Leap Academy with Ilana Golan
Leap Academy with Ilana Golan is a podcast for ambitious professionals who know they're capable of more and want their next move to be bigger, whether that's a C-suite role, a board seat, an advisory role or a portfolio career. Every week, Ilana talks with founders, CEOs and executives about the leap that changed their career, what pushed them to make it and how they made it work. Guests have included Shopify President Harley Finkelstein, Peloton co-founder Tom Cortese, Richard Branson and Gary Vaynerchuk. Ilana is a tech executive, entrepreneur, board director and investor in more than 100 companies, and she won Startup of the Year in 2023. She asks her guests about moves she has made herself. New episodes every Tuesday.
Episodes
Communication skills and sales pitching: Dr. Forbes Riley explains how a painful, isolated childhood gave her the instincts behind $2.5 billion in sales.
Fitted with braces, headgear, and a tongue thruster for eight years, Forbes had no friends and communicated by writing and pointing. Television became her only window to human connection, and that solitary study built a pitch instinct she later carried into nearly 200 infom...
Founders and executives: Stacy Brown-Philpot traces her path from Detroit to Google, TaskRabbit CEO, and a $172M debut venture fund.
Stacy spent nearly a decade at Google, growing from a 14-person team to leading over 1,000 people in India. She later became CEO of TaskRabbit and sold it to IKEA after launching it into four new countries.
To build Cherryrock Capital, she met 366 investors over two years and closed 83 o...
This episode is dedicated to food creators and entrepreneurs: how Carleigh Bodrug built PlantYou into a bestselling cookbook brand while privately grieving her mother's lung cancer death.
Carleigh grew PlantYou to 13 million followers while filming recipe videos from chemo waiting rooms. She signed her second book deal two weeks before her mom's diagnosis and kept the ordeal off social media.
Her debut cookbook sold o...
We’re bringing back one of our favorite conversations from the Leap Academy podcast with Shopify President Harley Finkelstein. Harley Finkelstein didn’t set out to be an entrepreneur. He had no choice. With his father out of the picture, he had to pay for university and support his mother and sisters. So, he turned to his go-to problem-solving tool: entrepreneurship. Starting a t-shirt business changed his life, eventua...
At 18 years old, Shawn Nelson had a crazy idea: build a beanbag so massive it could fill an entire room. That idea eventually became Lovesac, a publicly traded furniture company and major consumer brand. In this episode, Shawn joins Ilana to share the real journey behind building Lovesac, from taking risks and learning as he went to winning Richard Branson’s The Rebel Billionaire and leading a company at scale. They also dive...
Manu Sai Bakshi arrived in New York with $2,500, a new wife, and a degree that wasn’t recognized in the U.S. Within weeks, he was applying for a job at Macy’s in Herald Square. That humbling beginning eventually led Manu into the hedge fund world, where he spent nearly a decade learning how the industry identifies and hires elite talent before launching Preeminence Advisors during COVID. In this episode, Manu joins Ilan...
Ilana Golan knows what it feels like to lose everything. After climbing from the Air Force to Intel to VP in a Silicon Valley startup, she thought she had made it. But when a trusted co-founder cut her out of their new business overnight, she was left with nothing. No job, no company, no income, and a shattered ego. That collapse became the turning point, forcing Ilana to ask who she was without the titles and what kind of life she...
Christina Tosi didn’t have a clear five-year plan when she graduated from college. She tried different majors, worked odd jobs, and kept searching for the thing that felt like hers. Baking became the answer she could not ignore. With relentless persistence, she went from a hostess stand to New York restaurant kitchens, proving herself one dessert at a time. That same drive eventually turned a tiny laundromat space into Milk B...
What does it really take to solve impossible problems? In this episode of Leap Academy with Ilana Golan, Ilana sits down with Astro Teller, CEO of Google X (Alphabet's Moonshot Factory), to uncover the mindset, leadership principles, and innovation frameworks behind some of the world's most groundbreaking technologies—including Waymo, Wing, and Google Brain. Astro shares why the biggest breakthroughs begin with embracing fail...
At 16, his grandmother fled Kraków after the Nazis killed her father, worked a New York factory floor beside her mother, and applied to every medical school in the state three years running before one finally said yes — then told her second-grade grandson that education is the only thing nobody can ever take away from him.Years later, David Rogier quit his venture capital job with no idea what he wanted to build, and his boss...
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