
Written by a model from the transcript; not yet reviewed.
This week on the roundtable, the panel dives into prediction markets, the cultural impact of Nathan Fielder’s documentary about Theranos and Elizabeth Holmes, and the intense legal and contractual disputes surrounding pro rata rights in early-stage venture capital. The guests examine the complexities of due diligence, how founders and investors navigate fraud, and the ongoing debate over the boundaries of AI, copyright, and right of publicity. They explore why prediction markets act as crucial information machines, the psychological dynamics of high-profile fraud cases, and how seed-stage funds protect their investments against shifting market pressures.
Hosts set the stage for the episode, explaining the format and announcing the panel of venture capitalists.
Discussion centers on using prediction markets for ski season forecasting, illustrating the broader concept of markets as information engines.
The panel dives into the documentary about Elizabeth Holmes, dissecting key scenes and themes while relating them to venture capital insights.
The hosts dissect how the documentary’s fragmented storytelling mirrors Elizabeth Holmes’ persuasive charisma, debating whether it’s a true documentary or a crafted narrative.
Discussion turns to Holmes’ future after prison, exploring potential new ventures, her ability to raise capital, and the broader implications for her personal brand.
The episode moves to the legal and ethical issues surrounding AI voice cloning, right‑of‑publicity, and the need for clear regulatory frameworks.
The conversation shifts to the importance of pro‑rata rights for early‑stage investors, the tension between founders and funds, and the evolving dynamics of seed‑stage deals.
Hosts debate the balance between protecting founders and safeguarding limited partners, arguing for a vibrant seed ecosystem that supports early‑stage startups.
Discussion turns to the new NIL rules, how they affect college athletes’ earnings, and the broader debate over revenue distribution in sports.
Discussion centers on the misuse of AI voice cloning, the MH370 video controversy, and the importance of authenticity in synthetic voices.
An in‑depth look at how to request and price celebrity voice usage, the negotiation process, and the nuances of what can be said in endorsements.
Hosts highlight promising companies—Knox Metals, Electric Plants, and Obliteration.ai—sharing their unique value propositions and recent funding milestones.
Markets as Information Machinesinsight
The guest explains Friedrich Hayek's philosophy on markets as pure information mechanisms. Placing financial bids helps society understand complex global realities.
The host jokes about buying an open snow platform clone entirely to generate tax write-offs for ski trips.
Dealing with Portfolio Frauddata
The guest shares that venture funds experience a small percentage of fraudulent companies and argues that some risk of fraud is natural in aggressive seed investing.
Non-Negotiable Pro Rata Rightsdebate
The guest argues that pro rata rights are non-negotiable for seed funds because the early-stage venture capital model cannot survive without them.
Calling Investor Bluffsstrategy
The host explains the exact tactic used when new lead investors try to strip away contractual rights from early backers.
Evaluating the Pro Rata Debatedebate
The panel debates why larger funds push back on pro rata rights and why many founders and smaller funds fold under pressure.
“Like Hayek is my favorite, and like, you know, Frederick Hayek's whole thing is markets are information machines.”
“Your bot's going to tell you about the breaking news. What we're going to do is just do a deep dive and what happened in that deal?”
“And I'll tell you why, Jason. I'm not sure if you feel the same way as, or anyone, is like, to me, I look at this, and I'm like,”
“I think the most interesting thing I noticed is when you talk about Elizabeth's magnetisms, like pull people into help her, is at the end of the movie, Amanda asked Nathan, like, oh, are you leaving things out that Elizabeth said?”
“The heel can become the hero, the hero can become the heel. You don't want to be in the middle.”
“The right of publicity means you can't use me to sell your thing.”
“If you spend a million on ads, I need 250.”
“The way, there's a very simple way to test this, is to put your cloned voice on 11 Labs with a price, and see if there's a market for it.”
“I think actually, the copyright is like already in there, the right to publicity is already in there and baked.”
“Obliteration.ai is where you will do that. And congratulations to them to being accepted to A16 Speedrun.”
This Week In Startups is made possible by: DigitalOcean - Head to https://do.co/twist to start building on DigitalOcean's AI-Native Cloud today — and cut your AI workload costs by up to 50% Odoo: The all-in-one business platform. Your first app is free! Get started today at https://odoo.com/twist Thanks to our partners at Rippling! Head to https://rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business. Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin S. You can check it out at https://plaud.ai/twist and use code TWIST for 10% off! Today’s show: Elizabeth Holmes remains in prison for defrauding Theranos investors, even as she stars in the hit Nathan Fielder/Lance Oppenheim documentary “You Can See Everything.” But we’re asking the real question: After all the very public accusations… the hit pieces in the press and the Hulu drama series picking apart the scandal… would tech investors and VCs be willing to back her NEXT startup, if the numbers were right? On today’s TWiST roundtable, Jason Calacanis is joined by Sam Lessin (Slow Ventures), Paige Finn Doherty (Behind Genius Ventures), and Jenny Fielding (Everywhere Ventures). In addition to reviews of the movie tech insiders can’t stop talking about, they cover why every seed portfolio needs a little bit of fraud, how diligence scales with check size, having trademark rights to your own voice, and the pro rata rights debate that’s still raging over Valar Atomics’ lawsuit with seed investors Day One Ventures. Guests Sam Lessin on X: https://x.com/lessin Slow Ventures: https://slow.co/ Paige Finn Doherty on X: https://x.com/paigefinnn Behind Genius Ventures: https://www.behindgeniusventures.com/ Jenny Fielding on X: https://x.com/jefielding Everywhere Ventures: https://www.everywhere.vc/ Relevant Links OpenSnow: https://opensnow.com/ “You Can See Everything” trailer: https://www.youtube.com/watch?v=HvW_N5p1q44 HBO Max “The Rehearsal” trailer: https://www.youtube.com/watch?v=2fjPFt8cpic Elizabeth Holmes moves to halfway house in 2027 (ABC7): https://abc7.com/story/elizabeth-holmes-scheduled-move-halfway-house-august-2027/19862832/ Billy Evans’ blood-testing startup Haemanthus (TechCrunch): https://techcrunch.com/2025/05/10/elizabeth-holmes-partner-reportedly-fundraising-for-new-blood-testing-startup/ Polymarket: Oscars 2027 Best Picture: https://polymarket.com/event/oscars-2027-best-picture-winner-20260727173620857 Kalshi: Oscars 2027 Best Documentary: https://kalshi.com/markets/kxoscardocu/event/kxoscardocu-27 Charlie Javice sentenced to 7 years (NBC News): https://www.nbcnews.com/business/business-news/charlie-javice-sentenced-7-years-prison-fraudulent-175m-sale-financial-rcna234536 Trump pardons Nikola founder Trevor Milton (Axios): https://www.axios.com/2025/03/28/trump-pardons-nikola-founder-trevor-milton Sequoia writes its FTX stake down to zero (Fortune): https://fortune.com/2022/11/10/ftx-sam-bankman-fried-sequoia-writes-down-214-million-investment-to-zero-venture-capital-crypto Who lost money on Theranos? (Fortune): https://fortune.com/2018/05/04/theranos-investment-lost “Barbarians at the Gate” on Amazon: https://www.amazon.com/Barbarians-Gate-Fall-RJR-Nabisco/dp/B08YP9MDHX a16z backs Adam Neumann’s Flow (Commercial Observer): https://commercialobserver.com/2022/08/adam-neumann-350m-backing-andreessen-horowitz/ Martin Shkreli lifetime pharma ban (FTC): https://www.ftc.gov/news-events/news/press-releases/2022/01/statement-chair-lina-m-khan-ruling-judge-denise-l-cote-federal-trade-commission-et-al-v-vyera Isaia Taylor post announcing Valar suit: https://x.com/isaiah_p_taylor/status/2108679133467414855 Day One Ventures response: https://x.com/mashadrokova/status/2108732979191390528 ElevenLabs Iconic Marketplace: https://elevenlabs.io/iconic-marketplace Apple Corps vs. Apple Computer, a history (MacTech): https://www.mactech.com/2004/04/09/a-history-of-the-apple-vs-apple-dispute Cameo for Business: https://www.cameo.com/business Nox Metals: https://noxmetals.co Electric Plant Company: https://www.electricplant.co/ Ablieration: https://abliteration.ai/ Timestamps: 0:00 Our new “This Week in VC” newsletter 2:15 Panel intro: Sam Lessin, Paige Doherty, Jenny Fielding 8:09 Why gambling loses appeal for VCs 11:02 Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at https://plaud.ai/twist and use code TWIST for 10% off! 16:18 DigitalOcean - Head to https://do.co/twist to start building on DigitalOcean's AI-Native Cloud today - and cut your AI workload costs by up to 50% 17:35 Best moments from “You Can See Everything” 21:42 Unreliable narrators and unknowable situations 24:41 Living in a post-truth moment 30:02 Due diligence horror stories 32:45 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://odoo.com/twist 34:50 The VCs remember their fraud investments 38:39 How LAUNCH trains founders to prep for diligence 44:31 How Elizabeth Holmes kept raising money 54:54 Would you invest in an Elizabeth Holmes company? 57:27 Thanks to our partners at Rippling! Head to https://rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business. 1:02:28 Why seed funds need pro rata rights 1:09:02 When “founder friendly” means rolling over 1:16:25 The three investor relationships: team, founders, LPs 1:21:02 ElevenLabs “Archer” voice controversy 1:27:16 How NIL deals reshaped college sports 1:33:54 Cameo for Business and long-tail celeb endorsements 1:35:51 Portfolio company shoutouts Subscribe to our newsletters on Substack: TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland 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
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