Ashkan Karbasfrooshan is founder and CEO of WatchMojo. One of the most popular brands on YouTube with 40 million subscribers, their 25,000 videos have been viewed 17 billion times, and last year surpassed 100 billion minutes of watch time. Founded in 2006, the company has 50 full-time employees with offices in Montreal, New York City, Los Angeles and London. In this in-depth interview, Ashkan shares the highs and lows of his entrepreneurial journey – from starting the company at 27, facing financial and courtroom difficulties, eventually becoming profitable by “running out of ways to fail” and then winning Ernst & Young ‘Entrepreneur of the Year;’ discusses his relationship of “mutual dependence” with YouTube, working through copyright issues by encouraging a change in policies at the platform to protect WatchMojo’s content; and shares his ambitions to become “the most admired media company in the world” – and how he plans to get there.