Disclosure certainty 5/5 debate potential 2/5

Calacanis invested $500K for 10 percent in a ChatGPT wrapper startup

Jason Calacanis · E118: AI FOMO frenzy, macro update, Fox vs Dominion, US vs China & more with Brad Gerstner · Mar 3, 2023 · at 23:26

Jason Calacanis, technology angel investor and host of All-In, discloses an investment deal made with a returning founder building on top of ChatGPT.

0:00 / 0:18exact quote · 18.6s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“Serial founder and team that we've backed for that had an exit said, can I show you something? I said, yeah, got on the zoom, showed me a little proof of concept using chat GPT. And he said, this is my idea. This is the vertical. And I just said, okay, what do you want? He said, 500 K for 10%. I said, okay, done.”

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 Jason Calacanis

Prediction Not checkable as stated
Calacanis predicts OpenAI will lose its lead and become fourth-ranked AI player
“My most contrarian belief was OpenAI loses its lead, loses its nonprofit to for-profit transition and becomes the number four player in AI. The total collapse of OpenAI is my most contrarian prediction for .”
Jason Calacanis Jan 4, 2025 ▶ 1:11:34 2025 Predictions: Tech, Business, Media, Politics!
Prediction Held up
Calacanis: Nvidia will decline or severely downgrade investment in OpenAI
“I think NVIDIA is not going to take their option to invest in open AI, or they're going to really downgrade at 70, 80%, and they're going to allocate it to other players.”
Jason Calacanis Dec 6, 2025 ▶ 18:35 OpenAI's Code Red, Sacks vs New York Times, New Poverty Line?
Opinion
Calacanis: Mark Zuckerberg is the greatest censor in human history
“His action was to be the greatest censor in the history of humanity. There's no human being who censored more humans than him.”
Jason Calacanis Jan 11, 2025 ▶ 1:08:44 LA's Wildfire Disaster, Zuck Flips on Free Speech, Why Trump Wants Greenland
Prediction Didn’t hold up
Calacanis: Democrats will replace Joe Biden with Gavin Newsom after first debate
“This is why I think Biden's getting hot swapped this month. You heard it here first. He's got, no, Gavin is going to be running for president. It's going to be Trump and Gavin. They are hot-swapping Biden after this first debate. Biden is going to get demolish…”
Jason Calacanis Jun 7, 2024 ▶ 28:25 DOJ targets Nvidia, Meme stock comeback, Trump fundraiser in SF, Apple/OpenAI, Texas stock market
Prediction Not checkable as stated
Calacanis: Trump will attempt to overturn the government again if given the chance
“Guy has no morality, and he would have overturned the government if he had the chance. And he will do it again.”
Jason Calacanis Aug 4, 2023 ▶ 1:18:57 E140: LK-99, Sclerotic establishments, Fitch downgrades US debt, Trump indicted... again
Opinion
Calacanis: FTC Chair Lina Khan is punishing tech for being successful
“I think she is absolutely doing Biden's bidding. With an anti-tech, anti-wealth creation, anti-capitalism, frankly, pro-union punishment. I think this is punishment for tech being too successful.”
Jason Calacanis Jul 14, 2023 ▶ 48:05 E137: Inflation cools, market rips, Ripple/MSFT beat regulators, NATO summit, cocktails of youth
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 460 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.