Disclosure certainty 4/5 debate potential 1/5

Altman: Passing on follow-on rounds over price is his biggest investing error

Sam Altman · Uncut Interview with Sam Altman on Masters of Scale [Audio] · Y Combinator · Feb 23, 2018 · at 55:41

In an interview with Reid Hoffman, Y Combinator president Sam Altman reflects on investing failure modes and what he considers his greatest career embarrassments.

0:00 / 0:25exact quote · 25.7s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“The painful one is the other kind of error where you're like, you know, this company's gonna suck, and then it goes on to be really successful. And the most painful version of that of all for me is when I'm already an investor in the company, they ask me to put more money to a future round, and I say the price is too high, and I'm not gonna do it, and that has happened, you know, many, many times, but that, that is, those are the most embarrassing errors to me.”

quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →

More from Sam Altman

Prediction Not checkable as stated
Altman: Startups founded today will produce future trillionaires
“I bet there's some future trillionaires sitting in this room, and I would bet that the startups created today will be much more valuable, much more impactful than startups of the past”
Sam Altman Jul 28, 2026 ▶ 8:47 Sam Altman: "Never a Better Time to Do a Startup" · Y Combinator
Disclosure
Altman: OpenAI made big mistakes in Hugging Face incident, an alignment failure
“Here are the mistakes that OpenAI made, and we did make some big ones, of course, but these systems have gotten incredibly capable. So I think it's an alignment failure. I think it's a security failure. I think it's like a very serious thing, even though it's,…”
Sam Altman Jul 28, 2026 ▶ 25:32 Sam Altman: "Never a Better Time to Do a Startup" · Y Combinator
Prediction Not checkable as stated
Altman predicts humanity will achieve unimaginable superintelligence within 20 years
“Look, there, there's a lot you know, in 10 or 20 years, unless something goes hugely wrong, we'll have, like, unimaginable super intelligence, and I'm very excited to see how that goes.”
Sam Altman Jun 21, 2025 ▶ 33:07 Sam Altman: The Future of OpenAI, ChatGPT's Origins, and Building AI Hardware · Y Combinator
Prediction Not checkable as stated
Altman: AI progress could compound over next nine years toward superintelligence
“I can see a path where the work we are doing just keeps compounding, and the rate of progress we've made Over the last three years, continuous for the next three, or six, or nine, or whatever. You know, nine years would be, like, 3500 days, or whatever. If we …”
Sam Altman Nov 8, 2024 ▶ 2:09 How To Build The Future: Sam Altman · Y Combinator
Opinion
Altman: Building AGI at OpenAI outweighs all past human innovation combined
“If this one thing works, like, if we do actually build AGI at OpenAI, that is more important than all of the innovation sum total in humanity so far. So, clearly not has all the innovation happened.”
Sam Altman Nov 8, 2018 ▶ 22:13 Sam Altman on Choosing Projects, Creating Value, and Finding Purpose · Y Combinator
Opinion
Altman: Overreacting to AI safety risks creating a zero-agency surveillance dystopia
“One dystopia that I'm particularly nervous about 10 years from now is we overreact to AI safety, and so we say, look, everyone, you're gonna get a cure for cancer, you're gonna have material abundance, but you will have no freedom, you will have no agency, it …”
Sam Altman Jul 28, 2026 ▶ 36:58 Sam Altman: "Never a Better Time to Do a Startup" · Y Combinator
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 300 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.