Leap Academy with Ilana Golan

FREE scorecard from this episode: see how ready you are for your next leap in 90 seconds! Ambitious professionals: Melissa Arnoldi, EVP at AT&T Business, on bold leaps, staying curious, and how senior leaders really make decisions. Melissa leads 17,000 people and a $25 billion portfolio at AT&T. She took a title step down to join from Accenture, then led an international business across 11...

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 c...

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...

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 m...

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 ch...

We’re bringing back one of our favorite conversations from the Leap Academy podcast with digital marketing expert and entrepreneur Neil Patel. Neil’s story shows how hard work, persistence, and learning from failure lead to success. As a teenager, he started businesses, including building websites, but struggled with ineffective marketing agencies. This pushed him to learn digital marketing, and b...

Mike Fisher’s career has taken him from West Point and flying helicopters in the U.S. Army to leading technology teams at PayPal, serving as CTO of Etsy, and ultimately becoming CEO of MyFitnessPal. In this episode, Mike joins Ilana to unpack the leadership lessons behind that unconventional journey. He shares what the military taught him about giving feedback, building trust, and learning from mi...

Tom Cortese helped turn an idea that investors rejected hundreds of times into Peloton—an $8.1 billion public company that completely changed the way millions of people exercise. But his story isn’t just about building Peloton. It’s also about knowing when to walk away from something that has become part of your identity and having the courage to start again. In this episode, Tom joins Ilana to sh...

Sir Richard Harpin put £50,000 of his life savings into a business that nearly collapsed—twice. That company eventually became HomeServe, serving millions of customers globally before being sold for more than £4 billion. In this episode, Richard joins Ilana to share the lessons behind that extraordinary journey, from finding the business model that saved HomeServe with his final £10,000 to learnin...

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 com...

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 e...

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 t...

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...

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 breakthrou...

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...

Revisiting one of our most-downloaded episodes, Tom Bilyeu shares his powerful journey from self-doubt to self-mastery. His early years were shaped by fear of failure, a lack of direction, and doubts from those around him. After struggling to break into the film industry, he joined a startup with the goal of getting rich, but found himself unhappy and in a strained marriage. Taking a leap of faith...

In one of our most popular episodes, Amy Porterfield had a dream job working with Tony Robbins, one of the world’s top motivational speakers and business strategists. But deep down, she wanted to be her own boss. During a high-level meeting, she realized she was on the wrong side of the table, watching entrepreneurs build wealth instead of becoming one. With no plan, no clients, and no backup, she...

On our most replayed episode, Gary ‘Vee’ Vaynerchuk talks about how being scrappy wasn’t just a choice for him; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia. Overcoming the financial, mental, and e...

As a kid struggling with ADHD and financial instability, David watched his family nearly lose their home before taking a door-to-door sales job as a broke college student. He was terrible at it at first, but instead of quitting, he became obsessed with learning sales, systems, and business psychology. That mindset helped him build and sell four companies, scale across 5,000 cities in 34 states, an...

Mark Tluszcz had the career most people would chase: a top consulting job, rapid success, and a clear path forward. But eight years in, he made a move very few would dare to make. He left his high-paying job to start his own firm, faced hundreds of rejections while raising capital, and built Mangrove Capital from scratch. That same contrarian mindset led him to back companies others overlooked, be...

John Paul DeJoria grew up with no connections, no money, and no roadmap. He sold encyclopedias door-to-door despite constant rejection, got fired from three consecutive jobs, and lived out of his car while raising his young son. Then, with just $700, he launched John Paul Mitchell Systems and built it into a billion-dollar haircare company. That same relentless spirit later helped him turn Patrón...

Despite his high intelligence, George Barrios nearly flunked out of both high school and college, drifting without discipline or direction. Realizing talent alone wouldn’t build the future he wanted, he cleaned up his act, became obsessive about preparation, and built a reputation for solving hard problems others avoided. That approach helped him rise through HBO and Time Warner before transformin...

When Eric Ries built his first startup, he believed he had the perfect plan. But when no customers showed up, the business collapsed, exposing a costly truth: being certain does not make you right. That failure forced him to rethink his assumptions and ultimately led him to develop the Lean Startup method, a new way of building companies grounded in testing, learning, and truth. In this episode, E...

Jason Feifer started his career writing about middle school dances at a tiny local newspaper, frustrated and convinced he was capable of more. Stuck in a role that wasn’t moving him forward, he quit, sat in his dumpy apartment next to a graveyard, and began cold-pitching major publications with no connections. That decision transformed his trajectory, eventually leading him to become Editor-in-Chi...

Tim Draper didn’t become a legendary investor with billions in his account overnight; he started by taking a $6 million loan to launch his first venture fund, knowing failure was a real possibility. That decision didn’t just shape his career; it laid the foundation for backing some of the biggest companies in the world, including Hotmail, Skype, Tesla, and more. In this episode, Tim joins Ilana to...