Episode 4: Jessica Lessin of The Information

8 Dec 2020 · 33 min
Episode

8 Dec 2020 · 33 min

0:00

In this episode of The Room, hosts Claudia Laurie and Madison McIlwain interview Jessica Lessin, founder and CEO of The Information, a subscription‑first tech journalism outlet launched in 2013. Lessin recounts her path from Harvard student journalist to Wall Street Journal tech reporter, the moment she realized traditional media wasn’t serving the exploding tech sector, and why she decided to start her own publication. She explains the core philosophy behind The Information’s high‑priced subscription model—delivering differentiated, deeply sourced reporting that cannot be commoditized— and how the company built its own CMS/CRM stack, relied heavily on organic email acquisition, and experimented with paid channels while maintaining strict CPA and payback limits. The conversation covers the company’s early bootstrapped profitability in 2016, the gradual hiring of reporters, engineers, and senior business talent, and the strategic decision to stay privately owned without outside funding. Lessin also details editorial choices, notably the early coverage of sexual‑harassment allegations in venture capital, and how the team navigates criticism and legal threats. The interview touches on personal leadership challenges: managing a growing newsroom, maintaining a “thick skin,” and balancing demanding careers with co‑parenting two young children. Finally, she reflects on mentors who shaped her, the importance of women’s voices in media, and her broader involvement with nonprofit news. The episode offers insights into sustainable media entrepreneurship, content differentiation, growth tactics, and the human side of leading a high‑impact newsroom.

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