Episode 292. Building a portfolio career w/ Ilana Golan, Founder & CEO of Leap Academy
This episode of The Art of Entrepreneurship is for anyone who’s ever hit a wall in their career and wondered what it would take to rebuild something even bigger.
My guest is Ilana Golan, tech entrepreneur, performance coach, and founder of Leap Academy. Ilana and I discuss her journey from the Israeli Air Force to Silicon Valley, where she learned that the biggest cost in life isn’t what you spend—it’s the money (and potential) you’re not making.
We talk about what it really means to “detach the data from the drama,” how to move through career setbacks with grace, and why every high performer should be building a portfolio career instead of climbing a single corporate ladder. Ilana also explains how she turned one of the hardest moments of her life—being ousted from her own startup—into the foundation for Leap Academy.
Tune in for practical insights on getting leap-ready, recognizing self-imposed barriers, and creating a career that compounds over time.
⭐ Feeling inspired to take your next leap? Visit leapacademy.com for Ilana’s free Career 360 training and strategy session invitation.
About Ilana Golan
Ilana Golan is a tech entrepreneur, performance coach, and founder of Leap Academy—recognized by Inc. Magazine as one of the fastest-growing companies in the U.S. A former Israeli Air Force officer and Silicon Valley engineer, Ilana helps high performers elevate their leadership, build portfolio careers, grow their personal brands, and create meaningful impact on their own terms.
Connect with Ilana: Website | LinkedIn - Ilana Golan | LinkedIn - Leap Academy | Instagram | YouTube
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