Some choice quotes:

“It’s like the fight club of management: The first rule of the CEO psychological meltdown is don’t talk about the psychological meltdown.”

“Which interpretation was closer to the truth? In the absence of someone to talk to, that’s a question that I asked myself about 3,000 times. As an aside, asking oneself anything 3,000 times turns out to be a bad idea.”

“Tip to aspiring entrepreneurs: if you don’t like choosing between horrible and cataclysmic, don’t become CEO.” 

“At times like the above, it’s important to understand that nearly every company goes through life-threatening moments. My partner Scott Weiss relayed that it’s so common that there is an acronym for it: WFIO which stands for We’re F#%ked, It’s Over (it’s pronounced whiff-ee-yo).”

“A Final Word of Advice—Don’t Punk Out and Don’t Quit. As CEO, there will be many times when you feel like quitting. I have seen CEOs try to cope with the stress by drinking heavily, checking out, and even quitting. In each case, the CEO has a marvelous rationalization why it was OK for him to punk out or quit, but none them will ever be great CEOs.”

I remember at a board meeting at Powerset Peter Thiel asked us how the morale of the company was going.  Like all founders at board meetings, we said it was going great.

Peter said “let’s prove it.”

What we did is offer the following:

1. Anyone can voluntarily, permanently reduce their salary by one or more strata levels,
2. For each competency level forfeited you get XX,XXX more ESOP shares.

That’s from Steve Newcomb, the founder of Powerset, in a post that contains the most thorough, nearly step by step advice on implementing good hiring practices and culture at a company that I’ve encountered.

It’s long but worth the read.

For those who don’t know what Powerset is, Microsoft bought it for $100 million and it essentially became Bing. Steve Newcomb wasn’t the guy I met or insulted though. That co-founder of Powerset was Lorenzo Thione, and I insulted him as at a gay piano bar in New York called Marie’s Crisis.

After drunkenly begging the piano player to play “Gary, Indiana” (It was musicals night and that was the only musical song I knew any of the words too, plus, my friends and I were all from Indiana. No one in the bar was happy about this song choice.) my friend told me a guy he was talking to was from the Valley and that he’d started a company.

That’s all I knew. I had no idea who Lorenzo Thione was or what Powerset was. I can’t tell you exactly how that conversation went except that I didn’t hesitate to tell him that I thought starting a search engine was a dumb idea. I didn’t mince my words.

At that point in time, I was skeptical of anything that sounded like a “me too” idea to the point that I acted supercilious towards anyone not working on something innovative, and in my first 2 minutes of talking to Lorenzo, that’s how I assessed the situation. (Remember, I was drunk enough to request “Gary, Indiana,” and even that doesn’t begin to describe my state of inebriation. Also, I think there were a lot of new search engines in the news around that time like Cuil and WolframAlpha which really did disappoint)

I probably talked down to this guy for a good 10 or 15 minutes and he just heard me out. He never once took a shot back at me or even really acted annoyed.

He asked about me and I told him I had just started a company and was working on it full-time. He asked where I was from and I told him Indianapolis, and the only thing he had to say about me was “You’re trying to start a company? Then why are you in Indiana?”

Well, somehow I stumbled back to my friends apartment after that conversation. In the morning, I remembered just enough of Lorenzo and Powerset to do a Google search.

At this point, I still had no idea I was talking to anyone of any significance. For all I knew, I was just talking to another entrepreneur at the same stage as me in starting a business.

But then Google showed me that I was actually talking to a guy who had helped build one of the most powerful natural language search engines ever built.

Foot in mouth. Open palm to forehead.

Sometimes I think what a wasted opportunity that night was, but usually, after I cringe from nostalgic embarrassment, I just think how much that event cleared away a bunch of my unhealthy bravado. There was a lot more bravado clearing as I proceeded to start my first company, but never again was so much cleared in one swoop.