Extra Points by Matt Brown

How Matt turned on paid subscription after getting laid off and currently earns $16k a month from paid subs.

Interview Date: December 8, 2024

Table of Content

Meet Matt Brown
Newsletter Identity Card
Tool Stack
How he started his newsletter
Growth guideline to over 28,000 subscribers
His monetization strategies
Personal & professional impact of running a newsletter
Biggest advice to newsletter creators

MEET THE CREATOR

Matt Brown is a former sportswriter and editor at Vox Media. He started Extra Points when he was still working at his corporate job. In 2020, he was laid off, and there was no other editorial job due to the pandemic.

This was a milestone for Matt as he turned on paid subscription, and things started to change for Matt. Now he earns $16K a month only from paid subscribers.

In this interview, Matt talked about:

how he started and grew his newsletter to 28,000 subscribers
how he earns more than $16K a month from paid subscribers
how Extra Points changed his life professionally and personally
his biggest advice to other newsletter operators

Enjoy!

NEWSLETTER IDENTITY CARD

TOOL STACK

ESP: Beehiiv*
Writing: Writes directly in the CMS.
Task Management: Slack, Trello, Apollo, Google Sheets
Digital Products: Bubble
Payments: Stripe

START

How and why did you start Extra Points in the first place?

Back in 2019, I was working for Vox Media as a sportswriter and editor. We had a corporate reorganization and my job became less editorially focused, but my contract prohibited me from writing anywhere else.

I decided to start a free newsletter, hoping that I could learn more about the medium, and perhaps persuade Vox to either buy it or let me write the publication for them. It was very much a side project at that time.

But in 2020, Vox decided to use the pandemic as a catalyst for doing something they were hoping to do anyway….gut the sports department. I was laid off, and suddenly, because there were no sporting events, I had basically no shot of finding another editorial job.

I wish I could say I launched Extra Points out of a fit of entrepreneurial inspiration, desperate to throw off the yolk of tyrannical and out-of-touch publishers and executives. The reality was…I needed a job!

“I figured EP would be a side project to tide me over until I could get hired at The Athletic or something…but in about six months, I realized that no, actually, this was going to be my job now. And I’m very thankful for that because this is the best job I’ve ever had.”

GROWTH

You grew your subscriber number from 0 to 28,000 in 4 years. This is impressive. How did you gain your first 1,000 subscribers?

This might not make great advice for would-be publishers, but I got my first 1,000 subscribers pretty much in the first 72 hours of starting the publication. They weren’t all paying subscribers, of course, but I did get a small list going pretty quickly.

I’m not famous or anything, and was certainly less notable in 2020 than I am now, but before EP, I had a X account with 20,000+ followers, had published a book, and had been writing professionally for years. I had an audience already. I just needed to grow it.

Growth strategies can vary at different stages of a newsletter journey. Which strategies did you use to grow over 28,000 subscribers?

1,000 – 10,000 Subscribers

Overwhelmingly organic. I’m very active on X (less now post-Elon, but still active), as is my core audience of die-hard weirdo college sports fans.

By simply sharing my stuff, participating in regular conversations, and cultivating relationships with other reporters/radio stations, I could get booked on podcasts/radio shows pretty easily, and have other folks amplifying my work.

There is another college sports industry publication, called D1.ticker, that regularly aggregated my work as well, which helped me get in front of more industry professionals.

I probably did a few giveaways as I approached big numbers like 5,000 and 10,000, but I remember growth at this stage being overwhelmingly organic.

10,000 – 25,000 Subscribers

Similar to the first 10K, honestly. I regularly encouraged my readers to share the newsletter with colleagues and friends, even including a referral reward program (to mixed results).

I purchased a much smaller publication (~1,000 subs) and merged it with mine, which ended with around a net gain of 650 or so. I also began to experiment with cold outbound pitches…inviting athletic directors or coaches who didn’t currently subscribe to do so.

We experimented with podcast advertising and newsletter swaps but found that to generally be too expensive to be profitable, or not driving enough high-quality subscribers.

25,000 Subscribers – today

We’ve begun to experiment with social media ads now (Facebook and X), which has been okay at driving subscriptions, but not very effective at driving high-quality subscribers (i.e., those who are heavily engaged or eventually upgrade to paid subscriptions). I think we’ll look at paying for PR services next year, as well as more aggressive outbound sales.

The truth is, we don’t care that much about total subs, because that isn’t where we make the bulk of our revenue.

“The best way that I’ve ever found to drive high-quality subscriptions is to regularly produce high-quality, completely unique, content. That creates earned media opportunities and organic reach that we have not been able to replicate via paid channels.”

Regarding growth efforts, what would you do differently if you had a chance to start over?

In some ways, it might be easier for me to start over…I’m a bigger “name” in my industry in 2024 than I was in 2019, 2020, with more sources, a bigger social audience, and a deeper relationship with my audience. But changes in X’s ownership and consumer behavior on other social media platforms would make growing a newsletter audience organically on social much, much harder.

I think I would probably allocate more money and time to marketing if I started a completely new newsletter project now, leaning into paid ads, paid recommendations and paid PR efforts earlier. Of course, I couldn’t do that in 2020…because there was a pandemic, I had a wife and two kids to support, and I didn’t have a job lol. I had no choice but to bootstrap everything!

MONETIZATION

When was the right time for you to apply paid subscription for your newsletter? How long did it take to monetize your newsletter?

I turned on paid subscriptions less than 48 hours after I lost my job at Vox. That’s when I decided to give Extra Points my full-time energy and shift from two (more aggregate) posts a week to four (mostly reported) newsletters a week. I got 100+ paid subscribers less than 48 hours after I turned the paywall on, which also helped demonstrate that I was on the right track.

“I think if you’re a publisher that is capable of producing valuable content that can’t be easily found elsewhere for free, you should turn the paywall on as soon as possible.”

I don’t think I sold my first newsletter ad until I had been publishing for…maybe five or six months. But I was earning subscription revenue in week one.

How many paid subscribers do you have? What are your strategies to convert free subscribers into paid ones or gain new paid subscribers?

The exact number fluctuates because we do a lot of discounted student subscriptions (Extra Points is used as a textbook for some Sports Management classes), but I’m comfortable saying we average over 16K a month in MRR from paid newsletter subscriptions.

I run sales a few times a year, but I’ve found that our audience isn’t very price-sensitive. The most effective ways so far have been to produce reporting that folks feel is worth nine bucks a month, to paywall AFTER a few paragraphs of a story to help build some FOMO, and to be very transparent with my readers about why we’re asking for money and what we’ll do with it.

I have room to grow here as far as audience segmentation and targeted upsells are concerned, but that’s what has worked for me so far.

FWIW, I also believe many of our readers pay to support EP because they like me and feel invested in our mission and our community.

How did you decide what to offer differently to paid subscribers to make it compelling for them to join as paid members?

This is an art, rather than a science, right? This wasn’t something I did a ton of focus group testing on or anything…I sort of did a ready-fire, aim sort of approach.

I knew I had the capacity to produce four newsletters, but I didn’t have the capacity (at launch) to add subscriber value beyond writing and reporting, so I figured I’d start with what I knew I could produce.

I typically err on the side of making my most insider-y stories paywalled, and the more broad-appeal stories free (to try and grow the top of my funnel), but there are some exceptions.

“I’ve learned, for example, that stories about video game development drive subscriptions at a higher clip than my other reporting topics, so when I have news to break there, I generally paywall it. That just comes with time, experience, and data.”

What are your biggest learnings when applying for a successful paid subscription?

The biggest mistake I see other newsletters make when they try to monetize via paid subscriptions is with their content. MORE stuff is not the value proposition you think it is…it has to be the RIGHT stuff.

I am not charging people money because I am a better aggregator than what they can find for free, or a better curator.

I’m charging people money because I have the professional experience, insights, and reporting ability, on the issues they care about, that they can’t easily get for free. You simply have to know your niche and deliver real value. The value prop that I offered in 2020 isn’t the same one that I offer now, and that comes from knowing and listening to your audience.

But my TL;DR is that if you don’t love making the content, this isn’t the business for you. That’s got to be the most important part.

What are your key strategies to find and get sponsorships?

Honestly, I’m still not very good at this. In my experience, the newsletter ad support infrastructure is built mostly to support publications covering Web3, AI, Startups, SaaS, or investing…basically, a turbo-LinkedIn.

I am not that publication, and I do not have the scale to just ride affiliate ads from general consumer brands. I have to do my own direct sales, and mostly, I have to convince brands to spend on a newsletter for the first time.

I think my biggest key strategy is that if you don’t think your publication can get to 50K+ subs in a reasonable amount of time, don’t even bother with sponsorships…or at least, treat it like found money.

“I make more money from 28K subs selling subscriptions than I think I would from ads if I had 125,000 total subscribers, tbh. “

IMPACT & LEARNINGS

How did building Extra Points newsletter contribute to your life professionally and personally?

It isn’t an exaggeration to say it’s completely changed my life.

On the obvious side, I make more money writing and running Extra Points than at Vox, or in any other sportswriting or corporate job I’ve had. I’m not RICH or anything, but this has provided a level of stability that I haven’t really had before in my career…and a potential pathway to grow even more.

But more importantly, my boss (me) cares just as much about the quality of my work as I do. Something that didn’t happen very often in my journalism career (or career generally) elsewhere. I work on the stories I want to work on.

I don’t have a corporate mandate to pivot to platforms I don’t believe in. I can tell a potential ad partner that I don’t want to work with them. I don’t really have to care about scale. That is a very, very freeing feeling.

Of course, it also comes with pressure. I’ve worked more hours as an indie than I did as a staff writer or editor, and I’ve had to spend a lot of time doing stuff that isn’t writing or reporting…like sales, tech stack management, paperwork, hiring, etc. That’s not for everybody, and I can’t lie and say I’ve cracked the work-life balance secret code. I have not, as my wife and children will tell you.

“But starting EP has given me career direction, focus, and success in a way that I haven’t enjoyed before. I’ve met wonderful and interesting people, traveled across the country, and built something new…which has given me the confidence to know that if I REALLY had to…I could do it all again.”

What would you do differently if you had a chance to start over Extra Points?

I would write less and charge more money for it.

Seriously. I write more than most newsletter publishers, and I know my audience doesn’t have time to read it all. I felt like I had to overproduce to justify asking for money… and that just isn’t true.

What would it be if you had the right to give one piece of advice to aspiring newsletter creators?

Find a lane that is uniquely yours, one where you won’t get bored from writing and researching about every day. Then master that lane. If you do that, you’ll always have a job.

Final words, if you have any?

Nothing matters as much as your content. Forget your newsletter tech stack. Forget your A/B testing. Forget AI (seriously, please forget AI, don’t have AI write your newsletter). If you don’t want to do the work to create actually meaningful and unique writing, don’t get into the newsletter business. Find another place for your talents and interests.