How to Get 1M Subscribers 📨

Happy Wednesday,

Kendall Baker has been writing daily sports newsletters longer than almost anyone. He started at Bleacher Report and ESPN, went to San Francisco to help build The Hustle into a $40M acquisition, came back to sports with a newsletter called Sports Internet, sold that to Axios, and eventually ended up at Yahoo, where he now writes Yahoo Sports AM, a newsletter with over a million subscribers.

I'll be honest, this was a selfish episode for me. As someone who writes a newsletter and wants to grow it, I wanted an hour with the best in the business. Hopefully you get something out of it too.

🎧 [Listen to the full episode]

If you’ve ever read one of Kendall’s newsletters, you might notice he does something strange: he promotes his competitors.

He features work from journalists at other outlets, links to social posts that aren’t his, and even shared a link to GeoSports just three days after Frank Michael Smith launched it, helping the game reach 100,000+ daily users.

On the surface, this seems like a terrible business strategy (encouraging people to click off of your newsletter), but it’s actually the whole business.

His reasoning: the number one thing he needs to maintain with readers is trust. The minute he omits something because he didn't write it, buries something because it competes with him, or shapes the newsletter around what's good for Yahoo instead of what's good for the reader, he's lost the thing that makes the product worth opening in the first place.

But there’s another layer.

AI is already very good at aggregating information. It can scan every source, identify the most important stories, and organize them into something readable in seconds. What it can't do is build a human-to-human connection. It can't develop the decade-long editorial instinct for what belongs and what doesn't. It can't include the random thing that has no business being there (which could be the thing readers end up remembering most). It can't build the kind of parasocial relationship where someone emails Kendall because he missed a day and wanted to make sure he’s okay.

Kendall has over a million subscribers, yet he still responds to reader emails, asks for feedback when he tries something new, and includes things that have no utilitarian value but somehow make the whole newsletter more alive. None of that scales in the way a social platform scales, or is as efficient as having AI curate stories, but it compounds in a way that social and machine learning never will because the people who trust you will follow you anywhere.

That's worth more than an algorithm ever will be.

1. Spend the first three months trying fifty different formats.
When Kendall launched Sports Internet, he didn't lock in a format and stick to it. He tried four main stories; he tried an A-B-C block like a show rundown; he pulled inspiration from late-night TV, from other mediums, from formats that had nothing to do with sports. The product that exists today is the result of ten years of iteration that started with deliberate experimentation. If you start a newsletter and immediately copy the format of something that works, you're already behind.

2. Newsletter readers are their own demographic.
This was the counterintuitive growth insight Kendall shared, and it stuck with me. Growing a newsletter by targeting people on social media is hard. Growing it by partnering with other newsletters (even completely unrelated ones) works surprisingly well. His reasoning: someone who already reads a newsletter is dramatically more likely to start reading another one than someone who doesn't read any. Newsletter readers are a demo, so find them where they already are.

3. The one thing AI can't replicate is the random thing that has no business being there.
Kendall's best example was Mike Allen's One Fun Thing at the bottom of Axios AM, a completely random moment at the end of an otherwise intensely “hard news” newsletter. No algorithm would ever put that there, no AI would know to include it, but it's often what people remembered most. The human gut feeling for what creates joy in a reader, the meandering connection that has no utilitarian value but somehow makes the whole thing more alive, that's the thing that compounds over years and can't be manufactured.

4. The thing that makes newsletters hard to grow is also what makes them worth building.
Kendall was blunt about this: newsletters will never go viral the way social does. You can't manufacture growth or “hack” the algorithm. Every subscriber has to actively choose to be there, which means growth is slow, deliberate, and genuinely hard. But that difficulty is the point. The people who find you and stay are there because they want to be, not because a feed pushed you in front of them for three seconds. That's a different kind of audience, and unlike a TikTok following, it can actually move with you.

5. The future of newsletters might look like a magazine you didn't know you were subscribing to.
Kendall's big idea at Yahoo is building a newsletter network, not acquiring newsletters outright, but partnering with them the way The Ringer partners with podcasters. The analogy he kept coming back to was bundling. There are too many newsletters now, the inbox has a limit, and at some point readers are going to want someone to curate the curation. The media company that figures out how to do that for newsletters is going to look a lot like what magazines were, except distributed, creator-led, and much harder to replicate.

I'll be honest, this was a selfish episode for me. I have a newsletter, and I want to grow it. But the thing I keep coming back to isn't a growth hack or a format tip; it’s the discipline required to succeed in the medium.

Kendall wrote in raw HTML for a year because today’s newsletter tools didn't exist yet. He stayed up until 3 AM in San Francisco to cover the late West Coast games because that's the only way to do it right. He wrote a newsletter the day after he got married. He did all of this before he had a team, before he had a platform, before he had any real evidence it was going to work, just the conviction that if he kept showing up, the audience would too.

That's not a strategy you can shortcut. You can't vibe code your way to a decade of daily discipline. And I think that's actually the most important thing Kendall said today, even though he never said it directly. The newsletter itself didn’t build the trust; the showing up did. Every single morning, for ten years, giving readers something worth opening. That’s what it takes to build a million-person audience

I think about that a lot when I sit down twice a week to write this newsletter. Not the open rate, not the subscriber count, not which brands are paying attention. Just: is this worth someone's morning tomorrow?

That's literally the whole job.

🎧 [Listen to the full episode]

📩 And don’t forget: Bottom of the Ninth is back this Friday with the top three stories in sports and business from the week.

See you then,
Tyler & Jake