Leap Academy with Ilana Golan

When Kevin Kelly dropped out of college in the 1970s, it was almost unheard of. Instead of following a traditional path, he chose a life driven by curiosity, freedom, and hands-on learning. That decision led him to hitchhike across Asia, document disappearing cultures, and eventually immerse himself in the early internet. Years later, he co-founded Wired, a magazine that soon became the voice of emerging technology and culture. In this episode, Kevin joins Ilana to share how Wired went from fighting for shelf space to redefining what a tech publication could be. He also explains his unique relationship with time, why he tracks the days he has left, and how creators today can thrive with just 1,000 true fans. Kevin Kelly is a writer, photographer, and Senior Maverick at Wired, an award-winning magazine he co-founded in 1993. He is also a former editor and publisher of the Whole Earth Review and the author of multiple bestselling books about the future of technology. In this episode, Ilana and Kevin will discuss: (00:00) Introduction  (02:14) Choosing an Unconventional Path to Success (06:34) The Start of His Adventures in Asia (10:54) Getting into Writing and Publishing (14:17) Creating One of the First Hacker Conferences (20:18) The Grit Behind Wired Magazine’s Success (30:37) The Dot-Com Bust and Why Wired was Split (34:17) The Origin and Power of “1,000 True Fans” (41:18) How a Near-Death Experience Transformed Kevin (47:10) About His Latest Book,  Colors of Asia Kevin Kelly is a writer, photographer, and co-founder of the award-winning Wired magazine, and a former editor and publisher of the Whole Earth Review. He is the co-chair of The Long Now Foundation, which champions long-term thinking, and the creator of the Cool Tools website, which has reviewed tools daily for over 20 years. Kevin is also the author of multiple bestselling books on the future of technology, and his latest book, Colors of Asia, captures the culture of all 35 Asian countries through vivid photography. Connect with Kevin: Kevin’s Website: https://kk.org  Kevin’s Twitter: https://x.com/kevin2kelly  Resources Mentioned: Kevin’s Book, Colors of Asia: A Visual Journey: https://www.amazon.com/Colors-Asia-Journey-Kevin-Kelly/dp/B0FGJ18PG5  Leaves of Grass: The Original 1855 Edition by Walt Whitman: https://www.amazon.com/dp/1449505716  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Jordan Ritter didn’t grow up surrounded by tech; he grew up on a farm, tinkering with computers in total isolation. But that early curiosity led him to co-found Napster, the file-sharing service that transformed music distribution. As millions of users flooded the platform, Jordan was instrumental in keeping it alive through sleepless nights and nonstop chaos. The success was massive, the failure was brutal, but the lessons shaped everything he did next. In this episode, Jordan reveals to Ilana the real story behind Napster, the personal sacrifices of innovation, and the mindset required to build something that leaves a legacy. Jordan Ritter is a serial entrepreneur, software architect, and angel investor, recognized for his work at Napster, the file-sharing service that reshaped music distribution and digital technology. Since then, he has launched and advised multiple startups in the tech industry. In this episode, Ilana and Jordan will discuss: (00:00) Introduction  (02:08) Growing Up on a Farm and Discovering Tech (06:40) His Journey into Hacking and Computer Security (12:37) Joining Napster and Disrupting the Music Industry (17:55) Experiencing Napster’s Highs and Crushing Lows (32:20) Why Jordan Decided to Leave Napster (40:16) Reinventing and Building Companies with Value (46:03) The Importance of Culture in Startups (52:19) Navigating Interviews and Culture Alignment (55:18) The Challenges of Starting a Business (1:03:30) Lessons Learned and Giving Back Jordan Ritter is a serial entrepreneur, software architect, angel investor, and co-founder of Napster, where he helped scale the platform to 60 million users. A four-time founder, he has built 20+ large-scale commercial and open-source products across 12 languages, developing systems used by millions. At Cloudmark, Servio, and Augment AI, Jordan built intuitive, scalable, and reliable platforms, and he now advises CoPilotKit on product strategy. Connect with Jordan: Jordan’s  LinkedIn: linkedin.com/in/jordanritter  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Ilana Golan has reinvented herself more times than most people switch job titles. From becoming one of the first women to train F-16 pilots in the Israeli Air Force, to engineering, to product, to Silicon Valley executive, to investor, to founder, she’s rebuilt her identity again and again in industries that weren’t built for people like her. In this episode of the Remarkable People podcast, Guy Kawasaki pulls back the curtain on what it really took for Ilana to leap across careers, break barriers, and build a system that helps thousands do the same. She breaks down the concept of reinvention and what it really takes to leap again and again. Ilana Golan is a former F-16 flight instructor turned Silicon Valley tech executive and investor. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. In this episode, Guy and Ilana will discuss: (00:00) Introduction  (02:20) Breaking Barriers in the Israeli Air Force (06:07) What Reinvention Really Means Today (10:40) The Core Steps to Reinventing Your Career (12:59) Reinventing When Systems are Against You (15:16) Advice for Women on Breaking Glass Ceilings (19:58) The Core Signals That You Need Reinvention (21:52) Case Studies: Reinventing Public Figures (29:37) The Role of Timing in Reinvention (33:41) The Power of Building a Personal Brand Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana:  Ilana’s Website: leapacademy.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Resources Mentioned: Guy’s Podcast, Remarkable People: https://podcasts.apple.com/us/podcast/guy-kawasakis-remarkable-people/id1483081827  LEAP E97 with Guy Kawasaki: https://podcasts.apple.com/us/podcast/guy-kawasaki-the-tech-evangelist-who-built-apple/id1701718200?i=1000703853865  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

When Vick Tipnes launched Blackstone Medical Services, it was the worst possible moment: newly divorced, broke, and with two young kids. For years, he operated in survival mode, managing a business that lost money month after month. Instead of giving up, Vick's resilience became the driving force that turned a tiny, run-down $500 office into one of the fastest-growing sleep testing companies in the U.S. In this episode, Vick opens up to Ilana about the sacrifices, powerful mindset shifts, and relentless drive that transformed his company from the brink of collapse to industry leadership. Vick Tipnes is the founder and CEO of Blackstone Medical Services, a leading provider of home sleep testing. Under his leadership, the company has earned recognition five times on the Inc. 5000 list. In this episode, Ilana and Vick will discuss: (00:00) Introduction  (02:03) Growing Up with an Entrepreneurial Father (04:35) Leaving College To Chase Entrepreneurship (06:32) Losing Both Parents and Transitioning to Healthcare (10:45) Exiting the Radiology Business with Almost Nothing (15:34) Being Divorced, Broke, and Starting All Over (19:30) Building Blackstone Medical Services from Scratch (23:27) Achieving Success After Years of Losing Money (31:27) How Vick Manages His Career Without Burning Out (33:07) Investing in Identity and Personal Growth (36:06) Addressing Sleep Issues and Health Solutions (38:18) The Power of Tenacity and Refusing To Quit Vick Tipnes is a self-made entrepreneur, author, and mentor, best known as the founder and CEO of Blackstone Medical Services, a leading provider of home sleep testing. Under his leadership, the company has earned recognition five times on the Inc. 5000 list. Vick is also the founder of Tipnes Capital and Tipnes Health and the author of Did You Sell Your Soul?, where he shares insights on overcoming obstacles, staying focused, and achieving life goals. Connect with Vick: Vick’s Website: vicktipnes.com  Vick’s LinkedIn: linkedin.com/in/vicktipnes  Vick’s Instagram: instagram.com/vicktipnes  Resources Mentioned: Vick’s Book, Did You Sell Your Soul?: It's Never Too Late to Change Your Story: https://www.amazon.com/dp/1662903766  Leap Academy:LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

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