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This Week in Startups

Jason Calacanis
This Week in Startups
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1428 episodes

  • This Week in Startups

    How to Raise a Seed Round in 2026: Ask Jason | E2294

    2026/05/29 | 57 mins.
    This Week In Startups is made possible by:

    partner 1 - link
    partner 2 - link
    partner 3 - link

    Today’s show:
    Jason breaks down the real math behind raising a seed round. Here’s the funnel: contact 150 firms, get 50 first meetings, convert 2o into second meetings, and close 2 term sheets.
    PLUS Jason responds to viewer questions about why hardware is no longer a dirty word for investors, how to differentiate your startup from frontier-model companies like OpenAI, even when they’re in your niche. Plus a pitch for “Founder Community College,” and anecdotes from Lon’s European odyssey.

    Thanks for the Questions:

    Richard Corral: CEO of Quanto: https://quanto.co/
    ØnProtons on X: https://x.com/0nProtons
    SergeDawg on X: https://x.com/sergedawg
    Mahika Golani
    Peridot: https://www.tryperidot.com/
    Shawn Sully on X: https://x.com/aroogle
    Programs and Accelerators Mentioned:
    Y Combinator: https://www.ycombinator.com/
    Techstars: https://www.techstars.com/
    Antler: https://www.antler.co/
    PearX: https://pear.vc/pearx/
    Sequoia ARC: https://www.sequoiacap.com/arc/
    Kauffman Fellows: https://www.kauffmanfellows.org/
    Companies and Startups Referenced:
    Whoop: https://www.whoop.com/
    Knightscope: https://knightscope.com/
    Eight Sleep: https://www.eightsleep.com/
    Cafe X: https://www.cafexapp.com/

    Media Referenced:

    New Yorker Sam Altman profile: https://www.newyorker.com/magazine/2026/04/13/sam-altman-may-control-our-future-can-he-be-trusted
    Off-Duty Recommendations
    Terra Kaffe Demi compact automatic espresso machine: https://www.terrakaffe.com/products/tk-demi
    Osteria Pastella (Florence, Italy): https://www.osteriapastella.it/

    Timestamps:

    0:00 Inside the TWiST private group chat
    3:25 How to react when an investor says your "too early."
    6:50 The ultimate seed round funnel
    8:48 Jason's new Associate in Training program
    10:09 Grasshopper Bank - Time is money. Don't waste either. Go to https://grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account.
    18:28 How have the metrics for early-stage companies changed?
    20:20 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist
    22:34 TWiST Bounties update
    23:43 Competing against frontier labs
    30:03 What signals real investor-founder alignment?
    30:14 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist
    36:07 A crash course in Bay Area startup culture
    40:15 Automatons-as-a-Service (AaaS)
    42:29 Who in Silicon Valley does Jason really not like?
    49:59 Museum Etiquette with Lon Harris

    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
    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
    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
  • This Week in Startups

    The Drone Company Quietly Taking Over Delivery

    2026/05/27 | 1h 1 mins.
    This Week In Startups is made possible by:
    Render - render.com/twist
    Deel - deel.com/twist
    Northwest Registered Agent - northwestregisteredagent.com/twist
    Today’s show:
    The "Ryanair of drone delivery" just raised $50 million and plans to bring its technology from Europe to the United States. Manna founder Bobby Healy explains to TWiST how his Dublin-based company completed 300,000 deliveries while some rivals are still publishing blog posts, and why low-cost airline economics will decide who wins the autonomous skies.
    Sticking to the drone theme, TWiST welcomed Theseus co-founder Ian Laffey, who called in from Kyiv to tell us about his company’s drone guidance system. It runs off a simple camera and Google Maps. The technology could rewrite the modern, GPS-jammed battlefield, and bring more firepower to smaller nations fending off larger foes.
    Guest Links:
    Manna https://www.manna.aero
    Bobby Healy https://www.linkedin.com/in/bhealy/
    Manna funding announcement https://www.manna.aero/blog/series-b
    Theseus https://www.theseus.us/
    Ian Laffey https://www.linkedin.com/in/ilaffey2/
    Most recent Theseus funding announcement https://techcrunch.com/2025/04/17/defense-tech-theseus-landed-y-combinator-the-us-special-forces-and-4-3m-from-a-tweet/
    The tweet that kickstarted Theseus: https://x.com/ilaffey2/status/1759353732075294766

    Timestamps:
    0:00 Bobby Healy of Manna joins TWiST
    1:41 How a Manna base works: drones migrate around the city like Waymos
    7:18 Battle-hardened in Irish weather: 97% uptime in wind and rain
    8:52 Margin-positive economics & the path to $0.20 per delivery
    9:25 Northwest Registered Agent: Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist
    12:32 $50M Series B vs competitors raising $600–800M
    19:51 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.
    22:53 The peer-to-peer drone future and hyper-local commerce
    25:46 Growing from 170 to 570 people and moving manufacturing to Oklahoma
    28:43 Ian Laffey of Theseus joins TWIST
    29:57 Render: Find out why 5 million developers are already using the all-in-one cloud platform, Render. Go to https://render.com/twist and apply for the Render Startup Program to get $500-$100,000 in free credits, depending on your stage and backers.
    30:58 Inside Ukraine's drone industry: front-line iteration and free-market speed
    33:55 How GPS gets jammed across the spectrum
    35:10 Theseus's approach: cameras + satellite maps + ML
    37:04 The product: Raspberry Pi, SD card, camera — pretending to be GPS
    49:02 Ukraine: 6–8M drones a year. The US: 300K over two years.
    51:17 Are US drone primes actually reconstituting the supply chain?
    58:22 Y Combinator as a defense tech accelerator
    59:40 "Pick an issue and start working as hard as you can towards it"
    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
    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
    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
  • This Week in Startups

    From hypercars to cruise missiles: Lukas Czinger on the future of US defense | E2292

    2026/05/23 | 1h 47 mins.
    This Week In Startups is made possible by:

    Every.io https://every.io
    Shopify https://shopify.com/twist
    Render https://render.com/twist
    Plaud https://Plaud.ai/twist

    Today’s show:

    Startups like Divergent Technologies are producing components and aircraft for the military through new systems that are better, faster, and cheaper than conventional methods. CEO and co-founder Lukas Czinger stops by TWiST to share the company’s vertically integrated, AI-driven manufacturing platform and how he transitioned from hypercar parts to working directly with the Pentagon on autonomous aircraft.
    Plus, 50 million Americans are on antidepressants, and it’s not necessarily the right treatment for all of them. Outro Health co-founders Brandon Goode and Dr. Mark Horowitz share their hyperbolic tapering method, which helps patients get off drugs like Zoloft and Prozac without suffering through traumatic and potentially dangerous side effects.

    Guests

    Lukas Czinger: https://x.com/lukasczinger
    Divergent Technologies: https://www.divergent3d.com
    Czinger Vehicles: https://www.czinger.com/
    Brandon Goode: https://www.linkedin.com/in/goodebrandon/
    Dr. Mark Horowitz: https://x.com/markhoro
    Outro Health: https://outro.com

    Timestamps:
    0:00 Divergent shifted from hypercar development to 3D printing all kinds of components
    1:33 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
    4:10 How 3D printing has exponentially improved
    8:18 Making military components faster, better, and cheaper
    9:58 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io
    11:00 How Divergent caught the Pentagon's attention
    19:51 Shopify - Turn those What Ifs into sales with the ecommerce platform powering millions of businesses. Sign up for your $1-per-month trial today at https://shopify.com/twist
    25:29 Why Outro Health helps patients taper off SSRIs
    30:06 Render - Find out why 5 million developers are already using the all-in-one cloud platform, Render. Go to https://render.com/twist and apply for the Render Startup Program to get $500-$100,000 in free credits, depending on your stage and backers.
    36:37 Is depression caused by a "chemical imbalance"?
    46:37 Understanding the hyperbolic tapering method
    58:32 How Outro makes money
    1:10:01 Leaked Meta layoff audio
    1:13:41 Cloudflare CEO drops "measurer" roles
    1:18:16 CrowdHealth - CrowdHealth lets you ditch the bureaucracy with a peer-to-peer funding platform for your healthcare. Get started for $99 per month for your first three months by using the code TWIST at https://JoinCrowdHealth.com/twist.
    1:19:17 Why Trump canceled his AI executive order
    1:28:08 Polymarket sharps on Russia vs. Ukraine, SpaceX ticker symbol
    1:33:34 Luel vs. Kled update: Is this nepotism at work?
    1:37:02 Chris Nolan doesn't have a smartphone
    1:43:04 Jason's favorite new espresso machine
    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
    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
    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
  • This Week in Startups

    Avi Patel on the startup that copied Kled and why he called out General Catalyst by name | E2291

    2026/05/20 | 1h 34 mins.
    This Week In Startups is made possible by:
    Grasshopper Bank - https://grasshopper.bank/twist
    LinkedIn - https://linkedIn.com/twist
    Northwest Registered Agent - https://northwestregisteredagent.com/twistPlaud - https://Plaud.ai/twist 
    Why raise $200 million if you are already profitable? That’s the question Jason and Alex put to Mercury’s founder and CEO, Immad Akhund, after the entrepreneur raised another massive round for his upstart, technology-friendly bank. TWiST then welcomed Kled founder Avi Patel to discuss the startup he considers a clear ripoff of his own company. Jason gavels in verdicts on all parties involved, including Y Combinator and venture capital firm General Catalyst. The show closes with a news lightning round, including OpenAI’s decision to offer $2 million in token credits to hundreds of startups.
    Guest Links:
    Mercury https://mercury.com
    Mercury funding announcement https://www.businesswire.com/news/home/20260520511817/en/Mercury-Raises-$200-Million-Series-D-at-$5.2B-Valuation
    Immad Akhund on X https://x.com/immad
    Kled https://www.kled.ai/
    Avi Patel on X https://x.com/avipat_/
    Avi’s complaint https://x.com/avipat_/status/2055384102409253056
    General Catalyst https://www.generalcatalyst.com/
    Y Combinator https://www.ycombinator.com/
    Delve https://techcrunch.com/2026/04/23/another-customer-of-troubled-startup-delve-suffered-a-big-security-incident/
    Discussion links:
    Anthropic’s attack on secondary trading https://techcrunch.com/2026/05/12/anthropic-warns-investors-against-secondary-platforms-offering-access-to-its-shares/
    Vanta https://www.vanta.com/twist

    Timestamps:
    0:00 Welcome to This Week in Startups!
    2:14 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
    3:27 Immad Akhund (Mercury) joins to discuss $200M raise
    6:33 Mercury's origin story and path to $650M run rate
    9:53 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist
    14:23 Stablecoins: where they work, why Mercury won't launch its own
    20:13 LinkedIn - Thanks to our partners at LinkedIn! Post your job for free at https://linkedIn.com/twist then promote it to get access to LinkedIn Jobs' new AI assistant.
    22:38 AI agents, and the future of money movement
    27:30 Why Mercury raised less this round
    30:11 Grasshopper Bank - Time is money. Don't waste either. Go to https://grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account.
    42:48 Avi Patel (Kled) joins to discuss copycat startups
    57:06 Jason's verdict on YC's hacker culture & "appearance of impropriety"
    1:17:39 Sam Altman's $2M-in-tokens-for-equity offer to YC founders
    1:24:32 NYC hotel housekeepers cross $100K in time under new union contract
    1:30:14 Minimum wage, immigration & the case for raising it slowly
    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
    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
    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
  • This Week in Startups

    Why does Gen Z hate AI?

    2026/05/18 | 1h 8 mins.
    This Week In Startups is made possible by:
    Vanta - Vanta.com/TWIST
    Sentry - Sentry.io/TWIST
    Deel - Deel.com/TWIST
    Today’s show:
    AI is the villain of the 2026 commencement cycle, with business luminaries — including Eric Schmidt — booed for discussing or praising the technology. As students graduate into a job market forcibly reshaped by AI, increasingly negative public polling on the potential impacts of artificial intelligence on society is clearly not missing the mark.
    Jason and Alex then discussed The Information’s reporting that Anthropic and OpenAI earn nearly 90% of all startup AI revenue, a Stanford student’s viral essay regarding their time at the university in a post-ChatGPT world, Flock Safety’s impressive (and worrying) web of cameras, and the upcoming Mark II AI bookmark. The episode closes with questions from our live audience!

    TWIST Links:
    Bounty website https://www.thisweekinstartups.com/bounty
    Sidebar bounty challenge https://www.notion.so/launch1/5K-Bounty-Create-Sidebar-App-for-Podcasts-34150ff313d280adbd8ed6204676513c
    Annotated.com bounty challenge https://annotated.lovable.app/
    Timestamps:
    0:00 TWiST All-Stars summer lineup announcement
    2:43 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
    5:08 Eric Schmidt booed at University of Arizona commencement
    8:57 Why Gen Z feels "double-crossed" by AI leaders
    10:10 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.
    15:22 Is this AI's Vietnam moment? The anti-war parallel
    18:04 Theo Baker's NYT essay on Stanford's AI cheating culture
    19:24 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST
    22:30 Why Jason says everyone should start a company
    28:59 Anthropic + OpenAI capture 89% of AI startup revenue
    30:17 Vanta: Get $1000 off your SOC 2 at https://www.vanta.com/twist
    31:57 Are token sales a duopoly? Negative gross margins debate
    35:17 Risk of building app-layer startups on top of foundation models
    38:22 Inside Tracker bounty update: AI sidebar + Annotated.com
    41:18 Mark II: the $159 AI bookmark Alex wants
    49:31 Flock Safety solves Austin shooting via Manor PD
    53:39 DeFlock map and the geography of surveillance in Texas
    1:03:42 Noti Gang: AI for filing patents
    1:05:45 Noti Gang: Running AI models locally on Mac Studios
    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 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
    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
    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
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About This Week in Startups
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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