How I Failed: A Candid Conversation With A Tech Executive And Venture Capitalist

Dave Morin grew up in Helena, Montana’s capital city of thirty-thousand people. Nestled against the Rocky Mountains, it is a great place to spend as much time in the outdoors as possible and Morin skied for the northern division of the U.S. Junior Olympic team. But he also enjoyed himself indoors: since his dad bought him a classic Macintosh, Morin has been interested in computers.

Fast-forward to early 2000 and, after graduating from college, Morin moved to Silicon Valley to work in Apple's college marketing division. He then joined Facebook as senior platform manager, becoming “Facebook employee number 29.” Yet, after growing increasingly disillusioned by Facebook's privacy violations, Morin decided to leave the company and set out to co-found his own social network Path.

Designed to be more privacy-aware, Path quickly became a competitor to Facebook. At its peak, the service had around 50 million users, with Google attempting to buy it for $100 million. But things started to go sour and in 2015 the company was sold to Korea’s messaging and internet giant, which ultimately closed its operations last year.

This is just a short recap of a personal story that tech executive and venture capitalist Dave Morin shares with Gimlet Media co-founder and CEO Alex Blumberg in his podcast Without Fail, the show where "entrepreneurs, artists, athletes, visionaries of all kinds [talk] about their successes and their failures, and what they’ve learned from both". We've probably all heard it before: a dedicated protagonist has a dream, works hard, moves to a big city, achieves "success", but then something goes horribly wrong, and only through a series of personal breakthroughs, their life and vision of it changes. But however cliché it sounds, there is still a lot we can learn from it.