Leap Academy with Ilana Golan
The Leap Academy Podcast with Ilana Golan features honest and inspiring conversations about what it takes to leap toward bigger things, amazing careers, and the life you want. Ilana talks with influential people, experts, and thinkers who have built incredible careers and made a significant impact. Together they explore untold truths, emotions, and important lessons that enabled these guests to reinvent themselves and leap. The show offers concrete guidance on career leaps, including fast-tracking to leadership, jumping into entrepreneurship, building a personal brand, and creating a portfolio career.
Episodes
The Remarkable Story of Stacy Brown-Philpot Outgrowing Her Circumstances | Ep. 174
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 ye
The Emotional Story of Carleigh Bodrug’s EXPLOSIVE PlantYou Success | Ep. 173
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 me
Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | EP53
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
Neil Patel: From Crushing Failures to Building a Global Marketing Empire | EP62
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
CEO of MyFitnessPal Mike Fisher: He Applied for 1 Job, Then Became CEO | EP172
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 m
Peloton Co-Founder Tom Cortese: Building an $8.1B Brand & Knowing When to Walk Away | EP171
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 sha
Sir Richard Harpin: How He Turned £50K Into a £4 Billion Business | EP170
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 learni
Lovesac Founder Shawn Nelson: The Entrepreneurial Mindset That Built a Billion-Dollar Brand | EP169
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: From Starting Over to Recruiting Wall Street’s Top Talent | EP168
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
From Losing Everything to Startup of the Year: Ilana Golan’s 5 Shifts to Reinvent Yourself | E167
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
Milk Bar CEO Christina Tosi: How a Home Baker Built One of America's Most Beloved Brands | E166
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
Google X's Astro Teller: Why the Biggest Breakthroughs Start with Failure | EP165
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
The Corporate Ladder Is On Fire: How David Rogier Built MasterClass and What He’d Build Now | E164
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
Tom Bilyeu: How I Proved Everyone Wrong and Built a Billion-Dollar Brand | E62
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
Amy Porterfield: Why I Quit My Dream Job to Become an Entrepreneur | EP 89
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
GaryVee on Building an Unstoppable Mindset | E115
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
From Blue Collar Hustles to Billion Dollar Businesses: The Journey of David Royce
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
From Skype to Wix: Mark Tluszcz’s Formula for Turning Bold Bets into Billion-Dollar Successes | E163
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
Self-Made Billionaire: How John Paul DeJoria Built Paul Mitchell with $700 | E162
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
Former WWE President: The Hard Decisions That Built a Global Media Business | George Barrios | E161
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
The Lean Startup: Eric Ries Reveals the #1 Mistake New Founders Make | E160
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
Entrepreneur Magazine’s Jason Feifer: How to Build a Career Beyond Your Job Title | E159
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: How I Spot Billion-Dollar Companies Before Anyone Else | E158
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
Kickstarter Co-Founder: How Yancey Strickler Built a $7B Platform That Transformed Crowdfunding | E157
When Yancey Strickler moved to New York, he was broke, freelancing for $50, and chasing a writing career. Little did he know, his gift for building on the internet would soon change the world of crowdfunding. A chance encounter with a friend and a half-baked idea about crowd-funded concert tickets led to the founding of Kickstarter, a platform that has raised over $7 billion for creative projects
Elena Cardone: Overcoming Trauma and Loss to Build a $5 Billion Business | E156
Elena Cardone’s life changed the day she watched her best friend die in a house fire. That trauma sent her spiraling into a decade of drugs and alcohol, and as more friends died in the years that followed, she believed she was next. Until one night, a dream forced her to confront the truth: she wasn’t honoring her friend’s life; she was wasting her own. That moment became the turning point that se
The Dark Truth About Venture Capital: Confessions of a Unicorn Founder | Ra'anan Cohen | E155
Ra’anan Cohen walked into the tech world with no fancy degree and no startup pedigree; just a phone call from a friend and the promise of free food and a gym membership. From day one, he felt like an outsider, constantly battling imposter syndrome. Yet, he stuck with it, learned the ropes of the startup world, and ultimately founded a billion-dollar company. In this episode, Ra’anan joins Ilana to
9x Founder Kim Perell: How I Turned a $10K Loan Into a $235M Company | E154
When Kim Perell was fired, she had to fire all her friends on the same day. The company she thought would make her a millionaire had just gone bankrupt, leaving her with no income or backup plan. Instead of giving up, she took a $10,000 loan from her grandmother to start her first company from her kitchen table. That bet led to a $20 million exit and eventually, a $235 million company. In this epi
How Basecamp's CEO Lost 30% of His Team, Faced Backlash, and Came Back Stronger | Jason Fried | E153
Jason Fried didn’t follow the startup rules most founders swear by. He rejected venture capital, refused to chase growth at all costs, and chose to stay small on purpose. What started as a scrappy web design agency turned into Basecamp, a multi-million-dollar business built on profitability, simplicity, and conviction. In this episode, Jason joins Ilana to challenge everything you think you know a
Qualcomm CMO Don McGuire: How to Stay Relevant, Resilient, and Ready for Change | E152
Don McGuire did not build his career through a straight line. He lost elections as a kid, moved every few years, started over again and again, and had to learn resilience early. After graduating from college, he was still unsure what to do, but a leap into the early cellular industry launched a career that would take him from sales to marketing and ultimately, the CMO seat at Qualcomm. In this epi
What It Takes to Scale a Company Without Breaking It | Mike Seckler, Justworks CEO | E151
In the late 1990s, Mike Seckler started a company with little experience, plenty of curiosity, and no idea what was coming. Then the dot-com bubble burst. Almost overnight, capital disappeared. Companies collapsed. And Mike faced one of the hardest decisions of his career: laying off a third of his team to keep the company alive. That moment changed how he builds companies and leads today as CEO o
Benchmark Partner, Bill Gurley: The Strategy That Makes You Stand Out in a Crowded Job Market | E150
When Bill Gurley wanted to break into Wall Street, there were no job postings waiting for him. So he flew to New York, knocked on doors, and asked strangers for meetings. That hustle launched a career that would eventually take him to Silicon Valley, where he became one of the most respected venture capitalists in tech. In this episode, Bill joins Ilana to reveal the unconventional lessons that sh
Behavioral Design Expert: The Hidden Belief Blocking Your Growth | Nir Eyal | E149
Nir Eyal grew up clinically obese, ashamed of his body, and convinced that food controlled him. He tried every diet: low-fat, keto, vegetarian, and intermittent fasting. Each one worked until it didn’t. What finally changed his life wasn’t a meal plan; it was his belief. When he believed a plan would work, it worked. When that belief cracked, the weight returned. And he realized this pattern doesn
From Burned-Out Doctor to Global Wellness Founder: Dr. Amy Shah's Bold Career Pivot | E148
Dr. Amy Shah did everything she was supposed to do. Ivy League education. Elite medical training. Multiple board certifications. On paper, her life looked like a success. But behind the accolades, she was exhausted, disconnected, and running on stress. Then a near-fatal car accident forced her to confront a hard truth. The life she built was slowly breaking her body and mind. In this episode, Amy
Discover Your Working Genius and Beat Career Burnout | Patrick Lencioni | E147
The world tells leaders they must be everything: visionary, innovator, operator, executor. Patrick Lencioni tried, but it nearly crushed him. He wasn’t exhausted from effort; he was exhausted from misalignment. He discovered what most high performers never admit: trying to be everything is the fastest path to burnout. That insight became The Six Types of Working Genius, a simple framework reshapin
From Homeless Shelter to Building a Billion-Dollar Mortgage Company | Damian Maldonado | E146
Before Damian Maldonado was negotiating billion-dollar valuations or building businesses across Puerto Rico, he was a kid living in poverty and sharing bunk beds in a homeless shelter with his brothers. But those early years didn’t break him. They led him to become the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S. In this episode, Damian
From Pastor to Million-Dollar Days: Eileen Wilder on Charging Your Worth | E145
After two decades as a pastor making $50K a year, Eileen Wilder woke up to a terrifying truth: she was meant for more. Her body was breaking down. Her joy was gone. Then she walked into a conference that changed everything. Within 18 months, she went from broke and overwhelmed to generating seven figures as a coach. In this episode, Eileen joins Ilana to share how she pivoted from ministry to mill
Inc. & Fast Company CEO: How Stephanie Mehta Redefined the Path from Editor to CEO | E144
Stephanie Mehta never chased the CEO title. She chased the story. She built her career in some of the toughest newsrooms in the world, including The Wall Street Journal, Bloomberg, Fortune, and Vanity Fair, where credibility is earned line by line. Those same instincts eventually carried her beyond the newsroom and into leadership, leading her to the CEO seat at Mansueto Ventures, the company behi
Zoom CMO Kim Storin on Leading Through Brand Change When the Stakes Are High | E143
At just ten years old, Kim Storin was writing letters to CEOs, asking for donations and clearly outlining why her cause mattered. That instinct to connect people, solve problems, and step forward without permission never left her. Years later, as Chief Marketing Officer at Zoom, that same mindset shapes how she leads one of the most trusted brands in modern work. In this episode, Kim joins Ilana t
OpenAI's Former Head of GTM: What Leaders Get Wrong About AI & What’s Coming Next | Zack Kass | E142
Long before ChatGPT became a household name, Zack Kass was walking into boardrooms as Head of Go-To-Market at OpenAI, introducing executives to a technology they barely understood or cared about. Then one simple shift changed everything. Put intelligence into a familiar interface, remove friction, and suddenly the future arrived. In this episode, Zack joins Ilana to unpack what truly drove ChatGPT
From Childhood Trauma to Building High-Performance Leaders | Mick Hunt | E141
At just 10 years old, Mick Hunt made a promise that would shape the rest of his life. Growing up in a home marked by abuse, Mick stepped into a role no child should ever have to carry. He became the protector, the emotional anchor, and the one who believed he could change his family’s future. That moment didn’t just force him to grow up fast. It forged a lifelong mission around leadership, account
Care.com Founder Sheila Lirio Marcelo: How a Struggling Mom Built a Million Dollar Caregiving Empire | E140
As a young mom, primary breadwinner, and full-time professional, Sheila Lirio Marcelo understood the relentless struggle of balancing work and family. The constant search for reliable care left her feeling overwhelmed. Instead of accepting this as the norm, Sheila took matters into her own hands and created Care.com, a platform that has eased the caregiving burden for millions of families worldwid
Peloton’s Robin Arzón: From Hostage Survivor to Fitness Icon Inspiring Millions
Robin Arzón’s leap from lawyer to fitness powerhouse wasn’t just a career shift; it was a radical reinvention. After surviving a traumatic hostage situation, she turned to running as a way to heal, reclaim control, and push past limits. What began as a coping mechanism evolved into a mission: to complete ultra-marathons, build a global fitness brand, and inspire others as a lead instructor at Pelo
Russell Brunson: From Broke to $100M in Five Years, How I Bounced Back from Rock Bottom
Russell Brunson failed more times in his early 20s than most founders do in a lifetime. From broken funnels to failed product launches, he turned every setback into a lesson, refining his craft while navigating near bankruptcy, legal threats, and even moments where he feared jail time. Those hard years became the foundation that ultimately led him to co-found ClickFunnels, one of the fastest-growi
Building Wired Magazine: Kevin Kelly’s Unconventional Path from College Dropout E139
When Kevin Kelly dropped out of college in the 1970s, it was almost unheard of. Instead of following a traditional path, he chose a life driven by curiosity, freedom, and hands-on learning. That decision led him to hitchhike across Asia, document disappearing cultures, and eventually immerse himself in the early internet. Years later, he co-founded Wired, a magazine that soon became the voice of e
The Untold Story of Napster's Success, Collapse & Hard-Won Lessons | Jordan Ritter | E138
Jordan Ritter didn’t grow up surrounded by tech; he grew up on a farm, tinkering with computers in total isolation. But that early curiosity led him to co-found Napster, the file-sharing service that transformed music distribution. As millions of users flooded the platform, Jordan was instrumental in keeping it alive through sleepless nights and nonstop chaos. The success was massive, the failure
The Reinvention Queen: Guy Kawasaki Interviews Ilana Golan on Leaping Across Careers
Ilana Golan has reinvented herself more times than most people switch job titles. From becoming one of the first women to train F-16 pilots in the Israeli Air Force, to engineering, to product, to Silicon Valley executive, to investor, to founder, she’s rebuilt her identity again and again in industries that weren’t built for people like her. In this episode of the Remarkable People podcast, Guy K
Blackstone Medical’s Founder Vick Tipnes On Scaling a $500 Office Into a Healthcare Empire | E137
When Vick Tipnes launched Blackstone Medical Services, it was the worst possible moment: newly divorced, broke, and with two young kids. For years, he operated in survival mode, managing a business that lost money month after month. Instead of giving up, Vick's resilience became the driving force that turned a tiny, run-down $500 office into one of the fastest-growing sleep testing companies
The Powerhouse Behind MAC, Tom Ford Beauty & More: John Demsey’s Untold Career Lessons | E136
John Demsey didn’t become a powerhouse in the beauty industry by a mere stroke of luck; he built that influence on retail floors, taking on scrappy roles while learning the business in ways no MBA could ever teach. This helped him scale MAC Cosmetics into a global cultural movement, shape some of the most iconic beauty brands of our time, and ultimately rise to Group President of Estée Lauder Comp
Raising $24M After 107 Rejections: Anna-Sophie Hartvigsen’s Journey to Scaling Female Invest | E135
When 19-year-old Anna-Sophie Hartvigsen walked into a bank hoping to secure a loan to buy a property, she was denied on the spot. That “no” pushed her into investing and ultimately led her to co-found Female Invest, a global platform empowering women to take control of their financial futures. In this episode, Anna joins Ilana for a raw, honest conversation about the reality of fundraising as a fe
Brian Tracy: The Secrets to Doubling Your Income and Achieving Your Biggest Goals | LEAP Replay
Brian Tracy was fired from washing dishes, cars, and floors, and began to believe that “washing things” might be his destiny. But when he learned that the top 20% in any field earn 80% of the money, he committed to becoming one of them. That decision transformed him from a broke high school dropout into a global authority on success, speaking to millions across 84 countries and writing more than 8
Build-A-Bear CEO, Sharon Price John: The Mindset Behind a Billion-Dollar Comeback | E134
When Sharon Price John was a kid, she spent a summer determined to climb a massive tree. After several falls, she reached the top, only to realize she didn’t know how to get down. As darkness fell, she jumped into the pine needles below and learned a lasting lesson: tough goals can be fun. Years later, that same mindset guided her as CEO of Build-A-Bear Workshop, a company that was $49 million in
Wikipedia Co-Founder: How Jimmy Wales Changed the Internet Forever | E133
He could have built a billion-dollar company, but instead, Jimmy Wales built a movement. When the dotcom crash hit and funding vanished, he didn’t sell out or add ads. He doubled down on values, creating Wikipedia, a global temple for the mind that made knowledge free to billions. In this episode, Jimmy joins Ilana to share the story behind that decision, the failures that shaped him, and the comm
How Reebok’s Co-Founder Joe Foster and Ben Weiss Are Revolutionizing the Footwear Industry | E132
Ben Weiss set out to create the future of footwear. With nothing but conviction and a radical idea to merge AI with design, he reached out to Reebok co-founder Joe Foster, the man who turned a small factory dream into a global empire. What began as a cold message became a collaboration between two builders chasing the next revolution in shoes. In this episode, Ben and Joe join Ilana to unpack what
Square Co-Founder, Jim McKelvey: How to Build a Business No Competitor Can Copy | E131
Jim McKelvey did the impossible. He beat Amazon. The tech giant launched a product similar to Square’s, undercut their pricing, and leveraged its massive brand. Everyone thought Square was doomed. But a year later, Amazon quit and even mailed Square readers to their customers. That left Jim with a bigger question: “How did we survive when no one else ever has?” The search for that answer inspired
Betting $250M on Women’s Sports: How Rejection Became Kara Nortman’s Superpower | E130
At a 2015 World Cup match in Vancouver, Kara searched nine stores for her daughters’ jerseys and found none. That spark of “joyful irritation” became a movement to build teams, build community, and build an industry. In this episode, Kara joins Ilana to share how that moment ignited Angel City FC, how she, along with her partners, managed to create one of the most valuable women’s soccer teams in
How a Panic Attack Revealed the Secret to a Meaningful Life | Robert Glazer | E129
Robert Glazer collapsed in his kitchen in front of his son, convinced he was having a heart attack. In reality, it was a massive panic attack triggered by grinding too hard while starting a business, building a house, raising kids, and weathering the 2008 recession. That wake-up call forced him to reevaluate everything: his health, his leadership, and the values that guided his life. In this episo
How Thai Randolph Built a $100M Media Company | E128
Most people would assume that raising capital for a celebrity-backed business would be a cakewalk, but Thai Randolph knew that was far from the truth. Securing $100 million in investment for Kevin Hart's Hartbeat Productions required more than just a famous name; it took proving real value, building trust, and navigating rejection. Her success led to one of the largest private-equity rounds e
Lisa Bilyeu: From Housewife to Billion-Dollar Boss, My No-BS Guide to Radical Confidence | LEAP Replay
For eight years, Lisa Bilyeu lived the life others expected: a traditional Greek wife focused on supporting her husband and running the home. But deep down, she knew she was meant for more. With no business background, zero confidence, and no clear roadmap, she decided to rewrite her story. She co-founded Quest Nutrition with her husband and built a billion-dollar business. In this LEAP Replay, Li
Richard Branson: Virgin Group Founder on Turning Bold Risks into a Billion-Dollar Business | LEAP Replay
As a teenager, Sir Richard Branson had already mastered the art of taking bold leaps to pursue opportunities. Dyslexic and struggling in school, he quit at age 15 to launch a youth magazine, a move that eventually led to Virgin Records, Virgin Atlantic, and the Virgin Group empire. In this LEAP Replay, Richard joins Ilana to share how he turned obstacles into opportunities, embraced fearless risk-
From Losing Everything to Startup of the Year: Ilana Golan’s 5 Shifts to Reinvent Yourself | E127
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
Techstars Co-Founder, Brad Feld: How to Find Meaning While Achieving Success | E126
Despite outward success, Brad Feld struggled with depression, exhaustion, and feelings of emptiness. For years, he hid these challenges while relentlessly pushing forward as an entrepreneur. It wasn’t until his 40s, after seeking therapy and confronting his mental health, that Brad realized success wasn’t just about building companies, but about managing the emotional toll of entrepreneurship. Tod
1 Million Followers in 30 Days: Brendan Kane’s Proven Strategy for Going Viral | E125
Brendan Kane didn’t break into Hollywood through connections. He started out making coffee on film sets. Spotting the untapped power of MySpace and YouTube, he launched one of the first influencer campaigns, catching the attention of studio executives and A-list actors like Jason Statham. That bold move launched his journey from Hollywood to advising global icons such as Taylor Swift and Rihanna o
NetApp CEO George Kurian: From Humble Beginnings to Leading a Fortune 500 Giant | E124
George Kurian’s journey from a modest upbringing in Kerala, India, to becoming CEO of NetApp is an extraordinary story. George worked cafeteria shifts and construction jobs to pay his way through Princeton before climbing the ranks at Oracle, McKinsey, and Cisco. In this episode, George opens up about the weight of being a “rookie CEO” responsible for 12,000 people, the discipline of saying no to
Former Siemens CEO on Building an $80B Business While Avoiding Burnout | Klaus Kleinfeld | E123
Klaus Kleinfeld’s journey from a difficult childhood in Germany to leading two Fortune 500 companies, Siemens and Alcoa, was anything but easy. He experienced the true cost of leadership: the loneliness of making impossible decisions and the grit to push forward when every alternative seems bleak. In this episode, Klaus joins Ilana to share how resilience and freedom shaped his leadership philoso
Nathan Blecharczyk: The Raw Truth of Scaling Airbnb to a $75B Empire | E122
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
How Case Kenny Turned His Podcast into a Multi-Million Dollar Brand | E121
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
How Julia Hartz Built Eventbrite from a Startup to a Billion-Dollar IPO | E120
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 c
68 Rejections, One Yes: How I Built a $100M Startup Against All Odds | Dan Shapiro | E119
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: From Healing My Mom of Cancer to Building a Multi-Million-Dollar Health Brand | E118
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: The 5 Types of Wealth, How to Find True Success and Fulfillment Beyond Money | E117
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 r
Christiana Figueres: Building a Lasting Legacy in Global Climate Action at the UN and Beyond | E116
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
GaryVee: The Mindset That Took Me from Zero to Multi-Million-Dollar Success | E115
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: How to Conquer Anxiety and Lead Powerful Conversations Under Pressure | E114
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
From Singing in Parks to Selling Out Arenas: AJR’s Adam Met on Building Success from Scratch | E113
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
From Near Bankruptcy to a $745M Exit: The Raw Truth Behind Kass & Mike’s Entrepreneurship Journey | E112
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
NBCUniversal Vice Chairman, Bonnie Hammer: Breaking Myths About Climbing to the Top | E111
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
Gretchen Carlson: The Journalist Who Defied Fox News and Exposed Workplace Abuse | E110
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
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109
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 W
Breaking the Glass Ceiling: How Adva Amir Became One of the Few Female Airline Captains | E108
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
From School Teacher to Fitness Icon: What I Wish I Knew Before Quitting My Job | Brian Keane | E107
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
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