Leap Academy with Ilana Golan

Matt Higgins grew up in abject poverty, caring for his sick mother at just 9 years old. At age 16, he dropped out of high school to focus on financial growth, eventually earning his GED and getting into college. While balancing work, life, and caregiving, he lost his mother unexpectedly on the day he began a new job. Despite these challenges, among others, Matt co-founded a private investment firm...

It seemed like all was lost after Nicholas “Nick” Stone was cut from three different teams during his sports career. However, he used this setback to transition into finance, eventually founding Bluestone Lane, a successful coffee shop chain. Despite having never made coffee before, his love for the premium coffee culture of his home country, Australia, inspired him to transform the U.S. coffee ex...

After losing seven elections in college, Bill George realized that leadership is about building relationships and helping others grow. Personal losses, including the deaths of his mother and fiancée, taught him resilience and the value of purpose. Though on track to become CEO at Honeywell, Bill chose a more fulfilling path at Medtronic, focusing on the company’s mission to restore lives. In this...

Kirthiga Reddy’s legacy is built on bold decisions and breaking barriers. Defying cultural norms, she became a top engineering graduate in a society where her mother was denied an education. After moving to the U.S., her career soared, until she took a 40% pay cut to join a startup. That gamble led her to become Facebook’s first employee in India, scaling revenues to millions. She later made histo...

Despite her background in financial services, Lacy Garcia faced significant financial challenges after her marriage ended. She struggled with imposter syndrome, advising clients on finances while dealing with her own financial issues. Too embarrassed to seek help and unable to find the right advisors, Lacy turned her fear and discomfort into a drive for financial education and empowerment. She fou...

Neil Patel’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 by 16, he helped a client make $20M, marking the start of his career. After facing challenges with his earlier ventures, he shifted from s...

A former lawyer turned fitness powerhouse, Robin Arzón’s journey is one of resilience and inspiration. After surviving a traumatic hostage situation in college, she turned to running as a way to heal and challenge herself. She went from casual runs to completing marathons and ultra-marathons. Despite being diagnosed with Type 1 diabetes, Robin refused to let it define her. She embraced the mantra,...

Naveen Jain believes that no idea is too crazy to pursue. With the right questions and focus, you can turn big ideas into life-changing solutions. After his father's battle with stage 4 pancreatic cancer, Naveen wondered why early cancer detection wasn’t possible. This led him to apply his 'Why me? Why this? Why now?' framework, sparking innovation in early cancer detection and chronic disease man...

Jeff Krauss went from being a shy kid with no prior experience in event planning to a trusted name in celebrity event management. Despite facing setbacks, including financial struggles and failed ventures in nightlife, Jeff learned the ropes of event planning and built a reputation for trust and hospitality. Over time, he expanded his network by forging key relationships and organizing high-profil...

Jessica Jackley grew up with values of generosity and compassion, which inspired her passion for helping others. Initially uninterested in business, she had a life-changing moment after hearing Dr. Muhammad Yunus speak about microfinance. This led her to East Africa, where she saw firsthand how small loans helped entrepreneurs escape poverty. In 2005, Jessica co-founded Kiva, a groundbreaking plat...

Spencer Rascoff’s career is a masterclass in navigating crises. After co-founding the travel site Hotwire, the 9/11 tragedy devastated the travel industry. Spencer helped steer the company through this crisis, leading to its $685 million sale to Expedia. He then co-founded Zillow, guiding it through the 2008 housing crash and growing it to a $20 billion market cap. His third venture, Pacaso, a lux...

Tom Bilyeu’s journey is a powerful story of transformation, 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, Tom walked away from mill...

Chris Savage is a master at pivoting. He co-founded Wistia with his best friend in his living room, originally aiming to create an online filmmaking competition platform. When that didn’t work, they shifted to portfolio tools and later to secure video hosting for businesses, which became Wistia’s core offering. Chris wasn’t afraid to turn down major clients like HBO when their goals didn’t align....

At age 12, Russell Brunson was inspired to become an entrepreneur after watching an infomercial about making money. Over the years, he faced massive personal and professional setbacks, from losing 60% of his staff to battling infertility, financial struggles, and nearly going to jail. But instead of giving up, he turned each failure into a lesson, tweaking his approach and ultimately co-founding t...

Known for seizing “big, scary opportunities,” Bryan Power has defined his career by embracing risk, adapting to change, and staying focused under pressure. After turning down a promotion at Google for a new challenge at Square, he quickly realized he was in over his head. But it was in facing that discomfort head-on, that he experienced his most significant growth moments. In this episode, Bryan j...

Andrew Lacy stumbled into entrepreneurship after failing to land a tech job. His first company did so well that he eventually sold it to Disney. Believing he had business all figured out, he launched another company, only to realize that success wasn’t guaranteed. For his next venture, Prenuvo, Andrew took a more thoughtful approach, but investors repeatedly rejected the idea. Determined to make i...

Dan Ariely didn’t just accept the hand life dealt him. He turned it into something powerful. After a traumatic burn accident that scarred 70% of his body, he struggled to find his place in the world. This journey led him to study human psychology and behavior, focusing on how people cope with pain and trauma. Later, when false rumors spread about him on social media, Dan chose to understand and em...

Howard Behar went from making $300,000 a year to working at Starbucks for a third of that. Driven by his passion for the business, he rose to become president of Starbucks North America and later the founding president of Starbucks International, helping grow the company from 28 to over 15,000 stores worldwide. Despite these achievements, Howard faced a deep depression after retiring, prompting hi...

In a world that imposes expectations, Lisa Bilyeu is all about defying them. Raised in a traditional Greek Orthodox family, her path was set: get married and raise a family. But after eight years as a stay-at-home wife, she could no longer ignore the inner voice telling her she was meant for more. So, she co-founded Quest Nutrition with her husband and built a billion-dollar business. In this epis...

Convinced that technology was the future of advertising, David Jones set out to build Brandtech. But again and again, investors rejected his model, doubting the potential of AI and digital technology in an industry where traditional models worked so well. Despite countless ‘no’s,’ David pressed on, believing he could redefine the industry. And that's exactly what he did. Today, he leads a billion-...

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, eventually leading him to Shopify, where he became one of their first merchants and later, its president. In th...

From struggling in school because of his dyslexia to starting a magazine at just 15, Richard Branson has always found ways to turn his challenges into unique opportunities. Even his iconic airline started as a joke when he was stranded in Puerto Rico after his canceled flight. He hired a plane, wrote "Virgin Airlines" on a blackboard, and offered seats to other stranded passengers. Soon enough, Vi...

Jeff Dudan started his first business in college, painting apartments to pay the bills. The business grew beyond his expectations, allowing him to support his younger brother and create jobs for other college athletes. Years later, he moved to South Florida to help with disaster recovery after Hurricane Andrew struck. Having learned to see opportunity in adversity, he started AdvantaClean, which e...

One day, while watching her baby somersault, Katrina Spade thought about how quickly time flies. Then it hit her like a ton of bricks that she would be in her 70s by the time he turned 40. This reflection sparked an interest in the funeral industry, ultimately leading her to design a new death experience. Despite facing legal hurdles and industry challenges, she founded the world’s first human com...

Russ Ruffino spent his 30th birthday sobbing into his bourbon because he felt like a failure. He had spent the last decade bartending while clinging to his dream of becoming a movie star. So, how did he go from bartender to CEO of a $100 million business? He took his first step by applying his acting skills to writing persuasive sales copy. In this episode, Russ shares his incredible journey, offe...