Ocient CEO & Co-Founder Chris Gladwin reveals his methods for building businesses that meet the demands of Enterprise customers, and outlines his plan to help build Chicago into a major center for technology.

VaynerNFT President Avery Akkineni describes her journey to becoming a leading voice in the NFT space, and shares her view on what consumers and brands need to know about NFTs and blockchain technologies.

How Hydrow CEO & Founder Bruce Smith created a revolutionary in-home rowing experience to disrupt the sport’s culture of exclusion and introduce more people to the beauty of rowing.

Geetha Murali, CEO of Room to Read, discusses the importance of building skills and relationships in the quest to educate 40 million children.

LivePerson Founder & CEO Rob LoCascio discusses the beautiful journey of entrepreneurship, the impermanence of failure, and the breakthrough innovations driving a new age of conversational commerce.

How Jenny Fleiss, co-founder of Rent The Runway, created the “closet in the cloud” to bring high-end fashion experiences to everyone, and how she’s guiding the next generation of entrepreneurs with expertise and empathy.

Peloton’s Jessica Kleiman reflects on her career and life experiences as a storyteller, and shares her perspective on the value of authenticity in corporate communications and community stewardship.

Season 5 Theme: Building Experiences at the intersection of Technology & Purpose

First two guests: Jessica Kleiman (SVP of Global Communications, Peloton), Jenny Fleiss (Co-Founder of Rent The Runway and Partner at Volition Capital)

Prime Roots CEO & Co-Founder Kim Le on her company’s mission to change the hearts, minds, and refrigerator share of every omnivore and flexitarian on the planet.

Underdog Brad Balukjian lays out the premise of his bestseller The Wax Pack, talks about the danger of expectations, and describes how discovery and vulnerability came together on his journey to discover baseball’s afterlife.