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About This Episode

This week’s episode features Sharath Cherian sharing about the challenges of creating and building a music content website in around the HipHop genre.  Sharath offers up some perspective the 20 year rise of his very popular music destination site.  Additionally in the episode you can listen to his 5 Top CEO Tips for how to lead through an incredibly diverse run of digital content creation.

Sharath’s Top 5 Leadership Tips:

Below is a summary of the Top 5 Leadership tips shared during the interview this week.  Take a listen to the episode to learn more about the thoughts behind these tips –

  1. Understanding who you are.
  2. Create a powerful vision.
  3. You have to be intelligent. You have to be smart.
  4. Educate from a place of research and experience.
  5. Understanding what you’re not.

We hope you enjoy the episode. You can find even more Full Stack Leader episodes here:


Show Transcript:

Ryan Williams: Not many websites have been around since the pre-Google pre-social media days. But a number of them have managed to not only survive… but thrive. In fact, most of them have found a place in the digital multi-verse and continue to shape the internet as we know it. On today’s episode, I have the pleasure to talk to Sharath Cherian, the founder of HipHopDX. The Internet’s premier news and content site for one of music’s biggest genres. 

As you can imagine he has some great leadership stories and tips that stand the test of time. Internet time. 

So, whether you’re a leader in the world of tech, Or you’re just interested in hearing about how you go from selling mix-tapes to becoming one of the major influencers in hip hop. This will be an enlightening leadership tale for you. 

We’re here today with Sharath Cherian; he’s the founder and CEO at HipHopDX. HipHopDX is the world’s biggest hip hop news website. And, they reach millions of readers every month. Good to have you here.

Sharath Cherian: Thanks, Ryan. Appreciate that. 

Ryan Williams: So you started the website back in 1999, correct? 

Sharath Cherian: July 19th, uh, yeah, 99 

Ryan Williams: What made you get into hip hop? What was the driving force then? 

Sharath Cherian: I was into hip hop since I was a teenager or young teen. I have a habit of trying to get into the business of the things that I like. And so within a couple of years of enjoying it, I was already working for BMG Music Street Team Canada, and I was, just promoting albums.

Then I ended up, or actually before it slightly, before that I’d linked up with a DJ who had a little, a mixtape distribution business up in Winnipeg, Canada, and I was selling 60 hip hop and 60 R&B tapes every six weeks. So I’d already been in the hip hop space for three years just doing stuff.

And so when I stopped doing that work and, I don’t think I was selling mixtapes at that point. I was trying to figure out how I’m going to get free CDs from the record labels still. And then the web, the internet was sort of coming up and I was like, oh, if I just create a website and write album reviews, they’ll give me free CDs. I wanted to pay for them. And my friends would do the album reviews and we’d do news. And so that’s kind of really, you know, in a weird way it was, it was just like a hobby. Just to keep listening to music. I don’t really think there was a big picture there, but at the same time, I knew that in order to make it keep going, I had to, to generate some revenue.

So, we launched in 99 and right away that summer, I took a trip to Toronto to get the labels… universal Sony, at the time it was Virgin EMI and BMG to start buying ads on the website. 

Ryan Williams: Were you able to monetize it pretty quickly? 

Sharath Cherian: I was. I mean, they bought ads for a thousand, $2,000.

Every time they bought ads, it was Canadian, but, it was, it was hard to be consistent about it. Cause I cared more about trying to build the site than they did about trying to break revenue. So I’m always like this, I’m always in this bad habit of trying to make just enough money, and not sort of pursue that, more so it’s just make, just make enough to keep it running, make enough to keep it running, you know?

Ryan Williams: Yeah. I think that’s a tried and true tale from many content creators out there. 

So looking back on the early days of creating the website and thinking about how you got into the market, how you started handling some of the challenges when you had little or no resources, is there a moment kind of early on where you had a defining leadership experience that was impactful and you remember?

Sharath Cherian: Yeah. I mean, I think the biggest story was the first time that, oh, we talked about money a little bit early on and making just enough. I really remember a moment, kind of 2004, three or four, no leaving earlier than that maybe was 2002 where basically I revved up the business a little bit. 

I just got out of college, I thought to myself, all right, I can do this full time and I got into a little bit of debt with credit cards and stuff like that, trying to rev it up. And we started doing websites for other people. And that was a very interesting moment, but it came down to this point where I had to let my coder and my designer go in that summer and basically look at sort of everything I had at that point. Cause it wasn’t really working. It wasn’t bringing in the revenue. So we were trying to do websites on the side. At the same time, we were trying to do the DX website.

 In Canada, with summer jobs, you can pretty much pay for your college, but at the end of it, I just came out with $20,000 in debt, which is compared to nothing to what students come out with here.

But, I had to sort of re-look at it and I had to actually tell my writers who, who our work was paying at the time for the little money we were making, I was paying them. I had to kind of tell them like, listen, I can’t, I can’t pay you guys for a while. I need to pay some of this debt down, I need to figure some things out. I can accrue it and when we, we get some money, I can pay you, I can’t guarantee you it’s going to happen, but, some people stuck with it and some people didn’t, but it was one of those moments where I had the pressure of reality, sort of was sinking in, I ended up getting a part-time job to just start paying things down, um, had to get sort of a loan to consolidate some of the credit card debt.

That was a very stressful year where after that I never got into debt again. Where I really felt like things aren’t going to work the way I needed them to. But I think what, in terms of leadership, what was really great was I was able to talk to people and I was able to get them the money.

What ended up happening was a year down the road. We started making money on the site again so I can just sort of pay back everything that they contributed. So it was really kind of positive. And it sort of started getting me into that understanding of who do I want to be when it comes to money. And, after that, I never really got into debt again, but, and made sure I paid all my bills. 

I have a joke. I’m kind of like a Lannister. I always pay my debts. Um, and that was sort of that experience, where I don’t want that to be something that is ever a hangup, you know?

Ryan Williams: Yeah. Do you feel like the fact that you were able to come back and meet them on that and be a Lannister in that situation that led to people really believing in you, for a longer-term? Did you have some of those people stick with you for a while?

Sharath Cherian: Oh, for sure. I mean, a couple of them ended up becoming full-time employees. Once we got past that hump, and money started coming in probably around 2004, a couple of them did sort of become full-time. You know, before it was for fun. I mean, the chance that the next generation could get into hip hop, which they necessarily couldn’t because they weren’t in New York or Chicago or LA, but they’d got them a chance to be part of it and part of the conversation. 

Ryan Williams: Yeah, for sure. I also noticed that, with a lot of startups, they are able in the early days to build a lot of employee capital on passion. And then there is a shift where it isn’t just about passion, but it’s about is this a real business or not? And that shift can be a hard leadership shift for a lot of newer entrepreneurs who haven’t been in the space before. So it’s an interesting [00:07:00] shift for people to have to move past. 

Sharath Cherian: That’s when I saw eyes glaze over, when I started getting more into like, okay, well we have to make this a business. Do we want this to be something bigger? And how does it influence the music and how do we be more part of the culture. And when I came out to start introducing those, you could, yeah, let me see eyes glazing over or what’s this, you know, why are we doing this? Who cares about our core values?

All those things became really weird, but so, so there was definitely some people who started. They started pseudo-buying into it because at the end of the day, all those core values and the vision and all that stuff, it’s set you up your goals for the year. Um, but then you saw, we saw rapid growth when we really started talking about our goals and what we’re trying to achieve and what we were trying to build.

Ryan Williams: So leadership and tech almost always requires the durability to survive the initial years when you’re trying to build an audience. Not only does a leader have to figure out how to create a technical solution, but they have to discover the team that can help bring that product to life. [00:08:00] One thing I noticed when I was talking to Sharath was his calm, consistent, demeanor. 

After decades of running the website, it’s understandable how that developed. But in those early days, decisions come fast and furious. And you have to be able to maneuver the unexpected. As you mature, however, The game changes. 

So that happened a while ago. Is there a more recent thing that speaks to you in a different style of leadership? 

Sharath Cherian: I mean, we’ve had some exciting things, obviously happen over the years. One of the most exciting ones, and more recently in 2016, we ran our first event that became a series and it’s called DX turbo. And it was a gaming event where we were doing with street fighter five. So we teamed up with Capcom and we teamed up with Twitch and we threw a really cool event where we brought these rappers and gamers together.

And it was a tournament style. We really learned a lot. We were able to team up with a guy named Alex Valle, who is one of the best Street Fighter players in the world of the arcade version when we were younger. But now he runs Wednesday Night Fight Nights in Orange County. And he does many streams on Twitch, they do an amazing job and I was able to team up with him and he had so many authentic connections in the space, instead of us going out and trying to  buy influencers. These are, these are the people who really were the best street fighter players in the world. Or in America at least. 

And we had them team up with these rappers and we had these competitions where it was a rapper and a gamer versus another rapper and a gamer, where the rappers would face off against each other on the team. The rapper, one of them would lose, he’d have to face off against a gamer on the other team. Of course the other rapper would lose and it’d be gamer on gamer. And then that team would go to the next stage. And it was you had two chances of elimination and it was eight teams. And so it was, it was a nice fun event. It was a private event, but we’d stream the whole thing and have one person who is more the hip hop guy, one person who’s more of the gamer guy as the announcers and just kind of chat and have fun.

And, it was a cool event that we ran actually the weekend after E3 during] BT weekend. Um, just because there’s a lot of artists and people in town. So it gave us access to these people. Um, so it was just cool all around. It was a very fun, exciting atmosphere. And we did it three years in a row.

Unfortunately, with the pandemic, we weren’t able to do it last year. But, there was a street fighter the first year and second year we did an NBA, it was an AP jams type game. NBA Playgrounds was called and then the year after that it was Tekken. Um, so it’s been fun. 

And we figured out that the fighting games has created the most excitement versusa sports game. It was a Halo. Yeah. The sports games are hard because you just get the gamer becomes too dominant in it. Um, as well as, the shooter games, um, it’s just, it’s, it becomes a lot more boring.

And so it’s really about authentic experiences for us. It’s really about the fact that we had the best gamers there and we had these rappers and we brought them together so that the rappers weren’t teamed up with just some, just a person who sort of is sometimes the influencers, the Twitch personalities aren’t necessarily the best players right?

They’re more entertainers. So it was really good to be as authentic with people who really knew the game down to the pixel. 

Ryan Williams: That’s amazing. What did it take to merge those two worlds together? Were there any challenges of bringing kind of related, but this kind of disparate worlds in the gamers and the hip hoppers, what was that experience like?

Sharath Cherian: Yeah, I think the challenge is really like, well, what is this what’s going on with it? How’s it gonna work? Finding the right venue where you felt like people were there to have fun and think, but things are still connected in the same way. That makes sure the Twitch stream works, realizing, oh, this type of tournament takes way too long. Let’s not do that again. Cause I was like, yeah six, seven hours versus three hours, you know? 

So it’s definitely challenging, but if each iteration keeps getting better and a little cooler, you know, we thoroughly enjoy it. 

Ryan Williams: Yeah. That’s, that’s one of the things I’ve found about leadership over the course of time is really enjoying the iteration process and getting to a better solution or finding these magical little spots that you get to try something new and riff off of. But really having iteration be a kind of center point of that guidance. 

So many companies talk about using iteration, but it’s a scary spot when managing a business. There’s a sense of faith you have to inject into the process. And sometimes in R and D environments. Having that faith can feel more risky than it’s ultimately worth. I watch leader after leader quietly calculate the ROI on risking true iteration versus fully pre envisioning a project and holding teams accountable to a specific timeline and budget. 

The irony is the iteration guides you to the right product market fit. So it usually saves them time and money. But the unknown can be a scary place for investors, managers, and even the leaders attempting to wield its power.[00:13:00] 

 Because this website’s journey began so early in the Internet’s life cycle. I think Sharath has shown how using it effectively can yield longevity and impact. 

Alright, welcome back. We are now going to talk about some tips that Sharath has around leadership and hear a little bit about some spots that he has been thinking about over the course of time. Maybe we’ll start running down each of these points, we could talk a little bit about them and go into a little bit about what you mean. So point number one, you, you want to share that?

Sharath Cherian: Yeah. And understanding who you are. I think this is incredibly important and it takes time. I don’t think that when you’re younger, but around 25 to 30 is kind of these moments in time where looking back on all your past experiences and really feeling like what do you enjoy? What do you like to do? I like to compare it with a thing called Mazlow’s hierarchy of needs. If every need, your food is provided, you can sleep okay, you’re not worried about your security. If all that goes away, what do you want to do at the end of the day? Or who are you?

So what do you get up really happy to provide or create or, or however. And got to do it in  a quiet space and it really doesn’t take a lot of time, I would say maybe 20 minutes, but it’s really just you thinking about your life and what do you want to create.

And I’ve done it many times. I’ve done it many times. I revisited that concept and for me it’s to create incredible experience for people. Even if I want to have people stay at my house, I want to make sure things are clean and things to have a nice towels and have a nice,, shampoo and that’s how I even actually brought it down to the most fundamental level of, who I was, was thinking about like, well, alright, I’m just having friends over, what do I want to do?

How do I want to set it up? You know? Want to make it look nice. And that figures out who you are at that level, because it’s around friends, it’s about safety. It’s around things like that. And then you can take that and be like, all right, well, how do I envision that into a business or as a leader? How do I make that something?

Ryan Williams: Yeah. And it’s a really foundational element. Like once you have the foundation, you can really grow from it and expand out. I thought it was interesting that you brought up even when you have friends come over, it’s important for you to feel like the place is organized and it’s clean and it’s a nice experience for them. Right? And, you host millions of people every month in this environment where they come and engage with one of their favorite things. 

 What about number two? What’s the next one? 

Sharath Cherian: Well, once you do understand who you are, you, you, from there, you want as a leader, you want to create a Vision, especially if you’re running an organization or a group.

But I think the first thing, understanding who you are develops, what your purpose is, something you don’t really necessarily achieve, but you it’s your north star. You’re always walking towards that. You’re never really gonna achieve an incredible content experience, but you can strive for that.

But then from there, vision has other elements that’s really important. Like, okay well what’s your mission. And my mission is a five to 25 year goal that you want to achieve. So it could be short. It could be long, but there is an endpoint to that.

And then from there you gotta, you gotta create your core values. Like] what’s really important to you. You know, what defines you? I know for me, simplicity’s an important core value to me is to try to make things simple. Even though I have it in the habit of sometimes making things a little harder. 

That’s a huge core value. Making sure that dollars make sense, making sure that things are revenue generating or have potential for revenue generating. 

So those are, those are definitely the things and, don’t get too crazy with the core values. Like after five, it gets, it gets a little much, but these, these are things that you want to not only know about yourself, but bring into your business. 

Ryan Williams: Yep. Makes sense. Is there any special way you like to kind of get back in touch with your vision? 

Sharath Cherian: Yeah, we actually do a thing called cherry camp once a year where it’s like a camp where we come in and really just establish what do we want to do for next year?

So at that point you’re rehashing the core values , talking about them again, talking about the vision, what we’re here to do, what we’re trying to achieve, and then you start and as you’re creating the goals for next year, as a team and as a group, that’s what’s happening.

Ryan Williams: You kind of give people a space to let that stuff come out and be able to share with each other, like having a breakout camp like that. Right? 

Sharath Cherian: Exactly. and also chance not to be on the day to day the same way. 

Ryan Williams: Yeah, totally. 

Awesome. All right number three. What’s the number three for you? 

Sharath Cherian: I think it’s one of the funniest things in business. Sometimes I say, listen, yes, you have to be intelligent. You have to be smart. But if you can get that level, the next thing of really building businesses, “showing up to the party”, but it’s really perseverance.

It’s really the idea that you’re going to be there through thick and thin, and yes, you’re going to get beat up and yes, things are going to happen, but you’re going to keep getting back up and trying something new. You’re trying something again. And I time and time again, that perseverance or that, you know, “you showing up to the party” thing is, is kind of this way of really building your business, you know?

And delivering obviously, it’s not just about showing up. But it’s, it’s about being there and being there with the right time, it’s spending two hours a day on something. Yeah. You’re going to get decent at something, but that’s not going to make you an expert. That’s not going to make you understand fine tunings and things you gotta be spending eight to 10 hours a day getting better and better at something.

And you know, for me, if it’s getting HipHopDX better for other people, it’s like a sport or a topic of education that they’re, you know, going down a rabbit hole on YouTube and on, reading articles on the web. I mean, that’s, that’s what it is, but it is that super dedication to something and showing it. 

Ryan Williams: Showing up to the party. I love that. Awesome. What about number four? 

Sharath Cherian: So it’s educated from a place of research and experience. You know, when you’re younger, it’s, it’s just like, I get really tired of people even reading up about the topic. I want to know your reasoning on how you develop that idea, because I want to know that you’ve factored in situations where that you thought of ways that things could go wrong or go right. And how that’s going to play itself out. Because you know, a lot of it is going to go, right. And a lot, it’s going to go wrong. So you gotta be able to at least thought of a way of getting out of the original 5 to 10 problems. 

Have you developed the idea far enough that,, or that concept, when you’re educating someone. You know, that that actually takes you to a level that’s different, you know, that’s going to change something. So that’s not coming completely from like a gut. That’s when it really bothers me when people have opinions about things and you could start telling pretty quickly that it’s not really based on experience or even research because the research will at least define your thoughts.

Yep. Awesome. I love that. Yeah. There’s a breadth of insight that comes from within all that research, that’s really hard to get if you’re just trying to do it off the cuff. So that’s a great one. All right. Last one, number five. What is it? 

So it’s understanding what you’re not, you know, we started with understanding who you are. I think it’s really important to make a list kinda as you go on with your life, what you don’t want to do or what you’re [00:20:00] not good at, what doesn’t excite you and see if you can, you know, as a leader,, it’s okay to say, I don’t know something, that’s just not the best thing for me to focus on.

Because you don’t want your energy going to something that isn’t something that excites you, it’s not going to help the people around you. And honestly a lot more businesses die of indigestion of ideas, you know, but it’s all about execution and knowing when to say no to things.

And If you understand what you don’t like to do or what you’re not good at then I think you’re going to go a lot farther and it’s going to help people understand what they need to focus on. 

Ryan Williams: Amazing. Yeah. I find that the “no’s” are as powerful as the “yes’s” in being a leader. So tapping into that’s a pretty powerful thing. 

Alright, Sharath, thank you. It was really great to connect with you today. I appreciate all the insight sharing about your experiences, sharing some awesome tips for people to dig into. You’ve built such a great website for people to engage with over the course of a lot of years. And congratulations on that. It’s amazing. 

Sharath Cherian: Thanks, Ryan. Appreciate you having me.