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 competing to get on the best cap tables, this conversation will give you insight into the new rules of the game.

*

Timestamps:

(0:00) Jason welcomes Becki back to Startup Legal Basics

(0:32) The “haves” vs. “have-nots” in today’s startup market

(1:28) Creative legal structures: the “off-menu” items

(4:19) Travis’ Uber favor & modern founder asks

(7:05) Rise of secondaries & unusual board structures

(11:22) Mandatory follow-on investment clauses in seed rounds?

(14:13) Crypto’s resurgence and legal implications

(15:55) The decline of proper diligence in hot deals

*

Check Out Wilson Sonsini: https://www.wsgr.com

Check out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics

*

Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/

*

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

*

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Substack: https://twistartups.substack.com

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 car.

Timestamps:

(00:00) Show intro…

(06:23) Uber x Lucid x Nuro: why this 2026 robotaxi deal matters

(09:57) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(11:13) What the self-driving “cost stack” really looks like in 2025

(14:08) Road-mapping at scale: Nuro’s 150-city data collection push

(15:38) Can AVs handle snow & rain? Weather rollout and Uber Black positioning

(20:05) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!

(21:07) Show Continues…

(24:24) Probabilistic vs. deterministic driving models — and the DARPA roots

(30:08) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.

(31:08) Show Continues…

(35:38) Post-Cruise reality check: transparency, regulators & trust

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Thank you to our partners:

(09:57) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(20:05) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!

(30:08) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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 worth.

Timestamps:

(0:00) Robot vs. Human violence in the streets! Is anti-clanker behavior inevitable?

(05:13) Producer Claude’s company Anthropic is growing FAST, raising BIG money

(09:21) More on why Jason is convinced Tesla’s Optimus robots are the future

(10:35) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST

(11:50) Show Continues…

(20:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(21:19) Show Continues…

(23:31) Ask Jason: Should you get a ticket for messing with an autonomous vehicle?

(27:04) Is Apple not getting enough credit for its open-source AI models?

(30:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits

(31:55) Show Continues…

(38:08) Grok has another hit AI model… how can anyone even keep track of this?!

(40:27) Runbin Dong of Scale Social stops by from ICELAND

(42:54) How Runbin’s job delivering homemade dumplings inspired his startup

(47:05) Why founders need to know their WORTH when pricing their products

(59:21) Jason’s advice for companies that are creating their own category

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Thank you to our partners:

(10:35) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST

(20:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(30:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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 “Kpop Demon Hunters”

(10:15) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

(11:20) Show continues…

(13:59) Why some politicians struggle so much on podcasts

(19:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits

(20:53) Show continues…

(30:24) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist

(31:37) Grok is relying on SPEED to outpace rivals… and it’s working

(41:23) Are AI companies playing a mega-budget game of chicken?

(42:31) Why everyone’s watching Nvidia’s earnings so closely

(47:50) Jason says he’ll NEVER go back to a non-AI browser

(53:32) Polymarket: Is OpenAI going to release their own browser?

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

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Follow Lon:

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Thank you to our partners:

(10:15) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

(19:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits

(30:24) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist

Ready to level up your AI collaborations?

Head to www.claude.ai/twist

• You can’t do everything we’re doing without a paid plan…
• But TWiST listeners get 50% off their first three months of Claude Pro.
• Just go to Claude dot AI Slash TWiST to get started.

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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 common
• How “pay-to-play” works (and why it’s showing up so often now)
• The psychology of VCs vs. founders during tough fundraises
• What the M&A landscape really looks like in 2025
• Legal provisions investors are using to protect themselves in today’s talent wars

Whether you’re a founder preparing for your next round or an investor navigating tougher terms, this conversation will help you understand the new realities of startup fundraising.

*

Timestamps:

(0:00) Becki DeGraw joins Jason for Startup Legal Basics

(1:12) The “perfect storm” shaping today’s startup market

(4:30) Companies struggling to grow into 2021 valuations

(6:31) Why down rounds and structured deals are rising

(8:59) Pay-to-play explained: what happens if investors don’t participate

(15:43) The mid-market M&A wave vs. big tech acquisitions

(20:37) Talent wars, acqui-hires, and protective legal provisions

*

Check Out Wilson Sonsini: https://www.wsgr.com

Check out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics

*

Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/

*

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

*

Follow TWiST:

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Substack: https://twistartups.substack.com

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 President JD Vance. Check out the full episode!

Timestamps:

(0:00) Intro, Jason’s checking out Notion’s new AI note taking app… is it time to cancel Granola?

(06:57) How Google Gemini’s new 2.5 Flash Image tool (formerly known as “nano-banana”) could change advertising

(10:28) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(11:40) Show Continues…

(17:50) Another death linked to ChatGPT… is it too easy to get around AI chatbot guardrails?

(19:26) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

(20:34) Show Continues…

(28:10) Donald Trump Jr. invests in Polymarket and joins the board…

(29:45) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!

(30:49) Show Continues…

(33:30) How Jason thinks the US Navy could catch up with China and other rivals, with help from startups

(40:01) Do Jason and Alex think Apple might REALLY buy a big, expensive AI company? Would that be admitting defeat?

(45:57) Colin Russ (@ThaaatColin) tells us about his viral X thread and why he’s worried about H1B visa fraud

(55:32) Jason’s solution for the H1B system, and a message for VP Vance.

(01:08:25) Jason responds to Kara Swisher, who accused him sucking up to power

(01:19:07) Jason responds to his old pal Sam Harris, who thinks he’s loyal to the wrong people

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

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Follow Lon:

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X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(10:28) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(19:26) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

(29:45) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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 LLMs, and much much much more.

Timestamps:

(0:00) Cynicism vs. Optimism and why Jason thinks cynics go after any interesting new technology

(10:02) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(11:04) Show Continues…

(14:37) Why Jason supports the Intel deal but worries it will become a trend

(20:46) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.

(22:00) Show Continues…

(27:02) Is it hypocritical to oppose socialist grocery stores but support the Intel deal? Jason says NO.

(29:41) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(30:58) What does xAI hope to get out of this OpenAI/Apple lawsuit? Jason and Alex theorize…

(39:12) Why Jason thinks interoperability is so important and how App Stores OUGHT to work

(41:12) How AirBnB’s Joe Gebbia could potentially upgrade the US government’s websites

(49:27) What does Netskope do exactly? SASE?! Producer Claude explains…

(58:32) Alex and Jason celebrate Perplexity rev sharing with publishers

(01:10:02) Jason’s thoughts on the Leading the Future PAC, and US AI policy

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

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Follow Lon:

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Thank you to our partners:

(10:02) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(20:46) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.

(29:41) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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 & Canva.

Plus: Uber, Nuro & Lucid’s $6B robotaxi push — and why drivers are already protesting in Wuhan & Boston.

#Startups #Crypto #AI #VentureCapital #OpenAI #Anthropic #Canva #Figma #ThisWeekInStartups

Timestamps:

(0:00) INTRO

(01:15) Fed rate cut signals & market reaction

(05:36) Jason’s $400K in new fund bets

(10:25) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(11:30) Show Continues…

(16:22) Do Kwon & the Terra/Luna collapse

(20:22) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.

(21:23) Show Continues…

(29:43) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist

(30:55) Show Continues…

(36:14) OpenAI’s $1B/month revenue run rate

(42:13) Anthropic’s $10B round & AI market sizing

(51:31) Canva’s $42B valuation & Figma comparison

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

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Follow Lon:

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LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(10:25) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(20:22) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.

(29:43) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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 this convo, you’ll see why.

Then, Tollbit’s CEO Toshit Panigrahi returns after raising a $24M Series A and signing up 1,400+ publishers. With RAG traffic exploding and robots.txt losing its teeth, their ‘bot paywall’ could reshape how AI agents pay for the content they consume. Are we heading for a Spotify moment for data licensing?

A must-watch if you care about the economics of AI, from data pipelines to publisher monetization.

Timestamps:

(0:00) Intro + sponsors

(1:03) Alex tees up two Twist 500 interviews: Chalk & Tolbert

(2:47) Why AI is shifting from training compute to inference compute

(4:41) Data freshness & real-time inference explained

(10:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(12:00) How Chalk transpiles Python into C++/Rust for speed

(18:52) Chalk’s business model, margins & $500M valuation

(20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(21:24) Show Continues…

(28:02) Tollbit returns: $24M Series A & the rise of RAG bot traffic

(30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

(31:41) Show Continues…

(36:53) Robots.txt losing relevance & the case for bot paywalls

(39:19)Publishers, AI agents & the future economics of the web

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.twist500.com

Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

Follow Lon:

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LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

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X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(10:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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 models
• How they grew from a scrappy startup to $50M+ in revenue
• Lessons in product-led growth (from eBay sellers to DoorDash & Amazon)
• Red-teaming, brand safety, and building trust in AI imagery
• The future of personalized ads, content, and design
• 
  

This one is a masterclass for founders, operators, and builders.

Timestamps:

(0:00) Matt Rouif joins Jason to discuss AI Basics.

(0:45) Meet Matt Rouif: Photoroom’s $50M+ AI photo startup

(3:15) Live demo: background removal + virtual try-on

(7:40) From indie sellers to DoorDash & Amazon

(12:20) The “Barbie Movie” API moment

(17:05) Red-teaming AI: trust, safety & brand protection

(22:10) Running a 100-person AI startup

(26:30) The future of personalized ads (put you in the ad?)

Explore Further:

Google Cloud’s Report: The Future of AI

Get insights from 23 leading experts on how startups can leverage AI for real business impact.

👉 Read the full report

More AI Basics Episodes

Founders, operators, and builders — catch up on our full Startup Basics series (Legal, Finance, Growth & AI):

👉 thisweekinstartups.com/basics

Links from episode:

Check out Photoroom: https://www.photoroom.com/

Check out Google Cloud: https://cloud.google.com/

Follow Matt:

X: https://x.com/matthieurouif

LinkedIn: https://www.linkedin.com/in/matthieurouif/

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Substack: https://twistartups.substack.com