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This Week in Startups

Jason Calacanis

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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.

Afleveringen

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

    30 oktober 2026 · 1 uur 11 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    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 Bin…

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

    29 oktober 2026 · 1 uur 12 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    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 …

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

    27 oktober 2026 · 57 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    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 l…

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

    24 oktober 2026 · 1 uur 33 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    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…

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

    22 oktober 2026 · 1 uur 41 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    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” trai…

  6. Anthropic Gives Away 5% of Its Shares, Clone’s Muscle Robot, ElevenLabs Steals Podcaster's Voice

    20 oktober 2026 · 1 uur 34 min

    Afspelen
    This Week In Startups is made possible by:
    Plaud: https://plaud.ai/twist
    Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain
    Vanta: https://www.vanta.com/twist
    Rippling: https://rippling.ai/twist
    Today’s show:
    Jason can’t stop praising Nathan Fielder’s new A24 hybrid documentary about Elizabeth Holmes and Theranos, “You Can See Everything,” and he’s insisting that Lon check it out before the next podcast. Hear his spoiler-free review, how the film upended his expectations based on Fielder’s previous work, and why Lon also recommends Lance Oppenheim’s HBO Max series “Ren Faire.”
    Plus, we’re talking to Clone Robotics co-founder and CEO Dhanush Radhakrishnan about why he thinks robots should not just be humanoid but should look and move precisely like humans. We’re digging deep into how his hydraulic myofiber artificial muscle technology alters and even improves on the pulley-based systems being deployed by competitors, why he thinks the models that power domestic helper-bots will be commoditized, and how quickly he thinks he can put a robo-butler in every American home.
    Plus we’re comparing the potential impact of Anthropic’s new Public Benefit Fund vs. Elon Musk’s plan to give every baby a share of SpaceX, and re-considering simulation theory after Odyssey dropped an artificial fruit fly brain into an artificial landscape.
    Guest
    Dhanush Radhakrishnan on X: https://x.com/dhanushisrad
    Clone Robotics: https://clonerobotics.com/
    Related Links
    “You Can See Everything” trailer: https://www.youtube.com/watch?v=HvW_N5p1q44
    “You Can See Everything” on Rotten Tomatoes: https://www.rottentomatoes.com/m/you_can_see_everything
    John Carreyrou’s Theranos investigation (Wall Street Journal): https://www.wsj.com/articles/theranos-has-struggled-with-blood-tests-1444881901
    “Ren Faire” HBO Max trailer: https://www.youtube.com/watch?v=CHZUVTrrexE
    “Nathan for You”: Smokers Allowed clip (Comedy Central): https://www.youtube.com/watch?v=HttB2fYAm-8
    Anthropic: I…
    Lees meer
  7. Flying Cars, OpenAI Spies, Why AI Isn’t Sticking (Superhuman CEO)

    17 oktober 2026 · 1 uur 33 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    Lightfield: https://lightfield.app

    Every.io: https://every.io/

    PayPal: https://paypal.com/business

    Plaud: https://plaud.ai/twist

    GoDaddy: https://www.godaddy.com/

    Today’s show:

    Today’s college grads are showing up to work at Jason’s company unable to write three sentences. He’s asking what Shishir Mehrotra of Superhuman, the company behind Grammarly, can do to fix that.

    Shishir delves into Superhuman’s reasons for acquiring GPTZero, the most popular AI detector, and the AI notetaker Fathom, and the spreadsheet startup Rows. Plus, how Shishir responds to accusations that Grammarly helps students cheat in the classroom, why writers should disclose when they’re collaborating with an LLM, and Jason's CEO wish list for fresh Grammarly features.

    In the news, Tesla demoed its long-awaited Roadster, which used SpaceX thrusters to do some flips and propel itself over five other Teslas… And OpenAI warned staffers that spies may be trying to seduce them in order to steal company secrets… And the shutdown of Character AI prompts Jason to declare: “AI relationships are evil.”

    Guests:

    Shishir Mehrotra on X: https://x.com/shishirmehrotra Superhuman: https://superhuman.com

    Relevant Links:

    Rows, the spreadsheet startup Superhuman bought, announces the deal → https://rows.com/blog/post/rows-is-joining-superhuman

    Superhuman to acquire GPTZero (Business Wire) → https://www.businesswire.com/news/home/20260623083788/en/Superhuman-to-Acquire-GPTZero-AI-Authenticity-Platform

    Is the Internet AI, GPTZero's live tracker of AI content on Reddit, LinkedIn and X → https://istheinternetai.com

    GPTZero AI Vision, the extension that flags AI posts as you browse → https://gptzero.me/ai-vision

    Superhuman acquires YC-backed notetaker Fathom (TechCrunch) → https://techcrunch.com/2026/09/14/superhuman-acquires-yc-backed-notetaker-fathom-as-productivity-platforms-push-for-agentic-work/

    Grammarly Authorship, which shows how much of your writing …

  8. The Ex-DeepMind Researcher Taking On China’s Open Source AI

    15 oktober 2026 · 1 uur

    Afspelen
    This Week In Startups is made possible by: Lees meer

    Paper: https://getpaper.ai/twist

    Superhuman: https://superhuman.com/

    Odoo: https://Odoo.com/twist

    Today’s show:

    Misha Laskin of Reflection AI joins Jason to explain why big companies are done renting their AI from closed labs. Enterprises want to keep their data, cut their costs, and tune their models to their unique businesses.

    Reflection is launching its first open-weight model, Beam, just three months after acquiring its first big cluster. Misha admits that Beam trails the best Chinese open models by a couple of months, and needs 3 to 4 times fewer tokens to reach the same answer, but nonetheless, the race is on.

    PLUS, Misha explains how “reward hacking” led that rogue OpenAI model to break out of its test sandbox and steal the answers from Hugging Face's servers. The model solved the problem, just not the way anyone intended.

    There’s simply no way a few hundred safety researchers at closed labs can catch every flaw; open source is how software has always been made secure. It's also why he wants America to lead in open models again.

    So how close is America to catching up to the Chinese open source leaders? Watch this brand new TWiST and find out.

    Guests:

    Misha Laskin on X: https://x.com/MishaLaskin

    Reflection AI: https://reflection.ai/

    Relevant Links:

    Introducing Beam, Reflection's first open model (Reflection AI) → https://reflection.ai/blog/introducing-beam

    Reflection AI unveils Beam as an open answer to Chinese labs (Semafor) → https://www.semafor.com/article/10/05/2026/reflection-ai-unveils-an-open-source-answer-to-chinese-labs

    Cursor's Composer 2 coding model, built on an open model (VentureBeat) → https://venturebeat.com/technology/cursors-new-coding-model-composer-2-is-here-it-beats-claude-opus-4-6-but

    micro1 passes $1 billion annual run rate, mentioned by Jason → https://www.einnews.com/pr_news/949082966/micro1-end-of-q3-update

    Hackers heat French supermarket fridges, sparking fires and spoilin…

  9. The Gadget That's Better in Crowds Than Your Phone + Ring’s Founder Before Amazon Bought It | E2349

    13 oktober 2026 · 1 uur 20 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    Plaud: https://plaud.ai/twist

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

    NetSuite: https://netsuite.ai/twist

    The Conservation Fund: https://conservationfund.org

    Today’s show:

    At packed concerts, festivals, and stadiums, your phone gets WORSE with every person who shows up. Totem gets better.

    Carter Fowler of Totem joins Alex to explain how his screen-free compass points you straight to your friends without relying on cell towers. Find out why Carter says Apple will never ship this in an iPhone, and why kids, ski patrols, and blind users have become some of his most loyal fans.

    PLUS, Lon and Alex dig into the archives for Jason's 2017 CES interview with Ring founder Jamie Siminoff, a year before Amazon bought the company. Jamie explains how a doorbell he couldn't hear in his garage became Ring, and why a strong mission is "cheating" when it comes to keeping a team focused. Then he tells Jason he wants to take Ring public, not sell it. Ironic because about a year later, Amazon bought it. And get ready for some hot takes on neighborhood license-plate cameras, years before the anti-Flock backlash.

    Guests:

    Carter Fowler on X: https://x.com/Carter_S_Fowler

    Totem: https://totemlabs.com

    Jamie Siminoff on X: https://x.com/JamieSiminoff

    Ring: https://ring.com

    Relevant Links:

    Totem Compass, the offline friend-finding compass → https://totemlabs.com

    Totem closes its $1.3M pre-seed round (Business Wire) → https://www.businesswire.com/news/home/20250212385814/en/Totem-Closes-%241.3M-in-Pre-Seed-Funding-to-Scale-Operations-for-Explosive-Demand

    Totem's community crowdfunding round → https://wefunder.com/totemlabs

    Totem's record Lost Lands deployment last year (Business Wire) → https://www.businesswire.com/news/home/20251009622355/en

    The Innovator's Dilemma by Clayton Christensen, mentioned by Alex → https://www.amazon.com/dp/1633691780

    Original TWiST Interview with Jamie from 2017 …

  10. Jason Reacts To Japanese Founder Pitches + Fireside Chat With Yuki Shirato

    10 oktober 2026 · 1 uur 25 min

    Afspelen
    This Week In Startups is made possible by: Lees meer

    Lightfield: https://lightfield.app

    Rippling: https://Rippling.ai/twist

    Upwork: https://upwork.com

    Today’s show:

    AssetHub built an AI agent that recreates licensed characters in 3D while respecting copyright rules... But Jason says he needs to think BIGGER. 11 founders pitched their companies to Jason and Yuki Shirato of Techstars Tokyo at our Osaka event this week, and neither investor held back.

    Find out why Jason says Seekr feels more like a vitamin than a painkiller, and needs to ditch the press mentions from their deck. Plus, a vital lesson for founders: if everyone already knows about the problem you're solving, investors expect a tight solution and business plan. Truly novel business ideas get more leeway. Japan's startup community is booming, with many recent grads bailing on lifelong gigs at major corporations to start companies. But here's why Yuki says the fear of failure is still holding back progress.

    Guests:

    Yuki Shirato on LinkedIn: https://www.linkedin.com/in/yuki-shirato

    Techstars Tokyo: https://www.techstars.com/accelerators/tokyo

    Founder Pitches:

    Seekr: https://seekrai.global/product

    Arabat: https://arabat.it/

    AssetHub: https://assethub.io/

    CRAZIA: https://crazia.co/

    JuJuJuu: https://jujujuu.com/

    JAPANMEDIA: https://lp.japanmedia.ai/

    Tsuin AI: https://www.tsuin.ai

    Rumi Light: https://www.rumilight.jp/

    GENCHI: https://www.toraru.me/en

    TattvaSilicon: https://tattvasilicon.com/

    Mimi AI: https://nihongo-chat-ruby.vercel.app/onboarding

    Relevant Links:

    Founder University Japan, Jason's pre-accelerator program with JETRO → https://japan.founder.university/

    Techstars Tokyo announces its Class of 2026 → https://www.techstars.com/newsroom/techstars-tokyo-accelerator-announces-class-of-2026

    Yuki Shirato on why Japan should be on every founder's radar (Techstars) → https://www.techstars.com/blog/insights-and-trends/should-japan-be-on-your-radar-as-a-founder

    How Techstars Tokyo is helping mak…

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