Rebranding a newsletter (38k subs)

Haroon Choudery is committed to making technology accessible to everyone. Haroon and his brother Hamza immigrated to Brooklyn from rural Pakistan in 1998, and both brothers launched tech careers after college.

But while they were finding success in the tech world, they were watching how tech could destroy a blue-collar business owner in real time. The Chouderys’ uncle was a New York City taxi driver who lost everything when the ride-share boom exploded. He had to start from scratch after spending two decades and investing his life savings in a business.

The juxtaposition of watching their uncle lose everything to new technology while they were building lucrative tech careers had a powerful effect on the Choudery brothers. As a result, they co-founded one of the world's largest AI education nonprofits, AI for Anyone.

The brothers’ mission at AI for Anyone is to enable underrepresented populations to participate in the tech revolution rather than being bulldozed by it. Over the past five years, the org has taught over 3,000 students in New York City the basics of AI to help them prepare for the future. In addition to those in-person classes, AI for Anyone has taught over 70,000 people online.

Haroon Choudery has been running a newsletter as a separate entity alongside the nonprofit.

Keep reading to learn:

• Pivoting newsletter content and branding (and managing the following friction)

• Using your business + career to power a standalone newsletter

• Strategies to increase subscribers and engagements

Or subscribe here:

Let's get into it:

A Personality Facelift to Fit a Popular Space

When AI became the hottest topic on the planet, Choudery decided a newsletter rebrand was necessary.

"Our original newsletter had a different purpose. Once every two weeks, we would cover the latest AI research. So it was very academic. But very recently, we saw a huge influx of people and interest in the AI space, and a lot of people [started] creating AI newsletters."

But interest does not mean expertise.

"Very frankly," Choudery laughs, "most of them have no idea how AI actually works. We've been doing this for quite some time, and we realized that we need to play the game in order to be successful. Otherwise, we're going to be washed out by a ton of the newer AI newsletters that are doing a better job of growing."

That's when Choudery decided to rebrand the newsletter. He changed the name from All About AI to Not a Bot. Also, he says, "We moved over to beehiiv and haven't turned back."

Why make the change?

Choudery says, "The rebrand was focused on making the newsletter less academic and more practical. More plugged into the latest tools and the latest news in the space. And also shifting from a biweekly cadence to a once-a-weekday cadence. And then, alongside that, we went with a name rebrand and a logo rebrand. A personality facelift, I guess you could say, for the newsletter."

The Friction of Reinvention

Change always involves friction. Choudery was very aware that his subscribers at the time of the transition had signed up for a more academic and less frequent version of the newsletter.

"I was okay with taking a hit on subscribers to reposition ourselves so we were set up for more long-term success. I didn't think the academic angle would be conducive to growth, so even if it took a little friction to make that pivot, I was fine with that."

He decided to meet the challenge with lots of clear communication and a commitment to building a solid audience for the new brand.

"We made it very clear we were going through a rebrand and that the cadence and personality would change. The first issue was very transparent around all of those details. I also made it very easy to unsubscribe — although most folks enjoyed the new format and stuck around."

Choudery also seized the opportunity to clean his list and start fresh.

"I actively removed about 10,000 inactive subscribers from our list. I wanted to start with a fresh slate of folks that were engaged and interested in the content. So after three sends, I cleared subscribers who hadn't opened any of those emails."

Choudery feels like the transition has been worthwhile. "Obviously, there are some growing pains associated with a rebrand. But I think the short-term hit we took in removing some folks will pay dividends in the long run, and we're already seeing that.”

All signs pointed to success for the rebrand. Early on, those signs were most evident on social media.

“From a social media perspective, the buzz has never been higher around our newsletter. We have some exciting projects we're going to roll out that align with the new ethos of our brand, Not a Bot."

After cleaning the list, Not a Bot is left with around 38,000 subscribers. The average open rate is around 39% and tracking upward, and the average click-through rate is 2.9%. Choudery knows his click-through rate is a bit lower than some other newsletters in the AI space, but he says, "I'm not trying to be too clickbaity about it. Quality over quantity, trying to find a good balance between the two."

A Voice with Authority

In some ways, the new content strategy is a continuation of the same mission, but with a broader reach.

"The entire ethos of AI for Anyone was to make AI intelligible for the everyday person. That's what we have done for the past five years for high school students and young professionals. And now, what we're trying to do with Not a Bot is make the latest industry news accessible to the everyday person."

But when it comes to differentiating themselves in a crowded space, Not a Bot's advantage is that they're speaking as long-term experts in the industry who already know how to make AI accessible to everyone.

"On one hand, we're going for a 'simpler is better' strategy. But, on the other hand, that's also where many of the new AI newsletters compete. So the way we've been approaching it has been through a unique voice. I speak from my own perspective, having taught AI for the past five years. So I can take those concepts and simplify them for folks."

There’s more to his ethos, though, than accessibility.

"Also, trustworthiness is something that helps differentiate us. A lot of the folks that are starting AI newsletters may not come from an AI background. I've talked to a lot of them, and they're marketers who are just casually interested in AI.”

It’s not about exclusivity or gatekeeping, though; having an AI background means readers can trust the content to be accurate.

“A lot of the content I've seen on Twitter [and elsewhere] is just plain inaccurate. For example, just yesterday I saw somebody get tripped up reporting sarcastic news about AI, but they thought it was real."

"Those types of things are a little trickier to navigate when you're working with somebody who doesn't have that background. So, I think having that trustworthiness, having been a machine learning engineer, will give us more credibility."

Growth Focused and Mission Driven

While the writing style is meant to be accessible to anyone, the target audience for Not a Bot is people who are interested in AI.

That's an area where interest is surging at the moment, but unlike many interest-based creators, Choudery is focused on keeping a clear head and not getting caught up in the hype. For example, while monetization is part of the long-term roadmap for Not a Bot, Choudery says the immediate goal is more growth-focused and mission-driven.

"We're toying with monetization here and there. But the main purpose is the same thing that it's been for the past five years — to share AI knowledge and news and what's going on in the space. A big differentiator for us is that we're not running a get-rich-quick scheme."

"Obviously the space is red hot right now, but we didn't just jump in a few weeks ago,” he adds. “We've been doing this for the past five years, and we're in it for the long run. If [interest in] AI eventually goes down, you're not going to see us moving on to the next hot technology."

Growth Strategies

Bringing that credible voice to a broader audience is the focus of Choudery's current projects, which include an interview series, an expanded social media presence, and a web-based tool.

Expert Q&As

"A couple of weeks ago, we launched a Q&A series. I want to pull in all the interesting people I know and have them talk about generative AI. The first guest was Mark Cuban. I used to work for Mark, so I had that relationship. I'm planning on [interviewing] a lot of core AI builders, but I also really enjoy conversations with folks who are tangentially in the AI space because I think they bring a unique perspective.

"Mark Cuban, for example, has thoughts on AI in sports, which could be a gateway into AI. So maybe [some readers] weren't interested in AI, but they were interested in sports, and now they see the intersection of the two, and all of a sudden, in reading Mark's interview, they're interested in AI."

This gateway interest is part of an approach Choudery calls "The Disney Principle."

"At almost 30 years old, when I watch a Disney film, I enjoy it just as much as I did as a kid, but for different reasons. You see different levels of complexity in those movies; you might see deeper meanings [as an adult]. Similarly, I created AI education workshops based on what would resonate with multiple levels of complexity. Some things would resonate with professionals and some things would resonate with students.”

Choudery is bringing that same approach to Not a Bot. “That’s exactly what I’m trying to do with the newsletter as well. It should appeal to multiple levels of complexity, from very simple to a bit more sophisticated. And when it comes to doing these interviews with experts, another benefit is that it ties in AI concepts you may not have thought about."

Social Media

Social media is another area Choudery is using to broaden his audience.

"Twitter is such a treasure trove for AI news — really any industry news. So I'm trying to build more of a presence there. LinkedIn is another area where I'm going to spend a bit more time on building distribution."

Web-based Tool

Choudery's third growth strategy is to build a web-based resource for discovering AI applications.

"There are plenty of things like this out there, but I'm using my knowledge as a former machine learning engineer to build something that is really cool, and makes it super easy to find the right tool to solve a particular problem. Building that two-sided marketplace of AI builders and folks interested in AI tools is something that I think will be conducive to growth for us as well. Not a Bot could become an outlet where the top tools are being shared."

Note: Since we spoke with Choudery, his Igniter tool has launched on Product Hunt.

Not a Bot has only been on the beehiiv platform for a few weeks, but Choudery is already encouraged by his experiments with the platform's built-in growth tools. "Recommendations have been great. So far, I think I've probably given more recommendations than I've gotten, but it's somewhere around a hundred subscribers, which is pretty good for only a couple of weeks."

He's also started testing the referral program. "I have some Google AIY kits to give away that each retail at a hundred bucks. So I've been doing a giveaway where you get an entry if you've referred five people. [So far] about 50 users were referred. I think I can ramp that up if I bring [the entry threshold] down to one share."

Ambitious Goals

For now, Choudery is handling all these projects and the daily newsletter content himself.

"Right now, it's just me. All the 'AI for Anyone' volunteers are working on different functions. I want this to be my direct-to-subscriber communication platform. So I'm doing everything myself. In the mornings, it's probably an hour and a half to send out an issue. I also think it's useful doing that research on my own since I'm also building in the space."

Even though he's a team of one producing daily content, Choudery has set some ambitious growth goals for 2023.

"Right now, my main priority is getting momentum back up, but I am trusting the process. I know that what we're putting out is quality. I know the interviews we have lined up are great. I'm really excited about the app, and I want to hit 150,000 subscribers by the end of the year."

Choudery admits that goal might seem lofty.

"It's pretty ambitious, I think, given that there's obviously a lot of competition in the space and other folks trying to do the same thing. But we're shooting for the stars here, and I genuinely think that with all the initiatives we're working on, the start may be slow but I eventually want to hit that number.

So growth, above anything, is my priority. Monetization and all that stuff is less of a priority. I'll dabble in it, but if I have to make trade-offs between growing sustainably versus monetizing, I would absolutely go for the former."

Interested in AI? Subscribe to the Not a Bot newsletter, or check out recent issues like the Q&A with Mark Cuban or whether ChatGTP correctly predicted the Super Bowl.