Meet the guy who’s shaping HubSpot’s media strategy

The SaaS company bought the business newsletter The Hustle in 2021, and Brad Wolverton is in charge of driving synergies between the two.

Welcome! I'm Simon Owens and this is my media newsletter. You can subscribe by clicking on this handy little button:

The last few years have witnessed a flurry of acquisition activity for digital news startups, most of which were swallowed up by larger media conglomerates. We had Insider’s acquisition of Morning Brew, Axel Springer’s acquisition of both Insider and Politico, Cox Communications’ acquisition of Axios, and The New York Times’ acquisition of The Athletic, among others. In each of those cases, the parent company aimed to extend its reach into new regions and content niches by simply buying up already-existing audiences. 

But The Hustle’s 2021 acquisition was a bit more of a head scratcher. The irreverent business newsletter was bought for a reported $17.2 million by HubSpot, the tech company that produces everything from CRM to email marketing to CMS software. Why was a SaaS company — operating in an industry sector that typically trades at many multiples of revenue — interested in a media outlet that was generating a tiny fraction of its yearly earnings?

As it turns out, HubSpot wasn’t interested in The Hustle’s existing business lines, which mostly consisted of direct-sold native advertising. Instead, the move was aimed at lowering customer acquisition costs. “We believe that the next generation of software companies will invest in media that earns the attention of their audience,” wrote HubSpot’s then-SVP of marketing Kieran Flanagan after the sale closed. “Instead of the traditional model of having a software company embedded inside of a media company, we predict that the next generation of tech companies will have the opposite — a media company embedded inside a software company.”

At the time, HubSpot was already generating millions of monthly visits from its marketing blog, but it mostly consisted of the kind of how-to articles that perform well in search engines. The Hustle, on the other hand, produces content geared toward daily, habitual reading. As Flanagan further explained, it offered a branding opportunity for HubSpot’s services:

Today, B2B brands can be a daily part of their customers' lives before they even use their product. They can become a daily source of education and information for their customers. They can grow a large audience for that content by creating it for the people who buy their product and the many more who will use it. They can earn the attention of their audience by continually creating value for them.

HubSpot isn’t the first non-media company to dabble in news content, and other similar experiments have seen mixed results. MEL Magazine, for instance, was funded for years by Dollar Shave Club, only to be shuttered when it couldn’t generate sustainable revenue. The venture capital firm a16z recently ceased publication of Future, the online outlet that was supposed to compete with the traditional tech press.

So how is HubSpot avoiding their fate? To answer that question, I turned to Brad Wolverton, the company’s senior director of content. Wolverton came in through the Hustle acquisition and now runs much of the company’s content slate. In a recent interview he told me about his circuitous journey to The Hustle, his buildout of a paid subscription service, the synergies between the two companies, and HubSpot’s recent forays into the Creator Economy.

Let’s jump into it…

How he ended up at The Hustle

Wolverton was actually among the first employees at The Hustle who had a traditional journalism background. Sam Parr, the company’s founder, famously spun the newsletter out of an event he ran called Hustlecon, and in a 2018 podcast interview he told me that he sought out non-journalists to write for it. “The majority of people we hired don’t have traditional media experience, and that’s very much on purpose,” he said. “It’s because when we started, it was me just blogging. I’m a self-taught blogger, and I don’t have a traditional education on it.”

Wolverton came on a few months after that podcast interview. He got his start at an Atlanta business magazine, and over the next several years he worked his way up in the industry, writing for outlets like BusinessWeek and The New York Times. He eventually landed at The Chronicle of Higher Education, which he described to me as “probably one of the best jobs I've ever had.” There, he covered the business of higher education, with an emphasis on college sports.

Wolverton’s first taste of non-traditional media came in 2016, when he was hired on as an investigative reporter at NerdWallet. That company specializes in recommending various financial products to its users, taking a cut of revenue whenever those users sign up for a recommended service. Prior to Wolverton’s hiring, it had specialized in how-to advice content for people who were conducting research for things like getting a new credit card or refinancing their mortgage. “I was part of a four-person investigative reporting team that covered wrongdoing in consumer finance,” he explained. “It was the sort of effort that they put in place to really deepen their relationship with consumers outside of just one-off searches that people would make on the internet.” 

He worked there for over two years, but while he was proud of the work his team published — it won a National Press Club award in 2018 — NerdWallet ultimately ended up shutting down its investigations unit, apparently because it couldn’t tie it to a tangible ROI. Wolverton had enjoyed working outside the rigid confines of traditional media, and so when his former boss introduced him to Sam Parr, he jumped at the opportunity to join a startup that was rewriting the media playbook. 

By that point, Parr had grown The Hustle’s email list to over a half million readers, and he was looking to bring in people who could help take the business to the next level. “I was the head of content, and I thought I would maybe get to be kind of a player coach, because I had mostly enjoyed the writing side of journalism throughout my career,” said Wolverton. “But it became apparent to me that one of the big things that we needed to do was diversify our revenue streams.” At the time, The Hustle was monetized entirely through native advertising in the newsletter. “It was a good business. It brought us about $10 million a year, but we knew that with the whims of the marketing world and the economy, we needed to have another leg to stand on.” 

So Wolverton shifted his focus toward building out The Hustle’s next business model: a paid subscription product.

Launching Trends

Part of what makes The Hustle so appealing is how it takes the most important business news of the day and summarizes it in a breezy, conversational style. “We call it the Jon Stewart effect,” Parr told me in our 2018 interview, “where we won’t necessarily break the news, but we’ll give you an interesting angle on it that you hadn’t heard before.”

But because the newsletter isn’t breaking news — or performing much in the way of original reporting for that matter — it doesn’t lend itself to paid subscriptions. Wolverton knew he couldn’t pull it behind a paywall or simply offer up extra newsletters and expect the audience to take out their credit cards. He needed to come up with a truly differentiated product that offered real value.

The service his team ultimately launched was called Trends, and it looked nothing like The Hustle. Instead, they developed more of a research product, similar to the high-priced reports regularly put out by companies like Gartner and Forrester. “A lot of our reports at first were like these long 3,000, 4,000 word documents on the state of industries,” said Wolverton. “And then what we learned was that people don't read long reports. I mean, they might click on them, but the time on the page was not that long. So you knew that they weren't spending that much time with it. So we experimented with shorter, smarter versions of it.”

Now, the Trends reports are around 1,500 words and heavily supplemented with graphics. They usually pinpoint an emerging, undervalued industry and then provide a sort of starter kit for launching a business in that industry. Here’s a sampling of recent topics:

1. The Senior Living Space Is Ripe for Disruption

2. Beauty Brands Are Barely Scratching the Surface on These Search Terms

3. This Below-the-Radar Niche Is Self Storage’s Hotter Cousin

But the real crown jewel of the Trends subscription — and a major reason for why its 15,000 subscribers cough up $300 a year for it — is its private Facebook group. Upon joining it, you’re hit with an automatic questionnaire that asks, among other things, which email address is associated with your Trends account. A Trends employee then vets every applicant, rejecting those who don’t have a corresponding subscription.

So what’s so great about this group? “It's morphed into this amazing community for entrepreneurs,” explained Wolverton. “I think it's probably the coolest thing on the internet if you want to start or grow a business.” Many members are running their businesses as part-time side hustles, but there are also plenty of veterans in the group who have built more mature companies. “You can get in there and search for what people have talked about in the past, but there's like 15,000 people in there now who are active and who learn from each other every day.”

Wolverton gave me access to the group so I could observe these interactions myself. Most of the posts I came across performed some type of crowdsourcing. In some cases, they were asking very specific questions around various tools and services. One woman, for instance, posted about a lead-generation tool called Bark and asked if anyone else had any experience with it. Several people piped up to say they wouldn’t recommend the service:

Other posts contained open calls for networking and collaboration partners.

As the group grew, the Trends team began engaging in its own form of crowdsourcing by using information shared in the group for its own research reports. “We’ll take the best comments or the best insights, and we turn some of those things into more fleshed-out pieces,” said Wolverton. “The genesis of a lot of our ideas comes from that community.”

Finding synergies between The Hustle and HubSpot

Up until February 2021, The Hustle operated mostly as a traditional media company, in that it was funded primarily through advertising and subscriptions, but soon after the HubSpot acquisition went through it did away completely with outside advertising. 

Instead, The Hustle’s main contribution to HubSpot’s bottom line is its ability to act as the very top of a sales funnel for the company’s core products. A recent issue, for instance, encourages readers to download HubSpot’s free templates for developing new skills. In order to download those templates, you must first enter your name, email address, and phone number. Presumably, this will place you on some sort of marketing list that will blast out more overt pitches for HubSpot’s tools.

But for the most part, the newsletter has stayed the same, and Wolverton told me that HubSpot’s leadership hasn’t interfered with its secret sauce. “When my team was brought over in this acquisition, we had four people on the editorial team, and by a year in we had about 12 to 15 people. So they gave us a lot of opportunities to hire more people, deepen our bench, and build new products.”

I was curious as to why the company decided to keep Trends running post-acquisition. With 15,000 members paying $300 a year, it’s generating around $4.5 million — certainly impressive for a digital media company, but a drop in the bucket compared to its $1.6 billion in annual revenue. “Because [Trends] aligns so closely with their customer base — which is a business owner and operator — I think it has a huge upside for HubSpot,” Wolverton said. After the acquisition, there were brief discussions about opening the Facebook community up to everyone, but they determined that such a move would devalue the group. The $300 paywall, in other words, serves as a quality filter, ensuring that all members are serious entrepreneurs, and therefore much more likely to convert into HubSpot customers further down the line.

Entering the Creator Economy

So how serious is HubSpot about growing its media arm, really? As I mentioned above, it’s not uncommon for tech companies to dabble in the sector, only to abandon it when synergies fail to materialize. Both AT&T and Verizon, for instance, spent billions of dollars on media properties and then dumped them at significant losses. Is HubSpot really the exception to the rule?

It just might be. In March 2022, it announced the launch of a creator program, claiming to invest millions of dollars on funding up-and-coming independent podcasters. “HubSpot Creators will launch with an initial cohort of eight podcast creators and will tap into the company’s firsthand experience in building media channels from scratch to help creators grow their brands with dedicated resources and networks,” the announcement read. “Over time, the program will aim to expand beyond just podcasts to include YouTube and newsletter creators as well.”

So what’s the strategy there? Wolverton explained that there are lots of talented podcasters who aren’t growing to their full potential because they don’t have any support, and HubSpot is acting almost in a quasi-venture capitalist role in helping them build their audience. “We're essentially paying them almost as if they’re part of our staff,” he said. “We’re licensing the podcast, and hopefully the two sides benefit in a way where the podcast gets bigger and we get a lot more people who have exposure to HubSpot.” In addition to a steady paycheck, members of the podcast network get production help and are regularly plugged into HubSpot’s marketing channels — including The Hustle.”

There are currently 35 shows listed on the HubSpot Podcast Network page, so it’s clear that the company hasn’t hesitated in doubling down on its media arm. Wolverton alluded to other products coming down the pipeline, including a Hustle newsletter spinoff focused specifically on marketing. He also began staffing up The Hustle’s YouTube channel, which has recently published animated explainers on topics like “Why Free Stuff Makes Us Irrational” and “The Economics Of The $2 Billion Christmas Tree Industry.” 

During our interview, I pointed out to Wolverton that HubSpot was a bit of an anomaly in its ability to actually find synergies between its media and tech properties. So how did it become the exception to the rule?

He credited HubSpot’s senior management, who acknowledged up front that they didn’t want to meddle with the very formula that made The Hustle so successful in the first place. “A lot of founders and people who run companies think that they know how to create content that's interesting, and so they end up interfering a little bit too much when it comes to acquiring a business that actually knows how to do media.” His bosses at HubSpot, on the other hand, didn’t bring that arrogance to the acquisition. “I think that the great thing about this company is that they've stayed out of our way.”

Do you like this newsletter?

Then you should subscribe here:

Simon Owens is a tech and media journalist living in Washington, DC. Follow him on Twitter, Facebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.