Leap Academy with Ilana Golan
The Reinvention Queen: Guy Kawasaki Interviews Ilana Golan on Leaping Across Careers
11 Dec 2025
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: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training
No persons identified in this episode.
This episode hasn't been transcribed yet
Help us prioritize this episode for transcription by upvoting it.
Popular episodes get transcribed faster
Other episodes from Leap Academy with Ilana Golan
Transcribed and ready to explore now
Gretchen Carlson: The Journalist Who Defied Fox News and Exposed Workplace Abuse | E110
03 Jun 2025
Leap Academy with Ilana Golan
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
29 May 2025
Leap Academy with Ilana Golan
Breaking the Glass Ceiling: How Adva Amir Became One of the Few Female Airline Captains | E108
27 May 2025
Leap Academy with Ilana Golan
From School Teacher to Fitness Icon: What I Wish I Knew Before Quitting My Job | Brian Keane | E107
22 May 2025
Leap Academy with Ilana Golan
Tony Khan: Building AEW into a Billion-Dollar Brand and Competing with Wrestling Giants | E106
20 May 2025
Leap Academy with Ilana Golan
Tim Storey: Turning Setbacks Into Comebacks and Achieving Unstoppable Success | E105
15 May 2025
Leap Academy with Ilana Golan