This Week in Startups

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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
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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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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
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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
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Self-driving just stopped being a science problem and became an engineering challenge instead. That's the through-line of today’s double-header with the CEOs of two of the most important AV companies in the world — Wayve's Alex Kendall and Waabi's Raquel Urtasun. Between them: ~$2B raised in the last six months, Uber as a partner, Nissan and Volvo as OEMs, and a shared bet that end-to-end AI plus world models beats Waymo's city-by-city map-and-pray approach.
If you want to understand the state of the self-driving industry beyond recent Waymo announcements, this is the episode for you.
Guest Links:
Wayve: wayve.ai/
Waabi: http://waabi.ai/
Alex Kendall https://www.linkedin.com/in/alexgkendall/
Raquel Uratsun: https://www.linkedin.com/in/raquel-urtasun-298400139/
Company Links:
Wayve’s GAIA-2 world model: https://wayve.ai/thinking/gaia-2/
Wayve’s 500 city roadshow: https://wayve.ai/thinking/ai-500-roadshow-500-cities/
Wavye’s most recent funding round: https://wayve.ai/press/series-d/
Waybe + Uber: https://wayve.ai/press/wayve-nissan-uber-robotaxi-collaboration/
Waabi closed-loop simulator: https://waabi.ai/insights/waabi-world
Waabi + Volvo: https://waabi.ai/insights/waabi-and-volvo-autonomous-solutions-partner-to-jointly-develop-and-deploy-autonomous-transportation-solutions
Waabi + Uber: https://www.uberfreight.com/en-US/blog/uber-freight-and-waabi-introduce-industry-first-autonomous-truck-deployment-solution

Timestamps:
0:00 Alex Kendall (Wayve) joins the show
1:19 The contrarian bet on end-to-end AI and world models in 2017
3:05 What is a world model? GAIA-2 and GAIA-3 explained
7:34 Sensor agnosticism: camera, radar, LiDAR and minimum bar for safety
9:56 $1.5B raised — have we cracked self-driving?
10:09 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.
20:38 Squarespace: Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST
25:03 How consumers will actually pay: bundle, subscription, or free trial
30:15 IM8 Health: Start feeling like your best self every day. Go to https://IM8health.com/twist and use the code TWiST to get a free welcome kit, five free travel sachets, and 10% off your order.
35:59 Raquel Urtasun (Waabi) joins the show
36:25 World models as controllable simulators for physical AI
43:34 One AI brain across trucks, robotaxis, and beyond
47:35 What changed in AI to make 2026 the deployment year
52:28 Why Waabi raised $1B when they're capital-efficient
58:52 Where Waabi is today: Volvo VNL Autonomous, Dallas-Houston, Uber Freight
1:00:50 Per-mile pricing and the Driver-as-a-Service model
1:07:20 Has Uber tried to buy Waabi? "Not for sale"

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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
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This Week In Startups is made possible by:Pilot -⁠ https://Pilot.com/TWIST⁠Grasshopper Bank -⁠ https://Grasshopper.bank/TWIST⁠Quo -⁠ https://Quo.com/TWiST⁠Plaud - ⁠https://Plaud.ai/twist⁠Anthropic just declared every unauthorized secondary sale of its stock "void" — naming Hiive, Forge, Sydecar, Upmarket, and others in a public hit list. Jason and Alex sit down with Jenny Fielding (Everywhere Ventures), Dave McClure (Practical VC), and Sam Lessin (Slow Ventures) to unpack what the AI lab’s move to limit secondary trades means for SPV operators, brokers, and the founders trying to keep control of their cap tables. Plus: a real story of a founder who returned a $15M Series A six months after closing because Claude was going to eat his startup, SaaS moats, and just what does it mean to be rich?Timestamps:0:00 Guest introductions0:48 Anthropic voids unauthorized SPV trades8:41 Accredited investor reform & the SEC sophisticated investor test8:58 Quo (formerly OpenPhone) - Quo gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at https://quo.com/TWiST11:43 Naval's USVC closed-end fund as a workaround16:41 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!17:48 Pro-rata rights battles: when Series A investors push seed investors out19:36 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.29:13 Pilot: Focus on your product, let Pilot handle your bookkeeping. Pilot provides the most reliable accounting, CFO, and tax services for startups and small businesses. Head to https://pilot.com/twist and get $1,200 off your first year.30:23 Storing wealth in stories vs. cash flows34:19 Cerebras and Fervo Energy IPOs — meaningful liquidity?37:54 Will SpaceX, Anthropic, OpenAI IPOs redistribute capital or compound it?45:58 The $15M Series A founder who returned the money because of Claude50:01 Should founders pivot or return capital when the world changes?56:43 OpenAI's $6.6B tender and Shruti Gandhi's viral SF cost-of-living tweet1:00:25 Intercom rebrands to Fin: the AI-first late-stage pivotSubscribe to the TWiST500 newsletter:⁠ https://ticker.thisweekinstartups.com⁠Check out the TWIST500:⁠ https://www.twist500.com⁠Subscribe to This Week in Startups on Apple:⁠ https://rb.gy/v19fcp⁠Follow Lon:X:⁠ https://x.com/lons⁠Follow Alex:X:⁠ https://x.com/alex⁠LinkedIn:⁠ ⁠https://www.linkedin.com/in/alexwilhelm⁠Follow Jason:X:⁠ https://twitter.com/Jason⁠LinkedIn:⁠ https://www.linkedin.com/in/jasoncalacanis⁠Check 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 McFarland⁠Check out Jason’s suite of newsletters:⁠ https://substack.com/@calacanis⁠Follow TWiST:Twitter:⁠ https://twitter.com/TWiStartups⁠YouTube:⁠ https://www.youtube.com/thisweekin⁠Instagram:⁠ https://www.instagram.com/thisweekinstartups⁠TikTok:⁠ https://www.tiktok.com/@thisweekinstartups⁠Substack:⁠ https://twistartups.substack.com⁠

The future of AI isn't a smarter chatbot. It's a model that watches your screen, listens to the room, and acts on what it sees. We dug into Thinking Machines' new interaction model, what it means for compute, and the layoff wave that's already here.This week's roundtable: Anastasios Angelopoulos (CEO of Arena, formerly LMArena), Nick Harris (CEO of Lightmatter, photonic computing chips), and Philip Johnston (CEO of StarCloud, building megawatt data centers in space).

Thank you to our exclusive sponsor:
PayPal Open, One Platform for All Business: http://paypalopen.com/

Timestamps:
0:00 Cold open
1:21 Welcome to Episode 13
2:51 Is China closing the AI gap? Arena's data
5:16 Lightmatter and the photonic interconnect bottleneck
9:42 StarCloud 2, Nvidia Space Ruben 1, and orbital data centers
17:24 Thinking Machines' interaction model: what's actually new
28:22 Whisper Flow and the 3-pedal desk setup
33:48 Real-time desktop and camera awareness as the real unlock
40:25 Why this 100x's compute demand
42:43 The polarization of compute and $10M personal data centers
49:25 The layoff wave: Cloudflare, PayPal, Coinbase, Upwork
54:48 The 10x gap between AI-first and non-AI-first employees
59:52 Unlimited agency and the abundance future
1:00:46 Anthropic's Project Luna runs a retail store
1:03:45 Decoupling labor from value creation
1:05:03 P(doom) round

🔗 Guests:
Anastasios Angelopoulos, Arena: https://arena.ai | @ML_Angelopolous
Nick Harris, Lightmatter: https://lightmatter.co
Philip Johnston, StarCloud: https://starcloud.com | @philipjohnston

🔗 Referenced in this episode:
Thinking Machines, Introducing Interaction Models: https://thinkingmachines.ai/blog/interaction-models/
LMArena leaderboard: https://lmarena.ai
Lightmatter: https://lightmatter.co
Starcloud: https://www.starcloud.com
TechCrunch, Cloudflare says AI made 1,100 jobs obsolete: https://techcrunch.com/2026/05/08/cloudflare-says-ai-made-1100-jobs-obsolete-even-as-revenue-hit-a-record-high/
Fast Company, Tech layoffs this week due to AI (Cloudflare, PayPal, Coinbase, Upwork): https://www.fastcompany.com/91538995/tech-layoffs-due-to-ai-this-week-cloudflare-paypal-coinbase-upwork
Bloomberg, South Korea floats citizen dividend from AI profits: https://www.bloomberg.com/news/newsletters/2026-05-12/korea-s-massive-ai-boom-triggers-call-for-tech-tax-roiling-market
PYMNTS, Inside a retail store run entirely by AI (Andon Labs / Luna): https://www.pymnts.com/artificial-intelligence-2/2026/inside-a-retail-store-run-entirely-by-ai/
Wispr Flow (voice-to-text tool Jason uses): https://wisprflow.ai
Fermi Paradox: https://en.wikipedia.org/wiki/Fermi_paradox

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