1.

Sam Altman's career fascinates me. He went from a teen founder failing to get traction, to President of Y Combinator, to founder of OpenAI. Those seem like big, random jumps. It's easy to think Altman's career has been littered with luck.

Sure, luck played a part -- as it always does -- but the deeper you dig the clearer it becomes that luck was nothing more than a footnote in his story. Altman navigated those big, random jumps flawlessly and now finds himself at the helm of the most exciting company in the world. How did he get that good?

2.

Altman's first startup was Loopt, a location-based social networking app. The company was founded in 2005 and was initially funded by Y Combinator. In 2012, it was acquired for $43 million. Loopt had more than five million users but is alleged to have struggled to gain traction. It was a passive location-tracking app -- once you turned it on, it continued to tell your friends where you were.

At that time, those apps were the new darlings of tech. It became only the latest location app to be acquired and see its own product shut down, following others like Gowalla and Yobongo.

In 2014, Altman became the President of YC. Becoming President of YC after going through the program is like becoming Dean of Harvard after being a student.

Altman was the second-ever President and was hand-picked by Paul Graham. Why? Because he really, really impressed Paul Graham. Graham wrote an essay in 2009 listing Altman alongside Steve Jobs and Larry/Sergey as the 5 most interesting startup founders of the last 30 years.

Graham notes (emphasis mine):

"I was told I shouldn't mention founders of YC-funded companies in this list. But Sam Altman can't be stopped by such flimsy rules. If he wants to be on this list, he's going to be... there are a few people with such force of will that they're going to get whatever they want." Honestly, Sam is, along with Steve Jobs, the founder I refer to most when I'm advising startups. On questions of design, I ask "What would Steve do?" but on questions of strategy or ambition I ask "What would Sama do?"

That's not just impressing someone. That's knocking their socks off. How did he do it?

3.

Altman exudes extreme belief and ambition in everything he does. He shows ridiculous conviction in his decisions and I suspect that combination of belief and conviction create the "force of will" that Paul Graham uses to describe him.

I've studied Steve Jobs deeply and Altman shares this trait with him. Jobs was famous for what observers called his "reality distortion field." Part motivational tactic, part drive and ambition, he was notoriously dismissive of phrases like "It can't be done" or "We need more time."

Jobs learned early in life that reality was falsely framed by rules and compromises that people had been taught as children. He had a much more aggressive idea of what was or wasn't possible. To him, when you factored in vision and work ethic, much of life was malleable.

Altman sees life through the same lens:

"A big secret is that you can bend the world to your will a surprising percentage of the time -- most people don't even try, and just accept that things are the way that they are." -- Sam Altman

4.

Brian Chesky, founder of AirBnB, tells a story about Altman that showcases this trait. Chesky shared that when they entered YC, they had doubts about their survival, but their ambition grew as they progressed in the program. That growth was largely due to their interaction with Altman, who was then an unpaid mentor and fundraising expert at YC.

When the Airbnb team presented Altman with a slide deck for a $500,000 seed funding round, Altman encouraged them to increase their projected revenue from $30 million to $3 billion. Altman said, "Take all the M's and make them B's. Either you don't believe everything you said in the rest of the deck, or you're ashamed, or I can't do math."

Altman displayed this willingness to think big throughout his tenure at YC, growing the organisation rapidly during his time there. Similarly, his vision for OpenAI is marked by audacity and a willingness to embrace the unknown.

When asked about the company's revenue model in 2019, Altman candidly admitted that they had no plans or ideas for generating revenue, and instead stated that their goal is to build a generally intelligent system that can figure out how to generate returns for investors. This statement may seem outlandish to some -- it drew a lot of laughter from the crowd -- but it's a testament to Altman's unwavering confidence in his ability to achieve the impossible.