Faith in the Future: Rob LoCascio @ Live Person

One of the defining characteristics of this age of business is ambiguity. And to face that ambiguity with courage, we need to heed both ambitious visions of the future and the hard-earned lessons of the past. And you couldn’t ask for a better source of prescient ideas and valuable lessons than LivePerson CEO & Founder Rob LoCascio. He’s the rare tech entrepreneur who really may have seen it all.

In his talk with Jesse, Rob discusses the ups and downs of his 25-year journey, revealing how he managed through the dot-com bubble, the Great Recession, and now, a global pandemic. He reflects on his company’s invention of cloud-based web chat for business, achieved decades before the cloud as we know it came into existence. Rob offers thoughts on the future of conversational commerce, and reveals how LivePerson is now building AI tools that can hold remarkably natural and confidence-inspiring conversations with customers. Finally, he attests to the power that blockchain technology can offer to workers, and describes how he’s leading with empathy in support of employees. Throughout, Rob’s depiction of what he calls his “beautiful journey” is refreshingly frank, earnestly offered, and packed with useful advice and encouragement for entrepreneurs and intrapreneurs alike.

(4:01) Why the entrepreneurial journey is full of setbacks and unknowns, but worth it

(8:54) Inventing the cloud, decades before the cloud

(13:24) How LivePerson builds chatbots that can hold more natural & personalized conversations with customers

(21:55) The rise and democratizing potential of blockchain tech for workers

(26:25) How conversational commerce can actually decentralize commerce—for good

(28:12) To college or not to college?

Guest Bio

Rob LoCascio has served as LivePerson’s Chief Executive Officer and Chairman of the Board of Directors since the company’s inception in November 1995. Additionally, he founded the charity Feeding NYC, hosts the podcast Over The Wall and is a frequent contributor to Inc., and other publications. Rob was named a New York City Ernst & Young Entrepreneur of the Year finalist in 2001 and 2008, and was the winner of the 2015 Smart CEO Circle of Excellence Award.

Helpful Links

Rob’s podcast: Over the Wall

Inc. article: Four things to consider before turning your business over to bots (Rob authored)

Announcing the launch of Conversational Marketplaces

Rob’s charity: Feeding NYC

Rob on LinkedIn and Twitter