This Week in Startups

• All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158

  Today’s show:It’s another All Star Investor Panel! Jason and Alex welcome TrustFund VC founder Sophia Amoruso AND WeekendFund investor/Product Hunt founder Ryan Hoover.Together they’re going DEEP on the current environment for startups, founders, and investors. How do tell durable from brittle revenue… Everyone’s different approaches to follow-on investments and recycling… Strategies on when to trim a position… The benefits of hosting co-working events and jam sessions… And LOTS LOTS more!It’s an essential watch for anyone building or investing in companies in 2025!Timestamps:(0:00) Introducing our amazing investor panel!(03:15) The panel shares their First Fund experiences(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:27) Show cont…(12:46) Where we’re at on the investor Greed-Fear Index(13:54) The delicate art of investor discipline(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(21:59) Sophia’s criteria for a follow-on investment(24:17) Founders are going direct on social media(29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.(30:49) Show cont…(32:33) Why we’re seeing so many more Series Bs(33:30) So when do you trim a position?(39:35) There are SO MANY COMPANIES! Why surface area matters.(43:25) Durable vs. brittle revenue and how to tell them apart(46:15) When it’s time to angel invest outside your fund(49:04) The panel’s approaches to capital recycling(57:15) The benefits of co-working “jam sessions”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:(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.DISCLAIMER*All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.Rate as of 7/18/25. APY is variable and subject to change.Check 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/thisweekinstartups

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• Figma IPO, IMAX AI Festival, the Tea app spill, that one Sydney Sweeney jeans ad, and more! | E2157

  Today’s show:SYDNEY SWEENEY’S AMERICAN EAGLE AD DIVIDES OUR PANEL!PLUS WHAT STARTUPS CAN LEARN FROM THE VIRAL ASTRONOMER RESPONSEJason, Alex, and Lon are looking at some of the biggest media stories of the day before returning to their favorite topic, tech. Tune in for deep dives on IMAX’s new AI film festival, Figma’s big IPO and much more!*Timestamps:(0:00) Jason and Alex kick off the show!(3:45) Lon’s joining Alex and Lon to discuss the controversial Sydney Sweeney genes/jeans ad(7:20) A look at the polarizing takes on this jeans ad.(10:10) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠(11:46) Hear the verdict from Jason, self—proclaimed Chairman of the Interwebs(16:42) Alex points out the economic impact of the controversy(20:26) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(21:25) Back to the show!(26:35) Paltrow’s Astronomer ad, meme-processing and the ideal way to change the conversation(30:04) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist(31:28) Back to the show!(36:48) Netflix and the growing controversy around AI’s role in filmmaking(42:53) IMAX/Runway collaboration and Hollywood’s shifting attitude toward AI(47:34) Everything that went wrong with the Tea App(54:27) Why Jason thinks app stores should ban “anonymous” forms and message boards(1:04:19) Figma upped its IPO price… what does it mean for the return of liquidity? And is this too high or fairly priced?(1:07:53) Paul Graham says you shouldn’t drop out of college to work on a startup… Why Thiel Fellows disagree*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/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:(10:10) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠(20:26) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(30:04) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist*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/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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• Behind the scenes at the ALL-IN AI SUMMIT w/ POTUS, JD Vance, Jensen Huang, Lisa Su, and more… | E2156

  Today’s show:Jason’s back and filling us in on his experiences in Washington DC, at the All-In AI Summit, including getting a Trump shoutout from stage, debating immigration with VP Vance, and calling out Sec. Wright for dismissing solar power.THEN Jason and Alex talk about the immense promise of open-source robotics and check out Hugging Face’s Reachy…PLUS picking apart the White House’s new AI-related executive orders, why Jason is afraid of China repeating its Huawei success, a free exchange about tariffs vs. free trade, AND a pressing query from a founder on Reddit: how bad is it to add AI to your product too early?Timestamps:(0:00) INTRO, Alex updates Jason about all this week’s TWiST 500 interviews(03:33) Inside Jason’s experiences at this week’s All In AI Summit with POTUS!(05:33) Jason’s back and forth on solar power with US Energy Sec. Chris Wright(09:56) Inbound - Use code TWIST10 for 10% off your General Admission ticket at [https://www.inbound.com/register](https://www.inbound.com/register.) (Valid thru 7/31)(11:02) Promo end(16:54) Jason asks AMD CEO Lisa Su about reaching “superintelligence” and whether it could trigger an unemployment crisis(19:51) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.(20:44) Promo end(23:42) Jason says… any time you have to wait days or weeks for a service or product, there’s a MASSIVE opportunity.(26:16) What do Trump’s new AI executive orders actually say?(27:27) Which EO’s are red meat for Trump’s base, and which ones are likely to become laws and have real impact?(29:50) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at https://public.com/twist.(31:05) Promo end(35:17) How Huawei went worldwide and why Jason doesn’t want that to happen again with AI.(38:32) Jason and Alex have a little tariff vs. free trade debate.(47:03) VP Vance complained about US tech companies laying off Americans, then hiring immigrants; Jason gives his take(53:35) Jason answers a Reddit question: Is adding AI to your product too early a TRAP?Check out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpThank you to our partners:(09:56) Inbound - Use code TWIST10 for 10% off your General Admission ticket at [https://www.inbound.com/register](https://www.inbound.com/register.) (Valid thru 7/31)(19:51) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.(29:50) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at https://public.com/twist.*Disclaimer:All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.Rate as of 7/18/25. APY is variable and subject to change.

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• AUTOMATING HEALTH CARE, THERMODYNAMIC COMPUTING, AND PRODUCT VELOCITY | E2155

  Today’s show:TWiST is back with a three more hugely insightful (and also fun!) founder interviews.First up, Trey Holterman from Tennr tells us why getting in to see a specialist is so time consuming, and how AI is making the entire health care industry more streamlined.THEN Gill Verdon from Extropic AI unpacks deterministic vs. probabilistic computing, and how thermodynamics can make everything from robots to VR more effective.FINALLY, Tyler Denk from our fav newsletter platform Beehiiv walks us through their future roadmap, and explains why they’re adding new features SO OFTEN.It’s a packed episode full of fresh insights for founders. Check it out!Timestamps:(0:00) Alex opens the show with the venture/investor POV on TWiST 500 med tech company Tennr(03:38) Tennr CEO/co-founder Trey Holterman on the inefficiencies facing medical specialists and why patients are actually “leads”(10:20) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:44) Paid Promo END(14:05) How Tennr trained an AI model to comb through clinical histories, medical files, and doctor’s notes(18:19) Why automation matters for Tennr but it’s not the WHOLE story(20:03) 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!(21:10) Paid Promo END(22:57) The incredible cultural influence of the Dominos Pizza Tracker(29:57) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits(31:20) Gill Verdon from Extropic on the difficulty of keeping up with the demand for compute and the “scaling law”(35:37) Thermodynamic regimes, the differences between deterministic vs. probabilistic computing, and why this matters(41:31) Gill on expanding Extropic’s research team while keeping a close eye on burn(52:17) Will robots ever be FULLY autonomous, with no ties or connections back to the fleet? Gill says… maybe!(58:52) Beehiiv’s Tyler Denk on hitting $20M ARR while ALSO scaling up their ad network(01:00:35) The practical and psychological importance of product velocity and shipping as many features as possible(01:01:57) Why Tyler says “Substack vs. Beehiiv” is analogous to “Amazon vs. Shopify”(01:08:08) How much larger can the newsletter market still GROW? (And the promise of moving beyond content and into marketing emails.)(01:09:00) Why Tyler thinks the strongest publishers own their audience and distributionSubscribe 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:(10:20) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(20:03) 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!(29:57) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/creditsGreat 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/@calacanis

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• Manufacturing in the US, Building in Open Source… and more | E2154

  Today’s show:TWiST is back with a trio of can’t miss interviews with some of our favorite TWiST 500 founders.First up, John Harris of Harbinger Motors tells us about making his EV batteries right here in the USA, and why the loss of EV tax credits might not hurt the business as much as you’d think…THEN, we’re talking to James Hawkins of PostHog about how keeping his burn rate low opened up a wealth of new opportunities for his company…THEN Yoshi Yokokawa from Alpaca HQ stops by to talk about working in a category that’s no longer the hottest thing in the Valley (like fintech) and the importance of stable coins to his business model.You won’t want to miss this one! Tons of fresh and important insights for founders.Timestamps:(0:00) INTRO, The market’s hit an ALL TIME HIGH… what does it mean for founders and smaller companies?(2:19) Figma’s going IPO… how its success could impact other the entire landscape for the rest of the year.(10:12) Netsuite - Download the ebook Navigating Global Trade: 3 Insights for Leaders for free at https://www.netsuite.com/twist(11:29) Harbinger co-founder/CEO John Harris tells us about building EVs for commercial fleet, live FROM the factory(19:58) Retool - Visit https://www.retool.com/twist and try it out today.(21:15) Harbinger co-founder/CEO John Harris tells us about building EVs for commercial fleet, live FROM the factory (cont…)(30:07) .TECH: Say it without saying it. Head to www.get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(31:07) How much of Harbinger’s product is actually manufactured in the US (and why that’s a more complex question than it sounds) (31:39) Why the rollback of EV tax credits might NOT have a huge impact on Harbinger’s business.(36:53) James Hawkins of PostHog explains how and why Stripe funded their most recent round.(40:23) Will it soon be easier to build a virtual product manager than hire the right human person? MAYBE!(42:11) Why building PostHog as open source was so vital for boosting adoption among developers(47:45) Why James credits a low burn rate and being “multi-product” with PostHog’s success and traction(01:00:02) Alpaca CEO and co-founder Yoshi Yokokawa explains to us how the API brokerage infrastructure co. actually makes money(01:00:41) Why it matters that Alpaca is a “self-clearing market maker”: Yoshi unpacks how trades actually get executed(01:07:46) The massive impact of Robinhood on the entire fintech business and how this benefits Alpaca(01:18:06) Yoshi’s tips for founders working in categories that aren’t THE HOTTEST IN THE WORLD right nowSubscribe 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:(10:12) Netsuite - Download the ebook Navigating Global Trade: 3 Insights for Leaders for free at https://www.netsuite.com/twist(19:58) Retool - Visit https://www.retool.com/twist and try it out today.(30:07) .TECH: Say it without saying it. Head to www.get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.Check 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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