🎧🍌 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

Stream on:

👉 Apple

👉 Spotify

👉 YouTube

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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

👉 Find on Apple and Spotify

🙏 Thanks to Zac and Xavier at Supermix helping with production and distribution!

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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?