This Week in Startups

• What’s REALLY going on with those “ads” in ChatGPT | E2220

  This Week In Startups is made possible by:Superhuman - https://superhuman.com/PODCASTSquarespace - https://squarespace.com/twistEnterpret - https://www.enterpret.com/dlp/this-week-in-startupsToday’s show: A screenshot showing a “Target Ad” in ChatGPT results went viral… over the weekend, but the OpenAI chatbot has NOT actually opened the advertising floodgates just yet.As ChatGPT staffers were quick to explain on social media, this was actually an invitation for a user to integrate their Target account into ChatGPT, for an easier agentic browsing and shopping experience.But it does prompt Jason and Alex to ask some intriguing questions… Is OpenAI just waiting for Google or someone else to launch AI ads first, and face the inevitable flood of backlash they’ll presumably receive? Is there someone at OpenAI already thinking DEEPLY about how these in-feed ads should work? And what does this mean for their wager on when ChatGPT is going to actually get ads? Is that already decided?These answers and more are coming your way on today’s action-packed TWiST… PLUS the latest on the Warner Bros Discovery-Netflix deal, PR guru Lulu Cheng Meservey’s new venture fund, and why Jason and Lon are obsessing about Apple TV’s “Pluribius.”Timestamps:(01:59) They put Target ads in ChatGPT? Or was it just an integration? Is there a difference?(5:24) Is someone at OpenAI really thinking deeply about how in-feed ads should work?(07:36) Is OpenAI just waiting for Google to start running ads to post their own? Jason has suspicions…(10:01) Why Jason thinks startup people have so much trouble communicating with normies(10:32) Superhuman - Get AI that works where you work. Unlock your Superhuman potential at https://superhuman.com/PODCAST(13:22) The insane competition now facing down OpenAI and Sam Altman(18:40) Why Jason will no longer use data from SaaS companies looking for a marketing win(19:52) Does this mean ChatGPT TECHNICALLY has ads? Does Alex win the bet?! What does Polymarket think?(20:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist(25:17) Why Jason is already tired of the Netflix-Paramount-WBD story(30:06) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to http://Enterpret.com/twist to book a demo and see it in action.(34:03) President Jason’s new proposal: A 60-day “pre-approval” antitrust window(47:29) Why Jason’s not interested in news commentary… just the facts.(51:40) Jason and Lon take a few moments to praise “Pluribus”(54:45) PR guru Lulu Cheng Meservey is starting a venture firm… here’s why she wants to start a “movement”(58:05) Why PR people hate but also respect JasonSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/Check out the TWIST500: https://twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelm/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis/*Thank you to our partners:(10:32) Superhuman - Get AI that works where you work. Unlock your Superhuman potential at https://superhuman.com/PODCAST(20:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist(30:06) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to http://Enterpret.com/twist to book a demo and see it in action.

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• Netflix buys WB + why Jason should run Disney | E2219

  This Week In Startups is made possible by:Sentry - http://sentry.io/twistLinkedIn Ads - http://linkedin.com/thisweekinstartupsPipedrive - pipedrive.com/twistToday’s show:Netflix wants to gobble up Warner Bros. Do they just want to own Batman and Harry Potter, or is this secretly about destroying movie theaters?Sure, this is usually a startup show, but news THIS BIG warrants attention! So Lon stops by to tell Jason and Alex about the big Netflix acquisition news, why so many theatrical movie fans are terrified for the future, and why this might face particular regulatory scrutiny both at home and abroad.PLUS… are Googlers gaming Polymarket? This is one scenario in which prediction markets are NOT exactly like stocks.THEN we’re looking at some of our favorite startups from the Fall ‘25 Y Combinator cohort (and asking Producer Claude for his picks)… Considering why Perplexity keeps getting sued and how they can stop it… and doing a victory lap for Jason’s early investment in breakout AI training project Micro1.Timestamps:(02:05) Netflix buying Warner Bros! Jason, Lon and Alex react.(05:04) Jaytrade Update: J kind of missed the boat on this one(05:36) What does this mean for theatrical cinema?(08:42) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(09:52) Jason’s pitch to Disney CEO Bob Iger (please send this to him!)(19:36) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.(23:29) Is this deal going to get approval, at home and abroad?(25:52) Are Googlers gaming Polymarket?(28:02) Can you do “insider trading” on a prediction market?(29:23) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at pipedrive.com/twist(37:00) How accelerators like Y Combinator serve as “finishing schools” for startups(37:52) A Quick Look at some of our fav companies from YC’s Fall ’25 cohort(39:01) Why startups need to “skate to where the puck is going”(40:08) Why sometimes old ideas (like solar-powered aircraft) are often worth revisiting(45:29) Jason’s advice for founders (and investors) in the “feel good” or activist space(50:48) Why Lon, Alex, and Claude ALL thought Hyperspell sounds like a hot startup(52:58) Perplexity getting sued again! Why can’t they make friends!(57:51) Meanwhile, Meta’s signing AI deals with news publications.(59:21) Micro1, which Jason helped to fund, has hit $100M ARR! Why do AI companies need so many experts?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 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:(8:42) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(19:36) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.(29:23) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at pipedrive.com/twist

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• Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218

  This Week In Startups is made possible by:Northwest Registered Agent - https://www.northwestregisteredagent.com/twistCrusoe - http://crusoe.ai/buildGusto - https://www.gusto.com/twistToday’s show: Delegating is its own unique skill, requiring training and a real investment of time and attention.On TWiST, Jason chats for a full hour with the founder of one of his favorite startups, Athena, which trains online assistants and pairs them with busy founders and executives. (Jason has 2!) But getting the MOST out of your executive assistants is less obvious than it looks. Jonathan unpacks some of the secrets to “Black Diamond Delegating,” and how he manages to keep 6 different high-level helpers operating at once.Plus, Jason and Jonathan look back at the Open Angel Forum days, where Jason invested in Jonathan’s previous company, Thumbtack, praise the “Checklist Manifesto,” discuss the telltale signs you’ve achieved market pull, and lots more insights.Timestamps:(01:53) We’re joined by Jonathan Swanson from one of JCal’s fav startups, Athena!(02:02) Jason and Jonathan first met during the Open Angel Forum, when Jonathan was working on Thumbtack(06:44) Finding the “little touches” that can help make an app more delightful(9:47) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(12:05) The shift from Thumbtack to Athena was all about time(12:52) How Jonathan delegates to 6 exec assistants at once(14:22) Pricing Athena’s EAs: Jason runs the numbers(15:09) Why Athena made Jason believe in hiring assistants again(18:15) Getting past the “Cardinal Sins of Delegation”(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(20:48) Will AI ever be able to replace Athena assistants?(23:41) Inside how Athena finds and trains assistants from around the world(27:01) How JCal became an Athena Ambassador… and almost crashed the system!(30:55) Gusto - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at https://www.gusto.com/twist(32:11) The magic of having assistants work on “backstop projects” and creative tasks(37:14) How to know when you have achieved market pull(40:05) Why getting the most out of delegating takes real investment and training(44:36) More praise for the Checklist Manifesto(46:26) Jonathan gives us a peek at what “Black Diamond Delegation” looks like(52:14) Jason’s early experiences hiring overseas assistants, from the Mahalo days*Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelm/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis/*Thank you to our partners:(9:47) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(30:55) Gusto - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at https://www.gusto.com/twist

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• Monumental Makes Construction Bots Play Nice Together | E2217

  This Week In Startups is made possible by:LinkedIn Ads - http://linkedin.com/thisweekinstartupsVanta - https://www.vanta.com/twistPilot - https://pilot.com/twistToday’s show: Did you know there’s actually a shortage of US bricklayers? It’s TRUE! So feel free to marvel at Monumental’s brick-laying robots. They’re not putting anyone out of work, but filling a much-needed gap.Join Alex and Monumental founder/CEO Salar al Khafaji for a deep-dive on how the startup is making construction robots play nice together by maintaining separate “zones” of operation, why Salar thinks startups need to focus on truly complex, real-world problems to truly blossom, and the secrets of fundraising in Europe.PLUS Alex chats with Seasats CEO Mike Flanigan about designing the next generation of autonomous marine crafts. (That is to say, ocean drones.) From their home base in San Diego, the company is trying to get completely independent of all Chinese parts. Find out how it’s going, how they’re overcoming the “wildly negative” ROI on maritime tech, and why we have so few defenses against tiny, agile drones.All that AND Jason takes some of YOUR Founder Questions.Timestamps:(03:23) How Monumental determined what kinds of robots construction sites need the most(06:49) How maintaining “zones” ensure that the robots all play nice with one another(07:52) There’s a shortage of bricklayers, so Monumental’s NOT taking anyone’s job(9:16) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.(13:21) Why startups need to tackle large-scale, complex, real-world problems to really grow(15:44) Why Monumental is building in The Netherlands, and running pilots in the UK(19:07) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(20:44) Why construction is unique among applications for automation and robots(26:01) Salar argues that fundraising in Europe is not as hard as you may have heard(27:55) We don’t just need housing, we need BEAUTIFUL housing(31:11) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year. (33:25) How the Scout autonomous boat challenge inspired Seasats(35:28) Trying to make drones into an “iPhone Style” project(37:39) Why Seasats is focused on endurance and staying power more than launches(39:15) The complexities of working with fuel cells(42:27) The importance of beautiful design even when working on government technology(45:51) Why they’re building Seasats in beautiful San Diego, CA(47:29) The challenge of getting entirely free from Chinese components(53:52) “The Power of Small Things Has Changed”(55:18) The “wildly negative” ROI on most humanoid robotics companies also applies to maritime tech(59:09) Why there are so few defense nets against people with tiny but agile drones(01:02:32) FOUNDER Q’s: Is a founder working 24/7 a red flag?(01:10:11) How bad is it to use VC money to pay off credit cards?(01:12:49) A look at Cursor’s unique recruitment strategy.(01:19:57) Should young VCs go to startup conferences?Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/Check out the TWIST500: https://twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelm/*Thank you to our partners:(9:16) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.(19:07) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(31:11) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

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• Is $MSTR over? Jason takes his victory lap. | E2216

  This Week In Startups is made possible by:Quo - http://quo.com/TWiSTSquarespace - https://www.Squarespace.com/TWISTMiro - http://miro.com/Today’s show: Michael Saylor’s Strategy play is struggling with the price of Bitcoin on a steep decline… Is his new “dollar reserve” the answer?On TWiST, we’re looking into the state of $MSTR and why Jason remains SO skeptical about this increasingly convoluted financial scheme.Is CNBC giving Michael Saylor a pass? Is that why he won’t go on “All-In”? And do investors realize that loans go BEFORE equity? We’re asking the TOUGH questions…PLUS Jason’s Four Red Flags for companies with convoluted tactics… Why S&P Global downgraded Tether, and why Jason thinks the US government waited TOO LONG to pass stablecoin regulations… Jason reacts to the NYT “hit piece” on Bestie David Sacks… we’re checking out the new Matic robot vacuum and Sunday Robotics’ Memo bot… PLUS much more of the day’s biggest tech news and stories.Timestamps:(03:04) Why Jason broke his “No Demo Day” rule for the LAUNCH 35 Accelerator(07:08) What we can learn from BitcoinTreasuries.net about the marketplace(07:42) Why Jason remains SO skeptical on $MSTR… and any sufficiently convoluted financial scheme…(7:56) Jason’s Four Red Flags for rogue companies and financial schemes(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST(14:31) When loans go before equity, and how this can dilute your investment!(18:05) Is CNBC giving Michael Saylor a pass? Why Jason thinks he won’t go on “All-In.”(19:30) Checking in with Polymarket’s thoughts on potential MicroStrategy Bitcoin sales(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist(22:58) Speaking of complex schemes… why S&P Global downgraded Tether(29:26) Is Tether too good to be true, as an investment?(25:17) Why Jason thinks the US waited too long to pass stablecoin regulations.(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!(36:15) Jason’s reaction to the NYT piece about Bestie David Sacks(43:14) Is there a growing divide within the GOP about how to engage with tech companies?(44:04) What are “Glue Employees” and why are they important?(45:03) How to tell your “Glue Employees” apart from the “union reps” and other rabble rousers…(51:50) Sunday Robotics: another human-ish robot but with WHEELS (and a baseball cap)(56:05) We’re checking out the Matic robot vacuum as well… Should these products be combined?*Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/Check out the TWIST500: https://twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelm/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis/*Thank you to our partners:(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!Great TWIST interviews: Will Guidarahttps://youtu.be/pvJa2pzuXWQEoghan McCabehttps://youtu.be/9dHN4YFkgv4Steve Huffmanhttps://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424Brian Cheskyhttps://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112

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