As soon as she hit Silicon Valley 25 years ago, veteran journalist and entrepreneur Kara Swisher rolled up her sleeves and got to work. She knows, and has taken to task, every tech titan: Jobs, Bezos, Musk, all the Marks (Benioff, Cuban, Zuckerberg), and also Vice President Kamala Harris, former Secretary of State Hillary Clinton, and so many more. How did she get here? In short: through confidence, decisiveness, and being unapologetically herself. Laurie and Kara talk through the personal qualities every CEO needs for maximum impact and success. They also discuss Kara’s 2024 memoir, Burn Book: A Tech Love Story, and walk through the key inflection points in Kara’s singular career.
Key Takeaways
- Generous Leadership: Early in her career, the esteemed tech journalist Walt Mossberg demonstrated remarkable generosity by sharing the spotlight with Kara, a gesture she describes as pivotal for her and something he did not have to do. This early experience profoundly influenced her own leadership style. Generosity in leadership not only attracts attention to your passions but also fosters meaningful connections. It doesn’t mean compromising the quality of your work or failing to hold others accountable; rather, it’s a powerful way to expand your network and impact.
- Lean into action. The value of time: Time is precious and limited, something Kara learned early when she lost her father at age five. This concept is a key driver for Kara when evaluating opportunities or what she wants to build next. If too many days go by where she is not excited about what she is working on, that is not a time to complain, it is a time to act and do something next.
- Confidence: Kara exudes confidence and always has. After being rejected from a job for being “too confident,” she famously retorted, “I am not too confident. I am fantastic, and if not, I will be.” Kara firmly believes that women should own who they are without apology.
- Leadership means learning: The best leaders are those that can take complex ideas and a lot of information and simplify. And the best leaders also learn. Kara knows every powerful person in tech and the BEST ones are those who continue to learn and not just listen to the echo chamber of their own ideas.
- Being Grounded: In an age flooded with information and a culture of maximalism, it’s easy to lose sight of what’s truly important. Yet, beneath the complexity lies simplicity. And knowing what is important, like family. Or what is important to you, for Kara is what she does. Is her best work already done? Absolutely not, it is still in front of her.
- Order the Duck: Kara knows exactly what she wants and isn’t afraid to ask for it. It frustrates her when others hesitate to do the same. Her advice is simple: if you look at a menu and want the duck, order the duck. Even if it’s not on the menu, ask for it anyway. There’s always a way to get the duck.
Supporting Resources
- Burn Book, A Tech Love Story, Kara Swisher, 2024
- Pivot, Podcast with Kara Swisher and Scott Galloway, Vox Media
- On with Kara Swisher, Podcast, Vox Media
- The Value of Simplicity , Jason Oeltjen, 2023
- Larger Scale Evolution of Leaders, Dennis Cook, 2020
- How to Bring Generosity to Your Leadership, Liz Kislik, 2024
- Being a Proactive Leader, Cheryl Robinson, 2024
- Foundations of Generous Leadership, Jay Steinfeld, 2022
