Today’s show:

Jason sits down with Wilson Sonsini partner Chris Paniewski for part two of our Startup Legal Basics series on AI law — this time tackling the question every founder is asking: who owns the output of AI systems?

Chris has advised on some of the biggest AI deals in history, and in this episode he helps break down how intellectual property law is colliding with generative AI.

Jason and Chris cover:

• What kinds of IP rights might apply to AI-generated output (copyrights, patents, trade secrets)
• Why human authorship is central to copyright law
• Whether prompts are protectable IP
• How GenAI platforms’ terms of service affect ownership
• Real-world examples from Star Wars to Wirecutter to Warhol
• What startups should document when using AI in development
• How investors diligence AI companies on IP strategy

If you’re a founder, investor, or operator trying to understand how to responsibly use AI without losing your IP, this conversation is essential.

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Timestamps:

(0:00) Jason introduces part two of Startup Legal Basics with Chris Paniewski

(1:20) Star Wars example: using LLMs to generate existing IP

(3:10) Human authorship requirement in copyright law

(5:25) Prompts, super-prompts, and the role of creative control

(7:45) Photography analogy & the “monkey selfie” case

(10:00) Patents, inventorship, and AI-generated inventions

(12:05) Startups balancing speed to market vs. protectable IP

(14:15) How to layer human creativity on top of AI output

(16:20) Fair use, derivative works, and investor diligence

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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:

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

*

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Today’s show:

Hear why Eric Jackson thinks Opendoor is the new Carvana, and how he’s planning to bring Drake on board as an investor (plus Jason’s Bestie Chamath).

On a brand-new TWiST, Jason and Alex are chatting with Jackson of EMJ Capital about his hunt for elusive 100 baggers (stocks that return 100-to-1).

PLUS we’re chatting with Weave Robotics’ Kaan Doğrusöz about designing practical domestic robots RIGHT NOW, rather than prototypes for 2030. Hear about how they got Isaac to fold laundry like a pro.

All that and… how Jason would turn around TechCrunch, why board members should always have skin in the game, that Waymo motorcycle accident, AND Uber and Tesla’s first team-up to haul freight!

Timestamps:

(0:00) Jason is worried about the next generation facing the end of apprenticeship; here’s his advice for young workers

(10:24) 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!

(11:30) Kaan Doğrusöz of Weave Robotics joins to talk about getting his laundry-folding robot, Isaac, into customer’s homes

(18:01) Isaac doesn’t have hands; here’s how Weave makes it work with grippers

(20:44) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.

(21:48) Show Continues…

(24:51) Checking out some of Weave’s competitors… how did they settle on Isaac’s design?

(30:01) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(31:10) What’s going on with TikTok?

(36:15) Jason’s pitch is “BOYA”: Bring Your Own Algorithm

(38:54) Eric Jackson of EMJ Capital stops by to talk up $OPEN and why he wants Drake to invest

(40:14) Eric’s early YouTube career as an activist Yahoo! Investor

(44:42) Lessons Eric learned from Carvana and how that informed his $OPEN bet

(01:00:30) Why bringing Keith Rabois back was Eric’s ultimate dream for Opendoor

(01:03:02) Why board members should always have “skin in the game” and why $OPEN wants Chamath back

(01:07:26) Tesla and Uber are finally working together… They said it was impossible!

(01:09:31) A look at YouTube’s new AI podcasting features

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Thank you to our partners:

• 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!
• Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.
• Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

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:

On a special edition of TWiST, Alex presents a trio of TWiST 500 interviews.

First up, Medium CEO Tony Stubblebine on the company’s new Really Simple Licensing (or RSL) initiative, and how it’s helping to compensate writers for their content.

THEN, Human Native CEO Dr. James Smith joins for an even deeper dive on AI licensing, why a writer’s content isn’t just DATA to them, and why the company is pivoting away from its old marketplace model.

FINALLY, Jason Marks of TELO Trucks stops by to show off his EV mini-truck, walk us through why people need a powerful but tiny truck, and explain why they’re building trucks right here in the US of A.

Timestamps:

(0:00) Intro: It’s a trio of TWiST 500 interviews today!

(02:57) Alex chats with Medium CEO Tony Stubblebine

(04:54) Why Medium’s more worried about HIDING from AI than anything else

(10:24) Nexos.ai. Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at nexos.ai/twist.

(11:27) Show Continues…

(15:02) What is RSL and why aren’t AI companies offering publishers a good value?

(19:58) Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.

(20:59) Show Continues…

(22:03) How Medium calculates its revenue split with writers

(26:57) Alex welcomes Human Native CEO/founder Dr. James Smith.

(27:34) Writers see their content as their life’s work, but tech co’s just see DATA

(30:01) DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to DevStats.com/twist

(31:06) Show Continues…

(33:01) Why H.N. is pivoting away from licensing and the marketplace model

(47:23) TELO Trucks CEO Jason Marks joins the show

(48:25) What is a “mini-truck” and why they’re TELO’s focus

(52:28) Why TELO is building their EV trucks right here in the US

(54:42) Why towing capacity still matters, even on a mini-truck

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Follow Lon:

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Thank you to our partners:

Nexos.ai. Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at nexos.ai/twist.

Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.

DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to DevStats.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:

There are new LAUNCH Accelerator and Founder U cohorts this week, and Jason’s running down some of his favorite new startups.

PLUS Alphabet is the latest member of the $3T club, why Eric Schmidt was SO RIGHT about remote work, Robinhood is opening up private companies to more investors, Polymarket adds earnings reports, how Jason wagered on The Emmys this year, and MORE!

Timestamps:

(0:00) It’s kickoff day for LAUNCH Accelerator 35 AND Founder University!

(02:32) Let’s talk about some new companies. Jason runs down the LA35 line-up and why he’s excited about these awesome startups.

(10:33) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist

(11:57) Show Continues…

(19:50) Squarespace - Turn your idea into a beautiful website! Go to http://www.squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.

(21:05) Show Continues…

(27:43) Lemon.io - Hire pre-vetted remote developers and get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(28:58) Looking back at Jason’s solar energy rematch vs. Energy Sec. Chris Wright.

(31:23) Why Jason thinks solar power (+nuclear) is the future.

(41:03) Why Alphabet is the latest member of the $3 trillion market cap club.

(46:40) Jason says Eric Schmidt was right about work from home culture

(48:51) How Robinhood is giving everyday investors access to private companies

(51:44) Polymarket introduces prediction markets for corporate earnings.

(53:58) Why Jason loves prediction markets… and how he gambled on the Emmys this year.

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

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Thank you to our partners:

OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist

Squarespace - Turn your idea into a beautiful website! Go to http://www.squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.

Lemon.io - Hire pre-vetted remote developers and get 15% off your first 4 weeks of developer time at https://Lemon.io/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:

On Friday’s TWiST, Jason, Alex, and Lon look back at some highlights from this week’s big All-In Summit in Los Angeles, including a fiery, no holds barred presentation from Palantir CEO Alex Karp, Elon Musk delving into the key challenges facing Optimus, and Tucker Carlson debating Mark Cuban on Ukraine. PLUS… why schools may start blocking social media apps, the FTC’s new investigation into social chatbots, AND omnidirectional Zoox robotaxis are headed to Las Vegas.

Timestamps:

• Welcome back to TWiST!
• (1:52) Jason’s thoughts on the killing of Charlie Kirk
• (10:34) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST
• (10:52) Show Continues …
• (12:15) Reacting to All-In Summit highlights (Elon Musk, Alex Karp, Tucker Carlson, Mark Cuban)
• (21:23) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits
• (22:18) Show Continues …
• (26:09) Palantir, Alex Karp, and debate dynamics
• (31:03) 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
• (32:13) Show Continues …
• (45:03) How the internet used AI tools to make sense of Charlie Kirk’s death
• (56:22) Why Jason thinks it’s smart to block social media during school hours
• (1:03:43) The FTC chatbot investigation leaves out Anthropic’s Claude… here’s why
• (1:13:27) Zoox robotaxis make their Vegas debut… Here’s how they’re different from Waymo
• (1:19:38) Are Tesla robotaxis headed for CA soon? Polymarket says… maybe
• (1:27:21) Closing remarks and banter

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

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Thank you to our partners:

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

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

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

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

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/

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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) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist⁠⁠ (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) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(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) 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(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

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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

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🎥 Watch the full episode here 👇

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

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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:

(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

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

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Follow Lon:

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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.

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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

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

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

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

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