Gary ‘Vee’ Vaynerchuk was born to be an entrepreneur. At six years old, he was already running a lemonade stand like a boss, later flipping baseball cards for cash. By age 14, he had made thousands when his father put him to work in the family liquor store for $2 an hour. He hated it, but years later, he rebranded the business and scaled it from $4 million to $60 million. Realizing he didn’t own a piece of it, Gary walked away with nothing and started over. Now, as the founder of multiple ventur...
Feb 06, 2025•46 min•Transcript available on Metacast Trent Shelton hit a low point after his NFL career ended, leaving him lost and questioning his purpose. Tragedy struck when his best friend, overwhelmed by his own struggles, took his life. The loss shook Trent to his core. Determined to honor his friend’s memory and empower others facing similar challenges, Trent picked up his phone and began sharing raw, heartfelt videos. These eventually evolved into RehabTime, a global movement helping millions turn pain into purpose. In this episode, Trent ...
Feb 04, 2025•39 min•Transcript available on Metacast John Graham went from being a shy, anxious kid to becoming a three-time USA Memory Champion and performing before 400 million viewers in China. Despite these achievements, John faced severe anxiety and daily panic attacks, which led him to confront and release suppressed emotions. Today, he has transformed his struggles into strength, helping others unlock their true potential. In this episode, John joins Ilana to share how he overcame severe anxiety through unconventional methods, the importanc...
Jan 30, 2025•50 min•Transcript available on Metacast After his parents’ divorce, Topaz Adizes discovered the power of connection through the camera. His drive to explore human connection led him to become a filmmaker. From filmmaking to his work with The Skin Deep, Topaz focuses on creating real, vulnerable conversations in a digital world. His viral documentary The And shows how shared space and honest dialogue can deepen relationships. In this episode, Topaz joins Ilana to discuss the art of asking questions that strengthen relationships and how...
Jan 28, 2025•58 min•Transcript available on Metacast 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, RSE Ventures, appeared as a guest investor on Shark Tank, and developed military drones for the U....
Jan 23, 2025•1 hr•Transcript available on Metacast 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 experience into a more personalized one. In this episode, Nick joins Ilana to share how he transformed...
Jan 21, 2025•55 min•Transcript available on Metacast 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 episode, Bill takes Ilana through his leadership philosophies and shares lessons on building relatio...
Jan 16, 2025•59 min•Transcript available on Metacast 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 history as SoftBank Investment Advisers’ first female partner. Now, as CEO of web3 startup Virtualness, s...
Jan 14, 2025•46 min•Transcript available on Metacast 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 founded Willow, a fintech company focused on making financial advice more accessible, especially for th...
Jan 09, 2025•47 min•Transcript available on Metacast 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 starting businesses to acquiring and turning underperforming ones into successes. Now, as the founder...
Jan 07, 2025•43 min•Transcript available on Metacast 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, "Why not me?" and continued challenging herself to achieve more. In this episode, Robin shares with...
Jan 02, 2025•40 min•Transcript available on Metacast 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 management. In this episode, Naveen talks with Ilana about the mindset that drives him to solve the wor...
Dec 31, 2024•56 min•Transcript available on Metacast 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-profile events for celebrities like George Clooney and Saturday Night Live. In this episode, Jeff shares h...
Dec 26, 2024•45 min•Transcript available on Metacast 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 platform that enables individuals to lend small amounts directly to entrepreneurs worldwide. In this epi...
Dec 24, 2024•32 min•Transcript available on Metacast 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 luxury vacation home co-ownership platform, launched just before the pandemic. Despite initial fears ab...
Dec 19, 2024•46 min•Transcript available on Metacast 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 millions to pursue something more meaningful. This gave rise to Quest Nutrition, a billion-dollar compan...
Dec 17, 2024•56 min•Transcript available on Metacast 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. Despite running a $300k monthly loss and receiving multiple life-changing acquisition offers, he rej...
Dec 12, 2024•51 min•Transcript available on Metacast 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 the multi-billion-dollar company, ClickFunnels. In this episode, Russell shares with Ilana how he tra...
Dec 10, 2024•53 min•Transcript available on Metacast 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 joins Ilana to discuss the importance of tackling challenging opportunities, the practices that lead ...
Dec 05, 2024•46 min•Transcript available on Metacast 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 it work, he bootstrapped and secured loans to launch a clinic in Silicon Valley. Today, Prenuvo is re...
Dec 03, 2024•46 min•Transcript available on Metacast 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 empathize with the “misbelievers.” In this episode, Dan joins Ilana to share his journey from personal...
Nov 28, 2024•50 min•Transcript available on Metacast 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 him to reevaluate his life’s purpose. He realized that his true calling is to serve and uplift others,...
Nov 26, 2024•52 min•Transcript available on Metacast 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 episode, Lisa talks to Ilana about setting ambitious goals, trusting your decisions, and finding self-wo...
Nov 21, 2024•1 hr 10 min•Transcript available on Metacast 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-dollar company that blends tech and creativity to reshape advertising. In this episode, David shares...
Nov 19, 2024•55 min•Transcript available on Metacast 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 this episode, Harley shares his incredible journey, highlighting key lessons on how entrepreneurship c...
Nov 14, 2024•55 min•Transcript available on Metacast 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, Virgin Atlantic was born. In this episode, Richard shares his incredible journey with Ilana, highlight...
Nov 12, 2024•21 min•Transcript available on Metacast 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 eventually grew into a national franchise. In this episode, Jeff talks to Ilana about spotting hidden...
Nov 05, 2024•48 min•Transcript available on Metacast 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 composting company. In this episode, Katrina shares how she turned a simple grad school project into a ...
Oct 29, 2024•45 min•Transcript available on Metacast 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, offering lessons on leveraging unique skills, taking bold risks, and building a values-driven team to bu...
Oct 22, 2024•50 min•Transcript available on Metacast Chris Voss excelled as a lead FBI international kidnapping negotiator. At the start of his career, he thought it was all about being tough and direct. But over time, he discovered the secret to cracking negotiations—tactical empathy. Today, he teaches business leaders how to read emotions, build trust, and avoid leaving money on the table. In this episode, Chris explains why empathy is a world-changing skill and shares tactics for getting what you want in business and life. Chris Voss is a forme...
Oct 15, 2024•43 min•Transcript available on Metacast 
