#87: Dan Runcie – From business school to music industry insider by covering the business of hip hop

Dan Runcie  00:00

Coming in as an outsider, even if you're established elsewhere gives you a fresh perspective that others just aren't necessarily going to have. And I think that's what's kept my content, what's kept the positioning of it unique.

Jay Clouse  00:14

Welcome to Creative Elements, a show where we talk to your favorite creators and learn what it takes to make a living from your art and creativity. I'm your host, Jay Clouse. Let's start the show. Hello, welcome back to another episode of Creative Elements. We had a big week of downloads and new listeners from last week's episode with Mitch Long, aka OG Pickle. So hello and welcome if you're a new listener, and welcome back, if you've been with me here for a while. It feels like the show is really starting to build some momentum so thank you, thank you, thank you for sharing the show, for leaving ratings and reviews. We're starting to build some reviews on Spotify now, which is really exciting. It's a new feature so if you're a Spotify listener, please head over to the show page and leave a rating. If you're not a Spotify listener, but you want to support the show, you have Spotify on your phone already, you will need to listen to at least one episode of creative elements on Spotify. So no pressure, I know that's a big ask, especially if you love your podcast listening app but it does go a long, long way. I'm just a couple weeks now into being a full time content creator once again and I am loving it. I have so much more time during the week to invest into improving the show, writing new articles for creative companion and thinking about how to work on the business and not just in the business because that's the reality if you're a full time content creator. It's really, really easy to create a job for yourself. Just keeping up with your weekly or monthly deadlines for creating content is a lot of work. And most of last year, I was just happy if I had something ready to publish when I was supposed to. I didn't spend a whole lot of time thinking or getting ahead. And that's really dangerous, it's dangerous to put yourself on a content hamster wheel ignoring or failing to create opportunities to actually market your work or build distribution. Creators are building media companies and it's really easy to get caught up in creating media and forget to build a sustainable healthy company around it. Modern media companies are a big part of today's episode because I'm speaking with Dan Runcie, the founder of Trapital, a media company covering the business of hip-hop.

Dan Runcie  02:45

Hey, welcome to the Trapital podcast. I'm your host and the founder of Trapital, Dan Runcie. This podcast is your place to gain insights from the executives in music, media, entertainment, and more who are taking hip-hop culture to the next level.

Jay Clouse  03:05

That was obviously Dan on the Trapital podcast but tropical began as a blog and newsletter. Today Trapital's memos, essays and podcasts are followed by the leading executives in music, media, tech and more. Dan says 35% of his email audience works in the music industry at companies like Universal Music Group, Sony Music, Warner Music Group, Roc Nation, ASCAP and more. Trapital has been featured in The New York Times, Wall Street Journal, BBC World News, NPR, All Things Considered, CNBC, and many more publications with more than 13,000 total subscribers. So hearing all that, you would probably guess that Dan has a deep background in the music industry, right?

Dan Runcie  03:50

Before I started Trapital, I was writing on the side mostly freelance and I was doing it nights, weekends and stuff like that, it started purely as a hobby. Because I was in business school, this is back in 2013 and Beyonce had just released her surprise album. And a couple months later, Harvard Business School had released a case study that was a breakdown about all of the marketing that went into this album and how was a surprise launch and you just didn't normally see that type of thing from that type of artist. And that stuck out for me because there was all this earned media that this case study had developed in someone that was actively in business school, reading case studies on New York Times in Southwest Airlines, Disney, all of these blue chip established companies. You rarely saw that about people like Beyonce. So it stuck out to me and I said, you know what, I had been spending all this time writing case studies myself since I've been here in school. Let me do this and just see how it goes because I have some thoughts on so many of these figures.

Jay Clouse  04:56

This is what I love about Dan's story and we talk more about this in the interview, but Dan didn't start Trapital, because he was the most experienced, knowledgeable hip-hop insider, he became an experienced, knowledgeable hip-hop insider, because he started Trapital.

Dan Runcie  05:12

Got very passionate about hip-hop, specifically the business side of it, no one had really branded themselves. There are people that wrote about the business of entertainment, people wrote about the business of music, but nothing about this culture that was so impactful and growing. And that's when I decided to put a name to it. So that's when I had started Trapital and been growing it since then.

Jay Clouse  05:34

So in this episode, we talk about Dan's pathway into writing the Trapital newsletter, why he shut down a successful paid version of his newsletter to focus on monetizing through consulting, what the subjects of his writing have to say about it, and why focus has helped him quickly create a name for himself despite being an industry outsider. I'd love to hear your thoughts on this episode. As you listen, you can find me on Twitter @jayclouse or on Instagram @creativeelements.fm tag me, say hello, let me know that you're listening. And now let's talk to Dan.

Dan Runcie  06:15

I had had moved to San Francisco, this is after graduation and I came out here because I initially wanted a job working in tech. I was working for an ad tech organization at the time, and it was focused on getting broadband to schools. And it was aligned with very much what I thought was the next career path for me. And I was doing that for several years and enjoyed the work. But on the side, you know, I was continuing to explore these thoughts. And as someone that was an avid fan of hip-hop culture and things more broadly in black culture, be able to see the business side of it be able to dissect the marketing plan of someone like Meek Mill, being able to see the content release strategy of Rihanna and how she may have tied it with other things. All of that stuck out to me. And it was hit this nexus point where you know, everything was going fine with the organization I was at, I really enjoyed it. But I was starting to get a bit more recognition for some of the work that I was doing still on the side doing freelance writing at this point, I was writing it for more reputable publications. And then at that point, I had started to see the opportunity in digital media, where people were starting these niche publications on different things. And that's when I said to myself, well, I have a dish focus. And I'm often talking about, I'm getting reached out to about this all the time. What if I was to create the home for this topic?

Jay Clouse  07:40

So you were in business school, and then you started doing freelance journalism or what would you call it more like columns that you're doing these publications?

Dan Runcie  07:49

So the initial start of it, this was after I'd graduated from school so I graduated in May, moved out to San Francisco in June. And I had a post graduation internship out here, I was working for a EdTech organization, I was focused on venture philanthropy, and I had started writing mostly on the side as a hobby. So this was right around the time that medium was starting to blow up. And people were starting to really use it and put their name out there as thought leaders. And I said, oh, why don't I use that for my, for what I wanted to put out there. So I still remember the first thing that I wrote, that I wrote about, it was not even about music, it was about the NBA and it was about some of the championships that some people have won, and how some of those stars are remembered and how they shouldn't be remembered. Not something I'd go back and re-read now, because I probably cringe at some of the writing but I think there were some thieves there that did stick. But yeah, so for me, it was a medium page. I don't even have a name for it at the time, whether it was a blog or what have you. But you know, had my name at Dan Runcie. There was a rolling feed and the stats I could see. But then after, let's say, the third or fourth post, I started to get reached out to by other publications that were like, hey, we like what you're doing this looks really cool. Would you like to get even more eyeballs on it, and you can write on our publication and we'll pay you for it. And I said, alright, I mean, I'm not even doing this for the money but if I can get more exposure, I'll do that. And that's really what was driving it more than anything. At this point, I got into a full time job, I was still doing that. But every you know, few months or so I was able to you know, stay up late and share some thoughts and put it out there. And as that grew, that grew, I started to understand just how this freelance market worked. And it started to snowball into you know, bigger and bigger publications reaching out and then me pitching them as well.

Jay Clouse  09:46

So when you're saying that you're getting reached out to by publications, are you talking medium publications or like the publications that you have some buy lines in, like wired and complex?

Dan Runcie  09:55

So it was both so it was um, so I guess if I'm tracing back there was this one called green label that was under complex, they were the first ones to reach out. And then after that, because I was writing on medium, some of the medium publications at the time, the one was The Cauldron, another was called Backchannel, which is focused on tech, they had seen some of the things that I was putting out. And they had and I think that in many ways, it was a natural segue for so much of what I was already doing on medium. But then it started to go, you know, with a few others. And I had also started to pitch some so for be actually the wired one that was a pitch right at attended this networking event from one of the publications I was writing with, I met someone there that had worked with wired in the past. And then I said, oh, could you connect me with so and so I think they know the editor for the channel that I would love to connect with. And then from there was able to make the connection. And then I had a channel there to pitch them about a few articles. And the first one was about DJ Khaled and his relationship with Snapchat and how I thought there could have been a more official bond there between the two of them. And then the second one was about SoundCloud, and some of the opportunities that SoundCloud had at the time.

Jay Clouse  11:10

This is fascinating. I actually went to college originally for journalism. And then I realized I don't think being a journalist is what I want to do. And I graduated with a business degree. But I have no qualms about saying I learned more and use more of my journalism training than I do my business school training on like a daily basis.

Dan Runcie  11:26

I believe it.

Jay Clouse  11:27

There's just, there's just so much that you learn in terms of just writing like, I'm really impressed by this, because you got to be a damn good writer to get a byline in like wired in complex. And this was not like the training that you had gotten, you would just tell yourself it sounds like.

Dan Runcie  11:43

Yeah, I'll be honest, it was something that I paused and thought about a lot because, you know, you put the first few pieces out there, especially myself, and you have your friends, I would say, oh, wow, damn, this was really well written, and not to knock any friends but sometimes, you know, when your friends or close people give you feedback, it's hard to evaluate that as you know, the same way that you would a stranger in that same type of way. So I was like, okay, you know, I just get you to work and at this, but then once I started to get reached out to buy more publications, I said, okay, I want to get better at this, but in a way that I think can scale and manage. And you know, since it's still some of those purely a hobby, I went out and bought a Udemy course, I bought one of those Udemy courses that was you know, here's how you can write like, you know, the journalists that you know, write for the New York Times, the folks that wrote for The Wall Street Journal, I forget the name of the instructor, but the instructor was focused on this, I took the first course that he did, and then he had a follow up one, and I took that as well. And I was able to learn some things through there. And I think the combination of that, and working with some editors, things just helped continue to grow and grow from there. So yeah, it was not something that I ever really focused on. And to be honest with you was not where I thought things were at all, I still remember being in school, back when I was in high school much more, I got much better grades and things that were math and science related than I ever did anything with, you know, writing or reading or anything like that. I mean, even the SAT scores kind of ashamed to say this, my math score was almost 200 points higher than my verbal score. And so I just never thought that this would be something that was an opportunity for me, but it was one of those things of okay, let me try it, I started to get some feedback, I probably put more effort there into becoming a better writer than I did at any point in my life before that. And you know, luckily, the it resonated with a lot of people in that way.

Jay Clouse  13:38

When did you make the first post on Medium?

Dan Runcie  13:41

So the first post on Medium was July of 2014. Yes, so this was a couple of months after I graduated from business school. So from July of 2014, up until, let's say, February of 2018, it was all a mix of medium. And then after a few years, it was purely the freelance articles for the you know, the wired or the complex pigeons and planes. I was one of the organizations under there had written for a sports one as well called The Sports Fan Journal that were able to explore a lot of the more unique takes, especially the sports ones that delve into hip-hop, as well. So there was the so there was a bit of time between because I think even in those early days, it was still something that was purely on the side, it was still something that I was more so doing as a hobby. And it was and it probably wasn't until that second wired essay that I wrote, that was much more of a strategic deep dive on a company in a music industry, where, you know, I was going out and doing some research and I was like, okay, I think there's something here and I mean, at that point, I was reading folks like, like Ben Thompson and his Stratechery website and listening to his podcast or reading his newsletter, be like, okay, I'm seeing this and I'm also understanding his business model for and I said okay, this there's an opportunity to do this but that idea probably didn't come until 2017. But at that point, I had felt that there was some traction of momentum with my writing. And even some close friends were like, listen, I know that your career was going fine with what you're doing but you have an opportunity to be really unique with this thing that you're doing as well. And I mean, for me, hearing that feedback from people, that's when things really started to click. And I just started to think of the career opportunities as well, because, yeah, what I was doing, I think I could have continued to do, but I would have been one of many people who would have been doing strategic partnerships or business development work in tech, they're a dime a dozen of me that could be at that level, right? However, someone that truly has the lane and being able to own that and the potential, I think that's what a lot of you know, friends and people that I had started to meet along this journey were pointing out to me, and that's when I said, you know what, this other career path will always be here. Now, let's, you know, double down to see what can happen. So yeah, the idea to really go full time into Trapital started around 2017. But yeah, by March of 2018, it was putting the first post out there and building up from there.

Jay Clouse  16:15

Man, for a smart guy who is good at math, you had been looking at like, okay, here's what I can make right now in a salary though, in business development and partnerships at a tech company in San Francisco versus I'm going to go be a full time writer for myself, like, big difference there. How'd that feel to make that leap?

Dan Runcie  16:34

It was, it was a lot, believe me, I mean, because I think in so many ways, at least for me, when you go to business school, you're very much leaving with the confidence that not only will I be leaving here with, you know, a well paying six figure job, I'll be doing it under the impression that I can pay off any of the student loans that I just had, I'll be in a position to fund the life of me and, you know, family and loved ones after that, as well. And at least when I started writing, the idea of starting a company that is focused on this wasn't even the thought, the thought was more so okay, well, this is what writers make, this is what journalists make these publications. And obviously, I think if you are reaching that level, at, you know, even some of the more reputable publications that we all know, maybe their salary was matching what I was currently making at the time, just a couple years before, just a couple years after leaving, you know, business school and working at San Francisco, maybe writing so, so I really had to think about that but I think things started to shift a bit more when they said, no, the opportunity is in, at least for me the best opportunity for this, if I was to go full time wouldn't be to go write for another publication, it would be to create a business around this because I knew that if I do this, there may be future opportunities that I'm not even seeing right now. And I definitely wasn't seeing, but could it become a bit more clear to me down the road, which they are now. And I think part of that, you know, will still continue to evolve. But that definitely was the mindset and the, the the focus there. So it did take a couple of years to get out of that, you know, post, you know, graduate school mentality of making money and just what that return looks like, but the upside was what attracted me.

Jay Clouse  18:29

After a quick break, Dan and I talked about his transition from working in business development and freelance writing, to focusing on Trapital full time. And later, we dig into his process for researching essays, and why he shut down the paid version of his newsletter. So stick around and we'll be right back.  Welcome back to my conversation with Dan Runcie of Trapital. Dan told us that the first Trapital style article on Medium was written in 2014. But it wasn't until early 2018 that Dan really embraced the idea of Trapital as a full time writing opportunity. I wanted to zoom in that time around 2018, when he's beginning to focus more on travel, and what he had built up to that point.

Dan Runcie  19:12

Yes, so at this time, there was no committed focus to owning any type of distribution. It was people that were following me on Medium, people are following me on Twitter. And I'm talking only a couple 100 followers at the time, nothing necessarily to make waves, mostly friends, families, and a few people I had met writing freelance for some of these publications, and friends and family through other social media. So the main things that I felt I had at least that were the strongest were the network that I had made from, you know, other folks I went to school with, or people I had met since moving to San Francisco.

Jay Clouse  19:48

And who was reading at this time because one of the things that really blew my mind when researching you before booking you and even in preparing for the interview. You know, you have a quote from the CEO of SoundCloud on the website as someone that reads the newsletter, like, it seems like the people who are reading at least today are like deep industry people. Was that already the case in 2018 timeline?

Dan Runcie  20:11

So this 2018 timeline, it wasn't the case until I started Trapital. And the difference goes back to that point you made before having to own distribution, it was completely different. It was night and day writing as someone that had my own newsletter under this brand, as opposed to writing as someone that has a byline in Wired. And that may seem crazy, because so many of those pieces in Wired, some of them may even have had more page views than some of the work that I still continue to make do right now for Trapital for some of those, you know, weekly newsletters I put out. But the difference though is the relationship and the quality of the focus that's there. If someone is reading the article on Wired, there's a long chance that they're probably associating this as a Wired article, if anyone builds a relationship, they're joining a Wired newsletter, or they're following up with them on some type of cadence. I don't have that relationship with them. I was a commissioned contractor that was paid X amount of dollars to publish this piece. Here you go, Dan Runcie. Thanks again, let us know where do you have something else and we will maintain all of this property and all the rights that come with it. Writing a newsletter changed everything. I was able to put the blast out there to a few friends, even before I launched anything was just like, hey, coming soon, I'm writing a newsletter about this, it's going to be a bi weekly thing, sign up here. Started getting you know, reach out or not reach out to the time but it started to get signups on that list from people that were working at, you know, venture capital firms, many of the ones that are the biggest ones, people that worked in record labels, people were following, sending it to other people. And I think it was still, you know, a bit of a slow growth in the early days. But probably around the fifth or sixth newsletter I sent out, it was a Breakdown on J. Cole. And that post went more viral than anything I had ever written before for any of those other publications, I had more people reaching out to me after that I was tagged in your social media posts. And I was like, wow so this is what people have been talking about when they talk about own distribution, it's sending them an email, and they're seeing my name with it, and there's a relationship that we're developing with readers. And after doing that for a few months, because the newsletter list was still so small, I was seeing the people that were signing up for the list, I started to recognize some familiar names, some of those names working for many of the biggest companies in music, media, and entertainment. And from there, things were able to, you know, grow and snowball, and I've been fortunate for that. But I think I realized just how valuable that is that even though yeah, the numbers may be bigger in some ways. That's, you know, the most established companies, if you're a writer that is trying to own a lane, having that relationship of the distribution makes a ton of difference.

Jay Clouse  22:58

And when you launch the Trapital brand, it was on Substack, right?

Dan Runcie  23:02

Yeah, so I first launched it on Substack. So this was very early because I remember the end of 2017, I was researching, okay, how would I go about this? How do you put something like this out? And I found out about Substack through Google search, and I emailed the cofounders. I was like, hey, it sounds like you have a beta version of this coming up but can I get in on this? Like I'm trying to put this thing out and they're like, Oh, hey, we're in San Francisco, too. Let's do this, let's actually go grab drinks sometime, let's do it. And then so I got to know them a little bit. And it was ready to have something out. Because I yeah, I believe that they launched in March or February of 2018. And I was one of the early folks to put something out on the platform. And at the time, it was perfect. I wanted something that combined the blog format that I had been used to at Medium, but could send newsletters and just have the dynamic there. I didn't know how to build a website, I didn't even barely understood how WordPress or any of that worked. But it was the perfect tool that I needed that reduce the friction to get things up and running.

Jay Clouse  24:03

And this is so cool. I want to go back to like the subject matter here. So you saw the HBR case study about Beyonce and you're like I could write about that I want to write about that. Were you like a student of hip-hop up to that point?

Dan Runcie  24:16

I would say that I was a fan of the culture up to that point I was someone that loved the music grew up idolizing many of these stars and so many of the business moves that they were making, but it was nothing that I would ever truly see myself doing and it was nothing that I went out of my way to study from a business perspective. Sure, I mean, I remember days when I was much younger going down rabbit holes being like well what really happened to Tupac? What really did this? This was before Reddit back in the days of internet boards and stuff like that when I was still in high school so there's definitely you know some nerd attraction with Vito but a dive deep with some of these topics in hip-hop but no, the true learn the true focus on being a student of this didn't come seriously to that point until the writing, the writing I think in a lot of ways was to manifest a lot of these thoughts or a lot of these conversations or a lot of these arguments in barber shops and stuff like that about what this culture is, what it means and what it can be in the future.

Jay Clouse  25:22

That's so liberating. And I'm glad you said that, I'm glad we brought it up because a lot of creators I talked to, they're like, I want to make something,I want to be a creator. And they go to well, what do I know really well, right now? And I feel like there's an opportunity to go to what do I want to know really well, right now? And how do I start to like build that knowledge base? Which it sounds like, that's the direction that that you took.

Dan Runcie  25:44

I would definitely say so, I mean, because if I was to focus on the things that I do really well, in 2014, or even 2013, I probably would have focused on what won the insurance industry because that's right, started my career, I probably would have talked about maybe the airline industry, because I'd had an internship there and my dad had worked for one of the airlines, I may have probably talked a bit more about ad tech, or tech, or some of the things that I had been learning and picking up in being out here in San Francisco, just just moving here and doing a bunch of networking. But I wouldn't have necessarily established myself. And to be fair, I still don't establish myself as an expert by any means of hip-hop or of music. I think I'm someone that's constantly learning and someone that's constantly being able to share those thoughts but I clearly do have a point of view on that. And I'm continuing to share that but I do think that the curiosity and the desire to not just challenged my own thoughts over time, but to challenge some of the conventional things that others are doing, and not being afraid to do so is what has helped me establish and hone that voice to become someone that people do look to and want to follow for those insights.

Jay Clouse  27:07

Yeah, I think that's what people want. I mean, there are, of course, some people somewhere who knows more about anything, any given topic than any given person, but like, by making the stat the conscious decision of, I want to really make my mark here and talk about this space, that's going to push you to study that space more than just about everybody else. And what we're looking for is like, who do we trust to have a viewpoint that we can align with that we also trust has done the legwork and the research. And I think there's just a big opportunity for creators to choose that lane for themselves and pursue it and not feel like they needed to have a 20 year history before starting that point.

Dan Runcie  27:46

Definitely. I mean, I think that for me, it's worked out well. And I think part of what made me have the traction that I have had is that I did have at least that experience or having that know how do we get in other industries. And I think coming in as an outsider, even if you're established elsewhere, gives you a fresh perspective that others just aren't necessarily going to have. And I think that's what's kept my content and what's kept the positioning of it unique, because now it's in this position where it can be humbling to hear some of the executives that I had known for years and years, will reach out to me or will ask me questions after we talked to be like, hey, what do you think about this? What do you think about what our company is doing? What do you think about this? And it's like, oh, well, a it's kind of this big thing, because obviously just understanding the work I do. It's not that I'm surprised to hear it, it still can just be humbling to be like, oh, yeah, well, this person is reaching out to be in a VM like, Oh, hey, what's my take on this? You know, or why don't you be like, hey, if you ever have any questions about this stuff, let me know, like you have my number, I'm all ears like that kind of, you know, access has been good. But I do think that it helps make the work that I'm doing better to have that context. But then it also just helps bring it full circle into everything else because you understand the point of view that that person's coming from, you just understand, we understand the marketing, you understand how all of these things work, it all starts to click and merge together and just compounds on each other. And I think that's what's so much of this is what does that compound learning? What is those opportunities and I think that's what makes the product itself the content even stronger over time.

Jay Clouse  29:28

Something I admire about your work and other guys like Ben Thompson or Webb Smith, you know, they are doing this research in creating this analysis in a lot of ways about people and companies and brands with a pretty high profile, which I think just takes some courage, generally, you know, you talked about like you wrote a J. Cole piece that went viral. You ever wonder like, what if J. Cole sees this? Is he gonna like it? Is that a thought that enters your mind when you do these pieces?

Dan Runcie  29:54

It's funny because it's something that I have thought about and it's something I thought about more and more because people have started to either reach out whether it's from those companies or those people themselves, or people that work to that being like, oh, hey, so and so read this and you know, shared with a thought. It's one of those things where now you do realize just given the power that the email list does give you from an access and a relationship perspective, I'm clearly writing this in a way where people feel like I am talking to them, and it feels almost like, oh, catching up with a friend to listen to the podcast or to read the newsletter. And I think because of that, it adds to that familiarity with people. So I've had certain rappers or executives, you know, reshare, the post on their Instagram pages or to go, you know, highlight and share things in different areas. And it's like, oh, okay, that's cool. Or someone will reach out and be like, oh, so and so and so and so so don't be the subject, read this and thought this or had this particular take so I've had that. And on the flip side, you know, there's definitely been pushback from certain things as well. But I think what may separate me from others is that the pushback is done in a place that's either rooted with evidence, or it's rooted with some type of proof point about why I may feel this particular way. And it's never to, you know, disparage or to, you know, call shots, because that's not necessarily what I'm necessarily trying to do. But I think in some ways, people even if it's a take that they may decide that they may disagree with their challenges their company, I think it's sometimes they almost can relish in the critique, because it's so different from what they must hear on a regular basis. They're working and they're leading these organizations where there's so many people that are trying to either brown nose, or they're trying to warm up to them or seek approval in some type of way. And okay, yeah, here's this person with this newsletter, this podcast that just says that he thinks that my company is X, Y, or Z. In some ways, it's less of that frustrating. Taylor could be more of that thought provoking to be like, huh, okay, well, he thinks that and I'm sure some people may think that and they may roll their eyes at something, but others may be like, okay, hmm, that's something to think about, and at least, can jog things. And I think for me, some of the better relationships that I have had with people have actually started from times where they've disagreed with something that I wrote a newsletter or tweeted are out. And then that just starts a dialogue between the two of us.

Jay Clouse  32:26

When we come back, Dan and I talk about his process for writing essays, and the opportunity he sees for other newsletter creators today, right after this.  Hey, welcome back. Something that I personally think about a lot is how much social media rewards you for being opinionated, even sometimes incendiary. I personally struggle with this because my default is to not have an opinion about something until someone or some circumstance forces me to create one. To earn a living as a creator, especially creating a media company like Trapital, there is a lot of incentive to create content that takes very strong stances and make strong assertions on topics that you know, others will disagree with. I asked Dan, if he felt the same way about incentives for creators and how he deals with that tension with his own media company.

Dan Runcie  33:15

It's something that I've thought about a lot. And I think that there's degrees to this, I generally think that, in general, even before we get to like, because I'll talk about the algorithms piece, because I think this plays a big piece of it. But even the things that aren't persuaded by algorithms, so just talking about newsletters or podcast, for the most part, I do think that having a strong opinion about things helps because it forces you to have a viewpoint on something and it forces you to do in many ways, deeper research than you otherwise would have. It is very easy to look at a emerging trend or some type of topic or some type of debatable thing and be like, it could be like this, it could be like that, you could see both sides. But that is a very obvious thing that doesn't necessarily make things as intriguing. What I think helps people learn things more from or develop their own thoughts is if someone has the viewpoint and they can either feel like, okay, great, that person helped communicate what I couldn't communicate in that particular way or that person says some things that, you know, I may not agree with, but I think there was some validity behind some of it and at least made me crystallize how I might really feel about this. Getting to that piece of it, I think is going to be much better for you as the person creating things and it's going to be much better for the readers themselves and or the listeners to the podcast or whatever other channel. And that's something that I think has been really beneficial for me and it's something that I forced myself to do as much as I can. So it's less for the algorithmic or any of those things which has to do with how the information travels. But that said, I'm also not immune to knowing that strong and persuasive insights about things, especially if I'm doing my best to be fair, or bring it up qualifications, if needed, do help add to the authority that people do enjoy when they're reading my stuff. The nuance with this, though, is the algorithms, right? Because I think the same thing can be done on Twitter or places like that. And I think this is where you get into people that will do shit posting or things like that just to capture the attention because so much of it is built on that. I mean, I have friends, I respect them a lot, but they've gotten huge followings because of the shitposting or because of the intentional inflammatory content that they're putting out there. But if they're doing that, and they're mixing it in with the insightful things every once in a while, like, that's how they been able to balance those things. So I do know that some of this exists and I think that people find where they are comfortable with it. But for me, I do think that Trapital's voice of being, you know, not just an authority, but be uncomfortable with being able to come back in a future newsletter be like, hey, I thought it was this, I was wrong. And this is what I think I think that just adds to the humility but also keeps the strength of the voice as well.

Jay Clouse  36:11

Do you look at current events and say, okay, here's something that I should develop a stance on or do you wait until something happens that catches your own interests, you have a gut reaction, and then say, well, let me explore that, and that'll become a piece?

Dan Runcie  36:25

I've definitely done both, I would say that I probably lead myself more. And I guess it's for the type of content. If I am writing the weekly newsletter, the weekly newsletter by design is looking at some of the bigger news trends that are happening and me developing and having my take or perspective on it so I do do that. On the flip side, though, and I think this ties into the second piece, I still do write deep dive essays that are built to be more lasting pieces of content or analysis on a particular trend that I think is going to be important and can be referenced back to for some time. And for those I do tend to think a bit more in the horizon, but also currently about okay, who are my readers? What are the things that they are focusing on right now? What are the timely trends? And what are the things that are evergreen? How can that morph into some type of take or perspective I might have? And of course, I have a rolling list essentially, just based on the past content, I've done my perspective on things. So it's constantly looking at how is that change? When new news events happen. How does that fit into my frame of work of the world? Because I think people in many ways may expect what they may get from a tropical piece of content up to this point, which I do think helps. But I think being able to constantly offer that perspective and seeing okay, here's my view of the world, how does this thing come and fit into it? Does it change it? Great, talk about that, if it reinforces a great, talk about that as well.

Jay Clouse  37:58

How much of your research process is deep internet research and sleuthing versus primary sources like calling somebody on one of these companies or talking to an artist?

Dan Runcie  38:09

I would say that when I first started Trapital, it was primarily internet, you know, secondary research. I was researching articles, I was pretty selective in what I was willing to research. But I was either listening to podcasts or I was going deep dive to be like, okay, how does this person think like, what is their mindset with this, and not just trying to react to the headlines, but trying to get that better understanding. Now that I do have more relationships and do have a bit more connections, I'm fortunate to be able to have people I can text or reach out to to be like, hey, I just saw this article put out by x publication. Does this make sense to you or does this line up? And I'm able to get a perspective on that or just to get some take and sometimes be like, huh, I didn't think about it that way, thank you or this this. A lot of those things, obviously, I think have been off the record because of that. But I think that's just part of the access that's been there. I still think that now though, just given the fact that I do have some perspective, it's been able to be influenced there. But I think in some ways the flywheel of this, if you will, is the podcast that I'm able to have itself like no different than like this conversation. I'm able to have many of these same fingers in people and ask them those same questions that have been on my mind as parts of the discussion for the podcast.

Jay Clouse  39:32

This past December, Dan released an episode of the Trapital podcast speaking with Issa Rae, an actress and creator who is best known for her work on Insecure, a show that has been running for five seasons on HBO. But back in April of 2020, he had actually written an essay titled, How Issa Rae Became the Modern Mogul, and he asked her about it in that podcast interview

Dan Runcie  39:53

That actually revised the year you break it down that way reminds me of the synergy map and that essay that I have written a year ago about you and your business and everything you're doing. And I remember when I had talked but only about it. And he was like, you know, I think generally, you know, you got a lot of the pieces there. There are a few things that are, you know, a little different but I think generally you're there. I'm curious, what was your take? What was your thought where you had check that out?

Issa Rae  40:19

I thought it was really cool. He's the one who sent it to me, it was like, look, this is dope, someone sees what we're doing and what we're attempting to do. And I was like, oh, amazing, and I think had the same reactions. Just like, okay, so we also need to be clear, intercompany wise, just like what our missions are, for each division. But it was just, it was really, really validating to see that, you know, you saw the vision.

Dan Runcie  40:42

And then through those conversations that can then inform things, because when I'm talking to dudes, like, oh, hey, well, if you remember when I interviewed Rick Ross, right, interviewed so and so this is what they thought. So this is probably a rough reference on how rappers at that that level or how artists at that level may see that perspective. So I think both those relationships and the podcast itself has created this, this flywheel if you will, of information that continues to reinforce itself.

Jay Clouse  41:07

That's interesting. I hadn't thought about the the role of reaching out to people to basically, like direct your thinking, as opposed to getting direct quotes from them and takes on them. That's a really smart shortcut that should have been obvious that he just hadn't thought about before.

Dan Runcie  41:23

Oh, yeah, no, I think one of the ones that was most valuable, I won't say the person's name, but someone that used to work for one of the major record labels had met him early on in my journey with Trapital, it stayed in touch. And he, I was working earlier this year on a essay that was a breakdown on the major three record labels. And I was like, like, I try to think about this thing that they're doing right now. And I just would love your feedback on it. So I said, I was like, hey, do you mind if I send you a draft of this essay? I'm looking for feedback on, am I understating the strategy and the intent of like, where everything's going, sends it to them, right about like through that we're able to hop on the phone and get some questions answered and stuff like that. So the off the record, you know, direct communication has definitely been helpful to.

Jay Clouse  42:07

So when you were on Substack, you started a paid subscription, that is no longer there. But can you talk about that line of thinking and why you eventually decided to run that down and just make everything free?

Dan Runcie  42:20

Yeah, definitely. So I started my newsletter on Substack, with the intent of starting a paid newsletter, that was $10 a month or $100 a year. And this would be a freemium product, where I would still have the free newsletter once a week and twice a week, there would be a additional update that was on something that was more timely that was happening in the business of hip-hop. And this at the time was a more standard approach, given some of the things we had or at least I had seen at the time from what we've represent a few times. But what Ben Thompson did with his newsletter, and what Substack, in many ways, was pitching as the de facto business model for the people that are using this platform. So I actually had moved my newsletter off of Substack, I had built a website on WordPress and I started using ConvertKit. And do building my own stack was able to offer this freemium content or was a lot for the paid content. The thing is and this is part of the story of why I decided to end it, I decided to move it off of Substack and put it on its own platform because I said, I wanted to have more flexibility down the road, because Trapital could take me and could the business could go places that are beyond the possibilities of what the $10 a year or the $10 a month, $100 year newsletter could be. So I moved it off for that reason, but I still stuck with that vision. And I eventually did it for a little over a year. And I think in so many ways, my goals were aggressive. I was like, hey, I want to reach 1000 subscribers or 2000 subscribers, I can you know, then each paying $10 a month or $100 a year that's, you know, 100k, you know, ARR let's do it. So the thing is, I wasn't close to that and I was probably, I forget the exact number, but it was somewhere around like 200 to 300 subscribers, given the amount of people I had on my newsletter overall, it wasn't necessarily as bad. But I think I just had these high ambitions because I was like, oh, I wanted to convert 10% of the subscribers. I think I only had converted 6% at the time. And I felt like it was this unique product because I was in so many ways, some of the people that are the most powerful music executives, they were spending just as much it'd be just as valuable for my product as my mom was, that just wanted to see me when or my friends rather just wanted to see me would. And I was like okay, the reason that this product works for people like a Stratechery or some of these other websites is because the reach is just so big that because they're reaching so many people, they can justify the fact that they might be leaving money on the table because of just how big the sizes. And plus just the timing, I think what Stratechery is done is just been, you know, in many ways, I think, you know, setting the pace for influencing what a lot of other people have done, including Substack as a platform, but I started to just realize that there is likely a better path in terms of offering a product that can super serve the people who are truly the people that you want to serve with your business instead of this broader thing that's just like, hey, support me. So I wanted to shift away from the support, no, if I'm selling a product, I want to sell something that people need. Sell something that saves people time, helps them make more money, or gets their business to that next level, and a proxy for that and be like, okay, even if it's just easy before, it's just something that my mom would still buy or feel comfortable buying, is this something that one of these executives would feel comfortable buy to help with what they're doing? And it wasn't as binary as that but that logic of thinking helped force me to think about, okay, what are those products? What did that look like? So the first step of that was a few things. One, it was shifting to the newsletter, making it free, because I just knew that that distribution in general was going to help me moving forward. But maybe do some consulting on the side since I was been reached out to about different projects. That, of course, I think is, you know, the hot one of the higher opportunities of this. And then let me start doing some sponsorship in the newsletter as well and offering that and then I've been able to offer more and more sponsorship in the newsletter at a pretty consistent basis and that's been one of the primary revenue drivers for Trapital but do that for the newsletter and the podcast. But then the consulting, I started to do a lot. But I've actually started to scale down from it, because I think it's just something that is just very hard to scale. And it can be very bespoke and time consuming. And I really preferred the nuts and bolts of creating a product that you're selling to many people and can offer it as a business. So now as things are evolving, it's looking more like the sponsorship continuing to be there and just finding the ideal fits for the audience, be able to launch a course in the future and I think there's future plans for investing as well, and that's what really excites me. And I think back to why I wanted to start to wrap it all, even when I knew that I didn't have all the pieces figured out back in March of 2018. Knowing that there was the potential for what I could do, by the access and what I could do through the strength of this email list and this podcast could get me in a lot of ways because of the branding of the audience that's been built. So that's what's driven a lot of it for me and that's the biggest reason why I had made the shift away from the paid newsletter.

Jay Clouse  47:54

What is people's response generally to having ads in the newsletter itself?

Dan Runcie  47:59

I'll be honest, I have not received any complaints from anyone about the ads in the newsletter. That's more from you know, a personal perspective so I can't necessarily speak to what others may experience for theirs but I try not to make it intrusive. I mean, for me by as in the newsletter, it's a brief logo at the top that says brought to you by the small pixel for the logo. Midway through the newsletter, there is a, you know, 150 word copy language that is includes a call to action for that particular company. And I could see the engagement that's there based on the you know, based on the clicks, and based on the metrics, I can honestly say I've yet to hear anyone complain necessarily about any of the sponsors, if anything I've been reached out to by people that may be like, okay, I saw you promote this thing but how good is it really, right? Like I've gotten people that have asked that, but in some ways that is good for the advertisers to know so I always share that but I've yet to get any complaints. I have seen people that have had people complain, like, you know, other peers and friends that have had newsletter sponsor sponsorships, but I haven't done them. I don't want to say as intrusive, but the sponsorship has it taken over the newsletter in the same way that there's mine.

Jay Clouse  49:12

I mean, honestly, I hear way more people say they're concerned about putting ads in their stuff than I hear people who have ads on their stuff, say this is a bad move or that people write that, like everyone seems to be like, yeah, actually, no one cares.

Dan Runcie  49:27

Yeah, it's true. I mean, I've had this conversation with so many people and I'll be honest, there was some hesitancy for me as well doing that just about mindset of doing that first one out there to just be like, oh, how are people gonna feel? Are people gonna feel like, you know, I'm trying to like show them or people got to feel like I'm doing this but I think especially if I reach to this audience that's already listen to tons of podcasts are already consuming tons of media, like, there's this respect I feel of like, okay, well, this person has to make their money and I want to be able to support them to do that and knowing that the same way it works with them, like 95% of the people that read this aren't going to engage with your ad, but the 5% that will, can help make that worthwhile. So it's also making sure that I'm getting advertisers that are aligned. And maybe that's part of it too, right? Like, I'm not necessary, like I'm not, you know, putting ads in there for fast food and stuff like that, right? I'm specifically trying to find companies that can be aligned. Like, for instance, I recently had a, I guess, I'm gonna call it a venture capital firm that was focused primarily on trying to fund creators. Many people that are creators either are reading the newsletter or people on their team work for the newsletter. So trying to find things that I would naturally want to promote is one of the biggest things. And I think that's similar to one of the things I often write about in the newsletter, in terms of hip-hop partnerships, and some of the best ones. You want your artists to be promoting products that you would expect them naturally to wear like Nike sponsors, Drake, I expect to Drake to naturally wear Nike, even if Drake wasn't being paid for it. Same thing goes for Trapital, Trapital sponsoring these firms that are going to help these people, you would hope that I would probably write something about a company like this, regardless, like that is the type of mentality.

Jay Clouse  51:16

Alignments important, I think packaging is important, too. It sounds like you're very thoughtful about how you insert it. Like in this show, I was hesitant about the number of ads in the show for a while and I put a lot of work into making the ad brakes feel native in seamless. Assumptions will just be like, okay, dynamic ad insertion just here is fine. And it's like very interruptive and a bad experience. But I appreciate the listeners listening to this who are okay with the ads and helping me sort of show through sponsorship. One more question about sponsorship, though, how much of it is a poll on your time to manage sponsor relationships and actually getting a copy and putting it in there?

Dan Runcie  51:50

It definitely takes some time. I mean, the good thing is, though, is that there are aspects of that job that can be outsourced. And I'm sure this is something that you probably realize yourself, right? Like, this is something I'm starting to just you know, do more of, and more of each, each growing week, the most critical piece for me is either doing the voiceover for the ad, the ad read, whether you know, however long it is or making sure that the same thing is done for the written copy. But the communication back and forth between people or the agreement around, you know, the logistics and stuff like that, I don't necessarily need to be the one doing that. So how can I help off board some of those things, so I can focus on the piece that is most critical to what I'm doing. And I think that's definitely a lesson for elsewhere of the business as well for a lot of the things that both of us are doing. But yeah, that's one thing I think has been helpful. And I do actually want to go back to something you said earlier about just the comfort of listening to sponsors or how listeners would feel because I think this is a stage of this as well, right? Like, I don't know how many, you know, you feel, at least for your show is the right amount or what you're comfortable with. But I was talking to my wife, there's a podcast that we both listened to, I won't say the name of the podcast, but this is a podcast that we both listen to, that is normally about a weekly show an hour and a half long, and I counted it, they had 10 minutes worth of ads. And that made me be like, oh, wow. And it's part of this network that is also known for having a high, at least in my perspective, ad to content ratio. And then I thought about my show and the concerns I may have had about the much lower ratio, and not that I'm using that as a benchmark but that was a reminder to be like, okay, well, you sit back and think about it, some of the podcasts that you know that actually have ads in there are much further on that path that you might be yourself.

Jay Clouse  53:47

I have 10 ad spots in the show right now. One of them is reserved for cross promos on the network. Two of them are post roll so they very rarely get heard because most people don't listen through to it. But I'm running a listener survey right now and one of the questions is how do you feel about the number of ads? And I have a very small percentage of responders who responded negatively, almost everyone says I'm okay with it, which helps a lot because just having the precedent set of this is the inventory. Sometimes that flexes up, sometimes it flexes down. But it's really nice that like literally today this shows up for a podcasting award, I recorded a 45 second spot and I put it in the pre roll and it's not really gonna feel different to anybody because it's just one less ad that's coming in. It's just my voice instead. So it's really nice, but I think I think there is something about like, setting a precedent so that it doesn't become an increasing surprise.

Dan Runcie  54:37

Right and congrats to you by the way. That's awesome.

Jay Clouse  54:41

Thanks, man. So down in the future, do you foresee bringing back a paid newsletter or having a paid membership as a part of the Trapital ecosystem?

Dan Runcie  54:50

Um, maybe, if I added it, it would be a pretty high ticket but high offering item that was slowly focused on people that were using this primarily for research or people that were using it more for helping their business with their particular needs that they have, and it will probably be a bit more interactive. For me, I've really been a big fan of what, I'm not a member of this but what I've seen Politico do and how they've been able to just separate things. 99% of the people that use Politico only go there for the free site, and they monetize through that. But they have this Politico Pro, which is a four figure annual subscription that is meant for your lobbyist and meant for the people. I really liked that model a lot.

Jay Clouse  55:37

Totally.

Dan Runcie  55:38

I don't know if I would necessarily do that because I still think there's ways to offer value to that audience with one time purchases of things that could be, you know, very beneficial as well. And I do think that there's a commitment level with that annual membership that makes a bit more sense if my team was structured differently. So I think that's something that I'm thinking about right now. I think I do like the model that I do have. And I think being able to have something like courses or investing which are I think, in many ways, bigger ticket items for a very smaller subset of the audience could go a long way. So probably lead more to that path but you never know.

Jay Clouse  56:14

If somebody wants to get started with a newsletter today, what is your best advice for someone who wants to start but grow quickly in a newsletter space?

Dan Runcie  56:22

I would first ask them in terms of that growth, what is it that you exactly want to achieve, right? Because I think a lot of us see the success of some of these newsletters out of scale to millions of subscribers, which is great and impressive and I think they've had good results. But what is it that you want to offer? Like what do you want to benefit from that? Because I do think that growth is growth is great and can be great. But I think it's probably most important thing about okay, who do you want to serve? How many people are in that demographic? And how do you tailor the content to that, right? I think in some ways, the bigger the audience that you do have the probably the more general the content that you offer or the I didn't want to say lower brow but the more introductory or cursory level that the content is, the specific it is or the more deep dive or insider it is, the smaller it's going to be but the more valuable the audience could be. So and there's no right or wrong answer. I've seen plenty people have success with both. But being able to understand that piece, I think could help dictate a lot of the growth decisions that you do end up doing, I think across the board being able to do, whether it's trades or swaps or partnerships with other people is like really effective or I think as you're trying to scale obviously, doing paid marketing and advertising to grow is a huge thing. So many people rely on Facebook and things like that, but first be able to figure that out makes a big difference.

Jay Clouse  57:53

Ever since having this conversation with Dan, I can't stop thinking about the opportunity in front of all of us to step forward and say, I'm going to become an authority on this topic. We get in our own way thinking that we are the right person because of this reason or that reason. But what if no one starts as the perfect person for an opportunity, but they work to become it. This idea has really opened up my mind to the potential futures for myself and my work. And instead of thinking quote, unquote, logically thinking aspirationally instead, what do I want to create? What do I want to be regarded as an authority? And this was one of the most unique arguments against a premium newsletter that I've ever heard. Dan said that he was leaving a lot of money on the table because an industry executive was paying the same monthly subscription fee as his mother who just wanted to support him and that's a really smart insight. There's clearly an exchange of value that Dan is on the short end of the stick if he's pricing the newsletter to be widely accessible, but it's being read by subscribers with a much bigger potential budget. If you want to learn more about Dan, you can visit his website at trapital.co, @RuncieDan on Twitter, or you can listen to the Trapital podcast right here in your favorite player. Links to all that are in the show notes. Thanks to Dan for being on the show. Thank you to Emily Clouse for making the artwork for this episode. Thanks to Nathan Todhunter for making this show and Brian Skeel for creating our music. If you liked this episode, you can tweet @jayclouse and let me know and if you really want to say thank you, please leave a review on Apple podcasts or Spotify. Thanks for listening and I'll talk to you next week.