Leap Academy with Ilana Golan

• Wikipedia Co-Founder: How Jimmy Wales Changed the Internet Forever | E133

  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

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• How Reebok’s Co-Founder Joe Foster and Ben Weiss Are Revolutionizing the Footwear Industry | E132

  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

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• Square Co-Founder, Jim McKelvey: How to Build a Business No Competitor Can Copy | E131

  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

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• Betting $250M on Women’s Sports: How Rejection Became Kara Nortman’s Superpower | E130

  At a 2015 World Cup match in Vancouver, Kara searched nine stores for her daughters’ jerseys and found none. That spark of “joyful irritation” became a movement to build teams, build community, and build an industry. In this episode, Kara joins Ilana to share how that moment ignited Angel City FC, how she, along with her partners, managed to create one of the most valuable women’s soccer teams in the world, and why she embraces rejection as a growth strategy. She breaks down the tension between patience and urgency, the power of finding joy in pursuing one’s passions, and how to choose partners who amplify your mission. Kara Nortman is the co-founder of Angel City FC and managing partner of Monarch Collective, a $250M investment platform driving the growth of women’s sports. A former investor at Upfront Ventures and operator at IAC, Kara brings decades of experience turning bold ideas into lasting movements. In this episode, Ilana and Kara will discuss: (00:00) Introduction (02:03) Realizing the Market Gap in Women’s Sports (04:16) Turning Inspiration into Action (06:44) Finding Joy Through Volunteering and Community (11:54) The Birth of Angel City FC (17:23) Turning Rejection into Fuel (30:48) Breaking into the World of Venture Capital (31:42) Game-Changing Mentorship and Early Career Lessons (33:47) Discovering a Passion for Tech at Battery Ventures (44:19) Building Angel City and Redefining the Playbook (50:04) Launching Monarch and Scaling the Movement Kara Nortman is an investor, founder, and sports operator focused on advancing the women’s sports economy. As a co-founder of the professional women's soccer team, Angel City FC, she pioneered a community-first 10% sponsorship model that drove significant commercial success. Kara co-leads Monarch Collective, investing in women’s sports teams and related businesses across the U.S. and Europe. Previously, she was a managing partner at Upfront Ventures and an executive at IAC, where she helped incubate Tinder through Hatch Labs. Connect with Kara: Kara’s LinkedIn: linkedin.com/in/karanortman Resources Mentioned: Monarch Collective: https://monarchcoll.com Angel City FC: https://angelcity.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

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• How a Panic Attack Revealed the Secret to a Meaningful Life | Robert Glazer | E129

  Robert Glazer collapsed in his kitchen in front of his son, convinced he was having a heart attack. In reality, it was a massive panic attack triggered by grinding too hard while starting a business, building a house, raising kids, and weathering the 2008 recession. That wake-up call forced him to reevaluate everything: his health, his leadership, and the values that guided his life. In this episode, Robert returns to the show to share how childhood struggles shaped his values, why passion is developed, not discovered, and how to know if you’re climbing the wrong mountain in life. He also reveals the frameworks from his new book to help you align your career, relationships, and purpose with your deepest values. Robert Glazer is a serial entrepreneur, bestselling author, and global keynote speaker. He founded Acceleration Partners, a 300-person marketing agency, and is the author of eight books, including Elevate and his newest release, The Compass Within. In this episode, Ilana and Robert discuss: (00:00) Introduction (02:09) Growing Up as the “Underachiever” Kid (05:20) Discovering a Love for Learning in College (09:00) How Helping One Company Sparked an Agency (10:30) The Health Scare That Sparked a Wake-Up Call (14:18) Leading with Transparency During COVID (16:56) Choosing to Step Aside as CEO (19:29) Writing The Compass Within as a Story (22:00) Understanding Core Values (26:09) The Three Climbs of Success for High Achievers (29:12) Six Questions to Identify Your Core Values Robert Glazer is an entrepreneur, bestselling author, and thought leader on business and personal growth. He founded Acceleration Partners, scaling it into a 300-person agency recognized for its values-driven culture. Robert is the author of eight books, including Elevate and The Compass Within, and the Friday Forward newsletter. Known for his insights on leadership, capacity building, and core values, he speaks on stages around the globe and helps individuals and organizations align success with authenticity. Connect with Robert Robert’s Website: robertglazer.com  Robert’s LinkedIn: linkedin.com/in/glazer   The Compass Within Website: compass-within.com Resources Mentioned LEAP Episode 32 with Robert Glazer: https://podcasts.apple.com/us/podcast/the-art-of-reinvention-how-to-elevate-your-career/id1701718200?i=1000660153819 The Six Core Values Questions: robertglazer.com/six Robert’s Book, The Compass Within: A Little Story About the Values That Guide Us: https://geni.us/values Free Course: robertglazer.com/compass-leap Robert’s Book, Elevate: Push Beyond Your Limits and Unlock Success in Yourself and Others: https://www.amazon.com/Elevate-Beyond-Limits-Success-Yourself/dp/1492691488  The Freak Factor: Discovering Uniqueness by Flaunting Weakness by David Rendall: https://www.amazon.com/Freak-Factor-Discovering-Uniqueness-Flaunting/dp/1599326698  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

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