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PODCAST

This Week in Startups

Jason Calacanis

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

technology

All Episodes

00:18:06

AI Copyright & Training Data w/ Chris Paniewski |...

This Week in Startups ·

2025/09/11

Jason sits down with Wilson Sonsini partner Chris Paniewski for a special Startup Legal Basics on one of the thorniest questions in tech right now: how copyright law applies to AI training data.Chris has worked on some of the biggest AI deals ever — including Scale AI’s $14B+ partnership with Meta and OpenAI’s $6.5B acquisition of Jony Ive’s design studio — and brings practical, on-the-ground insights from advising leading AI companies.In this episode, Jason and Chris cover:Why AI copyright law is

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00:57:12

Republic opens private markets as Positron takes on...

This Week in Startups ·

2025/09/10

Today’s show:In this founder-focused episode of This Week in Startups, we sit down with Republic’s Kendrick Nguyen to learn more about the company’s efforts to make the private markets accessible to the common investor. Best known for its work in equity crowdfunding, the Valor-backed startup now offers access to secondary shares, tokenized assets, and much more. Following, TWiST spoke with Positron CEO Mitesh Agrawal to learn more about his company’s inference-focused AI compute hardware. Related to

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01:17:15

How Founders Are Building the Next Great Startups |...

This Week in Startups ·

2025/09/09

Today’s show:In this TWiST founder triple-shot, Alex digs into the real-world rollout of AI agents: Paid.ai’s Manny Medina explains agent economics and value-based pricing, iTruckr’s Camilo Ramirez shows agents booking loads and coordinating drivers, and Tenax’s Elise Myrans demos computer vision + drones that score a single home’s wildfire/flood risk for smarter underwriting—plus live office-hours on winning enterprise pilots without getting stuck in PoC purgatory.Timestamps:(00:00) Brainstorming

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01:18:35

The Browser Wars heat up! PLUS, Khan on The Bulwark,...

This Week in Startups ·

2025/09/05

Today’s show:Jason heard Lina Khan on The Bulwark and got a little fired up.Plus Google doesn’t have to invest in Chrome… or basically do much of anything… Atlassian picked up not just any browser company but THE Browser Company… Follow-up thoughts on that MIT “companies aren’t using AI” study… AND Jason’s “two stock markets” theory. It’s a can’t-miss Friday TWiST.Timestamps:(00:00) Sony responds to Kpop Demon Hunters success… but Jason’s not buying it!(10:44) Sentry - New users get 3 months free of

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00:23:17

Creative Structures w/ Becki DeGraw | Wilson Sonsini...

This Week in Startups ·

2025/09/04

Today’s show:Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason. This time, they dive into the “have” companies — the breakout startups with multiple term sheets, competitive valuations, and unusual deal terms.From founder voting proxies to mandatory follow-on investment clauses, Becki breaks down the creative “off-menu” structures showing up in today’s financings, and what founders and investors need to watch for.Whether you’re a founder navigating investor FOMO or a VC

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01:14:44

Uber, Lucid & Nuro team up on robotaxis by 2026 | E2173

This Week in Startups ·

2025/09/03

Today’s show:Jason and Alex are joined by Nuro’s Dave Ferguson to unpack the Lucid–Uber–Nuro deal aiming to launch fully driverless Gravity SUVs on Uber by 2026. They dig into why off-the-shelf sensors and Nvidia’s Thor chip drive costs down, how mapping 150 cities improves safety, and why lidar still matters for night and edge cases. Plus: lessons from Cruise’s collapse, how regulators think about safety multiples, and why autonomy could finally make rides cheaper than owning a

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01:11:05

Jason’s Tesla Optimus prediction, Anthropic’s latest...

This Week in Startups ·

2025/09/03

Today’s show:Find out why it’s important to “get curious,” and more deep founder insights on a new TWiST.Jason and Alex are back with a look at Robot vs. Human violence spilling out into the streets, Elon Musk’s vision for humanoid robots, and a reconsideration of Apple’s open-source AI models. Is the hardware giant not getting enough credit for its smaller-scale innovations?Plus Grok has another hit model, AND a chat with Scale Social founder Runbin Dong about the importance of knowing your

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01:00:50

KPop Demon Hunters breaks records, Grok speeds up,...

This Week in Startups ·

2025/08/29

Today’s show:*“KPop Demon Hunters” is one of the year’s biggest smashes… AFTER Sony sold it off to Netflix for cheap! Hear about what went wrong with one of the year’s worst deals…PLUS Grok is counting on SPEED to help it outpace rivals… How Rep. Ritchie Torres (D-NY) ran into trouble on the podcast circuit… Nvidia’s big earnings report, and why everyone is watching that company in particular SO closely… PLUS a new Polymarket predicting the future of OpenAI!Timestamps:(0:00) How Sony missed out on

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00:26:07

Market Update and Trends w/ Becki DeGraw | Wilson...

This Week in Startups ·

2025/08/28

Today’s show:Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason to break down what’s happening in today’s startup market. From excess dry powder on the VC side to companies struggling to “grow into” their valuations, Becki shares what founders need to know about deal terms, pay-to-play provisions, and the shift from the 2021 heyday to today’s more structured environment.Why down rounds and structured deals are becoming more commonHow “pay-to-play” works (and why it’s

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01:29:40

Google is Nano Banana, Apple AI plans & The Great H1B...

This Week in Startups ·

2025/08/27

Today’s show:On a brand-new TWiST, Jason and Alex are asking why there are SO MANY note-taking AI apps?Plus another death has been linked to ChatGPT… is it too easy to get past chatbot guardrails? Why Donald Trump Jr. is joining Polymarket…. How the US Navy could catch up with its international rivals… AND should Apple just buy a big AI company to help them catch up?All that PLUS a visit from Colin Russ, whose viral H1B Visa thread might just inspire Jason to reach out to his good friend, Vice

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01:14:28

xAI’s App Store lawsuit, Intel shares vs. grocery...

This Week in Startups ·

2025/08/26

Today’s show:On an upbeat and optimistic new TWiST, Jason and Alex are debating why any new innovation or technology gets hit with a wave of bitter cynicism.PLUS Jason defends the government taking shares of Intel, explains the importance of interoperability, and predicts how AirBnB’s Joe Gebbia will upgrade the US government’s website design.All that PLUS thoughts on the Netskope IPO, Perplexity offering publishers actual revenue share, a deep dive on the new AI-based PAC, thoughts on open-source

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01:16:52

Do Kwon Guilty, Powell Pivot & OpenAI’s $12B Run Rate...

This Week in Startups ·

2025/08/22

Today’s show:Terra’s collapse, Powell’s pivot, and OpenAI’s explosive growth all collide in this TWiST deep dive.Do Kwon has pled guilty after Terra/Luna’s $60B implosion, Fed Chair Powell hints at a September rate cut, and OpenAI has officially crossed $1B in monthly revenue (on a $12B run rate). Jason and Alex unpack what this means for founders, LPs, and the next wave of AI + crypto.They also cover Canva’s $42B comeback, Anthropic’s doubled $10B fundraise, and the brewing battle between Figma

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00:59:15

Is Chalk.ai the ‘Next Databricks’? + Tollbit’s Bot...

This Week in Startups ·

2025/08/20

Today’s show:In this TWiST 500 double feature, Alex sits down with two breakout founders: Chalk’s Marc Freed-Finnegan & Tollbit’s Toshit Panigrahi!First, Chalk’s CEO Marc Freed-Finnegan is tackling one of AI’s biggest bottlenecks—data freshness. Instead of relying on stale batch jobs, Chalk delivers real-time pipelines for inference compute, automatically transpiling Python into C++/Rust so it can run blazing fast in production. Investors are calling it the ‘next Databricks’—and after hearing

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00:31:02

Scaling AI Photo Editing to 300M Users with...

This Week in Startups ·

2025/08/19

In this AI Basics episode, Jason sits down with Matt Rouif, Co-founder & CEO of Photoroom — the AI photo editing app with 300M+ downloads and 5B images processed annually.They break down:Why Photoroom built its own specialized AI modelsHow they grew from a scrappy startup to $50M+ in revenueLessons in product-led growth (from eBay sellers to DoorDash & Amazon)Red-teaming, brand safety, and building trust in AI imageryThe future of personalized ads, content, and designThis one is a

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00:38:01

Decart makes AI faster, Lume teaches lamps to fold...

This Week in Startups ·

2025/08/18

Today’s show:We’re back with two insightful new TWiST founder interviews.First up: Dean Leitersdorf of Decart tells us about squeezing maximum productivity out of your GPUs. But it’s not all talk: he also shows us the incredible open world model that can magically transform live footage.THEN! Jason and Alex chat with Syncere AI founder Aaron Tan about Lume, his robotic lamp device that went viral for folding laundry. Hear why Aaron thinks the future of robotics is not necessarily humanoid, and all

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00:57:10

Meta’s “Sensual” AI Doc LEAKS, Opendoor’s dreams...

This Week in Startups ·

2025/08/15

It’s a Friday TWiST and Jason and Alex are FIRED UP about this internal Meta doc laying out appropriate vs. inappropriate AI behavior… You won’t BELIEVE with what Zuck approves for 8-year-old users.PLUS… AI job displacement is HERE, at least in the Big Apple… Jason’s getting kind of paranoid about the surveillance state… AI remains frothier than ever through new Cohere and Cognition rounds… and why we’re dubious that Sam Altman REALLY plans to spend $1 trillion on OpenAI data centers.It’s all

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01:21:27

The End of the ZIRP Era, and why recruiting is SO...

This Week in Startups ·

2025/08/14

Today’s show:We’re back with another all-star VC roundtable discussion.Joining Jason are Dave McClure of Practical VC, NVNG’s Grady Buchanan, and Tomasz Tunguz of Theory VC. Together, they’re having a deep insider discussion of the state of venture, secondary markets, running funds of funds, the legacy of Lina Khan, the difficulty of recruiting, and why the pendulum has potentially swung in founders’ favor.Timestamps(0:00) INTRO, The origins of Practical VC and how secondary funds work.(05:44) So…

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01:16:27

GPT Psychosis is spreading, the NYT is Super-Doxxing...

This Week in Startups ·

2025/08/12

Today’s show:On an all-new Monday TWiST, Lon joins Jason and Alex to talk about a whole bunch of stories at the intersection of tech, business, and pop culture.First up, is GPT Psychosis real? And if so, what are the warning signs that your loved ones have been ONESHOTTED.Then, why did Jason get so upset at the NY Times piece about Mark Zuckerberg’s Palo Alto compound?PLUS we’re discussing Trump’s export fees on AMD and Nvidia, Jason’s pitch for why the president should work more closely with

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01:18:40

GPT-5 comes alive, Apple is struggling, and Ripple...

This Week in Startups ·

2025/08/08

Today’s show:Jason and Lon recorded a Thursday night special edition, so no Alex this time, but still lots to talk about.First up, Jason thinks it’s time for Tim Apple to exit the stage in lieu of a product obsessive innovator. Speaking of new products, GPT-5 is here and the hosts are… not exactly blown away. Are we in the midst of the AI trough of despair?PLUS we’re talking Ripple’s acquisition of Rail, Donald Trump’s new AI chatbot, Bumble’s new direction, Airbnb’s potential paths forward and MUCH

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01:13:06

Communist coffee hits NYC, RIP Hulu, GPT-5 arrives...

This Week in Startups ·

2025/08/07

Today’s show:It’s a brand-new PACKED episode of TWiST. Jason and Alex welcome guest Zach Dive of Adam.new, to tell us why he made a deepfake AI ad starring Jason and the All-In besties.PLUS a rundown of the biggest tech and startup news of the day, including Disney’s decision to sunset Hulu, OpenAI’s new open-weight models, the Cloudflare vs. Perplexity feud, Uber’s newly-announced stock buyback, China’s Luckin Coffee coming to Manhattan, and much much more!Timestamps:(0:00) Luckin Coffee hits NYC…

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1,222 results

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