Rob LoCascio (LivePerson, KID Company, UareAI): He Built A $6bn Business and Left To Start Over... Here's Why!

Robert LoCascio went public at 33, helped invent web chat, and spent nearly three decades building LivePerson into a $6 billion company. What followed was not the ending he expected.

In this episode of CEOs & ABCs, Kevin Rice sits down with the founder of LivePerson for a rare and deeply honest conversation about leadership under extreme pressure, navigating macro events like the dotcom crash, 9/11, and COVID, and what happens when the greatest threat comes from inside the system. Rob opens up about activist investors, an unplanned exit from the company he built over 28 years, and the emotional toll that season took on his identity and his family.

Rob shares the hard-earned leadership lessons that shaped him, from the moment a board member told him “just don’t bullshit them,” to why the best response to chaos is often no response at all. He explains why slowing down during crises creates clarity, how fear-based decisions compound risk, and why your weakest links matter most when you’re under attack. The conversation also explores fatherhood, marriage later in life, and what it looks like to rebuild from scratch.

Today, Rob is starting again in a completely different space, building a kid-first AI product designed around safety, creativity, and bringing families back into connection. This episode is a masterclass in resilience, integrity, and what it really means to begin again when the game changes.

In This Episode You’ll Learn

- What it’s like to take a company public at 33
- How to lead through layoffs with honesty and integrity
- Why slowing down is critical during macro crises
- How fear distorts decision-making at the executive level
- What activist investors really do behind the scenes
- How leadership pressure spills into family life
- Why rebuilding sometimes means starting from zero
- How fatherhood reshaped Rob’s definition of success
- Why imposter syndrome may actually be your inner child
- How to think about AI, kids, and creativity responsibly

Top Takeaways

- Truth builds long-term trust, even in the hardest moments
- The worst decisions are made when fear is driving
- Macro events should be observed before they’re reacted to
- Weak leadership links are exposed under pressure
- You cannot dump the business onto your family and stay connected
- Success brings visibility, and visibility brings risk
- Resilience is modeled, not taught
- No one can take your ability to create and rebuild
- Starting over can unlock deeper purpose

About Robert LoCascio
Robert LoCascio is the founder of LivePerson and a pioneer of internet-era customer communication, credited with inventing web chat. He took LivePerson public in 2000 and led the company for nearly 30 years, growing it to a peak market capitalization of over $6 billion. Today, Rob is the founder of KID, a kid-first AI product designed to empower creativity, ensure safety, and strengthen family connection. He is also a father of three and a lifelong builder focused on integrity, imagination, and impact.

Chapters

• (00:00:00) - Introduction
• (00:05:52) - Navigating Challenges: Lessons from the Dot Com Era
• (00:12:53) - Growth Through Adversity: The Impact of COVID-19
• (00:19:46) - Balancing Act: Family Life and High-Pressure Careers
• (00:29:53) - From Public Company to Startup: A New Chapter
• (00:30:16) - The Impact of Activist Investors
• (00:34:22) - Navigating Existential Threats in Business
• (00:38:42) - Family Dynamics During Corporate Turmoil
• (00:43:01) - Rebuilding After Exit: A Personal Journey
• (00:47:08) - Lessons Learned from Leadership Challenges
• (00:49:59) - Innovating for the Next Generation: A New Venture