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This Week in Startups

Jason Calacanis
This Week in Startups
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  • This Week in Startups

    Binance Hacked $6.3B Stolen, DoorDash Buys Instacart For $17B, Jake Newfield from Hermetiq, + More!

    30.10.2026 | 1 godz. 10 min.
    This Week In Startups is made possible by:

    Stripe: https://stripe.com/startups

    Rippling: https://rippling.ai/twist

    Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain

    Plaud: https://plaud.ai/twist

    Today’s show:

    Binance lost an estimated $6.3 billion in the biggest crypto hack ever, and Jason proposes a radical solution. The entire tech industry should stop shipping new features for one month a year, and do nothing but patch. (Call it No App November?)

    On a busy Friday show, Jason and Lon dig into the. Binance breach and look back at Jason’s prescient 2021 warning about leaving your money in crypto exchanges. (He recommends spreading your wealth around various different banks!) Plus, why he’s giving CZ credit for backstopping customer losses out of his own fortune.

    Plus, DoorDash’s $17B acquisition of Instacart… Did DoorDash overpay? And is this happening now to avoid the harsher regulatory climate should Democrats regain power in the midterms?

    Then we’ve got Hermetiq co-founder and CEO Jake Newfield, who has twice won the LAUNCH Accelerator’s pitch competition. Hear the celebrated two-minute pitch for an AI build engineer, and find out why Jason thinks having a “lighthouse customer” makes such a huge difference.

    Finally, we’re awarding the Grand Prize in our $5K bounty competition to create Jason’s Annotated app, and remembering the legendary film and TV actor Sir Patrick Stewart.

    Guest

    Jake Newfield on LinkedIn: https://www.linkedin.com/in/jakenewfield/

    Hermetiq: https://www.hermetiq.com/

    Bazel: https://bazel.build

    Apply to the LAUNCH Accelerator: https://www.launch.co/apply

    Relevant Links

    Binance links the $6.3B theft to a compromised DevOps laptop (BleepingComputer): https://www.bleepingcomputer.com/news/security/binance-links-63-billion-crypto-theft-to-compromised-devops-laptop/

    The 1978 Lufthansa heist (History.com): https://www.history.com/articles/1978-lufthansa-heist-jfk-henry-hill-goodfellas

    Trump pardons Binance founder Changpeng Zhao (KWTX/AP): https://www.kwtx.com/2025/10/23/trump-pardons-binance-founder-changpeng-zhao

    CrowdStrike: https://www.crowdstrike.com/en-us/

    Palo Alto Networks: https://www.paloaltonetworks.com/

    Grant Cardone challenges Jason to $1M Bitcoin bet: https://www.thestreet.com/crypto/markets/grant-cardone-challenges-bitcoin-bear-to-1-million-bet

    DoorDash to acquire Instacart for $17B (TechCrunch): https://techcrunch.com/2026/10/29/doordash-to-acquire-instacart-for-17b/

    Economic Liberties calls on the FTC to block the deal: https://www.economicliberties.us/press-release/economic-liberties-calls-on-ftc-to-block-doordash-instacart-merger/

    Central Market, H-E-B's upscale banner, expands home delivery (Supermarket News): https://www.supermarketnews.com/foodservice-retail/central-market-expands-curbside-and-home-delivery

    People are using AI to make their smart TVs dumb again (TechCrunch): https://techcrunch.com/2026/10/19/people-are-using-ai-to-make-their-smart-tvs-dumb-again/

    TWiST $5K Bounties: https://bounty.thisweekinstartups.com/

    Founder University: https://founder.university/

    Founder University x Japan: https://japan.founder.university/

    Inside.com domain auction: https://inside.com/

    Yank Sing: https://yanksing.com/

    Cafe du Monde coffee and chicory: https://shop.cafedumonde.com/product/coffee-beignets/cafe-du-monde-coffee-and-chicory

    Patrick Stewart, "Star Trek" and "X-Men" actor, dead at 86 (CNN): https://www.cnn.com/2026/10/29/entertainment/patrick-stewart-death

    “Time Squared” (Star Trek: TNG S2E13): https://memory-alpha.fandom.com/wiki/Time_Squared_(episode)

    “Green Room” trailer: https://www.youtube.com/watch?v=Q8XSARX3DQg

    “X-Men: Days of Future Past” trailer: https://www.youtube.com/watch?v=pK2zYHWDZKo

    Timestamps:

    0:00 The largest crypto hack or theft in history

    5:45 Jason gives CZ credit for backstopping losses

    7:34 Jason’s cybersecurity proposals

    11:48 Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on https://stripe.com/startups.

    14:49 DoorDash buys Instacart for $17B

    18:48 Is DoorDash overpaying?

    24:28 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.

    26:26 Vibecoding your smart TV

    27:20 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!

    30:04 Jake Newfield (Hermetiq) gives a perfect pitch

    34:13 Got a new business idea? Northwest Registered Agent helps you bring it to life. Get a free domain, email, phone number, and more - with no purchase required! - Learn more at https://www.northwestregisteredagent.com/twistdomain

    37:12 Lead with your lighthouse customer

    43:14 The Cafe Du Monde branding lesson

    51:10 The Annotated Bounty finals begin

    1:04:00 Jason announces the grand prize winner

    1:07:34 RIP Sir Patrick Stewart

    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

    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
  • This Week in Startups

    Is AI the new cigarettes? Our VC panel digs into Anthropic’s S-1 | E2356

    29.10.2026 | 1 godz. 12 min.
    This Week In Startups is made possible by:

    PayPal: https://paypal.com/business

    The Conservation Fund: https://www.conservationfund.org/

    Hostinger: https://hostinger.com/twist

    Plaud: https://plaud.ai/twist

    Today’s show:

    Anthropic’s S-1 is here, and finally, we can start to develop a real understanding for the AI economy and whether the numbers add up. Anthropic shows an operating profit, a mostly non-cash $80.7 billion loss, and customers spending a shocking 9x what they were spending on intelligence just one year ago.

    Is this the greatest business in history? Is AI now as addictive to enterprises as cigarettes once were to impressionable teens?

    On this week’s VC Roundtable, Jason Calacanis is joined by D.A. Wallach (Time BioVentures), Dave McClure (Practical Venture Capital), and Ben Black (Akkadian Ventures / Powerlaw Corp.) to seek some answers.

    They dig into the numbers, including that wild 900% net revenue retention, and consider how retail investors will consider the convertible-note charge behind their $80B loss. Plus they’ll debate whether Anthropic’s founders are really true believers driven by religious fervor, and if so, whether they’re destined to be out-competed by “rabid capitalists.”

    Guests

    D.A. Wallach on X: https://x.com/dawallach

    Time BioVentures: https://www.timebioventures.com/

    Dave McClure on X: https://x.com/davemcclure

    Practical Venture Capital: https://practicalvc.com/

    Trading Places podcast: https://www.youtube.com/@PracticalVentureCapital

    Ben Black on LinkedIn: https://linkedin.com/in/benblack

    Akkadian Ventures: https://akkadian.vc/

    Powerlaw Corp: https://pwrl.com

    Relevant Links

    Anthropic’s S-1, by the numbers (Fortune): https://fortune.com/2026/10/27/anthropic-s1-ipo-filing-financials-profits/

    900% NRR and an $80.7B loss that mostly ins’t (HackerNoon): https://hackernoon.com/anthropics-s-1-shows-163b-in-half-year-revenue-a-900percent-nrr-and-an-807b-loss-that-mostly-isnt

    Tickertrends: https://tickertrends.io/

    Replit makes OpenAI its default (TechCrunch): https://techcrunch.com/2026/10/17/replit-is-no-longer-working-with-anthropic-ceo-says/

    Dario Amodei warns that rivals’ spending could risk bankruptcy (Fortune): https://fortune.com/2026/02/14/anthropic-ceo-dario-amodei-spending-capex-risk-ai-revenue-forecasts-bankruptcy

    Machines of Loving Grace (Dario Amodei): https://www.darioamodei.com/essay/machines-of-loving-grace

    Palantir CTO Shyam Sankar says AI researchers are taking up smoking (Fortune): https://fortune.com/2026/10/13/palantir-cto-shyam-sankar-ai-researchers-smoking-cigarettes-cure-cancer-artificial-general-intelligence-silicon-valley-mass-psychosis-effective-altruism/

    Microsoft offers its first-ever voluntary buyouts (TechSpot): https://www.techspot.com/news/112174-microsoft-offers-voluntary-buyouts-thousands-us-workers-ai.html

    Canva ranks among the top consumer AI apps (SmartCompany): https://www.smartcompany.com.au/artificial-intelligence/canva-new-ai-consumer-web-app-ranking-andreesen-horowitz/

    SpaceX Q3: Musk says it could rent out its AI compute several times over (Constellation Research): https://www.constellationr.com/insights/news/spacexs-q3-musk-says-it-could-rent-out-its-ai-compute-several-times-over

    Jason’s 2026 “Bitcoin is Dead” post: https://x.com/Jason/status/2114956980674605075

    Jason to Michael Saylor: "there are better places to invest your money”: https://x.com/Jason/status/2115274438979756346

    Timestamps:

    0:00 Anthropic files its public S-1

    4:58 Anthropic vs. OpenAI revenue run rates

    9:20 PayPal is built for all businesses. Get started at https://paypal.com/business

    10:02 “The greatest business in the history of capitalism”

    11:58 Is intelligence the new tobacco?

    18:08 The “meat sack constraint”

    20:36 Thanks to our partner, The Conservation Fund! Learn more at https://www.conservationfund.org/

    22:13 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!

    24:32 The Who Has the Most Subscribers Challenge

    28:08 Is Apple waiting out the AI race on purpose

    30:22 Hostinger: The all-in-one platform for domains, websites, email, and marketing. Go to https://hostinger.com/twist and use the code TWIST for an additional 10% off Black Friday and Cyber Monday

    34:19 Is Canva an AI company?

    39:08 True Believers who still want to make money

    48:21 The $72.4B convertible-note charge, explained

    51:03 How long does AI compute stay useful?

    58:19 Jason’s monthly “Bitcoin is Dead” post

    1:04:41 Alicorns are unicorns with pegasus wings

    1:09:58 Subscribe to the TWiST Newsletter!

    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 Jason:

    X: https://twitter.com/Jason

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

    Thank you to our partners:

    PayPal is built for all businesses. Get started at https://paypal.com/business

    The Conservation Fund: Thanks to our partner, The Conservation Fund! Learn more at https://www.conservationfund.org/

    Hostinger: The all-in-one platform for domains, websites, email, and marketing. Go to https://hostinger.com/twist and use the code TWIST for an additional 10% off Black Friday and Cyber Monday

    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!

    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

    Subscribe to our Substack Newsletters!

    TWiST: https://twistartups.substack.com/

    TWiAI: https://www.thisweekinai.ai/

    TWiVC: https://thisweekinvc.substack.com/

    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
  • This Week in Startups

    Pregame Your Launch Before Your App Exists (w/ Amanda Bradford) | E2355

    26.10.2026 | 56 min.
    This Week In Startups is made possible by:

    Odoo: https://odoo.com/twist

    G2i: https://g2i.co/twist

    Rippling: https://rippling.ai/twist

    Plaud: https://plaud.ai/twist

    Today’s show:

    Amanda Bradford’s “launch party” for her dating app The League actually extended for months.

    She “pre-gamed” the app’s formal launch with months of mixers, boat parties, and free events, where the only ticket required for admission was having the app on your phone.

    By launch day, she had a massive wait list, and still just let in 500 people, who ensure maximum buzz (and FOMO).

    At LAUNCH’s first-ever Tactical & Practical live event from San Francisco, Amanda walks the crowd through how she built a vetted, two-sided dating marketplace as a solo founder, eventually getting prominent enough to attract the attention of Match Group. (She sold The League for ~$30 million in 2020.)

    Hear exclusive tips you won’t get anywhere else, like how Amanda used a “fake paywall” to gauge willingness to pay for subscriptions, and how to time your rate of expansion into new markets.

    Plus, an all-new Flashback segment, featuring Alex and Lon looking back at a classic 2017 interview between Jason and Stripe’s Patrick Collison.

    Guests

    Amanda Bradford on X: https://x.com/amandabradford

    Book a Call with Amanda: https://intro.co/amandabradford

    The League: https://www.theleague.com/

    Patrick Collison on X: https://x.com/patrickc?lang=en

    Stripe: https://stripe.com/

    Relevant Links:

    The League was called "elitist." Its founder says that was never the case (CNBC): https://www.cnbc.com/2023/10/20/founder-of-the-league-on-dating-ambition-and-that-viral-ad-campaign.html

    Alex Wilhelm’s Cautious Optimism: https://www.cautiousoptimism.news/

    TWiST E723: Patrick Collison (2017): https://www.youtube.com/watch?v=P-NepiMQGvY

    Timestamps:

    0:00 Amanda Bradford on building The League

    4:30 Hand-reviewing early applications

    6:40 Building an MVP with a rented co-founder

    8:56 The VIP approach

    13:10 Why Amanda only let in 500 people

    15:44 The “Heavy Hitter” fake paywall test

    16:44 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://odoo.com/twist

    17:46 Why live events are the real unlock

    21:35 Controversy as a hook

    24:22 Flashback to Patrick Collison in 2017

    25:13 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!

    28:13 Stripe: Then vs. Now

    30:53 G2i has been recruiting software engineers for over a decade. Go to https://g2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks.

    32:17 Why did PayPal stay PayPal?

    37:50 Problem, not a product

    44:33 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.

    45:46 The outage nobody noticed

    51:00 Why persistence beats pivoting

    52:13 What’s left before a Stripe IPO?

    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

    Thank you to our partners:

    Odoo: The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist

    G2i has been recruiting software engineers for over a decade. Go to G2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks.

    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!

    Check out all our partner offers: https://partners.launch.co/
  • This Week in Startups

    OpenAI’s $1.25T Raise, Starlink Mobile & Zuck’s Tax Deal | EP 2354

    24.10.2026 | 1 godz. 33 min.
    This Week In Startups is made possible by:

    Plaud - https://plaud.ai/twist

    Sentry - https://sentry.io/twist

    Lightfield - https://lightfield.app

    Rippling - https://rippling.ai/twist

    Today’s show:

    Is OpenAI finally priced correctly? Jason argues that the reported $30 billion raise at a $1.25 trillion valuation is finally “right-sized.” He also says that he’d put money in at that price, while walking through the risks that could still sink the investment.

    It’s a Friday all-news episode with Jason and Lon, covering OpenAI’s latest round, SpaceX’s push to become America’s fourth major carrier, Zuck and Meta’s creative move around the proposed California billionaire tax, and some of Lon and Jason’s favorite documentaries.

    Plus we’re asking the timely question: who watches the AI watchdogs?

    Relevant Links

    OpenAI nears up to $30B round at $1.25T valuation, led by UAE investors (CNBC): https://www.cnbc.com/2026/10/22/openai-funding-round-uae-investors.html

    Anthropic investors eye a $2T IPO (Nasdaq): https://www.nasdaq.com/articles/move-over-spacex-anthropic-targets-2-trillion-valuation

    Uber puts all 30,000 employees on ChatGPT Work (TechCrunch): https://techcrunch.com/2026/10/22/uber-puts-all-30000-employees-on-chatgpt-work/

    Telecom stocks fall as SpaceX eyes 80,000 cell sites (Yahoo Finance): https://finance.yahoo.com/markets/stocks/articles/telecom-stocks-fall-spacex-eyes-134838815.html

    Verizon launches simpler plans and drops activation and upgrade fees (Fox Business): https://foxbusiness.com/markets/verizon-launches-simpler-plans-new-loyalty-program-drops-some-fees

    Amazon Leo's launch slips past early 2026 (ITdaily): https://itdaily.com/news/network/amazon-leo-faces-delays/

    METR and Redwood Research's write-up on red-teaming OpenAI's agent monitoring: https://metr.org/blog/2026-10-22-red-teaming-openai-agent-monitoring/

    Open Philanthropy is now Coefficient Giving: https://coefficientgiving.org/research/the-story-behind-our-new-name/

    Court documents show the alleged FSU shooter's ChatGPT chats (AOL): https://www.aol.com/news/court-documents-show-florida-state-233829466.html

    Meta's 8-K filing on the Founder Alignment Agreement (SEC): https://www.sec.gov/Archives/edgar/data/0001326801/000162828026066700/meta-20261019.htm

    Polymarket: will California's billionaire tax pass?: https://polymarket.com/event/billionaire-one-time-wealth-tax-passes-in-california-election-2026

    Mark Cuban vs. Ro Khanna on the billionaire tax (Fortune): https://fortune.com/2026/08/17/mark-cuban-california-billionaires-tax-wealth-ro-khanna/

    Elizabeth Holmes: The Theranos Deception (60 Minutes archive): https://cbsnews.com/video/elizabeth-holmes-the-theranos-deception-60-minutes-archive

    “The Act of Killing” trailer: https://www.youtube.com/watch?v=Q3FcB1UZHlg

    “Grizzly Man” trailer: https://www.youtube.com/watch?v=uWA7GtDmNFU

    “Hoop Dreams” trailer: https://www.youtube.com/watch?v=uf9Nq2ju0t0

    “The King of Kong” trailer: https://www.youtube.com/watch?v=L5XvArGGIzk

    “A Short Stay in Hell” by Steven L. Peck: https://www.amazon.com/dp/0983748446

    “The Library of Babel” by Jorge Luis Borges [PDF]: https://sites.evergreen.edu/politicalshakespeares/wp-content/uploads/sites/226/2015/12/Borges-The-Library-of-Babel.pdf

    “The Eureka Machine” by Richard Socher: https://www.amazon.com/dp/154170570X

    Timestamps:

    0:00 Jason’s in SF with the LAUNCH Accelerator 37 cohort

    2:40 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!

    6:34 Tactical & Practical talks live at Salesforce Tower

    10:21 Using Claude for brainstorming, not writing

    19:26 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26

    20:42 OpenAI closing $30B at a $1.25T valuation

    26:04 Why OpenAI could still lose

    30:25 Would you put 30% of your retirement into OpenAI?

    32:34 Lightfield - Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you - it even prospects and books your meetings. Used by thousands of startups. Free at https://lightfield.app

    34:27 Every Tesla becomes a Starlink hotspot

    43:06 What would be the ultimate SpaceX domain name?

    45:00 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.

    46:10 Is METR a fair watchdog for OpenAI?

    54:03 Jason’s “Know Your Customer” plan for AI models

    1:03:34 Meta’s deal to keep Zuckerberg in Cali

    1:14:35 Why Jason would raise the minimum wage

    1:18:42 Does Nathan Fielder give Liz Holmes a pass?

    1:30:59 “A Short Stay in Hell” and “The Eureka Machine”

    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

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

    Substack: https://twistartups.substack.com
  • This Week in Startups

    We asked 3 VCs: would you invest in Elizabeth Holmes’ next startup? | E2353

    22.10.2026 | 1 godz. 41 min.
    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:

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

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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.
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