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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.

This Week in Startups

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 unsettled and will take years to shake out
 • The difference between 
training data • and 
output • in legal terms
 • How “fair use” really works (and why it’s a defense, not a permission slip)
 • The risks of scraping vs. licensing, and why open source ≠ free use
 • How investors are diligencing AI startups around training data
 • Why startups must think differently once they’re funded vs. hacking in a dorm room

Whether you’re building an AI product, investing in one, or just trying to understand where the law is headed, this conversation breaks down the real legal risks every founder should know.

Timestamps:

(0:00) Jason introduces the Startup Legal Basics series & Chris Paniewski

(1:25) Why AI copyright law is unsettled

(3:40) Training data: scraping vs. licensing

(6:05) Open web ≠ open license; pitfalls around terms of service

(8:15) Investor diligence & risks around training data

(11:00) Open source & Creative Commons: common founder mistakes

(13:25) “Fair use” explained: the four-part test

(15:45) Why most disputes never make it to case law

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

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

Follow Chris:LinkedIn: https://www.linkedin.com/in/christopher-paniewski-09331a59/

Follow Jason:

X: https://twitter.com/Jason

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

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

AI Copyright & Training Data w/ Chris Paniewski | Wilson Sonsini Startup Legal Basics

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 fellow TWiST500 company Etched, Positron is building custom chips to take on the computing work required to deliver your AI query results faster and with less power draw than what GPUs can offer. With AI inference compute demand rising, the fellow Valor-backed startup has even more powerful systems coming to market in 2026 that have our hopes up that the AI cost curve can continue to point downward.

Timestamps:

 • 0:00 - A future with more efficient and accessible intelligence
 • 0:41, the following sponsors are mentioned: AlphaSense, Vanta, and Oracle Cloud Infrastructure
 • 1:26 - Introduction to the episode and the two featured companies, Republic and Positron
 • 2:43 - The history and purpose of Republic, a financial crowdfunding platform
 • 5:39 - Discussion of the current state and growth of equity crowdfunding
 • 9:19 - Kendrick Nguyen explains Republic's role as a financial infrastructure company, not a competitor to venture capital firms
 • 11:17 - Sponsor: Oracle Cloud Infrastructure
 • 12:25 - Republic's different products, Republic Capital and Republic Venture, are explained
 • 14:00 - The challenges and progress of secondary trading for non-accredited investors
 • 20:14 - Sponsor: Vanta
 • 21:21 - The concept of a unified "e-finance" infrastructure is introduced
 • 25:45 - Positron CEO Mitesh Agarwal discusses the future of AI chips and the limitations of current GPUs for inference workloads
 • 31:12 - Sponsor: AlphaSense
 • 32:22 - Discussion on the inefficiency of GPUs for inference and how Positron's Atlas system addresses it
 • 38:30 - Positron's strategy of using their Atlas system to prove their technology and generate revenue
 • 42:51 - The market shift from AI training to inference and the future of Positron's chips
 • 51:14 - The confidence in Positron's capital efficiency and their ability to compete with NVIDIA
 • 52:47 - Positron's focus on linear algebra acceleration rather than just transformers

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:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

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

Follow Jason:

X: https://twitter.com/Jason

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

Thank you to our partners:

(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist

(31:43) .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:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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

🎥 Watch the full episode here 👇

Republic opens private markets as Positron takes on GPUs: A TWiST500 doubleheader! | E2176

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 hacks for sales cycles in regulated industries — castles, moats & alligators!

(03:50) Meet Paid.ai: tracking costs & monetization for AI agents

(04:35) Paid.ai’s Manny Medina on the “year of agents” & early enterprise traction

(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(11:06) The tough economics of AI agents vs SaaS — margins squeezed by tokens

(18:20) How Paid.ai gets granular: tracking signals & agent activity with OpenTelemetry

(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist

(29:16) Enter iTruckr: Camilo Ramirez brings AI dispatch to the freight industry

(31:43) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

(39:02) Scaling from small fleets to mid-sized trucking companies — lessons from AI Trucker

(55:59) Tenax ai helps homeowners & insurers manage wildfire, flood & climate risk

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:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

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

Follow Jason:

X: https://twitter.com/Jason

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

Thank you to our partners:

(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist

(31:43) .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:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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

How Founders Are Building the Next Great Startups | Paid.ai, iTruckr & Tenax AI | E2175

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 the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(11:10) Jason heard Lina Khan on The Bulwark and he has THOUGHTS

(12:40) Google doesn’t have to divest Chrome! So what ARE the remedies?

(18:31) Atlassian’s buying a browser company? Which one? THE Browser Company.

(20:57) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech

(21:22) When early DPI is better than NO DPI.

(26:58) AI that helps you GET a job?! What a twist!

(29:46) Jason and Alex have questions about that MIT AI study…

(30:57) 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.

(32:07) More Browser News! Why Jason’s bullish on Brave.

(35:10) Perplexed by “Perplexity”: Jason’s rules for domain names

(39:54) The path is cleared for Polymarket’s return to the US

(47:06) Jason’s “Two Stock Markets” theory

(53:02) Mistral looking to raise 2 billion… euro!

(56:08) Jason’s political philosophy: More joy and happiness

(59:18) Stripe’s new stablecoin blockchain has no native token! So what’s it for?

(01:04:12) Jason’s tips for lowering your churn rate

(01:11:56) How to use Reddit to uncover pain points

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:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

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

Follow Jason:

X: https://twitter.com/Jason

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

Thank you to our partners:

(10:44) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(20:57) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech

(30:57) 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.

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:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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

The Browser Wars heat up! PLUS, Khan on The Bulwark, rules for great domain names, and Polymarket returns | E2174

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

*

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

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

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:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

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

Follow Jason:

X: https://twitter.com/Jason

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

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

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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

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

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

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:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

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

Follow Jason:

X: https://twitter.com/Jason

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

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

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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

Jason’s Tesla Optimus prediction, Anthropic’s latest mega-raise and more | E2172

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

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

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

Follow Lon:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

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

Follow Jason:

X: https://twitter.com/Jason

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

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:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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

KPop Demon Hunters breaks records, Grok speeds up, and an AI-powered browser deep dive | E2171

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:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

Market Update and Trends w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

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

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

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Follow Lon:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

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

Follow Jason:

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

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Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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

Google is Nano Banana, Apple AI plans & The Great H1B Visa Debate | E2170

This episode is full of tactical advice for improving your marketing operations. Gravitr's Doriane Mouret explains how to improve your conversion funnels (3:28), Outlaw's Danielle Vincent shares how to improve your SEO (33:45), then Jason joins for a Q&A covering the right cadence, location, and quality of content to publish (47:21).

Marketing SEO & Conversion Funnels | Scaling Your Startup S2 E6: Gravitr’s Doriane Mouret & Outlaw’s Danielle Vincent | E1218

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