Leap Academy with Ilana Golan

Nathan Blecharczyk, co-founder of Airbnb, built his first software business as a teenager, earning nearly a million dollars before shutting it down to attend Harvard. Years later, Nathan and his roommates turned an air mattress idea into Airbnb, facing investor rejection, financial hardship, and moments when quitting seemed inevitable. From creating satirical cereal boxes to joining Y Combinator a...

After 12 years of working in corporate advertising, Case Kenny launched a podcast, New Mindset, Who Dis? as a personal experiment. In its first month, the show drew 57,000 downloads, yet Case kept it hidden, afraid it didn’t fit his professional image. Over time, he embraced his vulnerability, created bestselling guided journals, and built a brand helping millions live more optimistic and mindful...

What do you do when the dream you've chased no longer fits? For Julia Hartz, it meant walking away from a promising career in Hollywood to dive into the unknown world of startups. As an intern on the set of Friends, she learned the value of kindness, clarity, and high standards. But the real test came in tech, where she bootstrapped through a downturn, faced 27 VC rejections, and ultimately co-fou...

After getting laid off from his corporate job, Dan Shapiro launched his first startup, Photobucket Inc. (formerly Ontela), but faced nine months of rejection from investors and no funding. Despite these setbacks, his persistence led to a successful partnership, which later turned sour due to a managerial dispute. He took these lessons and went on to build multiple successful startups, including Gl...

Dr. Josh Axe’s passion for health and wellness began when his mother’s breast cancer diagnosis led to chronic health issues after chemotherapy. Inspired by this, Josh pursued natural medicine, which helped her make a remarkable recovery when cancer returned. Years later, Josh faced a spinal infection that left him unable to walk. Doctors predicted permanent disability, but using the same healing m...

Sahil Bloom was living the "dream" life, climbing the corporate ladder, earning well, and hitting all the career milestones. Yet, he felt unfulfilled. During a conversation with an old friend, he mentioned how he only saw his parents once a year. His friend's blunt remark, "You're going to see your parents 15 more times before they die," hit him hard, forcing him to reevaluate his priorities and r...

When Christiana Figueres was a young mother, she longed to share her love of nature with her daughters, a love sparked by watching golden toads shimmer like coins under the moonlight in a Costa Rican forest. Hoping to show them this rare beauty, she returned to the same park, only to learn that the species had gone extinct due to rising temperatures. That moment ignited her mission to leave a bett...

Being scrappy wasn’t just a choice for Gary ‘Vee’ Vaynerchuk; 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 emotional hurdles of entrepreneurship, he built his...

Matt Abrahams's passion for communication was shaped by his parents during his childhood. In the corporate world, he noticed that great ideas often went unheard because people were too anxious to speak up, particularly in high-pressure situations. Realizing that fear, not a lack of ideas, was the barrier to success, Matt made it his mission to help individuals overcome anxiety and communicate with...

As a teenager performing on New York’s streets and parks, Adam Met never imagined selling out arenas nationwide. Alongside his brothers Jack and Ryan, he formed the band AJR, playing for hours each summer while learning to capture the attention of indifferent passersby. A single tweet to Sia changed everything, launching their breakthrough. Balancing music with demanding academic work and nonprofi...

Kass and Mike Lazerow’s entrepreneurial journey began with a leap of faith and a lot of grit. They started Golf.com with funding from friends and family, only to be acquired by a company that later went bankrupt. Forced to raise capital and revive their business against all odds, they quickly learned that entrepreneurship means facing setbacks every day and building the resilience to keep going wh...

Bonnie Hammer’s passion for photography and storytelling led her to an internship on a TV production set, but instead of a glamorous role, her first job involved cleaning up dog poop. Despite these humble beginnings, Bonnie’s curiosity, strong work ethic, and willingness to tackle any task helped her rise through the ranks at NBC Universal, eventually becoming vice chairman and a powerhouse in the...

In 2016, former Fox News host Gretchen Carlson made a bold move that transformed the conversation around workplace harassment. After enduring years of mistreatment, she filed a lawsuit against Fox News Chairman Roger Ailes for sexual harassment. Despite the immense personal and professional risks, this courageous act helped spark the #MeToo movement, giving a voice to countless women who had suffe...

Tim O'Reilly’s entrepreneurial journey began with odd jobs like being a janitor, cemetery caretaker, and dishwasher. With just $500, he founded O'Reilly Media, initially focusing on publishing tech manuals. After a major setback during the dot-com bust, which saw revenue drop by $20 million, Tim continued building his business and creating a huge impact in the tech world. His work with Web 2.0 and...

As a curious eight-year-old, Adva Amir was mesmerized by the cockpit during a family trip, sparking a lifelong dream of becoming a pilot. After failing to become a military pilot in Israel, Adva felt broken. Shifting her mindset and picking up the pieces, she moved to the U.S. to pursue civilian flight training. Despite language barriers, naysayers, and grueling hours, she broke into this male-dom...

Brian Keane’s journey is a powerful example of embracing change and conquering fear. Originally a primary school teacher in London, Brian realized teaching wasn’t his true calling and made a bold leap into fitness, despite doubts from family and peers. With his mom’s support, he overcame numerous challenges to become a three-time bestselling author, certified strength and conditioning coach, and u...

Tony Khan was captivated by sports and wrestling from a young age. After immersing himself in sports analytics, he joined his father’s ventures, using his expertise to build a data-driven team at the Jacksonville Jaguars. Witnessing Fulham’s struggles, Tony saw an opportunity to apply his skills to improve the team and took it. His passion for wrestling ultimately led him to launch All Elite Wrest...

Tim Storey grew up facing financial struggles, family instability, and a devastating loss at a young age. When his father tragically passed away in a car accident, it could have broken him. Instead, Tim leaned on his family for support and drew strength from his faith and community. This resilience led him to become a life coach, eventually earning the title of "comeback coach" for stars like Robe...

Bernard Hampton’s journey from modest beginnings to Managing Director and The Head of The Academy at Bank of America is a testament to hard work, learning, and leadership. Raised in a middle-class family with a strong work ethic, Bernard’s early experiences shaped his leadership approach. From his start as a sales associate at RadioShack to leading over a thousand employees globally at Bank of Ame...

Mo Gawdat was thriving in his career as Chief Business Officer at Google X, enjoying wealth, success, and a loving family. However, his life took a dramatic turn after the tragic loss of his son, Ali. This loss made Mo realize that happiness isn’t defined by external factors but by how we perceive and navigate life’s challenges. Letting go of everything that once defined success, including his car...

James Currier was born an entrepreneur. Before turning 18, he had launched 18 businesses. After years in corporate jobs, he fully embraced his entrepreneurial calling. He co-founded Tickle, one of the internet’s first successful user-generated platforms, which grew to 150 million users before being acquired by Monster.com for $110 million. Now, as a founding partner at NFX, he invests in high-grow...

After studying law, Daniel Pink transitioned into politics, serving as the chief speechwriter for Vice President Al Gore. However, he soon felt unfulfilled and realized his true calling wasn’t in a structured career with defined rules, but in writing. Despite the uncertainty, he made the leap, leaving politics behind to pursue writing full-time. This decision led to multiple bestselling books, inc...

Dr. John Demartini’s childhood was marked by major obstacles, from a severe speech impediment and dyslexia to a rough start in school. Told that he would never read, write, or communicate, he defied the odds. At age 13, he left home and embarked on a journey that would take him from street life to a global career as a human behavior specialist and entrepreneur. In this episode, John joins Ilana to...

As a shy kid, Alex Carter struggled to speak up for herself. Her parents’ divorce sparked her interest in advocacy and mediation, which led her to pursue a law degree. Despite facing self-doubt early in her career, Alex bet on herself and built a career as a Columbia Law professor and renowned negotiation expert. Now, she helps others find their voice, advocate for themselves, and unlock career su...

Chemi Peres’s journey to success was shaped by both professional challenges and personal loss. After losing his job, he felt humiliated and vowed never to face such a setback again. He pivoted to venture capitalism, co-founding Pitango Venture Capital, Israel’s largest venture fund. Despite his success, Chemi experienced the profound losses of both his father and son. These tragedies fueled his dr...