Meet The Hustle and Morning Brew Alums Shaping the Future of Newsletters

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When you think of the newsletter you most trust at this moment in time, where does your mind turn? Maybe it’s to one of the daily emails that comes out from a traditional media brand, like the New York Times or the Economist. Perhaps it’s something from a digital brand, like The Gist or The Newsette. Maybe it’s from a writer you love or a friend covering anything from cooking to houseplants to neighborhood news. The inbox is an ecosystem where huge companies and independent writers can compete equally for attention.

There was a time, however, when the concept of an email newsletter was seen as antiquated. Many big newsletters were simply RSS feeds delivered to the inbox, monetized through programmatic ads. 

In such an era, The Hustle and Morning Brew rolled onto the scene, starting as passion projects and quickly transforming into media companies. It was the beginning of a newsletter boom that gripped the 2010s and has continued into the 2020s. Both The Hustle and Morning Brew received plaudits for amassing millions of subscriptions and building must-read products while legacy outlets struggled to adapt to the digital landscape.

What happened next is a straightforward and standard Silicon Valley tale — but not one you might expect for an indie newsletter operation. In October 2020, Insider — the parent company of Business Insider — purchased a controlling stake in Morning Brew for a reported $75 million. A few months later, in February 2021, HubSpot purchased The Hustle for a reported $27 million. The indie newsletter landscape had experienced a vibe shift, and it was no longer the domain of millennial techies looking for a quick news fix. The quintessential adults in the room had come to crash the party now that newsletters had proven viable and profitable.

Many factors catapulted the publications’ rise: a new generational approach to consuming information, the breakdown of traditional outlets, and the pandemic. But The Hustle and Morning Brew weren’t just in the right place at the right time. The creators and contributors working behind the scenes were pivotal to their rise. Many of them have now struck out on their own with their own newsletter-focused businesses to help creators navigate the new opportunities in the digital space.

Some of the alumni making a name for themselves:

• Katy Huff and Ben Alexander, the former sales leads for The Hustle, now run MadRev, where they sell ads on behalf of other newsletters.
• Matt McGarry, who ran growth marketing at The Hustle, now helps other newsletters acquire email subscribers through his company, GrowLetter.
• Tyler Denk, who built much of Morning Brew’s initial product infrastructure, now runs Beehiiv, a fast-growing newsletter platform that’s home to newsletters like Milk Road and Miss Excel.
• Jenny Rothenberg, Morning Brew’s director of growth, launched Smooth Media alongside several ex-Morning Brew colleagues to help creators write newsletters and run their businesses. 

While each of their companies focuses on different aspects of the newsletter industry, from selling ad space to building growth platforms, they all cut their teeth in the early years of The Hustle or Morning Brew.

I reached out to them to get their thoughts on how their earlier experiences shaped their approach to newsletters, informed their current projects, and shifted their views on the future of newsletters. But more than anything, I wanted to know: What about working at these two publications helped make them some of the foremost experts on newsletters today?

Newsletters as a start-up training ground

If there was one word to describe the staff at either The Hustle or Morning Brew, it was “entrepreneurial.” This was the adjective nearly everyone I talked to used to describe the attitude that permeated both companies.

“We were all very young and ambitious,” said Tyler Denk, the former senior product lead at Morning Brew. “That’s the core group of people [Morning Brew] attracted, especially in the early days.”

Morning Brew started as a .pdf of business news sent daily by Alex Lieberman and Austin Rief to fellow students at the University of Michigan. (The newsletter officially launched in March 2015.) After college, both initially took full-time jobs in finance and worked on Morning Brew as a side project. But by 2017, with Morning Brew growing to over 100,000 subscribers, they each took the leap to work on the newsletter full-time.

Denk, just Morning Brew’s second-ever hire, was put in charge of building out the company’s content management system and deliverability strategy. “I was managing half a million dollars a month in spending and building the entire ecosystem as a 23-year-old,” Denk said. “There was a huge learning curve, but a lot of room to learn and push boundaries. I didn’t really know any better.” At many companies, that sort of responsibility would have been handed to someone more senior — but at Morning Brew, where the early members of the team were all in their 20s, Denk and the team had to find their own solutions to big problems.

The Hustle was born out of a 2013 conference organized by Eric Bahn and Elizabeth Yin called Hustle Con, which aimed to offer tactical advice to start-up founders. In 2014, they added another organizer to the conference: Sam Parr, a serial entrepreneur. With Parr, the conference grew to about 600 attendees — and in 2015, led to the launch of The Hustle, a newsletter that aimed to bring the spirit of the conference to the inbox. The newsletter shared a mix of business news and how-they-built-it stories of entrepreneurship. 

So it makes sense that The Hustle attracted a staff that was unafraid to try new things. Matt McGarry, the former growth marketing manager at The Hustle, said his colleagues always wanted to launch new projects. “Even if they didn’t work there, they still would’ve done something because it’s just the type of people that they were,” he said.

Considering that many of these operations began with small budgets and small teams, that drive was essential to churn out the daily newsletters their readers expected. It’s common today to see businesses launch first with a newsletter — but at the time, there was no such blueprint or even tried-and-true tools to use.

Though other interviewed alumni had different roles in their organizations, they all echoed a “learning by doing” ethos that allowed them to take risks. Because it was still an industry in its infancy, this experience offered them insights into what made a newsletter successful that tech and media experts were still not privy to. By relying on their own data, they could understand how readers interacted with their products, what trends were on the rise, and which avenues were most effective for growth and monetization.

At a company like Morning Brew, that meant coding their own referral program since off-the-shelf tools didn’t yet exist. At The Hustle, that meant working hard to convince advertisers that a newsletter could be a more effective venue than, say, a billboard or a radio spot. “It helped me get really good at communicating the value to brands,” said Katy Huff, who was part of the sales team at The Hustle.

Both newsletters grew to remarkable sizes, especially considering their origin stories. By the time Morning Brew sold to Insider, their main list had grown to 2.5 million subscribers, and they’d launched several B2B newsletters and a popular business podcast. When The Hustle sold to HubSpot, they had 1.5 million subscribers on their list.

After their respective acquisitions, it was the end of an era for the alumni I interviewed. Whether due to restructuring or by choice, they eventually left the companies and began seeking other opportunities to share their knowledge. In the end, they gravitated towards building their own companies in the newsletter spaces, offering expertise in the niches they had cultivated in those years.

“You go to Hustle Cons, and you see these awesome founders talk and it was laying the blueprint in some ways,” said Ben Alexander, another former member of The Hustle’s sales team. “A lot of it was jumping into the unknown and riding the waves. So, when the acquisition happened, I thought, ‘Why not try to do our own thing?’”

Helping others build their best newsletter strategy

Morning Brew and The Hustle helped build the following blueprint for how to build an independent publication: 

• Start with a clear audience and topic in mind.
• Launch first with a newsletter.
• Scale the audience using content, paid ads, and word-of-mouth.
• Monetize with native ads.

Look around today’s newsletter landscape, and you’ll see lots of copycats. You’ll find newsletters that mimic the design and tone of Morning Brew that cover daily news in Brazil (The News), Southeast Asian tech (Backscoop), and Canadian business news (The Peak, which launched in 2020 and sold in 2023 for $3.75 million). There’s even a Morning Brew-like newsletter built specifically for Canadian dentists, called Morning Floss. (14,000 dentists subscribe.)

Other newsletters don’t look anything like Morning Brew or The Hustle — but they still follow the playbook that these newsletters built. So it makes sense why their newsletter alumni would be so in demand: Who better to teach you the newsletter playbook than the people who created it?

Take the case of Denk. At Morning Brew, he created an in-house system for publishing newsletters that included growth tools, analytics, and ad management platforms. But he didn’t see an out-of-the-box email service provider that offered all of those tools to any newsletter operator, so he started his own company to fill that need. At Beehiiv, his team created a Morning Brew-like toolkit so any newsletter can benefit from “having an all-in-one ecosystem,” including the ability to turn on premium subscriptions, analyze subscribers based on their sign-up source, and run A/B tests. (Editor’s note: Beehiiv is a sponsor of Inbox Collective, but they had no involvement in the production of this story.)

For other newsletter creators, the challenge isn’t tooling — it’s figuring out the business side of things. So Rothenberg, the ex-director of growth at Morning Brew, fills that knowledge gap with her new venture, Smooth Media. “At Morning Brew, we really learned what comes with working with creative talent and how to best provide operations and strategy around it without diluting it so much that it becomes boring,” she said. Smooth Media — which she founded alongside fellow Morning Brew alumni Josh Kaplan and Kinsey Grant — helps creators build well-rounded media businesses by providing them with a revenue team, operational processes for products, and digital product management.

So many newsletters today are willing to spend money to grow their email lists, but buying ads yourself can be a confusing process. McGarry’s company, GrowLetter, provides this expertise to clients, who tend to be much smaller than The Hustle. “We’re working with people who have 50,000 or 100,000 subscribers and want to get to 1 million. So the learnings are very different,” McGarry said. But what’s remained the same is the opportunity to leverage platforms like Facebook to grow. “Paid social ads are still the best,” he said. “They were the best acquisition source at The Hustle, too.”

For other operators, the challenge is finding relevant brands to advertise in their newsletters. At MadRev, Huff and Alexander work to sell ad inventory on behalf of their roster of over 90 clients, which includes both direct-to-consumer and B2B brands, and newsletters that span lifestyle and fitness to marketing-focused niche publishers. They honed their approach to selling ads at The Hustle, and now bring that skillset to a variety of independent operators. The pitch for advertisers hasn’t changed much from their Hustle days. “Newsletters are really straightforward and good for demand generation or acquisition,” said Huff. “For marketers, that can be a nice and simple measurement.” 

What’s next for newsletters?

The alumni I interviewed are well aware of the radical transformation the newsletter industry has experienced in a few short years. Sites that just a few years ago had predicted the demise of email now tout the “newsletter boom.” 

What is undeniable is the sheer number of newsletters that exist now. Many agreed that the glut created new challenges for anyone trying to build their newsletter approach. Strategies like affiliate marketing and co-registration are not as effective as they once were. Paid social ads, though still effective, are more competitive — and a lot more expensive than before. (In the early days of Morning Brew or The Hustle, an email subscriber might be acquired for less than $0.25. Many large brands currently spend anywhere from $1 to $3 per email subscriber.) Referral networks have been a big part of the success story for newsletters in 2023, but breaking through the noise is hard if you don’t already have an audience.

Rothenberg said, “we barely tweeted or even had an Instagram presence back then because it didn’t get us newsletter subscribers, so why would we do it? Whereas now, anyone with a newsletter needs to have a presence on what we call an algorithmic feed, whether it’s YouTube Shorts or TikTok.” At Smooth Media, her team provides strategic guidance and business operations to creators who are becoming more and more their own mini-media companies.

Nevertheless, there are still some truisms that remain. Great content is still king, but it needs to reign over a very specific kingdom. Not all subscribers are created equal, as Denk pointed out several times throughout our interview, and what newsletters should aim for is engagement, not just growth. “The ones that are really winning are picking a lane,” he said. “That’s where we’ve seen the steadiest success, in not trying to appeal to the masses but to really specialize on specific audiences and excel there.”

What about best practices for selling ads? For Huff, the rules haven’t changed much at all. “The Hustle taught me that, at the end of the day, people want to see results when it comes to newsletters,” she said. “Sometimes it’s nice to run an ad for brand awareness, but that’s not always the metric that is measured or cared about.” 

Another evergreen practice? Building relationships. The alumni have maintained strong ties with each other and frequently collaborate now that they have their own ventures. Their Morning Brew and Hustle pedigrees helped them get their first clients and several credit word-of-mouth with their steady growth. However, they stress that networking is a powerful tool regardless of the size of your newsletter.

“You can create that network through collaborations,” McGarry said. At GrowLetter, he helps media companies and creators get more subscribers through a variety of strategies. “Collaborations can mean a lot of things: swapping ads in your newsletter, supporting each other’s posts on social media. It doesn’t have to be transactional. You just want to find people who you’re friends with, who you vibe with, and whose content is helpful to your audience and vice versa. Through that, you build friendships.”

Plus, there are some advantages to the newsletter landscape today. Many of the biggest email platforms now make it easy to gain income through your work, whether it’s through selling subscriptions, ads, or products directly to your audience. Readers also look to creators they can trust to inform them of a topic that may be overlooked or completely ignored by traditional media outlets. After all, what brought millions of readers to Morning Brew or The Hustle is a relatable, irreverent-yet-informative style that fulfilled a need for a new type of professional. In other words, being distinctly yourself is always appealing.

Or, as Huff said when I asked about what she sees as the future of newsletters: “As long as you’re starting a newsletter true to your personality and written in your voice, I think you have a chance of success.”

Thanks to our sponsor

The stories you’re reading on inboxcollective.com are made possible thanks to the generous support of our fall sponsor, Who Sponsors Stuff, which gives you and your team the tools to quickly find and reach out to relevant sponsors for your newsletter. They track 350+ newsletters, have direct contact information for 6,000+ sponsors, and keep you on the cutting edge of who’s spending money in the email advertising space. Find out how their Sales Pro product can supercharge your ad sales operation today.