While insurance is a $5 trillion dollar market, Daniel noticed an opportunity: most insurance companies are not described as lovable or delightful. He wants consumers to forget everything they know about insurance and start fresh. Daniel shares how Lemonade leverages technology to build trust, how they've achieved an NPS of 70+, and why keeping Shabbat each week helps him set healthy boundaries as a founder.

70% of American employees work in open floor plan offices—and according to Brian Chen, they don't like it. Brian and his cofounders set out to reimagine the modern workplace and launched their first product, an office phone booth (which already graces the offices of Google, Apple, and J.P. Morgan). Brian shares his own frustration with not being able to find a quiet space at work, explains how he and his co-founder personally delivered and assembled their first prototypes, and why they care about being responsible citizens of the world.

Bobbi Brown began her career as a freelance makeup artist. She didn't set out to build a billion dollar makeup business, but she quickly accelerated from creating a line of lipsticks to an acquisition by Estee Lauder four years later. Bobbi went on to spend nearly two decades building Bobbi Brown into a household name. Bobbi shares how she adapted to being a corporate employee post-acquisition, why being able to wear jeans to work matters, and how she interviews for work ethic.

Aaron Levie dropped out of college and moved into his uncle's garage to launch Box. Fast-forward and the company has 95,000 enterprise customers and a $3 billion market cap. While one of his first win's was securing an investment from Mark Cuban off of a cold email, it wasn't always an easy journey. Aaron shares how he zeroed in on the right business model, how he hires for culture adds, and why startups have to be 10X better in some way (like simplicity).

Justin McLeod has an unusual mission: build a dating app designed to be deleted. It was his own offline love story that helped him gain clarity into his vision for Hinge and guided the company through a critical pivot. Justin shares what it was like to be acquired by the Match Group, why he thinks social media is the new smoking, and how to know when a new business strategy is working.

From the time she was a teen, Misha Nonoo dreamed of becoming a fashion designer. She has since grown her women's apparel company into a powerhouse that constantly stays ahead of seismic shifts in the retail landscape. Misha shares why she forewent the wholesale model to gain a direct relationship with her customer, why sustainability is critical to the future of fashion, and why discipline is the most important trait for entrepreneurs to embody (and to hire for).

After meeting as freshmen at Georgetown, Jonathan and his two-cofounders set out to open a healthy fast food restaurant in a 500 square feet storefront. From those quaint beginnings, Sweetgreen has grown into a massive food platform, with over 100+ locations and 200+ outposts. Jonathan shares why authenticity is core to the brand, why their inexperience actually enabled innovation, and how he thinks about falling on the right side of this equation: as companies get bigger, they either get better or worse.

From her parents' house to two million+ monthly readers, Leandra has built a media business at the forefront of fashion. With a firm belief that quality content should drive all, the Man Repeller team has grown to over twenty employees and continues to innovate into new lines of business. Leandra shares the blessings (and curses) of building a brand on social media, why creativity is a key ingredient for a great day at work, and the difference between being a good leader and a good boss.

Susan started Framebridge out of a personal paint point: she tried to frame a series of National Parks posters and realized the process was both confusing and expensive. With $82 million in funding and a major facility in Kentucky, Framebridge has fundamentally transformed the experience for consumers across the country. Susan shares why she always does the hard thing first, the challenge of managing seasonal spikes in business, and how she doesn't waste time on guilt as a working parent.

There's something about sneakers. It's one of those rare product categories that can get people to line up around the block. GOAT has made a huge dent in the sneaker scene, building a managed marketplace that currently lists over 1 million sneakers. Eddy shares how GOAT authenticates the product moving across their platform, how he thinks about online vs. retail sales, and what it was like to acquire a sneaker pioneer as a new upstart.

Shan-Lyn Ma is transforming the wedding business. After graduating from Stanford Business School and joining Gilt as their first product person, Shan launched Zola in 2013—and has already helped over half a million couples. Shan shares why product is so important to every business, how to get smart (and actionable!) consumer feedback, and the real story behind Zola's creative name.

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.