In the Room with Jessica Lessin
This week on The Room, we interview Jessica Lessin, founder of The Information. In Silicon Valley, whenever there is a breaking story, The source that founders, funders, and technologists turn to to get the inside scoop is the subscription-based news-source that Jessica founded in 2013. Jessica has created a platform the tech world can’t get enough of in a world crowded by media coverage and ad-blockers.
In today’s episode, we explore her path to disrupting journalism and how information is consumed in the tech world. We’ll explore insights and themes such as knowing what’s valuable and not giving it away, sustainable growth, and dealing with the hard stuff, like controversy. Listen to the episode here.
Listen on Spotify and Apple Podcasts.
Key Theme 1: Know what’s valuable, and don’t give it away!
Jessica walks us through her path to founder, which did not start out with a typical path. After graduating Harvard and covering faculty news at the Crimson, Jessica went on to institutional news outlets such as The Wall Street Journal. There, she covered the tech beat, mainly because she was the youngest in the room. Three years later, Jessica realized that no one was paying attention to something huge: the fact that the world was being fundamentally changed by tech. The biggest story of the moment needed a new platform. Even when digital news and media became increasingly crowded, she has been able to charge $399 for access to The Information. Jessica dives into why The Information charges for access and how she has been able to understand her reader and what they find valuable.
Key Theme 2: Growth & Sustainability
Unlike many Silicon Valley startup stories, Jessica has managed to build a multi-million dollar business without outside investment. In 2016, The Information reached profitability, a milestone some of the largest tech giants, have yet to crack. Jessica walks through her thinking around taking outside funding and how the company has grown over the past seven years. Jessica has progressively has grown her team and discusses tradeoffs in growing too quickly too soon. We get an inside peek at how her team has changed over the years and where she’s excited to see The Information grow next (hint: The world is getting smaller, and Silicon Valley is reaching farther).
Key Theme 3: Dealing with Controversy
As both an editor of a news publication and founder, Jessica has had to navigate breaking hard-hitting news stories as well as guiding her company through difficult times. The Information has broached industry-changing topics such as sexual harassment in venture capital, gender diversity and representation, management conflict, layoffs, IPOs, and acquisitions, to name a few. Jessica tells us about what it was like to launch a groundbreaking story as she was about to get on a long-haul flight, and then find out that The Information was being sued for the story as wifi was about to shut off. In these moments, Jessica reflected on what it takes to keep fighting for what you believe is right and being an even-keeled leader amidst turbulence. Jessica provides personal wisdom on keeping your head high, forging ahead, and grounding yourself in values even when it feels like a thankless job. Jessica’s anecdotes remind us that resilience is a consistent founder superpower.
For founders and funders everywhere, Jessica provides an inside look at what it means to disrupt an age-old industry and how to keep adapting to the changing environment and needs of your users. What time-old industry do you think needs disruption?
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