Leap Academy with Ilana Golan

• 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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• How Thai Randolph Built a $100M Media Company | E128

  Most people would assume that raising capital for a celebrity-backed business would be a cakewalk, but Thai Randolph knew that was far from the truth. Securing $100 million in investment for Kevin Hart's Hartbeat Productions required more than just a famous name; it took proving real value, building trust, and navigating rejection. Her success led to one of the largest private-equity rounds ever led by a Black woman in the U.S. In this episode, Thai joins Ilana to share the lessons she’s learned throughout her career, from her time at Sony, Facebook, and Lionsgate. She also opens up about her personal struggles with fertility while building a successful career and the pivotal moments that shaped her leadership style. Thai Randolph is an award-winning entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. In this episode, Ilana and Thai discuss: (00:00) Introduction (01:51) How Thai’s Small-Town Roots Shaped Her Path (04:58) Pivoting from Marketing Missiles to Storytelling (09:36) Breaking into Big Tech: From Sony to Facebook (14:14) Balancing Fertility Struggles and Career Moves (22:11) Joining Lionsgate and Meeting Kevin Hart (26:34) Challenges of Carving Out a New Business (28:20) Raising $100M for Hartbeat Against All Odds (32:40) Transitioning to CEO and Leadership Lessons (37:49) Balancing Work, Life, and Avoiding Burnout (41:57) Redefining Your Identity Beyond the Job Title (49:28) Thai’s Next Big Ventures and Future Plans Thai Randolph is an entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. As President and COO of Laugh Out Loud, she oversees the strategy and operations for Kevin Hart’s comedy network. Thai has driven digital transformation at companies like Facebook and Sony, and provided media strategy for top brands like Verizon, Dell, and more. Connect with Thai:  Thai’s LinkedIn: linkedin.com/in/thairandolph Thai’s Instagram: instagram.com/thairandolph Resources Mentioned: Thai’s Podcast, The Suga: podcasts.apple.com/us/podcast/the-suga/id1502324399  LOL Network: youtube.com/@lolnetwork  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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• Lisa Bilyeu: From Housewife to Billion-Dollar Boss, My No-BS Guide to Radical Confidence | LEAP Replay

  For eight years, Lisa Bilyeu lived the life others expected: a traditional Greek wife focused on supporting her husband and running the home. But deep down, she knew she was meant for more. With no business background, zero confidence, and no clear roadmap, she decided to rewrite her story. She co-founded Quest Nutrition with her husband and built a billion-dollar business. In this LEAP Replay, Lisa opens up to Ilana about breaking free from cultural expectations, showing up authentically in the face of criticism, and how you can build radical confidence without needing external validation. Lisa Bilyeu is an entrepreneur, bestselling author, and co-founder of Quest Nutrition, a multi-billion-dollar company. Her mission is to use content creation to empower women to break free from limiting beliefs and build extraordinary lives. In this episode, Ilana and Lisa will discuss: (00:00) Introduction  (02:22) Her Upbringing and the Weight of Expectations (06:44) Velvet Handcuffs: The Trap of People Pleasing (10:55) Transitioning from Housewife to Co-Founder (19:13) Handling Your Emotions in Business  (24:25) How Lisa Tackles Online Hate and Criticism (33:12) The Three Keys to Mission-Driven Content Creation (37:25) Lisa’s No-BS Guide to Success  (44:40) Why She Chose Her Mission Over Motherhood  (1:03:06) Building Radical Confidence Through Self-Reliance Lisa Bilyeu is an entrepreneur, author, and co-founder of Quest Nutrition, a multi-billion-dollar company that transformed the health and wellness industry. She is also the founder and host of Women of Impact, co-founder of Impact Theory, and bestselling author of Radical Confidence. Lisa’s mission is to use content creation to empower women to break free from limiting beliefs and embrace their full potential.  Connect with Lisa: Lisa’s Website: https://lisabilyeu.com/ Lisa’s YouTube: www.youtube.com/@LisaBilyeu  Lisa’s Instagram: https://www.instagram.com/lisabilyeu Resources Mentioned: Lisa’s Book, Radical Confidence: 11 Lessons on How to Get the Relationship, Career, and Life You Want: https://www.amazon.com/dp/B09JPHK9C3 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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