Faith in the Future: Rob LoCascio @ Live Person
11/17/21 • 32 min
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
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
Previous Episode
Inclusive Inventor: Jenny Fleiss @ Volition Capital
Jenny Fleiss is co-founder of category creator Rent The Runway, but in some ways, that’s an understatement of the time and energy she put in to revolutionize the designer fashion industry—and forever change old ideas of Who Gets to Wear What.
In her talk with Jesse, Jenny recounts the detailed logistics work and core insights it took to drive growth at Rent The Runway, with lessons learned for aspiring founders. She describes how she now brings her entrepreneurial experience to bear as an investor, emphasizing inclusivity and the growing importance of shared wins. Jenny outlines a format that digital commerce businesses can follow to create personalized experiences at scale. And she offers advice for parents on how to inspire entrepreneurship from an early age. All told, Jenny’s story highlights the transformational power of building in oneself – and others – the confidence to excel.
(3:13) How Jenny’s experience as an entrepreneur led her to join Volition Capital this year
(8:32) Assessing the state of digital commerce—global challenges & innovations
(11:47) Jenny’s POV on the three pillars of personalization-at-scale
(16:56) Launching Rent The Runway with an unprecedented dive into logistics and a crucial market insight
(23:29) How Jenny linked up with RTR co-founder Jenn Hyman, along with her tips for finding co-founders
(29:23) Changing the VC funding landscape and increasing opportunities for women-run businesses
(31:23) Lessons for parents on teaching and encouraging entrepreneurship
Guest Bio
Jenny Fleiss joined Volition Capital in 2021 as the company’s first Venture Partner, where she focuses on next-generation consumer brands. She is an entrepreneur and intrapreneur, founding two scaled digitally native businesses from scratch: Rent the Runway and Jetblack. During her time at Rent the Runway, Jenny wore many different hats, serving as President, Head of Logistics, and Head of Business Development.
Jenny has been honored with numerous recognitions including Inc. Magazine’s “30 Under 30”; Fortune Magazine’s “40 Under 40” and “Most Powerful Women Entrepreneurs”; and Fast Company’s “Most Influential Women in Technology.”
Helpful Links
Fast Company: Inside Rent The Runway’s Secret Dry-Cleaning Empire
Harvard Business Review: Women-Led Startups Received Just 2.3% of VC Funding
Next Episode
Educating the World: Geetha Murali @ Room to Read
Geetha Murali, CEO of Room to Read, talks with Jesse about her work in ending illiteracy and gender inequality, the importance of consistent skill building in one’s career, reflections on a career shift, and her vision for the future of education. Geetha shares how her mom refused a marriage at 13, leaving home to become a nurse and move to the United States. Geetha shares how her mother’s determination and father’s affable serenity helped shape her growth and values in ways that helped her become an effective builder. She shares insights into how education changes and benefits children, and their communities, including success stories she has helped build at Room to Read.
Geetha shares practical insights on how she collaborates with local leaders, governments, and schools to create sustainable change, and about how Room to Read has scaled with the goal of impacting 40 million children by 2025. She shares her transition from statistician to non-profit leader to CEO and her thoughts on how to have a positive impact no matter where you work. She shares her secrets to success, including how she views the importance of education and relationships.
How does education influence your success and the success of the people you care about? How do relationships and cooperation factor into your success? How do you plan your career to include meaningful impact? How do you rethink your strategy to scale into the future?
(6:28) How Geetha learned the value of education from her mother’s trailblazing journey
(16:08) Geetha describes moving beyond achieving goals, to fulfilling her purpose
(24:05) How Room to Read grew to impact 40 million children worldwide
(33:05) The central role that reading plays in developing empathy
(34:44) Advice for anyone pursuing a career in the nonprofit sector
(38:51) Jesse asks: Which influential people do you want to meet through your work?
Guest Bio
Dr. Geetha Murali is the Chief Executive Officer (CEO) of Room to Read, an organization that believes World Change Starts with Educated Children.® Room to Read is creating a world free from illiteracy and gender inequality by helping children in low-income communities develop literacy skills and a habit of reading, and by supporting girls to build skills to succeed in school and negotiate key life decisions. The organization collaborates with governments and other partner organizations to deliver positive outcomes for children at scale. Room to Read has benefitted more than 18 million children across 16 countries and 37,000 communities and aims to reach 40 million children by 2025.
As Chief Executive Officer (CEO), Geetha oversees Room to Read’s global operations, which include programmatic work in 16 countries, a global network of investors and volunteer chapters, and a worldwide staff of approximately 1,600 employees.
Geetha on Twitter: https://twitter.com/gkmurali
Room to Read Website: https://www.roomtoread.org/
Helpful Links
So Good They Can’t Ignore You, a book recommended by Geetha that was seminal to her early in her role as Room to Read’s CEO
“How to Citizen” podcast by Baratunde Thurston
Room to Read success story of Kamla
BBC World Radio interview on COVID-19 impact on girls’ education
Geetha op-ed on the power of books on our mind
“Six Terrific Book Ideas for Getting Girls into Tech” interview with Geetha Murali and Youtube CEO Susan Wojcicki in Wired Magazine
Geetha’s background and story, shared by the Shakti Collaborative
Michelle Obama & Julia Roberts meet with Room to Read kids in Vietnam
Award from the Library of Congress for Room to Read’s special response to COVID-19
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