Welcome to this week's conversation with fellow Stuyvesant High School alum and tournament chess player Josh Weinstein, CEO of YouAre.TV
Josh takes us through the labyrinth of ideas, projects, adventures and startups that have marked his remarkable entrepreneurial journey thus far. From winning the National Speed Chess Championship to launching Stuycom in highschool, to his experiences launching FreshPrince, CrushFinder, GoodCrush, RandomDorm, College Only and most recently YouAreTV- to getting funded my multiple prominent angels and VC's including Peter Thiel, Josh has a fascinating story to tell and he does so with arresting candor and a great sense humor. This was some of the most fun I've had thus far at Venture Studio and I learned that there is definitely a method to Josh's madness! Enjoy.
Below is a short table of contents (with corresponding minutes) of our conversation:
00:33 How Josh got into chess & became US Speed Chess Champion
01:27 Becoming a tech entrepreneur while @ Stuyvesant High School
02:55 The Princeton years: FreshPrince, CrushFinder & GoodCrush
04:15 Graduating, raising seed money for GoodCrush and iterating
04:46 Adding RandomDorm to the mix & raising more capital
05:28 Genesis: College Only (GoodCrush, RandomDorm & YouAreTV.com)
05:53 Josh describes overcoming challenges and mistakes w/College Only
07:53 What can only be described as the "method to Josh's madness" :)
08:20 Lightbulb goes off: "Thiel is a chessplayer!!" More on Peter Thiel
09:37 Josh explains YouAreTV.com & the Game of Boxes
12:18 The YouAreTV.com team & Josh is Hiring!
12:49 Josh discusses importance of focus, shares candid insights