Leap Academy with Ilana Golan

Jordan Ritter, a serial entrepreneur and co-founder of Napster, shares his journey from a tech-illiterate farm boy to a pivotal player in the music industry's digital revolution. He recounts the exhilarating rise of Napster, the relentless hustle behind its backend, and the chaotic legal battles that ensued. Jordan reflects on the lessons learned from innovation's sacrifices, the significance of company culture in startups, and his commitment to mentoring the next generation of tech founders. Tune in for insights on disruption and perseverance!

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

Anna-Sophie Hartvigsen, co-founder of Female Invest, shares her inspiring journey from facing rejection at a bank to building a financial education platform for women. She discusses the challenges of fundraising as a female founder, including enduring 107 rejections and breaking crowdfunding records with a $24M raise. Anna emphasizes the political nature of financial independence for women and highlights her innovative strategies for growth, including transforming a small Facebook group into a global community, empowering women across over 100 countries.

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 

Sharon Price John, President and CEO of Build-A-Bear Workshop and author of Stories & Heart, shares her journey through retail challenges. She discusses how climbing a tree as a child taught her the value of courage and resilience. Sharon reveals her bold moves in advertising and the lessons learned from a failed startup. Her two-step turnaround framework emphasizes eliminating wasteful habits. With impactful storytelling, she reshaped Build-A-Bear's mission, leading the company to profitability and expansion, all while navigating the complexities of leadership during crisis.

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