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.”