386 Men’s Fashion Reviews, YouTube, and Building a Brand w/ Jon Shanahan

In the past, magazines like Vogue & GQ were exclusively at the epicenter of fashion and style. They alone could play kingmaker to the tastes, trends, and brands clothing of an entire culture.

Today, the influence has been disseminated to a broad swath of creators and media outlets with their own perspective. Jon Shanahan saw this opportunity coming and has staked a claim with his brand, The Kavalier.

He started a YouTube channel more than 4 years ago and now creates content full-time reviewing menswear.

In this conversation, you’ll learn how Jon got started, the intentional approach he takes to his style, and the patience & discipline required to break through.


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Jon’s Challenge; Throw out the clothes in your wardrobe that you’re not excited about. Tailor the clothes that don’t fit just right.

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Connect with Jon Shanahan

Instagram
Website
The Kavalier on Youtube
Jon’s 2nd channel

If you liked this interview, check out episode 318 with Brad Driscoll where we discuss building a following on Twitch, starting an SEO business, and the value of persistence.

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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.