The Leap Academy Podcast with Ilana Golan is all about honest and inspiring conversations about what it really takes to leap to bigger things, amazing careers, and craft the life you want. Stories and tips you won't find anywhere else. Ilana speaks with some of the world's most influential people, experts, and thinkers who created incredible careers, massive impact, built a reputation, and an extraordinary life. Together we discover the untold truths, the emotions, and important lessons that ...
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The Leap Academy Podcast with Ilana Golan is all about honest and inspiring conversations about what it really takes to leap to bigger things, amazing careers, and craft the life you want. Stories and tips you won't find anywhere else. Ilana speaks with some of the world's most influential people, experts, and thinkers who created incredible career…
…
continue reading
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Steph Curry Enterprise: From Receptionist to Driving Business Success for a Sports Icon | Tiffany Williams
30:45
30:45
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30:45Tiffany Williams started as a part-time receptionist with the Golden State Warriors, just looking to get her foot in the door. Two weeks later, she was offered a full-time role and quickly rose into business development. In 2015, she led the planning of the Warriors’ NBA Championship parade, an experience that fueled her drive for bigger opportunit…
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Seth Godin: Turning 800 Rejections into a Roadmap for Success
37:57
37:57
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37:57Where most people give up after a handful of rejections, Seth Godin got rejected 800 times by editors before finally making a big break. For him, every “no” was a clue. He adapted and mastered the system, and soon, the same editors who dismissed him were calling him first. His success wasn’t luck or passion. It was built by showing up, iterating, a…
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Gil Shwed: Building Check Point into a $20B Empire and Defining the Future of Cybersecurity
57:23
57:23
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57:23Gil Shwed built Check Point into a $20 billion cybersecurity giant, but it all began with a flaw he spotted as a programmer in the Israeli military. Tasked with connecting classified networks, he uncovered a vulnerability, and the idea for a firewall was born. A few years later, he launched Check Point, betting on internet security before the web e…
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Too Broke for Bankruptcy: How Michael Hyatt Rebuilt Success Without Sacrificing His Life
1:05:03
1:05:03
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1:05:03After the crash of his company, Michael Hyatt was determined to rise again. Returning to his old publishing firm, he took on a failing division and turned it into the most profitable. His hard work paid off with a massive bonus check. But when he rushed home to celebrate, his wife was in tears. He had put his all in at work, at the cost of his fami…
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How I Lost My Company and Built a $500M Business Instead | Brandon Dawson
45:49
45:49
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45:49At 29 years old, Brandon Dawson was on top of the world. He had taken his company public, stood on the American Stock Exchange floor, and rang the bell. He felt unstoppable until his private equity investors sold his company against his will. Most people would have quit, but Brandon learned from this setback, cracked the code to scaling, and went o…
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Craigslist Founder, Craig Newmark: How I Transformed a Simple Email List Into a Billion-Dollar Business
35:06
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35:06After Craig Newmark moved to San Franciso in 1995, he had a simple idea: a mailing list to share local events with friends. It wasn’t fancy and certainly wasn’t meant to change the world. However, as the list grew, people began calling it “Craigslist,” unknowingly naming what would become a billion-dollar digital marketplace. In this episode, Craig…
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GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
46:56
46:56
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46:56Gary ‘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…
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Trent Shelton: Your Pain Has a Purpose, Unlock Its Power
40:40
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40:40Trent 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 shar…
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Crippling Anxiety: How I Beat Panic Attacks to Become a 3x USA Memory Champion | John Graham
51:18
51:18
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51:18John 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 other…
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If You Want to Have Life-Changing Conversations, Ask These Tough Questions | Topaz Adizes
59:33
59:33
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59:33After 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 hon…
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Shark Tank’s Matt Higgins: How I Beat Poverty, Loss, and Cancer to Become a Global Investor
1:01:36
1:01:36
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1:01:36Matt 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…
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Bluestone Lane Founder: How Nicholas Stone Is Redefining the U.S. Coffee Culture With Zero Coffee Experience
55:59
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55:59It 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, Austr…
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Former Medtronic CEO: Leadership Secrets for Achieving Success Beyond Profits | Bill George
59:52
59:52
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59:52After 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 o…
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Former Managing Director of Facebook India, Kirthiga Reddy: How to Seize Life-Changing Opportunities
47:13
47:13
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47:13Kirthiga 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, …
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How Lacy Garcia Conquered Financial Fear and Transformed Wealth Planning for All
48:09
48:09
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48:09Despite 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 driv…
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Neil Patel: From Crushing Failures to Building a Global Marketing Empire
44:20
44:20
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44:20Neil 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 chall…
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Peloton VP, Robin Arzón: Surviving a Hostage Crisis and Building a Relentless Fitness Brand
41:14
41:14
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41:14A 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 refu…
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Naveen Jain: Turning Audacious Ideas Into Life-Changing Innovations
56:52
56:52
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56:52Naveen 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…
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From LA Dodgers to George Clooney’s Cocktail Hour: How Jeff Krauss Plans Iconic Events
46:42
46:42
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46:42Jeff 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 fo…
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Empowering 5 Million Entrepreneurs: Making Business a Force for Global Good | Jessica Jackley
33:33
33:33
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33:33Jessica 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 20…
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Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises
47:04
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47:04Spencer 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 bi…
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Tom Bilyeu: How I Proved Everyone Wrong and Built a Billion-Dollar Brand
57:15
57:15
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57:15Tom 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.…
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Wistia CEO, Chris Savage: Master the Art of Pivoting, How to Adapt and Grow Against the Odds
52:16
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52:16Chris 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 majo…
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Russell Brunson: From Rock Bottom to $100 Million in 5 Years with ClickFunnels
54:00
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54:00At 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, …
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Nextdoor’s Bryan Power: Turning Big, Scary Opportunities into Career-Defining Success
47:34
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47:34Known 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 si…
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The Accidental Entrepreneur: How Andrew Lacy Turned Rejection into Health Tech Innovation
47:02
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47:02Andrew 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 …
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Surviving Lies, Rumors, and Digital Hate: Dan Ariely’s Guide to Thriving Online
50:45
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50:45Dan 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 h…
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Howard Behar, Former Starbucks President: Putting People Over Profits for Lasting Impact
53:11
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53:11Howard 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 fa…
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Lisa Bilyeu: Radical Confidence, My Journey From Housewife to Billion-Dollar Boss
1:10:59
1:10:59
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1:10:59In 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…
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Taking Big Risks: How David Jones Built a Billion-Dollar Brand Against All Odds
56:42
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56:42Convinced 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…
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Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein
56:03
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56:03Harley 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 the…
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Richard Branson: The Journey to a Multi-Billion Dollar Empire
22:34
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22:34From 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 s…
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Jeff Dudan, Undercover Boss: How I Built a Thriving National Franchise From Scratch
49:10
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49:10Jeff 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 opportun…
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Making Big Ideas Happen: How Katrina Spade Transformed the Funeral Industry Forever
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46:06One 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 c…
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Going All In: How Russ Ruffino Went from Bartender to $100M CEO
51:19
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51:19Russ 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…
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How to Win: Master FBI Negotiator’s Secrets for Getting What You Want | Chris Voss
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44:23Chris 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 …
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Turning Pain into Purpose: How Anne Beiler Built a Pretzel Empire from Nothing
56:13
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56:13Before building a global snack empire, Anne Beiler’s dream was to have her own family like the loving one she grew up in. Like a fairytale, she met the man of her dreams. But years later, she found herself stuck in a place of darkness after tragically losing her daughter and enduring years of abuse. Through this pain, however, Anne found a new purp…
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Your Authenticity is Your Superpower, Master The Art of Authentic Leadership with Scot Safon
55:37
55:37
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55:37Early in his career, Scot was told that he wasn’t “tough enough” for the media industry. He didn’t fit the traditional image of a hard-nosed executive. But instead of changing who he was, Scot embraced his own authentic style of leadership, ultimately proving that enthusiasm and a focus on collaboration are just as powerful for success. He went on …
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How Forbes 30 Under 30 Kira Radinsky Turns Every ‘No’ Into Opportunity
46:48
46:48
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46:48Fascinated with science as a young child, Kira Radinsky was driven to make a meaningful impact on the world through technology. She faced rejection after rejection while building her first startup, but her resilience paid off when eBay acquired the company. Kira didn’t stop there—she developed AI models that successfully predicted cholera outbreaks…
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The Woman Who Transformed How We Think About Inclusive Leadership | Sally Helgesen
50:48
50:48
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50:48Frustrated by how women’s voices were being ignored in the corporate world, Sally Helgesen started documenting the leadership styles of successful women. Her efforts culminated in the groundbreaking book, The Female Advantage, which changed the course of her career. Despite the uncertainty, Sally left her dream job for the male-dominated space of l…
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Brian Tracy: The Unbreakable Laws of Money and Success
1:19:31
1:19:31
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1:19:31Brian Tracy went from struggling with a series of menial jobs to achieving remarkable sales success. A relentless self-learner, he transformed his life by mastering the science of sales. Then, he dedicated himself to studying, researching, writing, and speaking in the fields of economics, history, business, philosophy, and psychology. Today, he is …
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How I Built a 7-Figure Business While Working a Corporate Job | Kelly Roach
41:45
41:45
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41:45Kelly Roach built a seven-figure side hustle before leaving her corporate role. How did she do it despite an intense workload and failed product launches? Strategic planning, smart time management, and an unyielding drive fueled by a childhood embarrassment on the free lunch line. In this episode, Kelly shares her inspiring journey, emphasizing the…
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Hunger Beats Talent: Dr. Geoff Smart’s Formula for Hiring Success
57:35
57:35
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57:35Even when met with skepticism, Geoff Smart pushed forward with his vision to transform hiring through powerful data-driven methods. He created the WHO Method through his leadership consulting firm, emphasizing drive and cultural fit over skills. This approach not only brought success to his clients but also propelled his firm to global success. In …
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Balancing Entrepreneurship and Motherhood While Building a Billion Dollar Company | Eynat Guez
49:39
49:39
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49:39Eynat Guez leaped from a comfortable corporate job to co-founding Papaya Global. Despite numerous investor rejections, she stayed true to her vision, proving the market need for her innovative solutions. Balancing motherhood and entrepreneurship, she turned her startup into a global payroll and HR solutions powerhouse valued at $3.7 billion. In thi…
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Running the Sahara, Raising Millions, and Finding Purpose in Prison | Charlie Engle
1:05:15
1:05:15
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1:05:15As Charlie Engle's teenage sons dropped him off at the gates of federal prison, he faced his lowest point. Sentenced to 21 months for mail fraud, he had lost his career, reputation, and freedom. Despite his history of overcoming addiction and running across the Sahara, this challenge was the hardest. Initially consumed by anger and fear, Charlie tu…
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Siri Co-Founder: Adam Cheyer on Innovation, Persistence, and Timing Big Wins
42:11
42:11
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42:11Feeling creatively stifled in his stable but unfulfilling job, Adam Cheyer pursued entrepreneurship, even with his limited business knowledge. He co-founded Siri to realize his dream of a voice-activated assistant and the project was so promising that Steve Jobs called out of the blue. Despite initially turning down his offer, Jobs persisted. Today…
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Ending Hunger: How This Accidental Activist Found Her Passion | Ronni Kahn
57:44
57:44
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57:44Immersed in her privileged life in apartheid South Africa, Ronni Kahn never imagined she would become a leader in the fight against food waste and hunger. She went from one bold leap to the next—leaving a kibbutz in Israel to start from scratch in a new country, then building a successful business only to leave it to start a nonprofit. In this epis…
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Marshall Goldsmith, #1 Executive Coach: How to Find Purpose and Meaning in Life
40:07
40:07
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40:07From nearly failing out of college to becoming the number one executive coach, Marshall Goldsmith embodies the power of relentless self-improvement. Shaped by harrowing experiences, influential mentors, and Buddhism, he has gained unique perspectives on gratitude, resilience, and purpose, inspiring leaders worldwide to achieve their full potential.…
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Dave Liniger, RE/MAX Co-Founder: How to Disrupt an Industry and Turn Failures to Fortunes
57:52
57:52
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57:52Dave Liniger went from pinching pennies while saving for his first property to owning 21 single-family homes at age 21. Despite fierce opposition and financial turmoil, he implemented an innovative commission system that empowered agents to maximize their earnings. His unique model not only transformed his company into a global real estate powerhou…
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