Groupon and Descript: Andrew Mason

Today’s callers: Yadi from New York thinks through an expansion strategy for her college campus-based empanada business. Then, Zachary from New York looks for ways to break into big retailers with his fresh-made frozen pies. And Josh from Indiana wonders how to go all-in on his s ...  Show more

Before Spinbrush became the top selling toothbrush in the U.S—and before Procter & Gamble paid $475M for it—John Osher was a teenager selling earrings for $4.99. In this episode, John walks through the strange, scrappy, but disciplined path that led to one of the fastest consumer ...  Show more

<span style="font-weight: 400;">Andrew Mason is the founder and former CEO of Groupon… who had a VERY public firing. Today, I'm talking to Andrew about what he learned getting fired from the company he helped create, how he dusted himself off to start a new business, and more. ...

Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $ ...  Show more

Ben and David return to make their first foray into enterprise software, covering Salesforce’s $2.5B acquisition of ExactTarget in 2013 with the help of special guest and ExactTarget cofounder & CEO, Scott Dorsey. Technical note: due to an issue we didn’t catch during recording, ...  Show more

Nathan Barry, the creator behind ConvertKit (now rebranded as Kit) came to visit my Inner Circle and gave a very special presentation. Nathan’s journey from a designer to building a software empire fascinated me. He originally tried to solve his frustrations with MailChimp and, i ...  Show more