Dan Runcie on Putting His CEO Hat on With Trapital

Jacob Cohen Donnelly: Let’s start this conversation at the very beginning. What is Trapital and why did you decide to launch this publication?

Dan Runcie: I started Trapital four years ago now, and the main goal was to tell the stories about the artists who were becoming the moguls in our society, the ones who were becoming some of the most influential business leaders. I did that because I felt that the narrative and the discussion around them was lost. These artists have become some of our most successful individuals with the businesses they’ve built, how the trends they’ve started have influenced others, and how other major corporations are following what they do.

It was deeper than how much money they were making. It was deeper than the announcements. I wanted to see the same strategic breakdowns that go through the pros and cons, the same way you would see about a finance or a tech company in the Wall Street Journal or in Harvard Business Review or a place like that. I wanted to see that. I’d actually started writing about the topic a few years back, and it had started on my own personal Medium page.

Medium had grown into writing for a few different freelance publications on the side. That grew into writing for a few more prominent ones. Once I saw the interest was there, I said, “I can keep going at this,” but when I saw where things were going in digital media, I saw that there was a great opportunity to be able to build niche media, and doing that by having more of a branded focus on this and I said, “If I really want this to have a home, it needs to live on its own and not just be in other people’s areas.”

Started Trapital from there and been building it ever since.

Jacob: On your About page, you talk about you started writing about the business of hip-hop as a hobby, and now it’s evolved into a business. Why do you think hip-hop as a genre of music has its own business of category versus, say, rock, or country, or jazz, or the blues, or any of the other categories? What is it about hip-hop that gives it this business of category? Then also who is the target audience for this type of publication? Why are people reading this?

Dan: I think it’s two things. With the first part of that there, the business of hip-hop and hip-hop itself has always been more of a culture. I think that rap has always been more related to the genre of music, but hip-hop encompasses more than just what’s being put out from a music. It’s how people dress, it’s how people talk, it’s how they act, and ultimately now we’re seeing how they go about building businesses and what are the values that they have that stick with them.

I think being able to write about that from a culture perspective has been what gravitated me. I think, as we’re seeing now, over time, hip-hop has become the most popular genre of music, and I think a lot of it just shows the influence that’s happened over the past decades from that front. I think that has a lot to do with it. The primary audience for this is a few folks. The main group is ideally looking at today’s artists. Who are the people that are looking up to the people who are the moguls today?

A lot of the pieces I’ve done and the folks I’ve interviewed are the people who are doing this at the highest levels, whether that’s your Master Ps or your Jay Zs or your Kanyes or even your Rick Ross’s or even folks like Issa Rae, who I’d written about and interviewed, who, even though isn’t directly in music, works more broadly in entertainment, has a lot of these same values as being part of the culture and has her own record label.

I think being able to speak to the next generation of artists who want to follow their footsteps, that has been a primary bucket, but then just considering how influential hip-hop has been, it’s also resonating with the companies that are building businesses in other areas. It’s influencing how people are thinking about the creator economy because so many of those trends come from hip-hop. It’s looking at the companies as well.

The ones that are building direct-to-consumer businesses, a lot of them are trying to think about how best to market their products and they’re learning that from how a lot of these same artists have done so as well. I think as well that also attracts people who work in tech and investing as well because so many of them are always trying to find the next big thing.

We’ve seen that hip-hop has been a kingmaker for so many companies, especially the past decade-plus and people are eager to see who are those next companies going to be. There’s a pretty popular attraction there in that audience.

Jacob: Let’s dig into Trapital and what you offer your readers and listeners. What are the various components of Trapital? If you had to describe the business of Trapital, what is it?

Dan: The core of the Trapital’s business is the content that it creates. That’s primarily through their weekly newsletter where we’re sharing stories on how today’s moguls and artists are building their businesses and also the companies in this space and what they’re doing, what trends they’re setting, but then it’s also the podcast as well.

This is an opportunity to have conversations with these same business leaders talk through what are they doing that’s working well, what are they doing that isn’t working as well, and getting insights there but also talking to some of the other players in this space. There are a lot of executives behind the scenes who have helped shape where things are. We’ve been able to have some great conversations there as well.

With those two things, the content from the newsletter and the podcast, the main way to monetize that has been through sponsorships, so being able to offer a lot of the companies in this space, especially a lot of the rising companies, especially some of the startups that are either trying to acquire customers or they’re trying to find artists themselves to use their services, a lot of them end up becoming readers of Trapital themselves because the content is relevant to what they’re building.

Because of that, they’re also a pretty healthy base for people who could end up being subscribers to the newsletter as well. I think, with those also includes Trapital’s social media presence too, which often shares snippets. I often hear from people, even if they’re catching up with the podcast, they’re catching up with the newsletter, being able to also follow me or Trapital on various social platforms, gives them the snippet of all those.

When I think about the funnel on Trapital and where all those things sit, it’s ultimately the podcast and newsletter in the middle and then everything that’s above that to spread awareness and make sure that Trapital’s doing itself to spread its reach, but then also being able to monetize that through the folks who are currently reading or listening that do want to promote their own services.

Jacob: We’re going to talk about monetization in a little bit, but I want to talk a little bit more about audience. When you think about growing Trapital, getting more people to read the content, or getting more people to listen to the podcasts, what has growth been like? Are there specific tactics you’ve tried that have been particularly helpful to growing the audience?

Dan: Yes. Growth has been interesting because there’s been a lot of things I’ve tried over time that have worked well, there’s a lot of things I’ve tried over time that haven’t worked as well, but that’s part of the game. One of the best things, I mean this sounds generic, but it is the more consistently and high quality the content is that I create and that I can share and distribute. That’s probably the biggest piece of this.

The more that that attracts other people to see what that is and then being able to share that through Twitter, through LinkedIn, through other platforms, and being able to spread that. A lot of that will end up with a– Let’s say that I write a essay or let’s say that I have a podcast, what are the snippets I can share from that? Post that to a LinkedIn post, share that in a few tweets, and then that just helps more and more people see that.

I think there’s a few other things I have tested out as well, whether it’s on Instagram or on TikTok, and seeing how great it can be to help spread that word. Being able to do the same on YouTube as well. When I think about growth, it’s any of those places that are at the top of my funnel that can, at least, reach those people, but also specifically tying back to what we talked about before, wherein it’s looking at the target audience. Where are the artists? Where are the people who are building companies in music that are trying to help artists as well?

A lot of them are on YouTube, a lot of them are on Twitter, and a lot of them, surprisingly, are also on LinkedIn too because this is a genre that attracts multi-hyphenates and a lot of the people that are doing this work also are wearing hats in other places. Especially on a platform like that, it’s one of those things where you do study the trends on how a lot of these platforms do shift over time. Some of them you’ll see things where a place like Twitter, when things get harder and harder to get reached, people will start making longer and longer threats.

Of course, I think we know that there’s pros and cons with that approach, but on the other side, with somewhere like LinkedIn, it’s a little different where you’re attracting a different audience, but there’s a potential there just given some of the content demand dynamics on that platform. Then on TikTok, it’s in this moment where Facebook likely was eight, nine years ago. You’re seeing some interesting things there too but that’s where I’ve been able to get the most of the people that have either joined the list. I think, in often ways, the newsletter ends up being a funnel as well to the podcast, which, of course, I think naturally may have a smaller subset of listeners, but most of them do come from the newsletter. It does just strengthen that relationship a bit because they’re able to hear me as opposed to just reading my voice, which I think makes it even stronger bond for  them as subscribers, but then also their ability to help spread the word to other people.

Jacob: You hinted at things that might not have worked. What are some of the tactics that you’ve tried that just really sucked, they were just not effective at all?

Dan: There’s things like lead magnets that I think got and do get a lot of buzz, but I think the tough thing with lead magnets is that it doesn’t always attract the highest quality of subscribers, especially if it’s not directly tied to something you’re trying to create and put out there. I think sometimes, especially just consider what you put out. The best thing can be, “Hey, this is– ” Especially for something like Trapital, being able to actually share the content you put out and that I put out has been much more beneficial than doing something like that.

I think other things, too. There have been times where I’ve tested out certain paid opportunities and I think there’s a lot of variation on what works well there, what doesn’t. It’s one of these things where I think that there’s a lot of discussion with other newsletter writers about whether or not, when to launch paid, and how best to think about it. I think there is nuance doing a advertisement in a newsletter or in a podcast that is a direct tie to your audience, or you know that the people you’re directly trying to reach are avid people in that, and the cost works out well based on how you roughly would measure how much your costs.

You also thinking about your time and how much it’ll cost you to acquire a subscriber or acquire a listener. I think there is some worthwhile things there, but that’s very different than doing a Facebook ad or doing ads in another type of place, where some of the connections can get a bit fuzzy. You may be reaching people who are largely already on your list. I think there’s some nuance there and I think some of those have been effective, a lot of those haven’t been as effective, but it’s one of those things where you know no different than an advertiser asking it of me, when they’re wanting to advertise on Trapital.

Yes, be ready to ask the tough questions and make sure that you are thinking roughly in your head and what you’re thinking about the numbers, but also thinking about who you’re attracting and how worthwhile that could potentially be.

Jacob: You said, you started at Medium and then moved to your own site. I want to talk a little bit about the technology that powers the business. Obviously, over the past couple of years, there’s been this big proliferation of Substack newsletters and a lot of operators are building their newsletter businesses there. Why did you decide that you had to be on your own stack? Why not use something like a Substack or something like Medium? Why did you feel you had to make that move?

Dan: Well, there’s a few steps to this. The decision to not do as much on Medium, even before I had had Trapital, I realized, early on, how much of what I was basing my metrics or success on was so heavily weighted on Medium itself, and I was essentially just a profile avatar, almost not too different from having something on Twitter. I said, “You know, I think there’s a bit more me to this than just doing that.”

I think Substack was another level of this where, of course, it does give you the ability to have and manage your own email list. When I first launched Trapital, for the first year and a half, it was on Substack. From March of 2018 up until summer of 2019, I was on Substack, and I think, for me, starting there, it was perfect because I didn’t know as much about digital media then, especially as I did now.

I had the idea of the concept and the content itself. I wanted to get going and then it allowed me to be in MVP mode and build out from there. What I realized though with that was, I think, given the type of business that I was building where I knew that there was an opportunity to have a little bit more– not a little bit more, but a lot more branding and emphasis behind what I was doing that wasn’t necessarily allowed on Substack itself as a platform, I think limited what I thought the potential on Trapital could be because I also was thinking a bit more broadly about monetization as well.

At the time, Substack was a bit more focused on trying to have a paid newsletter and trying to have people go that route. That was something that I had actually tried myself for about a year and then ended up sunsetting it that that was off of Substack by the time I had tried that.

I think, for me, I knew that there was just so many other places that Trapital could go, and even though I didn’t necessarily have any product market fit at the time, I knew that there was still a opportunity to do a lot more. I think, as well, when I think about the network effects of Substack, I think the people that have been the most successful that have operated the best on that platform do tend to be people that are talking about tech in some shape or form.

I think that it’s great, I think those are the people that have largely been able to leverage that, especially just given the network effects of, “Oh, if you’re subscribed to this newsletter, you might also enjoy this one”, and where Substack itself is over-indexed on the type of people that subscribe and maybe they’re easier to subscribe to one Substack, if you’re already on others.

I think, for me, reaching a slightly different audience, where that audience maybe is a secondary or tertiary group, not necessarily a primary group, it made more sense to be able to control a little bit more of that destiny. I think as well you think about some of the other things that I mentioned around Medium as well, thinking about wanting to have a little bit more control of the platform itself.

I cover this phase in music. One of the big topics is always been about ownership and not being too relying on a platform with being subjugated to that and how so many artists that we follow have seen both the pros and cons of that and I didn’t necessarily want to be writing about this space and not following the same mentality myself, so being able to own the stack now, which is a newsletter that operates, being able to send primarily through ConvertKit and the website that’s on WordPress, and then a podcast that’s hosted independently through one of the major hosts there.

Being able to have each of those things, but then tidy up. Of course, some might think that it’s a little bit more work, but if you’re running a business, you have to be willing to do these things and keep tabs of where everything is. I think it’s worked pretty well for the type of business of mine.

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Jacob: This episode is brought to you by Omeda. On May 4th, they’re hosting an Omeda Idea Exchange in Chicago discussing some of the most important topics in media. I’ll be there hosting a special edition of The AMO podcast, but you’ll also hear from executives at Access Intelligence, Endeavor Business Media and so many others. Don’t miss your chance to register today. Visit omeda.com and click OX 5. Now, back to our discussion.

You alluded to this about your subscription product. Over the past couple of years, there’s been a massive push by creators to create paid subscriptions, everyone had to have paid subscriptions. Ads are bad, subscriptions are good. You made a controversial decision to get rid of your paid subscription. Why did you decide to make that choice? Talk me through that thought process.

Dan: When I first started the paid subscription, this was summer 2019, I started it because, at the time, that was where my MO was in terms of, “Oh, this is what you do with the newsletter. You turn it on and you become Ben Thompson’s Stratechery, and then everything just bosses after there.” I think, though, as I thought more about it and I saw what the dynamics of it were, I took a step back and I thought, “Okay, here I am asking and ideally targeting in mind that 10% of the audience would come on and sign on for this $100 product that I would be selling them.”

It can be $100 a year or be $10 a month. If I continue to do that, then I have an idea of where the growth of that could be from a revenue perspective. I think the challenge I ran into though, and what I started to think about the bigger picture was a few things. I didn’t necessarily take into account, of course, the time and energy that was then spent to create the exclusive content for that audience, one, and then two, how that may take me away from being able to put more time and energy into the top of my funnel in terms of just be able to grow it as opposed to trying to create the exclusive content.

Then two, even though I think I was still able to get a pretty decent number of the subscribers, the free subscribers at the time, to convert, I think it was around 6%, so it wasn’t quite 10, but I think it was a lot higher than some other peers that I talked to at the time. I just saw the potential for Trapital itself. I saw where things were going, and I said, “If I spent a little bit more time putting more energy into the pieces that I’ve written that I know really resonate, how can I spread those as much as I can, how can I spend more time just making this get as large as it can, and then being able to monetize the content itself?” I think it would work a little better because I think I realized that I was likely leaving some money on the table with potential people with that $10 a month or $100 subscription given what I was building.  It was one of those things where there were some of the most powerful people in music that are always on that billboard power players list, that essentially had the same customer lifetime value as my mother who bought the subscription out of love and just wanted to see me succeed.

As much as it was great to have my mom’s support, I said, “Okay, there’s a bit of an imbalance here because if I, of course, had the right product and being able to think about this in a way, the value that could get out of the relationship with that industry executive could be multiple times that versus what I was doing here. I know it wasn’t just with that person, it was thinking more broadly about what those four or five-figure opportunities could look like.

Not even just from a price perspective, but thinking more broadly, okay, I’m starting to get more inquiries about different things that inform what future products or offerings could look like. Being able to do that, open up my time, open up the funnel a bit, and then being able to monetize through sponsorships instead. Being able to do that in a way where it wasn’t the same as just doing a programmatic ad that just comes all through a website.

It is a native ad. I’m the one that’s writing the copy. It is a tailored message. It’s essentially a marketing partnership more so than it actually is anything that could be compared to a banner advertisement, especially given the engagement and the response and interest from the list that I had. it made too much sense. I think so far the response has been pretty strong and consistent from the people I’ve been able to work with on that.

It’s been a good model and I think it even becomes more valuable given the fact that I’m targeting and talking to a specific niche that I think that is obviously getting a lot more and more attention as the years come and evolve with where things are going with both creators and with artists.

Jacob: I think one of the interesting things about the subscription business is, and especially if you’re selling annual subscriptions, is you almost feel trapped to continue delivering over and over because you’ve received money, but now you have to deliver value over a year. I don’t remember which publication wrote about it, but they wrote about how there are a lot of creators who feel as if they’re stuck, they can’t get out because the annuals just renew and renew. Talk to me about how you sunset that product.

How did you shut down the subscription where everybody felt as if they were being fairly dealt with? What did that look like?

Dan: I did it in a series of emails. I first sent a email just to let people know, “Hey, this is where I am at, and I’m thinking bigger picture with this. I know that a lot of you did this out of support for me. I know a lot of you did this out of wanting to get the additional content itself, and that’s great, but I didn’t want to build a business that was based on the patronage mentality where that was the primary needs of the revenue generation.”

I think that works if you at much larger scale, someone like a Ben Thompson as you mentioned earlier, but I think it’s a little tougher when you’re a bit more niche focused. I sent the initial email out, had gotten a few responses from folks to be like, “Hey, we’ll stick with you regardless,” but I said, “No, this is something I need to do.” When I did it, I gave a refund through Stripe prorated for everyone that had bought a subscription based on when they had done it before.

It definitely hit the bank account quite hard at the time, as you can imagine, but I knew that it was the right thing both morally and right to do. I know I’ve seen others that have handled it differently and everyone can do as they choose, but I would not have felt good just taking up money. Even though there was about three or four people that did follow up to be like, “Hey, keep the money or keep my share of the money, what you gave me is too invaluable for this. Just want to see you support X, Y, Z, and then we continue to, at least discuss offline.”

Anyone else, no, they all got the money back there. Then I also sent a broader email out after I had done that to everyone else with the free Trapitalist to be like, “Hey, I made a decision. This is where I’m at.” I spoke pretty openly, sharing the same story I’m sharing with you now about why I did it where I’m at and where I see as the potential there, and then, at the end, to capture some of the attention as well.

I did have a call to action to be like, “Hey, well if you’re interested in sponsoring Trapital, hit me up here, and let’s talk.” It was interesting. I remember I shared, I posted a thread on Twitter about it as well and it got some attention at the time because this was also around the same time, because I know we’re in similar Twitter circles, that people started to chat more and more about these ads versus sponsorship, or not ads versus sponsor, but ads versus subscription revenue. Was one good or bad being able to do both?

I think it added a bit to that discourse as well when I made that decision. Ultimately, I wanted to make sure that people were compensated or reimbursed fairly and then that I was as open as I could be because I felt that was the best thing I could. The way I ironically framed it, I was like, “I spent all this time evaluating other people’s businesses in Trapital, let me use additional Trapital to evaluate my own and put people behind the scenes with one of these decisions.”

Jacob: Let’s talk a little bit about the advertising products you offer. You’ve talked a lot about sponsorships. Are there other things that you also offer to potential partners?

Dan: Depending on the partnership, there are a few different opportunities I’ll offer as well. I’ll do webinars, usually around once a quarter where I’ll make it an event where there’s a partner that wants to have one of their executives from their company and we’ll talk a bit more deeply about the products that they’re serving or how they want to serve either artists or creators or someone that I think is in a similar group to who I reach will create it where we’re making a digital event out of it.

I’m attracting the folks in and sharing it through social media, sharing the newsletter, and the podcast. People can come on, sign up for the webinar, and then they can follow up with the people who sign up for it as well. That’s normally a value add that’s included with other packages in case it aligns with there, but that’s the majority of what it is outside of Trapital itself, and the monetization from the newsletter, and the podcast I’ll occasionally do, speaking opportunities or short-term consulting opportunities as well, but that’s more me separately as opposed to just the revenue through Trapital.

Essentially, it’s tapping into the same interest where people want to have these insights. It was something that I did more heavily back when I first shut down the subscription, when I was starting the sponsorship, wasn’t quite sure how much was going to come in and you wanted to make sure that there was enough revenue that’s there.

I slowed down on a fair amount of those but I think as time has grown and evolved with each of those and likely as I think I’ve gotten a just more knowledgeable about the industry and the space and being able to share great insights with folks, but then also as a podcaster and as someone that’s speaking about this topic, have a bit more topics that I can tap into, can be a bit more selective about the opportunities that I do take on there.

Jacob: I think, for a lot of creators that are first getting started with the whole concept of selling ads, figuring out what to charge can be a little daunting. How did you determine the rates for ads on Trapital?

Dan: I did a fair amount of research. I looked at places like Swapstack and Paved, which are marketplaces for newsletter advertisers to get a sense for what people are buying at, what people are selling at, who are the people that are buying those things, and how that may relate to my niche. Knowing that I’m owning a space that people aren’t necessarily in as much, I wanted to see what it was like, especially with some of the newsletters that have come in this– I’ll include myself in the Substack wave since I did start mine on Substack.

I also looked at what are the rates for some of the other newsletters that were before me, but still in the music industry space, getting a sense for, well, what are they offering, how is their cadence? They have daily newsletters or they have three times a week or theirs might be less editorial and less insight-driven and just more newsworthy, how does that shape out there?

I think, for me, that was able to help create a baseline and ultimately it was testing it out, seeing, “Okay, this is what the rate is.” Some people say no, some people say yes, but is there an effective close rate that makes you confident in the ability to continue to close more business moving forward? If everyone’s saying yes, then it’s probably too low. If not enough people are saying yes that you have plenty of empty inventory, then you probably need to adjust there. Then just being flexible where there is a price floor that you may not be willing to go lower than and being able to be confident with that. Then also understanding, how does this change over time? I know these are conversations I’ve had with you as well, getting  your insights on, “Hey, this is what I’m thinking for price, what do you think?” You would offer some stats based on what you had seen, not just whether it’s at CoinDesk or other places, but from talking to others and getting a sense for what those rates are.

I’ve taken it as more of a flat-rate perspective but there is a CPM that is roughly baked in there given the growth of the newsletter and the podcast over time and then thinking about what bundles can look like and ways that you can make it even more value-additive than just thinking about a standard 32nd pre-roll or just the standard logo that’s put in a newsletter.

Jacob: One of the downsides of a creator-led solo operation is, well, there’s two really. One is we are the brand, and the brand is very linked to us, the individual. Also, we’re stuck doing everything by ourselves. As you’re working on Trapital, what is the breakdown of creating content versus selling ads? Do you have any resources that you lean on to help you handle certain parts of the business?

Dan: I do. This was something that happened in stages for me because these are all hats that I had to wear, especially in the early stages. It was a lot, especially then because you’re trying to do all these things, you’re trying to get them going up at once because I knew that I needed to look at all of these tasks and then look at it and say, “In an ideal setting, if things were the way that they could work as smoothly as possible, would I need to be the person to do this particular thing?”

I think it forced me to ask myself that question was helpful, especially thinking about it in a few areas with the actual production of a newsletter and the podcast and all the assets that go into it. Taking that away from the actual content itself is one thing if I’m the person on the microphone or on the camera doing the interview. It’s one thing if I’m the person writing the content, but after that, can I get help to do all those, the rest of it, to push this over to finish line and send? Yes.

The more that I was able to grow, have more revenue come in, was able to have help on both of those fronts. Being able to work with a production team that does help with the newsletter or that does help with the podcast assets itself, both with video clips, posting on YouTube, editing, all of that, and being able to help distribute it, that’s been really helpful.

On the newsletter side, being able to work with an executive assistant that has been able to help with some of the production around that and also around the newsletter specifically, but then also other administrative tasks as well. On the ads piece of it, being able to work with a company like Smooth Ops, some of the former folks that were leading growth in advertising at Morgan Brew, and being able to get their insights and being able to learn from how they’ve been able to sell ads there and then being able to have them help Trapital and do the same.

Each of those things have been really helpful for me to be able to work with other people who, in many ways, are more skilled at doing those things than I necessarily was myself. By being able to do it in a smart way just allows me to leverage more of my time for the things that I can be doing more effectively.

Ultimately, it’s always going to be a grind because I think, like you said at the beginning, in businesses like this, I’m always going to be the one, for the most part, that is wearing at least or at least being aware of most of the hats that are happening. I think as I’m wise of thinking about how Trapital grows, how Trapital continues to evolve, continuing to ask myself that question with each part of it.

How much of this thing that I want to do or I see the vision for has to be done by me? Also, by being able to bring in a lot of those smart partners, they can unearth other ideas that I may not necessarily have thought of as well. I think it’s so easy to get caught up in the minutia or get caught up in the day-to-day things that even though I may know what the big picture may look like, execution is still a ton of work.

Being able to make those types of partnerships or future hires or contractors or things like that, I think is what helps Trapital continue to scale because I’ve seen the potential of what it can be just myself. Of course, it’s doable, been able to be profitable, been able to do all the things that I want to be able to do, from that perspective, but I know that there is plenty of opportunity to continue to improve on that, and then continue to iterate.

Jacob: I mentioned the brand aspect. With a media operator, for example, it is 100% linked to me. People know that they’re reading Jacob when they read that. I imagine it’s the same with Trapital.

The downside of that is, if someday you want to stop, you have to make a choice, can you sell the thing, which is probably not very easy to do because a buyer would want to keep you and therefore you’re trapped anyway, or you just have to say, “You know what? I’m done, I’m calling it quits”?

Have you thought about how you disconnect you as Dan from Trapital? Is that even possible? Do you bring on other writers? Do you bring on other podcasters? How do you, and have you, thought about that part of the business?

Dan: It’s something I’ve thought about a fair amount, and I’ll take it in two steps. The first step is, yes, I definitely see a future where I can bring on other writers and I can bring on other podcasters because I think there are so many subsections of this area and of what Trapital’s been able to grow, and so many things that I want to be able to do more of even if it’s not me the one leading it just to orchestrate and help make that happen.

I think there’s a huge potential for that. I think the more that Trapital can grow, the more that can happen. The place where it gets tough though, and I think this is what you’re alluding to is that even if Trapital becomes that growing network, it is so hard to be able to disentangle that, where if the person wasn’t there, it would take a lot of it.

Look at some of the media moves that have happened in the past two years. You have Spotify buying The Ringer and you have Penn National buying Barstool. Let’s say if Bill Simmons or Dave Portnoy was like, “Hey, after this sale, I’m out, I can’t do this anymore.” I don’t think those sales numbers would’ve been as high because part of the attraction is those people.

Bill Simmons podcast is the most popular podcast on that network. I’ve never seen the stats but I don’t need to because I feel that confident in it. Maybe it’s a little different for someone like Dave Portnoy, where I think the most popular podcast there isn’t necessarily led by him, but his aura, the difference there is though he isn’t the CEO of it. It’s a little different.

He was able to do some of it, but he hasn’t necessarily stepped out of it. I think something like that does take step stages to be able to get to though. Even at that level, I think it’s still tough. I think we’ve seen the same things that happen with artists as well. I’d actually interviewed this guy Ib Hammad who is the president of Dreamville, which is the record label that J. Cole is signed to.

I asked him this same question because he said that a lot of his effort right now is built on how he can separate the Dreamville brand from J. Cole, even though J. Cole is so synonymous with the company. He said, “We’re trying, but it’s tough.” The tough thing is, it’s the same exact thing. I think there’s a future where J. Cole may no longer want to rap anymore, but so many people think J. Cole is Dreamville, and how do you do that?

I think it’s been tough where I think maybe the most effective thing we’ve seen is where the lead person steps away from the CEO role and they let someone else come in there and do their work. Jay-Z isn’t the president of Roc Nation, he has someone else there but he can still be the lead figure to come in and help close deals or be connected with it because it is part of his ethos but he could still do his other things and maybe someone like a Portnoy fits that mold to some extent as well.

I think it would be interesting to see what that could look like for a Trapital down the road. I do think it takes some time to get there, but I feel like that’s the most effective balance I’ve seen of that model.

Jacob: Let’s look a little in the future. What are some products or features of Trapital that you might want to build, and what does Trapital look like over the next, say, three to five years?

Dan: For me, the next big thing that I would love to build for Trapital would be an investment arm to be able to back the companies that are going to be the ones that either artists or creators or people that ultimately are going to be building the future of entertainment and media and in the content space, being able to back them the same way that, in the past decade, we saw companies like TikTok and Snapchat, and Cash App really go from good to great and have their growth accelerate because of hip hop. I want to be able to have a fund that invest in those same types of companies. I think something like that does take work to get up to, but for me, being able to do that, and then have the content for  Trapital essentially be the brand differentiator and the lead gen for a fund is something that’s out of the roadmap. I think we’re seeing now where there’s plenty of existing funds that are now stepping up all their media platforms and work, whether it’s Red Point doing what they’re doing or it’s Andreessen Horowitz doing future, they’re all going to do something. They’re likely all going to have TikTok soon enough before we know it.

I think that Trapital’s advantage is that it already has the brand, it already has a lot of these same folks who are in this space as well, that are already reading and listening to Trapital. There’s a network there to be able to tap into both with co-investors and then with the other startups as well for deal flow. There’s a great opportunity to be able to do that effectively.

Then I think, for me, thinking this out, this can lead to a pretty efficient team where let’s say that there is a team of somewhere could be 10, 15, but maybe not even that much, where there are a few people that are really the strong people focused on content. There’s a few people that are helping things out from the investing side. There’s a few people that are helping with ads and operations and marketing future opportunities as well.

Then being able to have an a COO and then a CEO being able to lead the way. I think that that is a very doable future. I think when I think about what the next few years look like, being able to have that and then the revenue that comes in from sponsorships or any other type of events or activations or opportunities is the short-term flow. Investing is the long-term flow. That’s what excites me about where the Trapital could go and what it looks like.

Jacob: I want to close with the same two questions I ask every operator that comes on. First, what is a mistake you’ve made in your career and what did you learn from it?

Dan: A mistake that I made in my career. Well, I’ll start with Trapital. I waited far too long to sunset the subscription product that I had, and I made that mistake because I had gotten married to the emotional feeling of what I wanted the success of the product to be and how meaningful it felt, at that time, as a creator, to be like, “Oh yes, someone bought this, that means I’m doing something good, I got to keep going,” as opposed to the CEO hat that ultimately made the decision to be like, “Okay, big picture here, this is where we’re going and this is what we need to look like and we need to think about how this may limit things.

Thinking about the bigger picture as well because any of these other companies that I may have looked at that I think may be doing well, they’ve all had things that they’ve sunset at points because they didn’t work. They are only in the positions they were because they made things work well. I think, sometimes, as creators starting out, because you aren’t necessarily just wearing the CEO hat, you’re also wearing the creator hat, where you get the same dopamine hits from the engagement and all those things, being able to separate that from the bigger picture–

I think that I knew, four or five months in, that I probably should sunset this and I waited seven months after that to do it. Not that I think it was the worst thing in the world because, obviously, I was able to turn things around and the businesses running now, but time is money and who knows how much further I could have been in the business had I just switched things there and done it. Could I have been seven months ahead? I’m very excited to see what seven months ahead from now looks like.

I think about things like that and I think I’ve kept that in mind as I’ve stayed too connected to one thing. I think, for anyone that is listening to this, whether you are either, A, a media operator yourself, or the lead creator for a media operation, especially if you are the same person, think critically about which side of you is the one that feels the connected to the thing that may be making it tough to make a decision.

Hopefully, that can add you some clarity so you can save some time and not let your indecision just lead to the lack of being able to actually make a move when you need to.

Jacob: My second question is, for others that are thinking about launching their own publications, what is some advice that you would give them?

Dan: The biggest advice I often give to people is to start with a niche and start with the true niche. Even if you think you have to get more narrow, do it because I think that’s how you stand out from it. Even if you may evolve over time, that’s where you get it. Trapital resonated with people because there were plenty of people that may have been talking about hip-hop, there are plenty of people that may have been talking about business, or even the music business, but there wasn’t a place that said, “This is the business of hip-hop. Here we are.”

I think, being able to have that, just like you said yourself in the beginning, people understand why that’s a thing, but it still wasn’t clearly be like, “Okay, this is where we talk about this thing,” and being able to niche down from that perspective helped.

The unique thing is that, over time, because of how many more niches of things are being created on places like YouTube or TikTok or whatever, it will create the opportunity to need to do even more of that. That isn’t necessarily a bad thing because your team and the market can grow over time, but it takes time to get there. Whether you’re thinking about Facebook starting with Ivy League college students and now it literally is trying to attract everyone in the world, keeping that and keeping that mentality in mind.

Always start niche because I think, sometimes, I get it when sometimes people will pitch me on podcasts and I’m always thinking about, “Okay, well who would be the audience that I’m reaching on this podcast? Or how do I fit this profile?” Sometimes, people would just want to, “Oh, we just want to talk to unique business leaders doing their own thing. I see you post on social and it’s a unique thing,” but no, I think the more that you can get specific, not only will that help you attract others to your business, but it’ll help you stay more grounded in what you’re doing, what your mission is, and what you’re ultimately trying to build towards.