that you have now in the digital marketing space. Can you speak a little bit to the elements outside the actual execution of the video that went into the growth of your channel? Lily Whispers: Right. If you think of YouTube as being the second largest search engine in the world, you think about how many searches Google gets, think of YouTube as being just a little shy of that. People are always looking to YouTube for everything. The YouTube analytics platform has grown a lot since I've been on YouTube, but that's really insightful. When I first started my channel, I also had an internship, the following summer in analytics and search engine marketing. That's where I kind of got my feet on the ground. It's funny because my ASMR channel took off that following summer, and I kind of applied those things. I look to see what people were searching for, what related channels we're doing, getting inspiration there, and analytics. It's so fascinating what the numbers can tell you. Of course there's those trendy, faddy type videos of right now, in the ASMR community, everyone's eating edible objects. I know that sounds really weird, but bear with me. So I guess on ETSY, people will sell fondant, the cake stuff, and they'll make makeup out of it. Then, you know, and ASMR would be like, ‘I ate a makeup palette’ and things like that. That's a really trendy right now. If you think about how to grow in that sense of what the wave of what is within the niche or whatever it is. Another thing to say is mukbangs, which are the eating videos as well. Those are very, very popular. Watson: I literally only just found out about, I didn't even know that that was the correct pronunciation of it, because I only had read the title of it. I only found out about that like a week ago. Lily Whispers: Wow. You're really late. That's not even an ASMR thing, Aaron. Watson: I'm sorry. That hurts. Lily Whispers: It's like everywhere. I mean, maybe it's not everywhere, but, it's very, very big in ASMR now, as well. People love a good crunch. Watson: That is part of it though, that there's a never ending, a never ceasing, new thing to be discovered. Regardless of anyone who you may perceive to be on the cutting edge, there's just always, maybe I'm just sounding like an old fart here, not knowing where my phone is, but that is the perpetual role of both the digital marketer and the creator, it’s to continue to uncover those things. Lily Whispers: Right. If you could think about that as being, ‘the sky's the limit,’ that is not only daunting, but it's also exciting, too. You're like, ‘what can I bring to the table that's different?’ I recently saw somebody doing a drunk ASMR, and luckily I'm 25, so I did a drunk ASMR, and I think out of all of my videos I've ever posted in the past three years, that one has done the best in the first 48 hours I've never posted. Watson: As you've connected with other YouTubers of a similar size, whether, you know, necessarily even for a collaboration, but just, that's kind of how the world works. People in similar circles run together. Do you see a similar theme or trend of a successful YouTuber with some sort of a background in another digital marketing role, and that is contributing to the success that we're having? That's what I'm, in a limited scope, seeing from previous interviews, we've done with Brad and with John Shanahan, I'm curious if you've seen something similar. Lily Whispers: GB ASMR is one of the largest ASMR artists in the field. I'm saying field like, it's a digital marketing field, but like on YouTube for ASMR. She has a degree in video creation and production, things like that. She's totally all over like this, and her videos are so wonderfully executed. It's a science, it's a talent, and she's so talented. She has the backing to back it up. Watson: So, as we step back from YouTube for a moment, and look at the career of Lily, and at this unparalleled age of you being able to build a brand around yourself, you being able to be a media company own your own, and having effectively done that, not spoken to it, but effectively done that. It's a really interesting place to sit in terms of, I alluded to the different types of content out there, but even just the directions that you could go. You recently chose to go the direction of publishing a book, but when you have an attention and an audience and a creative bent, it seems like there's a lot of directions that you can go. How have you thought about the subsequent steps of building out the things that you're doing, and are you always prioritizing growth and expansion? Are you pursuing creative expression? Are you pursuing business like top line revenue for the brand? How do you think about balancing those things? Lily Whispers: That's a really good question. I've been writing since I was a kid, and I always wanted to write a book. It didn't really have to do anything with ASMR. I touched upon that in my book, but it was just kind of those iCloud notes, those notes within my phone, that I just had to get out there. I decided to share it with the world because my audience, just to give you context, it's 80% or 85% female this month. It's usually about 79% female. So, I have a very large female audience, and they're always asking me for advice and things like that. I felt that by honing into my own life's experience, what better way to do that than through a book. I try to do that with my videos as well, but sometimes people are looking to escape their problems through ASMR videos because of the sounds of whispers and things like that. So of course, I didn't want to talk about, you know, too many deep things on YouTube. So, the book was kind of that medium for it, but I also have to think of my brand. There's a lot of people that are pushing merch. If you think of clothing as being the second, most popular form of waste, after plastic, that really makes me depressed. I've always come from a very eco-friendly family. We were always very cognizant of recycling and turning off the lights and things like that. The little things that we could do to make up the big picture. I knew that I never wanted to come out with my own clothing line. I didn't want to contribute to consumerism in that way. If there was some way that I could take my words and my wisdom and put it on paper in another way, that's what I did as far as the fueling. I guess the catalyst of what/ how I would like to grow, it really depends on my own self growth. If I would have started YouTube with money in mind, I don't think I would be where I am today. Obviously we're all paying bills and things like that, but I genuinely enjoy making ASMR videos. I never expected to make any money from it. I never expected to land the brand deals that I did. Any time it starts to feel like work, because it's my hobby, I stopped doing it. I've been working on my book for two years, and if it started feeling like work, I stopped doing it. I know that a lot of people are different, and we live in a capitalist society. Making money from the things that I put out there is really gratifying, but what means more to me is the fact that people are like, ‘wow, I can relate to this. This is amazing.’ That's more fulfilling to me than money in my pocket. Watson: So in a similar way, despite what has been built, if ASMR, for whatever reason, you wake up tomorrow, it stops being fulfilling or satisfying or interesting to you. Would you have the capacity to let that go and go in a different direction? Lily Whispers: I would never let it go because of the connections and the relationship that I have with my subscribers. It is so fulfilling beyond any dollar amount. I can't quite describe that because I would just continue to have that relationship with them. If I stopped making money, I would continue doing it, because I have that relationship with my subscribers, and it's a hobby of mine. I genuinely enjoy doing it. Watson: Talk about what that's like. The other side of being a media entity and having these means of distribution that no one ever had before is also that your inbox or DMs or other avenues are open, and a lot is coming into you, probably incomparable for almost anyone else listening to this out there.Talk a little bit through what comes into your inbox, both positive and negative, as you want to. Lily Whispers: Oh my gosh. I get everything from fast fashion brands begging me to send me clothes and post pictures, to really creepy DMs, to like stalkers, to media companies. I've been reached out to by major companies, and I've been featured in the Washington Post, Vogue Australia, a New Yorker, Vice UK. Those are some really big media companies. I think that was brought to me through my presence online. I guess, being a public figure, which I hate calling myself that, but on the internet, I have over 260,000 subscribers. I feel like it's a big amount of people. Watson: That's like half of the humans that are in this entire metropolitan area. That is a lot of people. Lily Whispers: I hate thinking about that. I'm like, ‘crap, that's so much.’ I remember my goal for subscribers was always getting as much to fill Beaver stadium of Penn state. I was like F all you guys because I got bullied the heck out of at school when I was up there. I withdrew from university because I was bullied on my ASMR videos. Watson: That's not cool. Let's go in the positive direction. Let's talk about some of the young people, young women, that you have the opportunity to then be an outlet, to be a voice to. Maybe they're going through something similar, or maybe they just need a different perspective, and you happen to be the person that they reach out to. I'm sure that's also happening. That's the more positive side. Lily Whispers: Yeah. I get so many kind messages and emails and DMS. It makes me so happy cause I make videos based on what I'm experiencing. There wasn't a heartbreak, ASMR video, and people always look for ASMR for anxiety and depression. I'm like, ‘what's another experience that we have as humans that we're always looking to talk about or have someone to relate to.’ It's heartbreak. I personally didn't have an eating disorder, but a lot of girls that watch my content are struggling with body image issues. ‘Can you talk about this on your channel?’ I've done that. I've gotten really great, positive feedback from, ‘oh my gosh, I had my heart broken. Thank you so much for those kind words. They were really uplifting. I feel like I have a friend.’ These are people that are turning to ASMR because they don't have those people in their real life to open up to on the phone or friends like that. Likewise with the body image things, that's a huge issue that I found that in college as well, a lot of my girlfriends struggled with body image issues, and it wasn't a talked about subject on YouTube in the ASMR sphere. I was like, ‘okay, let's talk about some body positivity, things like that.’ Watson: What processes or habits or practices do you have in place to control for some of that? When you can effectively open your DM or whatever the platform is, and all these messages are coming in, you have no idea what the next one would be. There's like a little teaser thing, but there are creepy people out there. There are incredibly kind, heartwarming people out there, and it's a lottery to some degree, like what it's going to be today when you open up app 1,2, or 3. Lily Whispers: Yeah. I could get a dick pic or a fan art. You just never know. Yeah. I've gotten both. Watson: I’m sure. What do you do to get away from it or to reset or to take time from yourself? I know how to do that physically. I know that if I go in the room on the other side of the building and lock the door, I am away. But, you know, we are dealing with apps that have been engineered to keep up on the dopamine drip. Lily Whispers: Yes. I actually just, Michelle Montana was, and I was on their podcast, The Influence, a couple of weeks ago with Alyssa. We were talking about how to break up with your phone. They literally build technology to make us addicted. It's crazy to think about. Unwinding, I'm still working on that. It feels so great to just be able to put down my phone and be in the moment with my friends. I think last summer when I was kind of in a funk and kind of across, I was spending more and more time online trying to seek these connections that I wasn't getting in my relationship or with my friends and things like that. There's nothing like human connection. There's nothing like self-reflection. I personally like to drive. I just like to get on the highway, go shopping and I'll go up 279, and I'll just get in my car and blast music and think, and that's my way of unwinding. I'll take the long way home. Watson: Yeah, for me, sometimes, the email inbox can be more of a trigger than anyone. I'm very lucky to just have a lot of positivity coming to me across the platforms that I'm on. But you know, opening up in my inbox, like after 9:00 PM, I'm trying to just absolutely stop, unequivocally. Lily Whispers: Yeah. That's difficult to do, have you tried doing the do not disturb? Watson: I did, but then I got annoyed. I was fighting myself. Lily Whispers: Because when you’d open your phone after nine, you'd see all the notifications anyway. That's how I struggle with that. I definitely have gotten very good at figuring out if a message is going to be bad or good. It's nice because I can click on it and see it. I don't accept all of them now, I just screenshot and put them on my story because I didn't know that starting out. I was accepting these DMS and saying, ‘oh, thank you for the support.’ Now, not to say that I don't like that, but there are some subscribers that I'm like, ‘okay, they're trying to get to know me a little bit.’ I have to keep that level of separation with my personal and my public life, because if not, who the hell am I? Watson: Yeah, there's a weird thing that happens because you've shared some of your story and it's like, ‘wow, this person just is lacking some degree of EQ or social awareness.’ I mean, there's plenty of people that don't necessarily get it in the real world either, but at least, you know, I can communicate non-verbally, I can communicate tonally, and I can communicate with my words that this needs to change socially. That gets missed when I'm seeing basically an icon, an image of you, and I can then just type out whatever I want and hit send. It's a completely divorced experience relative to what we are actually biologically primed for. Lily Whispers: Yeah. I made that error when I was first starting out. I thought it was so great that I had all these subscribers. I was kind of letting them into every aspect of my life, like on my Snapchat, they were sending me all these messages, and I was just available 24/7. I didn't have any time to just be Lily. That was like crazy. I remember I deleted Snapchat and made a private one. I go through phases every spring where I'm like, ‘I don't want in the public eye. I just want to be.’ Sometimes, when you're just online all the time, and you have all these eyes on you, you just kind of want the opposite of what you have. Watson: So, do you act on that? How does that actually manifest? Lily Whispers: It manifests into a lot of frustration, usually, and I'll go back and forth. What I usually do is do things like a social media cleanse. I delete all the apps and I'll go dark for a week or a week and a half, and then I'll go back on. I know that sounds so pathetic. Like, ‘oh my God, only a week,’ and things like that. Watson: Most people aren't even doing that, even if they don't have the following like that. Lily Whispers: I knew that I was getting to be a problem because I was getting onto these apps, and I was getting anxiety about not responding to these messages about not being available to these people. At the end of day, I don't really owe anyone anything. It's this weird thing about being an internet personality. It's like, you have to be present because that's kind of how you build your following, but then, what do you do to step back. I take a drive, but I need to find other avenues to have time to myself because you can only drive so many places in Pittsburgh. Watson: Yeah. The reason I'm really appreciative of you speaking about it, and I want to continue to have conversations in spaces, it is just fundamentally different than anything that happened before. I'm just thinking of the first old suburbia, but Frank Sinatra or some older celebrity, for as massive and the awareness that they had was insane. The means of distribution that their brand had to the world and to the country and the continent, they had an immense amount of privacy because of just a different era of information technology. To be simultaneously sitting at a point where you are tremendously empowered, but also dealing with challenges and problems that you hear someone like, ‘oh, well the stoic philosopher, like from the Roman empire. They had problems.’ Of course everyone had problems, but these are interesting and nuanced in ways that we haven't really ever seen before. Lily Whispers: Our generation is so connected, it's sick. It is really crazy. Then, you look at the generation that's younger than us, and they're getting cell phones when they're 6, and you're like, ‘oh my God.’ We're just, we're in a different era, and I get it. Everyone has their own problems and things like that. I sound like so far. There are bigger things happening in the world than being on social media, of course. I always feel bad when I need to talk about my first world problems and privacy, but we are so available and so accessible and can get anything. It's creepy. Watson: Yeah. I think it's tremendously important that we try to understand ourselves and understand what is actually happening, because there is no playbook for anything like this before. There are other characters that you can study, who are modern contemporaries, but studying a personality of the past in certain ways might be helpful, but they're not actually operating on a model like you did. Let's take Johnny Carson, for example. Johnny Carson was the voice of a generation, but Johnny Carson didn't really sell anything. He showed up on the TV, he got paid for the TV, and I know he had other business endeavors, but it was a very linear arrangement. He just had to knock it out of the park. In this case, the same way that you chose to go and bring to the market your book. You've made this conscious choice not to go in the direction of clothing. When you have an audience that's bought into what you're doing, when you have a voice and a perspective that people do value and they want to hear from, that is a tremendous amount of power to go in countless directions. There are influencers outside of merch who are launching an alcohol brand or launching a jewelry collection or launching makeup and perfume. Rihanna, a perfect example with Fenty. There are so many options and avenues to go down, it's tremendously interesting to me. It's tremendously fascinating. Lily Whispers: Yeah. I've been contemplating going down the makeup route, but it would have to be on brand with me. It would have to be cruelty free, vegan, recyclable, like all those things. Then, that gets expensive. Watson: Yeah. But it's also the way that you are, and it's deeply authentic, in the same way that it's apparent through the answers related to fashion and makeup. You have your own set of non-negotiables, and whether it's explicit or implicit, that's coming through in the stuff that you're putting out there. Someone's gonna be like, ‘well, Aaron, she did like a drunk ASMR, that has nothing to do with cruelty free makeup.’ But, the way that you are and the consistent values that you carry with you are manifesting themselves, regardless of whether you're consciously putting that out into the world. Lily Whispers: Oh yeah. In my drunk ASMR, I also talked about makeup. I'm always just me. Watson: Yeah, an exciting future. I'm excited to continue to follow along and see what other other moves you make. Is there anything you would like to share today before we do our standard sign off? Lily Whispers: No, I don't think so. I mean, if you're interested in ASMR, you should definitely check out my channel. It's called a Lily Whispers ASMR, L-I-L-Y Whispers, and then ASMR. It stands for autonomous sensory meridian response, if anyone's curious. Watson: Right on, hopefully I remember to do that in the intro so that people aren't like halfway through, ‘what are they talking about?’ We're going to link Lily’s Instagram, Twitter, all her other good links in the show notes. For this episode, you can find it on goingdeepwithaaron.com/podcast for this and every episode of the show. But as we do, Lily, at the end of each interview, I want to give you the mic one more time to issue an actionable personal challenge for the audience. Lily Whispers: Yeah. Try deleting Instagram for a week and see how you do. I found it incredibly insightful. Then, after I went dark for a week, I didn't post as much. Now, I just post memes on my story. I don't know why. It was very cleansing. Even if you can't do a week because it's your business or something like that, try three to five days. Just the weekend. Watson: The world will keep spinning. Lily Whispers: Yeah, exactly. That's the scariest part, but also the most rewarding. Watson: Well, this has been great. We just Went Deep with Lily Whispers. I hope everyone out there has a fantastic day.
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388 $70M in Fundraising, $10k Speaking Fees, and Timeless Business Strategies w/ Dave Nelsen7/22/2019 
Dave Nelsen has been a successful CEO in multiple businesses. Two of his startups, CoManage and TalkShoe, raised more than $70 million in angel and venture funding.
He has since moved into a full-time speaking career, traveling to country to share his perspective on Social Media for Business and Technology for Executives. In this conversation, Dave and Aaron discuss how Dave went from a large corporation to a startup, where Dave found the ideas for his companies, and how he launched his speaking career. Valuable listen for any aspiring entrepreneur. Never miss one of our best episodes by subscribing to the newsletter.
Dave’s Challenge; Do more listening.
Connect with Dave Website 412-779-2788 If you liked this interview, check out episode 362 with Jason Wolfe where we discuss multiple successful startups, investing, and leadership.
Underwritten by Piper Creative
Piper Creative creates podcasts, vlogs, and videos for companies. Our clients become better storytellers. How? Click here and Learn more. We work with Fortune 500s, medium-sized companies, and entrepreneurs. Sign up for one of Piper’s weekly newsletters. We curate links to Expand your Mind, Fill your Heart, and Grow your Tribe. Follow Piper as we grow YouTube Subscribe on iTunes | Stitcher | Overcast | PodBay 
Matt Stroud is the co-founder & CEO of Postindustrial Media. His new media startup is aiming to change the tenor of journalism in the Midwest.
He’s come a long way since founding a bimonthly magazine, called Deek, out of his basement apartment while enrolled full-time at the University of Pittsburgh. Matt has written short- and long-form journalism for Esquire, Harper’s, The Atlantic, Buzzfeed, Politico, The New York Times, and Reuters, and held staff writer positions with the Associated Press and Bloomberg Businessweek. In this conversation, Matt & Aaron discuss new media, recruiting team members, and Matt’s reporting on policing technologies. Never miss one of our best episodes by subscribing to the newsletter. 
Matt’s Challenge; Ignore political campaign polls and pay attention to where government dollars are spent.
Connect with Matt Website Matt’s Book Thin Blue Lie: The Failure of High-Tech Policing by Matt Stroud If you liked this interview, check out our interview with Todd Bishop about running a bootstrapped media business, our interview with Chance Humphrey about Instagram and photography, and our interview with Jon Shanahan about building a men’s fashion YouTube channel.
Underwritten by Piper Creative
Piper Creative creates podcasts, vlogs, and videos for companies. Our clients become better storytellers. How? Click here and Learn more. We work with Fortune 500s, medium-sized companies, and entrepreneurs. Sign up for one of Piper’s weekly newsletters. We curate links to Expand your Mind, Fill your Heart, and Grow your Tribe. Follow Piper as we grow YouTube Subscribe on iTunes | Stitcher | Overcast | PodBay 
Watson: Matt, I am excited to be speaking with you and I think the most logical place for us to start is just with a definition of post-industrial what it means broadly in a sociological comp context and then more specifically what it means to you. Matt Stroud: okay mmm broadly sociological context is the idea is generally that you have it's an urban planning idea and a sociological idea you have regions of the country you know I'm gonna speak like in the American conversation you have regions of the country likePittsburgh that went through incredible growth based around manufacturing and industry with Pittsburgh, Detroit, Milwaukee places like that you have cities that really came to their peak in the years of World War II and following where they had their largest populations they were the most economically robust. A lot of people wanted to work here a lot of people wanted to move here from around the world it was really nice place to be and then you started to have gradual decline that developed into pretty significant decline in 70s and 80s parts of the 90s and you know a lot of these places lost half or more of their population and you have little pockets of the country that are that are representative of that trend all over the place typically the way that people think about that area well that idea is through geographic boundaries and the way that we think about it is through geographic boundaries a lot of the cities that exist between Buffalo, New York and Birmingham, Alabama and Baltimore to st. Louis fall into that line and then really little little pockets yeah so that's the geographic region that we think of but I started it with a guy named Carmen genteel international war reporter who came back to Pittsburgh I did I wasn't doing war reporting but came back to Pittsburgh after you know traveling and performing acts of journalism all over the country and so we came back to Pittsburgh and we thought about post-industrial and in a different way a way where a way that represents rebirth and change which is similar to what a lot of these cities are going through right now right so places like Pittsburgh I'm having to rethink the way that they go into the 21st century keep the historical and keep their history in mind keep you know manufacturing in the rearview mirror but also think about where they gonna go in the future and we had much the same decisions to make for ourselves you know. Carmen kind of the the really pivotal moment of his life and the moment of his life that moved him into a new direction as he was reporting in Afghanistan and was shot like was shot with a rocket in the face and had to recover from that survived somehow and came back to Pittsburgh to rethink what kind of reporting he wanted to do in the future and whether or not he wanted to be a war reporter post-industrial as part of that rebirth for him. The same for me I mean I've spent most of my career reporting about prisons and crime and policing. My book is about policing and technology and I came to a point where I realized that there was a lot being done around the reporting that I had done previously in in the Criminal Justice space and that I had a niche that I had carved for myself but I didn't really want to be reporting about prisons and jails and police and murder and death for the rest of my life and so I needed to rethink for myself too. And so we feel like we are going through a post-industrial phase of our lives and that's the way that we think about assigning stories we look for stories of rebirth and change and people rethinking the way that they exist and how they're going to go into the future. Watson: And what's really interesting as I listen to you say that you know not that I think that there's a mistake being made in any of the way that I've been consuming both the the print edition now and the different digital context but there's like a vain - some of the stuff that I saw on the Kickstarter campaigns there's other ways that you'd spoken about that was not negative but just like people are getting it wrong and there's like maybe an implied negativity to that but really what I'm hearing here is optimism there's an there's an optimism about that rebirth you know all those words they have that very positive connotation to them Matt Stroud: I think about Pittsburgh in a very positive light and think about moving forward into the 20th century and my career a very very positive light and Carmen does as well and we came back to Pittsburgh for positive reasons we felt that there was opportunity here and yeah so there is a lot of positivity that goes into the creation of post-industrial and you know part of that positivity is trying to identify what's wrong and a lot of the Kickstarter campaign was built around that and part of the reason for that is that you know we do take politics seriously and we feel like a lot needs to change if we all have if we are all going to have honest discussions about the problems that exist on how we're going to change them Watson: Can you give a few specific examples of that? Matt Stroud: I mean we are in the midst of one of them right now right so I try not to talk about the president very frequently but he has just launched on a new campaign he's just done his official launch for his next campaign and I think it's good that he's doing that it seems to be where his strengths lie and where he as a politician is strongest but he's going right back into where he was calling names and saying things that aren't necessarily true and we are- and I just listened to I just sat in traffic for a half an hour listening to a podcast talking about politics and they're moving in the exact same direction they're covering an exact same way they're covering his campaign rally and talking about you know crooked Hillary Clinton and we're getting into the horse race part of the campaign again. I don't see anything that's changed and so I want to try to implore people through the journalism that we produce to think much more broadly about the issues that are being presented there and what they can actually change. Watson: And what's really fascinating when you look at the media business generally is the discipline required to not fall prey to that because you see, whether it's I think I listened to an interview that was like the president of CNN or something, the year preceding the 2016 election was you know far and away when the best revenue years that we've done in a long long time and for a news business that you know is undergoing a digital revolution and all these kind of forces on it to have it- you're like that- it's very understandable, at least at that level, why someone would fall prey to sensationalism or all the things that are rife issues in the world of media and it's really curious to me that like I understand the sensibility I understand the idealism behind that vision but it's gonna be challenging to have that discipline I would imagine. I imagine there's a lot of forces pushing against that ideal that you have Matt Stroud: Absolutely. If you're running a company like CNN or Viacom or whoever owns CNN right now, if you're running a company like the New York Times even but we're in a position where we're at aplace like Pittsburgh and we have the opportunity because things are relatively inexpensive and there is an appetite for new and interesting media that we can make a we can make decisions in that regar and we can try to produce a media that doesn't fall prey to that and you know I'm not holding the shareholders I can make that decision and I would like it if listeners and readers made similar decisions about the media that they consume and so really I'm not you know when I when I talk about what's wrong with media and how I wish it would change I'm not really talking to people who are beholden to shareholders in at places like CNN or or CNBC or any of the others. Like they can make the decisions that they want to make and good for them I hope they make a lot of money but we have we have the freedom to make different decisions and to pay attention to different things and so I'm really employing imploring readers and and media consumers to think a little bit harder about what they read and what they consume and how they act on that information. Watson: Yeah. And I find that the people who do take that consideration I mean I'm kind of pandering to the audience here as I say this but like the people who make that choice are some of my favorite people. Incredibly thoughtful they're incredibly articulate they have you know interesting perspective on stuff. Matt Stroud: Yeah and they listen to great podcast like this I mean they make they make decisions that are active I mean this part of why I think podcasting is such an interesting direction in media because it you can be so selective about the content that you consume and even the content you create it's so easy to make it on your own yeah that if you see a hole there if there's there's a hobby that you want to talk about. I mean, you can do that and there's a possibility that other people will listen and I'm very curious where it goes in the next 10-15 years certainly. Watson: So, one of the things and this has been a through-line between a bunch of recent episodes that we've done but the basic idea if you've got the passion for journalism or baking or working on cars and you start a business in that realm all of a sudden your world kind of changes you started the business because you love that thing and you just want to do it all the time and then when it becomes a business there's a degree to which that thing that you loved that you got into it for becomes less central and now you're running the business of that thing so I'm really curious as you've launched Postindustrial and then you know try to find the business model and the strategy behind it in addition to this level of journalism that you aspire to how you've gone about the business of media in union with the mission of the media that you wanna produce. Matt Stroud: Well a little bit of background excuse me well I this is not my first magazine that I started. I started a magazine when I was when I was in college dating myself in 2003 I started the magazine called Deek and I was much more interested in the the business of producing a publication and in toying with the idea of what I could do with a magazine at that time- DeakMagazine.com some of the archives are still out there- but that led me into being an editor for different publications and I actually made the decision to strengthen my background as a journalist and understand more about journalism because of that trajectory like I was moving in the direction of being a business person and a publisher and ran into some issues that led me to believe that I need to understand more about journalism. Then basically spent ten years learning how to be a good journalist and when I started PostIndustrial, I was under the impression that I would be able to just focus on the journalism as you as you point to but you're you are totally right when you start a business somebody has to take care of the business of making it work and so that has that has been something that I have adapted to and tried to adapt to I would say that's what has been helpful is during that ten-year period of trying to figure out what I wanted to be as a journalist and how to be a be a journalist it just became so ingrained in my head like the values that you need to bring to journalism and what the difference is between a piece of journalism that is that is sponsored and a piece of journalism then it's this quote- unquote pure and not not beholden to anyone or anything like it. It just it sinks into anything that we do and I know that when we do a piece of sponsored content like it has to be explicitly labeled and people need to know like this is a piece of work that is advertising and on the other side to give journalists the freedom to do the good work that they want to do and then hold those journalists accountable for what they turn in and if they turn something in then is that is not up to our standards to make them go back and do it again and so I think I think being educated in what you want to do allows you to hold the standards that you want to keep and also perform the business duties that you want to do but I don't know enough about business and so a lot of the education going back to going back to actually being a publisher in creating a magazine I've had to learn on the fly how to do that so that's been that's been a challenge. Watson: One of the most potent sales jobs that you've done so far has been the success of the Kickstarter campaign as a launch off point for you know proving that there is an appetite for this type of media proving that people will put their dollars behind it. I'd imagine that calls into tension to some degree a model that is advertiser supported media versus a kind of member you know audience supported piece of media. How have you thought about those two countervailing boards? Matt Stroud: For attention between the two? Watson: Yeah, if there's a direction that's more appealing to you a direction that seems more viable a direction that is just maybe how you think about it Matt Stroud: We're in a the magazine that we create is going to have to be in the models that we have are going to have to be advertiser supported. And there are services and verticals that I think as we do more research and as we get more involved here are going to be more aligned toward a member model and a subscription model and I see that as part of part of where we go like post-industrial is the umbrella above which some interesting verticals are going to emerge and that's where a lot of the subscriber interest is going to be is going to be focused. But the actual idea for the magazine has its models in entities like the Edible Products, Brooklyn, that that group of magazines, and you know the most prominent version of a magazine that does similar things is Texas Monthly yeah. Texas Monthly is a big thick advertiser-supported magazine that is fun to read and that also has great journalism in it and so that's really the direction that we're going into. Watson: Yeah that was. You say there's two regional outlets both in the Kickstarter campaign and we have coffee together and has a model where you kind of study what they're doing and try to find someone for them for that, can you speak to more of what you took away from what they're doing. Matt Stroud: From what they're doing? Watson: Yeah Matt Stroud: Okay so Texas Monthly, what they're doing is a true regional magazine and the way that they're able to do that is that there is some cohesion between the cities in Texas all of those cities think of themselves as part of Texas and can invest in the idea of being part of Texas and I thought when I initially started this project that I would be able to rally different cities and leaders and businesses in the idea that the Rust Belt and post-industrial America was a thing that they could all rally behind. In theory, a lot of the people I've spoken to in different cities have rallied behind that idea but they rally behind it less more with their mind than with their with their dollars and so the way that we've had to kind of pivot and rethink that model is to think about the region as a whole and tell stories that are relevant to the entire region and do that through in-depth reporting that is you know in the feature well of the magazine and then to have different versions of the publication that comes out that is specific to every city that we that we launched out of and so that's why it's a it's a hybrid of these two models so yes we do think about the region as a whole as being representative and then the edible Allegheny model is like we're gonna have specific cities city focused versions of the magazine so the feature well of the magazine is going to be that regional perspective and then each magazine that's produced for you know Pittsburgh or Columbus or Cleveland is going to be specific to that city with a feature Weldon is for the whole region. Watson: Makes sense, and identity is such a tricky thing because to be a Texan “Don't mess with Texas” like that there's very cohesive like how I see myself identity it's for better than that and while, you know, maybe the Midwest like you know I know what the Midwest is young and restless like that's really one of the only phrases from like a broader identity standpoint that can be that unifying at this point in time. Matt Stroud: Yeah. And it's not really a rallying thing like like you said like “Don't mess with Texas” like that is a rallying cry yeah those are fighting words right the the idea I'm from the Midwest it doesn't have the same resonance and normally it's used in a way that's that's negative yeah either negative or like milquetoast and and so there's not much to rally behind there and so you know when I talk about post-industrial when I talk about it is an idea of rebirth and change like that's what people can get behind there is a rallying cry there but there's you know this is a new idea it's not the idea of Texas as a place for fighting and so we need to we need to build it and you know we think we figure out a way to build it but you know we're business people so we'll figure it out as we go. Watson: Yeah, so there's two ways of talking about to you we're talking a little bit about speaking to people in this region about what it is and in this perspective and then there's the other articulation which might not be as as crucial at this point in time but given your background doing journalism in all these different outlets same thing with Carmen and other members of your team for the folks who aren't from this region who don't have those stories and it is a flyover state to them or whatever the the phrase may be what's the what's the narrative or what's the friction when you articulate this vision to people from outside of the region because like I'm in Pittsburgh I interview different tech CEOs every week I'm you know I'm buying I'm completely buying into this story of rebirth is there a skepticism is there a doubt like what it what is what do you see reflected when you articulate that this to people outside the region. Matt Stroud: Well, the conversation always turns to politics and so that's you know it's part of why there's an interest in politics here but it's it's part of why we focused on politics for the Kickstarter because it gets us out of the region it gets us doing into a conversation that people in Silicon Valley are interested in hearing, you know, the one conversation that people are interested in hearing about this region in Silicon Valley seems to be the idea that the duolingo campaign right you can buy a house here yeah the other is that there is apparently a lot of power and it's political power and traded in this part of the country you know elected a president and so talking to people outside of the region about how to harness that power how to think about how to talk to those two folks who live in this powerful area that has resonated to them. Watson: What- how do you provide fluency and legibility in to the mechanisms of power to someone who doesn't necessarily understand that's part of the role of the journalist is to even expose that the Fifth Estate like there's the roots of that how do you think about that through these decade that you've spent honing or your skills as a journalist to make that clear to people who might not even be aware of that power. Matt Stroud: Try that one more time I don't fully get it Watson: So, you’re basically illustrating like, “hey, we elected a president” there might not necessary be a depth of appreciation for how powerful this region is I feel a lot of people it's very clear like Wall Street they have all the money San Francisco they have all the tech in the data. LA, they have their pull of power because they make the pictures and the images that influence culture for the last century when you speak about the power that is I won't even say lying dormant here it is but it might not necessarily be as legible for someone to look at and say like that's the heart of the power of this region how do you what do you point to as being kind of the poles of power in this area. Matt Stroud: I'm not really sure you know the unfortunate thing is that the definition has been built around anger, around the idea that this is an area that was left behind I mean that is that is what Trump took advantage of and I think what what Joe Biden is going to try to take advantage of in 2020 and so the idea is how to harness that and how to get people to think a little bit differently about the what they can do with that power which again presents it as an opportunity for people who are outside like here's some opportunity here's you know Andrew Yang talking about the fourth Industrial Revolution and the the way that work is going to change in the 21st century and thinking about the idea that you're going to have people who are here in this region who are going to be significantly affected by the way that policy directs them, directs businesses to operate as work changes in the future like that is that is a conversation that we can have here and that you know people in Silicon Valley and Wall Street they can participate in that conversation and they can you know talk to people when people are listening because it involves work and it involves you know this area and moving forward. Watson: Beautiful. We spoke with Todd Bishop who is the co-founder of geek wire when they did their HQ to visit here to Pittsburgh and he spoke about being you know the small media entity more or less bootstrap but not having a shareholders or board of directors to necessarily answer to and how that affects the composition of talent that joins his organization has to be very very mindful about every single person that walks in the door and works under his banner because resources are more constrained. How have you thought about building the team around post-industrial? Matt Stroud: I mean we're in the same situation there's extremely limited resources and really where it starts is working with people who I know working with people who have done a lot of this a lot of similar work as I people who have worked alongside me at different media outlets that are here and elsewhere and it's actually created you know a challenge for us like how to get out of the the initial circle of people who I know and have worked with as freelancers like an example right so you mentioned Geekwire one of their competitors as a publication that I used to work for it called the verge and I made a lot of my contacts in media through the verge and with freelancers because the heard the verge hired a lot of freelancers and so I was I was in a position to know a lot of those people so we have we have a list of a hundred or so freelancers that freelance are some of the best publications in the country they're really successful freelance journalists they do really well but like that's a hundred people not all of them are concentrated here some people are in Pittsburgh some people are outside of the region. It's really, it's not a group of people that gets outside of the people who I know and so what were what we're thinking about now what we're having to think a lot more about is how to get out of there and that's a that's a challenge that we're still working on right now and I mean I would love to talk to what's the name of that CEO? Watson: Todd Bishop Matt Stroud: Yeah I'd love to talk to Todd about you know where he went and how he how he made that transition from the people who he knew and like people who were in his comfort zone into you know people who were outside it. Watson: Similarly, Pittsburgh you know the joke is you never more than two degrees of separation from someone and that's probably also why you love the friends or who happen to be in the circles but you know there is a legacy within the media business of seeing things as very zero-sum seeing things it's very competitive and adversarial and what I've noticed in certain instances particularly if you think of like the influencer individual creator type there's a lot of like let's collaborate let's like you know find ways one plus one equals three to use a simple business truism what have you found as you know trying to park your bus on this corner of local journalism regional journalism. Have you found more friction or have you found more kind of openness for collaboration between outlets? Matt Stroud: Between outlets I've seen less interest in collaboration though there is a Point Park initiative going on right now called Bridge Pittsburgh that is trying to change that yeah so it's putting together outlets like public source and Post Gazette and us to work on big projects together. I think that's a really interesting idea it moves in the direction of what you're talking about but you know these are all companies operating in a competitive landscape and so a lot of them are really hesitant to work together with individual content creators I find that they are very interested in collaboration particularly if you can help them achieve a goal that they haven't been able to achieve yet or don't have the time to achieve yet and so really it's a conversation everybody's open podcasters and particularly people in particular people who produce video like they do their own work they need means to help promote it get out to more people and reach a broader audience and collaborate and so that's been really great and trying to put together a media outlet that helps those folks and works along with them has been something that I've really wanted to do for a long time. Watson: Makes sense. Matt it’s been great. Thank you so much for for sharing so much time with us today and for braving all the traffic to get over here. Before we aim towards wrapping up and asking our signature last two questions anything you're hoping to share today that I didn't give you a chance to? Matt Stroud: Oh yeah. So, I just published a book with McMillan and metropolitan books it's called Thin Blue Line Failure of High-Tech Policing and it is a book about technology and policing and the big businesses that have grown out of selling to police departments. We didn't talk about it today, it's not a big part of what I do with post-industrial, but it is something that I spent quite a bit of time on and that is interesting to anybody who knows what a taser is and has ever gotten themselves into a conversation about body cameras or weapons that police use. Like I give you the business history of how a lot of those weapons and tools became big business Watson: Are you against body cameras? Is there an argument against body cameras? Is there an argument that that's not a direction that things should be going for police officers? Matt Stroud: So, we can get into this if you’d like. Watson: Yeah. Matt Stroud: The body cameras, I have been very supportive of body cameras. I think they're a good idea, but what happened the way that body cameras were sold a lot of the selling of body cameras happened in 2014 after Mike Brown was killed in Ferguson, Missouri. Do you know that story? Watson: Yes, of course. Matt Stroud: Part of what happened at that time is you had police leaders and legislators legislators all the way up to the President of the United States making an agreement that body cameras were going to be expensive they were gonna be distributed to police departments there were going to be contracts to sell body cameras to police departments and that part of that deal was that body cameras going to be available the footage would be available too and as time has progressed in the last five or so years what has occurred is that that body camera footage has become harder and harder and harder to get and the reason why is you've had legislatures like the legislature in Pennsylvania putting together laws that make it virtually impossible to get that footage so we are spending millions and millions of dollars on the municipal level to purchase body cameras for police officers and then the footage that is produced by that body camera is you know basically impossible to get in in the state of Pennsylvania in order to get body camera footage you have to know the name of everybody who is in the video footage itself without seeing the fridge you have to know you have to know everybody's first and last name in the footage and you have to make it make a request to get that video within 60 days of the event itself. So, to give you an example, if I'm aware that there was a shooting that is connected to a case that is going on right now and the case that is being tried and I want to see the video that's related to that but the video was recorded like a year ago I have no access to it and Pennsylvania law makes it so it's impossible to get and so you're seeing laws like that being passed around the country. Watson: Wow. Matt Stroud: That just kind of make body cameras basically useless for the public and so that's that's where the problem lies. Watson: I can see the impetus behind the book Matt Stroud: Yeah there's a lot of stuff. There's tons of arguments like that in the book. It's a good read, fast. Check it out. Watson: I will be sure to link that in the show notes for this episode. I also wanna make sure that people can check out Postindustrial. What digital coordinates we provide for people who want to learn more about that. Matt Stroud: Go to postindustrial.com you can gain access to all of the podcasts that we host you can get one-year or two-year subscription to the print publication and you can also read our daily newsletter, The Record, which is one of the most comprehensive daily news analysis newsletters that you will find in any region I think it's made by a great writer and thinker named Adam Shuck who's been doing a newsletter called to eat that read this podcast and we just rebranded is the Pittsburg record you should check it out um so yeah postindustrial.com no space no hyphen, postindustrial.com Watson: Thank you fantastic. We're gonna link in the show notes or find it in the podcast player for this episode. Before we let you go Matt, I want to give you the mic one final time to issue a challenge to the audience . Matt Stroud: So, I have two challenges that's related to things that we talked about the first is I challenge the audience- do I have to give them like a deadline on this? Watson: I like a deadline because it gives you, like, an actual framework for acting on it. Sometimes it goes too broad. It's like “decide what you want to do with your life and then go do it” and that's like a little too open-ended. Matt Stroud: So, we talked a little bit about politics one of them is that any time you see a measurement that shows you the the likelihood that a particular candidate is going to win like it says like you know Donald Trump's chances of winning the presidential election in 2020 is 85% and you find yourself going back to that and like seeing whether it's 87 percent or 75 percent ignore that please like so your deadline on that is November 2020. Please ignore that kind of journalism because I don't think it's helpful and then the second is I mentioned my book. One of the basic premises of the book is that you have police departments and governments that make decisions about technology that are going to spend a lot of money on based on what the technology has promised to do not what they want to actually accomplish and not what the tool has actually been proven to do so the example that comes up in the book quite a bit is the taser like the taser that officers used to subdue people tasers fail about half the time and they kill a lot of people and they are still at this point purchased by police departments in droves for millions and millions. They support a multi-billion dollar company at this point with the premise that they are going to stop shootings from happening that's just not that's just not true it just doesn't happen and so it I make the plea in the book that we need to be more careful about the money that we spend and know more about the weapons in particular that our governments are purchasing and I think that advice leads me to ask your listeners to really pay attention to the money that is being spent by your governments and make it a point to support an outlet like publicsource.org which is a great one that's local that does a lot of work trying to substantiate how government money is spent and what that government money is doing and what your politician what politicians is doing pay attention to publications like that that are really trying to help you make those decisions so that you can be better informed. It's better for communities and it'll be better for you I think as a news consumer. Watson: I love it. It is a large challenge but one that we all need to take steps towards. I appreciate you heeding the call and thank you so much for listening. We just went deep with Matt Stroud. 
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TRANSCRIPT
Watson: So, I don't do intros or outros or anything. I record that after the fact. We can just jump into it. The nice thing about doing this with a pro in the sense that you create a lot of content, you kind of have a framework, a comfort around it- the camera's being here. You're not gonna be thrown by any of that stuff now. Jon Shanahan: No, I'm used to, it got a camera on me all the time. Watson: When you started, how difficult was it? Jon Shanahan: When I started my YouTube channel or just creating content in general? Watson: The first step you were creating, how stressful was that? Jon Shanahan: Well, the first I started making was when I was eight years old, I had my mom's camcorder and I'll film my cousins, and We'd make movies and put them on VHS tapes. I'd make copies of the VHS tapes for my family. When I was in high school, I joined the video club because I had done that as a kid. I was like, ‘oh, I want to do some video stuff.’ I became buddies with the guy who ran the video club, and then everybody graduated. So, I was the only member of the video club for two years. I would go to sports events and film, and wrestling and football. I would go all over the place and like do all this stuff. So, I was the only one. He was like, ‘we got to do all this stuff to do the video club.’ Then he was like, ‘I want to be the first video production course at this high school’ at Baldwin High School. So as Mr. Schulte, I still talk to him to this day, he was like, when you think about the great teachers, he was one of the great teachers. He was like, ‘I want to do a video production course.’ For two years we kind of massaged idea of like, what does the video production course look like? What are the different breakouts, you know, projects and that sort of thing. Then he took it to the school board, and then it actually got implemented my last year. It became a video production course. I was doing stuff, then. I was like making music videos and like stupid videos all the time in my own time. Then I would do the stuff for the video club and then video production kind of launched. That was really an easy A for me. That was the, probably the first A I got in high school. I was a disruptive, bored, poor, high school student. I kind of found my way with a graphic design course. I got introduced to Photoshop and Illustrator, and I absolutely fell in love. That's where I learned Premiere and like all the inner workings of recording video and burning disks and everything. We had a 10 disc DVD burner that was the big piece of hardware that we bought with our video production budget so that we could burn multiple in one time. Then from there, I figured out I wanted to go to an accredited design school. So, that's how I ended up at La Roche, Laroche and accredited graphic design school. That's when I kept going further into photo manipulation and design and everything. Watson: You're describing a club of which you kind of allude to, where you're the only member. That seems incredibly entrepreneurial, like from a very early stage. Would you categorize it as that kind of experience? Like you were kind of self directing or was it, you know, a teacher and a single pupil? Jon Shanahan: It was more of a teacher in a single pupil then, and from there, it was okay, ‘we're going to make these DVDs for the senior dance and we're going to sell them.’ That was very much him leading me down, ‘okay, you want to make videos, but there's also an aspect of this where like, we need to buy new cam quarters and we need to fund it in a certain way, and the school won't give us money. So how do we go from there?’ So, we'd go to the coaches and say, ‘alright, we'll do your DVD at the end of the year. Pay us a thousand dollars so we can record every game and then hand them out.’ Then the parents would buy the DVDs from there. So, I actually never connected it to that. That is probably one of the earliest entrepreneurial experiences. I also did or did not bootleg movies in high school, but I wasn't doing it at that point. Yeah. Watson: That was what the statute of limitations passed 10 years from there. Jon Shanahan: I also grew up in an entrepreneurial family because my grandfather on my dad's side started a transportation company in ‘89. My parents on my mom's side, started at an ice cream store, sugar and spice in the South Hills in 84. Growing up, I was always around people who own their own businesses, but they never really said, ‘hey, you should run your own company someday.’ They were all pushing me towards going to get a job because for both of them, it was very much like they had a lot of employees and they had ups and downs and it was very stressful. Then, on the ice cream store side, they never really went beyond their single shop. It was always the one shop and they never, I wouldn't say they thrived. They never flourished, never went out like Millie's that has multiple shops and all that sort of thing. They just had their one shop, and they went in and they were always encouraging me to go to college, go to school, get a job and like work for somebody else. There was never really that thing of this is why we're entrepreneurs. Watson: Yeah. I think that's so interesting because we're like at this weird cultural point where doing something entrepreneurial is put on such a pedestal, but you were basically, you could say pushed or allowed to find your own way into doing your own thing, as opposed to I think that there's a cohort that is entrepreneurial for entrepreneurial sake, as opposed to like scratching a distinct itch or addressing of this specific problem. Jon Shanahan: Yeah. There's people that want to put it in their Instagram bio, and there's people like who you've had on the podcast where he just loves making whiskey. He is entrepreneurial in his old job at his career. Then he went and went off and did his own thing because he couldn't not do it. There's people that want to start a t-shirt company and do drop ship eCommerce because they want to say they're into entrepreneurs. Then there's people like Barry Young, who loves this place so much, and he wants to go do it. So, yeah, growing up, it was never a thing. It was always very much you will go to college, and you will go get a job, and it wasn't really like go to a trade school where to do this other thing. I actually have been pushing my brother a lot in that way. Don't go to college because we, as Shanahan men, are not built for college. My dad actually just went to a technical school and he would stay and he worked for IBM, did computers and everything, but I struggled through college a lot. My non-core or non-specialty classes, which were designed like those art classes and anything that I had to create, I was really good at, but math and science and in English, all those core classes, I struggled through those constantly. I really did not like it, but I pushed myself through it enough. My sisters are a different story, but I don't know, the men in this family are not cut out for higher education. Watson: So, when did you realize you could not not pursue men's fashion as a line of work, as an interest, as a content that needed to be created as an endeavor? Jon Shanahan: it came pretty late. So I worked out of school or actually, while I was in school, I worked for Apple. I started working at the Ross Park store. I opened that store, and then within there I got experience of how a multinational, huge company works, from training and education and sales process. I got exposed to everything there. So, I was there for four years. At the time, I was going to school, and then I was taking 18 credits, and I was working full time at Apple. My memory of that time.. Watson: That may have also contributed to your struggles. Jon Shanahan: Not necessarily. I can separate those two, even if I were to sit down for eight hours and say ‘I have to do this math problem,’ I'd sit there for eight hours and struggle for it. I thrive when I'm busier for sure. Then as I was finishing school, I got approached by the Chief Marketing Officer of Edgar Snyder, Sandy Snyder, his wife. I worked for her for a while. I started working there full-time, and I was still working in Apple because I couldn't let go of the Apple thing. My leaving of that company coincided with the divorce of Edgar Snyder, and I was working for the wife and stuff like that. It all kind of fell apart at the same time. Then I struggled for a while because I didn't know what I wanted to be when I grew up. I still know what I want to be when I grow up. But I struggled with what kind of job do I get? I can remember standing on the floor at Apple googling on the computers there because you can use the computers all day. I was like’ jobs that travel,’ and it was insurance agents, insurance adjusters or like all these goofy things. There was nothing that ever really said like, okay. So I couldn't really find anything that I wanted to do. Then from there, I took this job where I was selling credit card processing machines- it was a bad job. It was like a 10.99 job that I found on Craigslist that you would walk into companies and like, ‘you need to buy this credit card machine.’ It was kind of a rip off. After I understood the mechanics of it, I couldn't bring myself to go into companies, small businesses, family businesses. I have a family business, an ice cream store. I couldn't bring myself going in. So, I had no sales at that company, which I looked bad to them, but I couldn't bring myself to. Watson: That speaks to your character. Jon Shanahan: Yeah. I'm an Eagle Scout, I did that in high school as well. Then, from there, I had a connection with this guy I worked with at Apple and he was like, ‘hey, this company first Insight is doing really cool stuff. CEO's young, young company, growing, you should come in and interview.’ I got really lucky when I interviewed, because. The COO at the time said, ‘okay, all these big, expensive sales guys that we used to hire, they're not working out. I want young guys that want to learn, that are scrappy, that I can teach them the process and then they can go out and sell.’ I was one of three guys that were hired under that premise because I was, at this point, I had very little like actual business, a business sales experience, and I had very little experience with any other way, but I went into a six figure sales job for a startup software company with very experienced men who had created software and created companies before. If I didn't have that, if I didn't have Apple, I don't know who I'd be today. If I didn't have that job, I also don't know who I'd be today, because that was the most incredible experience. I went from walking into businesses, trying to sell them like credit cards to going into huge multi-billion multinational retailers telling the CEO, ‘you have a problem and this is how we're going to solve it.’ To have that exposure is what completely changed the trajectory of my life. I started that in May 2014. At that point, I was engaged, and in December of 2014, I got married, and I was on my honeymoon. When I'm left to my own devices, this is when problems happen. So, I spent that whole year basically going through the process of redoing a wardrobe. I had to get nicer suits. I had to upgrade my wardrobe to present myself better, but it all kind of started with Edgar Snyder because that was the first place that I had to wear a shirt and tie every day and to dress a little bit better, and all the lawyers were suits. That was the first one. Edgar Snyder was the first place-I started Apple where you can wear whatever you want. You can wear cargo shorts and flip flops. Nobody cares. Then at First Insight it was like, you're going to CEO meetings. You don't need to have a suit, but you need to be presentable and well dressed. Well groomed and everything. I was on the, I'll never forget, I was on the beach in Aruba for my honeymoon, and I was telling my wife, ‘you know what, all these brands, nobody does YouTube videos. I'm gonna start a YouTube channel.’ She was taking a nap, and she was like, ‘alright, that sounds great.’ So like from there I was. My head just spun the entire time getting home. I went home, I registered the domain on a hover, and then I created the YouTube channel. After that point, I thought, okay, name the philosophy behind the channel, everything I want to do. It all kind of catalyzed in Aruba because I couldn't find what I wanted on YouTube. There weren't really people talking about the brands I could see early on. There was this split between all the creators that do a lot of sponsored content, and they'll say all the nice things. They'll say whenever they're sponsored, but then how do you discern that, you know, between that sort of thing? I saw that very early on, and I also saw that there was a shift in 2015 where Facebook wasn't really in video, yet you can put videos on Facebook, but people hadn't gone in there. I was like, ‘video is going to be big. I have this background in video. I really want to create videos. I'm really passionate about men's style. I need to buy all these clothes anyway, and nobody's talking about them.’ So, that was how it all really started. From there, I knew I had to get my first video up very soon because I knew I could also, and I see this with the guys that reach out to me now, it's like, I want to start something. I have this idea, and I always tell him ‘just post something, get something started because you could sit there forever and never move forward, but until you start to get some kind of feedback until you make it real, that's when things start to move.’ So I registered January 1st of 2015. My first video was up on the 15th of January to me, like two weeks to get it up. I knew that year, I was going to start. I'm going to post like once a month, just, just some sort of cadence. Cause I had a monthly subscription box for clothing and I was like, I'll just post every month. I get one of these and people want to see that. I can remember the very first comment I ever got. It was from this guy named Jarome, he was Canadian because he was a Canadian brand, and he was like, ‘hey cool video man.’ I was like, ‘yes.’ At that point, I still had emails. I would get emails for every comment. So, I was sitting somewhere and I was like, ‘oh my God, somebody found my video’ because I also didn't promote it. I didn't tell my family. I didn't tell my friends about the channel for two years, at least. It was like this weird thing. I knew my family wasn't into clothing and style. So, I sat over here and did my stuff in the corner, and made my videos and posted on YouTube. I can remember the first comment I got and then from there, ya very slow roll to start to build that. Watson: I want to talk about that process, but the philosophy is really interesting to me, like anyone doing anything anywhere, going in any direction, the philosophy that they take to their work is so impactful and where they end up. So, to just put a little bit more color on the picture, there's all this world in digital marketing, in digital content creation. You're looking at people that are potentially using affiliate links. And so they have a vested interest to maybe point you towards an expensive thing, or what have you, and then as you spoke to sponsored posts, well, I'm trying to make sure that I'm not like referencing. Let's use Nike. if Nike pays me to make a video and I spend the whole video just talking about these Nike shoes and the Nike jacket and how amazing it is, there's like a reason beyond maybe perhaps my authentic opinion that I would be stating that opinion. You were very making a very specific philosophical choice, not to do that. Really what I'm hearing, is to prioritize the audience. The trust that your audience will have in you is that you'll buy something nice and be like, ‘this really isn't worth the money to me or it is.’ An incredibly impactful place to stand, particularly, you know, we can talk about the impact in retail specifically, but just in general, putting the trust of the audience on a pedestal above everything else really sounds like the core of the philosophy that you have. Jon Shanahan: Especially as we were buying stuff for our house, or like I'm really into technology. To me, the Wirecutter even like, whenever the launch in 2012, like I was in there very early and to me, I would Google audio, like a XLR, blah, blah, blah, Wirecutter. That's how I imagined my eventual YouTube channel being. It's like somebody wants loafers, loafer Kavalier, or dress pants Kavalier. I thought of that very early on. I also knew that I would have to approach it that way from the beginning in order to like, make sure I'm building that over time. I do have the way that I've built it from there. I really, you know, I try to use affiliate links because the affiliate links are the best way to stay independent of the brand. I still do some sponsorships they're involved in, but I can be so selective about it because I don't have to say yes to anybody. I've said no for four years to everything that's come across my way. From the beginning, I was like, I want to be who people can go to and trust the same way that people trust consumer reports or the Wirecutter, the same way that I do so that I can make sure I built this long-lasting brand over time. The quick buck is not nearly as impactful as this long-term thing. There's a quote in the House of Cards. He says, “money is the beach house that crumbles at the first storm, but power is the stone house that wears through centuries” or something. It's like, I can remember that quote too. I was like, ‘yes, that's where I'm going.’ I'm in it for the long run, because I also know my family's been in business for 35 years in an ice cream store, 30 years in transportation. They're like known names in the industry, and I just don't see any benefit to moving quickly, and just trying to trip over yourself on us. Hannah Phillips: The podcast is underwritten by Piper Creative shooting, editing and publishing quality content is overwhelming. We make it easy so you can save time, build your brand and grow faster. Say hello atpipercreative.com. Watson: So, talk about the patience over those four years from video one once a month to now studio in the backyard and all the gear and all the other stuff that's gone. Jon Shanahan: It definitely took a while. So like I would post once every once in a while, and I was gaining subscribers. But, if you wanted to grow a YouTube channel, you wouldn't do it the way that I did it- I very early on realized, ‘alright, if I want to be the resource for people searching for things I need to put out more, are more brands than anybody else.’ If you want to grow a YouTube channel with this passionate, dedicated audience that watches every video, you gotta put out like one or two a week that everybody wants to watch my videos. I just did a video on like a skincare routine. It's like not many people are gonna watch that, even if they're subscribed and want to know my opinion. It's only going to be the guys that want to spend $90 on a skincare routine and want to learn more about that or like briefcases, that sort of thing. I would just do it every day, between five and seven in the morning, I'd wake up, go shoot a video, edit it, and then try and get it posted. When I realized the more I posted, the more brands I could do, I just increased the cadence. So, the first year was like once a month, sometimes twice a month. The second year, I was like, ‘alright, I need to do this like once a week.’ I could just see the momentum building. So like, ‘alright, I need to do this every weekday.’ Then that's when I really ramped it up and said, ‘okay, you know, every day, edit this video, get this thing.’ Year three is really when I started to see some level of growth. That's when I could also see, when I started, I was like, ‘someday, maybe I'll be able to do this on my own.’ Year three was the time when I was like, ‘alright, I think I'm onto something here.’ That's when I could get, you know, audience and subscriber numbers that were meaningful. I was getting enough inbound questions from guys that I knew things were resonating. That's when I started to say, ‘okay, I can see a path.’ The hardest thing though is going from, I have this lifestyle that is predicated on getting a check every month or, and I should also say too, I was working a lot for the startup. I covered Europe for a while, so I was going back and forth to Europe, a ton. I was going to the West coast a lot. I was traveling. So like, there's a lot of late night plane rides where I'm in coach cuddled over my laptop, like editing this video, trying not to let the guy next to me see that I'm editing a video of myself changing my clothes in my bedroom. There were some odd times going on there. I was going through that process, I was like, ‘alright, I need to get to a place where I can cut off this very important part of me so that I can go do this other thing.’ That's when we watched it down, because from the beginning, when my wife and I got married, we pretty much knew she wasn't going to work. We knew she was gonna be a stay at home mom. She was six months pregnant when she graduated college from Duquesne. From there, we had a ton of student loans, and then I had student loans. In that third year, I was like, ‘alright, if this is ever going to be a thing, we need to get rid of the student loans, we could pay off all of our cars. We need to have no credit card debt.’ We have a mortgage over here and that'll keep going. That year is when she just said, and yesterday she was like, ‘you treated us like we were on food stamps or something.’ Yes. That's the way you got to do it in order to get rid of that big thing so you can come over here and take a big risk. It was calculated for years. So we would eventually go that way. They say like, it takes 10 years to be an overnight success. I just went into it with that mentality. It was like, Edgar Snyder is a huge name now, but he was pointing on TV for years before anybody paid attention to him. It just takes a long time. So it's good to have great examples around me of that. Watson: So when did even flip though, because if, if I was, let's just say a comedic personality, and every week I'm going to do a video and I'm going to try to make someone laugh. Let's use a simple premise. I really just need the camera and my wits and some time editing, but you're also interacting with all these different brands. At the one end of the spectrum, when you're established, brands are gonna send you stuff cause they want it reviewed, and they want that exposure that your channel can bring. But, in the early stages, that's not starting to flow in. Jon Shanahan: Oh no, not at all. That's why, when I started, I was like, ‘look, I'm buying all these clothes for work anyway.’ I'm buying all these like nicer brands, but nobody's talking about them, so I'll just make these videos. For the first two years, I had to buy every suit. I had to buy every pair of shoes. I had to buy everything, and I was already going to buy it anyway. This just became a nice way to also justify, ‘alright, if I need to spend $50 more than this pair of shoes, I also need it for my channel, not just for work.’ For the first two and a half years to this day, I can't get attention from any brand. I was like, go buy it. Then, that becomes part of it. That also helped me too. It's like, if I go out and buy the thing, I can say whatever I want about it. If a brand sends you something, there's always that little bit of thing in the back of your mind it's nice, but then I very quickly cut that off because somebody sent me something once and it was so bad, and I did a video. To this day they want to pay me to take it down. I was very able to separate like where this thing came from, and how I got it into, I can say whatever I want about it. Watson: Wow. Do you ever watch the Barstool pizza reviews? So he'll go into a pizza place and he'll buy a pizza, and it'll come out and he'll give it a rating. 1to 10, like 6.8, 7.2, whatever. We do that sometimes just for fun with Piper. If he meets the owner of the pizza shop, and then they're like standing at the door, just waiting to see their views, I feel a lot of pressure here to make sure that this is a little bit more inflated when there's that social pressure. Jon Shanahan: Sure. I can see that. I know my uncle makes all the ice cream, so you can only say so many negative things to them before you kind of like burn that bridge. But yeah, that's funny, right? Pizza reviews, I like that. Watson: So when we think about The Kavalier, creating a brand that a lot of people will go in this direction. As I've seen some of the other Men's fashion accounts that you kind of interact with, they'll create something that might be very on the nose, like men's fashion or something straight to the point, or it'll be like their identity. You made a choice to come up with this word, the Kavalier with a K. It's novel. It's different. You're pulling it in this other direction. I'm guessing that also speaks to kind of the upward potential of this transcending, Jon Shanahan, the individual, but take me a little bit through like where that came from and the aspirations for you. Jon Shanahan: I think it's kind of the reason that you didn't make Aaron Watson's Media LLC to do Piper. The Kavalier is German for gentlemen. K it's an old world, German word gentlemen. I definitely, even at the time, even four years ago, I saw everybody was like, ‘gentlemen, gentleman's lifestyle, like gentlemen,’ this and that. I wanted a subtle way to convey that. I also always wanted to be bigger than myself. I've had other guys on my channel where, you know, it's like, ‘I'm Gabriel in for the Kavalier,’ like that sort of thing. I always pictured it being more than myself because I don't want it to be just about me. I want it to be different skin tones and body types. I have a friend who's come over for, he's losing his hair, so we're trying out different hair loss types of things. I always wanted it to be more than just myself because you know, I think Gary Vee is a very odd example where he's a huge personality. He is his own brand, but then big companies or successful companies are built by teams, and I never wanted it to be, my family's transportation company is Shanahan transportation. It's like, that is a family name versus Sugar and Spice, which is an ice cream store. So, I always lean towards not just being about me, and I didn't want to name it. I could very easily name it ‘Jon Shanahan's Fashion Exploration’ or something like that. Watson: Certainly. Talk about the balancing of, we're talking about fancier clothes generally and larger ticket purchases, relative to many people may never have made on a piece of clothing or a piece of apparel, and the balance of handling or working with, or being used to this higher end product and the efforts to make it accessible to the common cause like I'm someone who has a very limited fashion sense. A lot of the credit for anything that I wear that might look good, goes to Ashley. And when I watch them, your videos, there is a degree to which I'm like, ‘wow, that's like outside the scope of something that I would usually use.’ but. At least I hear it as speaking to someone in my shoes, it might be interesting. I don't necessarily understand it, and being that kind of translator of sorts. Jon Shanahan: Yeah. I definitely found and over time, I've narrowed my approach to thinking about, especially who I was when I was first starting my first job. You wanted to go to Express or Banana Republic or J. Crew, and you wanted to go to these brands that you think are these luxury brands. What happened to me is I bought all these clothes for Edgar Snyder. I bought like $400 worth of stuff at Express, dress pants and slacks and ties. After six months, after washing them, like once or twice, they totally deteriorated. I was so angry at the brand, but I didn't realize at the time Express isn’t the best brand out there. It's just a pricier brand that makes pretty good clothes in the middle of the mall. That's what led me to like Bonobos, who makes at nearly the same price and nicer stuff. What I've now come to really focus on is like the guy, like you, who's just starting out as a young professional, or maybe the guy who has worked for a while and has always let his wife buy his clothes and that sort of thing, and just wants to take like the next step into things. So you're no longer buying like 40 or $50 Target chinos. You want to go just a little bit better fit, just a little bit better fabric and go into there. I've definitely gone into the higher end. I have a couple of suits that are really custom in a couple of thousand dollars, but, if you want to go for your first suit, instead of going out to Men's Warehouse for like 200 bucks, those are okay. If you go to like $500, that's a great suit they're going to wear for 10 years. What I've really sort of honed in on is just taking guys from here's my basic stuff that I always went to, right, just to the next level up. There's plenty of places that do like luxury and much higher end things, but there's really, even to this day, there's still nobody where I'm at, which is like, hey, great, Chinos are like 80, $90. Just go by those, and you'll save yourself money in the long run. That was learning for me too, I bought all this. I bought all these cheap clothes and even until college, I was still wearing all the clothes my grandma would buy me like all my birthdays and Christmas. So, it was never really important until then. That's when I was like, so if I buy this little bit nicer stuff, it lasts longer, it looks better. I feel better wearing it. I look more presentable. So it's, you know, you're definitely like my target audience, which is like, I'm getting conscious of quality stuff, you know, instead of buying a 10 pack of cheap shirts, I can buy these two really nice ones, but they're going to feel better and look better and wearing them and everything like that. Watson: Totally. Another interesting thing has started to happen, which is these meetups that you've done as how you did the one in San Francisco. You're doing one in Pittsburgh a little bit, and just to occupy this different space with your brand. I can remember the first time I did the Summit and like I had an idea that people would show up and like, it's going to be in this state, I hope people come. I have the speakers, but to actually see that manifest in the real world where, because of what you put out in a digital environment, there's now real humans in front of you with context, with a basis for conversation beyond just first base, has to be a bit of a mantra. Jon Shanahan: I started that when I was traveling a lot for work, I'd be in the city and I would just post like, ‘hey, I'm going to be at this bar if you want to come say hi,’ and it happened a few times where guys would come out and be like, ‘I can't believe you're here, it's weird to see in person.’ When I left my job in September, that was the first time where I was like, ‘alright, I'm going to New York for a couple of days. I'm staying with a friend.’ I'm going to meet all these brands, but why don't I also see how many guys can get together? The New York one in October is the first one where like, we had four of my friends that also have channels or Instagram pages. They came out, we talked to a brand that hosted us in their space. We just opened up, the audience said, ‘hey, if you guys want to come out, hang out, say hi, that sort of thing.’ We did New York and then we did DC, and then we did Chicago, Nashville, San Francisco. Then Pittsburgh is on the 26th here. felt bad that like I did all these cities across the world, and I didn't do my hometown that I've been here for whatever 20 years. To take it into the physical space, I also get a lot of feedback from like, especially the Chicago one guys were like, ‘thank you for bringing out other guys that care about this stuff. It's hard to find guys that are interested in this’ and that sort of thing. I could see guys exchanging Instagram handles and everything like that. The San Francisco went well, too. That was a group of other creators opening up the audience. With that one, I worked with over the past couple of them, I work with a brand and say, ‘hey, I'm coming to the city, will you cover the tab if we all go out and that sort of thing?’ That's a really nice way the brand gets a little bit of exposure. We were able to go out and meet the audience. The audience has a nice night out. I'm trying to do more of those because there is one conference in our space where it happens once a year, and a couple hundred guys go. It can be a little bit expensive to get the hotel and everything, but it's like, if I'm going to the cities and I can open it up and say, ‘hey, come meet me. I want to meet you and say hi’ because all day, I'm in my Instagram DM’s constantly. I got a lot of guys asking questions, and I've developed relationships with those guys. I can recognize a lot of guys from the comments. I can see their avatars. I'm like, Oh, this guy has been around for awhile. I like to take that into the physical space because it's probably the most rewarding thing about it. Let alone, I'll get really nice emails and guys will say thanks and everything. I print those out, put them in a folder, but the physical meetups are really nice. Watson: I'm sure. I have a good buddy who is in wealth management and it can be a brutal business at times. He saves a stack of similar nice messages, nice notes that he gets. Whenever there's one of the days, it's a valley, he checks in there and gets some dose of gratitude. Jon Shanahan: I have a lot of screenshots. I have an Evernote note where I'd have screenshots of like nice ones. I haven't had to dip into it for any reason. I've gotten very lucky that I have very little negativity on my channel. Watson: Why do you think that is? Jon Shanahan: I think it's because I'm not telling guys they're idiots. There's a lot of channels that'll say, ‘why you're ugly or, you know, this is why women don't like you.’ Watson: That's clickbaity too. That's like, you know, let me hack the attention. Jon Shanahan: Yeah. I also never want to, or have ever done that, but they'll also say ‘this is why you don't feel good wearing your clothes, get to wear it this way.’ Like, I'm not very prescriptive. I'm descriptive. Here's why I like this thing. Here's why this thing is nice. I'm not really saying, ‘you're a dummy because you bought this thing and come over here.’ I see that cause you know, other channels that I follow, I'll see that in the comments, like I can't believe XYZ, and so I've been very lucky that I get very few personal attacks, block one person on my channel and the past four years. I have other friends with similar sized channels where they'll block and people like every few days. I have developed a thicker skin, but I haven't really had any full on negativity. Watson: Good. Well, this podcast is the change. Jon Shanahan: This is going to be the honeypot for all the negativity. Watson: Yeah. On the front of reaching out to these brands, what's interesting to me is there's a degree to which the brands are studying the accounts and they're saying, okay, you know, whatever tool we may have, like they're above this size audience, we can measure maybe their engagement and other elements. That's one that we want to potentially work with. Then there's the flip side of as a creator, as someone with an audience that you've cultivated, figuring out how to actually create that business for yourself can be an obstacle cause we'll interact with people. As Piper has grown a little bit with different characters and you'll see someone.. Jon Shanahan: Characters is a good word Watson: ..for different characters, but you'll see someone with a substantial account that it doesn't have the kind of minute aspect of business sense for how to actually turn this into a business, as opposed to just a magnet for attention. Then the flip side, you have one with very little, you know, creative chops, not really that substantial of a following, but they know exactly how, whether it's through hustle or through understanding the goal to create those opportunities for themselves. Speak a little bit about that. Cause even the way you can just kind of say offhand, get a brand, to cover the drinks or the tab at an event like that? That's not easy for a lot of people. Jon Shanahan: Yeah. I think that it comes from just growing up and always being around the entrepreneurial mindset. I can, every single long car ride, I can just remember drilling my dad with questions. Like, why is this sign that way? Who's this truck driver, this thing, this thing. I was always very curious. Even just today, I was on a call with somebody talking about this project we're working on. I was like, ‘oh, why don't we suggest, you know, this, we asked them about this thing.’ She was like, ‘I didn't think about that.’ I definitely started out with it from the beginning of like, alright, I'm going to build this as a business and a company. I need to think about it in those terms. I think it is kind of separated, ‘oh, I could spend more time on the creative aspect of things, but I also know that I need to pay for my health care and feed my children and everything like that.’ When you described the difference between the two accounts, I'd punch above my weight on YouTube. I do way more monthly views than a channel of my size should technically do based on my metrics. So, because I set my channel up in this way, where I do so many videos of so many brands, I rank really high in SEO and search. People find my videos and watch way more of them, whereas like a channel, another channel that might have 80,000 subscribers might do like 200,000 monthly views. That's great for them because they do a couple of videos a month. I'm over here doing like three times that. I always start from the beginning of if I'm going to build this as a serious thing, I need to think about the ways that each, each milestone that I grow. I would never reach out to a brand if I had less than a certain amount of followers, because they're not going to pay attention. It's not going to be substantial enough for them in their own mind and also not going to value in a certain way. If a brand looks at you and you have a certain level of engagement, it's like, they're just not really going to give you the time of day. Now that I crossed the 5,000 subscriber mark, that's when I started getting a lot of brands inbound stuff. Half of my inbox each day is as a brand saying ‘hey, we want to send you this thing.’ Now I'm in a really good place where I just basically say, ‘no thanks. No thanks. No thanks.’ Then every once in a while, because there's this pie chart of. Yeah, 90% of stuff isn't really worth my time. I wouldn't present it to my audience. I wouldn't buy myself. I don't really care. There's like this 5%, it's like a maybe, and then there's like one diamond in the rough every time where it's like, this is perfect for my audience. I really like it. It looks well-made like that sort of thing. There's definitely people who go into this and there's a certain degree of luck that they grew. I just had a conversation with a creator this weekend where he's considerably larger, but there's a vast difference in the business sense. He's struggling. If you don't go into it with both sides of things, it's the jobs in wads or the gates. You gotta have both sides of the thing, and it seems like you definitely have that with Hannah and yourself if you got to have the business sense. You gotta have somebody that understands financials, and you gotta have the thing that makes the business churn and run, which has a lot of creativity and the differentiation between things. If you don't have that blend of all of them, it's like, you can be the most artistic guy in the world, but no, one's going to see your art. If you can't get it into a shop, or if you can't walk into a shop owner and say, ‘I want to put this on the wall and that sort of thing.’ My thicker skin came from that sales job where I was like for a month, I would walk into a deli shop and say, ‘hey, what about, how is your credit card processing?’ You had to, like, you had to open up the conversation in a certain way, which was not leading them and understanding that you're a credit card sales person. You'd be like, ‘oh, how like how's business?’ Or ‘what's your most popular thing?’ I can't tell you how many sandwiches or cups of coffee I bought during that job just trying to open up the conversation with the waitress to be like, so who is the owner or where is he at right now to talk to them about your credit card processing. That's where all of the hustle porn, or like entrepreneurial stuff where people want to go and just go do this on their own, I think there's so much value lost in the jobs that you take, that you have no idea how it's applicable to what you eventually want to do. I could never have connected the dots that I would have worked in marketing for Edgar Snyder, sold credit card processing companies, sold B2B predictive analytics software, to now being a YouTube channel. If I was sitting in high school right now and said ‘I want to be YouTube or someday review men's wear, like I never would have connected those dots. I might've gotten there a little bit faster, but I wouldn't be nearly as well-versed in the business side of things, because I would never have had the experience of dealing with a procurement company and knowing the ins and outs of how companies buy software to now come over here and say, ‘this is how you engage with a big brand and the professionalism that's required from there.’ My friends that went straight into YouTube, you can see in the way that they engage with brands, that's not the way you should do it in the business world. There's some value in education you get the degree and get the network and that sort of thing. The amount of learning that you get on the job for something is so underrated. I think, in where we're sitting now, everybody wants to go off and do their own thing, but the amount of stuff that you learn dealing with other people when in a company or dealing with other companies is so important, and you have to take everything that you can learn, even if it's just an entry level job, and you're getting coffee. If you're around the decision makers, and you can understand the mechanics of this is why they went forward with a certain campaign and that sort of thing, I'm sure you experienced that as you did your first couple of jobs right out of school. Watson: That's the reason Piper is who it is now. I mean, to me, the absolute, unfair advantage that I feel like I have relative to other people in my shoes is the proximity that I've had to really high level operators. In the first year that I was doing the podcast, I interviewed this guy, Barry Ritholtz and he's one of the biggest finance bloggers on the planet. I went into his office in Manhattan. Not that I now know how to run his business and I can go do that, but up to that point, I'd done financial services, stuff like that, the like lowest level framework of success and execution. Then you're just comparing and contrasting that to someone who is the absolute highest level operator. It creates a new framework for you, and you probably absorb things in the same way that you were alluding to with your story. They didn't even realize you were absorbing, but then it also just raises the bar. It raises the watermark for what's even possible. Jon Shanahan: Yeah. That's what the creative apprentices don't even realize, like everything. It's not even just the stuff you're assigned to do, it's all of this between stuff, whether, you know, how you interact with each other or how you act and watching you and making sure it's like to put yourself. What did they say in Hamilton, ‘in the room where it happens’ to put yourself around the people that are making decisions? One of the best things I did is when Sandy Snyder came into the Apple store to buy all these computers. I joked with her about her hiring me. I would never have worked for that company if I hadn't joked with her that she was gonna hire me. Then, she put me in the room where she was, I can remember when Google glass launched and she goes, ‘get me a Google glass and figure out how I advertise on it.’ I was like, ‘I can do that.’ I went to my desk and I was like, ‘how do I get a Google glass in it?’ That's the sort of stuff that you have to do, there is a lot of falling into this opportunity, but it's also about embracing it. If I could have got that job and I could have said, ‘I want to be doing a lot more Twitter,’ but Sandy, won’t, let me do Twitter. I'm going to sit at my desk, and I'm going to go on Reddit and search ‘men's wear blogs’ for that sort of stuff. Like I could have done that, but putting yourself in front of that stuff and embracing it and just being like, I can learn so much from this opportunity. I think is what some people don't really want to open themselves up to. Watson: Yeah. So we're going to aim towards wrapping up, and I have a question.. Jon Shanahan: I wanted to set the record for the longest time. Watson: We'll be up there. We'll be in the top 10. What room, if you can get into any room right now, what room do you wish you could get into or would you love to find a way to make your way into, to help you hit the next level? Jon Shanahan: It would help me here to the next level. I have a really curious one, so I did a video on a J. Crew and Mickey Drexler. J. Crew is kind of sliding towards this bankruptcy thing. There's a lot of stuff going on with that brand. I'm fascinated to watch that unfold. I also really like to watch how Sears is kind of navigating this stuff, but to level myself up, it would really be to understand how somebody like the Wirecutter operates at scale. The Wire Cutter started off as like one dude blogging, brought some people in, they started blogging. They were sold in the New York times for $30 million. Now, they operate inside the New York Times. Just as I listened to a lot of podcasts with media executives, and the way that they're thinking about the future of media, because I think of myself as a media company, I'm a media entity. I got to support myself in a certain way. I want to have writing standards and guidelines and that sort of thing. To see a company operating a scale that is digitally native, like, it wouldn't be helpful for me to see Hearst, like Hurst operates L and Cosmo and all this other stuff, but to see a digitally native brand like that to really how they operate and understand today. The Wirecutter to me has always been like the gold standard. Actually, there was an interview where Brian Lamb, the founder, was asked, he was like, ‘oh, so what's next for you?’ He's like, ‘I'm really interested in fashion.’ I emailed him and I was like, ‘you have no idea I'm doing this fashion thing.’ I base it on the Wire Cutter, and I never heard from him. So, he's off on a boat somewhere. Watson: That was a good answer. This was a great interview. Thank you so much for coming in and being on the show. Jon. Jon Shanahan: I have a hundred more than a hundred thousand more things to say. Watson: No, it's great, immediately we'll do a second go round of it, and we'll hit all of those things that you'll remember the moment you sit down. Jon Shanahan: I’ll bring my silver play button next time. I'm on my I'm on my path to get the silver play button on YouTube. Watson: Yeah. I take it. Let's provide the digital coordinates where people can follow along if they want to see what you're doing on YouTube and across all the different channels. Where can people connect with you? Jon Shanahan: I have a YouTube channel where I talk about building my YouTube channel. It's just Jon Shanahan. If you Google that, you'll pretty much find Jon Shanahan YouTube. Then the Kavaliers is the brand around men's wear fashion and lifestyle. Watson: That's what I think. Very cool. We're going to link that and a couple other links in the show notes goingdeepwithaaron.com/podcast is the place to find it for this and every episode of the show. But as we do at the end of each conversation, Jon, I want to give you my one final time to issue an actionable personal challenge for the audience. Jon Shanahan: This one is more for guys, but women, same thing as like, if you have clothes in your wardrobe that you're not excited about, get rid of them, you could replace them, but then also the stuff you have, if you take it to a tailor. You're gonna look really good for a very little amount of money to just kind of upgrade yourself. You will see if you change your personal wardrobe just a little bit, how people treat you differently. I think there's a lot of people that don't want to take that step, cause it's a little bit uncomfortable, but I think if you get outside your comfort zone a little bit, you'll see what kind of you can make. Watson: I like that. The tailoring thing is interesting because you know, clothes are made for like an average or an archetype. I was listening to something about how they did a similar thing with the cockpits of jets and how the design of the cockpit was made for the average sized person, and no one fit into it because there's literally no one who is just the definition of average. So really the tailoring speaks to, you know, even if you are the average height and the average torso link, like maybe your arms are a little long or maybe your shoulders are a little broad or whatever the thing may be. Jon Shanahan: I literally couldn't buy clothes at a store. Which is why I started my channel because I couldn't find stuff that fit, so that's another part of that. You've got to step outside that comfort zone. Watson: Right on. We just Went Deep with Jon Shanahan. I hope everyone out there has a fantastic day. 
For half a century, women wore bras that had been designed by men. Sophia Berman knew there had to be a better way.
She’s spent that last 3 years launching and growing Trusst Lingerie, a company that has re-engineered the bra for larger-busted women. In this conversation, Aaron and Sophia discuss what she’s learned about running a company, how 3-D printing failed to live up to the hype, and how to develop a product and take customer feedback. Never miss one of our best episodes by subscribing to the newsletter.
Sophia’s Challenge; Allocate some time every single day to learning something new.
Connect with Sophia Website If you liked this interview, check out episode 36 with Sophia where we discussed her Kickstarter campaign and her vision for the company. Underwritten by Piper Creative Piper Creative creates podcasts, vlogs, and videos for companies. Our clients become better storytellers. How? Click here and Learn more. We work with Fortune 500s, medium-sized companies, and entrepreneurs. Sign up for one of Piper’s weekly newsletters. We curate links to Expand your Mind, Fill your Heart, and Grow your Tribe. Follow Piper as we grow YouTube Subscribe on iTunes | Stitcher | Overcast | PodBay |
Show NotesFind links and information referenced in each episode. 
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