Leap Academy with Ilana Golan

Ra’anan Cohen walked into the tech world with no fancy degree and no startup pedigree; just a phone call from a friend and the promise of free food and a gym membership. From day one, he felt like an outsider, constantly battling imposter syndrome. Yet, he stuck with it, learned the ropes of the startup world, and ultimately founded a billion-dollar company. In this episode, Ra’anan joins Ilana to share his wild 15-year ride: a public company on NASDAQ, a unicorn valued at $1 billion, and a board that tried to fire him at his peak. He reveals everything the startup world doesn't want you to know about the real cost of chasing unicorns. Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was also the founder and CEO of MobileMax, which went public on NASDAQ. In this episode, Ilana and Ra’anan will discuss: (00:00) Introduction (04:30) The Biggest False Beliefs On Entrepreneurship (06:38) The Impact of Imposter Syndrome on Ra'anan's Career (09:16) Quitting a Stable Job to Start a Company (12:09) Raising Capital with No Credentials (15:34) The $10M Mistake That Cost Him Everything (18:55) How a Pizza Night Sparked a Billion-Dollar Idea (24:35) Raising Capital the Second Time: The Stealth Mode Strategy (28:47) Different Types of Modern Investors (32:52) Why Startups Are Marathons, Not Rollercoasters (43:43) When to Make Life-Changing Decisions (and When Not To) (45:39) Redefining Success: The Multi-Bucket Life Philosophy (53:36) Q&A: Handling Rejection Without Losing Your Spark Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was the founder and CEO of MobileMax, where he led the company to multimillion-dollar international sales and an IPO. Ra'anan is also the author of Confessions of a Unicorn Founder, a national bestseller in Israel, which is currently being adapted into a TV series. Connect with Ra’anan: Ra’anan’s Website: https://www.raanancohen.com Ra’anan’s LinkedIn: linkedin.com/in/raananc Resources Mentioned: Ra’anan’s Book, Confessions of a Unicorn Founder: Obsession, Greed, and the Brutal Truth Behind Chasing the Startup Dream: https://www.raanancohen.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 Kim Perell was fired, she had to fire all her friends on the same day. The company she thought would make her a millionaire had just gone bankrupt, leaving her with no income or backup plan. Instead of giving up, she took a $10,000 loan from her grandmother to start her first company from her kitchen table. That bet led to a $20 million exit and eventually, a $235 million company. In this episode, Kim joins Ilana to share how to turn setbacks and mistakes into million-dollar breakthroughs and how to overcome the limiting beliefs holding you back. She also reveals the four pillars that helped her achieve success without burning out. Kim Perell is a 9x founder, 3x bestselling author, and investor in 100+ companies. Kim became a multi-millionaire by the time she was 30, and sold her last company for $235 million to Singtel, while simultaneously running multi-million-dollar companies. In this episode, Ilana and Kim will discuss: (00:00) Introduction (04:08) Growing Up in the Shadow of Her Twin Sister (07:07) Learning Risk and Failure from Entrepreneur Parents (09:46) How Getting Fired Led to a Career Pivot (13:31) Her Grandma’s Life-Changing $10K Loan (16:37) Using The 70% Rule to Make Business Decisions (18:48) The Four Pillars of Business Success (23:50) Selling Her Business for $20 Million (28:02) Building a Money Mindset (30:59) The Dangers of Failing to Pivot Or Make Mistakes (40:13) Teaching Your Children Resilience (45:01) Q&A: How to Chase Success Despite Fear Kim Perell is a 9-time founder, 3-time bestselling author, top keynote speaker, and investor in over 100 companies. Her book, Mistakes That Made Me a Millionaire, offers a transformative guide to turning setbacks into million-dollar opportunities. An award-winning entrepreneur, Kim has appeared on major platforms and serves as a judge for Entrepreneur Magazine’s Elevator Pitch. She is dedicated to empowering the next generation of business leaders for success. Connect with Kim: Kim’s Website: https://kimperell.com/ Kim’s LinkedIn: https://www.linkedin.com/in/kimperell/ Kim’s Instagram: https://www.instagram.com/kimperell/ Resources Mentioned: Kim’s Book, Mistakes that Made Me a Millionaire: How to Transform Setbacks into Extraordinary Success: https://www.amazon.com/dp/1637747128 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

Jason Fried didn’t follow the startup rules most founders swear by. He rejected venture capital, refused to chase growth at all costs, and chose to stay small on purpose. What started as a scrappy web design agency turned into Basecamp, a multi-million-dollar business built on profitability, simplicity, and conviction. In this episode, Jason joins Ilana to challenge everything you think you know about scaling a business. He also opens up about how a single leadership decision caused 30% of his company to quit overnight, and how staying principled ultimately made the company stronger. Jason Fried is the co-founder and CEO of 37signals, the company behind Basecamp and HEY. For over 27 years, he has grown Basecamp into a multi-million dollar business without ever taking venture capital or chasing aggressive growth targets. In this episode, Ilana and Jason will discuss: (00:00) Introduction (03:18) Lessons from Selling Stereo Equipment as a Kid (06:58) Starting 37signals from Scratch (14:13) Pivoting to Software Through Basecamp (16:41) The Perks of Being a Small Company (27:24) The Policy That Made 30% of the Company Quit (31:45) Surviving the Backlash and Rebuilding the Team (39:21) Building Thicker Skin as a Leader (42:43) How to Incorporate AI Without Getting Carried Away (45:15) How Basecamp Is Reinventing Itself with Version 5 (48:56) Why Jason Won’t Advise His Younger Self (54:07) Q&A: How to Decide Your Next Career Move Jason Fried is a co-founder and CEO of 37signals, the makers of Basecamp. He is a bestselling author of Rework and It Doesn’t Have to Be Crazy at Work. Known for his contrarian approach to entrepreneurship, Jason emphasizes simplicity, profitability, and long-term thinking. For over 27 years, he has grown Basecamp into a multi-million dollar, fully profitable business without ever taking venture capital or chasing aggressive growth targets. Connect with Jason: LinkedIn: linkedin.com/in/jason-fried X: https://x.com/jasonfried Resources Mentioned: Jason’s Books: Rework: https://www.amazon.com/Rework-Jason-Fried/dp/0307463745 It Doesn't Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780 37signals’ Website: https://37signals.com Basecamp’s Website: https://basecamp.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

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: 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: 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