Growing up in New Jersey in the 1980's and 90's, Gary Vaynerchuk honed his business skills trading baseball cards and selling wine at his dad's liquor store. He discovered the potential of Youtube early on and launched Wine Library TV, an unfiltered, in-your-face wine review series that boosted the family business and branded Gary as an early social-media guru. From there, his marketing career exploded, and suddenly Gary Vee seemed to be everywhere: consulting, speaking, vlogging, tweeting, and publishing best-selling books, all while growing what is now a sprawling media company, VaynerX. His energy can be exhausting and his critics think he's full of it, but Gary shrugs them off; he credits much of his success to his immigrant upbringing and his parents' strong work ethic. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Robert Reffkin had a hard time fitting in when he was growing up: raised by a single mom in Berkeley California, he was both bi-racial and Jewish, and had to learn to "feel comfortable with being uncomfortable." Even though he was a self-described C student, he was admitted to Columbia and landed a series of prestigious investment banking jobs, but often felt like he was failing. Then in 2012, Robert was tasked with writing a business plan as part of a job interview, but the plan was so intriguing that he was encouraged to launch it as an actual business. So with a partner, Robert launched Compass, a real estate company that focused on building technology to make agents' jobs easier. Less than ten years after launch, Compass is a publicly traded real estate brokerage with about 20,000 agents, valued at around $6 billion. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Our second episode from the 2021 How I Built This Virtual Summit is from our innovation panel with Payal Kadakia of ClassPass, Tristan Walker of Walker and Company, and Perry Chen of Kickstarter. In this live conversation with Guy, the panel talks about how innovation doesn't require newness, but rather, authenticity. We'll be releasing more episodes from the Summit, so keep checking your podcast feed. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Bobbi Brown started out as a makeup artist in New York City, but hated the gaudy color palette of the 1980s. She eventually shook up the industry by introducing "nude makeup" with neutral colors and a natural tone. In 1995, Estée Lauder acquired Bobbi Brown Cosmetics and Bobbi remained there for 22 years, until she realized the brand was no longer the one she had built. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the late 1990s, Ben Chestnut was a struggling young designer interning at an appliance company, when somebody suggested that he try designing for the internet instead. A few years later, Ben and two co-founders launched a web design agency, only to discover that the service they'd included almost as an afterthought—email marketing—was taking off among their small-business clients. The founders named that service Mailchimp and pivoted to it full-time in 2007, choosing a winking monkey as their mascot, and stumbling onto the Freemium model before it became mainstream. But their most impeccable timing came in 2014, when they decided to sponsor a new podcast called Serial, a move that catapulted the winking monkey into popular culture. Over the years, despite management jitters and a public reckoning over office culture, Mailchimp has remained profitable and self-funded, with revenue of $800 million in 2020.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

When they were in their 20s, Reem Hassani and her brother Ahmed Rahim were not the kind of people you'd expect to launch a multi-million dollar business. Reem was a California artist moonlighting as a substitute teacher, and Ahmed had been living the bohemian life of a photojournalist in Europe. But these two children of immigrants from Iraq had an idea: to introduce the dried lime tea they remembered from their childhood to the U.S. Working out of Reem's 600-square-foot apartment in Oakland, the siblings learned all about the challenges of lining up importers, packagers, and retailers to launch a premium loose-leaf tea brand—meant to be slowly steeped and savored. More than twenty years after it's launch in 1999, Numi Organic Tea is a privately held B Corporation that sells tens of millions of dollars of Fair Trade, organic tea every year. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the early 2000's, Philip Krim launched an e-commerce business out of his college dorm, selling everything from window blinds to eczema cream to yes, mattresses. Years later, inspired by online successes like Warby Parker and Harry's, Philip and his partners launched Casper, a DTC company that designed its own mattresses, compressed them into boxes, and helped turn a mundane purchase into an Instagrammable adventure. Within months, sales began to take off; and soon, copycat brands crowded into the DTC mattress space, creating competition and buzz in a previously sleepy sector. (Pun unavoidable) Despite these challenges, Casper's valuation soared to $1 billion in 2019, only to shrink by half for its 2020 IPO. Today, Philip says he's focused on the future, with ambitions to build Casper into a one-stop-brand for all things sleep-related. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Our first episode from the 2021 How I Built This Virtual Summit is from our leadership panel with Cynt Marshall, CEO of the Dallas Mavericks, Chieh Huang, CEO and co-founder of Boxed, and Sadie Lincoln, CEO and co-founder of Barre3. In this conversation with Guy, the panel talks about the importance of showing vulnerability, and how leaders can build trust within their teams. We'll be releasing more episodes from the Summit, so keep checking your podcast feed.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

By her early thirties, Ava DuVernay was already a successful entrepreneur, having founded her own film publicity agency in Los Angeles. But after years of watching other people make films, she started to get an itch to tell her own stories onscreen. Ava's first films were rooted in deeply personal experiences: growing up with her sisters in Compton, performing Hip Hop at Open Mic Night at the Good Life Café in L.A. Her self-funded and self-distributed projects began to draw attention, and in 2012, Ava won the award for best directing at the Sundance Film Festival. She went on to direct powerful projects like Selma, 13th, and When They See Us; and through her production and distribution company ARRAY, she's created a movement that is helping change how movies are made—and who gets to make them.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the early 90s, Rich Barton arrived to work at Microsoft just as the world wide web was taking off. He wound up pitching Bill Gates on an idea that was transformative at the time: to let everyday travelers book their own flights and hotels by giving them online access to previously hidden reservation systems. Expedia launched from inside Microsoft but was so successful at transforming the travel industry that it was spun out into a public company with Rich as CEO. Then in 2005, Rich moved on to a new idea with some Expedia colleagues, co-founding Zillow as a way to "turn on all the lights" in another sprawling industry: real estate. When the site launched in 2006, so many people tried to look up their home-value "Zestimates" that the site crashed within hours. By 2020, pandemic-era interest in housing saw Zillow accessed almost 10 billion times. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.