Kara Swisher built a three-decade career at The Washington Post and The Wall Street Journal covering Silicon Valley before deciding to strike out on her own. Speaking with Business Insider’s Dan DeFrancesco, she explained that she eventually felt she could build something more ambitious than what existing newsrooms offered, a realization that led her to launch the technology news outlet Recode in 2014.
From Reporter to Media Entrepreneur
Before founding Recode, Swisher had already helped create a conference series for the Journal that later evolved into the Code Conference. Since then, she has co-hosted the Pivot podcast with NYU Stern professor Scott Galloway, released a 2024 memoir on her decades observing tech founders, and built a following of roughly two million people across social platforms. She credited her comfort with risk—rooted in confidence in her reporting skills as a fallback—for making the leap easier than it was for many peers.
Knowing When Entrepreneurship Isn’t the Right Fit
Swisher said leaving a stable job only makes sense when someone has a distinctive perspective and genuine drive to create something new, not simply a desire to escape a 9-to-5. She noted that the strongest founders, in media or any industry, spot a gap audiences care about and build something that feels irreplaceable—a customer-first approach that guided her own transition into entrepreneurship.
At the same time, Swisher cautioned that entrepreneurship isn’t for everyone. She often advises people to stay in secure roles rather than force a path that doesn’t suit them, since building a business demands a high tolerance for uncertainty. While she believes most people can develop entrepreneurial instincts over time, she acknowledged that her own restlessness and skepticism of authority were traits she was simply born with.