Episodios

  • From Homeless Shelter to Building a Billion-Dollar Mortgage Company | Damian Maldonado | E146

    From Homeless Shelter to Building a Billion-Dollar Mortgage Company | Damian Maldonado | E146
    Feb 19 2026
    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: 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
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    53 m
  • From Pastor to Million-Dollar Days: Eileen Wilder on Charging Your Worth | E145

    From Pastor to Million-Dollar Days: Eileen Wilder on Charging Your Worth | E145
    Feb 17 2026
    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
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    56 m
  • Inc. & Fast Company CEO: How Stephanie Mehta Redefined the Path from Editor to CEO | E144

    Inc. & Fast Company CEO: How Stephanie Mehta Redefined the Path from Editor to CEO | E144
    Feb 10 2026
    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
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    1 h y 1 m
  • Zoom CMO Kim Storin on Leading Through Brand Change When the Stakes Are High | E143

    Zoom CMO Kim Storin on Leading Through Brand Change When the Stakes Are High | E143
    Feb 3 2026
    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
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    49 m
  • OpenAI's Former Head of GTM: What Leaders Get Wrong About AI & What’s Coming Next | Zack Kass | E142

    OpenAI's Former Head of GTM: What Leaders Get Wrong About AI & What’s Coming Next | Zack Kass | E142
    Jan 27 2026
    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
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    52 m
  • From Childhood Trauma to Building High-Performance Leaders | Mick Hunt | E141

    From Childhood Trauma to Building High-Performance Leaders | Mick Hunt | E141
    Jan 20 2026
    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
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    48 m
  • Care.com Founder Sheila Lirio Marcelo: How a Struggling Mom Built a Million Dollar Caregiving Empire | E140

    Care.com Founder Sheila Lirio Marcelo: How a Struggling Mom Built a Million Dollar Caregiving Empire | E140
    Jan 13 2026
    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
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    53 m
  • Peloton’s Robin Arzón: From Hostage Survivor to Fitness Icon Inspiring Millions

    Peloton’s Robin Arzón: From Hostage Survivor to Fitness Icon Inspiring Millions
    Jan 6 2026
    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
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    43 m