Early in his political career, Julius Caesar is said to have wept upon reading a biography of Alexander the Great. When asked why, he apparently said, “Do you think, I have not just cause to weep, when I consider that Alexander at my age had conquered so many nations, and I have all this time done nothing that is memorable!”

—-

Earlier, to me the game meant maximizing your time and potential to get somewhere, now it meant maximizing those things to enjoy the trip.

—-

The answer to how you pick the destination: by asking yourself, what do I want to see grow? What do I want to build?

Yes, it turns out he became one of Foursquare’s earliest employees by cold-emailing Dennis and Naveen and selling them on what value he could add. 

I think it’s interesting that he sent 8 emails before Dennis finally consented to talking more about possibly bringing Tristan on. I don’t know if Dennis at least replied with “no, thanks” or “not right now” before that 8th email, but I’m not sure I would have cold emailed someone that many times, without receiving a response, before I decided that they really weren’t interested.

One of my resolutions in 2011 is to be more bold. I think cold emailing someone past my comfort zone of “I’m really annoying this person” is a good example of boldness.

At the end of the day one must ask “What’s the worse that could happen if I send this 8th email?”

This post makes me want to read his other posts. It’s brutally honest and speaks to that voice inside of us that’s always reminding us what we’re bad at. 

My favorites:

2. If you can’t be first in a category, set up a new category you can be first in.

3. It is better to be first in the mind than to be first in the marketplace.

4. Marketing is not a battle of products, it’s a battle of perceptions.

5. The most powerful concept in marketing is owning a word in the prospect’s mind.

6. Two companies cannot own the same word in the prospect’s mind.

Some of the highlights:

“Pre-dodgeball I went thru 3-4 years thinking I was going to meet some magical engineer who would build all the stuff I was thinking about.  But I never met that person, so I taught myself ASP and MS Access (yikes! eventually PHP an MySQL) out of a book and got to work just hacking stuff together.  I’m still a really shitty programmer”

“Don’t let people tell you your ideas won’t work…If you’re passionate about an idea that’s stuck in your head, find a way to build it so you can prove to yourself that it doesn’t work.”

On the First Round Capital website we write that: “We love investing in technologies and business models that are able to shrink existing markets. If your company can take $5 of revenue from a competitor for every $1 you earn – let’s talk!”…

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.

Complete with a link to a template in Google Spreadsheet