🎧🍌 The Business of Newsletters with Kendall Baker "The Sports Newsletter Guy"
The history of newsletters, why he spends $0 on growth, how to sell a newsletter, why the NBA commissioner reads his writing, the momentum in US soccer, and Yahoo's comeback
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In this latest episode of The Peel, I was joined by a very special guest: Kendall Baker. Currently, Kendall leads Yahoo’s sports newsletter business. In 2017 he launched the first daily sports newsletter called Sports Internet, which he sold to Axios in 2019.
Before Sports Internet, he convinced the founders of The Hustle to focus their online tech blog on a daily newsletter, which he wrote for a year and a half. Prior to that, he produced SportsCenter at ESPN.
Kendall has spent nearly a decade at the intersection of daily news and sports, and this episode is packed with insights on both.
In this episode, we discuss:
The history of the newsletter industry
Why the best writers delete more than they write
How he got on SportsCenter
A crash course on the sports media business
How to write a daily newsletter
The importance of experimenting
Why Kendall spends $0 on growth
Getting the first dollar of revenue for his daily sports newsletter, Sports Internet
Why NBA commissioner Adam Silver reads Kendall’s writing
Selling Sports Internet to Axios
Why Yahoo’s the next rocketship
The surging momentum in US soccer
And the most underrated athletes - current and of all-time
Follow Kendall on Twitter
🙏 Thanks to Zac and Xavier at Supermix helping with production and distribution!
Transcript
Find transcripts of all prior episodes here.
Turner Novak: Kendall, how's it going? Thanks for joining me today.
Kendall Baker: It's good, man. Thanks for having me.
Turner Novak: I'm excited about this. I've been an observer/reader of your content for a while. Can you kind of give us a history of this whole newsletter industry and maybe specifically what's going on in sports also?
Kendall Baker: Sure. Yeah, so I think I can speak to the newsletter industry pretty well, just because I've kind of been there for a few of the different stages. The first time I became aware of newsletters as a business model and not just something that a media company has, or something that somebody writes, but as a foundational piece of a business, if not the entire business was The Skimm. I had a friend working there and so when I graduated college in 2013, that’s probably when I first became aware of it.
Turner Novak: And what was The Skimm?
Kendall Baker: The Skimm was one of the first newsletters that was really kind of a daily newsletter product, taking the biggest headlines and explaining to you why they matter. It was very brief, and it was more so targeted towards women.
They were the first success story in terms of a daily news-based newsletter that was really their entire business. They ended up building some things around that, but still, to this day, it's very much their core business model.
That was the first time I became aware of that, in 2013. I was working at ESPN at the time and funnily enough, as you know, I did end up launching a sports daily newsletter, but at that time I had the thought of “What if you did this, but for sports?”. So that was always in the back of my mind, and I ended up acting on it later.
2013 is when I'd say you’d see The Skimm, and I think there were a few others that were starting to pop up, and you could say “Oh wow, you can build an entire business around a newsletter.” You could have a pretty lean team, but also probably bigger than people think if it's just this one product.So that's 2013.
Two years later, I ended up at a company called The Hustle which at the time was a blog. We had four employees, and it was a tiny business out of a little apartment in San Francisco, and our newsletter at the time was more what you would see back then, a display of the best articles we wrote any given week.
It was more of a curated list of our stuff as opposed to original reporting that you hadn't seen elsewhere. I actually pitched the founders of the business on, “Hey, what if we did a daily newsletter where we just covered the day’s headlines, kind of like what The Skimm is doing?”
We ended up launching that in 2016, which is around the time you’d start to see more Skimm copycats, or just more businesses realizing that “Hey, we're creating a ton of content and then we're putting that stuff into a newsletter and sending it…What if we just sent the newsletter?”
I think you saw a lot more businesses realize you could have a leaner team and cut through the noise. I think one reason why newsletters have been so effective is people realized, “Oh, everybody's kind of overwhelmed with information, even your own content if they're a big fan of your content. Why don't you just give them the best stuff to begin with that you can then build an entire business around?”. So that's 2015. You started to see more copycats.
Turner Novak: What was the business model then at the time? Could you just get a bunch of eyeballs, a certain amount of opens per email, and then start to monetize with advertising?
Kendall Baker: Exactly. At the time, and to a certain extent this is still the case, if not even more so, you could get higher CPM rates on newsletters.
So if your business was a blog and you sold banner ads, you would pivot to a newsletter and create similar content, obviously a little shorter, and tighter. You're going about it in a different way where you're sending one thing versus publishing multiple articles throughout the day.
You could essentially run the same business with more eyeballs and higher CPM rates. It was a kind of an easy pivot for some folks.
Turner Novak: That's fascinating. Why were the CPMs higher? It doesn't make sense.
Kendall Baker: That’s a great question. I think many people would have many different answers. My assessment is that there was already starting to be, and it's even more so now, this sense around the industry that nobody was looking at banner ads. There were studies that came out that said that our eyeballs are now trained to block them out – nobody's looking at them.
I think there was something, and this is still the case, that was new and exciting about a newsletter. It’s more of a community, people were reading it, and it’s more of a habit. With newsletters you could create more of a voice for your brand. Advertisers were really interested in putting themselves in that newsletter that really had a voice, and really had a connection with the reader.
They were drawn to the fact that the reader was opening it almost out of habit, like at their job every morning with their coffee as opposed to maybe coming to your site. There was something attractive to advertisers about being aligned with this product as opposed to maybe a website.
Turner Novak: One of the reasons Facebook and Instagram ads probably do so well is that people habitually open the app many times a day. Email is probably the same, where if you send someone an email, they might not open it, but they'll see that you sent them an email and because they’re always returning, you can almost guarantee that people will read it and see it.
Kendall Baker: What I've always said about the daily newsletter specifically is that it is the most habit-forming media product there is. Even more than a daily podcast because somebody can open a newsletter on their own time. They can use it in the way they want.
Whether they want to read every word, just the top story, or something that leads them down a rabbit hole. It's more of a choose-your-own adventure, and I think people are much more likely to open that out of habit every morning. I have so many readers who tell me “I read your newsletter every day over coffee,” or “I read your newsletter every day on the train to work.”
They also know when to expect it. It shows up on an app that they check frequently, an app that shows up alongside their coworkers, their boss, their mom. It comes to them in a place that feels very organic and very much one-to-one.
Back to the history of newsletters – in 2015, you see a lot of media companies starting to use newsletters as their core business, or one of their core business revenue streams. Then, between 2015 and now, there’s been this shift. Media companies made a shift to “What if I did this on my own? What if I did this with two, three people and made it a small, one-to-three-person operation?”
They realized “Okay, we can create an entire news-based media company with just a handful of employees.” That's how Morning Brew started. That's how I started Sports Internet, which ended up getting acquired by Axios. It was basically realizing “Hey, I can kind of do the entire day's news myself or with two people or three people.”
Newsletters were the perfect medium for that. I’d say between 2016 and 2019, you started to see more people, whether they were ex-reporters at media companies or didn't really have any experience journalistically, realize that they could start up a daily newsletter and grow it pretty effectively.
I'd say the biggest change I've seen has been within the last four years, which I’ve had to observe from afar because I’ve been working at a media company and not really in the weeds, has been the introduction of tools like Substack and Beehiiv that have made it way easier to start newsletters.
They’ve created the network effect that happened with podcasts where you can see what the top newsletters are. You can see that on Substack, in a way that you couldn't before. You can discover new ones in a way you couldn't before. There’s this ecosystem that's been created and these tools that have been created that make it extremely easy to not only start a newsletter but also to then find similar newsletters and share an audience with those people.
What has gradually become apparent to people is that newsletters are a very effective medium. And what's happened recently is that it's just become incredibly easy to start one – well maybe not incredibly easy but it is much easier to grow one and to find new readers. People are just very interested in newsletters in a way that they weren't before in terms of a discovery standpoint.
Turner Novak: What makes a good daily newsletter or just a good newsletter in general?
Kendall Baker: There's a few things. One of which, and this applies more to some people than others depending on subject matter, is pairing a daily newsletter with a very distinct voice is extremely effective. Like I said before: you're sliding into people's inboxes, if you will. You’re sliding into their DMs.
Often, a lot of newsletters comes from your name. Some people still have it come from their company, but mine at Axios, for example, came from Kendall Baker. And so if you have somebody getting essentially an email from you, Why not lean into personality?
Now I covered sports and that's easier. I think if I were covering politics, for example, maybe you don't lean as much into that because if you're a political reporter you don't want to be the story. You want to be as unbiased as possible.
There’s always a way to sneak your voice in there, and to make it personal. As somebody who's been writing newsletters forever, and anybody who has been doing it can relate to this, people can reply right to you.
And so again, it’s important to lean into voice and to lean into the fact that there's a human on the other end of this. I can't tell you how many people over the years will reply to my newsletter, and then I'll reply back to them, and they'll be like “Oh my gosh, you replied!” and I'm like, “Yeah, this is my email.”
Turner Novak: Yeah.
Kendall Baker: Somebody will reply hating on you or telling you how dumb this thing was, and then I'll reply saying “Thanks for the feedback, really appreciate it.” And they'll all get back to me saying “Oh my gosh, I'm so sorry. I didn't mean it.”
Turner Novak: Oh, geez. Yeah.
Kendall Baker: Like most things, they don't expect a response. Maybe they don't even think anybody is going to ever see this and they’re kind of just getting it out, whatever they need to get out. And then I come back to them with a nice little message and then they immediately retract it.
Turner Novak: That helps boost your deliverability in their inbox, right? Like when people reply?
Kendall Baker: Deliverability, but also the second somebody has a conversation with you, they feel even closer to you. And I don't have exact data to back this up, but I promise you when people who have interacted with me on my newsletter get a response from me, they become much more loyal subscribers because now they feel like a connection with me.
I had one guy over the course of the last five years who replied to almost every single one of my newsletters, and even though I've never met him it feels like we have this kind of pen-pal-like relationship.
There was another person who for a three-month span would grade every one of my newsletters on a scale of one to 10. It was kind of awesome. Even though I didn't want to read too much into it because it's one person, when he gave me a low score it was definitely maybe something to consider.
Turner Novak: Was it just a pure number or would he be like, “I give you a five because of this?”.
Kendall Baker: Sometimes there was a reason, but other times it was simply just like 8.2. It was pretty awesome. That just kind of gives you a sense of like the relationship you can build with a reader, with a newsletter. And back to my point of having a voice – if you're going to build that relationship and lean into that relationship, you should lean into who you are.
I think another thing that makes a daily newsletter effective, and this is very on-brand for my previous employer, Axios, but it's true, is to make it short. Over half of all email subscribers – and this is data I've seen – are reading on their phone.
If you think about it – and this is true for articles or any reading being done on someone's phone – if they can't see the bottom of the paragraph they're reading, there's a much higher chance that they're going to jump ship because that's just how attention works. Now, the second somebody gets bored, if you're not immediately jumping them to the next thing, jumping them to the next thing, getting to the next thing, the chance of them leaving is much higher.
With emails, newsletters, there's so many of them now, a lot of people are inundated with them. You have to be able to deliver your message effectively, efficiently, and communicate to them and say “Hey, I value your time. I know you're busy.”
I think it's really helpful. I think, people have a bad habit of writing too long. They get too obsessed with their own words, and I've kind of grown to kind of be obsessed with deleting my own words, and treating newsletters like every pixel matter.
One of the great things about newsletters is they're extremely bare-bones, and they're extremely limiting. Some people will complain, “Oh, I wish I could embed video in my newsletter. I wish I could do all these things,” and yeah that would be great, but I think there's something to be said for the fact you can't do that.
You have to focus on the written content, on the images, on every small little detail. And what happens is you end up treating it more like a piece of art than just like a blog post. And I think that goes hand in hand with length. If you're really intentional about every word you put in that newsletter, every image, everything is just really thought through.
You create something that's just a real joy to read and that people can kind of look forward to reading it in a way that people these days don't look forward to reading much, because everything, well not everything, but there's still a lot of things are just really long. It’s a hard truth for us to accept as writers, but there's a very good chance people are going to bail on you after the first paragraph.
Turner Novak: Yeah, it's very counterintuitive, but the top advice or feedback I get from anyone on how to be a good writer is to write less.
Kendall Baker: It’s true and I think if you take the New York Times, for example, I love the New York Times, but The New York Times trains writers in a way to write for newspapers. If you look at a typical New York Times story, the first paragraph is kind of like it's the person trying to win a Pulitzer Prize, in my opinion. That's how I describe it to people.
It's like, perfect words, big words, beautiful, beautiful prose. But the point of the story doesn't start till the second paragraph in. That's how newspaper writing was done. You have to go along to get on the front page. That's counterintuitive now.
The best advice I give to people is, instead of starting with that long, winding, nicely put-together paragraph, why don't you just start with what people click the headline for? What happened? Or what's important?
This is very on-brand with my former employer, but part of the reason why I joined Axios is I very much agree with this way of thinking, which is that people are busy. The most important thing you can do to create brand loyalty with readers is just value their time.
Turner Novak: It's interesting when you talk about the New York Times. There'll be times where I will read The New York Times, CNN, or some other legacy publication, and there's just some super juicy stat or thing that's buried two thirds of the way through.
Kendall Baker: You can reverse engineer this. In this example I'm about to give, the New York Times did the hard work and so they deserve credit for it, And of course, you know, nothing irks me more than when people essentially take something from somewhere else and make it very vague that they got it from that source.
Be upfront with the fact that, you know, “It's via the New York Times!”. That's very easy to do and you'd be surprised how many places don't do it. But to use your example, if I read an article like that in New York Times that was a 1500 word piece with one stat in the middle that was jaw-dropping, I would reverse engineer that to share the stat and then tell people if you'd like to read the whole article, go here.
Some people want and read the whole article, and that’s great, but if you surface the most interesting point, even though most people aren't going to read the full article, at least they got that from it, and then the people who do want to read the full article can do so.
It's kind of simple when you think about it but there are reasons why publications don't do this. And I understand those reasons, but I just think if you're writing on the internet these days, the single most important thing you can do is just learn to write shorter and learn to be more efficient with your words.
Turner Novak: It is good feedback. And after talking about this for a couple minutes, it's made me reflect, I could probably cut things a little shorter. I have a weekly newsletter – that's probably how about half the people who listen to the podcast get it.
Kendall Baker: It's not black and white. And I also think that weekly maybe people are looking for something different. I speak a lot to daily newsletters because that's what I've been doing. You really have to value people's time because they're busy.
They're usually reading in the morning before they get to work. They want efficiency, they want, like my readers, for the most part, talking points so that when they talk to their friends, at work that day or whatever, to be up to speed. They want to be ready to talk about stuff.
Weekly newsletters, you could think about more like magazines maybe, and therefore writing longer isn't necessarily a bad thing,
Turner Novak: If you set the expectation of “all of our content is very long...”, like have you ever listened to the Acquired podcast? They do like three, four-hour episodes. You're not going to finish those quick and you're going to learn the history starting from the 1800’s of some massive company, and it's going to be a thrill. Interesting along the way, but it's not quick.
You'll learn a lot. They’re all really, very well done. And they told me that they cut so much. Like they'll go in and they'll record for hours a day for multiple days, and they'll cut it down to three or four hours. So, it's just like, you want to keep your content high quality.
Kendall Baker: High quality, and I think you made a really good point: set the expectation. As long as the expectation's set, great. I'll give one more example about the Acquired podcast or some of these podcasts.
You see different podcasts who have made a whole account based out of “I'll go listen to that three-hour podcast because you're probably not going to and I'll give you the highlight.” And that's kind of back to my original point. If you're creating content that somebody then is going to go and then boil down to the talking points. Isn't that signaling to you that you could just do the talking points?
Turner Novak: It's interesting though because it's a growth channel for that podcast where they don't do anything. They just put it out and someone else does the work of, “Hey, listen to this episode.” It’s an interesting trade off.
Kendall Baker: The Business Insider format is Headline, and then they'll do three to four bullets of basically the highlights of the story you're about to read. Sometimes I'm like, so why should you read it now? I think I'm good now.
Turner Novak: Yeah, well then, they throw the paywall on you too. I think one of my best tweets ever is if I ever get canceled, I just hope it's on Business Insider because no one will read it.
Kendall Baker: (laughs) I love that.
Turner Novak: So another question I have just about the newsletter in general, how do you think about analytics versus intuition? Because Substack has okay analytics. They probably expand on what was there.
And then when you look at a new product like Beehiiv, you can get very, very analytical, almost to the point where it's maybe not helpful because there's just tons you can do with it, and you could probably smash your head against the wall for a day just diving in all your analytics.
How do you think about the artistic creativity side and then also just the pure numbers?
Kendall Baker: It's a great question. I think your point there that I would echo is that with anything, if you get too into the numbers, you're going to drive yourself crazy.
I think ultimately your content is going to speak to the fact that you're too into the numbers – it's more robotic. Going back to my point from before of leaning into personality, I think that goes hand in hand with the artistic versus analytical side of just trusting your gut, seeking feedback from readers, doing things that aren't necessarily like analytics based or even scalable, quite frankly, like trying to respond to as many people as possible.
I think it all goes in the same bucket of just like art versus analytics. Now obviously some analytics are very important. It depends on what your newsletter is and what your KPIs are.
Obviously at Axios, for example, we have open rate, which is extremely important. You also have click-through rate, which is extremely important…
Turner Novak: That’s how many people click a link, right? Open rate is how many people open the email, click-through rate is percentage that actually interact?
Kendall Baker: Exactly. What’s interesting though is with the click-through rate, it shows high engagement, right? Because that shows somebody didn't just open it, they're clicking something like they're clearly engaged.
However, if I did a good job on my newsletter at Axios, one could argue that people shouldn't have to click on anything, right? Because a lot of times if they're clicking on something, it’s because I said “Hey, here's the full scoop! Go deeper if you'd like.” So you could argue that if my click-through rate's zero, it's a perfect newsletter.
There were plenty of times when I was like, “Hey guys, go read this article. Hey, go look at this highlight.” So that's one metric that can be hard to read. I don't really know what I'm optimizing for there.
There are plenty of newsletters where the whole goal is to get people to the bottom and click off and go to whatever. If that's what your goal is, then look at that, not just click-through rate, so you can see how many people click that specific link. Then obviously you want that as high as possible.
Email is relatively minimal in terms of the analytics you can get. You're not going to get a heat map in the way you can with a website. You can't see where people are spending their time. You can really just see how many people opened it, who opened it, what'd they click on.
And so leaning into that as much as you can without driving yourself crazy is obviously a smart thing to do. For instance, I found it much more valuable over the years in terms of feedback, to just straight up ask my subscribers via poll or via asking them to just reply to me directly.
Like, “Hey, like what do you want to see more of? What do you want to see less of?” And I know that's not the most effective way on paper to get data and get feedback, but I just found that to be extremely helpful.
It also signals to your subscribers, “Hey, you're part of this too.” If you're just on the backend looking at your dashboard, reading the analytics all the time, you're not really involving your readers in that, whereas if you're asking them every month, “Hey, like, what was your favorite story this month? What did you like? What didn't you like?” Then they feel like they're part of it. It can be much more valuable.
Turner Novak: Let's say, for example, you never covered soccer, and so based off the analytics, no one's ever clicked a soccer link. You don't know that anyone wants soccer. But if someone says, “Hey, put some soccer in there,” and then it starts doing really well and it shows up in the data, you would never know.
Kendall Baker: This would a good example of why writing short is so great. If people don't like soccer – and I cover every sport so to an extent, everybody's got their sports… most of my subscribers, I'd argue, like all sports – but the stories are so short that if you're scrolling and the third story is about soccer and you couldn't care less, you take your thumb and you scroll
Turner Novak: One scroll. Yeah.
Kendall Baker: That's what I tell people all the time when they ask “Why are you covering this?”, I just tell them to scroll past it.
Turner Novak: Your newsletter always sort of reminded me of the newsletter version of SportsCenter.
Kendall Baker: I love that. That was how I initially marketed it.
Turner Novak: SportsCenter back in the day, I mean, I was born in 1991, so I grew up in the 90’s/early 2000’s. You’d wake up at 5:00 AM in Canada and we TSN (The Sports Network), (you’d have ESPN in the US), and it was actually awesome because the coverage was mostly hockey when in Canada.
Moving to the US was interesting because all of a sudden they started showing all these other sports and I was like, “I don't care about baseball, I don't care about like all these other things. Just show me an hour of hockey highlights.”
That was the interesting difference with Canada, it was probably 50 minutes of hockey. They'd show like five minutes from each game and at the very end they'd be like, “Oh yeah, the Super Bowl happened. And LeBron dunked or something”. They wouldn't care about it.
Kendall Baker: I grew up watching SportsCenter. They just replayed SportsCenter all day. I would watch SportsCenter like three times a day. But also at that time you weren't finding out who won the game right when it ended. You actually tuned into Sports Center that night or that morning, and you didn't know what had happened yet. And that was a magical time.
Waking up and reading the sports page – I have so much nostalgia for that because I would wake up and be like, “I don't know what happened, like who won?”. I would read and obsess over the stats, whereas now we do that right away. We see what goes viral – Messi's goal five seconds after it happens. We don't have to wait.
But I will say what's still valuable to people is putting everything in one place. When people read my newsletter, even if they've already heard about half the stuff, it’s still fine. They already saw the Messi goal, for example, but if I can add that one piece of context that they hadn't heard related to that, then that's still beneficial for them. They're still going to find something they didn't know.
But it is interesting you say that because yeah, when I first started Sports Internet, which is what Axios acquired, and this journey I've been on, part of the reason was that I’d been a sports nerd my whole life.
I worked at a Bleacher Report, ESPN, right out of school. When I was working at The Hustle that was the first time that I either wasn't a kid in college, or working in sports media. It was the first time I realized that it's kind of hard to follow sports if you don't have the time to do it, or you're not literally working in sports media.
And I remember I texted a bunch of my friends saying “Hey like, do you guys ever watch SportsCenter anymore?” And for the most part, and this is when we were in our mid twenties, everyone's like, “Nah, I don't have time for that.”
And I was like, “ What if I basically took what's in SportsCenter and put it in a newsletter and sent it to you in the morning? You could read it on the way to work.” And all my friends were like, “Oh, I'd, I'd check that out.” So that's quite literally how it started.
Turner Novak: That was literally the founding moment. Do you remember what triggered that idea in your mind?
Kendall Baker: It was me being, for first time in my life, not in the know about sports because I was writing the Hustle newsletter and covering tech startups. I was spending so much of my time in that world and I love sports, so for the first time in my life I was out of the loop. So as many people say, I created a solution to a problem I was experiencing and it turned out a lot of people felt the same way
Turner Novak: Interesting. Okay, so maybe we rewind just slightly. You were working at Bleacher Report and ESPN – did you learn about the media business there or have any interesting insights those couple years?
Kendall Baker: Certainly. Bleacher Report was my first job out of school, so while I was writing, I was also just doing whatever they needed, like helping with graphics.
Bleacher Report is a sport and sports culture media platform that was acquired by Turner Broadcasting System in August 2012 for $175 million. Source.
Turner Novak: How did you get that job at Bleacher Report? Because that seems like a college kid who love sports’ dream first job.
Kendall Baker: The job I took right out of college at Bleacher Report was almost unpaid. It was very low and it was a job that came with a program to learn how to become a sports writer. So I wasn't just writing, I was being taught.
Turner Novak: Wasn't Bleacher Report’s model sort of this like distributed network of sort of college students?
Kendall Baker: Certainly, at the early stages. So I came there in 2013 when I graduated from Penn. It was a very interesting time where Bleacher Report had just been acquired by Turner. And so Bleacher Report was in this place where they were still kind of this glorified blog with a lot of unpaid contributors, but they were also now hiring Howard Beck, Kevin Ding, like these known sports writers.
They were kind of in the middle of blog and legit sports media publication, which they've become more and more of, and obviously they're very linked with like Turner and things like that. They were kind of balancing the two things.
But on the point of my first job out of college, one thing I talk to kids in college a lot is about how to work in sports. I've found this to be true when I talk to other people, other of my colleagues and people in sports that have been doing this for a while – I think working in sports, whether it's sports media or anything in sports, is one of those things that, for whatever reason, you almost at the time feel like you’re not taking you career seriously, because everybody wants to work in sports, right?
I went through this thing where I thought, “Am I just doing this because it’s cool, or am I just doing this because it sounds fun?”. It fe;t like it couldn't be a serious career because everybody wants to work in sports. I had to go through this whole thing where I had to convince myself that I like this much more than the average person and there's serious careers to be had in here. It’s this weird thing. I'm sure there's other examples, but sports, for whatever reason, it just feels not serious enough.
Turner Novak: Yeah, that's true. The episode we published right before this one was with Dan Porter at Overtime, and we talk about how a lot of people don't even realize there's a business behind sports. And if you take it another step up, the business of sports has basically held the cable bundle together while it collapses alongside the internet – it's so important. It's so powerful.
Kendall Baker: Here's another thing I'll say to that, and I know Dan agrees because I'm sure we both talk to a lot of people. Kids in college will come to me and say “I want to work in sports.” My answer all the time is like, “Well, that's not a job because people think that sports is a career, but I think sports is actually just an umbrella under which there are many careers.”
So like, you want to work in sports? Well, my answer usually is, “So do you want to be a writer? Do you want to sell tickets?”. Sports is not a skill. And I think sports are so interesting and people are so into sports that they just say, “I want to work in sports.” But that's not actually helpful, right?
Because what do you want to do? You could be in sales, you want to be in marketing, do you want to do a podcast, you know? “Sports” is not a career. and I think people get that confused a lot because again, it's what they're passionate about and then they're like, that's what I want to do. But you gotta narrow it down, like.
What skills do you want to develop? What do you want to do? And then try and apply that within the world of sports.
Turner Novak: So then after Bleacher Report were you thinking, “I want to stick in sports?” Like is that how the ESPN thing came about? How did that job switch happen?
Kendall Baker: Yeah, no, I definitely wanted to stay in sports and so I ended up going to ESPN, which was a dream of mine forever. I went to ESPN and started working in production. I was basically working on TV.
I was in a rotational program there, which is really cool. We got to do a bunch of different jobs. I did everything from deciding the top 10 plays of the day to cutting highlights for games as they happen to literally running the teleprompter with my hand.
Turner Novak: Okay. Wait, so you have to turn the thing that they're reading?
Kendall Baker: A little dial, you keep up with their pacing and as you work with certain anchors more, you start to learn.
Turner Novak: Is this live?
Kendall Baker: Yeah. So I think we had probably a week worth of training where you shadow somebody. You have your headset on, you got the producer in your ear, you're kind of following the show.
And obviously there's certain segments where they don't need the teleprompter, but many of them do. It's when they're looking directly at the camera or doing some sort of thing they've written.
But the first day that I had to do that by myself is the most nervous I've ever been in my entire life. I was just so nervous that I was going to click the wrong screen, and I thought that if you mess that up and Scott Van Pelt is like on live TV, and all of a sudden like it goes dark or you're past where he's trying to read. Your mistake is going to be very visible and then they're going to be pissed.
So I was just so nervous. Thankfully I didn't have any big screw-ups but that was a really cool job. I worked a lot on SportsCenter, this show that I grew up obsessing over, and all of a sudden I'm now kind of part of it and seeing how it's made.
I probably shouldn't admit this, but whatever. In the ESPN studio, there's like glass behind where the anchor desk is and you can kind of see where I, as the production assistant and a few other people, sit in the back.
One of the first shows that I was working on, I texted my friends, I was like, “Watch Sports Center tonight. I'm going to raise my hand in the back. And so if you watch Sports Center you can see me!”. That was the coolest part about the ESPN experience for me. Getting to see how the sausage was made.
The other big thing that happened at ESPN for me was that it was the first time I worked somewhere surrounded by fellow kind of sports-obsessed people. But I was told by numerous people there that I was more obsessed with sports than any of them. It was being told “You really love this stuff,” from someone who loves it just as much.
And I think hearing that confirmed to me that I was making the right career decision and it also gave me confidence. It felt like I was given the green light to like go as far as I wanted in this world because I was clearly very passionate about it. And not just on par with the other people but they were like, “Dude, like you're like crazy a little bit.”
Turner Novak: I've had some of those moments too where someone that you maybe really respect or look up to tells you that you should actually really pursue this more. Or you're, you're good at it. I don't want to say it's an ego boost. I don't know if that's the right word, but it's a confidence boost.
Kendall Baker: It just kind of confirms to you that you're in the right field, I think, and again, going back to my point about people who want to pursue sports, I think it's one of those things you assume well, everybody loves sports. Everybody's obsessed with sports, right? Or at least you know of people who are sports fans.
We all love sports…but if somebody's like, “Well, yeah, but you are even more into it.” It's just something that was really important for me to hear early on. That stopped any questioning in my mind. I wanted to work in sports.
Turner Novak: And then you left sports. Why did you do that?
Kendall Baker: My friend was working at The Skimm at this time and I got this idea of “What if I did sports newsletter?” in my mind. That sparked an interest in me in like “How do you start a media company?”
Turner Novak: Was this when you were still at Bleacher Report? I'm trying to remember timelines.
Kendall Baker: This was early ESPN. So like the end of 2013. I was at Bleacher Teport for a pretty short amount of time. So it just planted this idea in my head that I would love to start a newsletter, or just like a media company, but I had no idea how to do any of that.
I grew up in New Jersey, went to school in Philly, and I was living in Connecticut. Starting a business was in my head and also like, I wanted to get out of here. I wanted to live somewhere else. My brother-in-law was from San Francisco. He's like, “You'd love San Francisco, everything was like startups.” The West Coast. I thought I should go to San Francisco and I should work at a startup and I should ;earn media.
I obviously thought about sports media. I would ideally have loved to stay in sports media to do this, but I ended up finding The Hustle, which was not sports at all, but it was very much a startup, like I said, I think three, four employees maybe. And I really liked their voice and kind of what they were doing.
I took that job primarily to learn the media business still with the idea of wanting to start a sports media company at some time. So I got out of sports media, but I stayed in media, and I think you can learn the media business regardless of the content.
Turner Novak: What’s the difference between sports media and let's say like finance, politics, technology, media? Like are there differences or are they all pretty much the same?
Kendall Baker: The core model of any media company is relatively the same. I think I'd say if you're comparing it to finance, for example, sports is still much more in the entertainment side of things versus finance where a lot of the readers are professionals…
Turner Novak: I don't know. I'm going to disagree. I feel like a lot of the finance, at least the mass market finance content…
Kendall Baker: I think somebody who covers finance has a much better chance of getting people to pay for their content. Let's say they do a newsletter and they charge 10 bucks a month. If their value prop to that reader is, you're going to pay me money, but you're going to make more money because you're going to take what I tell you…
Turner Novak: Yeah, that's fair.
Kendall Baker: I'm covering sports, so unless I'm covering sports betting, and my value prop is I'm going to give you picks and you're going to go make, like, I'm not promising you some return on your investment essentially.
I think ultimately a lot of sports news at the end of the day is just headlines and entertainment. There's nothing wrong with that, but I just think that sports traditionally, and part of the reason why I launched my newsletter was like, nobody's doing this.
I think part of the reason why you haven't seen the same innovation in sports newsletters happen that you have in finance or politics, is that people just assume that sports fans are not in their inbox. Whereas, you know, finance or business news people are like, “Oh, they're going to read at work because it's helping them get better at their job.” Sports still exists in this entertainment space for the most part.
Turner Novak: And sports is probably one of the broadest forms of entertainment. You know the TV bundle is kind of eroding, but if you just look at what are the most watched TV events or entertainment events, it's mostly the NFL and then there's like a little bit of NBA and maybe like one tennis grand slam and like the World Cup. And that's basically like the top.
Kendall Baker: I'm sure a lot of people have seen these stats, and I might be getting this slightly wrong, but I think last year of the 100 most watched TV broadcasts, 87 were sports. And I also think what's interesting about sports is that it's the most naturally verticalized media sphere, if you will.
In sports, you have sports at large, but then you have The NFL or football, college football. You have all these leagues, all these sports that have specific fans. Some people just like the NFL. Some people just like college football, some people only like soccer, and so there's media spheres for all of these sports.
If somebody was starting a sports media company, and let's say you wanted to lean into newsletters, it's already verticalized for you. You launch a newsletter with everything and then you have an NFL newsletter, NBA newsletter, major league baseball. So, there are very natural, sub-verticals within sports.
Turner Novak: Which is also how you make more money as a newsletter, right? You bundle and you can sell ads or subscriptions. Have writers that cover different ones that are kind of like all sharing costs and generating revenue over different, and you maybe have a subscriber that instead of just subscribing to one, they subscribe to the main, but also golf and football.
Kendall Baker: Exactly you want to get on like 2 or 3, is the sweet spot. I don't remember the exact number at Axios, but there was some number where once people start subscribing to too many of our newsletters, they actually become less engaged.
Turner Novak: Oh, really?
Kendall Baker: Yeah, well I think it makes sense, right? If, if you're getting like too much, you kind of tune out. I think there's a sweet spot.
The other thing I'd say about sports media that's unique is that there’s two major ways in which people follow sports, in my mind. One is nationally. So that's, stories of the day in the same way is true for politics or anything else. The big news that everyone's talking about around the water cooler kind of thing, and that's largely what I cover.
But there's also this whole other side of sports, which is fans, specific team fandoms. So, the way somebody follows sports news nationally is much more as like a reality show. They're following the same way you follow politics. Just like what's the news of the day? Whereas if you're like, “I'm a huge die-hard Orioles fan,” the way I follow the Orioles is completely different. The way I follow Orioles is almost more like a cult.
Turner Novak: Yeah.
Kendall Baker: There’s two very distinct ways to get to sports fans. One is nationally. You look at some place like The Athletic, which does plenty of national stuff, but their big value prop is that you are obsessed with the Yankees. And we (The Athletic) are in the clubhouse – we got reporters on the ground, we got beat reporters on the ground. We're going to give you a thousand words on your seventh reliever because we know his whole life story.
Your average sports fan, I'd say is interested in nationally, the headlines. They talk with their friends, aware of what's going on. But then they have these teams that they're diehard fans of that they follow in a completely different way. That people would think would be, is like crazy sometimes, you know, like I said, you're like a cult member.
Turner Novak: So would there be a third, or maybe this is a part of the cult, that’s just regional sports? Like I'm in Detroit, or you know, I'm in Ann Arbor, which is close to Detroit so I like the Red Wings hockey. I like the Lions football. Pistons basketball. Is that kind of a third or is that just the cult?
Kendall Baker: I would tie that into the latter, and maybe less of a cult. But you're right, like there's a regional sense. I guess a better way to describe it would be there's, two ways people follow sports. One is as a news consumer, and one is as a fan.
You could be interested in what LeBron James is doing, but that doesn't mean you're a Lakers fan, whereas you are super interested in what happened in the Red Wings game last night because you're from there. But if you lived in, let's say, Florida, you couldn’t care less probably.
Turner Novak: Yeah, and it's interesting too, with the internet, you start to realize, “Wow, the Lions suck. I should cheer for other football teams.”
Kendall Baker: Yeah. It's been rough for the Lions, but they're on the come-up. My stock’s in alliance.
Turner Novak: Really? Because the way I kind of think about it, I play a lot of fantasy football, so I think about what are the most undervalued teams? I was thinking this going into the playoffs, and this might have changed because they sort of did well with the Jaguars, I was like, “Oh, they're going to be really good next year.” I think Trevor Lawrence could be a top five QB, which is kind of insane to say, but that's how you win in fantasy football.
Kendall Baker: That's how you win fantasy football. And now increasingly that's how you win betting. I mean, that's what's really interesting about the rise of betting and fantasy football, which has been happening for a while, is that people can now treat sports more transactionally.
Especially among young fans, you're already doing all this research. The analytics are much more approachable now in ways they didn't used to be. And you have a lot of fans now like, “I know more about you and I'm going to actually like act on that.”
Even buying baseball cards is back. If you think Trevor Lawrence, for example, is going to be a top five quarterback, buy his card, right?
Turner Novak: I also am regretting saying that because he's probably going to have a terrible year.
Kendall Baker: I think it'll be good. But, but I'll warn you there's so much parity in the NFL, especially compared to some other leagues. Let's say the NBA – you can kind of see a good team building slowly, whereas the NFL, it changes from one year to the next.
The Lions last year were a good example, they were irrelevant. And then last year out of kind of nowhere, they’re very good. That happens a lot in the NFL, much more than other sports.
Turner Novak: Yeah, I haven't actually looked. I'm thinking anecdotally, the Lions lost a lot of really close games if I'm remembering. I went to the game where they played the Seahawks. It was like 50 to 47 or something. Just every drive was like a 60 yard run or touchdown or whatever.
It was fun to watch. It's also infuriating because they just kept getting scored on. Their offense was very good. I think they had one of the most efficient offenses last year.
Kendall Baker: Dan Campbell is the man.
Turner Novak: Is he? I don't know, you obviously follow much closer than I do.
Kendall Baker: Dan Campbell is like, you know, people use the word “football guy” to describe people when they're every stereotype you could attach to football. Like, they're super intense. They're like doing pushups, you know, like that. That is, that's like Dan Campbell to a tee. He's like the biggest football guy of all time.
Turner Novak: Well, I think what the Lions always had was discipline, work ethic type problems, where I don't know whether it's missing curfew, or if it's just not trying in practice or something, but…
Kendall Baker: It was a culture problem. I think a lot of teams, the Lions, for example, their roster now compared to five years ago, or 10 years ago, is obviously completely different players. Everything's completely different. But there are still cultures that develop around franchises.
You look at the Miami Heat as a good example in the NBA. Their roster right now, there's not a single player other than Udonis Haslem, who was also on the team when LeBron and the big three were there. So it's not a case of the people there, but the culture of the Miami Heat stayed consistent.
And that's because they have certain things they just drill into you. They are known to practice harder than other teams. There are cultures that get built within franchises, even though the players themselves, come in and out.
Turner Novak: Interesting. And I mean, I know we have a lot of kind of founders of companies that listen to this. It's probably like a from-the-top kind of a thing.
Okay, so we really got sidetracked there. So you had this idea for a daily sports newsletter, moved to San Francisco, and got the job at The Hustle. You kind of talked about this, you pitched the idea of doing it. How did that go? How did you convince them it wasn't the model idea?
Kendall Baker: What we did basically was launched it as a project. We kept doing what we're doing and then we kind of launched this newsletter on the side and got a thousand people to sign up. I think we published it for like a month. and the feedback we got over that month was so profoundly positive that really convinced everybody to pivot to that as our business model.
And like I said, The Hustle, which now a lot more people know – five people working there. We were, in this room in an apartment. Pivoting the business, while certainly risky in some respects, it wasn't like this huge undertaking. It was like, all right, instead of writing blogs, we're just going to put our stuff in this newsletter and send it, and then we'll figure out how to monetize it and do all that stuff.
Turner Novak: Okay, so then how do you write a daily newsletter? Because I write a newsletter slowly throughout the week. It sounds like a lot of work.
Kendall Baker: It's a lot of work! Obviously most daily newsletters are news-centric, right? So you're kind of, at the mercy of the news cycle. And sports is impossible because my colleagues who write about the markets, for example, well the market eventually closes and they can have a normal life.
Whereas I, as much as I'd love for the newsletter to be done at 7:00 PM, sports haven't even started yet.
Turner Novak: Yeah.
Kendall Baker: I'll say this. Writing a daily newsletter and anybody who's done so can attest to this, is very much of a lifestyle. People ask me all the time, how many hours does it take you to write this? I have no clue because I don't have a normal work routine.
It's very much like, yes, I have certain stories that are evergreen enough that I can write days in advance and get those done and have them ready to go. But so much of what I'm doing is responding, reacting to the news that if something happens at 10:00 PM, I kind of have to be on.
Now the nice part about that is that I'm not expected to break that story right away so if something happens at 10:00 PM I don't have to like get a story up immediately. I can get it done for tomorrow morning. But I guess I'd say about the rough daily workflow of a daily newsletter is having a really good system to follow the news. So I've built this, and I've shared this many times, on Twitter and things, my RSS feed.
RSS is obviously very old technology, but I've built this RSS feed that is invaluable to what I do. It has every source that I would ever read. Twitter, has now pulled the API, so I can't do that anymore but I had all my favorite Twitter accounts. I have subreddits, newsletters, like every source of information that I could possibly need I have in one feed. That allows me to constantly stay on top of what's going on.
It's honestly like if I miss a story, it's on me. It's not because I happened to not see it. It's there! I just have to scroll through. It's almost like if you think about it as an email inbox, if every sports story of the day comes into your email, it makes it very easy for you to make sure you don't miss anything, I rely on that very heavily, I’m refreshing that throughout the day.
Turner Novak: What's the product name?
Kendall Baker: Reeder. There’s some others that do fairly similar things, but this is synced across all my devices. You can read all the articles within there. It actually allows you to link your pocket as well, or any other like tool you use to save stuff.
So I can't tell you how like intuitive and easy the system that I've created for me is, where I'm reading stories throughout the day and anything that's interesting, I immediately pocket it. And then when I go into write later, it's all saved right there. I tell people I can read the internet in a way that I control the spigot and I'm never overwhelmed.
A lot of my routine is just kind of staying up to date and constantly, seeing stories and pulling those off to the side and kind of saving them or immediately writing about them feeling out the news of the day and then deciding how to take all of that and organize it and give it to my readers in a way that's very easy for them to digest.
Turner Novak: Interesting. Okay, so what was the point then when you decided I've learned enough about newsletters, I'm going to do my own thing.
Kendall Baker: It was a little over a year after The Hustle and it was when I had that realization, I still had that idea of sports in the back of my head. The idea that I wanted to do a sports newsletter, that idea never left.
But when I actually found myself personally realizing I could use that product, because I all of a sudden wasn't following news the way I could, I was like, I gotta do this, and the process of writing a new sports newsletter is going to get me back into sports, which I miss. Everything was like pointing me in this direction and it was almostincumbent upon me to do it.
Turner Novak: Yeah. So how did you, how did you start it? Like how do you start a newsletter? We all see people starting them now on Twitter or LinkedIn. What was the process of starting one back in 2016, 2017 when you did it?
Kendall Baker: So the process was certainly not what it is now because the tools that exist now just weren't there. I used MailChimp. The one thing I did, which I would still recommend anybody launching a newsletter do, is that I was very open to trying different formats.
My goal was to write a daily sports newsletter, and I had this idea of like, SportsCenter in an email in my head, but what does that mean? What does that look like? How many items is it? I didn't want to just assume that I knew best.
In the first month and a half of Sports Internet, I probably sent 12 to 15 different formats. I just experimented. There's many different ways to cover the news of the day format-wise.
And so I kind of threw everything out there and got feedback from people. Also just using personal feedback of like, “How was that? Was that easier? Was that harder to do?”. That was definitely a big part of launching. It was quite literally just trying a bunch of stuff publicly. And then adjusting it and tweaking it, and finally kind of arriving at a format that I felt people liked and I also felt was repeatable enough for me that, I could see myself doing that over and over and over and over.
It was about finding this balance of like a rubric to some extent, but also enough freedom still to not feel like I'm just like plugging in information into this rubric. I think that's a big part of designing a daily newsletter for people is finding the balance of giving yourself this framework so that when you're reading the news are like, “Ooh, that would be perfect for this section,” but also not pigeonholing yourself, where if something happens, you're like, “Well, I don't have a section for this”. You have to have enough freedom to, not be a slave to your own format.
Turner Novak: Yeah, because I'm trying to remember. What you really ended up hitting on was you had like 10 sections basically, or it was maybe a different number?
Kendall Baker: And funnily enough, I was inspired by Axios, who later acquired the newsletter. Part of my thinking there, again, inspired by them, was there's something really nice for a reader, especially when they're on the phone and they can't see much above or below what they're reading – if it's numbered, they have a sense of where they are in it.
There's something kind of like, comforting about like, “Oh, I'm on five, there's five left to go.” It gives a sense of place. And these are the kind of like detailed things that I obsessed over for so long.
Ultimately with Axios, we literally said at the top of every newsletter, this newsletter is five minutes, this is how many words it is, this is how long it's going to take. I think it's just a small thing, but a big thing for a reader to kind of feel like they know what's coming.
Turner Novak: So then how did you get people to start reading? You kind of talked about how it's easier now than it was back then. I'm trying to think of how I found it. I think it was an ad in another newsletter. Did you ever do anything with market snacks from Robinhood? I think that's probably where I found it. Hopefully that was early.
Kendall Baker: It was early. So, the main way to grow back then, I mean outside of paid acquisition, was simply doing cross-promotions with other newsletters. And as crazy as it sounds now, this was what, five years ago? There weren't that many.
Turner Novak: Really? Okay.
Kendall Baker: There weren't that many. It was like MarketSnacks, because I got introduced to those guys and they had a bigger following than me, we worked out like, “I'll shout you out, you know, for a week…you gimme a shout out tomorrow.”
I did the same thing with Morning Brew. I'll give you guys a shout out for like a month that you give me one shout. We were kind of figuring out, “How is this a fair trade off?”. That was really effective.
A big learning experience that I had early on, and this is kind of connected to that, was doing a few cross-promotions with sports-related Instagram pages, or other content featuring sports, but it wasn't a newsletter. And I did cross-promotions with Morning Brew and MarketSnacks, where the content was not sports, but it was a newsletter. And the latter was so much more effective.
And my conclusion was that “newsletter reader” was a demographic, I tell people all the time, somebody who reads newsletters already, if you think about it, it's like they already get the newspaper, right? The newspaper already comes to their driveway every morning and by saying “Hey, would you like to read my newsletter?” all you're asking them is “Would you like to add another section to that newspaper you already get in the morning? Would you like to add a sports page? You already get the newspaper. Would you like to add a sports page?”. “Oh, that, sure, I'll try that out.”
Whereas if you find a sports fan on an Instagram page and you say, “Hey, I have a sports newsletter,” even if they love sports, you're still asking them to subscribe to the newspaper, which is a much bigger leap.
They're like, well, I don't get the newspaper and I don't know if I have the time to read. So that was a really big learning early on. Regardless of what the content is, if somebody reads a newsletter, there's a decent chance that they'll try yours out.
Turner Novak: I think there's demographics too, like even Instagram versus Twitter. Twitter is very tech-based, so you know, those people probably are more into reading versus the Instagram audience. They might not even have Twitter or the email app on their phone.
Kendall Baker: It's very true. And I think maybe becoming less true because newsletters are much more ubiquitous, but especially back then, if somebody doesn't read newsletters already, trying to convince them to sign up for one, they're like, “I don't even use my email, man.” It’s just kind of a foreign idea.
Turner Novak: It's an interesting thing we're coming up to now. I've heard some murmurs or seen stats about Gen Z in email. They don't check them. You gotta hit them on Snapchat or something. Or like TikTok.
Kendall Baker: It's so interesting to me with email. I think we can all agree that it's a very effective medium for newsletters. I’ve been a parent for a while and continues to become more and more apparent. Every time somebody says email's dead it’s actually better than ever.
However, I think we can also all agree that there are limitations to it, and young people are a perfect example. Most high schoolers do not use their email, let alone have one. Even in college you get an email, which is great, but do you really check it? I mean, I didn't use my email much in college.
There is a certain downside to getting young people to read newsletters. It’s tough. However, the thing that I always tell people is that I believe in email as a medium and newsletters as a medium.
But if Apple made it possible to send rich text messages, so if I could essentially send my newsletter to you via text and let's say you get a message from me and you hold your thumb down and it opens the whole newsletter – basically if there was a way for me to give you the same experience you get from me via email, but in a text message, I would do that.
Email is the perfect way to do this right now, and that's why email is never going to die. But if you could keep the same benefits of email in a place that more people use, younger people use, it's very interesting, like this push and pull of email.
If something comes to replace it, I’d jump there immediately. You know what I mean?
Turner Novak: I would bet you, I don't know what the time is, I don’t know if I want to say 5 or 10 years, but I do think that's going to happen. If you kind of look at what Apple's been doing, they've been starting to build out this advertising network. When you think about how they've made it harder for Facebook to track ads, they're planting all the seeds.
And again, we're going to get into this a little bit later with our content business. You monetize content with advertising, and I think iMessage is one of those sleeping kind of content products. iMessage could have been what Snapchat is, and there's a lot that they can do with it. It'll be interesting to see.
I would bet within the next 5 or 10 years you'll be able to do something. I've seen a couple newsletters experiment with text.
Kendall Baker: I experimented with text as well. I think there's a certain balance of email, especially on a daily email. If I get a daily text, I think I would like within a month be like, “Alright, stop texting.” There’s a balance to be struck there. With email you can still get to people, but they can kind of tune it out a little bit more.
But the bottom line is, and this is how I think about newsletters, is that newsletters, just like texts, just like DMs on Instagram, Twitter, whatever. It's all messaging, and that's really what's effective. What's effective is messaging. What's effective is you're coming to them. They don't have to find you, they don't have to seek you out. You're coming to them at a consistent time, and you're coming to them in an app that they check all the time.
If I send you my newsletter, it pops up on the top of your phone the same way if I texted you. The only difference is when you click it, you're opening a different app.
Turner Novak: It's probably too that you get a rich HTML format in email versus on text, it’s just, you know, text. But then also it's cross-platform where you could be on your phone or on your computer versus Instagram – no one checks that on their computer.
Kendall Baker: You know even Substack did this, which I thought was a mistake, but there's also benefits to it, so I get it, For the last six years, there've been so many attempts by people to say, “Oh, people are really into newsletters, but it's not the ideal experience to read those newsletters in the same inbox that you have all these other emails and stuff and promotions. Maybe we should just create a separate app just for newsletters…”
I totally understand, but what you're missing there is the biggest benefit of newsletters, which is that it is in your inbox; it’s one of four apps that everybody checks all the time. The chances of you getting me to start habitually opening a new app? I mean, I can't tell you the last time I adopted a new app. Maybe Threads.
&ou know how hard it is to get somebody to add a new app to their routine? Everybody checks email. If you look at everybody's screentime, like email's probably at the top of every working professional's list of apps.
Turner Novak: Are you actually using Threads too, by the way?
Kendall Baker: Not really. I'm starting to.
Turner Novak: Interesting. Okay. My assumption was, I’ll use it, but the content sucks. It's just Instagram, but text. But Facebook will get us to use it.
Kendall Baker: Of course. And what's funny for me is, and I think this is probably true for a lot of journalists or people who write and have an audience for a living, is that for so long Twitter for me was like, that’s where I am that person. And then my Instagram followers are like my friends from high school. It’s just a completely different audience.
The only way for Threads to make sense for me is if I get enough of that audience that I have over here to move over. That's easier said than done.
Turner Novak: So what was the business model then when you started Sports Internet and kind of as you scaled up? Was it sponsors?
Kendall Baker: Sponsors. It was just me, and selling sponsors was hard and I was just stretched so thin that ideally I would've had different daily sponsors, or at least weekly. But I ended up signing longer term deals for less money. But just to make it easier for me, just do like a month of advertising.
Turner Novak: Yeah.
Kendall Baker: I actually have the first check right here.
Turner Novak: Amazing! Can we see it?
Kendall Baker: Yeah I kept it. Well it's under the table, so it'd be hard to see,
Turner Novak: Oh, got it Okay.
Kendall Baker: My first deal was with FanDuel.
Turner Novak: Oh, interesting. That's a good one.
Kendall Baker: It was a result of a bunch of people from FanDuel reading it. I kind of solicited ads and they got back to me and it made a lot of sense. That was my first advertiser and it was like a month-long deal and I think it was, it wasn't much.
Again, it was just very early. I probably had like 5,000 subscribers and I think probably if I had to guess… it was $2,000 actually, so this I think was for two weeks. Yeah, $2,000.
Turner Novak: For two weeks? Okay. So 10 emails for 2,000 bucks. So 200 bucks an email on 5,000 subs?
Kendall Baker: Yeah, and for me at that point, FanDuel was a big enough name that for me, that advertising deal was more like legitimizing what I was doing. I think there was something to be said for having sponsored by FanDuel in very early on, as a solo person doing a newsletter that kind of gave it a sense of like legitimacy.
And I think that, you know, that's true for a lot of early advertisers. Like there's benefits beyond just the revenue. Obviously the revenue's most important, but there's certain companies that are known enough that immediately make their ears perk up. Like, “Oh, this person's legit,” you know?
Turner Novak: There’s social proof, you see that all over the place. Like, “Hey, you should read my newsletter because LeBron James subscribed to my newsletter. FanDuel's a sponsor. We've broken this story about a trade.” All those things make people go “Holy shit! Like this is real, this is a legit newsletter.”
So then how did you kind of evolve that over time? Like were you ever in a spot where you're like, “I'm okay.” Or was it the whole time you're just like, “I need to figure out how to make money, I gotta get this new issue out.” Were you getting any sleep? What did your days look like then when you were writing this thing?
Kendall Baker: I was not getting much sleep. It continued to be ad-backed. I developed a secondary ad where I created this game called the Gauntlet, where it was essentially like a pick-em. So I'd have a question at the bottom of the newsletter starting on Monday asking like, “Will Bryce Harper had a home run tonight? Yes or no?” And, I would see who clicked yes, who clicked no, and then depending on what happened, if you got it right, you'd move on and if you got it wrong you’d get eliminated.
Turner Novak: How did you do that? I think I remember that.
Kendall Baker: The reason why I didn't keep doing it was because it literally made my life so hard, because I had to go see who clicked yes, go see who clicked no, and then I would create the newsletter the next day, but I would have to create two versions – one to send to the cohort that said yes, and one to the cohort says no.
And I had to keep doing this every day until I got to Friday. I thought it was so cool, but I couldn't keep doing it. But I did have that sponsor and the sponsorship was like, depending on how you did, the higher the discount you got.
It was with a company called Wolaco, which makes athletic clothing. And if you got all the way to the end of the gauntlet, you got 25% off. If you got just one right, you got 10% off. So I tried to gamify the ads. I thought it was awesome and I’d love to bring it back if I could automate it or just have somebody doing it that's not me, but that was kind of how I was monetizing it.
I didn't think I was going to make it profitable just by myself. My goal when I set out and launched it was definitely to hit a certain milestone, which in my mind was 25,000 subscribers.
And then I was going to go raise money and hire people and build out a whole business. So, that was my goal; hit 25,000 subscribers, and obviously before that could happen, I ended up selling it to Axios, which we can get into.
Turner Novak: What is that like getting acquired?
Kendall Baker: Well, it was interesting. It's getting acquired as one person with one newsletter, so it’s very different than acquiring a business with a lot more assets or a lot more employees. It was really more of an acquihire.
The one thing that I think really worked in my favor was that I made a very intentional decision early on, because I figured this could maybe happen – I never spent a single dollar on paid acquisition.
What I think that allowed me to do is tell more of a story when I was getting acquired as opposed to if I had spent money acquiring emails then I would have had a maybe bigger list as a result of that, but then my open rate would be then lower because I’d be getting subscribers in a less organic way.
I think the negotiation with Axios would've been more of a math equation. It would've been more like, “Hey, you have 17,000 subscribers, each subscriber we value at this amount of money, and therefore this is how much we're going to buy you for.” Whereas I was able to say to them, let's forget the number of subscribers.
My open rate is 63%, which it was, and so the story I was able to tell, which I think a lot of business and acquisitions rely on asking “What's the narrative? What story are you telling?”.
My story was, you're not buying 17,000 emails, you're buying a community of people who are obsessed with this product, who, when I don't send it out for a week, which happened one time because I was on vacation and I didn't communicate it well enough, will freak out.
And two-thirds of them open every single edition. That allowed me, I think, to tell a completely different story, and I think it helped me get a higher multiple for it in the negotiation, quite frankly.
Turner Novak: Did they acquire the email list?
Kendall Baker: Yep. So they acquired the email list, so it was an acquihire, so they basically acquired my email list, as a separate transaction, and then they hired me to come over and continue doing it. The reason why I ended up going there, well there are many reasons, one being I just thought it was a great fit.
Like I said, they had inspired my format. They really were newsletter first in a way that few media companies were and still are. I felt they really understood newsletters. They spoke newsletter, if you will.
Also, I was so broke and so burned out. And I think one realization I had, and this happened less than a year after I started it, was that as entrepreneurial as I am and as much as I want to build a business and run a business, I was having so much more fun writing the content, and what Axios or any company at that time was basically offering me was “Let's let you do that and we'll do all this other stuff.”
Turner Novak: Because they probably helped you sell ads, right? I'm assuming you didn't have to think about that anymore.
Kendall Baker: Exactly. Just the fact that I'd never have to think about that again, at least in that role. I just felt like I was doing so much and then trying to pour myself into this content, but just the idea of “What could I do if that was my sole focus? I feel like this is really working. I feel like people are really liking this, but I also feel like I'm just scratching the surface on what I'm putting into it, because I just only have so much time.” It just felt like the right move.
Turner Novak: Okay, so two questions. What is a good open rate and click through rate just for other people interested in newsletters? And then how do you sell sponsorships for a newsletter?
Kendall Baker: So a good open rate is up for debate. I mean the industry average, I believe, is like 17%.
Turner Novak: So is this like news newsletters?
Kendall Baker: That's why it's kind of misleading because I think so many kind of email marketing and newsletters fall into the same bucket. Email marketing is a lot just spam…it’s crap. Whereas a lot of newsletters are editorial media products – a totally different thing, all under the same umbrella.
That's probably a misleading number. I mean, I would say the average of newsletters is probably like 30%. Maybe. That might even be high. There's a lot of bad newsletters out there, just like there's a lot of bad podcasts and everything out there. I think I would say if you're over 40%, you're doing a good job.
Turner Novak: That's good news for me. I'm higher than that. Not that much higher. I'm not 63.
Kendall Baker: Yeah, 63 was unheard of.
Turner Novak: Yeah, that's actually insane. I think the highest I've ever seen is 77%, but it was like a 3,000 person list or something. Super niche and curated.
Kendall Baker: Mine was, I think the exact numbers were 63.2% open rate and I had almost 18,000 subscribers. I could have had a lot more subscribers, but I cleaned the list quite frequently.
Every few weeks I'd see if a particular person hadn't opened, sometimes I'd email them saying “Hey, do you want this?” and you know, maybe it was going to their spam or something and they didn't realize it.
It was very manual and took a lot of time and maybe it wasn't worth it, but I think ultimately it was worth it to really focus on the open rate because going back to what I said, like telling that story. If I had 25,000 subscribers and a 55%, 50% open rate versus 18,000 and 63%, I think that tells a very different thing.
Ultimately, is 8,000 emails going to be that much more valuable that you're not able to tell that story? It’s not. I'd say anything over 40% is very good.
Turner Novak: And so for somebody who's not familiar with newsletters or like how the business works, open rate is important because why?
Kendall Baker: You’re essentially telling advertisers, “This is how many people you can expect to see this.” It’s also a great measure of just general engagement.
If you have a million subscribers, 20% open rate, it's like, all right, you have a lot of people who are signed up for this thing, but not that many people really care, right? Whereas if you have 400,000 subscribers and 50% open rate, it's the same number of people seeing it, and it's way more engagement.
So to your question of how do you sell ads and what information do advertisers want? Generally speaking, there are two types of ads being sold in newsletters these days.
One would be a brand awareness campaign. So that's simply, “Hey, we want to be attached to your content. We think you're doing a great job. you know, your audience would like what we're doing.” And really what they're paying for is just a spot in the newsletter.
Often they'll have some sort of click-through, like they want people to go to their site or to buy something. But the deal itself is not structured around clicks at all. It's just, “We're paying you this money for this done deal.” And then you obviously have to report back how many people opened it to them.
But then there's also, deals that are structured around, clicks.
Turner Novak: Performance-based, or something?
Kendall Baker: Performance ads, exactly. We call them performance ads. That’s usually DTC companies or companies with products and they want to sell a specific thing and you're getting paid out.
Usually you'll structure it with a flat fee up front, but then that fee's relatively lower and then you're getting paid based on either just a straight number of clicks or number of people who actually purchased.
Just any sort of kind of affiliate deal, it's pretty straightforward. If you send a hundred people to buy shoes and 80 of them buy the shoe, then they're going to give you a cut of each of those sales essentially.
Turner Novak: When you start to kind of think through some of these numbers, a fairly large news newsletter list can be a pretty lucrative business where you write one email, 300,000 people open and read it. Then you drove, let's say 500 people to buy a product and you're getting paid, you know, 10 bucks per purchase that you drove or per click. You wrote one email and you made $10,000. The math on that makes for a pretty good businesses.
Kendall Baker: There are really good businesses. You can keep them really lean, and I think that's why you're seeing a lot of people start newsletters as one person or two person or three person companies is because if you run the numbers, if you do a good job, it's a profitable business pretty quickly.
And even if you compare it to podcasts, which I would put in a similar bucket of just lean business, cash-flow positive businesses – to start a newsletter is way cheaper than a podcast.
You don't have to buy any equipment. A good podcast microphone's a pretty good chunk of change. There's a lot of things you can do to improve sound. Most people nowadays are going to film the podcast too – there's a lot more to it. Whereas to start a newsletter you need a beehive, or a Substack, or some way to send those newsletters. You need a computer.
Turner Novak: Yeah, you could type from your phone. And Substack is free when you start, you don't have to pay.
Kendall Baker: When I was doing Sports Internet, which is what I sold to Axios, I think my monthly costs strictly related to the business, which, you know, ended up entailing some other things because I did have a website and I did have some other things, was probably like 200 bucks.
Turner Novak: Which as we talked about, what you made that from sending one email was about 200 bucks. Yeah. So they can have pretty good margins.
I think they get a little bit of a bad rep sometimes when people, especially venture investors, will say media companies are bad. To your point, you can't just blow it up super quick with the typical venture playbook.
Bloomberg is basically a media company that's vertically integrated selling people $28,000 a year subscriptions for like a special keyboard and like some data.
Kendall Baker: I mean, you look at some of the most successful newsletter companies and they did not have to raise much money, because you just quite frankly, don't need it. I think when the investment comes in, venture or otherwise, it’s usually when the newsletter has had some level of success, created some level of community, and there's obvious pathways to find more revenue streams for that community, whether it's events or whatever else.
The investment is based on the community you've built through the newsletter. And now it’s like, what else can we do?
Turner Novak: And so one of the companies I invested in personally is essentially like a newsletter holding company called Workweek. I don't know if you've seen them, but they've started launching some software products. So all their newsletters are B2B, and I think the first one that they've kind of announced publicly is a franchise newsletter.
I'm not going to get the number, but it's tens of thousands of basically franchise owners; people who own Burger Kings and McDonald's. And, there's thousands of these different restaurants and retail and landscaping businesses where you can, you know, essentially borrow the, brand name and open your own local version of it.
And so now what they're doing is they're launching software related to people who run franchises. So obviously they're monetizing with advertising, and usually what they'll do if you subscribe and read the newsletter, the ads in the newsletter are, “Hey, open like a Krispy Kreme franchise,” or “Open like a dog grooming franchise.” They’re very relevant in targeted ads, but then they're also like, “Hey, pay a hundred bucks a year, a month,” whatever the price is, “for the software to help you run your franchise better.”
I don't know what direction they'll go, but when you think about some of that math, it was like, okay, they might acquire a newsletter reader for $2, $3, $4 and they'll profitably serve them the advertising business. But then suddenly there's a software business that maybe makes thousands of dollars a year per customer and they acquire them for $2 in the newsletter.
Kendall Baker: And I think that you're exactly right. And I think that with that model, we're only at the tip of the iceberg of that, because it is true that, especially right now, the ad market's pretty soft. Any media company that's strictly ad backed and has no other sources of revenue is not a good idea.
I think with Workweek and what they're doing specifically to what you talked about, speaks to what I said before, which is that you can just build a really strong connection with people with a newsletter more so than even like a blog. Like you think about if their franchise guy was just writing all of the same content he's writing in that newsletter, but on a blog, plenty of people will still seek that blog out and end up reading the stuff. There's something about the fact that they're getting that consistently, and there's a relationship that's developed there that's just kind of hard to explain.
But then when it comes time you want to sell them more things it is just that you're able to create a community so much quicker and in such a more profound way through this newsletter. And it kind of seems simple, but it's true.
Turner Novak: And the newsletter is also a blog, like you can go read the newsletter online too.
Kendall Baker: So you know what? It's funny you say that. Like one thing I tell people all the time is to remember that before people started doing newsletters as they are now, you'd have a WordPress. You’d do a blog, and then on WordPress there was always the option to send this blog as an email as well.
And I feel like we've basically just flipped that. In this era where everybody's overwhelmed with stuff and you're typically opening your phone, going to a social media network and just scrolling aimlessly and there's no intention behind what you're doing, why would you put your content somewhere where people have to seek it out and then maybe they get it via email?
Why not just send it via email and then they can also choose to seek it out? In hindsight, it's like, so obvious that people would choose to write a newsletter that's also a blog now than have a blog that is also a newsletter.
Turner Novak: Yeah, and when I kind of think about what are, what are the apps or the properties, the digital properties that people go and seek out, it's usually some kind of aggregation product, whether it's Twitter, Reddit, Facebook, Instagram, even like Netflix is doing aggregation. Maybe games if you love Candy Crush, maybe that's an example, but yeah, it's very rare.
Kendall Baker: I just think about myself, and I think this is true for a lot of people. Like I rarely go to websites. I rarely intentionally decide to go find something. I mean, the only time I'm doing that is like a Google search, right?
We've almost trained ourselves in this social media era to open our feed and then we kind of know we'll find something eventually, and maybe you end up going down a rabbit hole, but there's very little intention anymore. And so I think the way to kind of break through that is to come to them, as opposed to relying on them to find you.
Turner Novak: Yeah, but then you probably also want to make sure that you're not solely reliant on just email as a channel, or just Instagram, just Facebook. Media companies have run into that problem, so you almost want like a multi-pronged approach.
It’s not just a multi-business model where you've got sponsorships, events, subscription, recruiting software, but also like, “Hey, we've got, email, texts, we have a bunch of people on Instagram to pull 'em in a bunch on TikTok or Twitter.” So if, if like one thing goes down, you still have multiple hooks and things to bring people in.
Kendall Baker: The only thing I'll say to that, which is kind of counter to that point, but not really, but it's just advice to anybody starting a newsletter. I do feel like it's kind of the default mode to… Let’s say you launch a newsletter. Of course you need a Twitter page, and a Facebook, and Instagram. You need all these things.
I found that especially when you're early on and you probably don't have that huge audience, I think you're actually better off not like having those accounts. Let's say you have a Twitter and you have five followers. Better not to have a Twitter. Why publicly make it clear that nobody follows you?
You need a strategy and a plan first, and the lack of that ends up doing you a disservice. I think, you know, if you launch a newsletter, maybe, maybe you also have an Instagram page, but be very intentional what it is for.
And sometimes I think people default to thinking “we need to have all these things,” but there's no plan. It's just like we have them, and we'll figure it out eventually.
Turner Novak: Maybe this is a good way to segue. You recently left Axios. Now you're going to Yahoo. Yahoo's a really interesting business, I forget the stat, but I think it's like the third most visited web property or something.
Kendall Baker: It’s like six or something, but whatever it is, it's a lot of people. Billions. Billions of visitors a month.
Turner Novak: What was your thought process on going from Axios, kind of this sexy newsletter, first media company? I think they just got acquired right? And now you're going to Yahoo, the fallen angel? Maybe you're in the middle of a turnaround, I'm not sure, but I'll let you dive into it. But what was the thought process? Because that seems like a crazy move on the surface.
Kendall Baker: So the thought process was a few things. I agree with you. I think Yahoo is in a really interesting spot, and I think ultimately it's a rocket ship. I'm really a big believer in the leadership there now, so that's obviously a big part of it. They just hired Ryan Spoon as the president of Yahoo Sports.
He's really well respected around sports media industry, worked at ESPN, so a big fan of his. A big fan of the CEO of Yahoo, Jim Lanzone. So that's, you know, first and foremost. I think anytime you're looking to go to a new company, if you really believe in the leaders and the people who are going to be calling the shots, what's more important than that?
I also think that of you think about how I'm in the business of newsletters and email, Yahoo literally has email. There are clear synergies there. It's the second biggest still behind Gmail. I mean, there’s some stats by Yahoo that people don't realize.
It’s the second most visited sports property on the internet behind ESPN. We said sixth biggest website. Second biggest email service behind Gmail. Yahoo Finance, I think is number one in finance. It's a huge audience. So that's some of the thinking.
The other thinking was audience, right? My goal with this newsletter is to build the biggest sports newsletter, if not just newsletter, in the world. And we're not there yet at Axios. I think we are in the hundreds of thousands of readers and I want to get to millions and a place that already has millions of readers feels like a great place to do that.
The other thing for me, just personally was, as much as I enjoyed being on the sports team at Axios, me and my colleague Jeff Tracy, who wrote this newsletter, we were the entire sports department at Axios. and that was really cool, in some respects. We weren’t competing for stories because we were the sports desk.
That being said, what excites me about Yahoo is that now I'm going to be surrounded by tens and almost hundred other sports reporters and be able to work with them, able to share a lot of their content in my newsletter. And so I just think for somebody who's obsessed with sports and just loves sports the way I do to be surrounded by colleagues who share that same passion as me is I think it’s hopefully going to ignite a lot more passion in me as I continue doing this.
And so I think it just makes a lot of sense for me as I continue this journey. In some respects I was just kind of hitting the ceiling at Axios in terms of covering sports at a place where sports is not the focus. And at Axios, I think we have one of the biggest sports news newsletters out there, but no matter how big that newsletter got, Axios was never going to be thought of or known for sports.
For me it's like I want to go to a place where the sky is the absolute limit. And I think Yahoo presents that opportunity.
Turner Novak: Yeah, because when I kind of think about too, where does Yahoo rank in, in terms of fantasy platforms? Are they pretty high on that too?
Kendall Baker: Yep.
Turner Novak: Okay. it's an interesting time for you to be joining because fantasy season's going to ramp up. How do you think about then like launching? Like does Yahoo have a sports newsletter?
Kendall Baker: Yeah. Yahoo has a sports newsletter. We're going to see how, how we leverage that and move forward. But I mean, the bottom line is that Yahoo's a really big believer in what I've been doing, which is another reason why I feel confident going there.
If I was going to a place where I really had to sell what I've been doing and point out why we should keep doing this, it would have been different. I'm going to a place where they said, “We love what you're doing, let's do it and let's make it even bigger and better.” So that really, really excites me.
And you mentioned Fantasy. I think betting kind of works into that too. It's all kind of this part of the same fandom but interacting and not just making predictions but actually acting on those predictions and I think Yahoo, fantasy embedding is all intertwined there.
Yahoo has Yahoo Sportsbook and Fantasy, so I think incorporating that all into my sports coverage, which is kind of this daily touchpoint for sports fans, you know, for so long I've basically been telling you the news and now I think I'm going to have a really cool opportunity to also intertwine betting and intertwine Fantasy and all these other things in ways I haven't, and just make that kind of daily experience for a sports fan much more engaging.
Turner Novak: Interesting. So, are you starting a new newsletter product at Yahoo? What's going to happen?
Kendall Baker: Yeah, newsletter product, but I would frame it as a continuation of this journey I've been on. So I started a newsletter in my room in San Francisco, just on my own, and then went to Axios and built that up into a very large audience and kind of figured out works, what doesn't.
And now with this, I'm kind of thinking about this as the next step in that and going after a much larger audience. Axios Sports was essentially what can two people put together, and not to say that you need that many more people to do it well, but I'm excited to see what can two people, but with the support of an entire newsroom, put together.
There were so many times over the last five years when I was just like, “Oh, if we had one more person, two more people think about what we could do,” because I just simply couldn't do it all. There were so many stories that like, “Oh, I would love to spend the next five hours reporting this out,” but guess what? I have to write five other things and then that story falls through the cracks.
Now I'm going to have a lot more resources, a lot more support that I can do that story. That will play in itself out over and over and over. And I think the end result will just be a better product.
Turner Novak: Interesting. I think you did have a really good product. Why do you think you were able to cut through the noise and get commissioners and sports VIPs to pay attention to you? This is actually a question from, I would label them as a VIP in the sports world. They wanted to remain anonymous. But what do you think you did right?
Kendall Baker: So I'd say there's a few things, but I'd say one that I'd definitely point to is from day one my hypothesis was I think you can combine sports news, with sports business news, which is news about the industry of sports and for so long.
Still to this day, those are very separate, right? Sports news is for the billions of fans around the world and sports business news is mostly for people who work in sports. A lot of that is stuff about TV ratings, and stuff we've talked about a little bit like sports holding the cable package together, like the business of sports.
I always thought if you make that sports business stuff interesting enough for your average sports fan, it's actually really intriguing for them. So from day one, I've combined them. I have some people who would consider my newsletter a sports business news newsletter. I don't think that is the case. I have other people who consider my newsletter, a sports newsletter.
I've, been able to combine the two, and I think the result is that not only does your typical sports fan read my newsletter, but I also have Adam Silver, the commissioner of NBA, reading it.
I think for Adam, he gets sports news as he's a sports fan, but he also gets news about the industry that he's in and it's all in the same place. When you combine them in the same place you’re able to connect the dots more.
If you're getting news about, what’s relevant to sports fans and news that's relevant to sports executives you kind of see the synergies between the two, and I don't think there's any reason why those have to be separate.
Turner Novak: Yeah, and to your point about Adam Silver reading, obviously he's probably getting some NBA news, but he is probably following interesting stuff in golf or into another sport that I probably should follow, but I'm not as in the weeds.
Kendall Baker: The benefit of having a newsletter where my value proposition to readers is that everything that is important in sports is going to be in there. If you're the commissioner of the NBA and you feel like, “Why aren't we in here today?” Or like, “I feel like we haven't seen as much coverage about us lately”, like if he trusts my judgment and I'm deeming there are not to be that many important NBA stories this week, for instance, maybe that's important to note. Maybe there's some, reflection that can happen there.
I think anybody who works in the business of sports, if they're seeing things mentioned a lot in my newsletter or they're seeing things not mentioned, it's a good reflection of what's really kind of hitting out there right now.
Turner Novak: What do you think is the most underrated or underreported story going on in sports right now?
Kendall Baker: To be clear, this is definitely being reported, so many people might not agree this is underreported. I just think it's underreported because as much as it has been reported, I don't think you can report on it enough, and that is just the momentum that is happening right now in the US around the sport of soccer.
And I think you're seeing that in many respects. Obviously the women are in the World Cup right now. Messi coming over. The MLS is huge. And it's all – there's a very intentional, push around soccer right now in the lead up to the 2026 World Cup. This the 2026 World Cup is going to break viewership records.
You're just seeing the event that’s three years out is mobilizing people at every level of soccer, from youth soccer to high school soccer, to college soccer. And then you have things like Messi coming to MLS There's just so much momentum.
For so long we've called the big four sports, NFL (football), NHL (hockey), NBA (basketball), and MLB (baseball), and soccer has always kind of been the fifth one there. Now, I think if you don’t consider leagues, but sports, you know, basketball, football, hockey, soccer…soccer's actually above hockey, and has been for a while.
Turner Novak: In terms of like participation rate?
Kendall Baker: In terms of participation interest. Many more Americans play youth soccer than, than hockey. But MLS is long been seen behind NHL, which is true because the best hockey players in the world play in the NHL, but the best soccer players in the world do not play in the MLS. And that's a result of soccer being, you know, the most popular sport in the world. And, you know, it's just a different situation.
But I think Messi is such a big figure – him signing for the MLS is such a game changer that you're now like reconsidering the question of “What are the big four leagues? Should it be Big the five?” That's a huge question in sports and I think the MLS moving forward is legitimately in the conversation in a way they haven't been.
So I just think overall just pay attention to soccer and there's a very intentional effort at all levels of the sport right now to make 2026 as big of a success as it could possibly be. It's going to be the biggest World Cup ever. You cannot report enough on soccer over the next few years.
Turner Novak: It's interesting that we went from, I don't know, we did the last World Cup in literally like the desert, 150 degree heat…it made no sense. Now we're doing it like in the US and it's just a, probably a better environment to actually host the tournament. Period.
There's probably going to be a lot of money that's made. Just talking about the business side of sports. There is just going to be a lot of money that people dish out and spend..
Kendall Baker: The field is going to be 48 teams. That's so many teams.
Turner Novak: Is that more than normal?
Kendall Baker: Oh yeah, its usually 32 so it’s significantly bigger. I can't wait. Put me on record saying that every viewership record will be broken. And this is in an era where viewership for things, even sports is going way down.
The importance of live sporting events of that magnitude are just becoming more and more important. There's only so many events every year, like the Super Bowl that everybody stops everything to watch.
You look at the Women's World Cup right now in New Zealand and Australia – the women played at 3:00 AM last night. And that's tough. Whereas when it's in the US and the games are in prime time, I mean, it's going to be huge
Turner Novak: Yeah. And then I think the argument I saw when Messi came over, people were like, “Oh, he's retiring, he's securing the bag.” He just won the World Cup, he was like the MVP!
Kendall Baker: Messi is still the best player on the field. And this is why sports are the best, because they're just unscripted and it's like things happen that are just absolutely incredible. Messi’s first MLS game – it was so hyped, could not be any more hyped – he comes on, and in his first game, in traditional fashion (as he has always been known for his free kicks), he comes on and scores the game winner.
You cannot script that. I mean, if somebody would've, scripted that, people would be like, no, that's too unrealistic.
Turner Novak: Who is the most underrated athlete in sports right now? Any level, any sport. Any country. Who's most underrated?
Kendall Baker: I would say within hockey circles… well this is not true because within hockey circles, people are aware of this. But I think within sports world they're not and so this is kind of a weird answer, but I think Connor McDavid is the most underrated player.
Connor McDavid, captain of the Edmonton Oilers. Source.
And the reason why is I think we're seeing maybe the greatest hockey player of all time. This is a hot take because he's still very young, but I literally think that's what we might be watching. And I don't think even some casual sports fans know who he is.
Turner Novak: Yeah. So for people who don't know, can you give us the quick rundown? I do know as a Canadian, I know who he is, but for people who don’t.
Kendall Baker: Connor McDavid is the best player in the NHL right now, plays for the Edmonton Oilers.
Turner Novak: Who Gretzky also played for. Wayne Gretzky is probably objectively the best hockey player, at least by most objective measures was the best.
Kendall Baker: This past season, Connor McDavid was doing things, and my newsletter's always full of like stats, and I can't tell you how many stats last year was like Connor McDavid, first player to do X, Y, Z since Wayne Gretzky. he's in a universe of his own. And Wayne Gretzky is often the only player that's ever done the things that he's doing. So he's the best player, absolutely no argument, in the NHL right now.
But you know, for American sports fans, the fact that he plays in Edmonton, the fact that hockey is a very regional sport and like it's not national in the same way that NBA is the NBA, regardless of who you root for where you are. You’re going to hear about what LeBron James did last night. That’s just that's how the media cycle works. That's how NBA fandom works. But I just think there's a lot of people out there who just don't fully understand that maybe the best hockey player to ever live is currently playing.
Turner Novak: Why is he so good? Like, is he fast? Can he hit, can he score, pass? Is it just everything?
Kendall Baker: He's an all-round… he's just really good at everything. I mean, I think if you could point to one thing that's just visibly, like jumps off the screen the most is his speed. And in hockey, it's different from like soccer or basketball. It's like sprint speed and skating speed is just a skill.
When somebody is just faster than everybody else on skates, it's crazy to watch. And I think there's just highlight after highlight of Conor McDavid getting the puck. He's got three defenders in front of him, and then like two seconds later, he just has just weaved through them and the puck is not an inch away from his stick and it's just mind blowing to watch. So I'd say his speed is the one thing that stands out the most, but he's really all around just fantastic at everything.
Turner Novak: Who do you think is the most underrated athlete of all time?
Kendall Baker: Oof. That's a great question. I might go with another like weird answer of like, somebody who people definitely know is great.
Turner Novak: That's totally okay.
Kendall Baker: Tim Duncan.
Turner Novak: Interesting.
Kendall Baker: Yeah, I think Tim Duncan is one of those guys that when people make lists of like top 20 players of all time is rarely on that list because people don't like close their eyes and picture Tim Duncan highlight reels in the way they picture like Kobe Bryant highlight reels or Wilt Chamberlain because Tim Duncan's kind of boring.
Athletes that just win and just get it done, and who aren't sexy they oftentimes get underrated when they're playing. But mostly and even more so after they're done playing, because they kind of get lost and the only time they really show up is in like record books.
I think a lot of times when we think about all-time greats, it is the highlight reels that are like playing in our heads that we can like remember and it's not the stats. I just think with Tim Duncan, the stats would support him being in the top 20 of all time, if not higher.
I just don't think he appears on enough of those lists. And I think that makes him extremely underrated. He just is one of the best winners in NBA history and I would put him up there for sure.
Tim Duncan spent his entire 19-year career with the San Antonio Spurs. Source.
Turner Novak: And so Tim Duncan was, I think either center or power forward. He was like the tall guy…he played for I think the San Antonio Spurs…did they win a couple championships?
Kendall Baker: Oh yeah, yeah. He won multiple championships with multiple different supporting casts around him. At one point he played with David Robinson, who was a fellow seven-footer. So his early career they had like the twin towers thing going.
Then the more modern Tim Duncan in the two thousands, people might remember the rivalry between the Spurs and the Heat. They kept meeting in the NBA finals and it was, you know, Tim Duncan, Manu Ginobli who I believe is from Argentina, Tony Parker, who's from France, and then Kawhi Leonard in his early career before he went to the Raptors and subsequently the Clippers. That Spurs team was just 10 deep and just ball movement. It was just the ultimate team.
Turner Novak: I kind of remember, but that's a good point just him being underrated. Last question. Do you have a CEO or a founder that you really look up to or really respect?
Kendall Baker: There’s certainly a long list there. I don't know him and I don't know enough about him in terms of his leadership style and things like that to really speak to that part of it. But for me, as somebody who is a sports writer, but who has also always considered myself entrepreneurial, like I wanted to start a business someday and I kind of did with Sports Internet, although it was just a one-person newsletter so I don't really consider it that. I would say Bill Simmons. His career trajectory really speaks to me in terms of kind of balancing being a voice and a writer and somebody who speaks about sports but also thinks about sports media.
From a business perspective and what he was able to do going from being a writer at ESPN to starting Grantland, which is one of my favorite websites, to then starting the Ringer, and then ended up pivoting really hard into podcasts and selling that company to Spotify. That's just somebody who like speaks to my interest of sports writing, sports media, but also the business of sports media.
Turner Novak: Yeah, he’s done a really good job. I'm not super close follower. But I've heard of him so that probably means a lot.
Well, Kendall, this has been great. Thank you for coming on. This is really interesting for people. Anyone interested in media, newsletters, sports. We talked about a lot of interesting stuff.
Kendall Baker: Thanks man. This is awesome. I really appreciate you having me on and awesome conversation.
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