I’m Binge Watching Interviews with Sam Altman…

…so you don’t have to… and here are my takeaways. (Article 1)

Drew Wolin
4 min readMar 21, 2023

Who is Sam Altman?

What do you live under a rock?

Kidding! Kidding. In fact, if you legitimately do not know the answer yet, even better. Allow me to introduce Silicon Valley Wiz Kid…

I don’t have the rights to this picture, but I hope “they” will go easy on me as a new Medium contributor, maybe?

Sam is the former president of Silicon Valley based startup accelerator Y Combinator. He is the current CEO of OpenAI.

OpenAI makes ChatGPT.

Article Series Format

This will be a series of 15–20 articles, all of which summarize (plus more) interviews with Sam. In each article, I will cite the interview(s) I watched, write specific quotes / context from the interviews, and may share thoughts, notes, or anecdotes that come to mind.

At the end of this article series, I will post a summary, spanning content and thoughts across all articles in the series.

Unless otherwise stated, all quotes are from Sam Altman.

Here we go!

2018-Y Combinator Interview

“OpenAI is going really well.”

Context: Note that this interview is from 2018.

“In my downtime, I think about: Do I feel like I am being maximally useful?”

“December 31st every year, I take a break, and I sit and write what went well last year, what didn’t. I look at my to do list for the year, and I write out what I’m going to do next year. Because I know that I’m going to do that every year, I stress about it less the other 364 days.”

“Pursue a lot of things as quickly and cheaply as possible. And then be very honest with yourself about what is working well and what is not. And the hard part is cut all of the stuff that’s not working, and focus on the stuff that is working.”

Sam took a year off — which he says is really hard to do, especially in Silicon Valley, because your job determines your social status.

He highly recommends it. “It is one of the two or three best career things I ever did. I read different text books, I learned different topics I’d always been interested in.” He also traveled, he made investments and learned Finance.

“The things that have taught me a lot about business are: Poker and angel investing. I recommend both of those.”

There are certain people who Sam just believes are going to do amazing things and so he follows their careers. He finds that consistently the thing that they need the most help on are: They they are thinking too small, and that they are thinking about risk the wrong way (adding that they need a perspective shift).

Recommends surrounding yourself with people who will make you more ambitious.

Adds that 98% of people will try to pull you back. Almost everyone wants you to be average.

Recommends reading poker books (second time mentioning poker) and reading biographies of people who have done amazing things.

“You’re never able to get away from the things you’ve written.”

Context: (Somewhat jokingly responding to the interviewer sharing a quote from a passage that Sam wrote years ago).

As my first contribution to Medium, this seemed timely. Thank you Sam, for the warning!

Observes that lots of CEOs have support groups to hold each other accountable.

“I don’t believe in the deferred life plan… One of the problems with the deferred life plan is that everybody can tell that that’s what you’re on. I’ve seen it fail a lot… Think about what you want to do, and do it…. People can sense authenticity. People can sense peoples’ motivation. To succeed in anything, it’s important that people are rooting for you.”

Gives example of people investing in Bitcoin to try and get rich, telling themselves the story that once they have enough money, they’ll pursue what they really want to do, but never do.

My Biggest Takeaway from this Interview

Just do what you want to do (what you care about), even (especially) professionally. Take a year off (which I’ve wanted to do anyway, as noted in the article I currently have in my drafts “10 Years in the Workforce, a Reflection.”)

More to come!

I’m Drew. I’m not new to writing, but I am new around here.

Medium family, thank you for welcoming me.

Articles in Series:

  1. ← You are here.
  2. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-559bea849356
  3. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-44638f1e4eff
  4. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-e1d8ac81ca43
  5. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-588981e6eb2b
  6. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-5ebfe3c79f7e (Lex Fridman Interview :00 to :30)
  7. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-710bc1447a7c (Lex Fridman Interview :30 to :60)
  8. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-cb504390ab8c (Lex Fridman Interview 1:00 to 1:30)
  9. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-68a4fb2b5785 (Lex Fridman Interview 1:30 to 2:00)
  10. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-12b0bad4222e (Lex Fridman Interview 2:00 to end)
  11. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-3b9bb7b36bbc
  12. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-7981fdb0c879
  13. https://medium.com/@dwolin/im-binge-watching-interviews-with-sam-altman-29fe9ec5f614

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Drew Wolin

Scout and Analyst, NBADraft.net | Freelance Basketball Writer | Full Time Data and Business Analyst