Leap Academy with Ilana Golan

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

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

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

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 

In this conversation, Lisa Bilyeu, an entrepreneur and co-founder of Quest Nutrition, shares her journey from a traditional Greek housewife to a billion-dollar business leader. She discusses breaking free from cultural expectations and the 'velvet handcuffs' of people-pleasing that held her back. Lisa emphasizes the importance of emotional sobriety in decision-making and reveals her framework for mission-driven work. She also offers a candid look at handling online criticism with empathy and staying true to one's passions over societal norms.

Sir Richard Branson, the adventurous founder of the Virgin Group, shares his journey from quitting school at 15 to launching trailblazing businesses like Virgin Records and Virgin Atlantic. He reveals how dyslexia became a superpower, fueling his entrepreneurial spirit. Richard discusses resilience and the unique 'Reserve Tank' mindset for overcoming challenges. He also shares captivating stories about negotiating for peace and using his influence for humanitarian efforts, showcasing how risks can lead to remarkable rewards.

Ilana Golan shares her incredible journey from losing everything to becoming a leader in the startup world. She reveals the five essential shifts needed for career reinvention and explains the importance of adaptability in today's ever-changing landscape. Discover how to transform your personal brand, align your story with your goals, and tap into hidden opportunities. Ilana also advocates for building a portfolio career to achieve freedom and wealth. Her insights are not just motivational but also actionable!

Despite outward success, Brad Feld struggled with depression, exhaustion, and feelings of emptiness. For years, he hid these challenges while relentlessly pushing forward as an entrepreneur. It wasn’t until his 40s, after seeking therapy and confronting his mental health, that Brad realized success wasn’t just about building companies, but about managing the emotional toll of entrepreneurship. Today, as the co-founder of Techstars and Foundry Group, he leads with a harmonious approach to work and life. In this episode, Brad joins Ilana to share the lessons he learned from early failures, why every successful founder faces ‘near-death moments’, and the mental health practices that helped him find joy again. Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. In this episode, Ilana and Brad discuss: (00:00) Introduction (01:07) Growing Up in Dallas and Discovering Computers (07:29) MIT Years and Early Startup Failures (14:17) Why Every Startup Faces a Near-Death Experience (16:54) Battling Fear, Shame, and Depression in His Twenties (26:52) Breaking Down at 47 Despite “Having It All” (29:05) Brad’s Practical Steps for Rediscovering Joy (41:54) The Random Day Experiment and Birth of Techstars (52:47) Writing Venture Deals, Startup Communities, and Give First (59:26) Coming Out of “Hibernation” to Write His Last Non-Fiction (1:13:39) Work-Life Balance vs. Work-Life Harmony Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. Brad is the author of nine books, including Venture Deals, Startup Communities, and Give First. Through his books, investments, and philosophy of “give first,” Brad has become a mentor to thousands of entrepreneurs navigating the brutal highs and lows of building a business. Connect with Brad:  Brad’s Website: feld.com Brad’s LinkedIn: linkedin.com/in/bfeld  Resources Mentioned Brad’s Book, Give First: The Power of Mentorship: https://www.amazon.com/dp/1646871324  Brad’s Book, Startup Communities: Building an Entrepreneurial Ecosystem in Your City: https://www.amazon.com/dp/1118441540  Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson: https://www.amazon.com/dp/1118443616  Reboot: Leadership and the Art of Growing Up by Jerry Colonna: https://www.amazon.com/dp/0062749536 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

Brendan Kane didn’t break into Hollywood through connections. He started out making coffee on film sets. Spotting the untapped power of MySpace and YouTube, he launched one of the first influencer campaigns, catching the attention of studio executives and A-list actors like Jason Statham. That bold move launched his journey from Hollywood to advising global icons such as Taylor Swift and Rihanna on social media strategy. In this episode, Brendan joins Ilana to reveal how he built one million followers in just 30 days, the formula for going viral, and the psychology behind grabbing and holding attention. Brendan Kane is a digital marketing expert who has helped top celebrities, Fortune 500 companies, and entrepreneurs dominate social media and generate millions in revenue. He specializes in data-driven strategies that drive massive social media engagement. In this episode, Ilana and Brendan will discuss: (00:00) Introduction  (02:07) His Childhood Love for Movies and Storytelling (03:17) Breaking into Hollywood Without Connections (08:16) The Bold Move That Led to Working With A-List Actors (10:37) Diving into Tech and Working with Taylor Swift, Rihanna, etc (17:51) Lessons from Managing $100M in YouTube Ad Spend (22:06) Uncovering the Secrets to Social Media Success (27:40) How Brendan Hit a Million Followers in 30 Days (34:51) Strategies for Marketing Bestselling Books (39:10) How to Adapt to Ever-Changing Platforms (44:01) Low-Cost Strategies to Stand Out on Social Media (45:35) Navigating the Challenges of Entrepreneurship Brendan Kane is a digital marketing expert who has helped top celebrities, Fortune 500 companies, and entrepreneurs dominate social media and generate millions in revenue. Known for building a following of over 1 million in just 30 days, Brendan specializes in data-driven strategies that drive massive social media engagement. He is the bestselling author of One Million Followers, Hook Point, and The Guide to Going Viral, where he reveals proven methods for scaling influence in today’s noisy digital world. Connect with Brendan: Brendan’s Website: brendanjkane.com  Brendan’s Instagram: instagram.com/brendankane  Resources Mentioned: Get Brendan’s Book, The Guide to Going Viral, for FREE: hookpoint.com/leap  Download Brendan’s Book, Hook Point for Free: hookpoint.com  Brendan’s Book, One Million Followers: How I Built a Massive Social Following in 30 Days: https://www.amazon.com/One-Million-Followers-Updated-Following/dp/195066547X  The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357  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

George Kurian’s journey from a modest upbringing in Kerala, India, to becoming CEO of NetApp is an extraordinary story. George worked cafeteria shifts and construction jobs to pay his way through Princeton before climbing the ranks at Oracle, McKinsey, and Cisco. In this episode, George opens up about the weight of being a “rookie CEO” responsible for 12,000 people, the discipline of saying no to 97% of ideas, and the humility it takes to lead through uncertainty. He and Ilana explore resilience, focus, and the future of AI, while revealing how diverse experiences and family values shaped his leadership philosophy. George Kurian is CEO of NetApp, a Fortune 500 data infrastructure and cloud services company. Under his leadership, NetApp has strengthened its cloud-first and data services strategy, growing into a $20 billion company. In this episode, Ilana and George will discuss: (00:00) Introduction (02:20) Family Role Models and Upbringing (06:00) Landing a Princeton Scholarship and Learning to Survive (09:20) Lessons from Oracle and McKinsey (13:50) Why George Left Cisco to Join NetApp (16:45) How Cafeteria Work Inspired NetApp’s Engineering Process (19:40) The ‘30-30-30’ Rule for Driving Organizational Change (22:40) George’s Journey to Becoming CEO Overnight (26:30) First-Time CEO Challenges and Leadership Struggles (30:40) Why a CEO Should Say “No” to 97% of Ideas (33:10) Betting on Cloud Partnerships Instead of Competing (37:15) The Power of Choosing Your Path and Tackling Hard Problems George Kurian is CEO of NetApp, a Fortune 500 data infrastructure and cloud services company. Before joining NetApp in 2011, he had built a diverse tech career that included leadership roles at Oracle, McKinsey, Cisco, and Akamai. Under his leadership, NetApp has strengthened its cloud-first and data services strategy, growing into a $20 billion company. Connect with George: George’s LinkedIn: linkedin.com/in/georgekuriannetapp 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