What happens when a fighter pilot’s discipline collides with Silicon Valley ambition?
In this powerful episode of Harder Than Life, Kelly Siegel sits down with Illana Golan—former F-16 fighter pilot, tech executive, and founder of Leap Academy—to unpack reinvention, adaptability, and fearless leadership.
Illana shares her journey from military service to Silicon Valley, the failure that reshaped her identity, and why adaptability is the most critical skill in the age of AI.
This episode explores leadership under pressure, portfolio careers, personal branding, and how to leap into your next chapter with clarity and confidence.
Key Takeaways
🟥 Adaptability is the new competitive advantage
🟥 Failure accelerates reinvention
🟥 Your brand is your career insurance
🟥 Clarity comes from action, not thinking
🟥 Reinvention is a lifelong skill
(0:00) - Intro
(1:19) - Early Life And Military Experience
(3:10) - Lessons in Leadership and Discipline
(4:46) - Challenges and Gender Equality In The Military
(10:32) - Transition to Tech And Entrepreneurship
(12:01) - Take On Israel's Current Events
(13:39) - The Importance of Failure and Reinvention
(18:28) - The LEAP Mindset
(21:54) - Checklist For Winning
(27:00) - Portfolio Career
(30:35) - Importance Of Adaptability Quotient
(33:34) - Reinvent Yourself
(35:39) - What A Unicorn Is
(38:00) - Advice For Feeling Stuck
(41:23) - Toxic Badges of Honor in Tech
(43:07) - Non-Tech Habits for Success
(44:14) - Lessons from Top Founders
(46:40) - Empowering Women In Tech
(47:58) - Rapid Fire Questions
(49:38) - Final Thoughts On Reinvention
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