The Untold Story of Napster's Success, Collapse & Hard-Won Lessons | Jordan Ritter | E138

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

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: 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 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: 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

John Demsey didn’t become a powerhouse in the beauty industry by a mere stroke of luck; he built that influence on retail floors, taking on scrappy roles while learning the business in ways no MBA could ever teach. This helped him scale MAC Cosmetics into a global cultural movement, shape some of the most iconic beauty brands of our time, and ultimately rise to Group President of Estée Lauder Companies. In this episode, John joins Ilana to reveal how to build a career from the ground up, reinvent after setbacks, and lead with the kind of creativity that transforms industries. John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, and more into a multi-billion-dollar global powerhouse. In this episode, Ilana and John will discuss: (00:00) Introduction  (02:38) His Early Exposure to Fashion and Design (06:36) Choosing Stanford Over the Ivy Leagues (09:26) Getting Started in the Beauty Industry (15:35) The Power of Learning Every Role in the Business (24:11) Joining Estee Lauder and Moving to LA (28:42) Building MAC Cosmetics into a Global Powerhouse  (36:02) How John Landed Celebrity Endorsements (42:56) Working with Tom Ford and Revolutionizing Fragrances (52:58) Navigating Controversy and Reinventing Himself (1:01:17) His New Ventures and Future Plans John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, Smashbox, Clinique, and Jo Malone London. Over his 30-year career at Estée Lauder, he played a pivotal role in expanding the company into a multi-billion-dollar business across both established and emerging markets. He is the author of Behind the Blue Door, a visual memoir capturing his bold lifestyle, vibrant career, and personal journey. Connect with John: John’s Instagram: instagram.com/jdemsey  John’s LinkedIn: linkedin.com/in/john-demsey  Resources Mentioned: John’s Book, Behind the Blue Door: A Maximalist Mantra: https://www.amazon.com/dp/0865654344  LEAP E57 with Dan Ariely: https://podcasts.apple.com/us/podcast/surviving-lies-rumors-and-digital-hate-dan-arielys/id1701718200?i=1000678512628  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

When 19-year-old Anna-Sophie Hartvigsen walked into a bank hoping to secure a loan to buy a property, she was denied on the spot. That “no” pushed her into investing and ultimately led her to co-found Female Invest, a global platform empowering women to take control of their financial futures. In this episode, Anna joins Ilana for a raw, honest conversation about the reality of fundraising as a female founder, from enduring 107 rejections to breaking global crowdfunding records and facing the backlash that followed. She shares what it truly takes to scale a mission-driven company, rise above bias, and empower women financially on a global scale. Anna-Sophie Hartvigsen is an entrepreneur, investor, and co-founder of Female Invest, a financial education platform that has empowered women across more than 100 countries. She’s a leading voice in closing the financial gender gap through education, representation, and access. In this episode, Ilana and Anna will discuss: (00:00) Introduction  (02:51) Her Early Interest in Finance and Investing (05:15) Turning Down McKinsey to Build Female Invest (09:10) Challenges and Misconceptions in Entrepreneurship (11:07) Launching a Facebook Group That Grew Like Wildfire (13:35) Why Money for Women Is Deeply Political (15:29) Bootstrapping to Success After Near Bankruptcy (22:14) Anna’s Y Combinator Experience (25:02) The Reality of Fundraising as a Female Founder (30:35) Raising $24M After 107 Rejections (34:01) Facing Backlash, Anxiety, and Hate (38:08) The Biggest Financial Mistakes Women Make (44:12) Lessons and Advice for Founders Anna-Sophie Hartvigsen is a Danish entrepreneur, investor, and co-founder of Female Invest, a financial education platform that has empowered women across more than 100 countries. A Forbes 30 Under 30 recipient, she helped bootstrap Female Invest from a small Facebook group into one of the most engaged financial communities in the world. Anna is also the bestselling author of Girls Just Wanna Have Funds and a leading voice in closing the financial gender gap through education, representation, and access. Connect with Anna: Anna’s LinkedIn: linkedin.com/in/anna-hartvigsen-46352611a  Anna’s Instagram: instagram.com/anna.hartvigsen  Resources Mentioned: Female Invest: https://www.femaleinvest.com  Anna’s Book, Girls Just Wanna Have Funds: A Feminist's Guide to Investing: https://www.amazon.com/dp/0744077303  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Brian Tracy was fired from washing dishes, cars, and floors, and began to believe that “washing things” might be his destiny. But when he learned that the top 20% in any field earn 80% of the money, he committed to becoming one of them. That decision transformed him from a broke high school dropout into a global authority on success, speaking to millions across 84 countries and writing more than 80 bestselling books. In this episode, Brian shares the principles and habits that turned his life around, from the one skill that made him ten times richer to the $1.50 notebook that can make you a millionaire. He breaks down the secret to wealth and how to stay laser-focused on your biggest goals. Brian Tracy is the Chairman and CEO of Brian Tracy International. He is a prolific businessman, renowned speaker, and bestselling author of over 80 books, including his latest, The 32 Unbreakable Laws of Money and Success. In this episode, Ilana and Brian will discuss: (00:00) Introduction (01:37) From Washing Floors to Mastering Sales (06:57) MMM Principle: The Key to Making More Money (10:58) Financial Lessons from Business Giants (15:17) The Golden Triangle of Leadership (18:25) Activating the Superconscious Mind (24:30) The Goal-Setting Exercise That Built Millionaires (33:21) Hiring Your Dream Team with the 3x3x3 Method (42:28) Crushing Financial Fears and “Excusitis” (48:36)  The Unbreakable Laws of Money and Success (1:01:22) How to Actually Learn About Money (1:05:21) The Seven Steps to Increase Productivity and Income Brian Tracy is a renowned speaker, bestselling author, and the Chairman and CEO of Brian Tracy International. He trains individuals and organizations to achieve their personal and business goals more effectively. Brian has had successful careers in sales and marketing, investments, real estate development and syndication, importation, distribution, and management consulting. He has authored over 80 books, including bestsellers, Eat That Frog and The Success Secrets of Self-Made Millionaires, and the latest, The 32 Unbreakable Laws of Money and Success. Connect with Brian: Brian’s Website: https://www.briantracy.com/  Brian’s LinkedIn: linkedin.com/company/brian-tracy-international Resources Mentioned: Brian’s Books: The 32 Unbreakable Laws of Money and Success: Transform Your Life and Unlock Your Unlimited Potential: https://www.amazon.com/dp/1523007001  Eat That Frog!: 21 Great Ways to Stop Procrastinating and Get More Done in Less Time: https://www.amazon.com/dp/162656941X  The 21 Success Secrets of Self-Made Millionaires: How to Achieve Financial Independence Faster and Easier than You Ever Thought Possible: https://www.amazon.com/dp/0369307534  Think and Grow Rich by Napoleon Hill: https://www.amazon.com/dp/1585424331  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

When Sharon Price John was a kid, she spent a summer determined to climb a massive tree. After several falls, she reached the top, only to realize she didn’t know how to get down. As darkness fell, she jumped into the pine needles below and learned a lasting lesson: tough goals can be fun. Years later, that same mindset guided her as CEO of Build-A-Bear Workshop, a company that was $49 million in the red. Instead of retreating, she climbed again, leading one of retail’s greatest comebacks. In this episode, Sharon shares how to face fear with curiosity, lead with heart, and use storytelling to spark transformation in business and life. Sharon Price John is the President and CEO of Build-A-Bear Workshop, where she led one of retail’s most inspiring turnarounds. She is also the author of Stories & Heart and Chair of the Toy Association. In this episode, Ilana and Sharon discuss (00:00) Introduction (02:17) The Truth Behind Every “Overnight” Success (03:53) The Tree That Taught Her Courage (07:16) Breaking Into Advertising (13:49) Climbing the Ladder at Mattel (19:41) When Her Startup Collapsed (28:55) Leading a Turnaround When Everything Seems Lost (32:44) The One Rule Every Great Leader Lives By (33:40) Avoiding the Mistakes That Cost You Most (38:12) The Strategy That Saved Build-A-Bear (50:57) Leading With Courage and Clarity Through Crisis(01:04:33) Storytelling as the Heart of Great Leadership Sharon Price John has served as President and CEO of Build-A-Bear Workshop since 2013, leading the brand from a $49 million loss to record profitability. Before Build-A-Bear, she held senior roles at Hasbro, Mattel, and Stride Rite Children’s Group, earning a reputation as a turnaround expert. Sharon is the author of Stories & Heart and serves on the boards of Jack in the Box and First Book. She is also Chair of the Toy Association.  Connect with Sharon: Sharon’s LinkedIn: linkedin.com/in/sharon-price-john-26239820 Sharon’s Website: storiesandheart.com Resources Mentioned: Sharon’s Book, Stories & Heart: Unlock the Power of Personal Stories to Create a Life You Love: https://www.amazon.com/dp/1950863441 First Book: https://firstbook.org Build-A-Bear Workshop: https://www.buildabear.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

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

Ben Weiss set out to create the future of footwear. With nothing but conviction and a radical idea to merge AI with design, he reached out to Reebok co-founder Joe Foster, the man who turned a small factory dream into a global empire. What began as a cold message became a collaboration between two builders chasing the next revolution in shoes. In this episode, Ben and Joe join Ilana to unpack what it takes to see opportunity before the world does and how to keep building, no matter the odds or the decade. Joe Foster is the co-founder of Reebok, the small family startup that became one of the world’s most iconic sports brands. Ben Weiss is the founder and CEO of Syntilay, a footwear innovation company building the future of sneakers through AI design and 3D printing. Together, their partnership is transforming the footwear industry. In this episode, Ilana, Ben, and Joe discuss: (00:00) Introduction (03:50) The Birth of Reebok (09:59) Breaking into the U.S. Market Against All Odds (19:04) How Women Skyrocketed Reebok’s Success (20:19) Hollywood and the Rise of Reebok (23:04) Facing Challenges with Optimism (25:27) Syntilay: A New Concept in AI Footwear (28:30) Persistence and White Space Thinking (32:56) Innovating with AI and 3D Printing (36:17) The Future of Footwear and Technology (41:41) Advice for Aspiring Entrepreneurs Joe Foster is the co-founder of Reebok, the small startup he and his brother Jeff built into one of the world’s most iconic sports brands. Through innovation and perfect timing, he helped turn Reebok into a global household name. After stepping away, he authored the bestselling memoir Shoemaker and launched the How to Survive & Thrive series, now in its fourth edition. At 90, he continues to speak worldwide and mentor founders, sharing enduring lessons on creativity, resilience, and reinvention. Ben Weiss is the founder of Syntilay, a Florida-based startup pioneering AI-designed, 3D-printed sneakers. With advisors like Reebok founder Joe Foster and original Shark Tank investor Kevin Harrington, Ben is redefining how shoes are created through technology, speed, and personalization. His mission is to empower creators to design and own their own footwear brands. Connect with Joe and Ben: Joe’s LinkedIn: linkedin.com/in/joe-foster-a38a4b10b  Ben’s LinkedIn: linkedin.com/in/benxweiss/  Resources: Syntilay: https://syntilay.com/  Joe’s Book, Shoemaker: The Untold Story of the British Family Firm that Became a Global Brand: https://www.amazon.com/dp/1471194019  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Jim McKelvey did the impossible. He beat Amazon. The tech giant launched a product similar to Square’s, undercut their pricing, and leveraged its massive brand. Everyone thought Square was doomed. But a year later, Amazon quit and even mailed Square readers to their customers. That left Jim with a bigger question: “How did we survive when no one else ever has?” The search for that answer inspired his book The Innovation Stack, a blueprint for building a business that cannot be copied. In this episode, Jim joins Ilana to reveal the secret to creating an unbeatable business, why ignorance can be a superpower, and how to survive the impossible as an entrepreneur. Jim McKelvey is the co-founder of Square (now Block), a billionaire entrepreneur, and author of The Innovation Stack. He also founded LaunchCode, a nonprofit providing free tech education and job placement. In this episode, Ilana and Jim will discuss: (00:00) Introduction  (02:04) Growing Up as an ‘Uncool’ Kid in St. Louis (04:01) The Early Hustle That Jumpstarted His Career (07:47) Launching a Business with 15-Year-Old Jack Dorsey (13:50) The Birth of Square: From Glass Blowing to FinTech (20:09) The Art of Selling and Capturing Attention (26:48) How a Single Demo Won Over MasterCard (31:04) Amazon's Failed Attempt to Crush Square (32:17) The Innovation Stack: Building an Unbeatable Business (35:55) Why Most Entrepreneurs Give Up Too Soon (41:32) Why the Best Innovators Are Always “Unqualified” Jim McKelvey is a serial entrepreneur, inventor, and philanthropist best known as the co-founder of Square (now Block), the fintech company that redefined digital payments. He is the author of The Innovation Stack, which explores how companies can survive by creating solutions that can’t be copied. Jim also founded LaunchCode, a nonprofit that provides free tech education and job placement for aspiring coders.  Connect with Jim Jim’s LinkedIn: linkedin.com/in/mckelveyjim Resources Mentioned Jim’s Book, The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time: https://www.amazon.com/Innovation-Stack-Building-Unbeatable-Business/dp/0593086732 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training