How Hubspot built a massive newsletter and podcast audience
The SaaS company bought the business newsletter The Hustle in 2021, and Brad Wolverton is in charge of driving synergies between the two.
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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.
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