The Reinvention Queen: Guy Kawasaki Interviews Ilana Golan on Leaping Across Careers

Ilana Golan has reinvented herself more times than most people switch job titles. From becoming one of the first women to train F-16 pilots in the Israeli Air Force, to engineering, to product, to Silicon Valley executive, to investor, to founder, she’s rebuilt her identity again and again in industries that weren’t built for people like her. In this episode of the Remarkable People podcast, Guy Kawasaki pulls back the curtain on what it really took for Ilana to leap across careers, break barriers, and build a system that helps thousands do the same. She breaks down the concept of reinvention and what it really takes to leap again and again.

Ilana Golan is a former F-16 flight instructor turned Silicon Valley tech executive and investor. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom.

In this episode, Guy and Ilana will discuss:

(00:00) Introduction 

(02:20) Breaking Barriers in the Israeli Air Force

(06:07) What Reinvention Really Means Today

(10:40) The Core Steps to Reinventing Your Career

(12:59) Reinventing When Systems are Against You

(15:16) Advice for Women on Breaking Glass Ceilings

(19:58) The Core Signals That You Need Reinvention

(21:52) Case Studies: Reinventing Public Figures

(29:37) The Role of Timing in Reinvention

(33:41) The Power of Building a Personal Brand

Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies.

Connect with Ilana: 

Ilana’s Website: leapacademy.com 

Ilana’s LinkedIn: linkedin.com/in/ilanagolan 

Resources Mentioned:

Guy’s Podcast, Remarkable People: https://podcasts.apple.com/us/podcast/guy-kawasakis-remarkable-people/id1483081827 

LEAP E97 with Guy Kawasaki: https://podcasts.apple.com/us/podcast/guy-kawasaki-the-tech-evangelist-who-built-apple/id1701718200?i=1000703853865 

Leap Academy:

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📍 San Jose, CA

📅 Feb 26–28, 2025

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