This Week in Startups

• Stop ghosting your friends with Nox’s RPLY, plus Alloy Automation and a Shopify flashback | E2209

  👉 Register here to join Founder University Japan’s kickoff: https://luma.com/cm0x90mkToday’s show:Nox’s new app RPLY reminds you to text your friends back, getting you to iMessage inbox zero.On today’s TWiST, we’ve got Molly Cantillon of Nox, telling us how she plans to make lackadaisical texters (like our co-host Alex) more effective, even if it means breaking into Apple’s walled garden. Hear about how RPLY maps your relationships so that it can understand your messages contextually, and help you stay organized.Then, Gregg Mojica of Alloy Automation swings by the show to dispel some common myths about AI agents. For the most part, these little machine learning helps aren’t truly autonomous… Hear how Alloy’s agents decide when it’s time to bring in a human for help. PLUS is AI in a “lull” right now? Hear why Gregg thinks there’s still a LOT of room for these apps to improve.Finally, it’s another TWiST Flashback. We’re jumping back to 2013 for an eye-opening chat between Jason and Shopify founder/CEO Tobi Lutke. Hear some fascinatingly prescient takes on the rise of SaaS, how early Shopify differentiated itself from other ecommerce and website building solutions, AND why Tobi dreamed of making Ottawa a true tech hub.Timestamps:(02:57) Molly Cantillon of Nox is trying to help you get better at texting(04:01) How RPLY gets even chaotic texters like Alex more organized(05:10) The complexities of entering into Apple’s “walled garden”(07:20) Keeping RPLY safe, in case you’re using it for work!(09:24) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!(11:59) How RPLY uses relationship mapping to understand and prioritize your messages(19:23) Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.(21:08) Why Nox wants its AI to become “the Invisible OS.”(29:30) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.(30:40) We’ve got Gregg Mojica of AI agent makers Alloy Automation(31:42) How the rise of AI agents changed the core of Gregg’s business(34:03) Why most AI agents still aren’t truly autonomous(35:00) How Alloy’s agents decide when to bring in a human for help(37:02) Why the rapid acceleration of AI development has made some enterprises pump the brakes(39:00) Is AI in a “lull” right now? Why Gregg thinks there’s still room to improve.(40:31) How close are we to AI apps going truly mainstream?(43:41) Why Alloy Automation didn’t raise a massive round like so many of its AI peers? (Or are they?!)(46:48) The difficulty of hiring in today’s AI landscape(50:21) In today’s TWiST Flashback, we’re revisiting Tobi Lutke of Shopify’s appearance from way back in 2013!(52:11) Why Shopify switched from selling snowboards to storefronts(59:37) Turning Ottawa into a tech hub, and the “secondary market” theory(1:05:32)The constant tension between growing your global footprint and expanding your features(1:08:52)Who were Shopify’s actual rivals?

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• Why We Need Ferries and Tugboats in Space w/ Orbital Operations | E2208

  👉 Register here to join the kickoff: https://luma.com/cm0x90mkToday’s show:Just getting our stuff into orbit isn’t enough… Orbital Operations wants to help companies take things HIGHER.In today’s TWiST 500 interview, Alex chats with Ben Schleuniger, whose startup Orbital Operations is solving the complexity of space logistics. The advent of reusable rockets has made it easier and cheaper than ever for us to place objects in Low Earth Orbit (or LEO).But what if we want to reach higher orbits? That’s a much more challenging issue: space is already kind of CROWDED, and not all of our vehicles can carry enough fuel to power them that far out into the cosmos.Orbital’s fix? Cryogenic orbital maneuvering vehicles (or OMVs) like the Astraeus, which uses hyper-efficient propulsion systems, allowing them to travel further and faster speeds, and even potentially get refueled in orbit.Learn more about this fascinating tech PLUS we’re looking back at classic Jason interviews with Greg Brockman of OpenAI and Vlad Tenev of Robinhood, AND checking in with Oliver’s latest This Week in AI demo for Character AI’s blockbuster conversational chatbots.Timestamps:(02:56) Alex opens the show with Ben Schleuniger, co-founder of space tech startup Orbital Operations(03:47) Why is movement within orbit such a challenging problem?(4:28) The key importance of launch vehicle reusability(07:05) How Orbital’s Astreaus vehicle utilizes cryogenic propellants… and why(08:49) The secret to keeping those propellants cool(10:04) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(13:57) How Orbital is preparing for their Series A, and how they plan to spend the cash(20:37) 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!(28:09) TWiST FLASHBACK: Revisiting OpenAI Greg Brockman’s visit from 2018(31:31) 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.(37:57) How GPUs unlocked the AI revolution(35:02) Tackling early concerns about deepfakes(41:17) Looking ahead to the dawn of AGI(50:05) AI DEMO: Oliver stops by to walk us through Character AI’s key features(50:51) Watch as Oliver simulates a chat with former President Barack Obama(53:30) How to use ChatGPT to enhance your Character AI prompts(56:57) TWIST FLASHBACK with Robinhood’s Vlad Tenev from May 2017(57:14) Back then, Robinhood was valued at a mere $1.3 billion!(59:21) How Robinhood made financial transactions SO MUCH FASTER than they used to be(1:00:57) When Robinhood realized they had Product Market Fit… via Hacker News!(1:06:44) The magic of being better, faster, and cheaper(1:08:12) This segment was filmed BEFORE Robinhood offered crypto(1:11: 08) Jason’s Eagle Computer Speech and how to avoid “Taj Mahal Syndrome”Check 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/alexwilhelmThank you to our partners:Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTNorthwest 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!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.

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• Inside Harvey AI’s $8 billion AI lawyer app, PLUS How OpenRouter unites the LLMs | E2207

  Register for Founder University Japan’s Kickoff! https://luma.com/cm0x90mkToday’s show:Find out why AI is perfectly suited to legal tasks… despite being too fast for “billable hours”On today’s TWiST, Alex takes a deep dive into LLM Law with Harvey AI co-founder/president Gabe Pereyra. It turns out, much like software development, doing legal work relies on learning specialized language and sifting through a dense and expansive corpus of information… making it an IDEAL use case for LLMs.Buuuuut AI works so fast… the current structure of legal payments (billable hours) no longer applies. Find out how Harvey is working around these challenges — and what they plan to do if OpenAI decides to get into the legal game — in this fascinating interview.THEN, Alex chats with another AI visionary — OpenRouter co-founder and CEO Alex Atallah — who allows developers to plug and play all the major models into their applications. Find out why specialized LLMs trained for “resourcefulness” are coming into fashion… why benchmarks and evals have become so crucial to the industry… AND whether we’ll end up spending as much on AI inference as the human workers it’s replacing… in this essential discussion.PLUS Jason stops by for some more Founder Q’s!Timestamps:(0:00) Welcome back to TWiST!(1:32) Alex kicks off the show with Harvey AI co-founder and President Gabe Pereyra to talk about applying AI to the legal profession(4:52) How major international law firms (and their enterprise clients) fueled Harvey’s mega-growth(6:54) Why LLMs are perfectly suited for legal work(9:24) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.x and build next. Head to Enterpret.com/twist to book a demo and see it in action.(17:22) Looking ahead: expanding beyond the law.(20:42) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist(21:44) The problem: AI can’t charge “billable hours”… it’s too fast!(23:44) Will the major AI players like Google and OpenAI build their own version of this?(29:53) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(30:41) Alex welcomes OpenRouter co-founder and CEO Alex Atallah, whose rankings he loves and uses all the time(33:10) Why Alex says we’re seeing more specialized LLMs trained for more “resourcefulness”(36:05) How increased competition and diversification makes things tougher for developers(41:09) Alex suggests that new models are exciting for users, like product launches used to be(42:29) OK, let’s get into it… How does OpenRouter make money?(45:38) Understanding what kinds of training data the AI companies want the MOST(47:47) The important currency of evals and benchmarks(49:13) Why OpenRouter is ramping up its LLM recommendation engine(53:44) Will AI inference spend end up costing as much as the humans it’s replacing?(56:49) Time for a Founder Q! What should founders do about quick vibe-coded competitors?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/alexwilhelmThank you to our partners:(9:24) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.x and build next. Head to Enterpret.com/twist to book a demo and see it in action.(20:42) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist(29:53) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

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• IPO Mania hits the TWiST 500! Three companies are ready to go public | E2206

  👉 Register here for Founder University Japan’s Kickoff! https://luma.com/cm0x90mkToday’s show:*Three of our favorite TWiST 500 startups — Ledger, 1Password, AND Mercury — are circling IPOs. Find out why the cybersecurity space remains so hot… AND why Jason says you really need to have multiple banks.PLUS Marc Andreessen called The Pope an AI Doomer on X, then thought better of it. We’re tracking the entire viral controversy…SPEAKING OF viral feuds, allegations are FLYING around about recently-funded AI agent makers Giga. Does the startup pose some genuine red flags, or was it just a questionable launch video?AND why Alex and Jason remain optimistic the AI vibes could turn around, presentation maker Gamma is growing FAST, plus an update on Jason and Alex’s Polymarket IPO wager…Timestamps:(02:17) Jason is hosting the big show from Tokyo today (tonight for him)… Where is Founder U headed next?(04:03) Jason’s eating his way across Japan… what are his top “bang bangs” so far?(07:47) Is The Pope a Doomer? Why Andreessen called out His Holiness (then deleted it)(9:22) Quo - Streamline and scale your customer communications with OpenPhone. Get started free, plus get 20% off your first 6 months, at http://quo.com/TWiST(12:08)Why Jason still thinks mass AI job displacement is coming(17:48) Will AI-related job loss lead to an explosion in startups and small businesses?(19:24) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist(20:39) Have lots of Americans suddenly turned on AI Why?(25:30) Why Alex and Jason remain optimistic that the AI vibes could turn around(29:44) 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 Gusto.com/twist.(31:01) Alex’s new favorite definition of Product Market Fit, or “Market Pull,” as Jason clarifies(33:31) Delving into the Giga controversy… “ugly” talk, wild X allegations, etc.(46:11) THREE TWiST 500 are readying IPOs… Catching up with Ledger, 1Password, and Mercury(53:42) Why Jason and Alex think you need multiple banks(57:40) Why presentation maker Gamma is growing even faster than we thought!(1:00:37) Checking in with Jason and Alex’s Polymarket IPO bet…(1:03:44) Could startups become so richly valued that they become “uninvestable” without an IPO?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:(9:22) Quo - Streamline and scale your customer communications with OpenPhone. Get started free, plus get 20% off your first 6 months, at http://quo.com/TWiST(19:24) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist(29:44) 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 Gusto.com/twist.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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• It’s a boat, it’s a plane, it’s REGENT’s Seafarer | E2205

  Register for Founder University Japan’s Kickoff: https://luma.com/cm0x90mkToday’s show:*The key to avoiding long airport delays? Low-altitude sea planes! Why didn’t you think of that?We’ve got an awesome line-up of TWiST 500 founders giving us an inside glimpse inside their startups on this Friday special edition.FIRST: Billy Thalheimer of REGENT introduces us to their aircraft/boat hybrid The Seaglider, and walk us through how it all works, AND why they’re operating in BOTH the commercial and defense sectors from their Rhode Island HQ.THEN, we’ve got Convexia co-founder Ayaan Parekh showcasing how they’re using a collective of specialist AI agents to exploit other pharma labs’ leftovers and turn them into new drugs and treatments for rare diseases.FINALLY, Hunter Leath of Archil joins the show to tell us why efficient utilization of cloud data remains a surprisingly complex, and unsolved problem. His solution? Caching-as-a-Service! Find out how it all works, and why pre-caching is SO difficult to do, in this TWiST exclusive chat.Timestamps:(03:01) Billy Thalheimer of REGENT introduces us to the Seaglider(05:06) Inside the EV aircraft/boat hybrid’s three modes of operation(08:22) How REGENT uses low altitude flight to avoid airport-related hassles(9:42) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to ⁠http://sentry.io/twist⁠ and use code TWIST(13:57) The converging tech that makes Seaglider possible(18:20) How REGENT is operating in BOTH the commercial and defense sectors(19:39) 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.(25:05) Why Rhode Island?!(29:23) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at ⁠https://pipedrive.com/twist⁠(31:04) Convexia co-founder Ayan Parekh joins Alex to discuss “the world’s first AI-maximalist pharmaceutical company”(33:02) Using AI agents to revisit leftover bio IP and unused data(33:22) Why so many drugs fail to reach market(35:46) Applying different agents to different kinds of tasks(44:26) The unique opportunities posed by rare diseases(46:58) On the road toward vertical integration(50:48) Hunter Leath of Archil tells us why utilizing cloud data effectively remains a complex, unsolved problem(51:56) What is “Caching as a Service”?(55:53) Why pre-caching is NOT obvious and “tremendously difficult to do”(57:00) Why the major cloud players didn’t built this themselves(01:00:37) Deliberately keeping the focus narrow… for now…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:Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWISTLinkedIn 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.Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at https://pipedrive.com/twistCheck 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

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