Kara Swisher on the Right Moment to Quit Your Job and Start a Business

Kara Swisher spent roughly three decades reporting on Silicon Valley for The Washington Post and The Wall Street Journal before deciding to build something of her own. Speaking with Business Insider’s Dan DeFrancesco, she explained that she eventually felt confident enough in her abilities to strike out independently, which led her to launch the technology news outlet Recode in 2014.

Comfort With Risk Sets Founders Apart

Before launching Recode, Swisher had already built a strong reputation in journalism, including helping create a conference series for the Journal that later evolved into the Code Conference. She told Business Insider staff that she handled uncertainty better than many of her peers when she made the leap, largely because she trusted her own reporting skills as a fallback. Swisher, who now co-hosts the Pivot podcast and wrote the 2024 memoir Burn Book, has since built an audience of two million followers across social platforms.

Not Every Career Needs an Entrepreneurial Leap

Swisher said the real test for going independent isn’t simply leaving a company or starting a newsletter — it’s having a perspective compelling enough that people choose your work over existing alternatives. She encourages aspiring founders to build around a genuine, unmet audience need rather than jumping ship for its own sake. At the same time, she acknowledged that entrepreneurship isn’t for everyone, noting that many people are better served staying in stable roles. Swisher described her own risk tolerance as tied to a restless personality, admitting she has always struggled with being an employee. Her advice for those considering the jump: weigh financial obligations and family responsibilities honestly before making the decision.