Leap Academy with Ilana Golan

Episode 128 | How Thai Randolph Built a $100M Agency With Kevin Hart

Guest: Thai Randolph, Entrepreneur & Former CEO of Hartbeat
Date: October 8, 2025

Overview

In this candid and motivating episode, Ilana Golan sits down with Thai Randolph, the powerhouse behind Hartbeat’s meteoric rise and one of the few Black women to lead a $100M+ private equity round in the U.S. The conversation charts Thai’s journey from her rural South Carolina roots to influential roles at Sony, Facebook, and ultimately, building Kevin Hart’s multi-platform media empire. Thai opens up about resilience through career pivots, challenges of leadership, personal struggles with fertility, and the importance of redefining identity beyond work. Listeners gain not just behind-the-scenes insights into major media deals, but also invaluable wisdom on leadership, growth, and life’s messy realities.

Key Discussion Points & Insights

Thai’s Upbringing, Family, and Foundational Lessons

• Rural Roots & Resilience
  • Thai grew up on a family farm in Holly Hill, South Carolina—a tiny place where getting a Hardee’s fast food restaurant merited a town parade.
  • Early transitions, like moving to the suburbs after her parents’ divorce, built resilience muscles at a young age.
  • “Those muscles of resilience that we build even earlier in our youth, you're surprised how they pay off.” (04:25, B)
• Seeing Is Believing
  • Thai was inspired by seeing successful role models on TV, notably Claire Huxtable from The Cosby Show, fueling her early ambitions for law and later journalism.
  • An unpaid internship at a local radio station in high school “shifted things,” igniting her love for storytelling.

The “River” Career Path: Serendipity, Storytelling, and Agency Work

• Educational Adventure & Early Moves
  • Attended Clemson on scholarships, transferred to American University in D.C., and majored in visual media.
  • Early work in a PR agency led to exposure to “face to face communications,” and her first marketing job involved (unexpectedly) launching a missile system for Raytheon.
  • This experience spurred self-reflection and career realignment to work on projects aligned with her values.
  • “I was literally marketing weapons of mass destruction... I needed to do that for things that I cared about and believed in.” (08:34, B)
• Agency to Entertainment Ladder
  • Progressed rapidly from agencies like Definition 6 and Moxie, pioneering social media departments when Facebook and Twitter were new.
  • Gained major clients (Verizon, Coca Cola, Revlon) and was eventually recruited to Sony for a direct-to-consumer artist platform and a major management buyout.
  • Transitioned to Facebook, then Lionsgate, where she joined the team launching Laugh Out Loud with Kevin Hart.

Career, Fertility, and Learning Empathy

• Personal Struggles & Empathy as a Leader
  • While at Facebook, Thai faced fertility challenges and went through IVF, only to later become pregnant naturally after moving to LA for Lionsgate.
  • She credits these deeply personal experiences for making her a more empathetic and effective leader.
  • “Every day someone's showing up to an office with cancer or infertility or grief or anxiety and mental health issues. We just have to package it and put on.” (21:50, B)
• Advice to Driven Women
  • Emphasizes “maximizing optionality” for women regarding fertility—take advantage of company benefits early, regardless of immediate plans.
  • Thai ensured that parental and family leave policies at Hartbeat were gender-neutral and inclusive.

Building with Kevin Hart: From Lionsgate to Independent Empire

• Joint Venture to Independence
  • Initially joined Lionsgate, met Kevin Hart via their joint venture, and was instrumental in carving out Laugh Out Loud into an independent company.
  • Led go-to-market strategy, full-scale business re-platforming, and ultimately, the merger with Hartbeat Productions.
  • “The only thing harder than starting a new business is carving a business out of one.” (27:57, B)
• Major Capital Raise
  • Orchestrated the complex $100M+ funding round, merging two companies and cultures, and ensuring return-on-investment focus.
  • Notable: Process happened mid-pandemic—she closed deals while sick with COVID-19.
  • “There has to be an institutionalized path to return... and there has to be real rigor and belief in the team that they're investing in.” (32:09, B)
  • The company pivoted from a streaming app to a multi-platform company with live events, brand work, and global reach.
  • “All of the growth, all the accolades, the volume, the velocity, it was just, it was an incredible run.” (33:42, B)

Leadership: Ownership, Burnout, and Lessons Learned

• From SVP to CEO
  • Thai always approached her work “like an owner”—mastering every component before being officially promoted.
  • “My approach was never to go to someone and say I think I could do this... I was already doing the job that I’m asking you for.” (34:54, B)
• On Burnout & Boundaries
  • Being CEO means heavy responsibility, but leaders must avoid internalizing every challenge.
  • “Energy is capital. You have to be careful how you invest it. And... you can deplete yourself.” (35:46, B)
  • Thai recounts advice from her own team: “She said, ‘no, we’re not a family. We’re a team.’... Teams have healthy boundaries and agency. That was the right construct.”

Redefining Identity Post-CEO and the “Ownership Economy”

• Life and Identity Beyond Work
  • Leaving Hartbeat after seven years was a major emotional transition, especially with personal identity strongly tied to the company.
  • “If you’re feeling like you’re lost or you don’t have an identity without it... oh my god, am I so reliant on this to define who I am? And, like, whose life is it anyway?” (46:34, B)
  • Ilana and Thai discuss the importance of executive branding—knowing one’s values and what one contributes no matter the organization.
• The New Portfolio Career World
  • Thai foresees work shifting to “the ownership economy,” where incentives, equity, and agency matter more than pension or single-role loyalty.
  • “The old playbook for compensation incentives just don’t cut it anymore.” (49:46, B)
• Current Projects & Board Work
  • Thai sits on the board of Rock the Bells (LL Cool J’s company), invests in inclusive beauty brands, and is developing a new venture that leverages her whole career journey.

Notable Quotes & Memorable Moments

• “I always talk about my career as more of a river than a ladder.” (05:22, B)
• “You could only be what you can see.” (04:02, B)
• “Big careers are expensive, big risks are expensive. It takes a lot emotionally... so you just want to make sure that your time, your energy, your intellect is well spent.” (52:15, B)
• “Letting yourself off the hook is the best thing you can do.” (41:21, B)
• “You can be happy even when things are hard.” (42:22, B)
• “All of those steps or those opportunities looked like challenges in the beginning... and they ended up being accelerators.” (25:52, B)
• “As women, we’re just taught to go, go, go, go, go. Especially now... but you can’t wear it all.” (07:10 & 35:46, B)
• “I believe there's a one plus one equals billion dollar proposition.” (31:29, B)

Timestamps for Key Segments

• Thai's early life and resilience: 02:41–05:09
• Discovery of storytelling and career pivots: 05:22–10:11
• Agency work through to Sony/Lionsgate: 10:28–13:55
• Fertility journey and leadership empathy: 16:33–22:03
• Joining & growing Laugh Out Loud/Hartbeat: 23:36–25:52
• Challenges carving out Hartbeat & entrepreneurship lessons: 27:57–29:31
• $100M capital raise, merging companies: 30:00–33:55
• CEO transition, burnout, and leadership mindset: 34:24–39:39
• Redefining self & modern career structures: 43:33–50:13
• Current advisory/investment work & upcoming project: 50:44–51:55
• The advice she wishes she’d known sooner: 52:13

Final Wisdom

Thai Randolph’s story is a masterclass in resilience, adaptation, and intentionality. Her candid reflections offer a blueprint for leaping into new territory, leading inclusively, and anchoring in one’s own values—no matter how high the stakes. Whether you’re dreaming of entrepreneurial leaps, building a career in dynamic industries, or simply seeking more agency and meaning, her journey is a powerful inspiration.

Listen to the full episode for more insight-rich stories and life lessons.