Ellen Hyslop Talks About the Various Stages of Building The Gist

My guest this week is Ellen Hyslop, co-founder of The Gist, a fan-first sports media brand based out of Canada (but serving the United States). In this episode, we talked about the early days of the business, what sorts of growth tactics they used when first starting versus what now works, how their user onboarding impacts the types of content that readers see, the various ad products they take to market, and where the business goes from here.

Jacob Cohen Donnelly: Newsletters are all the rage right now, and honestly, they have been for quite some time. One area that I always swore to avoid in the newsletter space was sports for a number of reasons. We can go into those at any point, but you obviously have not avoided sports. What is The GIST? Give us a synopsis on the origin story.

Ellen Hyslop: I really do want to circle back on why you said that you would never go into sports, but that is so interesting. Really, The GIST is a fan-first sports media brand that is all about shaking up the male-dominated sports industry and leveling the playing field in sports. The way that we think about our business, I think, Jacob, which might be a little bit different and maybe leads to the hesitancy of you entering sports, is that we really are fan-first. We are audience-first. We think about the underserved sports fans. Women’s sports fans, folks from the LGBTQIA plus community, BIPOC community, et cetera.

Essentially everyone who’s not an avid sports fan and folks who feel like they are not served by ESPN, Fox Sports, what have you. Really the impetus to us starting The GIST came up really super organically. My co-founders and I all studied business in our undergrad. We all moved downtown, started working in financial services for a few years, which was obviously very male-dominated spaces and places. We quickly learned that sports really are a social currency in our society. People enjoy talking about them. They’re able to unite people regardless of race, gender, religion, what have you.

So often women and other underserved sports fans were on the outside of that community looking in. For myself, I’ve always been a super massive avid sports fan. I thought that I would be on SportsCenter one day or on court, that type of thing. Even for me as an avid fan, I found myself having to insert into conversations, having to ask to be a part of the survivor pools at the office, all of that sort of stuff. For my co-founders, they played a lot of competitive sports growing up, but it didn’t actually translate to fandom in the same way it did for me because sports really felt like this gate-kept community that was a boys’ club.

We just really felt like sports shouldn’t be that way, and so we launched The GIST. Since then, we are really, really close to hitting 1 million subscribers across all of our newsletters, with the majority of our audience being women. It’s the exact kind of flip-flop of what you would see on ESPN where the majority of their audience, I think it’s 75% male at this point. Ours is 80% female.

Jacob: While you’re based in Canada, is the majority of the content and the majority of the audience based in the States or is it blended?

Ellen: Exactly. We were founded in Canada, but the majority of our business is actually done in the US. Our team operates completely remote. The majority, or I’d say about half of our team is based in the US, especially on the content side and the revenue side of things. The majority of our audience is American, the majority of our content is American, and within our newsletter. We have three different newsletter verticals. We have Sports News, which is our flagship newsletter where we provide the gist of what’s up in sports in less than five minutes on the men’s and women’s side.

On the pro side of things, we have our Women’s Sports Business Vertical, which is really speaking to folks in the industry or adjacent to the industry that want to learn how to invest in women’s sports or are curious about the opportunities there. That comes out three times a week. Then we have an NCAA newsletter that also comes out three times a week that covers men’s and women’s college sports equally on that side.

Within our Sports News email, which is our flagship email, it’s also localized. We have Canadian content, American content, and then we have nine city-specific sections because we know that sports are such a localized community and that you’re a fan of your specific sports. When Gisters onboard based off of their favorite teams or based off of their location, they can also receive an additional section within our newsletter that would cover Boston sports in particular or LA sports in particular, for example.

Jacob: Let’s actually talk about that onboarding for a second, because you’re right, sports is so local. When a user signs up, walk us through the information that you’re gathering about them. What data do you have about them and all that?

Ellen: It depends on where they’re coming from. We are able to leverage data and leverage some tracking to source what type of growth channel they’re coming from, which I’m sure, Jacob, you’ll want to get into later anyway. We source and track what type of growth channel they’re coming in from. Of course, on that email side of things, you immediately get their email address, which is just so amazing to have that one-to-one email relationship as you know with your email too. It’s a really intentional subscribe and they’re really allowing you to come into a place where they’re living every single day and they’re saying they want to hear from you.

Immediately, that triggers our welcome email and onboarding flow. Within our first two to three newsletters on that automated welcome onboarding flow, we have a welcome survey where we ask more about our audience. Five quick questions. A little bit on the demo side, but also a little bit on the behavioral side where we’d like to understand their level of fandom in sports, and also understand what their favorite sports team is, all of that sort of stuff. We have a little bit more information on the local side of things too. Then as they stay with The GIST and as they continue to be a subscriber at around the six-month mark, we also have a net promoter score survey where we understand the likelihood of them recommending The GIST to their friends.

Jacob: You said that you’re pushing 1 million subscribers, which is an exciting threshold to hit. What have been the tactics that have worked well for growing the brand?

Ellen: There’s been a few different things. I think early days is really different to where we are now. Early days we had no money. We had to be so scrappy, but some of the things that we did really early on worked out super well and helped to lay the foundation for us on how we grew. We soft launched in Toronto. The reason why we soft launched in Toronto was, of course, we were all living there. We were from there. We knew the market. Also, we wanted to test and play in Canada before actually going to the US where it felt like the stakes were so much higher.

When we launched The GIST, we hosted a massive party at the Shopify offices. We worked with a lot of brands in the local Toronto community like MLSE, which is Maple Leaf Sports & Entertainment, and their specific teams like the Toronto Raptors, Toronto FC of the MLS. We worked with the local Lululemon stores. We worked with local SoulCycle stores, all that sort of stuff. With the sale to them saying, hey, we are reaching this mid 20-year-old on-the-go woman who likes to stay informed, she’s educated, who has high levels of disposable income.

We’re launching. You have this opportunity to support a women-founded brand that’s trying to switch things up in the sports industry. Are you able to be part of our giveaways or grab bags and things like that to help get people to come to our launch party? We ended up selling at our launch party, having over 200 people. Free drinks, free food, free booze, all of that stuff. We did a presentation there. What was basically their ticket to coming was you’d automatically be subscribed to the newsletter. Our ask for everyone there was when your first email comes into your inbox, please forward to three people.

Literally after our first newsletter, we were already up to 800 subscribers. It was so cool to see at the beginning what an event like that would do in terms of community. Then we also started working– Again, us being fan-first, it’s all about our audience and it’s all about really understanding our subscriber and finding brands who want to reach her. We would work with SoulCycle early days and say, if you refer three friends to The GIST, you get two free weeks at SoulCycle. Everyone went crazy for it. SoulCycle loved it. Our audience loved it.

Then again, we were able to onboard hundreds of subscribers. That’s how we did things when we were scrappy and really didn’t have any money, and were still doing it off the sides of our desk as a side hustle. As we continued to learn and get more sophisticated, we’ve broken down our growth into I’d say four or five different buckets. Definitely the organic side of things, the PR side of things, word of mouth, all of that stuff is a major bucket.

The second side is definitely paid social, advertising, looking at Meta, TikTok, Twitter or X if you want to, LinkedIn and testing all of those over the years. The third is more so on the scale side of things, a little bit more low-quality subscriber but a lot of volume on contesting, co-registration, all of that stuff. Then the last one being cross promotions and referrals. I’d break it down into those four groups.

Jacob: Obviously we’ve both come from newsletters, and I remember a couple years ago Apple rolling out their mail privacy protection policies, which basically made the open rate much, much harder to trust. What sort of tactics have you developed to handle churn, especially when we talk about those sources like co-registration and contests, how are you handling churn?

Ellen: Question of the day. On those Apple iOS privacy things too, we’ve been chatting with a lot of folks in the space about how they adjust their unique open rate down, what’s the percentage points. We look at our list all the time to see how many Gmail subscribers versus Apple subscribers, versus Outlook and all that stuff, and really look at the source of truth on the Gmail side too. Obviously there’s been some stuff with Gmail and Yahoo even recently too. When we think about churn for our strategy, we definitely want to have a high-quality list.

It doesn’t matter if you have 1 million subscribers if no one is opening or if only 10% are opening. We have automated churn going on in the background wherein if someone hasn’t opened a newsletter or it looks like they haven’t opened a newsletter, after nine newsletters, they get an automated message from us that’s basically like, do you so want to be subscribed? Have you been opening, and we’re wrong. If we don’t hear from you type thing, we’re automatically going to unsubscribe you. We essentially put them into a holding list from there so that we don’t lose their email.

They’re put into a holding list and they don’t receive our newsletter any longer so that they don’t impact our open rates. From there, what’s really great about the sports calendar and ecosystem is that we know that there are events that people are obsessed with like the Olympics, and so we’re able to get in touch with them because they haven’t technically unsubscribed ahead of those marquis events. The Olympics, NFL Season Star, women’s World Cup, those types of things will reengage with some of the subscribers on those holding lists as well.

Jacob: You use nine emails as the threshold. Before you mentioned there are three newsletters each sending three times. Is it after a week of all three newsletters or how does that work?

Ellen: Most of our subscribers are subscribed to one of the verticals. Sometimes it’s two, sometimes it’s three. Those that are subscribed to multiple are really, really highly engaged subscribers, so they’re good. They’re never going to get going to get that email from us. It really is when they’re subscribed to one specific vertical and they still have an open after that nine times. It essentially gives them two and a half to three weeks of seeing and testing out. Obviously we’re also looking at click data too because if the Apple isn’t properly showing their opens, or for whatever reason one of the other platforms isn’t properly showing their opens, we also look to see if they have been engaging and clicking through anything.

Jacob: With the paid sources that you’re using, how are you determining the appropriate CAC, Customer Acquisition Cost, to actually acquire that sale?

Ellen: First, we think about our high-level metrics in terms of lifetime value, in terms of revenue per subscriber, revenue per open, what we’re expecting on the top line side of things for the year, our average deal size, all of that stuff and then how that nets out to our growth strategy and plan altogether. From there we look at CAC really, really differently depending on the channel. When we look at social in particular, it does vary a little bit whether you’re looking at Meta, TikTok, LinkedIn, or Twitter. If we want to double-click on Meta, we are willing to spend a little bit more on our Sports Biz newsletter because that is a–

All of our audiences are really sought after actually. When you look at Sports Biz, they’re decision makers who are spending a lot of corporate dollars as opposed to necessarily personal dollars to a certain extent. We’ll spend a little bit more there. It really all just comes back to that LTV2 CAC ratio which we’re generally looking to be five to one within a year type thing. We’ve been seeing a lot of improvements for us on the paid social side of things, which is really, really awesome and we’re tracking it consistently. Because sometimes if your CAC goes too low, you’re like, are we reaching the right people?

Are they retaining? Are they opening? Is this just like an ad that’s working, but it’s not actually a healthy thing for your business, or is it potentially a dollar or so high CAC? When you look at the retention and when you look at the open rates, it’s worth it from a revenue per subscriber revenue per open. We have an amazing operations and data team. Laurel, shout out, Laurel, who really works really, really closely with our growth team and looks after all the data month over month to make adjustments as needed.

Jacob: Then you obviously have a referral program like every great newsletter business does. What have you found works really well with the audience that gets them engaged with referring versus what things just don’t really work?

Ellen: It’s interesting. I’d love to ask you some of these questions given your background and where you’re coming from. The referral program in and of itself, when you think about a newsletter, and I think about myself as a user, or when I think about my friends and I see them and how they interact in their newsletter, again, thinking really fan first and how people actually behave, it’s only going to be those super users and people who are highly incentivized by merch or your prizes that are actually going to refer. I just forward.

I honestly could not care to refer necessarily a friend to get something free or to get stickers or whatever. It’s really going to be your super users who are doing it or people just forwarding what we found to get people like me actually engaged, or the average person actually engaged, is that there needs to be incentives on top of just those referral prizes too. Whether that means you’re giving away Apple AirPods, whether that means you’re giving away tickets to the WNBA finals.

It really just depends what Gister your profile, we call them, or user profile you want to be reaching with that specific contest. We are right now in the midst of overhauling our referral program. We have been funding, hosting our own contest off-platform to be also a really fruitful driver for high-quality growth, but we want to have a better system for our referral program. Look out for an update from us probably Q3, Q4 on that front.

Jacob: Obviously you’re going to make changes, but right now the first prize is after three referrals, you get added to The Gistfluencer community. That is a [unintelligible 00:16:56] what is that community? What’s involved in that?

Ellen: It’s a play on influencer, if you will. Basically when you’re part of The GIST influencer community or you’ve been with The GIST for over a year, you get invited to this really exclusive Facebook group of like-minded individuals where they’re chatting all the time, talking about things that they’re seeing in the newsletter, chatting about things that they’re seeing in sports, talking about the games that they went to, all of that sort of stuff.

They have direct access to our team, and in particular, our social media producer who moderates everything on that Gistfluencer side of things. They also receive a personalized email from me every single month, giving them the peek behind the curtain of what’s happening at The GIST, and what they can expect for the month ahead.

Jacob: Let’s move and talk a little bit about the business or the revenue side. As far as I can tell, you are almost exclusively an advertising business.

Ellen: Yes.

Jacob: Walk us through the different products that you currently offer to advertisers.

Ellen: We really work with brands to be that authentic gateway to connect with a female fan. I think when you think about the sports space again, they are reaching majority male fans, and there isn’t a space for brands to actually reach these female fans, these up-and-coming fans, fans who are , on their new journey. We act as a way for them to do that in an authentic way because we have the voice and we’ve built the trust with our audience within our newsletter, it really is all native and bespoke advertising.

Probably similar to the way, Jacob, things were run at Morning Brew when you were there, and similar to yourself now with your newsletter, all of our content is created in-house. We receive all of the information about the key messages from our brand partners, but we make sure that all of the placements and features within our newsletter are in our voice. Think about the value proposition for our audience in particular, so that our content can also really be a value add to the brand because they’re learning how to get in front of our audience in a meaningful way.

We basically have four or five different placement options within any given newsletter. We have a presenting feature at the top of the newsletter. We have a primary feature that includes a longer section in addition to a photo and some link outs there. That section really allows for some great storytelling. We have a secondary feature that we have at the bottom-ish of the newsletter. Then also we have a section within our newsletter called The GIST Picks that really is recommendations from our entire team, and brands also have the opportunity to be put in there.

What’s really cool as well that we notice with the sports space in particular is that brands like to just be associated and come in around certain events. We have brands be specific sponsors for March Madness, or specific partners for MLB. We also have them as a presenting partner or section partner for those sections where we’re covering Major League Baseball. In that day you also might see a Corona logo and everything is presented by Corona.

Within the newsletter, that’s how we’re working. We’re talking about newsletters right now, but with The GIST, we also have a twice-weekly podcast. We also have social media that’s on Instagram and TikTok, and Twitter. Our Instagram and Twitter is also separated between Canada and the US. When we are working with our partners, we’re also thinking about packages and bundling across all of our different kind of platforms.

Jacob: If we look at the main newsletter, I suspect that goes to the vast majority of the audience.

Ellen: Yes.

Jacob: If you have a sellout day, what is the revenue for percent?

Ellen: It depends on the partner, it depends on the day depends if they’re on the Canadian list or if they’re on the US list. I’ll have to get back to you on that but it’s very healthy. We find that when brands do buy more than just one placement within a newsletter, or engage with us on a special edition email that we have, which is essentially previews or primers for an upcoming season or playoffs, or championships or whatever, when they’re a part of the entire newsletter and it’s really clearly brought to you by that brand, they perform really well and definitely drive brand affinity and awareness with respect to those newsletters.

Jacob: Is the majority of what they’re tracking, is it performance? They just want clicks or are they using this as a brand building tool for themselves?

Ellen: It really depends on the brand and their goals. We definitely work with some performance partners. As you know, newsletters, they can be really great lead generation drivers depending on the vertical, depending on the product, depending if it works for your audience. They tend to sometimes be a little bit more top of the funnel or they go to your website and then it’s still up to that company to be able to convert them if they’re going to be very performance-oriented. We break down our different ways of how we work with partners into three avenues.

One is a little bit more on the bespoke content, coming up with a new and creative idea. Really a brand is coming to us or we’re coming to a brand and we’re like, hey, this is something really cool that we could be doing together. What are your thoughts? We work with them from a really partnership consulting perspective. Another side of our brand partnership is really that amplification. Again, they already sponsor an athlete. They already are associated with the league. They are already associated with the team. That’s great. Just to be associated with a team or a league, or an athlete, you have to let people know that you’re doing that and that you’re doing all of this great work.

We’ll be amplification partners for events and things like that. We’d work with Nike around everything that they were doing with the NWSL and winning a Golden Globe last year. That was an amazing brand engagement partnership that was on the amplification side of things because they were doing just something so cool. The USTA, for example, with the US Open, that’s one that’s amplification about the US Open, but also performance-driven where we’re saying to our investors, this is an amazing tournament.

It’s so much fun. Really, you should go buy tickets. Work with F1 Miami, very similar on that performance, but also brand affinity side of things of they want more women to be enjoying F1. They want more women to be going to the tennis tournaments. Those are the three buckets of really bespoke content amplification and then supporting on lead generation.

Jacob: You asked me why I avoided sports. Here’s one of the reasons, and it’s one of my questions. Sports media brands, they are massive. ESPN is massive, Bleacher Report, I don’t know if that’s still a thing, massive. These are all very massive brands. Their advertisers are inherently used to mass scale campaigns. You are not mass scale, right? You’re still sub 1 million. Then on top of that, you’re not your newsletter, you’re native. You’re not just like throw banner ads up and forget. Have you run into any issues convincing these consumer brands that are used to mass scale advertising to work in the newsletter?

Ellen: It’s a really good question. I think really astute for the sports space too. We had that same idea, I think, Jacob, from the beginning. We knew that we had to approach revenue in a really different way than what was existing in the sports space. Again, our audience is different and it’s really hard to reach. As much as they can get scale and work with those big broadcasters, they’re getting scale with avid fans and they’re getting scale with avid male sports fans. If they want to be working with a different type of audience who’s really not engaging in the same way or as much on those platforms, they have to work with The GIST.

It really does come down to who they want to be working with. We straddle the men’s sports ecosystem and the women’s sports ecosystem. When you think about the women’s sports ecosystem, it’s a really different industry altogether in the way that businesses work, in the way that businesses support, in the way that they amplify. It’s a little bit more of how can we support the ecosystem. You’ve probably seen, but over the last few years, women’s sports have grown so much. I’ll be honest, it’s not off the backs of these traditional sports media brands that have all this scale.

It’s off of companies like The Gist and Just Women’s Sports, and together in these startups saying, because of the democratization of digital media, we’re able to talk about these things. Nobody else is doing this. Then we’re able to, because we actually talk about women’s sports and have authority in the space, work with these brands as well who want to reach us.

Within that space, we have a very large audience and we have a very large newsletter audience that no one else in that space can really touch. Again, the audience is just so different. They are so smart. Again, they’re on the go, female zillennials who generally like to stay up to date. If you want to be associated with sports in that way, again, it’s really hard to reach them through that scale play.

Jacob: You started as a newsletter and then made the move that a lot of other newsletters do, which is expand into audio and social. What was your logic behind making those expansion plays?

Ellen: We did launch with social at the exact same time as our newsletter with The GIST. In the early days, Jacob, I was like, oh my God, it’s just me writing and posting on socials and doing all this stuff and learning as much as we can. Our first full-time hire was actually a social media manager as opposed to a writer. We had part-time writers for a while before we hired full-time. Social has always been really important to us. Again, thinking about our audience, they live on social in the same way that they live in their inbox. We knew that it was really important for us to be there too.

Our social strategy is different than our newsletter strategy in some ways, and then similar in other ways too of how we like to cover content. What’s the context? How are we covering men’s and women’s sports? What are we doing that’s different? How is it aesthetic and different than these boys clubs sports pages, which we don’t need to get into that, but not our cup of tea. Social has always been at the forefront. With respect to podcasts, in the early days, we were constantly, and now we’re always constantly asking our registers for feedback, constantly talking to our registers, seeing how they’re behaving and they’d ask for a podcast.

We started doing it weekly. We were seeing the downloads increase. We were seeing the interest increase, our listenership improve all the time. Then we said, now we got to bring this up to twice a week. We’re at four years almost with our podcast. We launched in February, 2020, which was the best timing ever. We now have over 1 million downloads, and we have a presenting partner on the podcast this year in Aflac, which is really exciting.

Jacob: That’s awesome. In my career, I have launched three job boards, and in my career I have failed at three job boards. I have sworn to never launch a job board again. You have a job board. We do. Has this meaningfully contributed to the business from a revenue perspective or are there other reasons to offer this?

Ellen: Not a meaningful contribution on the revenue side of things. For us, it was coming back to two things. When we think about the mission of The GIST, it is to level the playing field in sports. We provide, again, equal coverage on men’s and women’s sports. Women’s sports has anywhere between 5% to 7% on traditional media and 15% on digital media and coverage in comparison to men. That’s the one side that really our sports newsletter and our college newsletter tackle. The other side, though, is that it’s between 14% to 18% of sports journalists are women or non-binary folks, and all of our content is created by women and non-binary folks.

When we thought about our mission and when we thought about when we were entering that business space of covering the business side of women’s sports, we said, this feels like a natural extension of that. We found a great job board platform partner. What’s been really cool is that it’s been a awesome brand driver and growth driver. When you look at, especially right now in the market that we’re in, when people are hunting for jobs and searching for jobs, the job board really supports us on our organic growth and our SEO.

It really helps us on that brand building side, especially on sports biz and us really tying back to our mission. The revenue is very passive. That said, we do have a lot of interest from brand partners to full up and support us completely on that job board. It becomes another inventory option for us that we’re in discussions with this year now that we’re seeing so many more views on that page, honestly, every day.

Jacob: Now looking at The GIST at the corporate level, how much revenue does the business generate in a year? Let’s say 2023, if you want. Were you profitable?

Ellen: We were profitable. Our fiscal is different than our year end. I’m just going to go off of fiscal. We were profitable and we doubled our revenue year over year, which was really exciting. We’re getting to that place of what’s the next stage in our business? How are we investing our dollars? What are we seeing in the market? Similar to, I assume you and also on the Morning Brew side of things, we didn’t necessarily go the VC-backed route. We think that we could be a sustainable business based off of the revenue that we’re able to bring in, and have really thought out an intentional growth and thinking about our growth spend, and our people, and all that sort of stuff there too. We’re growing, which is exciting.

Jacob: To confirm, in a year where a lot of ad based media companies struggled to grow revenue, you doubled your revenue.

Ellen: Yes.

Jacob: Wow. Talking about those ad markets for a second, obviously for many media companies, they soured last year. Many publishers have sought out more direct reader revenue models. Have you thought about this, whether it’s with a subscription, or you mentioned events earlier, that’s how you started with that event. Have you thought about events? Where have you played there?

Ellen: Great question. Early on before COVID, when we were testing and learning literally everything, Jacob, I can’t even get into everything that we tried because some of it is just absolutely heinous, but one of the things that we did try was live events. You know what? They were hit before COVID. We had so much fun, and essentially the whole impetus behind our events was having viewing parties around major sports events and tentpoles. The fact that so many women don’t feel comfortable or so many underserved sports fans or folks who are less knowledgeable in a certain sport didn’t really necessarily feel comfortable going to a sports bar filled with a bunch of avid fans and dudes.

It’s just not really the space or the place that you want to be. A lot of people saying, I would love to learn more about this. We hosted a few Super Bowl parties with partners like Lululemon, for example, or swimwear brand like 437. We would host between 50 to 100 people within their space. Again, free drinks, free food, what have you, small fee to enter. I’d be on the mic commentating on top of the game as well. Sharing and answering a lot of questions about what folks might have on the NFL or the Men’s World Cup was another party that we did in conjunction with a hotel in Toronto too.

We also, in addition to those viewing parties, hosted, which were probably some of my favorite events, we hosted NHL Fantasy for a year. At the beginning of the season, we hosted an NHL pick ’em for the entire regular season. Then we did one for the playoffs. It was the first time that so many of these women were actually invited to be part of it. We did this full snake draft. I have never seen so many people so engaged in one room in a snake draft. It was so much fun. Again, food, booze, entry fee, and safe space with this space of 95% women.

I honestly had never seen anything like it. It was so much fun. We did all of that before COVID. Then COVID did stall things. We haven’t come back to that live event idea since COVID. We’re toying with it. We’re trying to figure out what exactly that could look like for us in the future. We think that there’s an opportunity there. We don’t know if it does look the same as it did in the past, but there’s definitely something there that, I don’t know, maybe you’ll see from us in the next little bit. What was your second question there?

Jacob: Around subscriptions.

Ellen: Oh, around subscriptions. A big thing for us, especially on the sports news side or the college side, is that we want sports to be accessible. A big thing with that accessibility is making sure that they are free for our subscribers. A lot of our newsletter subscribers, again, the average age is about 27. Not a lot of them have cable. A lot of them would have subscriptions to Netflix, Prime, maybe ESPN+, all these separate things. We were really seeing, they’re not necessarily going to be paying for a newsletter in this type of way. The sports biz side, on the other hand, lends itself to potentially a little bit more of that consumer potential side of things.

That’s a place where we’ve been thinking, not necessarily on the newsletter side, but what are some other offerings that we could be doing that would potentially have the consumer pay some of that? Then the last part is we do have merch. We have had a successful merch program and drop over the years, where we’ll have special edition International Women’s Day drops or special edition Pride Month drops and things like that. That has been interesting on the direct-to-consumer side.

Jacob: How do you define a successful drop?

Ellen: Just in terms of our profitability, really. Does it end up being profitable? For the most part, yes. There’s definitely some where we’re like, oh, that was interesting. People weren’t actually into that crew neck, or people weren’t into that tote bag. Then others where they sell out within two days. Clearly we did not manage the supply and demand in the right way. Again, it’s all just about learning what is our audience interested in.

Jacob: Coming back to events for a second, you said you’re starting to think about what are opportunities that might exist. What are the considerations that you’re taking into consideration? What are the things you’re thinking about when it comes to planning out a possible event for The GIST audience?

Ellen: We want to do everything at the highest level ever. We are really zeroed in and everyone on our team is an A++ person. We execute at a really high level. We know from the past of doing events, but also in our past lives in our different companies also hosting a lot of events, that they’re really hard to do. We really want to, as you know too, we really want to make sure that we’re working with the right partners, whether that means an execution agency, whether that means someone internally, whether that means a brand as well to help us on that side of things.

We’ve also seen events and the way that our audience goes to events really, really change over the last couple of years. Before it was a little bit more centered around the community and meeting new folks. Now there needs to be a little bit more of a draw on the talent side of things, or what are they specifically learning. Now that our audience is a little bit more fragmented in that sports news side, that sports biz side, and the college side, a discussion internally is, what type of people are we having an event for?

Is it the sports news Gister? Is it the sports biz Gister? Then from there, what’s the value prop for each of them? Then what’s the revenue opportunity, et cetera? There’s opportunities there, but as for a business that’s supporting itself, you have to stay focused. It’s not a top priority for us.

Jacob: Can you talk about the technology required to power the business?

Ellen: Yes, I can. We have an amazing director of technology, Sam. I guess, yes, we could talk about all the different platforms. There’s content, data, revenue, et cetera, people, all of that stuff. We’ll start off on the content side because that’s mostly where I play. For the newsletter and our website, we recently updated our backend to Sanity, which is basically a headless CMS that– We have really enjoyed Sanity. Are you on Sanity?

Jacob: Morning Brew is on Sanity, I believe.

Ellen: Morning Brew is on Sanity, okay.

Jacob: I hope I’m not wrong about that.

Ellen: We love it. We call it Samity because Sam has done such a great job with it. We recently transitioned to that in November. It has really great connections into our newsletter platform, which we use Campaign Monitor. They talk really well together, those 2 platforms, but we just love Sanity and the opportunities it provides us for new products down the road, which we could get to as well, Jacob, but it gives us a lot of flexibility. That’s on the newsletter side in terms of where our team is actually playing. We create the majority of our content within Google Docs and then pull that into Sanity, and that runs into Campaign Monitor from there.

When we think about our data and how we collect it, where it’s stored, all of that stuff, we use Snowflake, DBT, Tableau for the most part in terms of where all of that is funneled in. Then of course, Campaign Monitor as well and that backend. On the sales side, there’s a lot of different things moving and grooving on that tech. We recently transitioned into Salesforce.

We also use a lot of different tools and platforms to support our revenue team in working with different types of brands and prospecting. Working with Media Radar in particular right now, Sponsor Pulse, what have you on that side. Then from a team side of things, we are a Google company. We’re fully Gmail, Google Docs, all of that stuff. We also started using Notion in September for our team, and Slack.

Jacob: Speaking of the team, how many people are there on the team? Obviously you are self-funded, right? Money comes in, money goes out. How have you thought about bringing on new people in relation to the stage of the business?

Ellen: That’s so funny. We literally were just having so many meetings about this yesterday. For some context and some background, when we initially started The GIST, it was self-funded. When we quit our jobs, it was because we were accepted into this incubator program called the Facebook Journalism Project. It was in conjunction with Facebook and the DMZ, which is the number one university-based incubator in the world. With that, we received $100,000 in non-dilutive funding, which as you know, that doesn’t happen.

Jacob: That’s great.

Ellen: It was $100,000 in non-dilutive funding, $60,000 in ad credits, free office space and access to six different mentors for six months. We were like, oh my gosh, we have to quit our jobs and put 2 feet, 10 toes fully on the ground with this. From there, we were able to raise a friends, family, angel investor round, and also brought in Techstars. We were accelerated by Techstars and Comcast NBCUniversal. We moved down to Philly and that’s when we launched in the US too. Facebook was 2018, Techstars, Comcast NBCU was 2019. Then had some more friends and family come in when Techstars did.

Then we raised, $1 million in 2021. Then two years ago, what’s time, it’s crazy. We were part of the Billie Jean King Enterprises trailblazer program, and so just had a small, I wouldn’t say small, but a decent check come in from that, but we weren’t raising outside of that. That’s our background on our funding. Altogether less than $2 million all up type thing. Yes, less than $2 million. When we think about our team, we are soon to be 26 full-time people. We have about 16 people on the part-time side of things, which is great and it works as an amazing pipeline for us to hire, especially on the content side of things, going from part-time into full-time.

When we think about hiring, when we think about headcount, I think really what you were getting to is how do you do that in a space, in a place like this where your business can change in a day, if someone says yes to a $600,000 package, you know what I mean? We basically, and with help from our VP of people and strategy, Ben, and JC, who’s my co-founder and who leads revenue, we have monthly meetings that goes through all of this on the finance side, looking at our pipeline and what we’re doing. We have a bajillion different scenarios of, if we hit this revenue target and this month, then this is what this means for the cash flow.

Then this is what this means for our headcount. If we don’t, this is scenario number two. If we don’t, this is three. If we don’t, this is four. It really does depend on what did we earn within the quarter? What is our pipeline? What is our likelihood with that pipeline? Then how does that impact our headcount? We feel really comfortable with the team that we have right now and where we’re looking on the revenue side to execute where we want. To grow, you have to also hire people and you have to make sure that you’re hiring. That’s always the toughest part in being self-funded.

Jacob: Looking forward, where do the business over the next three to five years?

Ellen: We are so excited. We feel like right now that we’re just scratching the surface in terms of The GIST and what you’re seeing with The GIST. We always love the example of Overtime, which is a sports media company that really was trying to connect with culture and high school students in particular. When they launched, they were like, we don’t exactly know where it’s going, but we know our audience is going to tell us. They were able to scale their social media, scale their digital media. Then all of a sudden they launched a fricking league.

They have a Overtime Select and Overtime Elite, two basketball leagues for men and young men, and young women. They did that based off of learning for five or six years and then saying, this is what’s next. We’re at that stage right now because we finally have that many people on our newsletter, on our socials to really think about what’s next for The GIST. There’s still a lot of places to play within sports. Especially when you’re thinking about that female fan and targeting them, and really providing them so much more value. For us, we think about a lot of things, especially in the gamification space, in that engagement space of things.

Especially because we know we can do it with our type of fan. We think a lot about, Jacob, that event side of things. We think a lot about supporting the female athlete ecosystem. We think a lot about partnerships and how we can meaningfully engage with different types of media companies. Then there’s those big, hairy, audacious ideas that we have that I’m not privy, that I’m not able to share right now. There’s some big things that we can and hopefully will be able to do with The GIST within the next three years.

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

Ellen: I definitely listened to the rhetoric when I was younger about not going into sports at the beginning because there it was shit pay, shit hours, not enough space for women. Only a certain number of women would enter it. Instead of immediately getting into sports and the industry and understanding everything there, I ended up going the commerce route and ended up going into financial services. Coming into media, I think that there was a point of strength of we really understand this consumer because we were this consumer and we are audience-first. We think that that’s really, really unique.

On the flip side, it’s really hard for us because we were totally new to media. We didn’t have these longstanding connections. We had to learn so much about the space. I’m still learning so much about the space. There’s so many deep-rooted relationships, I think, in the sports industry and the media industry on the whole that’s really helpful when you do get more senior to actually move the needle. I don’t know if I would necessarily– I think that I could probably call it a mistake in the sense of not entering sports earlier, or not entering the media industry earlier, and just listening to, oh, this is how you can make money instead.

Jacob: Second, what is some advice that you would give operators looking to grow their media businesses?

Ellen: This question, I always have a hard time with because I feel like it always depends. I think the biggest advice that I could say to operators is be curious and ask questions, and understand context. We have so much advice thrown at us all the time, we ask for advice all the time, but no one knows your business more than yourself. You have to be open to all of the advice and you have to collect all of the data.

Then you have to apply the data to what you know about your business. I guess that’s my advice, is just take in all the data that you can be curious, but then really think about how you consolidate and act on that data based off of your business in particular. Then I think just surrounding yourself with really amazing people who bring you joy and who you want to work with every day.