Mattress shopping never sparked joy — until Casper came around. Philip and his coworkers have upended the industry and now have a $1.1 billion dollar valuation. Philip shares his vision for the future of sleep, how to scale a brand (both digitally and in retail experiences), how he thinks about the competition, and tells us about the synchronous run-in at a co-working space that led to Casper.

After working for 8 years as a Wall Street Journal reporter, Jessica set out to build a new content model - a subscription business founded on a simple premise: create articles worth paying for. Jessica shares why she became an entrepreneur, how she learned to make decisions quickly, and how content consumption will evolve over the next decade.

Umbrella is on a unique mission: the startup is aiming to help people 65+ stay in their homes longer. The demographic they serve is not only one of the fastest-growing, it's also an audience that avidly uses tech. Lindsay shares what excites her about the market opportunity, how product testing uncovered key wins, and most importantly, how she makes it work with her cofounder, Sam Gerstenzang.

Chances are, you've experienced Danny Meyer's brilliance. He's the founder behind Union Square Hospitality Group, which holds a remarkable 28 James Beard awards and is responsible for Shake Shack, which now has over 250 locations worldwide. Meyer opens up about what he looks for in new hires, how he took the leap into the food world, and shares his scariest moment to date (spoiler: getting punched in the face by a diner).

Brynn Putnam is no stranger to building businesses. In 2010, she started Refine Method, the award-winning boutique fitness studio. Now, she's the Founder & CEO of MIRROR, tapping into the $14 billion dollar home fitness market with a connected fitness system that streams classes to users in-home, all via (you guessed it) a mirror. Putnam shares how she came up with the idea and built her first prototype, the surprising range of users who love the platform, and how her professional dancing career makes her a stronger CEO.

Founder of Airtable, Howie Liu, built his first company at age 20 and sold it to Salesforce just a year later. The second time around, he's built a new platform that's already valued at over a billion dollars, putting Airtable in the rarified group of unicorn tech companies. Liu shares how he's found success via a slow and steady approach, his aspirations to become the next great tech company, and why he prefers farming metaphors to the wartime ones so often used by entrepreneurs.

Founder of Propel, Jimmy Chen, is working to build anti-poverty software. With their first product Fresh EBT, Propel is using technology to transform the experience of using food stamps for millions of Americans. Chen explains how he’s building Propel at the intersection of social good and profit, his above-and-beyond approach to gathering user feedback, and how he plans to expand his team.

Jenny Fleiss, JetblackCo-Founder of Rent the Runway, Jenny Fleiss shares when she had her "aha moment" for her new venture Jetblack, what it's like to start a company under the umbrella of Walmart, and why shopping via text is so sticky for consumers. Plus, learn what motivates her for the week ahead.