When Andy Dunn was in business school, his housemate Brian Spaly created a new type of men's pants: stylish, tailored trousers that fit well in both the hips and thighs. Together, they started the men's clothing company Bonobos, which became an instant hit due to the pants' signature flair and innovative e-commerce experience. But within a few years, Andy hit challenging roadblocks, including a struggle with depression and a falling-out with his co-founder and friend. Despite many moments of crisis, Andy steered Bonobos to massive success, and in 2017, it was acquired by Walmart for a reported $310 million.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

After working in the furniture and home goods industry for over a decade, Mitchell Gold took a risky bet and decided to start his own furniture company. In 1989, he went into business with his romantic partner, Bob Williams, who had been working in advertising as a graphic designer. They contracted with a furniture factory near their home in Taylorsville, North Carolina, and launched a line of boldly-patterned upholstered dining chairs and eclectic dining tables, leveraging Bob’s design skills and Mitchell’s industry experience. Roughly thirty years later, Mitchell Gold + Bob Williams is a multi-million dollar brand with hundreds of employees, which sells a full range of home furnishings at retail locations nationwide.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Matt Mullenweg turned his early passion for blogging into a flourishing business and an unshakeable idea: that users should be able to share and tweak the code that powers their websites, and that most of those tools should be free to use. As far back as college, Matt was collaborating with far-flung fellow-coders to make blogging less clunky and more elegant and intuitive. Around 2005, he pitched the idea for WordPress.com to his bosses at CNET, but they turned him down, so he launched the idea on his own, eventually tucking the service into a nascent umbrella company called Automattic. Today—after many twists and turns—the company has nearly 2000 employees and a valuation of $7 billion; and WordPress powers more than 40% of the websites on the internet. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

With no strategic plan and very little money, Sukhi Singh figured out a way to sell Indian food at scale across the U.S.—but it took her almost 20 years to do it. In the early 1990's, she shuttered her faltering café in Oakland, California and enlisted her husband and three children to help her sell bottled curry paste at local stores—and Indian meals at farmers markets. But the real breakthrough came when Sukhi expanded into refrigerated/frozen meals, and landed her chicken tikka masala and samosas in Costco. After growing the family business without a cent of outside investment, Sukhi's Gourmet Indian Food is now one of the biggest Indian food brands in the U.S, with over fifty products available in around 7,000 stores.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

During his early career, Jason Citron stepped away from two stalled businesses and pivoted—twice—to something far more successful. The second time he did it, he created one of the most popular social media platforms in the world. It started at age 13 when Jason had a “holy crap” moment, discovering he could make his own video games. His first video game company morphed into a social platform for gamers, and after he sold it, he couldn't resist launching another. When that business failed to get traction, he again re-imagined it as a digital space for gamers to gather, and in 2015, Discord was born. Today, the platform has 150 million monthly users, and is a gathering place not just for gamers, but for anyone who wants to connect with friends. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The very first time Tristan Walker shaved, he woke up the next morning with razor bumps all over his face. "I was like, what is this?" he remembers saying. "I am never shaving again—ever." He soon discovered that like him, many men of color were frustrated by the lack of shaving products for coarse or curly hair. Fifteen years after that first disastrous shave, and after countless meetings with doubtful investors, Tristan launched Bevel, a subscription shaving system built around a single-blade razor. Eventually his brand Walker & Company grew to include 36 hair and beauty products, used by millions of men and women across the U.S. In 2018, Walker & Company was sold to Proctor & Gamble, and Tristan became P&G's first black CEO. This show was recorded live at the Lincoln Theatre in Washington, D.C in September 2019. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Angie and Dan Bastian weren't trying to disrupt an industry or build a massive company, they just wanted to put aside some money for their kids' college fund. In 2001, Dan stumbled across an internet ad touting kettle corn as a lucrative side-business, so he and Angie decided to take the plunge, investing $10,000 in equipment. At first, they popped kettle corn in front of local supermarkets in the Twin Cities and at Minnesota Vikings games. Eventually, they moved indoors to Trader Joe's, Target, and Costco—and got a crash course in how to run a business along the way. Angie's Kettle Corn eventually took on a bold new name: BOOMCHICKAPOP. And in 2017, the company was acquired for a reported $250 million. This show was recorded live at Ordway Concert Hall in St. Paul, Minnesota in July 2019.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As he started to gain a name as a New York fashion designer in the 2010s, Telfar Clemens often joked that he was "constantly emerging." At least, that's how the establishment fashion press saw him: a child of Liberian immigrants, building a small but devoted following with his deconstructed T-shirts and sandals made from hollowed-out Converse. But after Telfar partnered with Babak Radboy as his creative director in 2013, the brand began to reach a wider audience. There were splashy partnerships with K-Mart and White Castle; and in 2018, the wide release of the Telfar Bag, a vegan-leather shopping bag that became the "it"-accessory for everyone from A-list celebrities to the neighbors next door. Today, Telfar and Babak say they've succeeded by designing exactly what they want—and sidestepping a fashion system that was not always welcoming. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As a young programmer in the mid-2000s, Otis Chandler watched as dozens of niche web sites began to take off. When he decided to launch his own site just for book lovers, a respected colleague told him there was "probably not a very big market there." Otis figured he might prove him wrong, and in 2007, launched Goodreads, a book catalog and review site that he coded from his LA apartment. His soon-to-be-wife Elizabeth joined the project, and they slowly built a following—without an office, a business model, or a single employee. In 2013, Goodreads sold to Amazon for an undisclosed sum; and today, it's the world's largest site for readers, with 125 million users. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Most entrepreneurs expect it will take at least a few years for their businesses to gain traction. But Tim Leatherman waited 7 years to make a single, $175 sale. In the late 1970s, he had set up shop in his brother-in-law's garage, scavenged some metal from old appliances, and built a tool that he'd dreamed up a few years before: a foldable pair of pliers with several other tools tucked into the handles. Tim worked for years trying to market his design to knife and tool companies, but none of them were interested. Was it a tool? A gadget? A knife? Eventually he was able to convince mail-order catalogs to sell the tool; and within the space of a decade, he went from selling a single knife to a million every year. Today Tim's company is worth over a $100 million and his last name has become a household brand: the Leatherman. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.