"We were trying to get a big client for weeks, and they said no and went with a competitor. The competitor already had a terms sheet from the company were we trying to sign up. It was real serious.

We were devastated, but we decided to fly down and sit in their lobby until they would meet with us. So they finally let us talk to them after most of the day.

We then had a few more meetings, and the company wanted to come visit our offices so they could make sure we were a 'real' company. At that time, we were only 5 guys. So we hired a bunch of our college friends to 'work' for us for the day so we could look larger than we actually were. It worked, and we got the contract."

I think the reason why PG respects Sam so much is he is charismatic, resourceful, and just overall seems like a genuine person.

Is this not a deliberate and material misrepresentation of your company? If this were a financial contract being sold, wouldn't this be fraudulent?

A comment from PG about him I will never ever forget even though I had never heard of Altman before goes like this: "You can leave Sam Altman on an island full of cannibals and when you come back a year later, he is the king of the cannibals."

This is one of the most awesome character traits to ever have. You WILL be successful by being like this, it's just a matter of time.

The canonical question is "Honey, does this dress make my ass look fat?" The honest answer may be "yes." But that answer could be hurtful and result in a seriously pissed off girlfriend/wife for a while.

The easy answer is "no." Dishonest, but no hurt feelings. A better response is often to deflect the question entirely and say, "I think you look much better in that purple dress you used to like."

That's what Sam did here: he deflected the question before it even arose.

In any case, you can't measure someone by one company. The formula for the success of a startup includes a random multiplier of roughly zero to a thousand. You can see this from how common it is for successful founders' second startups to fail.

I'm actually more impressed with Sam than when I wrote that. Since then I've talked to him a lot more because he is one of the alumni working part time as YC partners. He has extraordinary energy combined with the judgment of someone twice his age.

It's quite possible he's working on the "wrong" project. Many people have had this experience: Traf-O-Data (Bill Gates), Atari games (Steve Jobs), Tribe.net (Mark Pincus), and the list goes on endlessly.

If you had seen Bill Gates working on Traf-O-Data you might have said "that guy is going places" even though Traf-O-Data was ultimately not an important part of where he was going.

Most of us can see when other entrepreneurs are working on a project that doesn't reflect their core strengths. It's much more difficult to identify when we're the ones going down the wrong path.

Some of Steve's pet projects at Apple were miserable bombs. It's less a quest to find the right place than it is the fact that it's impossible to do more than guess at the reception that a product will have. You can boost the probabilities, but it's still a random process.

He took the fire from that failure and the knowledge of social networks and went all in on social games.

i was actually with him the night he was thinking of hooking up with the poker guys and i was like "who is going to play poker for fake chips... that's so dumb!"

... on top of that I didn't invest in Zynga and he invested in Mahalo! :-)

If that wasn't a win, I don't know what is...

Loopt isn't ever on my mind, neither anyone I know uses it - that sounds bad for a 6 or 7 year old, mass market YC company/product from one of YC's most prized and highest regarded/praised CEOs. So I think Sam might have picked the wrong battle. However, Sam's property that pg likes him for (relentless and tenacious) might be exactly what's preventing him from ditching the loop (no pun intended) and keeping him ditching the idea or jumping ship altogether. Even Sam’s tenacity can’t save a product people don’t care deeply for.

Or maybe I just give pg’s judgment of “people” too much credit by default, as an extension of his judgment of companies/products. Maybe pg sucks at picking winning people, but is great at strategy/tactics/products/ideas (just a hypothesis).

Either way, the takeaway for me here is be a bull dog - but don’t bark at walls, i.e. be tenacious, but find something worth being tenacious for.

"But the most successful founder we've funded so far, Sam Altman, was 19 at the time."

"I realized these tests existed after meeting Sam Altman, actually. I noticed that I felt like I was talking to someone much older."