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Aug. 17, 2023, 3:57 p.m.

What’s it take to make a great daily newsletter? Axios’ Kendall Baker is planning to bring one to Yahoo Sports

“I believe, if we do our job as well as we can, we’re going to make sports fans into even bigger sports fans, and we’re going to make people who aren’t yet sports fans into sports fans.”

I probably subscribe to 20 different morning email newsletters. Some are well-crafted editorial products; some are just a list of links some algorithm strung together. If you’re like me, there are some you look forward to opening — and others that feel like homework.

Axios Sports was one I looked forward to opening. Not just because it was about sports — because it was a crafted, considered editorial product that became a little a.m. ritual. The main man behind it was Kendall Baker, who’s had one of the more interesting journalism careers of the past years.

At tech site The Hustle, he’d launched a daily newsletter — and thought there was an opening for something similar in sports. In 2017, he started one with the infelicitous name of Sports Internet, and within a few months, it came to the attention of nascent newsletter giant Axios. (As you’ll see, he made sure it came their attention.) They bought it and rechristened it Axios Sports.

But Baker now has a new gig. Last month, he was hired by Yahoo Sports to head up its newsletters, which will include launching a new iteration of what he’s been doing daily since 2017. Axios CEO Jim VandeHei took the loss gracefully, saying Baker “was, is, and forever will be one of the great entrepreneurial minds in sports journalism. He dreamed up an idea and willed it to life daily.”

I talked with Baker recently about the sports media landscape, what attracted him to Yahoo, and what it takes to create a daily newsletter habit in someone. Here’s our conversation, which has been edited for length and clarity and lacrosse references.

Joshua Benton: Researching you this morning, I found what’s probably the most important tweet of your life. The tweet you sent to David Nather from Axios in 2018. “Hey David, are you guys considering getting into sports coverage at any point? I currently publish a daily sports newsletter that many readers have told me is ‘Axios-esque’…Would love to chat!!!” What do you remember about why you sent that tweet?

Kendall Baker: I literally had heard from a handful of people — both readers and also like, my sister, who was a big Axios reader — that they had a lot of the same philosophy I do when it comes to newsletters — keeping it really short, really tight, really efficient.

When I’d set out to start Sports Internet, I had a very specific goal: I’m going to hit 25,000 subscribers, and then I’m going to go raise some money and hire some people. I really wanted to build out a full-fledged media company. And right around the six-month mark, I would say, is when I started to feel like: Hold on, I’m really enjoying the writing part of this more than I thought, the putting it together every day. And that’s when I started to think maybe there would be an opportunity to bring this somewhere, that someone would want to buy this newsletter. Obviously, Axios wasn’t in sports yet.

Benton: Yeah. I remember when Axios Sports was announced thinking that, as much as Axios had already expanded by then, it was still pretty squarely focused on the A Section of the newspaper, hard news, as opposed to the rest of the newspaper mix. There wasn’t an Axios Gardening, or an Axios Movie Reviews, or whatever. Why were they interested in adding sports?

Baker: What really sold me was the fact that they were really big believers in the product. The idea is that there’s this huge amount of news created every day and Axios is going to help guide you through all the noise. It kind of felt like I was solving a similar problem for sports news consumers and sports fans and for people who work in sports. I think they saw that what I was doing with my daily newsletter was kind of the similar thing to what they were doing — valuing your time, making it easier for you, providing a lot of utility. So I think it made sense philosophically, for both sides.

Benton: At that point, how many subscribers did you have for Sports Internet?

Baker: I forget the exact number, but it was somewhere in the 15,000 to 18,000 range when I sold to Axios. But the stat that I took most seriously was the open rate, which was like 63%, which is really high. I did no paid acquisition during that time — so those 18,000 subscribers were all organic. I’ve done a few cross-promotions with other newsletters, but that’s all. So talking with Axios, the narrative wasn’t just that you’re buying 18,000 emails, but that you’re buying a community that’s already been built, that’s already super engaged, where almost two-thirds of them are opening this newsletter literally every weekday morning.

Benton: Back in this time period, 2017, 2018, who was your competition in terms of daily sports emails?

Baker: Well, a big impetus for me starting this was that there really wasn’t much competition, quite frankly. And there’s still not as much as you’d expect, despite all the growth within the sports media world. Part of the reason why I was excited about Yahoo is that I still don’t think that the biggest players in the sports media space have really taken swings in the newsletter space. So I’d say it’s fairly similar now to what it was then. There were a handful of independent newsletters. There was one called The Lead. There was one called Casual Spectator. But there wasn’t much.

I’d been in the daily newsletter space for a bit and I kind of understood the business. But then, specifically, I was like: Wait, I used to watch SportsCenter all the time. Now, all of a sudden, I’m an adult, I’m not in college any more with all that free time. But for the first time, I’m actually struggling to follow sports. I reached out to a bunch of my friends: Hey, do you guys ever watch sports anymore? They were like no, I don’t have time for that. And I said: What if I basically did SportsCenter in a newsletter? You can read it on your way to work or something? They thought that was cool, that they’d definitely be interested in that. So that was really the impetus for it. And to this day, you know, ESPN still doesn’t have a go-to daily newsletter, which is crazy to me. They tried it and shut it down.

Benton: Why do you think a giant media company, ESPN or whoever else, wouldn’t see the opportunity?

Baker: So newsletters are obviously becoming more and more popular. Publishers are seeing them as table stakes. “Okay, we need a newsletter.” But I still think publishers vary widely in how they think about newsletters. So, at Axios, they have a firm understanding that newsletters are editorial products. You can create and design this great editorial product that, you know, for many of your readers, is like you’re sending them your website over email, as opposed to sending a bunch of links to come back to your website. For a lot of publishers, the thing they’re valuing, their KPI, is how many people can we get to click out of this email and onto our site or our app or whatever. So I think some publishers still view newsletters in the same bucket as, like, email marketing. It’s about driving traffic back to the site, versus creating the best editorial experience you can in the email. So they end up creating a newsletter that’s not really a newsletter — it’s a funnel. It’s not meant to be a great editorial product that stands on its own. So I think in the case of ESPN and others, some of the newsletters they’ve launched, in my opinion, weren’t ever going to be too sticky because they were just links.

Benton: So at the same time that we’re talking about, a big theory about sports media was that, thanks to Twitter and other social media and streaming, everything is happening live and in real time, and as a result, nobody wants to watch SportsCenter any more or read the sports section the next morning. People already know who won the game last night. But at the same time, you were framing this as a version of SportsCenter for a new medium. And it’s interesting to me that there was an opening for a once-a-day recap of the day in sports in people’s inboxes at roughly the same time that opening was closing where it had been for the prior 30-plus years.

Baker: I think it’s a few things. I think fewer and fewer people want to sit down and watch a full hour of content like SportsCenter. The difference between that and what I’m doing is I’m basically saying: Okay, what if I watch SportsCenter for you, and I pull out the best stuff, and I put it in this email that you can skim or you can read as deep as you want. I’m not asking for more than five to 10 minutes. There’s no commercials to sit through. I think a lot of the best daily newsletters lean into the utility of it, of curation. I can really provide a lot of value to folks. Obviously, original reporting is part of what I do. But I can provide most of my value by like watching all the stuff, reading all this stuff that you would probably enjoy if you got around to it. But I know you don’t have time to do that. So let me do it for you and pull out the highlights and put it into a really easy, digestible format for you. You ultimately end up getting a similar experience with a fraction of time required on your end. You’re providing utility to your readers by quite literally finding the stuff that they would have found if they spent an hour on Twitter.

Benton: I’m curious how you have thought about the role of your own opinion or your own voice in your various newsletter products. I was a little surprised to see on your LinkedIn to see that your your first job listed was as a columnist at BleacherReport, because I don’t think of you as having a “here’s my take on what happened” kind of a voice. In a lot of sports media, from First Take on down, the columnist’s voice or the analyst’s take is absolutely central, for better or for worse.

Baker: First, I just don’t think we need more of that. If somebody wants that, great. And TV is the right platform for it, the back and forth. I don’t even want to play in that space. But more broadly, I’ve always thought of weaving my voice in by being your guide, through this newsletter that I’m delivering every morning. I’m kind of letting the news speak for itself. Obviously, I’m adding some of my opinion by choosing the stories that are in here. But I mostly think of my job as guiding you through the news.

I’ve always enjoyed leaning into the fact that I’m a huge sports nerd. I love sports. And I think that’s kind of the personality that I want to show my readers — as opposed to having takes all the time. Personally, I find it exhausting as a sports fan. Sure, there are times when you want that, but if I’m reading something on a daily basis, it just feels like too much in the morning for me to be disagreeing with you about who the top 10 quarterbacks in the NFL are. There’s enough of that being produced on a daily basis. I don’t need to contribute to it.

Benton: So who do you consider your competitive set now?

Baker: Well, I would say The Athletic is probably my biggest competitor. When I started Sports Internet, and even just a few years ago, The Athletic didn’t really have newsletters, in the sense of editorial products. They had automated digests for your teams. Now they have more newsletters — they have The Pulse, which is essentially what I do, a daily national sports newsletter. They’ve launched a few more newsletters specific to leagues or verticals. I’ve long thought that verticalized newsletters would be an interesting business because sports is so naturally verticalized, so I’m definitely watching what they’re doing

But as I said, it’s shocking how few competitors there really are in the general-interest sports space. ESPN doesn’t have this kind of daily newsletter. It doesn’t seem to be a priority at Sports Illustrated. Maybe The Athletic is the best example of a place that seems to be really investing in it. But that’s why it excites me so much go into a place with the audience size, with the scale with the resources of Yahoo. What would it look like if one of the big sports media players really took a big swing at newsletters — you know, in a way that Axios did for politics. I just think we’ve yet to see what that looks like, and I hope we’re able to do that.

Benton: So Yahoo does have a huge audience — overall and specifically within sports. How do you see the Yahoo audience? I’ll confess that, despite that huge scale, I don’t think about them as one of the biggest players in digital news often — as a place that sort of has its own gravitational pull, editorially. Who is the Yahoo Sports audience, and what are you hoping to do with it?

Baker: It is a massive audience, as you said, and I’m really excited. My goal with this newsletter from the jump was to make it extremely easy and enjoyable for as many people as possible to follow sports and, hopefully, kind of fall in love with them and enjoy them the same way I do. And so, not to sound too simplistic, but I’ve just always wanted to get as big an audience as possible. I believe, if we do our job as well as we can, we’re going to make sports fans into even bigger sports fans, and we’re going to make people who aren’t yet sports fans into sports fans.

So that’s a big thing for me — just straight up a bigger audience to serve. And it’s a very loyal audience — you know, Yahoo Fantasy is a big part of the sports division. And anytime you have audience that’s already as engaged as fantasy players, I think we really have a chance to be, like, the first place a sports fan should be reading in the morning to get themselves set for the day. Whether it’s about their fantasy lineups, or the news of the day, or something about their team, I just think we can do a really good job of serving a really big number of people.

The way I’ve described it is I want to help you get your bearings in the morning. Here’s what people are talking about, here’s what happened last night, here’s what’s coming up tonight. Here is this interesting detail, but also here’s the big picture. Ultimately, I want people to come away from my email with a kind of a calming sense — like, “Oh, okay, I’m caught up on sports. I know what’s on tonight, that big thing happening tomorrow morning.” Giving people a constant sense of what’s going on, giving them their bearings every morning, helping them be a better sports fan.

Benton: There really is something about the email that’s feels light in a way. I don’t mean light like there’s no substance — but I mean you come away from it feeling you’ve had a nice sweep of the world. You have the big news of the day, but you’ve also got this crazy highlight from, like, Division III lacrosse, or some odd sport you’ve never heard of, or something that’s unexpected.

Baker: I appreciate that. I’d often get asked why we were covering all these sports — like, why aren’t you doing more on the NFL? We could always lean more and more into the big sports. Like, if you watch a sports talk show, they’re gonna talk about the NFL, like, probably 80% of the time. I just think that part of why I love sports is that sports is the most natural form of storytelling. They’re stories that play out in real time. This is the real reality TV. And so I think the beauty of it is that on any given day, the best story in the world of sports could be on the D-III lacrosse field, or it could be on Monday Night Football. I think it’s my job to make sure that you hear about the D-III lacrosse story. We really do cover everything — we will cover cricket, we will cover sports you might not hear about elsewhere. And I think that opens us up to more and more great stories. I can’t even tell you — even during the pandemic, when there was quite literally no sports, I don’t think there’s a single day over the last five years when I was short on material. There’s always too much. And I think that’s a result of being open to sports stories of all kinds.

Benton: I think you’re absolutely right to think about email in the context of utility. On the surface, it’s odd, because, like, the people who read Politico Playbook for utilitarian reasons are lobbyists, right? Or members of Congress, or their staffers, or people who are deeply engaged in politics. They’re getting intel, right, that’s connected to what they do all day. Whereas sports, fundamentally, doesn’t have a lot of “utility” in the sense of making you better at your job or informing your key decisions. But the “utility” it provides is the emotional experience of stories, seeing people do amazing, dramatic things. And that’s the utility here. It’s not the same sort of utility that The Wall Street Journal offers a stockbroker, but it’s still utility.

Baker: Totally. My one pushback is that there are a lot of people who work in sports business for who the email can have that sort of Playbook utility. But yeah, I would argue that the utility I’m providing is that story they read about that makes you feel good, or inspires you. Maybe it makes you reach out to your brother, your dad. I mean, I hear from so many people — like, we have a trivia question every day, and I’ve had people say “I’ve been doing the trivia question with my dad the past year, it’s really, like, helped us get closer.” Or during COVID, when there was no sports going on, we asked readers to send in their favorite memories from sports, and like, half of them like made me cry. Sports really does open you up to these emotional experiences.

Benton: Last question. You’ve spent a number of years trying to build up a daily habit in your readers. Trying to figure out what makes people do something once a day, over and over again — something that was very natural in print and TV. If someone told you they were going to start a daily newsletter, what would you tell them? What can you do as a product creator, to engender those sorts of habits and people?

Baker: Well, I think first and foremost — and this is somewhat assumed, but I think it can’t be said enough — is consistency. I don’t think everything needs to be a daily newsletter. Not everything should. But if you’re going to be daily or weekly or biweekly, make sure it’s delivered roughly the same time every day or whatever. People need to be able to trust that you’re going to be there. So, again, that’s very kind of an assumed thing, but I think it can’t be stressed enough.

You also have to make sure that people know what they’re getting. So, for example, with Axios Sports, there were 10 items every single day. No. 9 everyday was a trivia question. No. 4 everyday was what we call a lightning round, a roundup of quick hitting stories. There was a lot that could change from day to day, but we had enough that was consistent every day. When people get that push notification on their phone, or they get another newsletter from me, there needs to be a balance between “Oh, I know what this is going to be” and also “I’m excited to see what’s in it.” I think that’s gold, if you’re able to do a little bit of both. Because if you’re too predictable, and your newsletter follows too much of, like, a rubric that you’re filling out every day, then it could get stale.

That also applies to length. If some days your newsletter is 1,000 words, but some days it’s 4,000 words, people won’t have enough of an expectation set and they’re not going to feel as comfortable opening it. There’s a comfort factor, I think. Striking that balance is easier said than done, and it certainly takes some tinkering and testing and getting feedback from readers and just simply repetition — but if you can find it, I think it’s kind of gold.

Benton: That length disparity drives me crazy with so many Substacks. Sometimes it’s a paragraph, sometimes it’s 8,000 words.

Baker: Yeah. A lot of Substacks, to me, are basically just blogging. You remember, in the blog era, you could publish the blog post and there’d be an option to also send it out by email. I feel like all we’ve done is flip it: Now it’s like you send the emails by default, and there’s also the option to read it online. A lot of things on Substack are less newsletters than a blog that gets sent to you by email. When I think of quote unquote “newsletters,” it’s more of an editorial product with some sort of a template and some sort of utility, versus just a place where you can put your writing.

Joshua Benton is the senior writer and former director of Nieman Lab. You can reach him via email (joshua_benton@harvard.edu) or Twitter DM (@jbenton).
POSTED     Aug. 17, 2023, 3:57 p.m.
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