I’m Binge Watching Interviews with Sam Altman…

…so you don’t have to… and here are my takeaways. (Article 4)

Drew Wolin

6 min readMar 23, 2023

This is a continuation from a series of articles found HERE.

2016-Sam Interviews Elon Musk for Y Combinator

Context: Sam became President of OpenAI mid-2019.

Sam and Elon Musk are both co-founders of OpenAI (founded in December 2015).

Remember, this series is about Sam. I still thought it interesting to pull in media where Sam is the interviewer.

Editor’s Note, Observation: Sam’s voice cracks at the start of the interview. He seems nervous, or uncomfortable, around Elon. I can’t assign a reason. Perhaps it’s out of a great deal of respect. I can’t say.

Editor’s Note, Observation: Sam opens up later in the interview, cracking a number of jokes with Elon. Elon responds well, they seem to have playful chemistry.

My Biggest Takeaway from this Interview

My takeaway is simple: I find it interesting to see how Sam interacts with Elon. I noted above how I read the interaction.

2015-Sam Talks at the Platzi Conference in Mexico City about Start Ups

Context: Note the date of the interview.

This is the longest-ago interview in my article series so far. Sam dishes general advice on building a start up, and some advice specific to non-American start ups.

Sam says that as a start up, you can build something a lot of users like, or something a small number of people love.

“All successful start ups we’ve funded have started with something that a small number of users love, and expanded from there.”

“You need users that would be really, really disappointed if your product went away.”

On companies that grew big, like Google: “You probably heard about it (Google) from a friend. And then you told another friend about it. This is the best long term growth strategy.”

“You want to build a start up where if you win, then you are going to stay the winner.” Sam added that it’s so hard to win in the first place that once you do, you need to have a reasonable path to staying the leader.

Editor’s Note: Sam even suggests seeking a “monopoly,” an idea popular with Peter Thiel. Thiel and Sam have some relationship, including Sam inviting Thiel as a guest speaker to a class he was teaching at Stanford.

Why, if you win, will you stay the winner?

Sam says all start ups have problems, and that a lot of founders give up on their start ups because they feel that it’s unusual that things are broken. Unfortunately, things are always going to be screwed up. And if you are successful, you will continuously deal with problems, he says.

“All start ups are deeply broken on the inside.”

“Team (interpersonal) problems are the biggest killers of start ups within Y Combinator.”

“Start ups kill themselves much more often than start ups get killed by someone else.”

As your company gets bigger and bigger, the only thing the CEO gets to decide on is the company strategy, and who the players are. So you need to hire incredibly well.

“(The CEO) needs to spend like 1/3 of time on hiring people.”

“If you make a mistake hiring, you need to fix it incredibly quickly.” Sam says most founders don’t understand this or won’t do it because it’s painful.

Sam says the most impressive thing about Mark Zuckerberg is not that he hires well, but that he fires well.

Sam says the best start ups have a culture of extreme frugality, adding: “If a start up is profitable, then the start up is under its own control. But if a start up is not profitable, it is under complete control by investors.”

Sam says that focus and intensity are what lead to a successful start up (in addition to what was previously mentioned).

“With the bad start ups, they are talking about all these different plans, and making progress on none of them. The best start ups are incredibly focused on the 1–2 things that matter right now.”

Sam gives an example that within one week, the start up will have pursued its 1–2 focus areas, and they also have figured out all of these new things to do as a result.

“If every iteration is 4 hours, it compounds very fast. If every iteration is two weeks, it compounds much slower.”

“Successful start ups are focused on a tiny number of things, but do those things very intensely. Looking at week over week progress… The focused and intense ones dominate the others.”

“Most people aren’t sure how to have a good idea.”

“The only thing that you can’t do is create a market that doesn’t want to exist.” Everything else (about an idea) can be changed.

“The very best start up ideas sound bad but are good.”

Editor’s Note: This sounds odd to me as general advice. But he does say, the things that seem obvious to do, the big companies already do. He gives AirBnB as an example: Nobody wants to stay on each other’s couches!

“I’m always skeptical if I hear a start up that sounds like an obvious idea. Because it means that a lot of people are going to do that. And the competition is going to be brutal.”

“The founders that we have funded that have been most successful are working on ideas that they themselves understand very well.”

“Ignore people telling you your idea is bad. They may be right. But the only way to know is to build it out.”

Sam says that in Silicon Valley, the default response to any idea is to be excited, and think about why that might work. The default response in the rest of the world is focused on why it won’t work. The good ideas are so fragile and so killable that you need to be careful to insulate yourself.

For this reason, YC doesn’t have coworking space. Companies work in silos. Because they are building out ideas that sound bad.

This speech is in Mexico City. Sam shares an observation: “The world today is really connected… Yet what a lot of start ups outside the United States do is say that they are going to be the Uber is Latin America. We’re going to take an idea that is working in the US, and do it better in our local market… What would be better to do is to say, ‘The fundamental idea of Uber is that people need to be able to move easily… Rather than build the Uber for Mexico City, I am the expert in this market. I am not going to build the Uber for Mexico City. I am going to build this new thing that accomplishes the same need.’ And who knows, if you do that, you may find something that takes over the entire world… Just build something better than what worked in the US.”

Sam ends by soliciting applications to YC!

My Biggest Takeaway from this Interview

Wow. So many. This was my favorite interview in the series so far. I loved most parts of it, but especially the part focusing on how good start up ideas sound like bad ideas. And you need to build them anyway.

Working at YC, Sam has seen a lot of what makes a good company. OpenAI was not yet founded when this talk was given.

More to come!

I’m Binge Watching Interviews with Sam Altman…

…so you don’t have to… and here are my takeaways. (Article 4)

2016-Sam Interviews Elon Musk for Y Combinator

My Biggest Takeaway from this Interview

2015-Sam Talks at the Platzi Conference in Mexico City about Start Ups

My Biggest Takeaway from this Interview

Articles in Series:

Written by Drew Wolin