Leap Academy with Ilana Golan

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

Klaus Kleinfeld’s journey from a difficult childhood in Germany to leading two Fortune 500 companies, Siemens and Alcoa, was anything but easy. He experienced  the true cost of leadership: the loneliness of making impossible decisions and the grit to push forward when every alternative seems bleak. In this episode, Klaus joins Ilana to share how resilience and freedom shaped his leadership philosophy. They dive into his shift from time management to energy management, exploring lessons from sports, breathing techniques, and mindset practices that helped him lead various multi-billion dollar businesses without burnout.  Dr. Klaus Kleinfeld is a German entrepreneur, investor, and former CEO of Siemens AG, Alcoa Inc., and ARconic. He is also the founder and CEO of the investment firm K2Elevation and was named director of Saudi Arabia's Neom initiative, later becoming an advisor to the Crown Prince. In this episode, Ilana and Klaus will discuss: (00:00) Introduction (02:01) Early Life and Family Tragedy (07:31) East vs. West Germany and Freedom (12:01) His Love for Problem-Solving (18:01) Creating a Strong Feedback Culture (23:31) Becoming the CEO of Siemens (30:01) The Loneliness of Leadership (35:31) Letting People Go with Respect (40:01) Facing Fear and Regret (45:31) Energy Over Time Management (50:01) Building a Passionate and High-Performance Team Dr. Klaus Kleinfeld is a German entrepreneur, investor, and former CEO of Siemens AG, Alcoa Inc., and ARconic. He is also the founder and CEO of the investment firm K2Elevation and was named director of Saudi Arabia's Neom initiative, later becoming an advisor to the Crown Prince. As the author of Leading to Thrive, Klaus offers a framework for blending personal well-being with strategic leadership.  Connect with Klaus: Klaus’s LinkedIn: linkedin.com/in/klauskleinfeld Resources Mentioned: Klaus’s Book, Leading to Thrive: Mastering Strategies for Sustainable Success in Business and Life: https://www.amazon.com/Leading-Thrive-Mastering-Strategies-Sustainable/dp/1544546718 The Power of Regret: How Looking Backward Moves Us Forward by Daniel Pink: https://www.amazon.com/Power-Regret-Looking-Backward-Forward/dp/0735210659 Open: An Autobiography by Andre Agassi: https://www.amazon.com/Open-Autobiography-Andre-Agassi/dp/0307388409 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

Nathan Blecharczyk, co-founder of Airbnb, built his first software business as a teenager, earning nearly a million dollars before shutting it down to attend Harvard. Years later, Nathan and his roommates turned an air mattress idea into Airbnb, facing investor rejection, financial hardship, and moments when quitting seemed inevitable. From creating satirical cereal boxes to joining Y Combinator after a near-failed interview, Nathan’s story is one of perseverance and resilience. He shares how Airbnb overcame early struggles, scaled globally, and survived COVID-19 to go public successfully. Nathan Blecharczyk is the co-founder and Chief Strategy Officer of Airbnb, where he helped grow the platform from a spare air mattress idea to a $75 billion global travel company. According to Forbes, he is one of the richest people in the world, with a net worth of $9 billion. In this episode, Ilana and Nathan will discuss: (00:00) Introduction (01:36) Building a Software Business as a Teen (05:28) Harvard, First Job, and the Decision to Move West (11:58) The Birth of AirBed & Breakfast (15:07) Landing Their  First Guests and Gaining Early Validation (18:03) Investor Rejection and the Obama O’s Cereal Stunt (30:45) Applying to Y Combinator and Getting In (36:29) Finding Evangelists and Meeting Hosts in New York (42:34) From $200 a Week to $4,200: Airbnb’s First Growth Curve (44:59) Global Expansion, Competitors, and Building Teams Abroad (52:22) The 2020 Crisis: COVID, Collapse, and Reinvention (59:21) The Future of Travel  Nathan Blecharczyk is the co-founder and Chief Strategy Officer of Airbnb, where he helped grow the platform from a spare air mattress idea to a $75 billion global travel company. A Harvard graduate and self-taught programmer, Nathan has been instrumental in Airbnb’s international expansion and strategy, navigating challenges from investor rejection to the COVID-19 crisis. According to Forbes, he is one of the richest people in the world, with a net worth of $9 billion. Connect with Nathan: Nathan’s LinkedIn: ⁠https://www.linkedin.com/in/blecharczyk⁠ Airbnb’s Website: ⁠https://www.airbnb.com⁠ Resources Mentioned: Y Combinator: ⁠https://www.ycombinator.com⁠Only the Paranoid Survive by Andy Grove: ⁠https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821⁠ 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

After 12 years of working in corporate advertising, Case Kenny launched a podcast, New Mindset, Who Dis? as a personal experiment. In its first month, the show drew 57,000 downloads, yet Case kept it hidden, afraid it didn’t fit his professional image. Over time, he embraced his vulnerability, created bestselling guided journals, and built a brand helping millions live more optimistic and mindful lives. In this episode, Case joins Ilana to share how a side project turned into a multi-million-dollar portfolio career, why regret is his decision-making compass, and how choosing the right words can change the way you live. Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. In this episode, Ilana and Case will discuss: (00:00) Introduction (01:42) From Language Studies to Corporate Advertising (05:07) Starting the Podcast Without Clarity (07:43) Overcoming the Fear of Vulnerability (09:04) Stepping Fully into a New Identity (14:14) When Passion Becomes a Business (16:53) COVID, Journals, and a Turning Point in Sales (18:10) Why Journaling Works and How to Start (25:01) Building a Connected Portfolio Career (27:40) Business Challenges and Six-Figure Losses (33:09) Battling Expectations, Regret, and Trust as a Default (42:10) Defining Mindfulness and Advice to Case’s Younger Self Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?, a podcast with tens of millions of downloads. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. His work has been featured on The Today Show, Good Morning America, Forbes, and NBC. Connect with Case: Case’s Website: casekenny.com Case’s LinkedIn: linkedin.com/in/casekenny/ Case’s Instagram: instagram.com/case.kenny Case’s YouTube: youtube.com/c/CaseKenny Resources Mentioned: Case’s Podcast, New Mindset, Who Dis?:  pod.link/1383599078 The Opposite of Settling by Case Kenny: https://www.amazon.com/Opposite-Settling-Everything-Without-Losing/dp/1401995918 The Soul’s Code by James Hillman: https://www.amazon.com/Souls-Code-James-Hillman/dp/0517271036 That’s Bold of You by Case Kenny: https://www.amazon.com/Thats-Bold-You-Thrive-Vibrant/dp/B0BRDFLJNZ 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