Make Money by Building a Portfolio Career | Ilana Golan

Travis Makes Money

Ilana Golan is a serial entrepreneur, investor, and founder of Leap Academy—one of the fastest-growing professional education companies in America. With a track record that includes helping lead a $300 million exit, scaling a startup to $15 million in annual revenue, and raising nearly $1 million from top Silicon Valley investors, Ilana brings deep experience in both corporate and startup worlds. Her journey is defined by bold leaps, learning from failure, and empowering others to build careers with multiple streams of income and real fulfillment.

On this episode we talk about:

– Ilana’s first entrepreneurial hustle at age four—and her early lessons in value (and parental panic)

– The story behind raising $800,000 in weeks, only to be ousted by her co-founder and left with nothing

– How hitting rock bottom led to a period of personal and professional crisis—and the steps she took to rebuild her momentum

– The power of action over analysis: why doing—even when you don’t know what to do—creates clarity and new opportunities

– Redefining career success: the shift from a single-track “scripted” career to a dynamic, experimental “portfolio career”

– How Ilana built Leap Academy from a small experiment into a multi-million dollar business and top-charting podcast

– The importance of failure, resilience, and hunger in founders—and why she bets on entrepreneurs who’ve been through adversity

– Frameworks for evaluating new ventures, both as a founder and investor

– How Leap Academy helps mid-to-late career professionals reinvent themselves, build multiple income streams, and thrive in an ever-changing world

– The future of professional education, corporate partnerships, and the rise of coaching and community-driven learning

Top 3 Takeaways

1. Action Creates Clarity: When you don’t know what to do, start doing something—momentum and results follow action, not the other way around.

2. Portfolio Careers Are the Future: Building multiple streams of income and diverse professional experiences is the new path to wealth, fulfillment, and resilience.

3. Failure Fuels Growth: The best founders and leaders are those who’ve faced—and learned from—major setbacks, not just those with a string of successes.

Notable Quotes

– “The clarity came from the momentum, not just thinking about it or dreaming about it—the doing created the result.”

– “Look at your career as a series of experiments, not a single direction for the next 20 or 30 years. That takes all the fear away.”

– “The biggest cost is always the money we’re not making—the cost of inaction is higher than the cost of failure.”

Connect with Ilana Golan:

– Website: leapacademy.com

– Portfolio Careers: portfoliocareer.com

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