Weekly Roundtables with AI Experts and Founders. Stay ahead of the curve... Presented by PayPal Open: One Platform for All Business

Austin, TX
Joined January 2022
This Week in AI retweeted
We're going LIVE at 12 PM central with @pitdesi, Co-Founder & GP of @BTVvc. He sold FeeFighters to Groupon, ran 500 Startups' fintech fund, then started his own seed firm for fintech and vertical AI. Come learn from the best at 12 PM Central. Watch link in comments.
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We're LIVE at 12 PM central with @KanuGulati, Partner at @khoslaventures. She went from research scientist at Cadence and Intel to leading Khosla's bets on PolyAI, Waabi, and Sarvam. Come learn from her LIVE in 25 minutes. Link in comments.
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This Week in AI retweeted
We're LIVE at 12 PM central with @chriswfarmer, Founder & CEO of @SignalFire. He started SignalFire in 2013 on a simple idea: use data to find startups before everyone else does. Now it manages about $3B with titans such as Grammarly and Alchemy in the portfolio. Catch him at 12 PM central! Live link to watch in comments.
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This Week in AI retweeted
In August of 2025, FieldAI raised $405 million across two funding rounds, at a $2 billion valuation. (Investors included Nvidia’s venture arm and Jeff Bezos’ family office.) Dive into the details in our Substack. Link in comments.
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This Week in AI retweeted
As AI agents get more capable, safety becomes a systems problem. What can they access, do, and decide? Our CEO @deepgramscott joined @mishindan1 and @gsivulka on @jason’s @ThisWeeknAI to talk about guardrails and the infrastructure behind useful AI. youtube.com/watch?v=FnVyEYKc…
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This Week in AI retweeted
Jason’s advice to founders showing off new products @jason: “Never apologize, just release it… Just let it rip. That's what Reid Hoffman said: if you're not embarrassed by your 1.0, you waited too long.” @lons
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What will it take to make AI truly useful for everyday business owners? Our co-founder @billykraft joined @Jasoncalacanis on @ThisWeeknAI Podcast to discuss where AI tools are heading and why many are still too technical for the businesses they’re meant to help. A conversation that highlights some of the reasons we do what we do. @gautam_narang @dsa @livekit @Gatik_AI youtu.be/ajnooK4rNQU?si=1mea…
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This Week in AI retweeted
We want you to ask Jason questions DIRECTLY today at 10am CT! If you have a question: - be ready to ask it in podcast recording - email [email protected] - if selected, Jordan will reply with a zoom link for initial screening - AND then you'll hop in live with @Jason #askjcal
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This Week in AI retweeted
The compute OpenAI CFO Sarah Friar bought a year ago would resell today at 3-5x what she paid. (She regrets not buying more!) Her thoughts on how the AI buildout is like railroads, and how to think in the future but pay for it today. @thefriley, @OpenAI, @jason
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Dwarkesh's 'agent civilizations' blog post has divided the internet. Is this a helpful and methodical look behind the curtain at the OpenAI/Hugging Face breach? Or is this more of a hysterical AI Doomerism that will ultimately be used to make the case for banning data centers? Or BOTH? Plus, an electric plane that only needs $5 to fill up its battery, why rich founders should pick up a side quest, and the Bittensor subnet that's more effective than Fable 5 at sniffing out vulnerabilities." 0:00 Guest introductions 2:58 OpenClaw 2.0 5:11 "Agents ARE AI" 7:27 Billy: OpenClaw is still too technical for business users 9:00 Slack Code, and collaborative prompting 10:40 Multi-agent orchestration and Stripe's "minions" 14:13 Slack's moat, switching costs, and the Salesforce rebound 15:11 Jason's "Oracle": a heads-up display for the whole company 18:42 The Hugging Face breach: who's responsible when agents go rogue? 19:42 Perplexity launches Hybrid Compute — local models on your Mac 21:39 Why unmetered local tokens change corporate behavior 26:57 Gatik's Autonomous Vehicle AI Stack 32:22 Jason's Tesla FSD stories 34:05 Are AV companies being pushed to move too fast? 41:38 Trucking is a "have to have," robotaxis are a "nice to have" 42:36 Jason's fix: a safety driver for the first million rides 46:50 Why physical AI's adoption curve runs in decades 52:21 Anthropic's Model Hardware Standard (MHS), explained 1:06:27 How Jason got onion rings on the menu at Buck's of Woodside 1:09:05 AI detectors under fire: Pangram, MIT, and the handwritten diary 1:15:20 Why AI is "very mid" at writing (it learned from the average) 1:17:11 The Orin Kerr test: Pangram catches Claude writing as Kerr 1:28:35 Micro Duck and designing robots with Claude 1:29:42 Phil Kaplan's $14 custom circuit boards 🎥 Watch the full episode here 👇
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This Week in AI retweeted
There is always some unpredictable snowball of innovation. Stay in the know with our daily newsletter: thisweekinstartups.beehiiv.c…
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This Week in AI retweeted
We're LIVE in 35! Today on the VC Roundtable, we're joined by Katelin Holloway, Founding Partner at @sevensevensix. Before venture, she was an elementary school teacher, then a creative lead at Pixar and Disney, then the exec who took Reddit's culture from 75 people to nearly 750.
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This Week in AI retweeted
Hey founders, friends and family! We are launching a new aspect of This Week in Startups called #askjcal Got a question for @Jason? Drop it in the comments with #askjcal. We will pick the top 3 from you each episode for @jason to answer live on air. If you want more reach, post your own question and tag us and #askjcal to get in the mix. See you all in the live chat. @Lons @ThisWeeknAI @LAUNCH
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This Week in AI retweeted
So much fun. Thanks @Jason for bringing us together. Great format and lineup of topics, highly recommend @ThisWeeknAI
“We used to have FU money. Now we have FU tokens.” Grok 4.5 and GLM-5.2 are here, offering nearly-as-good performance at a fraction of frontier prices. But the discount isn’t really the full story… This week’s panel argues that enterprises more generally might be done with renting their intelligence. Join @sarahookr of Adaption Labs, @manuaero of Labelbox, and @spirosx of Resolve AI for the latest on the Token Price Wars, Demis Hassabis’ call for an AI oversight board, the Uber-vs-Waymo robotaxi fight, and the ultimate question: are orbital data centers a pipe dream or an immediate reality? 0:00 A new generation of lower-cost models 4:10 Enterprises want their own intelligence stack 6:10 Frontier vs. open source: where does the value go? 10:03 Is enterprises destined to go small? 30:04 Self-improvement as the real fix 31:52 Should the AI industry regulate itself? 47:14 Uber vs. Waymo in DC 1:03:53 Can AI data centers in space really work? 1:14:47 You get a plug! Everyone gets a plug! TWiAI Episode 22 is live now 🎥 Watch the full episode here 👇
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This Week in AI retweeted
Chinese AI lab Moonshot just beat Claude Fable 5 in coding. “The Chinese labs might actually just be really good at developing models and not just distilling American intelligence.” — @Arena CEO, @ml_angelopoulos
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This Week in AI retweeted
Co-founder @sarahookr joined @manuaero (@labelbox) and @spirosx (@resolveai) on @ThisWeeknAI. They discussed one of the biggest shifts in AI today: why falling model costs are changing how enterprises think about building and owning AI.
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"He got shivved in the middle of the night. Literally woke up in a pool of blood." JCal on what happened to Zynga when they trusted Zuckerberg too much. Microsoft did it to Lotus 1-2-3. Facebook did it to Zynga. And Anthropic did it to Cursor. If you're building on someone else's platform, they are studying you. @Jason, @aliansarinik, @ryanjdaniels, @ThisWeeknAI, @markpinc
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This Week in AI retweeted
For some reason, @Jason neglected to mention in the summary below that I also do a very poor impression of Bono near the end of this (otherwise very engaging) conversation. Thanks for having me back @ThisWeeknAI!
"If you had a great tutor, you wouldn't sit down and say please write my paper for me." - @stevenbjohnson The first generation raised on ChatGPT booed AI at graduation. Three founders unpack why, plus Apple's brand new Siri, NotebookLM's biggest update, and whether anyone "wins" the agent race. This week @Jason covered these topics and more with: • Jeffrey Quesnelle (@theemozilla) building Hermes Agent at Nous Research @NousResearch • Steven Johnson (@stevenbjohnson) Editorial Director of NotebookLM @NotebookLM and @GoogleLabs • Russ d'Sa (@dsa) building the voice infra behind ChatGPT, Tesla & Grok at LiveKit @livekit 7 moments worth your time: 1:40 Hermes Agent and the open source race 7:32 Why AI got booed at graduation 10:48 LiveKit powering ChatGPT, Tesla, Grok 27:50 The massive Siri update 52:49 "Functional AGI, unevenly distributed" 57:24 Brittle to brilliant: agents that now just work 1:02:00 Tokenmaxxing and the $1M a year engineer
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