The Idea:
In February 2021, HubSpot bought The Hustle in a deal worth roughly $27 million, and Adam Ryan was sitting in the president's chair. He'd joined in August 2016, four months after launch, as a part-time ad salesman.
Five years of selling newsletter ads had taught him two things. Great writers drove almost every metric a media company cared about, yet content teams were among the worst-funded departments. And B2B content was broken. The useful stuff lived in white papers or behind trade paywalls, and in Ryan's view it was dull because it was written by people who had never done the jobs they wrote about.
He'd also seen what bad money does. Earlier in his career at Spiceworks, an IT professionals' network, he watched a company that made plenty of money raise more than it needed and make poor long-term decisions as a result. Great company, bad cap table.
So Ryan sat down with fellow Hustle exec Becca Sherman, who lived about eight minutes away. The bet: find practitioners, give them a salary and benefits, and handle everything else.
This was the beginning of Workweek.
The Execution:
- November 2021: Workweek launched with $1.5M led by LightShed Ventures, 10 full-time staff including four creators, and verticals spanning healthcare, cannabis and fintech. Creators got a salary and full-time benefits, not a revenue share and a login.
- 2022: The sprint. Healthcare consultant Blake Madden joined as a full-time creator in February and launched Hospitalogy in April. Workweek added a new creator every three weeks for five months. Total seed funding reached $7M.
- July 2022: Workweek had 19 creators and close to 250,000 subscriptions, nearly half of them bought at around $10 per subscriber. The Marketing Millennials gained 7,000 subscribers organically in seven weeks while paid acquisition added 20,000.
- November 2023: The cull. Ryan narrowed the company's focus, dropping underperforming creators until only eight remained. Media analyst Jacob Cohen Donnelly had criticised Workweek at launch for spreading itself too thin with no real benefits of scale.
- June 2024: A $12.5M Series A led by Next Coast Ventures funded a professional networking platform for its 500,000+ subscribers across eight newsletters. Headcount had grown from 10 to 49. Ryan said 35% of revenuethe previous year came from non-ad sources.
- August 2026: A further $17M from Next Coast and Aperiam took total funding to $36.5M. Revenue is north of $20M, and the company is not profitable. Its roughly 150,000 audience members each have to apply and be vetted, and Workweek has identified about 81% of subscribers down to the company they work for.
- The payoff for creators: Ryan says Workweek creators see CPMs up to five times the industry average, around $75 for some newsletters, and two top creators bring in over seven figures a year.
- Today: Workweek has flipped from media company to platform. Members of its five gated networks can now launch their own newsletters, with the ad network opening in stages and reaching general availability in early 2027. 35 new newsletters are ready to go. The catch: The Rebooting's Brian Morrissey warns that $36.5M raised means Workweek now needs a substantial exit to justify it.
The lesson?
In 2022, Workweek was buying readers at $10 a head and adding a creator every three weeks. It hit half a million subscribers and 19 creators, and it was spread too thin. The fix wasn't more. It was fewer creators, a gated audience it could identify down to the employer, and ad rates five times the market. The founder who once warned about "bad cap tables" now has $36.5M to justify, so the story isn't finished. But the core bet has already paid off: in B2B, the audience you can name beats the audience you can count.