YouAre.TV founder and General Assembly alum Josh Weinstein is back in New York after an ill-fated adventure in Palo Alto, taking with him his hockey pads and leaving behind a flaky coder who was supposed to become YouAre.TV’s CTO.
Mr. Weinstein penned a tell-all-blog post in which he explains how Palo Alto was fun at first, what with all the hanging out at Facebook and Google, and how he got to play hockey with Guy Kawasaki (more than once!) and had a stand-up desk. Of course, it was superangel Peter Thiel who convinced Mr. Weinstein to move to the Valley–Mr. Thiel regards the bright young founder as an accolyte–so Mr. Weinstein was able to be close to his mentor. “At first, we wondered if Mr. Thiel just wanted to have someone to play chess with. But YouAre.TV just recruited a new CTO, so we guess there are still plans to build a company,” Betabeat wrote in a rumor roundup at the time.
Sadly, things quickly went sour. Mr. Weinstein discovered Palo Alto was understimulating. “As a city kid, I started to feel the isolation of living in Palo Alto and not working in a coworking space,” he wrote. To make things worse, his CTO wasn’t working as much as promised–and kept pushing back his start date.
“Sure enough, after midnight on the day Ted and I were supposed to really start (after pushing back a month and then a week), I received an email from him titled “Involvement with youare.tv going forward,’” Mr. Weinstein writes.
If you want to write a maximally cold and destructive break-up letter to your cofounder, here’s how to do it. We’ve included the letter from Mr. Weinstein’s almost-CTO with annotations below:
Hope you had a good trip back. [open with friendly greeting, the limpness of which will contrast with the rest of a letter which will have devastating consequences]
Would like to discuss with you about my involvement with youare.tv, and I am sorry for the change. [understate and euphemize wherever possible--"my involvement" for "our signed agreement that I would be your technical co-founder"]
Things have changed in last 36 hours, since a few people I am leaving [company name redacted]. [act as if there was no way you could see this coming]
There are a few very exciting opportunities just surfaced, from idea stage to growth stage, and all are working on very disruptive products and technologies, [sideways insults implying that vague "exciting opportunities" are cooler and more disruptive than the startup you had committed to]
All these sounds exciting, and I would definitely like to explore further – still too early to tell, but sounds very exciting.
Would like to discuss how I can best help youare.tv going forward, maybe an advisor role to help you recruit a few engineers to work on the product. We can meet early next week to discuss further. [empty promises are essential]
Also, I will not be available Monday, but can meet together Tuesday afternoon. [put caveats on any offers to help--the more they emphasize how busy and in-demand you are, the better]
I am very sorry about this change – really get attracted to the news things. [a brilliant kicker that showcases what an idiot you are and therefore what an idiot your partner must be]
Cheers! [overly cheery closing provides striking contrast to gravity of the situation]
Mr. Weinstein is left to take another lesson from failure. His first start-up, CollegeOnly, arguably failed because it got too much hype in the beginning, between 10,000 initial sign-ups and a million bucks from Mr. Thiel before the product was ready for primetime. But Mr. Weinstein took the most successful aspect of CollegeOnly, which was a dorm-to-dorm video chat, and spun it off into a new startup focused on interactive, web-native video entertainment with gaming elements. The result is YouAre.TV, an interactive game show which looked bonkers and confusing when Betabeat saw it demo’ed but was obviously very innovative–and fun.
As one of my former chess coaches, Svetozar Jovanovic, always said “You learn a lot more from a loss than you do, if anything, from a win.” While it’s always better to win, the lesson learned here above all else is there is only one person you can really, truly trust in making critical decisions and executing thereupon – yourself. As noted, trust is critical – and if your gut indicates you you probably can’t or shouldn’t trust someone – either exhaustively figure out and deal with it, or, more likely, hit the big red stop button and shift gears.
Yes, in case you were wondering, we are looking for a CTO with significant experience in the bi-directional video space and management/recruiting experience.