The Dealroom with Shamus Madan The Dealroom with Shamus Madan

Shamus Madan interviews Gina Gotthilf, covering her pivotal career decision with Tumblr, an unexpected experience with a former boss, and she grew Duolingo to 200M users with PR. They discuss trust and risk in startups, PR misconceptions, meeting President Obama, and her work with Latin American startups at Latitude.

In this episode, Shamus Madan interviews Chess.com's Erik Allebest about his entrepreneurial journey, the challenges of running a $100 million business, and maintaining balance. They delve into building company culture in a remote setting, growth strategies, and the impact of AI on online chess.

When Neil Parikh was in medical school, he called his parents to say he was taking a year off to move to NYC. At the time, they were furious, but little did he know that would be one of the best decisions of his life. He partnered with his friend, whom he met at a coworking space, to build a DTC mattress company. Their most recent valuation was at over $1 Billion. This is the story of Casper and the secret behind their viral growth.

At just 12 years old, Sam Obletz decided to put his studies on the back burner and start a computer integration company with his friend. Today, he has come a long way from building computers and is now on a mission to change advertising forever. This is his multi-billion dollar plan.

The education system is broken, but Tade Oyerinde is on a mission to save it with his startup Campus. He raised tens of millions from Sam Altman, Dr. Shaquille O'Neal, and many others. This is his multi-billion dollar plan.

In 2016, Joe Lemay's balance sheet for Rocketbook was -$400k, and no VC would touch him. Bootstrapping was his only option. After four years of sweat and tears, he and his co-founder, Jake, built the company to a +$50M exit. This is the story of Rocketbook.