This Week in Startups

• Stripe’s Crypto Wallet, M&A Momentum, and Robots Replacing Soul-Crushing Jobs | E2138

  Today’s show:In this episode of This Week in Startups, @Jason and @Alex break down Stripe’s big bet on crypto wallets with its latest acquisition of Privy, the return of major M&A activity from Meta, DoorDash, and Stripe, and the rapid rise of robotics replacing soul-crushing warehouse jobs. They dive into why today’s toy-like robot arms will become tomorrow’s billion-dollar tools, how stablecoins are quietly transforming fintech, and why Disney is going to war with AI platforms over IP theft. A must-watch if you’re building, investing, or just trying to understand where tech is headed next.Timestamps:(1:48) Startup Tip: "Find a service you hate and make it better"(9:23) Why Stripe wants crypto wallet company Privy(10:09) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(15:46) Klarna: The New Rent-a-Center?(20:00) Superpower - Visit superpower.com/twist to get $50 off your membership. This offer is only for the first 100 twist listeners who sign up.(26:28) Why M&A is good and Lena Khan was wrong(30:00) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(33:20) Robots are going to make your life better(42:11) When toys become tools(46:25) Tesla's on-the-road FSD tests... do they need safety drivers?(54:13) Jason has the answer for all these AI copyright suitsSubscribe 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/jasoncalacanisThank you to our partners:(10:09) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(20:00) Superpower - Visit superpower.com/twist to get $50 off your membership. This offer is only for the first 100 twist listeners who sign up.(30:00) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  1:03:53
• TWIST VC Roundtable: Startup Valuations, Secondary Markets & the YC Revenue Illusion | E2137

  Today’s show: Alex moderates a TWIST VC Roundtable with Jason, Paige Doherty (Behind Genius), and Altimeter’s Megan Reynolds about the state of early-stage venture capital. They break down the rise of secondary markets as a key liquidity path for VCs, analyze the resurgence in M&A activity from major players like Meta, Databricks, and OpenAI, and question whether inflated ARR figures from YC startups are distorting valuations. Jason shares his year-zero investment thesis and offers tactical advice on secondary structuring and identifying high-quality revenue. Whether you're raising, investing, or building, this episode delivers essential insights into the evolving early-stage landscape.Timestamps:(0:00) Episode Teaser(1:28) Meet our panelists!(2:37) Will secondaries replace traditional M&A?(10:10) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(14:28) Has M&A actually bounced back?(20:06) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.(25:35) Secondary market advice, just for founders(30:10) Retool - Visit https://www.retool.com/twist and try it out today.(32:49) Why is it so hard for emerging managers to raise funds?(38:28) Seed funds: the math is not mathing(52:07) Why early investors become “collateral damage”(56:31) The importance of revenue quality in early-stage startups(1:06:43) Quick Fire Question Round!Subscribe 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/v19fcpLinks from episode:Altimeter: https://www.altimeter.com/homeBehind Genius: https://www.behindgeniusventures.com/Follow Meghan:X: https://x.com/MeghanKReynoldsLinkedIn: https://www.linkedin.com/in/meghankreynolds/Follow Paige:X: https://x.com/paigefinnnLinkedIn: https://www.linkedin.com/in/paigedoherty/Follow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(10:10) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(20:06) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.(30:10) Retool - Visit https://www.retool.com/twist and try it out today.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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  1:11:22
• YC Valuations, VC Slowdown, and Office Hours with CustomerIQ | E2136

  Today’s show: Jason and Alex dive into why Y Combinator startups are raising at sky-high valuations with relatively low ARR—what does that mean for investors and founders? VC funds are slowing down and returning to pre-ZIRP pacing, signaling a reset in the market. Plus, in this week’s Office Hours, Sean Steigerwald, founder of CustomerIQ, demos his AI sales agent that lives in your inbox, drafting follow-ups using CRM context. It’s a deep look at early-stage investing, startup efficiency, and where AI is headed in enterprise.Timestamps:(0:00) Episode Teaser(2:09) Jason's Singapore trip recap and SoCal update(9:51) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:40) New rumblings from Mistral; is the French AI startup catching a tail wind?(19:40) Fidelity Private Shares℠ - Visit ⁠https://fidelityprivateshares.com⁠! Mention our podcast and receive 20% off your first-year paid subscription.(26:23) VC investing pace is slowing... what does this mean for founders(29:42) INBOUND - Use code TWIST10 for 10% o your General Admission ticket at https://www.inbound.com/register (Valid thru 7/31)(33:33) Founders' guide to raising capital(36:31) Gen AI companies are growing FAST but are there concerns about churn?(42:46) Is YC still worth it? Debating paper gains vs. DPI as metrics.(52:18) Office Hours with Sean Steigerald from Customer IQ: managing active users and more.Subscribe 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/v19fcpLinks from episode:Customer IQ: https://www.getcustomeriq.com/Follow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(9:51) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(19:40) Fidelity Private Shares℠ - Visit ⁠https://fidelityprivateshares.com⁠! Mention our podcast and receive 20% off your first-year paid subscription.(29:42) INBOUND - Use code TWIST10 for 10% o your General Admission ticket at https://www.inbound.com/register (Valid thru 7/31)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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  1:03:55
• Circle’s IPO Soars, The Future of VC and Cursor’s Crazy Growth | E2135

  Today’s show: Jason and Alex dicuss stories shaping the tech and startup world: Circle’s explosive IPO and what it signals about crypto regulation and public market sentiment, the potential for tokenized venture capital funds to bring liquidity and transparency to startup investing, and Cursor’s extraordinary growth—scaling to over $500M in ARR in just six months.Timestamps:(0:00) Episode Teaser(2:25) Circle’s IPO is Soaring and What This Means for Tech(10:21) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(12:00) Is Tokenization the Future of Venture Capital?(20:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist(22:40) Oh, THAT’S Why Anthropic Cutoff Windsurf(27:06) Can the Rippling - Deel Saga Get Anymore Bizarre?(30:22) Sentry - New users get 3 months free of the Team plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(34:08) Cursor Just Keeps on Winning(43:10) Polymarket: What Will Jerome Powell Do?Subscribe 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 Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(10:21) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(20:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist(30:22) Sentry - New users get 3 months free of the Team plan (covers 150k errors). Go to http://sentry.io/twist and use code TWISTGreat 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  46:03
• Anthropic Cuts Off Windsurf, Deel Rewrites the Narrative and Flock Safety’s Surveillance Tech | E2134

  Today’s show: Alex and Lon discuss Windsurf getting abruptly cut off from Anthropic just before a rumored $3B acquisition by OpenAI, sparking questions around platform risk and foundation-model politics; Deel defends itself by arguing the information it allegedly took was public or obvious, complicating its ongoing legal saga; and Flock Safety’s neighborhood-focused surveillance tech—combining LPR cameras and drones—positions itself as a privacy-conscious tool that gives elected officials control over community data governance.Timestamps:(0:00) Episode Teaser(2:48) ADP's Employment Numbers Might Make Your Eyes Water(5:54) Is the Circle IPO Over Subscribed?(9:25) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(13:00) Anthropic Shows Sharp Elbows With Windsurf(19:55) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(20:57) Is It Really Stealing If It’s Public or Obvious? Deel Says No(29:23) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(30:50) The Space Future Alex Has Dreamed About(35:10) Anthropic Can’t Stop Scraping Reddit’s Data(42:44) Flock Safety is Bringing Surveillance To a Neighborhood Near YouSubscribe 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/v19fcpLinks from episode:Impulse Space: https://www.impulsespace.com/Flock Safety: https://www.flocksafety.com/Follow Garrett:X: https://x.com/glangleyLinkedIn: https://www.linkedin.com/in/glangley/Follow 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/jasoncalacanisThank you to our partners:(9:25) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(19:55) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(29:23) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  1:09:55

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