Exclusive Interview: In less than a year, Joe Pompliano has turned Huddle Up into a six-figure newsletter

Business of Business: I was reading up about your career. And it seems you've had a pretty interesting trajectory going from sports or talent management with Octagon, to being a financial analyst at JPMorgan, to doing what you're doing now in content and media. Could you talk about your experience and what led you to where you are now? 

Joe Pompliano: First of all, thanks for having me. I appreciate it. And second, yeah, let's start all the way back. So for those listening that may not be familiar, I have four brothers. I grew up in North Carolina. And what that afforded me was basically like — I always joke that we didn't watch cable news growing up. It was SportsCenter all the time. ESPN, all that type of stuff. And we played every sport you could imagine. Basketball, football, baseball, etc. And I think unlike someone else in my position, I realized pretty early on that I wasn't going to be a professional athlete. So that was kind of thrown out the window. So I did what I thought was the next best thing at the time, which was to set my goals on being within sports somewhere. And I thought, originally, that I wanted to be a sports agent.

I went to High Point University in North Carolina, and I got an internship at Octagon Sports Agency, which you mentioned before. Octagon is a full-service representation agency for all athletes. It was 2015 at the time. So all these social media platforms were obviously around, and some of them were just beginning to take off. But I think really, athletes were learning the importance of what these platforms could do for them and their brand and their image and stuff like that. So we worked with athletes like Stephen Curry, Rudy Gay, all of these guys to really just build a brand on social media.

I got an opportunity to go work in New York City in financial services. I started at a smaller firm at first and got experience for a couple years. And then like you mentioned, I moved on to JP Morgan. So I was an analyst at JP Morgan on the fixed income side, on wealth management, and then I worked as an associate there. Incredible experience, again, and obviously a great, reputable firm to work for. But really what it just came down to was like, I didn't see myself doing this long term. And I always thought to myself, like, “Hey, can I see myself, two or three positions higher than I am now?" But I just didn't see myself living that lifestyle doing that same career path for 30-40 years. I really just pivoted and said, “Look, I want to get back to what I really enjoy,” which doesn't feel like work, which is the sports side of things. But I still love that business aspect of it, too. I found myself asking more and more, “How are the Kansas City Chiefs able to pay Patrick Mahomes $500 million? Why is Amazon spending a billion dollars on the NFL Thursday Night Football game?”

So taking [those questions] into account, I really looked at the landscape, and I went back to this core belief that creators are going to be the future of media. The guys or girls that are personality-driven and have that mutual relationship with their fans — I always thought was very important. I thought that there was a really big opportunity to do it for a younger generation and someone my age, to come in and create unique content, and give people a different analysis. I think there's a lot of sports business publications and journalists out there like that, but it's really just a unique spin, right? I like to think that my original approach was that some people are really good at the business writing aspect of it. And then some people were really good at the sports side. But there were few people that I thought were doing really well meshing them together. So with that in mind, I started Huddle Up. 

"I don't think I had some master plan, right? I just strongly believe that individuals were the future of media and legacy media organizations were in trouble." 

Huddle Up started in July of 2020, so we're coming up on a year here. When I first started Huddle Up, it was really just taking interesting articles that I had read and posting them in email, giving a little bit of my opinion, and then telling people to go read it themselves. It wasn't even like some grand plan. I found myself continuously showing people different articles and being like, “Have you read this? Have you done this?” And everyone would be like, “No, dude, I haven't. You're the only one.” It slowly evolved over time, and I started writing more. And then I took the links out, and I was doing original writing and stuff like that.

The way I thought about it was that the one differentiating factor is your opinion, right? It's the one thing that people can't replicate or to like no one else has. So I always try to do a little bit of “Hey, look, this is what's going on, why you should care, the facts you should hear.” All that type of stuff. And I put more of an opinionated spin on it. There's obviously going to be people that don't agree with what you're saying, and that's totally okay. I'm pretty open and honest about the teams I'm a fan of and my viewpoints on certain things. And I think over time, your audience kind of caters to that, right? Because people realize, “Hey, Joe really believes that college athletes should get paid.” And if you're really against that, maybe you're not going to be a fan of my writing. Or maybe you're not going to be a fan of the newsletter or my Twitter account and stuff like that. So I think the audience kind of filters itself out to some degree with that. 

I really just focused on Twitter and the newsletter to start. I use Twitter as a funnel. So I was attracting as many followers as I could on Twitter, and then trying to funnel them down in the newsletter, where I kind of own the email addresses and can reach out to them proactively. It started slowly. My brother has a large online audience, and we started leveraging that a little bit. The one thing that was super helpful in that sense was threads. If people started on Twitter today, I think they might be overwhelmed to some degree with the amount of threads going on. And to be fair, I jumped on Twitter last year. So I don't know to what degree they were going on previously. But it certainly feels like they picked up a little bit and everyone's using them as some type of... I don't want to call it a growth hack, but you know, they're trying to build a following or filter people into newsletters or whatever it is.

So as I started to realize that was working, I just doubled down on it really aggressively. So I started saying “Follow me and subscribe here.” And then what I would do is, as more people followed, I would tweet out the link once a week and I got a little better at it over time. I figured out different ways to structure the tweets and the perfect lengths and where to include pictures or videos and what kind of stories people really liked. I'm about 10 months in now, and I have just short of 40,000 subscribers. So it's gone really well, from a subscriber standpoint. And then on Twitter, I'm up to almost 200,000 followers. So that's been the primary growth channel. I would still assume that kind of the majority — if not like 90% — of subscribers are coming from those Twitter threads and Twitter in general.

It's really interesting to hear you talk about things like creators and personality and marketing on Twitter. It sounds like you have a lot of media savvy. I've interviewed media founders who are just starting to talk about these things as sort of the next wave. And you've already zeroed in on it as a core part of your strategy. So I'm wondering, where did you develop that awareness of what you needed to be doing in order to grow and scale and build your brand? 

I always like to mention, right off the bat, so people don't get angry, that my brother has a large online audience. So I think that was obviously helpful starting out. When I started on Twitter, he probably had some 350,000 followers. He focuses on finance and cryptocurrency, and as those topics have moved in the mainstream during COVID, his audience has grown aggressively. So it's helped us both get somewhere great. I say that because I don't think I had some master plan, right? I just strongly believe that individuals were the future of media and legacy media organizations were in trouble, not only from a trust standpoint, but just from a business model standpoint. I think that people inherently trust individuals a lot more than organizations. For the individuals that are working for organizations, sometimes it can be super helpful for them to have that kind of masthead that says, “Hey, this is where I work.” And it gives them some degree of legitimacy. But for me, it was just like, “When it's under my name, I'm in control of everything, right?” 

Pat McAfee is a great example. I've really admired his business, to be honest. I think he sometimes gets referred to as an influencer, which is funny to me, because he's just a world class entrepreneur. He's come out of the NFL and built a massive media empire with his show and his merchandise and all the other different things he does. So at some point, you see these individuals turn into big media companies. I think that it all comes down to two main things: you need really good content, then you need distribution. And I knew I inherently had the one advantage of distribution — my brother can help me retweet things, he can comment, he can like, he can amplify the message. And if I can get these things in front of other people, and it's good content, then they'll share… and subscribe. So my main goal throughout the whole thing was to focus really, really intently on the content. And it's obviously tough with a daily newsletter. I think some people get overwhelmed, and I certainly do a lot of the time. But the consistency that I have to be able to compound over time, I think is really important with the daily newsletter. So keeping that content quality up was really important. And then I saw that once the content was getting really good, it was getting shared a lot. I say all the time that I certainly had an advantage — I'm not naive to that at all. But I've put tweets out there that just weren't good before. Someone with 5 million followers can retweet it, and if it's not good, no one's gonna like it. No one cares, right? If it's just not a good tweet or it's not a good article, they just won't share it. So the quality was always the first thing I focused on.

So if you don't mind me asking, I would love to know some of your metrics on the newsletter. How many subscribers do you have? You've talked a little bit about the growth of your Twitter metrics.

Yeah, of course. So I started in July. Now I have just under 40,000 subscribers. So from the top-line, revenue and growth have been good. Open rates are around 35% to 40% depending on the day. Some days trend better than others. But that's one of the things I've really been proud of. And to be honest, I don't think I've focused on that, necessarily. And it's not something that I check every day. But it's certainly something that I'm cognizant of now, which is just the ability to keep those open rates really high and keep readers engaged as I’m scaling the newsletter. So I think that those open rates would really be seen as normal and kind of just par for the course if it was a once per week newsletter or something like that. But it's daily, right? Every single day, you have to get people in the cadence of opening this newsletter, which I think is tough. So I'm really proud of the fact that that has been able to keep up.

I'm sure you want to get into the monetization aspect at some point. I was able to leave my job at JPMorgan in September, so just a few months after I started the newsletter. And really, my approach to that was that we were two to three months in at that point. I realized that this is something I want to do. So one, there was intention, passion and purpose behind going in and wanting to build it out. And then my next thing was like, “Okay, how can I get enough revenue to be able to quit my job and do this full time?” I knew if I was able to focus on it full time, I would be able to scale it rather quickly. People laugh when I say that I work more hours now than I did at JP Morgan, which is funny to some degree, because I think people on the outside view JP Morgan as a super demanding job. And it certainly is... but just being your own entrepreneur and running your own single-person media business is a beast of its own. There's just so many different things that go into it, as I'm sure your guests have told you previously, but it's just a lot of work. So my goal was just to be able to stop doing both jobs [at the same time] as quickly as possible, because it was probably impacting both to some degree.

"It's gone really well. We're well into the six figures, hopefully in the seven figure range soon."

I wanted to figure out the best way to be able to double down and go for the newsletter. And what that turned out to be was through ads. So I was able to put together a package and I reached out to some advertisers and said, “Hey, look, I'm looking for one exclusive advertiser to be able to provide me enough revenue so I can leave my job and do this full time. And I don't want you to do it on a monthly basis: I want you to commit for six months, so I know that I at least have a cushion for six months to really go and build this.” I was open and honest with them. I shared all the metrics, I told them where I'm where I'm planning to be, I told them what I'm expecting from a growth perspective and all that type of stuff. I was able to secure a sponsorship with Athletic Brewing. I still work with those guys, and I try to credit them and intentionally plug them to some degree whenever I can. Because, look, it just wouldn't have been possible without them. So I'm really appreciative of that. They've been great partners and we still do a lot of stuff together.

I'm listening to you talk and I'm hearing so much of what I hear from people in the industry who are trying to build platforms for creators, and also from creators themselves. You talked about how you work more hours when you're by yourself, about the the desire to quit your job and pursue your passion — that’s such a fundamental through line of the work that creators are doing. When I hear the way that you worked with advertisers, it sounds like you were so confident in your product and in yourself as a creator and your ability to make it work. I think that's really interesting and admirable that you were able to present your newsletter to an advertiser and make a deal like that. That's very forward-thinking.

Yeah. And that's an interesting point you bring up because I don't want to give people the wrong idea. I like to always [clarify] that I'm certainly more confident about it now than I probably was then, because this is all new. I just hadn't done it before. But yes, the one thing I was always confident in was my ability to produce from a content side and continue to grow the audience side. So I've learned a bunch over the last eight-to-ten months. But I think the one key thing was always that I was confident that if I had the time to be able to go and do it, that it would continue to scale. And that's exactly what we did. So I'm certainly more confident now. But I think it was always just kind of that inner belief that it would work out.

I don't want to force you to put numbers out there if you're not comfortable with it. But I'm curious now, almost a year into the newsletter, where you are and how you're able to support yourself through it financially. Because it is, as you mentioned, a free newsletter.

Yes, yes. I’ve moved on from the single advertiser model, and I've been able to bring on other advertisers. And what I've seen is that the creator model affords you one huge advantage, in my opinion, which is the ability to package advertisers with multiple assets. And what I mean by that is the ability to put them in the newsletter, the ability to tweet about them, the ability to add them to threads, the ability to pitch them in podcasts. It's almost kind of like what I would liken to an endorsement deal for an athlete. But the reality is, when you only have three, four or five partners, you're able to charge really high CPMs because you do all these different things [with them]. I've done videos with the CEOs of companies. I've allowed them to write guest posts. Stuff like that. There's just a bunch of different options, and I think that’s an inherent advantage of doing it on your own. 

So let's run through the model real quick. The way I think about it normally is that I usually have four to five sponsors at a given period. I like to structure them as long term deals, and I mean that as in three-to-six months, and they pay a set fee. And they get a combination of newsletter ads, maybe a couple tweets, and then like one unique thing [like] a podcast episode or something like that, depending on what they want. So there's something unique that they would get as an asset. But I think that advantage has been really helpful. I was laughing about it earlier with someone [I partner with] —I got an email, and it was from someone who works with a bunch of other newsletters within the sports business ecosystem. And they were just like, “Dude, your engagement metrics are awesome.” He's like, “We partnered with a bunch of other guys and yours have really come back. Not only are people coming to our site, but they're spending money. They're super engaged."

I think one of the biggest things that could be helpful for a lot of ad-based creators is the ability to negotiate sponsorship deals, the ability to execute contracts, the ability to send invoices, take care of payments, do ad copy, get imagery... You start thinking down a line of all the things that are necessary, that goes into it outside of what a normal creator has to do, right? It starts to add up for an individual. So I think there's probably an advantage to taking care of that aspect of it from [the perspective of] building a company. But to answer your question in a long-winded way, yes, it's gone really well. We're well into the six figures, hopefully in the seven figure range soon.

Well, congratulations, that's an incredible achievement. I'm sure it must feel like a huge relief to have gotten to that point in such a quick amount of time, even with all these caveats you mention like your brother. 

And I always like to admit that because it's true, right? I think it's always helpful to put that out on the table. But also because I don't put up with a lot of the nonsense [on Twitter] of people being like, “Hey, it's all because of your brother,” or stuff like that. 

I want to ask about the content of the newsletter itself. Personally, I'm not a big sports person. It’s something that's never really hooked me. But lately, that's been changing because I've gotten into Formula One via Netflix. And I find the way that you write your letter to be really relatable and interesting, even for someone like me, who's not part of the sports audience. I read a number of your newsletters and really liked your story about [the Monaco Grand Prix].

For me, from the outside of this branch of media, most of the content I see about the business behind sports is player contracts and things like that. But I think your choice to focus beyond that, and talk about things like the cost of being a fan, or the cost of sponsorships and how the economics of hosting an event like the Monaco Grand Prix works — I think that's a really interesting choice. And I'd love to hear you talk about why you decided to take that path and not just report on the biggest, most eye-catching parts of the industry that are widely clicked on.

It's funny. The way I actually think about it is, “Would this be interesting to the average fan?” I think that most people get scared when they hear people say that, because we've been trained to just think that people working in these shoes do the best. And if you can get to 3,000 or 4,000 loyal followers, you can build an incredible business. And that's certainly true for certain things. But for me, there was a great opportunity to bring the things that people would inherently ask themselves as regular sports fans and connect them with the business side. 

You talked about the way I write, and I think one of the things I do is I intentionally write in a very simple manner. And part of that is because I don't think I'm very smart. But the other part of that is I like to keep it as something that the average fan who isn't into the business side as much can understand. Monaco is a good example. Everyone sees the yachts out there — how much are those boats paying to dock there? How much does it cost to attend? How many people live in Monaco? What does the winner of the race make? Here's a bunch of different things that, I think if you sat down as a fan of Formula One, are questions you probably might have asked yourself during the race, and they're very  forefront things. It would be very different to dig into the balance sheet of Liberty Media, who owns Formula One, and say, “Hey, this is how much debt they have. These are the bonds they issued,” and all that type of stuff. So I think it's a fine line of engaging a broader audience. But you also want to provide enough value and dig into the details enough to where you're not just repeating things that other people have said. So I intentionally target topics or opportunities that haven't been covered for a lot of people. So if I Google something and there's 1,015 articles out there already discussing it, I won't write about it because you assume that if ESPN or The Athletic or Fox or CBS or any of these big outlets have done it. That people that are interested in this already know about it and they already read about it. 

So I intentionally try to pick topics that don't dig as deep. Monaco is a good example — one, because you're interested in it — but two, there just wasn't a bunch of content out there. And the content that I found was actually false. It was just written so long ago that numbers have changed. So part of it is certainly intentionally looking for things that are not out there. And then another part of it is making it super relatable to the average sports fan.

The next thing I want to move into is to ask you about a couple of different trends or movements that I've seen reported on in the industry that are currently happening, and that you've written about in your newsletter several times. I want to kind of gather your thoughts on it, your read on it, and where you think it may be going. So kind of a quick fire, three or so different things. 

First: You've written a lot about sports betting. I find that to be really interesting — partnerships with the NFL that companies like DraftKings make. I was wondering if you could talk a little bit about what you're seeing there and the future of that part of the industry?

I think there's a few interesting things. PASPA was repealed three years ago in the US, which allowed individual states to legalize sports betting. What we've seen is kind of an acceleration of that. New Jersey is kind of the leader now — they call it the “Las Vegas out east.” It's kind of become the biggest player in sports betting. And what we've seen throughout COVID is that now a lot more states are considering it because they just lost tax revenue. So New York's considering it, Florida is passing laws, and stuff like that. I think around 35% of the US has access to mobile sports betting currently within their state where they live. And Macquarie believes that that'll move up to over 90% by 2025. So really not far at all. They're thinking that we're gonna see a massive acceleration. If you ask someone in the sports betting industry what the total market size could be, you'll get like, five different answers because everyone just has a different belief. But what I think we're seeing is there's obviously an appetite for it, right? So we're seeing the companies that are trying to acquire customers spend a lot of money to do so, because they're incentivized really early on to grab as much land as they can and as many customers as they can. Because when you go to a new state, they're only allowing four different players to come in and be operators within that state, which means they're gonna pick the four largest and the four best ones. DraftKings is a good example; they're going to spend a billion dollars this year on marketing. And they're going to make like $1.2 billion. So just an absurd amount of money on just marketing. And that's what I mean by kind of just going out and grabbing as much as you can. But what I think we're going to see is product innovation really expand the market.

And the perfect example of that is in-game betting. In football, there's a 40-second play clock during which you can bet whether the next play is going to be a pass or a run. There are firms that are doing these simple bets, but I think what we're going to see is that as products like that start to come up, the market is going to expand, and we're going to see the business explode here in the U.S. And over time, that's going to have a compounding effect on the total market size.

Something that I have seen in the past couple years — and it's definitely slowed down in recent memory — is traditional sports stars like Gordon Hayward getting involved in esports. So I'm wondering if you could talk a little bit about what you've observed there?

I don't follow esports religiously, right? It's not something that I cover all the time. But I certainly read enough about it and kind of get involved in enough to have an opinion on it, I'd say. But my general thesis around esports is the market just grew really, really, really quick. And things became overvalued. You talked about how you heard about a bunch of people doing things a few years ago, but you haven't heard about it as much lately. That's exactly what I mean, right? It was just really, really hot. And to be fair, some companies and industries are growing, and it's certainly a massive opportunity still. But my general thesis around it is that I think that all the teams will eventually have some kind of component of it. Formula One's a good example — they have an esports league that they own and operate through Liberty Media that's kind of combined. There's content within their streaming app that works with esports. So they use it as an ancillary offering to Formula One. I think that that makes a lot of sense from a league perspective.

And then I think from an asset perspective within the space, the best investments, I think, are going to be brands that go outside of gaming. And I think that that kind of scares some people within the gaming community, because they're like, “Hey, if they're not winning tournaments, and winning all these things, why do we care?” It's like, no, they're gonna build major lifestyle companies. 100 Thieves is a good example. 100 Thieves sells sweatshirts, they sell merchandise, they have the CashApp Compound, they sell a bunch of sponsorships, they have houses that [their talent] lives in, they create YouTube videos every day, they have podcasts, etc. Maybe they've gotten some flack for not winning and doing all that type of stuff, but I think the most valuable companies are going to be those that expand, right? So if you think of the Barstool Sports of the world — who can do that in gaming? Who can create all those ancillary revenue streams and be able to compound their fame and their following over time?

The next thing I want to ask about is the debate around paying college athletes. I’m curious about your personal take on it since you said that you had really strong feelings about it. And also, if you think that it’s something that's going to happen in the future, and what the financial implications of that will be for brands, universities — things like that.

I would start off by saying, Yes, I think that all college athletes should have the ability to earn money off their name, image and likeness. There's a million different ways to do it. But when you mention it, I think some people think, “Why should Duke University pay an athlete thousands of dollars every quarter month or whatever when they get a scholarship?” And that's not even necessarily what I'm saying, but it's just — I don't want to get into the bold claims, but it doesn't seem right that they can capitalize off your name, image and likeness, and then you're not able to go make money on it yourself. Let's just take the easy route, which is just name image and likeness and endorsement deals — why can't a college athlete go and capitalize on his name, image and likeness that he has put up over time? Zion Williams is a good example. He was a bonafide superstar coming out of high school. And there's a million different reasons why that was possible. One of them is Overtime, a sports media company built for a younger generation of high school athletes. They really capitalized on that social capital and social equity online. I don't know the numbers, but I have to imagine he had over a million Instagram followers by the time he even left high school. And that's someone who, whether he went to Duke or not — and Duke helped his national profile for sure. Don't get me wrong — could have been making six figures immediately [if he went to the NBA or elsewhere] on sponsorships and brand deals and appearances and all that type of stuff, right. And I just think that his inability to do that in college speaks volumes to the system. 

But back to the original point, I think now we're seeing a bunch of different options pop up. And part of that is offering them different options of where to go. So outside of college, there's the G League, which pays players up to $500,000 a year, and you go live out there for your college year. And they'll train you, you'll play in games, you'll get paid, you'll do educational financial classes and stuff like that. And then there's Overtime Elite, which is similar in nature, but it's supposed to be for if you're a year younger, maybe, and you go live in Atlanta, and they do the same stuff, and they pay you six figures plus, you're able to capitalize on your name, image and likeness, you're able to do shoe deals, you're able to you get equity in the company. So there's just a bunch of different things that they try to compete against. I think over time, yeah, we're just gonna see all these individual states pass laws that allow these players to capitalize and make money on their name, image, and likeness. It's kind of like an ongoing joke within sports. It's like just, wake me up when it's actually happening. Because it almost feels like every day, there's a new state law being passed, or a new update or whatever. People write about it constantly, and I try to stay out of a lot of that kind of day-to-day movement. But I think we're headed in the right direction. There's going to be states that are legalizing within the next 12 months, and the NCAA is gonna have to respond. 

I don't want to keep you too much longer, so as a final question, I would love to hear what you have planned for the future of Huddle Up. What you would like for it to one day become, or what even what you think the next immediate steps are for you.

I think when we talk about long term, the important thing to recognize is that the audience eventually is all used for distribution from an investing standpoint. Along with the creator-centric part of the media company, I think the greatest investors will have their own built-out audiences, right. And what that enables you to do is not only see better deal flow because of that audience and that influence and whatever it might be. But it allows you to create inflection points in businesses that you invest in your own capital. So I think there's a point in time where yes, I'm going to be starting a podcast. And yes, I'm going to be putting links on YouTube and videos and doing short stories and stuff like that. And that's all part of the media side. But really, what it's used for, is to continue to build that audience and that distribution for investing stuff.