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