BRIAN CHESKY Gets Honest About the Future of AI, Online Dating, and Maintaining Friendships | IMO

This week, Airbnb’s co-founder and CEO, Brian Chesky, joins Michelle and Craig at the table to discuss everything from boosting a business out of the startup phase to dating in search of deep connection. Brian shares stories about Airbnb’s early keys to success (hint: it has to do with breakfast cereal), the evolving responsibility of tech companies in the modern age and how young entrepreneurs can navigate the current tech landscape. Plus, Michelle presses Brian on the dating advice he received from a surprising source during the pandemic. [00:00:00] Michelle the Matchmaker [00:03:05] Meet Brian Chesky, Co-Founder of Airbnb [00:04:30] Hosting Guests [00:07:25] The Wild Origins of Airbnb [00:12:21] Obama O’s & Captain McCain’s: Startup Hustle 101 [00:17:08] What’s New at Airbnb? Services, Not Just Stays [00:18:45] Listener Question: Are We Spending Too Much Time Online? [00:21:15] Why Brian Thinks Differently About Tech [00:25:47] The High Cost of Chasing Money [00:30:03] Reclaiming Real Connection in a Digital World [00:32:10] What President Obama Taught Me About Leadership [00:34:48] Entrepreneur vs. CEO: Making the Shift [00:38:18] Advice for Entrepreneurs in a Tough Economy [00:41:10] What Brian Would Tell Young People Today [00:46:07] Dating in the Age of Algorithms #podcast #michelleobama #craigrobinson #brianchesky #airbnb Subscribe to IMO with Michelle Obama & Craig Robinson on YouTube:    / @michelleobama   Have a question for the show? Let us know at IMOpod.com Follow us on social! Instagram: www.instagram.com/imopodcasts TikTok:   / imopodcasts   Facebook:   / imopodcasts   X: https://x.com/imopodcasts About IMO with Michelle Obama & Craig Robinson Michelle Obama and her big brother Craig Robinson bring their unique experiences and candid perspectives to a range of personal dilemmas, from the everyday to the existential. Each week, they’re joined by a special guest to tackle audience questions with practical advice, terrific stories, and plenty of laughs. From dating and relationships to parenting and financial planning, IMO sees the iconic First Lady at her most relaxed and honest. This podcast will leave you laughing, reflecting, and feeling more prepared to tackle life’s challenges. About Michelle Obama Michelle’s passion for storytelling has set sales records, garnered awards and accolades, and earned her global acclaim. Her memoir, Becoming, spent over 130 weeks on the New York Times Bestsellers list, sold more than 17 million copies worldwide, and won a Grammy Award. American Factory, the first film produced by her and her husband Barack Obama’s media company Higher Ground, won the Academy Award for Best Documentary in 2020. Upon its release in 2020, The Michelle Obama Podcast was the most successful original in Spotify history, bringing in more women listeners over 40 than any other podcast. Through the Obama Foundation, she founded the Girls Opportunity Alliance, which supports adolescent girls' education and empowerment around the world. She is also a Co-Founder and Strategic Partner of PLEZi Nutrition, working behind-the-scenes to guide the company's mission to be a driver of change and a model for how food and beverage brands can support the health of the next generation. Follow Michelle Obama on Instagram:   / michelleobama   Follow Michelle Obama on Facebook:   / michelleobama   Follow Michelle Obama on X: https://x.com/MichelleObama About Craig Robinson Craig is the Executive Director of the National Association of Basketball Coaches (NABC) and host of the Higher Ground podcast Ways To Win with Hall of Fame coach John Calipari. From 2017-2020, he served as the vice president of Player Development and Minor League Operations for the NBA’s New York Knicks. Previously, he was a Division I head men’s basketball coach at Oregon State and Brown, and spent more than a decade working as a trader in the investment banking industry. Most importantly, he is a husband and father of four. Follow Craig Robinson on X: https://x.com/craigmalrob Follow Craig Robinson on Instagram:   / craigmalrob   About Higher Ground Higher Ground was founded by President Barack Obama and Michelle Obama in 2018 to tell powerful stories that entertain, inform, and inspire—while elevating new and diverse voices in the entertainment industry. Learn more at https://highergroundmedia.com/ Follow Higher Ground on Instagram:   / highergroundmedia   Follow Higher Ground on X: https://x.com/HGMedia