Leap Academy with Ilana Golan

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 episode, Don chats with Ilana about how to stay in control of your career in a world changing at the speed of AI. He shares why resilience matters more than ever, how to spot the right time to leap, and what it takes to stay relevant in a crowded job market. Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, with over 25 years of experience across service providers, semiconductors, and technology marketing. In 2025, he was named one of Forbes’ World’s Most Influential CMOs. In this episode, Ilana and Don will discuss: (00:00) Introduction (03:14) The Early Experiences That Built Don’s Resilience (10:46) His Love for Marketing and Journey Into Tech (18:00) The Transition From Sales to Marketing (20:18) Why You Must Stay in Control of Your Own Destiny (23:25) Startup Lessons, Consulting, and Selling Yourself (27:43) Knowing When It Was Time to Leap Back Into Corporate (31:45) The Crisis That Forced Qualcomm to Tell Its Story (38:16) The One Trait Gen Z and Gen Alpha Need Most (40:33) How to Stand Out in an AI-Driven Job Market (45:02) Why Portfolio Careers and Side Skills Matter (48:03) What Excites Don Most About Qualcomm’s Future (53:05) Q&A: How to Break the “I Can’t Get a Job” Mindset Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, where he oversees global marketing as the company expands beyond mobile into automotive, computing, AI, and other growth areas. Before joining Qualcomm, he held senior leadership roles at Intel and other major wireless and technology companies. In 2025, he was named one of Forbes’ World’s Most Influential CMOs. Connect with Don: Don’s LinkedIn: linkedin.com/in/donnymac Resources Mentioned: Qualcomm: https://www.qualcomm.com/ Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 of Justworks. In this episode, Mike joins Ilana to share the real lessons behind building and scaling through uncertainty and how founders can avoid the leadership mistakes that derail most companies. Mike Seckler is the President and CEO of Justworks, an HR platform helping over 14,000 small businesses manage payroll, benefits, compliance, and workforce management. In this episode, Ilana and Mike will discuss: (00:00) Introduction (02:42) From History and Geology Student to Entrepreneur (07:05) The Early Days of Founding Employease (09:08) Navigating the Dot Com Crash as a Founder (14:53) Selling to ADP and Starting a New Venture (17:23) Joining Justworks: From Board Member to COO (24:37) Lessons from Transitioning to Justworks’ CEO (26:00) The Biggest Blindspots for Small Businesses (31:58) How to Beat Founder Loneliness (36:34) Adapting to a Rapidly Evolving Market (42:03) Justworks: Empowering Small Businesses for Growth (44:49) Review and Q&A: BREAD Productivity Framework Mike Seckler is a serial entrepreneur who has built and scaled multiple companies over the past two decades. Before joining Justworks, he co-founded Employease, an HR outsourcing firm that was eventually acquired by ADP, and later co-founded Euclidean Technologies, a company applying machine learning to public market investing. Today, as CEO of Justworks, Mike leads a platform serving thousands of small businesses and helping founders navigate the complexities of building and scaling their teams. Connect with Mike: Mike’s LinkedIn: linkedin.com/in/mikeseckler Resources Mentioned: Justworks Website: https://www.justworks.com Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 shaped his journey. From chasing curiosity to designing your own career path, he explains how anyone can create opportunities, stand out in a crowded field, and build a career that actually excites them. Bill Gurley is a Silicon Valley venture capitalist and a longtime partner at Benchmark Capital, a Silicon Valley venture capital firm. He has invested in and served on the boards of major companies, including Uber, OpenTable, Zillow, Nextdoor, and Stitch Fix. In this episode, Ilana and Bill will discuss: (00:00) Introduction (03:14) Where Bill Gurley’s Tech Curiosity Began (05:09) Transitioning from Engineering to Finance (08:25) Breaking Into Wall Street Without a Job Posting (14:24) The Question That Made Him Quit Wall Street (19:59) Making a Pivot to Venture Capital (24:41) The Best Way to Get Into Venture Capital (26:50) How to Know If You’re in the Right Career (30:30) The Role of Experimentation in Career Growth (33:20) How to Stand Out in a Competitive Job Market (37:29) Why Location Can Make or Break Your Career (40:50) Breaking Free From the “Safe Career” Pressure (48:30) The 5–5–5 Rule for Career Experiments Bill Gurley is a venture capitalist, technology investor, and general partner at Benchmark Capital, best known for his early investment in companies like Uber. Before venture capital, he worked as an engineer at Compaq and later as a Wall Street technology analyst. Throughout his career, Bill has been known for identifying transformative companies early and for his widely read blog Above the Cloud. His new book, Running Down a Dream, offers a practical guide to building a fulfilling career Connect with Bill: Bill’s X (Twitter): x.com/bgurley Bill’s Website: abovethecrowd.com Resources Mentioned: Bill’s Book, Runnin' Down a Dream: How to Thrive in a Career You Actually Love: https://www.amazon.com/dp/0593799666 One Up On Wall Street: How to Use What You Already Know to Make Money in the Market by Peter Lynch: https://www.amazon.com/dp/0743200403 Range: Why Generalists Triumph in a Specialized World by David Epstein: https://www.amazon.com/dp/0735214484 Greenlights by Matthew McConaughey: https://www.amazon.com/dp/0593139135 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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’t just apply to weight; it shows up in every area of life. In this episode, Nir joins Ilana to reveal the hidden force behind your success or stagnation. He unpacks the science of belief, how it shapes what you see, feel, and do, and the practical framework to break limiting beliefs before they break you. Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer known for his work on habit formation, psychology, and human behavior. As an entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!. In this episode, Ilana and Nir will discuss: (00:00) Introduction (03:14) Childhood and Weight Loss Struggles (07:34) Why Affirmations and Vision Boards Don’t Work (09:18) Facts vs Faith vs Beliefs (10:59) His Journey from Founder to Bestselling Author (16:01) The Power of Belief in Success and Failure (24:49) The ‘Messy Middle’: Knowing When to Persist vs Quit (32:06) Skills Gap vs Belief Gap in Leaders and Teams (34:0) The Four Questions to Rewire a Limiting Belief (46:51) Q&A: Crafting a Memorable Pitch Story Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer. He is the author of Hooked and Indistractable, which have sold over one million copies worldwide and been translated into more than 30 languages. His latest book, Beyond Belief, explores how hidden beliefs shape our limitations and how to replace them to unlock personal and professional growth. An entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!. Connect with Nir: Nir’s Website: http://nirandfar.com Nir’s Instagram: instagram.com/neyal99 Nir’s LinkedIn: linkedin.com/in/nireyal Resources Mentioned: Nir’s Books: Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Breakthrough Results: https://www.amazon.com/dp/0593852036 Indistractable: How to Control Your Attention and Choose Your Life: https://www.amazon.com/dp/194883653X Hooked: How to Build Habit-Forming Products: https://www.amazon.com/dp/1591847788 Nir’s 30-Day Belief Transformation Journal: nirandfar.com/beyond-belief Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 joins Ilana to share how a personal health crisis became the catalyst for a complete reinvention. She opens up about leaving the traditional medical path without burning the boats, building a science-backed wellness platform, and why women are being failed by modern healthcare. Dr. Amy Shah is a double board-certified physician and nutrition specialist. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine. In this episode, Ilana and Dr. Amy will discuss: (00:00) Introduction (03:30) How a Near-Fatal Accident Became a Wake-Up Call (09:51) From Traditional Medical Path to a Wellness Brand (13:08) Building a Personal Brand Despite Pushback (17:13) The Power of Having a Supportive Network (21:47) How Dr. Amy Built a Powerful Portfolio Career (23:51) Understanding Women's Health: The 30-30-3 Framework (26:41) The Science of Probiotics and Gut Health (30:24) The 4-3-2-1 Movement Framework for Peak Health (37:32) Managing Stress and Cortisol Levels (43:42) Building a Personal Brand and Finding Your Path (47:17) Her Immigrant Roots and Its Impact (51:44) Review and Q&A: Beating Ageism in Your Career Journey Dr. Amy Shah is a double board-certified physician and nutrition specialist. She is the bestselling author of I’m So Effing Hungry and I’m So Effing Tired. Her latest book, Hormone Havoc, offers a science-backed guide to navigating the complexities of perimenopause and menopause. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine. Connect with Dr. Amy: Dr. Amy’s Website: https://amymdwellness.com Dr. Amy’s Instagram: instagram.com/dramyshah Resources Mentioned: Dr. Amy’s Books, Hormone Havoc: A Science-Backed Protocol for Perimenopause and Menopause: Sleep Better. Think Better. Feel Better: https://www.amazon.com/dp/0063420856 I'm So Effing Hungry: Why We Crave What We Crave – and What to Do About It: https://www.amazon.com/dp/0063285118 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 reshaping how teams work by aligning people with the work that gives them energy. In this episode, Patrick joins Ilana to break down the Six Types of Working Genius and show how aligning your strengths can transform your career, your team, and your fulfillment at work. Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity. In this episode, Ilana and Patrick will discuss: (00:00) Introduction (02:46) Patrick’s Early Life and Career Beginnings (08:31) Joining Oracle and Pitching Ideas (12:36) Turning Down a Job Offer from Steve Jobs (15:40) The Decision to Start the Table Group (20:18) Navigating the Hard Moments in Entrepreneurship (23:30) Short Attention Spans as a Bestselling Author (28:06) The Birth and Impact of Working Genius (34:48) Applying Working Genius to Career Choices (41:05) W-I-D-G-E-T: The Six Types of Working Genius (54:57) Healing Childhood Scars and Understanding Self (59:15) Q&A: The Keys to Building a Portfolio Career Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. He has written 13 books with over 7 million copies sold worldwide, including The Five Dysfunctions of a Team. He is also the creator of The 6 Types of Working Genius, a framework that helps teams identify the work that energizes them and improves performance. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity. Connect with Patrick: Patrick’s LinkedIn: linkedin.com/in/patrick-lencioni-orghealth Patrick’s Instagram: instagram.com/patricklencioniofficial Resources Mentioned: Patrick’s Books: The Five Temptations of a CEO: https://www.amazon.com/dp/B0062OAEWM The Five Dysfunctions of a Team: https://www.amazon.com/dp/0787960756 The 6 Types of Working Genius: A Better Way to Understand Your Gifts, Your Frustrations, and Your Team: https://www.amazon.com/dp/B09XGPCM36 Working Genius Website: https://www.workinggenius.com Take the Working Genius Assessment: https://www.workinggenius.com/about/assessment Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 joins Ilana to share how growing up in poverty shaped his relationship with risk, money, and resilience, and what it really takes to bootstrap a company through market crashes, massive layoffs, and billion-dollar decisions. Damian Maldonado is a serial entrepreneur, investor, and co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. In this episode, Ilana and Damian will discuss: (00:00) Introduction (02:57) Growing Up in Poverty and a Homeless Shelter (08:42) Key Lessons from Early Jobs (11:42) Pitching to a CEO at 21 Without Fear of Rejection (14:38) Damian’s Journey into the Mortgage Industry (19:14) Starting America Financing With No Safety Net (22:30) Leading Through Layoffs and Downturns (27:07) Why He Turned Down a Billion-Dollar Offer (30:57) Leadership Lessons from Richard Branson (34:25) Building a Portfolio Career with Adventure (42:53) Q&A: Crafting a Response to ‘Tell Me About Yourself’ Damian Maldonado is the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. He also co-founded American Home Agents and has expanded his business interests into hospitality and lifestyle ventures in Puerto Rico, including a boutique beachfront hotel, restaurant, and kiteboarding school, creating jobs and adding value to the local community. Connect with Damian: Damian’s Website: https://damianmaldonado.com Damian’s Instagram: instagram.com/damiankitepr Resources Mentioned: American Financing Website: americanfinancing.net Numero Uno Website: numerounopr.com Awaken the Giant Within by Tony Robbins: https://www.amazon.com/Awaken-Giant-Within-Immediate-Emotional/dp/0671791540 Think And Grow Rich by Napoleon Hill: https://www.amazon.com/Think-Grow-Rich-Landmark-Bestseller/dp/1585424331 Rich Dad Poor Dad by Robert Kiyosaki: https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612681131/ The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 million-dollar offers, how immersive events like LeapCon can fast-track your growth, and the powerful exercise that will help you package your expertise and charge your worth. Eileen Wilder is a bestselling author and high-ticket business coach helping individuals package their expertise into profitable high-ticket offers. As a keynote speaker, she has shared stages with leaders like Tony Robbins, Russell Brunson, Ed Mylett, and Bishop T.D. Jakes, empowering others to build wealth, freedom, and impact. In this episode, Ilana and Eileen will discuss: (00:00) Introduction (04:06) Eileen's Journey from Pastor to Entrepreneur (07:35) Discovering Life Coaching at a Conference (14:01) The Life-Changing Impact of Events (16:17) How a “Janky” Video Took Her from $297 to $250K (18:35) Losing Her Mother and Finding Financial Power (24:00) From $50K Salary to Seven Figures in 18 Months (26:57) Practical Exercise for Commanding Premium Prices (35:22) $1 Million in a Day: The Power of High-Ticket Offers (40:12) Mastering the Art of Public Speaking (42:39) LeapCon 2026: A Transformational Experience (44:53) The Key to Pricing Your Services Eileen Wilder is a bestselling author, business growth consultant, and keynote speaker who helps entrepreneurs and creators turn their expertise into profitable high-ticket offers and virtual events. A former pastor of 20+ years, she transformed her fear of public speaking into a seven-figure speaking career and is now known as “The Queen of Stages.” Eileen has shared stages with leaders like Tony Robbins, Russell Brunson, Ed Mylett, and Bishop T.D. Jakes, empowering others to build wealth, freedom, and impact. Connect with Eileen: Eileen’s Website: https://eileenwilder.com Eileen’s Instagram: instagram.com/eileenwild Resources Mentioned: Eileen’s Book, Financially Free: How To Create Your Own Economy No Matter What's Going On In the World Around You: https://www.financiallyfreebook.com/ff-1 Eileen’s Book, The Pivot Plan: End Emotional Exhaustion, Overcome Depression, Discover Your Strongest Life: https://www.amazon.com/dp/1943127719 The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma by Bessel van der Kolk, M.D.: https://www.amazon.com/dp/0143127748 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 behind Fast Company and Inc. In this episode, Stephanie joins Ilana to share her journey from journalism student to leading iconic media brands, the challenges of stepping into executive leadership, and how to prioritize as a leader in an ever-changing industry. Stephanie Mehta is a journalist, business executive, and CEO and chief content officer of Mansueto Ventures, the media company that publishes Fast Company and Inc. magazines. She has held senior editorial roles at Fortune, Bloomberg, and Vanity Fair. In this episode, Ilana and Stephanie will discuss: (00:00) Introduction (02:52) Stephanie's Early Career in Journalism (05:16) Challenges and Growth at the Wall Street Journal (10:35) Transitioning to Fortune Magazine (17:38) Reflecting on 14 Years at Fortune (22:42) Taking a Break and Exploring New Opportunities (27:18) Becoming the CEO of Fast Company (35:37) How to Get Stories Published in Major Media (39:11) Rising Above the Noise in Business (42:01) How Stephanie Prioritizes as a CEO (45:26) How Careers are Changing in the Modern Era (49:31) The Impact of Immigrant Upbringing Stephanie Mehta is a journalist, business executive, and CEO and chief content officer of Mansueto Ventures, the media company that publishes Fast Company and Inc. magazines. She previously served as Editor-in-Chief of Fast Company and held senior editorial roles at Fortune, Bloomberg, and Vanity Fair. Stephanie is also the author of the Modern CEO newsletter, where she explores leadership, careers, and the future of work. Connect with Stephanie: Stephanie’s LinkedIn: linkedin.com/in/stephanie-mehta-media-ceo Resources Mentioned: Modern CEO Newsletter: https://www.fastcompany.com/section/modern-ceo Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 to share Zoom’s evolution from a single, iconic product into a broad portfolio of solutions, and what it takes to reinvent a brand the world already relies on without losing trust. Kim Storin is the Chief Marketing Officer at Zoom and a seasoned marketing leader with experience spanning consulting, enterprise transformation, and global brand leadership. She has held senior leadership roles at companies including Dell, IBM, and Deloitte. In this episode, Ilana and Kim will discuss: (00:00) Introduction (03:44) Making Bold Requests at Age Ten (06:28) Problem Solving as Her Career Compass (14:53) Receiving the Hardest Feedback of Her Career (17:40) Athletic Pursuits and Influence on Leadership (20:50) Joining Zoom and Leading Its Transformation (23:38) How Zoom Reinvented and Repositioned Itself (27:12) The New Era of Marketing and How to Stay Ahead (30:33) AI as a Teammate, Not a Threat (35:08) Redefining Success Beyond Metrics and Titles (38:30) The Right Way to Build a Portfolio Career Kim Storin is the Chief Marketing Officer at Zoom, where she leads global marketing strategy, brand, and growth as the company evolves into a broader communications platform. Prior to Zoom, Kim held senior leadership roles at companies including Dell, IBM, Deloitte, and multiple high-growth organizations. She is also a lifelong athlete, marathon runner, and is passionate about building the next generation of market leaders. Connect with Kim: Kim’s LinkedIn: linkedin.com/in/kimberlystorin Resources Mentioned: Zoom: https://www.zoom.com Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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’s explosive growth, confront the biggest fears leaders have about AI, and explore what the future of work will demand from humans next. Zack Kass is a global AI advisor, keynote speaker, and former Head of Go-To-Market at OpenAI, where he helped bring some of the world’s most transformative AI technologies to market. In this episode, Ilana and Zack will discuss: (00:00) Introduction (02:59) Zack’s Journey to OpenAI (04:46) Understanding Modern AI and Its Evolution (08:03) The Breakthrough of ChatGPT and Its Impact (17:42) Transitioning from OpenAI to New Beginnings (21:21) Challenging Common Misconceptions About AI (28:32) Adaptability in a Rapidly Changing World (34:54) Lessons from Top Innovators (38:15) The Future of Work and Purpose in the Age of AI Zack Kass is a global AI advisor, futurist, speaker, and former Head of Go-To-Market at OpenAI, where he helped bring some of the world’s most transformative AI technologies to market. He now advises global leaders and organizations on how artificial intelligence will reshape work, leadership, and human potential, turning complex ideas into clear, practical insight for the future. His book, The Next Renaissance, offers an optimistic vision of how AI will shape our future. Connect with Zack: Zack’s Website: zackkass.com Zack’s LinkedIn: linkedin.com/in/zackkass Resources Mentioned: Zack’s Book, The Next Renaissance: AI and the Expansion of Human Potential: https://www.amazon.com/dp/1394381085 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment.👉 Grab your ticket before doors close at leapacademy.com/leapcon

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, accountability, and purpose. In this episode, Mick joins Ilana to share the raw story behind that promise, how it shaped his drive to build businesses and high-performing teams, and why leadership starts with something deeper than your “why.” Mick Hunt is a leadership coach, entrepreneur, and speaker known for helping ambitious individuals unlock their full potential. He works with leaders who want to grow their influence, scale their thinking, and build companies and teams that people genuinely believe in and follow. In this episode, Ilana and Mick will discuss: (00:00) Introduction (02:14) How a Traumatic Childhood Built Mick’s Drive (08:48) The Childhood Promise That Defined His Life (10:26) Entrepreneurial Beginnings and Challenges (16:36) His Passion for Building High-Performing Teams (17:14) Why Your ‘Because’ Beats Your ‘Why’ (21:50) The “What If I Fail” Mindset (27:46) Understanding The MICK Factor (30:42) Mick’s Book: How to Be a Good Leader (36:09) The Future of Leadership and Staying Relevant (38:53) The Value of Mentorship (42:28) Daily Practices for Success Mick Hunt is a USA Today bestselling author, international speaker, and leadership expert known for his impact in modern leadership and emotional intelligence. He is the host of the highly rated Mick Unplugged podcast and the author of How to Be a Good Leader When You’ve Never Had One, a modern leadership guide with hands-on insights and actionable frameworks to help you lead with transparency, resilience, and influence. Connect with Mick: Mick’s Website: https://mickhuntofficial.com/ Mick’s LinkedIn: linkedin.com/in/mickhunt Resources Mentioned: Mick’s Book, How to Be a Good Leader When You've Never had One: The Blueprint for Modern Leadership: http://amazon.com/Good-Leader-When-Youve-Never/dp/1394357958 Mick’s Podcast, Mick Unplugged: https://podcasts.apple.com/us/podcast/mick-unplugged/id1731755953 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 worldwide. In this episode, Sheila joins Ilana to discuss her journey of balancing motherhood and a high-powered career, the challenges of building Care.com, and her exciting new venture, Ohai.ai, an AI-powered household assistant. Sheila Lirio Marcelo is the founder of Care.com, an online marketplace for families to find childcare, senior care, pet care, and more. She is also the founder of Ohai, an AI-powered household assistant designed to help reduce the mental load of running a home. In this episode, Ilana and Sheila will discuss: (00:00) Introduction (02:12) Sheila's Childhood and Family Influence (08:04) Struggling to Balance Motherhood and a Career (11:20) Her Journey Into Entrepreneurship and Care.com (14:57) Why Generalists Are Key in Business (18:12) Care.com’s Success: The Power of Testing Ideas (23:34) Building a Two-Sided Marketplace and Gaining Trust (29:44) The Decision to Go Public With Care.com (31:39) Managing Decision-Making and Stress as a Leader (33:38) Reinventing With Ohai AI for Families (40:01) Her Approach to Mental Clarity and Calm (44:44) Embracing Challenges and Personal Growth Sheila Lirio Marcelo is the founder and former CEO of Care.com, the world’s largest online caregiving marketplace, which went public in 2014 and was acquired for $500 million in 2020. After years of leading Care.com through exponential growth, Sheila transitioned into a new chapter, founding Ohai, an AI-powered household assistant designed to help manage various household activities. She is deeply committed to creating solutions that simplify life, improve well-being, and empower families. Connect with Sheila: Sheila’s LinkedIn: linkedin.com/in/sheilamarcelo Sheila’s Instagram: instagram.com/sheilaliriomarcelo Resources Mentioned: Care.com’s Website: https://www.care.com/ Ohai’s Website: https://www.ohai.ai/ Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment.👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 Peloton. Even after being diagnosed with Type 1 diabetes, Robin refused to be defined by anything but her unstoppable drive. In this episode, Robin opens up to Ilana about how she transformed trauma into purpose, made a bold leap into fitness, and became a global force in wellness with Peloton. Robin Arzón is a fitness expert, former lawyer, author, and motivational speaker. She is best known as an instructor at Peloton, where she inspires millions with her high-energy cycling and strength classes. In this episode, Ilana and Robin will discuss: (00:00) Introduction (01:37) Surviving a Hostage Situation (05:47) Discovering Running as a Healing Tool (08:51) From Casual Runs to Ultra-Marathons (11:29) Transitioning from a Law Career to Fitness (13:19) Landing a Job at Peloton with a Cold Email (15:49) Living and Thriving with Type 1 Diabetes (18:34) Juggling a Career, Motherhood, and Life’s Demands (21:39) Pushing Past Her Limits at the StriveX Challenge (24:54) Building a Global Brand Through Consistency (28:18) Swagger Society and Upcoming Cookbook (31:47) Learning to Trust Life’s Redirections Robin Arzón is a fitness expert, former lawyer, author, and motivational speaker. She is best known for inspiring millions with her high-energy cycling and strength classes as an instructor at Peloton, where she is also the Vice President of Fitness Programming. Robin is also a New York Times bestselling author of Shut Up and Run and Strong Mama, sharing her personal stories and fitness philosophies. She advocates for mental and physical strength, promoting the power of movement and mindset to achieve personal transformation. Connect with Robin: Robin’s Website: https://www.robinarzon.com/ Robin’s Instagram: https://www.instagram.com/robinnyc Resources Mentioned: Robin’s Books: Shut Up and Run: How to Get Up, Lace Up, and Sweat with Swagger: https://www.amazon.com/dp/0062445685 Eat to Hustle: 75 High-Protein Plant-Based Recipes (A Cookbook): https://www.amazon.com/dp/031659427X Robin’s Journal, Welcome, Hustler: An Empowerment Journal: https://www.amazon.com/dp/1454946342 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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-growing bootstrapped tech companies in the world. In this episode, Russell joins Ilana to share how he bounced back from his toughest moments, offering powerful lessons in resilience, leadership, and authentic relationships. Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales. In this episode, Ilana and Russell will discuss: (00:00) Introduction (02:04) The Infomercial That Led Him to Entrepreneurship (05:52) The Influence of Wrestling on His Business Drive (08:18) College Days and the Potato Gun Venture (10:15) The Rollercoaster Journey to His First Million (14:48) Key Lessons from His Toughest Year (21:50) The Birth of ClickFunnels and Its Challenges (34:41) Gaining Lifelong Mentorship from Tony Robbins (37:55) Dream 100 Strategy: The Power of Relationships (43:08) Why Vulnerability Can Lead to Unlikely Success (47:14) Tips for Building a Winning Team (50:17) Turning Your Pain into an Asset Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales. Over the past 19 years, he has built a community of over a million entrepreneurs and authored New York Times bestsellers, including DotCom Secrets and Expert Secrets. Connect with Russell: Russell’s Website: www.russellbrunson.com Russell’s LinkedIn: linkedin.com/in/russellbrunson Russell’s Instagram: www.instagram.com/russellbrunson Resources Mentioned: Russell’s YouTube: youtube.com/@russellbrunson The 12 Month Millionaire Droplets: Vincent James's Unmissable Revelations by Vincent James: https://www.amazon.com/dp/B0CXJGPXNN Dig Your Well Before You're Thirsty: The Only Networking Book You'll Ever Need by Harvey Mackay: https://www.amazon.com/dp/0385485468 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 emerging technology and culture. In this episode, Kevin joins Ilana to share how Wired went from fighting for shelf space to redefining what a tech publication could be. He also explains his unique relationship with time, why he tracks the days he has left, and how creators today can thrive with just 1,000 true fans. Kevin Kelly is a writer, photographer, and Senior Maverick at Wired, an award-winning magazine he co-founded in 1993. He is also a former editor and publisher of the Whole Earth Review and the author of multiple bestselling books about the future of technology. In this episode, Ilana and Kevin will discuss: (00:00) Introduction (02:14) Choosing an Unconventional Path to Success (06:34) The Start of His Adventures in Asia (10:54) Getting into Writing and Publishing (14:17) Creating One of the First Hacker Conferences (20:18) The Grit Behind Wired Magazine’s Success (30:37) The Dot-Com Bust and Why Wired was Split (34:17) The Origin and Power of “1,000 True Fans” (41:18) How a Near-Death Experience Transformed Kevin (47:10) About His Latest Book, Colors of Asia Kevin Kelly is a writer, photographer, and co-founder of the award-winning Wired magazine, and a former editor and publisher of the Whole Earth Review. He is the co-chair of The Long Now Foundation, which champions long-term thinking, and the creator of the Cool Tools website, which has reviewed tools daily for over 20 years. Kevin is also the author of multiple bestselling books on the future of technology, and his latest book, Colors of Asia, captures the culture of all 35 Asian countries through vivid photography. Connect with Kevin: Kevin’s Website: https://kk.org Kevin’s Twitter: https://x.com/kevin2kelly Resources Mentioned: Kevin’s Book, Colors of Asia: A Visual Journey: https://www.amazon.com/Colors-Asia-Journey-Kevin-Kelly/dp/B0FGJ18PG5 Leaves of Grass: The Original 1855 Edition by Walt Whitman: https://www.amazon.com/dp/1449505716 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 was brutal, but the lessons shaped everything he did next. In this episode, Jordan reveals to Ilana the real story behind Napster, the personal sacrifices of innovation, and the mindset required to build something that leaves a legacy. Jordan Ritter is a serial entrepreneur, software architect, and angel investor, recognized for his work at Napster, the file-sharing service that reshaped music distribution and digital technology. Since then, he has launched and advised multiple startups in the tech industry. In this episode, Ilana and Jordan will discuss: (00:00) Introduction (02:08) Growing Up on a Farm and Discovering Tech (06:40) His Journey into Hacking and Computer Security (12:37) Joining Napster and Disrupting the Music Industry (17:55) Experiencing Napster’s Highs and Crushing Lows (32:20) Why Jordan Decided to Leave Napster (40:16) Reinventing and Building Companies with Value (46:03) The Importance of Culture in Startups (52:19) Navigating Interviews and Culture Alignment (55:18) The Challenges of Starting a Business (1:03:30) Lessons Learned and Giving Back Jordan Ritter is a serial entrepreneur, software architect, angel investor, and co-founder of Napster, where he helped scale the platform to 60 million users. A four-time founder, he has built 20+ large-scale commercial and open-source products across 12 languages, developing systems used by millions. At Cloudmark, Servio, and Augment AI, Jordan built intuitive, scalable, and reliable platforms, and he now advises CoPilotKit on product strategy. Connect with Jordan: Jordan’s LinkedIn: linkedin.com/in/jordanritter Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 Kawasaki pulls back the curtain on what it really took for Ilana to leap across careers, break barriers, and build a system that helps thousands do the same. She breaks down the concept of reinvention and what it really takes to leap again and again. Ilana Golan is a former F-16 flight instructor turned Silicon Valley tech executive and investor. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. In this episode, Guy and Ilana will discuss: (00:00) Introduction (02:20) Breaking Barriers in the Israeli Air Force (06:07) What Reinvention Really Means Today (10:40) The Core Steps to Reinventing Your Career (12:59) Reinventing When Systems are Against You (15:16) Advice for Women on Breaking Glass Ceilings (19:58) The Core Signals That You Need Reinvention (21:52) Case Studies: Reinventing Public Figures (29:37) The Role of Timing in Reinvention (33:41) The Power of Building a Personal Brand Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana: Ilana’s Website: leapacademy.com Ilana’s LinkedIn: linkedin.com/in/ilanagolan Resources Mentioned: Guy’s Podcast, Remarkable People: https://podcasts.apple.com/us/podcast/guy-kawasakis-remarkable-people/id1483081827 LEAP E97 with Guy Kawasaki: https://podcasts.apple.com/us/podcast/guy-kawasaki-the-tech-evangelist-who-built-apple/id1701718200?i=1000703853865 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 in the U.S. In this episode, Vick opens up to Ilana about the sacrifices, powerful mindset shifts, and relentless drive that transformed his company from the brink of collapse to industry leadership. Vick Tipnes is the founder and CEO of Blackstone Medical Services, a leading provider of home sleep testing. Under his leadership, the company has earned recognition five times on the Inc. 5000 list. In this episode, Ilana and Vick will discuss: (00:00) Introduction (02:03) Growing Up with an Entrepreneurial Father (04:35) Leaving College To Chase Entrepreneurship (06:32) Losing Both Parents and Transitioning to Healthcare (10:45) Exiting the Radiology Business with Almost Nothing (15:34) Being Divorced, Broke, and Starting All Over (19:30) Building Blackstone Medical Services from Scratch (23:27) Achieving Success After Years of Losing Money (31:27) How Vick Manages His Career Without Burning Out (33:07) Investing in Identity and Personal Growth (36:06) Addressing Sleep Issues and Health Solutions (38:18) The Power of Tenacity and Refusing To Quit Vick Tipnes is a self-made entrepreneur, author, and mentor, best known as the founder and CEO of Blackstone Medical Services, a leading provider of home sleep testing. Under his leadership, the company has earned recognition five times on the Inc. 5000 list. Vick is also the founder of Tipnes Capital and Tipnes Health and the author of Did You Sell Your Soul?, where he shares insights on overcoming obstacles, staying focused, and achieving life goals. Connect with Vick: Vick’s Website: vicktipnes.com Vick’s LinkedIn: linkedin.com/in/vicktipnes Vick’s Instagram: instagram.com/vicktipnes Resources Mentioned: Vick’s Book, Did You Sell Your Soul?: It's Never Too Late to Change Your Story: https://www.amazon.com/dp/1662903766 Leap Academy:LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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 Companies. In this episode, John joins Ilana to reveal how to build a career from the ground up, reinvent after setbacks, and lead with the kind of creativity that transforms industries. John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, and more into a multi-billion-dollar global powerhouse. In this episode, Ilana and John will discuss: (00:00) Introduction (02:38) His Early Exposure to Fashion and Design (06:36) Choosing Stanford Over the Ivy Leagues (09:26) Getting Started in the Beauty Industry (15:35) The Power of Learning Every Role in the Business (24:11) Joining Estee Lauder and Moving to LA (28:42) Building MAC Cosmetics into a Global Powerhouse (36:02) How John Landed Celebrity Endorsements (42:56) Working with Tom Ford and Revolutionizing Fragrances (52:58) Navigating Controversy and Reinventing Himself (1:01:17) His New Ventures and Future Plans John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, Smashbox, Clinique, and Jo Malone London. Over his 30-year career at Estée Lauder, he played a pivotal role in expanding the company into a multi-billion-dollar business across both established and emerging markets. He is the author of Behind the Blue Door, a visual memoir capturing his bold lifestyle, vibrant career, and personal journey. Connect with John: John’s Instagram: instagram.com/jdemsey John’s LinkedIn: linkedin.com/in/john-demsey Resources Mentioned: John’s Book, Behind the Blue Door: A Maximalist Mantra: https://www.amazon.com/dp/0865654344 LEAP E57 with Dan Ariely: https://podcasts.apple.com/us/podcast/surviving-lies-rumors-and-digital-hate-dan-arielys/id1701718200?i=1000678512628 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 female founder, from enduring 107 rejections to breaking global crowdfunding records and facing the backlash that followed. She shares what it truly takes to scale a mission-driven company, rise above bias, and empower women financially on a global scale. Anna-Sophie Hartvigsen is an entrepreneur, investor, and co-founder of Female Invest, a financial education platform that has empowered women across more than 100 countries. She’s a leading voice in closing the financial gender gap through education, representation, and access. In this episode, Ilana and Anna will discuss: (00:00) Introduction (02:51) Her Early Interest in Finance and Investing (05:15) Turning Down McKinsey to Build Female Invest (09:10) Challenges and Misconceptions in Entrepreneurship (11:07) Launching a Facebook Group That Grew Like Wildfire (13:35) Why Money for Women Is Deeply Political (15:29) Bootstrapping to Success After Near Bankruptcy (22:14) Anna’s Y Combinator Experience (25:02) The Reality of Fundraising as a Female Founder (30:35) Raising $24M After 107 Rejections (34:01) Facing Backlash, Anxiety, and Hate (38:08) The Biggest Financial Mistakes Women Make (44:12) Lessons and Advice for Founders Anna-Sophie Hartvigsen is a Danish entrepreneur, investor, and co-founder of Female Invest, a financial education platform that has empowered women across more than 100 countries. A Forbes 30 Under 30 recipient, she helped bootstrap Female Invest from a small Facebook group into one of the most engaged financial communities in the world. Anna is also the bestselling author of Girls Just Wanna Have Funds and a leading voice in closing the financial gender gap through education, representation, and access. Connect with Anna: Anna’s LinkedIn: linkedin.com/in/anna-hartvigsen-46352611a Anna’s Instagram: instagram.com/anna.hartvigsen Resources Mentioned: Female Invest: https://www.femaleinvest.com Anna’s Book, Girls Just Wanna Have Funds: A Feminist's Guide to Investing: https://www.amazon.com/dp/0744077303 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 80 bestselling books. In this episode, Brian shares the principles and habits that turned his life around, from the one skill that made him ten times richer to the $1.50 notebook that can make you a millionaire. He breaks down the secret to wealth and how to stay laser-focused on your biggest goals. Brian Tracy is the Chairman and CEO of Brian Tracy International. He is a prolific businessman, renowned speaker, and bestselling author of over 80 books, including his latest, The 32 Unbreakable Laws of Money and Success. In this episode, Ilana and Brian will discuss: (00:00) Introduction (01:37) From Washing Floors to Mastering Sales (06:57) MMM Principle: The Key to Making More Money (10:58) Financial Lessons from Business Giants (15:17) The Golden Triangle of Leadership (18:25) Activating the Superconscious Mind (24:30) The Goal-Setting Exercise That Built Millionaires (33:21) Hiring Your Dream Team with the 3x3x3 Method (42:28) Crushing Financial Fears and “Excusitis” (48:36) The Unbreakable Laws of Money and Success (1:01:22) How to Actually Learn About Money (1:05:21) The Seven Steps to Increase Productivity and Income Brian Tracy is a renowned speaker, bestselling author, and the Chairman and CEO of Brian Tracy International. He trains individuals and organizations to achieve their personal and business goals more effectively. Brian has had successful careers in sales and marketing, investments, real estate development and syndication, importation, distribution, and management consulting. He has authored over 80 books, including bestsellers, Eat That Frog and The Success Secrets of Self-Made Millionaires, and the latest, The 32 Unbreakable Laws of Money and Success. Connect with Brian: Brian’s Website: https://www.briantracy.com/ Brian’s LinkedIn: linkedin.com/company/brian-tracy-international Resources Mentioned: Brian’s Books: The 32 Unbreakable Laws of Money and Success: Transform Your Life and Unlock Your Unlimited Potential: https://www.amazon.com/dp/1523007001 Eat That Frog!: 21 Great Ways to Stop Procrastinating and Get More Done in Less Time: https://www.amazon.com/dp/162656941X The 21 Success Secrets of Self-Made Millionaires: How to Achieve Financial Independence Faster and Easier than You Ever Thought Possible: https://www.amazon.com/dp/0369307534 Think and Grow Rich by Napoleon Hill: https://www.amazon.com/dp/1585424331 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 the red. Instead of retreating, she climbed again, leading one of retail’s greatest comebacks. In this episode, Sharon shares how to face fear with curiosity, lead with heart, and use storytelling to spark transformation in business and life. Sharon Price John is the President and CEO of Build-A-Bear Workshop, where she led one of retail’s most inspiring turnarounds. She is also the author of Stories & Heart and Chair of the Toy Association. In this episode, Ilana and Sharon discuss (00:00) Introduction (02:17) The Truth Behind Every “Overnight” Success (03:53) The Tree That Taught Her Courage (07:16) Breaking Into Advertising (13:49) Climbing the Ladder at Mattel (19:41) When Her Startup Collapsed (28:55) Leading a Turnaround When Everything Seems Lost (32:44) The One Rule Every Great Leader Lives By (33:40) Avoiding the Mistakes That Cost You Most (38:12) The Strategy That Saved Build-A-Bear (50:57) Leading With Courage and Clarity Through Crisis(01:04:33) Storytelling as the Heart of Great Leadership Sharon Price John has served as President and CEO of Build-A-Bear Workshop since 2013, leading the brand from a $49 million loss to record profitability. Before Build-A-Bear, she held senior roles at Hasbro, Mattel, and Stride Rite Children’s Group, earning a reputation as a turnaround expert. Sharon is the author of Stories & Heart and serves on the boards of Jack in the Box and First Book. She is also Chair of the Toy Association. Connect with Sharon: Sharon’s LinkedIn: linkedin.com/in/sharon-price-john-26239820 Sharon’s Website: storiesandheart.com Resources Mentioned: Sharon’s Book, Stories & Heart: Unlock the Power of Personal Stories to Create a Life You Love: https://www.amazon.com/dp/1950863441 First Book: https://firstbook.org Build-A-Bear Workshop: https://www.buildabear.com Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 community that built the impossible. He breaks down why the best ideas come from doing something interesting, not chasing money. Jimmy Wales is the co-founder of Wikipedia and the founder of the Wikimedia Foundation, the nonprofit that supports Wikipedia and its sister projects. He also co-founded Fandom (formerly Wikia), one of the web’s largest community platforms. In this episode, Ilana and Jimmy discuss: (00:00) Introduction (02:31) How Childhood Curiosity Sparked Wikipedia’s Vision (05:59) Turning Crisis Into Innovation During the Dotcom Crash (08:08) The Creation of Wikipedia (14:19) The Power of Community When Capital Runs Out (20:14) Why Jimmy Refused to Monetize Wikipedia (29:54) Early Fundraising Efforts for Wikipedia (34:21) What Makes Someone Truly Notable on Wikipedia (39:11) AI’s Role in Wikipedia's Future (46:15) Inside The Seven Rules of Trust (57:17) Jimmy’s Ultimate Advice to Just Start Jimmy Wales is the co-founder of Wikipedia, the world’s largest free encyclopedia, and Wikimedia Foundation, the nonprofit that supports it. An advocate for open, collaborative knowledge sharing, he has empowered millions to contribute to a global resource of information. Recognized by TIME as one of the 100 Most Influential People in the World, Jimmy is also the author of The Seven Rules of Trust, where he shares the principles that guided his journey and offers insights on building lasting endeavors. Connect with Jimmy: Jimmy’s Twitter: x.com/jimmy_wales Jimmy’s LinkedIn: linkedin.com/in/jimmy-wales-919a8b Resources Mentioned: Wikipedia: https://www.wikipedia.org/ Jimmy’s book, The Seven Rules of Trust: A Blueprint for Building Things That Last: https://www.amazon.com/dp/0593727460 Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence: https://www.amazon.com/dp/0143115766 LEAP E122 with Nathan Blecharczyk: https://podcasts.apple.com/us/podcast/nathan-blecharczyk-the-raw-truth-of-scaling-airbnb/id1701718200?i=1000723574008 Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out our free training today at https://bit.ly/leap--free-training

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 it takes to see opportunity before the world does and how to keep building, no matter the odds or the decade. Joe Foster is the co-founder of Reebok, the small family startup that became one of the world’s most iconic sports brands. Ben Weiss is the founder and CEO of Syntilay, a footwear innovation company building the future of sneakers through AI design and 3D printing. Together, their partnership is transforming the footwear industry. In this episode, Ilana, Ben, and Joe discuss: (00:00) Introduction (03:50) The Birth of Reebok (09:59) Breaking into the U.S. Market Against All Odds (19:04) How Women Skyrocketed Reebok’s Success (20:19) Hollywood and the Rise of Reebok (23:04) Facing Challenges with Optimism (25:27) Syntilay: A New Concept in AI Footwear (28:30) Persistence and White Space Thinking (32:56) Innovating with AI and 3D Printing (36:17) The Future of Footwear and Technology (41:41) Advice for Aspiring Entrepreneurs Joe Foster is the co-founder of Reebok, the small startup he and his brother Jeff built into one of the world’s most iconic sports brands. Through innovation and perfect timing, he helped turn Reebok into a global household name. After stepping away, he authored the bestselling memoir Shoemaker and launched the How to Survive & Thrive series, now in its fourth edition. At 90, he continues to speak worldwide and mentor founders, sharing enduring lessons on creativity, resilience, and reinvention. Ben Weiss is the founder of Syntilay, a Florida-based startup pioneering AI-designed, 3D-printed sneakers. With advisors like Reebok founder Joe Foster and original Shark Tank investor Kevin Harrington, Ben is redefining how shoes are created through technology, speed, and personalization. His mission is to empower creators to design and own their own footwear brands. Connect with Joe and Ben: Joe’s LinkedIn: linkedin.com/in/joe-foster-a38a4b10b Ben’s LinkedIn: linkedin.com/in/benxweiss/ Resources: Syntilay: https://syntilay.com/ Joe’s Book, Shoemaker: The Untold Story of the British Family Firm that Became a Global Brand: https://www.amazon.com/dp/1471194019 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 his book The Innovation Stack, a blueprint for building a business that cannot be copied. In this episode, Jim joins Ilana to reveal the secret to creating an unbeatable business, why ignorance can be a superpower, and how to survive the impossible as an entrepreneur. Jim McKelvey is the co-founder of Square (now Block), a billionaire entrepreneur, and author of The Innovation Stack. He also founded LaunchCode, a nonprofit providing free tech education and job placement. In this episode, Ilana and Jim will discuss: (00:00) Introduction (02:04) Growing Up as an ‘Uncool’ Kid in St. Louis (04:01) The Early Hustle That Jumpstarted His Career (07:47) Launching a Business with 15-Year-Old Jack Dorsey (13:50) The Birth of Square: From Glass Blowing to FinTech (20:09) The Art of Selling and Capturing Attention (26:48) How a Single Demo Won Over MasterCard (31:04) Amazon's Failed Attempt to Crush Square (32:17) The Innovation Stack: Building an Unbeatable Business (35:55) Why Most Entrepreneurs Give Up Too Soon (41:32) Why the Best Innovators Are Always “Unqualified” Jim McKelvey is a serial entrepreneur, inventor, and philanthropist best known as the co-founder of Square (now Block), the fintech company that redefined digital payments. He is the author of The Innovation Stack, which explores how companies can survive by creating solutions that can’t be copied. Jim also founded LaunchCode, a nonprofit that provides free tech education and job placement for aspiring coders. Connect with Jim Jim’s LinkedIn: linkedin.com/in/mckelveyjim Resources Mentioned Jim’s Book, The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time: https://www.amazon.com/Innovation-Stack-Building-Unbeatable-Business/dp/0593086732 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 the world, and why she embraces rejection as a growth strategy. She breaks down the tension between patience and urgency, the power of finding joy in pursuing one’s passions, and how to choose partners who amplify your mission. Kara Nortman is the co-founder of Angel City FC and managing partner of Monarch Collective, a $250M investment platform driving the growth of women’s sports. A former investor at Upfront Ventures and operator at IAC, Kara brings decades of experience turning bold ideas into lasting movements. In this episode, Ilana and Kara will discuss: (00:00) Introduction (02:03) Realizing the Market Gap in Women’s Sports (04:16) Turning Inspiration into Action (06:44) Finding Joy Through Volunteering and Community (11:54) The Birth of Angel City FC (17:23) Turning Rejection into Fuel (30:48) Breaking into the World of Venture Capital (31:42) Game-Changing Mentorship and Early Career Lessons (33:47) Discovering a Passion for Tech at Battery Ventures (44:19) Building Angel City and Redefining the Playbook (50:04) Launching Monarch and Scaling the Movement Kara Nortman is an investor, founder, and sports operator focused on advancing the women’s sports economy. As a co-founder of the professional women's soccer team, Angel City FC, she pioneered a community-first 10% sponsorship model that drove significant commercial success. Kara co-leads Monarch Collective, investing in women’s sports teams and related businesses across the U.S. and Europe. Previously, she was a managing partner at Upfront Ventures and an executive at IAC, where she helped incubate Tinder through Hatch Labs. Connect with Kara: Kara’s LinkedIn: linkedin.com/in/karanortman Resources Mentioned: Monarch Collective: https://monarchcoll.com Angel City FC: https://angelcity.com Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 episode, Robert returns to the show to share how childhood struggles shaped his values, why passion is developed, not discovered, and how to know if you’re climbing the wrong mountain in life. He also reveals the frameworks from his new book to help you align your career, relationships, and purpose with your deepest values. Robert Glazer is a serial entrepreneur, bestselling author, and global keynote speaker. He founded Acceleration Partners, a 300-person marketing agency, and is the author of eight books, including Elevate and his newest release, The Compass Within. In this episode, Ilana and Robert discuss: (00:00) Introduction (02:09) Growing Up as the “Underachiever” Kid (05:20) Discovering a Love for Learning in College (09:00) How Helping One Company Sparked an Agency (10:30) The Health Scare That Sparked a Wake-Up Call (14:18) Leading with Transparency During COVID (16:56) Choosing to Step Aside as CEO (19:29) Writing The Compass Within as a Story (22:00) Understanding Core Values (26:09) The Three Climbs of Success for High Achievers (29:12) Six Questions to Identify Your Core Values Robert Glazer is an entrepreneur, bestselling author, and thought leader on business and personal growth. He founded Acceleration Partners, scaling it into a 300-person agency recognized for its values-driven culture. Robert is the author of eight books, including Elevate and The Compass Within, and the Friday Forward newsletter. Known for his insights on leadership, capacity building, and core values, he speaks on stages around the globe and helps individuals and organizations align success with authenticity. Connect with Robert Robert’s Website: robertglazer.com Robert’s LinkedIn: linkedin.com/in/glazer The Compass Within Website: compass-within.com Resources Mentioned LEAP Episode 32 with Robert Glazer: https://podcasts.apple.com/us/podcast/the-art-of-reinvention-how-to-elevate-your-career/id1701718200?i=1000660153819 The Six Core Values Questions: robertglazer.com/six Robert’s Book, The Compass Within: A Little Story About the Values That Guide Us: https://geni.us/values Free Course: robertglazer.com/compass-leap Robert’s Book, Elevate: Push Beyond Your Limits and Unlock Success in Yourself and Others: https://www.amazon.com/Elevate-Beyond-Limits-Success-Yourself/dp/1492691488 The Freak Factor: Discovering Uniqueness by Flaunting Weakness by David Rendall: https://www.amazon.com/Freak-Factor-Discovering-Uniqueness-Flaunting/dp/1599326698 Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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 ever led by a Black woman in the U.S. In this episode, Thai joins Ilana to share the lessons she’s learned throughout her career, from her time at Sony, Facebook, and Lionsgate. She also opens up about her personal struggles with fertility while building a successful career and the pivotal moments that shaped her leadership style. Thai Randolph is an award-winning entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. In this episode, Ilana and Thai discuss: (00:00) Introduction (01:51) How Thai’s Small-Town Roots Shaped Her Path (04:58) Pivoting from Marketing Missiles to Storytelling (09:36) Breaking into Big Tech: From Sony to Facebook (14:14) Balancing Fertility Struggles and Career Moves (22:11) Joining Lionsgate and Meeting Kevin Hart (26:34) Challenges of Carving Out a New Business (28:20) Raising $100M for Hartbeat Against All Odds (32:40) Transitioning to CEO and Leadership Lessons (37:49) Balancing Work, Life, and Avoiding Burnout (41:57) Redefining Your Identity Beyond the Job Title (49:28) Thai’s Next Big Ventures and Future Plans Thai Randolph is an entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. As President and COO of Laugh Out Loud, she oversees the strategy and operations for Kevin Hart’s comedy network. Thai has driven digital transformation at companies like Facebook and Sony, and provided media strategy for top brands like Verizon, Dell, and more. Connect with Thai: Thai’s LinkedIn: linkedin.com/in/thairandolph Thai’s Instagram: instagram.com/thairandolph Resources Mentioned: Thai’s Podcast, The Suga: podcasts.apple.com/us/podcast/the-suga/id1502324399 LOL Network: youtube.com/@lolnetwork Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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, Lisa opens up to Ilana about breaking free from cultural expectations, showing up authentically in the face of criticism, and how you can build radical confidence without needing external validation. Lisa Bilyeu is an entrepreneur, bestselling author, and co-founder of Quest Nutrition, a multi-billion-dollar company. Her mission is to use content creation to empower women to break free from limiting beliefs and build extraordinary lives. In this episode, Ilana and Lisa will discuss: (00:00) Introduction (02:22) Her Upbringing and the Weight of Expectations (06:44) Velvet Handcuffs: The Trap of People Pleasing (10:55) Transitioning from Housewife to Co-Founder (19:13) Handling Your Emotions in Business (24:25) How Lisa Tackles Online Hate and Criticism (33:12) The Three Keys to Mission-Driven Content Creation (37:25) Lisa’s No-BS Guide to Success (44:40) Why She Chose Her Mission Over Motherhood (1:03:06) Building Radical Confidence Through Self-Reliance Lisa Bilyeu is an entrepreneur, author, and co-founder of Quest Nutrition, a multi-billion-dollar company that transformed the health and wellness industry. She is also the founder and host of Women of Impact, co-founder of Impact Theory, and bestselling author of Radical Confidence. Lisa’s mission is to use content creation to empower women to break free from limiting beliefs and embrace their full potential. Connect with Lisa: Lisa’s Website: https://lisabilyeu.com/ Lisa’s YouTube: www.youtube.com/@LisaBilyeu Lisa’s Instagram: https://www.instagram.com/lisabilyeu Resources Mentioned: Lisa’s Book, Radical Confidence: 11 Lessons on How to Get the Relationship, Career, and Life You Want: https://www.amazon.com/dp/B09JPHK9C3 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training