Carey Smith is the founder of Unorthodox Ventures and Big Ass Fans, a company that he built to $250 Million in revenue and then sold for half a billion to a private equity firm.

We asked Carey Smith how he built Big Ass Fans from scratch, why he sold it, and how he chooses the entrepreneurs to support for his new business Unorthodox Ventures.

Davis Smith is the CEO of Cotopaxi, a company that sells a premium line of outdoor gear. Before founding Cotopaxi, a B-corp that has been a subject of a Harvard Business School case study, Smith had founded two other companies: baby.com.br and pooltable.com.

We asked him how he went from selling baby products in Brazil and pool tables in the US to founding Cotopaxi, and what being a certified B-Corp means to him and his business.

Adrian Aoun is the CEO of Forward, a preventive healthcare company which he co-founded with former employees of Google and Uber.

Aoun is also the founder and former CEO of Wavii, which he sold to Google for $30 Million, and a prolific angel investor with dozens of successful bets including Pinterest and ClassPass.

We talked to him about Forward’s business model and mission to reveal and dismantle the absurdity of America’s healthcare system.

Matthew Berk is the founder and CEO of BeanBox, the leading online coffee subscription service. BeanBox is an Inc. 5000 company and one of the fastest-growing companies in America with a community that is a couple hundred thousand strong.

We talked to Mathew Berk about what makes a subscription business stand out from the crowd, the role technology plays in business today, and BeanBox’s most effective methods for customer acquisition.

Fritz Lanman is the CEO of ClassPass, one of the fastest growing online fitness startups. ClassPass recently joined the Unicorn Club after getting an valuation of one billion dollars.

Lanman is also an angel investor in various successful startups such as Pinterest, Wish, and Square. We talked to him about the creation story of ClassPass, how he became the CEO, and the secrets to investing in companies that end up extremely successful.

Elan Lee is the CEO and co-founder of Exploding Kittens, the popular card game that sold over 10 million copies and set a crowdfunding record by raising 9 Million from 220,000 backers.

In this episode of How We Made It In E-Commerce, Elan generously shared his methods for coming up with new ideas, creative business and marketing hacks, and the most important lessons he learned throughout his career about running a business.

In this episode we talk to Shayan Zadeh, the co-founder of Zoosk (sold for $250 Million) and now the CEO of Dressbarn. Discover:

By Capital & Growth

Your host for this episode: Elyse Hauser

Sahil Lavingia is the founder of Gumroad, an ecommerce platform that allows creators to monetize their wares. As of June 2019 Gumroad has paid out more than $200 million to creators. 

He once thought success meant building a billion-dollar company. One very public failure later, he considers himself successful for completely different reasons.

“Money is money,” Lavingia says. “My experiences that I’ve been able to have, and this path, have been pretty great.” Gumroad will never be worth a billion dollars, but Lavingia is content to run it as a smaller company with no plans for scaling up. How did he go from billion-dollar dreams to this relaxed acceptance?

Once upon a time, Lavingia was the second employee at Pinterest -- a company now valued at $12 billion, and rumored to be going public this year. He left Pinterest before his options vested hut he doesn’t look back on the decision to leave wistfully. “I think regrets are mostly a waste of time,” he says. “I try not to think too much in hypotheticals.”

That same attitude helped him turn what many would call a start-up failure into an unconventional success.

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