Podcast appearances and mentions of Brian Chesky

This Week In Startups is made possible by:Caldera + Lab - https://CalderaLab.com/TWISTNorthwest Registered Agent - https://northwestregisteredagent.com/twistLemon - https://Lemon.io/twistToday's show:Computers that read your mind? Jets that are all wings? Continuously tracking your body's vital signs to live longer? We've got all that and more on the show today.First, we sat down with the CEO of Paradromics, Matt Angle, to dig into the progress that his brain-computer interface startup has made. Yes, there are more companies working on BCIs than just Neuralink. Paradromics, in particular, is looking for early clinical trial subjects as it works to bring its technology out of the lab and into the market.If you ever wanted to know more about how BCIs work and how long it will be until we can all benefit from the tech, this is the interview for you.Next, we got JetZero CEO Tom O'Leary on the phone to tell us all about his startup's jet. No, it's not competing with Boom, a startup that wants to build a supersonic passenger airliner. Instead, JetZero is building jets that are mostly wing, allowing them to fly with far greater fuel efficiency. Best of all? The future JetZero planes can fit right into normal airports.Finally, we chatted with Nutrisense CEO Dan Zavorotny. While keeping tabs on your glucose levels may not be the sexiest topic in the world, the data that continuous monitoring can bring is incredibly valuable health information. Mix that signal with coaching, and Nutrisense reckons its combination of software, data, and dieticians can really improve health outcomes for its customers.If you needed a break from pure-play AI news, TWiST has you covered!Timestamps:0:00 Introduction1:47 Paradromics3:26 How do BCIs read your mind?9:58 Lemon - Get 15% off your first 4 weeks of developer time at Lemon.io/twist19:54 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 northwestregisteredagent.com/twist27:24 JetZero29:07 The advantages of more wing30:13 Caldera Lab - Whether you're starting fresh or upgrading your routine, Caldera Lab makes skincare simple and effective. Head to CalderaLab.com/TWIST and use TWIST at checkout for 20% off your first order.55:30 NutrisenseSubscribe 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/jasoncalacanisGreat 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

Legendary British ad man Rory Sutherland invented a fake business on a podcast, a coffee shop appealing to the busy commuter called “Flat White or F**k Off.”But it's one thing to have a post go big on TikTok or Instagram… but to turn that viral moment into an actual COMPANY is a very different challenge.On TWiST, Jason and Lon chat with Charlie Hurst, Tom Noble, and Will Sudlow, founders of the online brand “Flat White or F**k Off,” about how they took a funny little slogan and turned it into a string of popular social media accounts, a line of merch, a pop-up café, and let's face it, an entire lifestyle.PLUS we've got Mog and Dubs from Subnet 75 — Hippius! Hear how they're using the blockchain for decentralized storage, and providing server space much cheaper than their famous hyperscaler rivals.This Week In Startups is made possible by:Plaud - https://Plaud.ai/twistLinkedIn Jobs - https://LinkedIn.com/twist.Wispr Flow - https://wisprflow.ai/twistNorthwest Registered Agent  - https://www.northwestregisteredagent.com/twistTimestamps:00:00:00 Intro00:01:28 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!00:03:22 What is "decentralized cloud storage"?00:05:42 How Hippius came together00:09:57 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist.00:11:38 Incentivizing miners00:14:25 How many people are contributing?00:18:42 But where does the value accrue?00:20:18 Wispr Flow - Stop typing. Dictate with Wispr Flow and send clean, final-draft writing in seconds. Visit https://wisprflow.ai/twist to get started for free today.00:29:55 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://www.northwestregisteredagent.com/twist00:35:53 The best places to eat in Dubai00:38:06 The inspo behind "Flat White or F Off"00:42:16 From social media to IRL business00:53:06 The secrets of experiential marketing00:57:28 Hospitality's "Rule of 3s"00:59:33 Inside the Flat White London pop-up01:13:11 Lon and Jason's Oscar picks01:26:06 Lon went "Inside the Manosphere"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/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

Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline's full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown. In today's episode, we discuss: Why Zipline hires teenagers over PhDs Why the best startup employees are "heat-seeking missiles for pain" The 5 leadership attributes Zipline has never shared publicly The brutal firing advice that shaped Keller's leadership How Rwanda's health minister changed Zipline's trajectory References: Airbnb: https://www.airbnb.com Alfred Lin: https://www.linkedin.com/in/linalfred/ Amazon: https://www.amazon.com Apple: https://www.apple.com Brian Chesky: https://www.linkedin.com/in/brianchesky/ Cleveland Clinic: https://my.clevelandclinic.org Netflix: https://www.netflix.com Paul Kagame: https://www.linkedin.com/in/paulkagame/ Reflect Orbital: https://www.reflectorbital.com Sequoia Capital: https://www.sequoiacapital.com SpaceX: https://www.spacex.com Sphero: https://www.sphero.com Tesla: https://www.tesla.com University of Washington: https://www.washington.edu Walmart: https://www.walmart.com Zipline: https://www.zipline.com Where to find Keller: LinkedIn: https://www.linkedin.com/in/kellerrc/ Twitter/X: https://x.com/Keller Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 02:11 Why Zipline doesn't hire for experience 06:04 Are founders born or made? 07:37 Why Zipline hires 17-year-olds over PhDs 17:03 The employees Zipline doesn't want 18:53 The ultimate startup hire is a "heat-seeking missile" 20:36 Why blind references are a non-negotiable 23:07 Can candidates admit when they screwed up? 30:10 Zipline's secret leadership playbook 35:16 Why you should always fire quickly 36:26 The early vision for Zipline 39:48 How Zipline almost died - twice 44:55 From toy robots to drone delivery: Zipline's pivot 51:35 How Rwanda's health minister changed everything 57:10 Why Zipline's launch was a "complete disaster" 1:04:05 Scaling from 1 hospital to 5000 1:05:17 The 10x hardware cost rule every founder should know

This Week In Startups is made possible by:Circle - http://circle.so/twistSentry - http://Sentry.ioDeel - http://deel.com/twistPlaud - http://Plaud.ai/twistToday's show:It's self-driving time! We're going deep on one of the most exciting spaces developing in the world, autonomous vehicles! We've got 3 experts on the show to talk to us enlighten us, Ben Seidl of Autolane, Ming Maa of Moove, and Nathan Parker of EdgeCase.What's going on in the world of self-driving? How has the reliability of autonomous vehicles improved? What challenges are we still facing in the industry? Will the US reign victorious, or is China sneaking up? Let's find out on TWiST!Timestamps:00:00 intro02:21 Uber teams up with Zoox! 03:02 Does EdgeCase work with Zoox? 03:03 Operational design domains 06:47 The challenges of bringing self-driving to new environments. 00:10:53 Circle: The easiest way to build a home for your community, events, and courses — all under your own brand. TWiST listeners get $1,000 off the Circle Plus Plan by going to http://circle.so/twist. 00:13:26 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at Plaud.ai/twist and use code TWIST for 10% off! 00:17:19 How has reliability of autonomous cars improved? 00:19:18 How Ben Seidl came up with the idea for Autolane! 00:21:08 Sentry: New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST 00:27:47 How Moove helps autonmous vehicles go to market! 00:30:49 Deel: Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit https://deel.com/twist to learn more. 00:33:28 The logisitcs of managing fleets. 00:37:08 Why is it called Autolane and not multi-modal lane? 00:40:50 Does EdgeCase work with smaller self-driving vehicles as well? 00:41:52 How autonomous systems will interact with one-another! 00:43:14 Why AV's should not talk to other AV's on the road 00:45:07 The state of the self-driving market 00:49:12 Why Tesla isn't involving themselves in California 00:50:34 Why the US is leading the way with regulatory clarity in autonomous vehicles 01:02:51 Ben Seidl says federal regulation is a necessity 01:05:20 What is holding back self-driving growth in the US? 01:06:26 What companies make the most money in self driving 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/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

This Week In Startups is made possible by:Every Banking - https://Every.iohttps://Lemon.io - Lemon.io/twistWispr Flow - https://wisprflow.ai/twistPlaud - https://plaud.ai/twistRo.co - https://Ro.co/TwistToday's show:*Sure, we all love open source models, but what about completely decentralized AI? Rather than leaving the big decision-making in the hands of a few elite CEOs, shouldn't users have a say — and potentially even a stake — in how this incredible technology develops?On TWiST, we welcome Ala Shaabana of Crucible Labs, one of the co-founders of Bittensor. It's an open-source protocol powering a blockchain-based machine learning network. What does that mean? Users mine a crypto token — $TAO — but rather than using up their compute on solving extremely long equations, they devote it to actually powering a range of innovative AI apps (aka subnets).Plus we've got Mark Jeffrey, co-founder of the Bittensor Fund Stillcore Capital, to show us some of his favorite subnet projects, and walk us through how he trained his AI agent to mine crpyto.All that AND two amazing new OpenClaw demos.Mark Jeffrey: https://x.com/markjeffreyStillcore Capital: https://stillcorecapital.com/Ala Shaabana (Crucible Labs): https://x.com/CrucibleLabsMichael Ryaboy (Setup Claw): https://setupclaw.com/Pete and Maddie Reese (Bizzby AI): https://bizzby.ai/Timestamps:00:00 Intro01:28 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!04:11 The booming intersection of crypto, and AI agents05:49 Mark Jeffrey joins the show!06:13 Bittensor explained — how TAO subsidizes AI products07:37 Mark's top Bittensor projects00:10:40 https://Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io.00:12:20 How subnet tokens work00:17:34 How the Crucible Labs wallet simplifies subnet token allocation00:19:33 https://Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist00:22:42 The importance of private inference and encrypted AI prompts00:29:36 Wispr Flow: Stop typing. Dictate with Wispr Flow and send clean, final-draft writing in seconds. Visit https://wisprflow.ai/twist to get started for free today.00:33:07 How AI is restoring old movies and media!00:40:57 SetUpClaw's “set it and forget it” AI agents00:45:50 https://Ro.co: Ro's insurance checker will let you know if your coverage includes GLP-1s for FREE. Go to https://Ro.co/Twist for your free insurance check.00:54:35 “Off-duty” with Lon and JasonSubscribe 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

This Week In Startups is made possible by:LinkedIn Jobs - https://LinkedIn.com/twist.Deel - https://deel.com/twistIru - https://iru.com/twist!Today's show:It's a packed TWiST Today! WITH US, we've got Erik Voorhees of VeniceAI and Logan Allin of Fin Capital on to talk agents, crypto, and… you guessed it, OPENCLAW!Where does agentic AI meet the financial system? How will agents transact? And what does privacy look like in a world with omnipresent AI?Stick around for some demos! We've got George Pickett to demo OpenClaw studio and David Kaufman to show us what he's building at Siteline!Timestamps:00:04:31 What was Logan's original thesis in Circle?10:08 LinkedIn Jobs - 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.00:11:52 Logans thoughts on Open vs. Closed Source00:15:33 How to maintain privacy in AI20:02 Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit https://⁠deel.com/twist⁠ to learn more.00:23:29 Why LAUNCH's token usage is trending higher than payroll!00:25:05 How Fin capital uses personality types and AI to assess investments00:29:45 Why Erik thinks Anthropic's defiance of the federal gov. is bravery!32:10 Iru - Iru unifies identity, endpoint security, and compliance into one platform. TWiST listeners get 20% off when they book a demo at https://⁠iru.com⁠/twist!00:42:23 How Siteline is helping understand companies and their agent traffic.00:57:15 OpenClaw Studio makes OpenClaw as user friendly as possible.01:10:09 The layers and layers of Microstrategy's business model.01:11:44 Which AI tools are the most indispensable?01:12:25 How Jason uses the Grok button on threadsSubscribe 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 reception to our recent post on Code Reviews has been strong. Catch up!Amid a maelstrom of discussion on whether or not AI is killing SaaS, one of the top publicly listed SaaS companies in the world has just reported record revenues, clearing well over $1.1B in ARR for the first time with a 28% margin. As we comment on the pod, Aaron Levie is the rare public company CEO equally at home in both worlds of Silicon Valley and Wall Street/Main Street, by day helping 70% of the Fortune 500 with their Enterprise Advanced Suite, and yet by night is often found in the basements of early startups and tweeting viral insights about the future of agents.Now that both Cursor, Cloudflare, Perplexity, Anthropic and more have made Filesystems and Sandboxes and various forms of “Just Give the Agent a Box” cool (not just cool; it is now one of the single hottest areas in AI infrastructure growing 100% MoM), we find it a delightfully appropriate time to do the episode with the OG CEO who has been giving humans and computers Boxes since he was a college dropout pitching VCs at a Michael Arrington house party.Enjoy our special pod, with fan favorite returning guest/guest cohost Jeff Huber!Note: We didn't directly discuss the AI vs SaaS debate - Aaron has done many, many, many other podcasts on that, and you should read his definitive essay on it. Most commentators do not understand SaaS businesses because they have never scaled one themselves, and deeply reflected on what the true value proposition of SaaS is.We also discuss Your Company is a Filesystem:We also shoutout CTO Ben Kus' and the AI team, who talked about the technical architecture and will return for AIE WF 2026.Full Video EpisodeTimestamps* 00:00 Adapting Work for Agents* 01:29 Why Every Agent Needs a Box* 04:38 Agent Governance and Identity* 11:28 Why Coding Agents Took Off First* 21:42 Context Engineering and Search Limits* 31:29 Inside Agent Evals* 33:23 Industries and Datasets* 35:22 Building the Agent Team* 38:50 Read Write Agent Workflows* 41:54 Docs Graphs and Founder Mode* 55:38 Token FOMO Culture* 56:31 Production Function Secrets* 01:01:08 Film Roots to Box* 01:03:38 AI Future of Movies* 01:06:47 Media DevRel and EngineeringTranscriptAdapting Work for AgentsAaron Levie: Like you don't write code, you talk to an agent and it goes and does it for you, and you may be at best review it. That's even probably like, like largely not even what you're doing. What's happening is we are changing our work to make the agents effective. In that model, the agent didn't really adapt to how we work.We basically adapted to how the agent works. All of the economy has to go through that exact same evolution. Right now, it's a huge asset and an advantage for the teams that do it early and that are kinda wired into doing this ‘cause you'll see compounding returns. But that's just gonna take a while for most companies to actually go and get this deployed.swyx: Welcome to the Lane Space Pod. We're back in the chroma studio with uh, chroma, CEO, Jeff Hoover. Welcome returning guest now guest host.Aaron Levie: It's a pleasure. Wow. How'd you get upgraded to, uh, to that?swyx: Because he's like the perfect guy to be guest those for you.Aaron Levie: That makes sense actually, for We love context. We, we both really love context le we really do.We really do.swyx: Uh, and we're here with, uh, Aaron Levy. Welcome.Aaron Levie: Thank you. Good to, uh, good to be [00:01:00] here.swyx: Uh, yeah. So we've all met offline and like chatted a little bit, but like, it's always nice to get these things in person and conversation. Yeah. You just started off with so much energy. You're, you're super excited about agents.I loveAaron Levie: agents.swyx: Yeah. Open claw. Just got by, got bought by OpenAI. No, not bought, but you know, you know what I mean?Aaron Levie: Some, some, you know, acquihire. Executiveswyx: hire.Aaron Levie: Executive hire. Okay. Executive hire. Say,swyx: hey, that's my term. Okay. Um, what are you pounding the table on on agents? You have so many insightful tweets.Why Every Agent Needs a BoxAaron Levie: Well, the thing that, that we get super excited by that I think is probably, you know, should be relatively obvious is we've, we've built a platform to help enterprises manage their files and their, their corporate files and the permissions of who has access to those files and the sharing collaboration of those files.All of those files contain really, really important information for the enterprise. It might have your contracts, it might have your research materials, it might have marketing information, it might have your memos. All that data obviously has, you know, predominantly been used by humans. [00:02:00] But there's been one really interesting problem, which is that, you know, humans only really work with their files during an active engagement with them, and they kind of go away and you don't really see them for a long time.And all of a sudden, uh, with the power of AI and AI agents, all of that data becomes extremely relevant as this ongoing source of, of answers to new questions of data that will transform into, into something else that, that produces value in your organization. It, it contains the answer to the new employee that's onboarding, that needs to ramp up on a project.Um, it contains the answer to the right thing to sell a customer when you're having a conversation to them, with them contains the roadmap information that's gonna produce the next feature. So all that data. That previously we've been just sort of storing and, and you know, occasionally forgetting about, ‘cause we're only working on the new active stuff.All of that information becomes valuable to the enterprise and it's gonna become extremely valuable to end users because now they can have agents go find what they're looking for and produce new, new [00:03:00] value and new data on that information. And it's gonna become incredibly valuable to agents because agents can roam around and do a bunch of work and they're gonna need access to that data as well.And um, and you know, sometimes that will be an agent that is sort of working on behalf of, of, of you and, and effectively as you as and, and they are kind of accessing all of the same information that you have access to and, and operating as you in the system. And then sometimes there's gonna be agents that are just.Effectively autonomous and kind of run on their own and, and you're gonna collaborate and work with them kind of like you did another person. Open Claw being the most recent and maybe first real sort of, you know, kind of, you know, up updating everybody's, you know, views of this landscape version of, of what that could look like, which is, okay, I have an agent.It's on its own system, it's on its own computer, it has access to its own tools. I probably don't give it access to my entire life. I probably communicate with it like I would an assistant or a colleague and then it, it sort of has this sandbox environment. So all of that has massive implications for a platform that manage that [00:04:00] enterprise data.We think it's gonna just transform how we work with all of the enterprise content that we work with, and we just have to make sure we're building the right platform to support that.swyx: The sort of shorthand I put it is as people build agents, everybody's just realizing that every agent needs a box. Yes.And it's nice to be called box and just give everyone a box.Aaron Levie: Hey, I if I, you know, if we can make that go viral, uh, like I, I think that that terminology, I, that's theswyx: tagline. Every agentAaron Levie: needs a box. Every agent needs a box. If we can make that the headline of this, I'm fine with this. And that's the billboard I wanna like Yeah, exactly.Every agent needs a box. Um, I like it. Can we ship this? Like,swyx: okay, let's do it. Yeah.Aaron Levie: Uh, my work here is done and I got the value I needed outta this podcast Drinks.swyx: Yeah.Agent Governance and IdentityAaron Levie: But, but, um, but, but, you know, so the thing that we, we kind of think about is, um, is, you know, whether you think the number 10 x or a hundred x or whatever the number is, we're gonna have some order of magnitude more agents than people.That's inevitable. It has to happen. So then the question is, what is the infrastructure that's needed to make all those agents effective in the enterprise? Make sure that they are well governed. Make sure they're only doing [00:05:00] safe things on your information. Make sure that they're not getting exposed. The data that they shouldn't have access to.There's gonna be just incredibly spectacularly crazy security incidents that will happen with agents because you'll prompt, inject an agent and sort of find your way through the CRM system and pull out data that you shouldn't have access to. Oh, weJeff Huber: have God,Aaron Levie: right? I mean, that's just gonna happen all over the place, right?So, so then the thing is, is how do you make sure you have the right security, the permissions, the access controls, the data governance. Um, we actually don't yet exactly know in many cases how we're gonna regulate some of these agents, right? If you think about an agent in financial services, does it have the exact same financial sort of, uh, requirements that a human did?Or is it, is the risk fully on the human that was interacting or created the agent? All open questions, but no matter what, there's gonna need to be a layer that manages the, the data they have access to, the workflows that they're involved in, pulling up data from multiple systems. This is the new infrastructure opportunity in the era of agents.swyx: You have a piece on agent identities, [00:06:00] which I think was today, um, which I think a lot of breaking news, the security, security people are talking about, right? Like you basically, I, I always think of this as like, well you need the human you and then there you need the agent. YouAaron Levie: Yes.swyx: And uh, well, I don't know if it's that simple, but is box going to have an opinion on that or you're just gonna be like, well we're just the sort of the, the source layer.Yeah. Let's Okta of zero handle that.Aaron Levie: I think we're gonna have an opinion and we will work with generally wherever the contours of the market end up. Um, and the reason that we're gonna have an opinion more than other topics probably is because one of the biggest use cases for why your agent might need it, an identity is for file system access.So thus we have to kind of think about this pretty deeply. And I think, uh, unless you're like in our world thinking about this particular problem all day long, it might be, you know, like, why is this such a big deal? And the reason why it's a really big deal is because sometimes sort of say, well just give the agent an, an account on the system and it just treats, treat it like every other type of user on the system.The [00:07:00] problem is, is that I as Aaron don't really have any responsibility over anybody else's box account in our organization. I can't see the box account of any other employee that I work with. I am not liable for anything that they do. And they have, I have, I have, you know, strict privacy requirements on everything that they're able to, you know, that, that, that they work on.Agents don't have that, you know, don't have those properties. The person who creates the agent probably is gonna, for the foreseeable future, take on a lot of the liability of what that agent does. That agent doesn't deserve any privacy because, because it's, you know, it can't fully be autonomously operated and it doesn't have any legal, you know, kind of, you know, responsibility.So thus you can't just be like, oh, well I'll just create a bunch of accounts and then I'll, I'll kind of work with that agent and I'll talk to it occasionally. Like you need oversight of that. And so then the question is, how do you have a world where the agent, sometimes you have oversight of, but what if that agent goes and works with other people?That person over there is collaborating with the agent on something you shouldn't have [00:08:00] access to what they're doing. So we have all of these new boundaries that we're gonna have to figure out of, of, you know, it's really, really easy. So far we've been in, in easy mode. We've hit the easy button with ai, which is the agent just is you.And when you're in quad code and you're in cursor, and you're in Codex, you're just, the agent is you. You're offing into your services. It can do everything you can do. That's the easy mode. The hard mode is agents are kind of running on their own. People check in with them occasionally, they're doing things autonomously.How do you give them access to resources in the enterprise and not dramatically increased the security risk and the risk that you might expose the wrong thing to somebody. These are all the new problems that we have to get solved. I like the identity layer and, and identity vendors as being a solution to that, but we'll, we'll need some opinions as well because so many of the use cases are these collaborative file system use cases, which is how do I give it an agent, a subset of my data?Give it its own workspace as well. ‘cause it's gonna need to store off its own information that would be relevant for it. And how do I have the right oversight into that? [00:09:00]Jeff Huber: One thing, which, um, I think is kind interesting, think about is that you know, how humans work, right? Like I may not also just like give you access to the whole file.I might like sit next to you and like scroll to this like one part of the file and just show you that like one part and like, you know,swyx: partial file access.Jeff Huber: I'm just saying I think like our, like RA does seem to be dead, right? Like you wanna say something is dead uhhuh probably RA is dead. And uh, like the auth story to me seems like incredibly unsolved and unaddressed by like the existing state of like AI vendors.ButAaron Levie: yeah, I think, um, we're, I mean you're taking obviously really to level limit that we probably need to solve for. Yeah. And we built an access control system that was, was kind of like, you know, its own little world for, for a long time. And um, and the idea was this, it's a many to many collaboration system where I can give you any part of the file system.And it's a waterfall model. So if I give you higher up in the, in the, in the system, you get everything below. And that, that kind of created immense flexibility because I can kind of point you to any layer in the, in the tree, but then you're gonna get access to everything kind of below it. And that [00:10:00] mostly is, is working in this, in this world.But you do have to manage this issue, which is how do I create an agent that has access to some of my stuff and somebody else's stuff as well. Mm-hmm. And which parts do I get to look at as the creator of the agent? And, and these are just brand new problems? Yeah. Crazy. And humans, when there was a human there that was really easy to do.Like, like if the three of us were all sharing, there'd be a Venn diagram where we'd have an overlapping set of things we've shared, but then we'd have our own ways that we shared with each other. In an agent world, somebody needs to take responsibility for what that agent has access to and what they're working on.These are like the, some of the most probably, you know, boring problems for 98% of people on, on the internet, but they will be the problems that are the difference between can you actually have autonomous agents in an enterprise contextswyx: Yeah.Aaron Levie: That are not leaking your data constantly.swyx: No. Like, I mean, you know, I run a very, very small company for my conference and like we already have data sensitivity issues.Yes. And some of my team members cannot see Yes. Uh, the others and like, I can't imagine what it's like to run a Fortune 500 and like, you have to [00:11:00] worry about this. I'm just kinda curious, like you, you talked to a lot like, like 70, 80% of your cus uh, of the Fortune 500, your customers.Aaron Levie: Yep. 67%. Just so we're being verySEswyx: precise.So Yeah. I'm notAaron Levie: Okay. Okay.swyx: Something I'm rounding up. Yes. Round up. I'm projecting to, forAaron Levie: the government.swyx: I'm projecting to the end of the year.Aaron Levie: Okay.swyx: There you go.Aaron Levie: You do make it sound like, like we, we, well we've gotta be on this. Like we're, we're taking way too long to get to 80%. Well,swyx: no, I mean, so like. How are they approaching it?Right? Because you're, you don't have a, you don't have a final answer yet.Why Coding Agents Took Off FirstAaron Levie: Well, okay, so, so this is actually, this is the stark reality that like, unfortunately is the kinda like pouring the water on the party a little bit.swyx: Yes.Aaron Levie: We all in Silicon Valley are like, have the absolute best conditions possible for AI ever.And I think we all saw the dke, you know, kind of Dario podcast and this idea of AI coding. Why is that taken off? And, and we're not yet fully seeing it everywhere else. Well, look, if you just like enumerated the list of properties that AI coding has and then compared it to other [00:12:00] knowledge work, let's just, let's just go through a few of them.Generally speaking, you bring on a new engineer, they have access to a large swath of the code base. Like, there's like very, like you, just, like new engineer comes on, they can just go and find the, the, the stuff that they, they need to work with. It's a fully text in text out. Medium. It's only, it's just gonna be text at the end of the day.So it's like really great from a, from just a, uh, you know, kinda what the agent can work with. Obviously the models are super trained on that dataset. The labs themselves have a really strong, kind of self-reinforcing positive flywheel of why they need to do, you know, agent coding deeply. So then you get just better tooling, better services.The actual developers of the AI are daily users of the, of the thing that they're we're working on versus like the, you know, probably there's only like seven Claude Cowork legal plugin users at Anthropic any given day, but there's like a couple thousand Claude code and you know, users every single day.So just like, think about which one are they getting more feedback on. All day long. So you just go through this list. You have a, you know, everybody who's a [00:13:00] developer by definition is technical so they can go install the latest thing. We're all generally online, or at least, you know, kinda the weird ones are, and we're all talking to each other, sharing best practices, like that's like already eight differences.Versus the rest of the economy. Every other part of the economy has like, like six to seven headwinds relative to that list. You go into a company, you're a banker in financial services, you have access to like a, a tiny little subset of the total data that's gonna be relevant to do your job. And you're have to start to go and talk to a bunch of people to get the right data to do your job because Sally didn't add you to that deal room, you know, folder.And that that, you know, the information is actually in a completely different organization that you now have to go in and, and sort of run into. And it's like you have this endless list of access controls and security. As, as you talked about, you have a medium, which is not, it's not just text, right? You have, you have a zoom call that, that you're getting all of the requirements from the customer.You have a lot of in-person conversations and you're doing in-person sales and like how do you ever [00:14:00] digitize all of that information? Um, you know, I think a lot of people got upset with this idea that the code base has all the context, um, that I don't know if you follow, you know, did you follow some of that conversation that that went viral?Is like, you know, it's not that simple that, that the code base doesn't have all the knowledge, but like it's a lot, you're a lot better off than you are with other areas of knowledge work. Like you, we like, we like have documentation practices, you write specifications. Those things don't exist for like 80% of work that happens in the enterprise.That's the divide that we have, which is, which is AI coding has, has just fully, you know, where we've reached escape velocity of how powerful this stuff is, and then we're gonna have to find a way to bring that same energy and momentum, but to all these other areas of knowledge work. Where the tools aren't there, the data's not set up to be there.The access controls don't make it that easy. The context engineering is an incredibly hard problem because again, you have access control challenges, you have different data formats. You have end users that are gonna need to kind of be kind of trained through this as opposed to their adopting [00:15:00] these tools in their free time.That's where the Fortune 500 is. And so we, I think, you know, have to be prepared as an industry where we are gonna be on a multi-year march to, to be able to bring agents to the enterprise for these workflows. And I think probably the, the thing that we've learned most in coding that, that the rest of the world is not yet, I think ready for, I mean, we're, they'll, they'll have to be ready for it because it's just gonna inevitably happen is I think in coding.What, what's interesting is if you think about the practice of coding today versus two years ago. It's probably the most changed workflow in maybe the history of time from the amount of time it's changed, right? Yeah. Like, like has any, has any workflow in the entire economy changed that quickly in terms of the amount of change?I just, you know, at least in any knowledge worker workflow, there's like very rarely been an event where one piece of technology and work practice has so fundamentally, you know, changed, changed what you do. Like you don't write code, you talk to an agent and it goes and [00:16:00] does it for you, and you may be at best review it.And even that's even probably like, like largely not even what you're doing. What's happening is we are changing our work to make the agents effective. In that model, the agent didn't really adapt to how we work. We basically adapted to how the agent works. Mm-hmm. All of the economy has to go through that exact same evolution.The rest of the economy is gonna have to update its workflows to make agents effective. And to give agents the context that they need and to actually figure out what kind of prompting works and to figure out how do you ensure that the agent has the right access to information to be able to execute on its work.I, you know, this is not the panacea that people were hoping for, of the agent drops in, just automates your life. Like you have to basically re-engineer your workflow to get the most out of agents and, uh, and that, that's just gonna take, you know, multiple years across the economy. Right now it's a huge asset and an advantage for the teams that do it early and that are kinda wired into doing this.‘cause [00:17:00] you'll see compounding returns, but that's just gonna take a while for most companies to actually go and get this deployed.swyx: I love, I love pushing back. I think that. That is what a lot of technology consultants love to hear this sort of thing, right? Yeah, yeah, yeah. First to, to embrace the ai. Yes. To get to the promised land, you must pay me so much money to a hundred percent to adopt the prescribed way of, uh, conforming to the agents.Yes. And I worry that you will be eclipsed by someone else who says, no, come as you are.Aaron Levie: Yeah.swyx: And we'll meet you where you are.Aaron Levie: And, and, and and what was the thing that went viral a week ago? OpenAI probably, uh, is hiring F Dees. Yeah. Uh, to go into the enterprise. Yeah. Yeah. And then philanthropic is embedded at Goldman Sachs.Yeah. So if the labs are having to do this, if, if the labs have decided that they need to hire FDE and professional services, then I think that's a pretty clear indication that this, there's no easy mode of workflow transformation. Yeah. Yeah. So, so to your point, I think actually this is a market opportunity for, you know, new professional services and consulting [00:18:00] firms that are like Agent Build and they, and they kind of, you know, go into organizations and they figure out how to re-engineer your workflows to make them more agent ready and get your data into the right format and, you know, reconstruct your business process.So you're, you're not doing most of the work. You're telling agents how to do the work and then you're reviewing it. But I haven't seen the thing that can just drop in and, and kinda let you not go through those changes.swyx: I don't know how that kind of sales pitch goes over. Yeah. You know, you're, you're saying things like, well, in my sort of nice beautiful walled garden, here's, there's, uh, because here's this, here's this beautiful box account that has everything.Yes. And I'm like, well, most, most real life is extremely messy. Sure. And like, poorly named and there duplicate this outdated s**tAaron Levie: a hundred percent. And so No, no, a hundred percent. And so this is actually No. So, so this is, I mean, we agree that, that getting to the beautiful garden is gonna be tough.swyx: Yeah.Aaron Levie: There's also the other end of the spectrum where I, I just like, it's a technical impossibility to solve. The agent is, is truly cannot get enough context to make the right decision in, in the, in the incredibly messy land. Like there's [00:19:00] no a GI that will solve that. So, so we're gonna have to kind of land in somewhere in between, which is like we all collectively get better at.Documentation practices and, and having authoritative relatively up-to-date information and putting it in the right place like agents will, will certainly cause us to be much better organized around how we work with our information, simply because the severity of the agent pulling the wrong data will be too high and the productivity gain of that you'll miss out on by not doing this will be too high as well, that you, that your competition will just do it and they'll just have higher velocity.So, uh, and, and we, we see this a lot firsthand. So we, we build a series of agents internally that they can kind of have access to your full box account and go off and you give it a task and it can go find whatever information you're looking for and work with. And, you know, thank God for the model progress, but like, if, if you gave that task to an agent.Nine months ago, you're just gonna get lots of bogus answers because it's gonna, it's gonna say, Hey, here's, here are fi [00:20:00] five, you know, documents that all kind of smell like the right thing. And I'm gonna, but I, but you're, you're putting me on the clock. ‘cause my assistant prompt says like, you know, be pretty smart, but also try and respond to the user and it's gonna respond.And it's like, ah, it got the wrong document. And then you do that once or twice as a knowledge worker and you're just neverswyx: again,Aaron Levie: never again. You're just like done with the system.swyx: Yeah. It doesn't work.Aaron Levie: It doesn't work. And so, you know, Opus four six and Gemini three one Pro and you know, whatever the latest five 3G BT will be, like, those things are getting better and better and it's using better judgment.And this sort of like the, all of these updates to the agentic tool and search systems are, are, we're seeing, we're seeing very real progress where the agent. Kind of can, can almost smell some things a little bit fishy when it's getting, you know, we, we have this process where we, we have it go fan out, do a bunch of searches, pull up a bunch of data, and then it has to sort of do its own ranking of, you know, what are the right documents that, that it should be working with.And again, like, you know, the intelligence level of a model six months ago, [00:21:00] it'd be just throwing a dart at like, I'm just, I'm gonna grab these seven files and I, I pray, I hope that that's the right answer. And something like an opus first four five, and now four six is like, oh, it's like, no, that one doesn't seem right relative to this question because I'm seeing some signal that is making that, you know, that's contradicting the document where it would normally be in the tree and who should have access.Like it's doing all of that kind of work for you. But like, it still doesn't work if you just have a total wasteland of data. Like, it's just not, it's just not possible. Partly ‘cause a human wouldn't even be able to do it. So basically if a, if a really, really smart human. Could not do that task in five or 10 minutes for a search retrieval type task.Look, you know, your agent's not gonna be able to do it any better. You see this all day long. SoContext Engineering and Search Limitsswyx: this touches on a thing that just passionate about it was just context engineering. I, I'm just gonna let you ramble or riff on, on context engineering. If, if, if there's anything like he, he did really good work on context fraud, which has really taken over as like the term that people use and the referenceAaron Levie: a hundred percent.We, we all we think about is, is the context rob problem. [00:22:00]Jeff Huber: Yeah, there's certainly a lot of like ranking considerations. Gentech surgery think is incredibly promising. Um, yeah, I was trying to generate a question though. I think I have a question right now. Swyx.Aaron Levie: Yeah, no, but like, like I think there was this moment, um, you know, like, I don't know, two years ago before, before we knew like where the, the gotchas were gonna be in ai and I think someone was like, was like, well, infinite context windows will just solve all of these problems and ‘cause you'll just, you'll just give the context window like all the data and.It's just like, okay, I mean, maybe in 2035, like this is a viable solution. First of all, it, it would just, it would just simply cost too much. Like we just can't give the model like the 5,000 documents that might be relevant and it's gonna read them all. And I've seen enough to, to start believing in crazy stuff.So like, I'm willing to just say, sure. Like in, in 10 years from now,swyx: never say, never, never.Aaron Levie: In, in 10 years from now, we'll have infinite context windows at, at a thousandth of the price of today. Like, let's just like believe that that's possible, but Right. We're in reality today. So today we have a context engineering [00:23:00] problem, which is, I got, I got, you know, 200,000 tokens that I can work with, or prob, I don't even know what the latest graph is before, like massive degradation.16. Okay. I have 60,000 tokens that I get to work with where I'm gonna get accurate information. That's not a lot of tokens for a corpus of 10 million documents that a knowledge worker might have across all of the teams and all the projects and all the people they work with. I have, I have 10 million documents.Which, you know, maybe is times five pages per document or something like that. I'm at 50 million pages of information and I have 60,000 tokens. Like, holy s**t. Yeah. This is like, how do I bridge the 50 million pages of information with, you know, the couple hundred that I get to work with in that, in that token window.Yeah. This is like, this is like such an interesting problem and that's why actually so much work is actually like, just like search systems and the databases and that layer has to just get so locked in, but models getting better and importantly [00:24:00] knowing when they've done a search, they found the wrong thing, they go back, they check their work, they, they find a way to balance sort of appeasing the user versus double checking.We have this one, we have this one test case where we ask the agent to go find. 10 pieces of information.swyx: Is this the complex work eval?Aaron Levie: Uh, this is actually not in the eval. This is, this is sort of just like we have a bunch of different, we have a bunch of internal benchmark kind of scenarios. Every time we, we update our agent, we have one, which is, I ask it to find all of our office addresses, and I give it the list of 10 offices that we have.And there's not one document that has this, maybe there should be, that would be a great example of the kind of thing that like maybe over time companies start to, you know, have these sort of like, what are the canonical, you know, kind of key areas of knowledge that we need to have. We don't seem to have this one document that says, here are all of our offices.We have a bunch of documents that have like, here's the New York office and whatever. So you task this agent and you, you get, you say, I need the addresses for these 10 offices. Okay. And by the way, if you do this on any, you know, [00:25:00] public chat model, the same outcome is gonna happen. But for a different kind of query, you give it, you say, I need these 10 addresses.How many times should the agent go and do its search before it decides whether or not, there's just no answer to this question. Often, and especially the, the, let's say lower tier models, it'll come back and it'll give you six of the 10 addresses. And it'll, and I'll just say I couldn't find the otherswyx: four.It, it doesn't know what It doesn't know. ItAaron Levie: doesn't know what It doesn't know. Yeah. So the model is just like, like when should it stop? When should it stop doing? Like should it, should it do that task for literally an hour and just keep cranking through? Maybe I actually made up an office location and it doesn't know that I made it up and I didn't even know that I made it up.Like, should it just keep, re should it read every single file in your entire box account until it, until it should exhaust every single piece of information.swyx: Expensive.Aaron Levie: These are the new problems that we have. So, you know, something like, let's say a new opus model is sort of like, okay, I'm gonna try these types of queries.I didn't get exactly what I wanted. I'm gonna try again. I'm gonna, at [00:26:00] some point I'm gonna stop searching. ‘cause I've determined that that no amount of searching is gonna solve this problem. I'm just not able to do it. And that judgment is like a really new thing that the model needs to be able to have.It's like, when should it give up on a task? ‘cause, ‘cause you just don't, it's a can't find the thing. That's the real world of knowledge, work problems. And this is the stuff that the coding agents don't have to deal with. Because they, it just doesn't like, like you're not usually asking it about, you're, you're always creating net new information coming right outta the model for the most part.Obviously it has to know about your code base and your specs and your documentation, but, but when you deploy an agent on all of your data that now you have all of these new problems that you're dealing withJeff Huber: our, uh, follow follow-up research to context ride is actually on a genetic search. Ah. Um, and we've like right, sort of stress tested like frontier models and their ability to search.Um, and they're not actually that good at searching. Right. Uh, so you're sort of highlighting this like explore, exploit.swyx: You're just say, Debbie, Donna say everything doesn't work. Like,Aaron Levie: well,Jeff Huber: somebody has to be,Aaron Levie: um, can I just throw out one more thing? Yeah. That is different from coding and, and the rest [00:27:00] of the knowledge work that I, I failed to mention.So one other kind of key point is, is that, you know, at the end of the day. Whether you believe we're in a slop apocalypse or, or whatever. At the end of the day, if you, if you build a working product at the end of, if you, if you've built a working solution that is ultimately what the customer is paying for, like whether I have a lot of slop, a little slop or whatever, I'm sure there's lots of code bases we could go into in enterprise software companies where it's like just crazy slop that humans did over a 20 year period, but the end customer just gets this little interface.They can, they can type into it, it does its thing. Knowledge work, uh, doesn't have that property. If I have an AI model, go generate a contract and I generate a contract 20 times and, you know, all 20 times it's just 3% different and like that I, that, that kind of lop introduces all new kinds of risk for my organization that the code version of that LOP didn't, didn't introduce.These are, and so like, so how do you constrain these models to just the part that you want [00:28:00] them to work on and just do the thing that you want them to do? And, and, you know, in engineering, we don't, you can't be disbarred as an engineer, but you could be disbarred as a lawyer. Like you can do the wrong medical thing In healthcare, you, there's no, there's no equivalent to that of engineering.Like, doswyx: you want there to be, because I've considered softwareJeff Huber: engineer. What's that? Civil engineering there is, right? NotAaron Levie: software civil engineer. Sure. Oh yeah, for sure. But like in any of our companies, you like, you know, you'll be forgiven if you took down the site and, and we, we will do a rollback and you'll, you'll be in a meeting, but you have not been disbarred as an engineer.We don't, we don't change your, you know, your computer science, uh, blameJeff Huber: degree, this postmortem.Aaron Levie: Yeah, exactly. Exactly. So, so, uh, now maybe we collectively as an industry need to figure out like, what are you liable for? Not legally, but like in a, in a management sense, uh, of these agents. All sorts of interesting problems that, that, that, uh, that have to come out.But in knowledge work, that's the real hostile environments that we're operating in. Hmm.swyx: I do think like, uh, a lot of the last year's, 2025 story was the rise of coding agents and I think [00:29:00] 2026 story is definitely knowledge work agents. Yes. A hundredAaron Levie: percent.swyx: Right. Like that would, and I think open claw core work are just the beginning.Yes. Like it's, the next one's gonna just gonna be absolute craziness.Aaron Levie: It it is. And, and, uh, and it's gonna be, I mean, again, like this is gonna be this, this wave where we, we are gonna try and bring as many of the practices from coding because that, that will clearly be the forefront, which is tell an agent to go do something and has an access to a set of resources.You need to be responsible for reviewing it at the end of the process. That to me is the, is the kind of template that I just think goes across knowledge, work and odd. Cowork is a great example. Open Closet's a great example. You can kind of, sort of see what Codex could become over time. These are some, some really interesting kind of platforms that are emerging.swyx: Okay. Um, I wanted to, we touched on evals a little bit. You had, you had the report that you're gonna go bring up and then I was gonna go into like, uh, boxes, evals, but uh, go ahead. Talk about your genetic search thing.Jeff Huber: Yeah. Mostly I think kinda a few of the insights. It's like number one frontier model is not good at search.Humans have this [00:30:00] natural explore, exploit trade off where we kinda understand like when to stop doing something. Also, humans are pretty good at like forgetting actually, and like pruning their own context, whereas agents are not, and actually an agent in their kind of context history, if they knew something was bad and they even, you could see in the trace the reason you trace, Hey, that probably wasn't a good idea.If it's still in the trace, still in the context, they'll still do it again. Uhhuh. Uh, and so like, I think pruning is also gonna be like, really, it's already becoming a thing, right? But like, letting self prune the con windowsswyx: be a big deal. Yeah. So, so don't leave the mistake. Don't leave the mistake in there.Cut out the mistake but tell it that you made a mistake in the past and so it doesn't repeat it.Jeff Huber: Yeah. But like cut it out so it doesn't get like distracted by it again. ‘cause really, you know, what is so, so it will repeat its mistake just because it's been, it's inswyx: theJeff Huber: context. It'sAaron Levie: in the context so much.That's a few shot example. Even if it, yeah.Jeff Huber: It's like oh thisAaron Levie: is a great thing to go try even ifJeff Huber: it didn't work.Aaron Levie: Yeah,Jeff Huber: exactly.Aaron Levie: SoJeff Huber: there's like a bunch of stuff there. JustAaron Levie: Groundhogs Day inside these models. Yeah. I'm gonna go keep doing the same wrongJeff Huber: thing. Covering sense. I feel like, you know, some creator analogy you're trying like fit a manifold in latent space, which kind is doing break program synthesis, which is kinda one we think about we're doing right.Like, you know, certain [00:31:00] facts might be like sort of overly pitting it. There are certain, you know, sec sectors of latent space and so like plug clean space. Yeah. And, uh, andswyx: so we have a bell, our editor as a bell every time you say that. SoJeff Huber: you have, you have to like remove those, likeswyx: you shoulda a gong like TPN or something.IfJeff Huber: we gong, you either remove those links to like kinda give it the freedom, kind of do what you need to do. So, but yeah. We'll, we'll release more soon. That'sAaron Levie: awesome.Jeff Huber: That'll, that'll be cool.swyx: We're a cerebral podcast that people listen to us and, and sort of think really deep. So yeah, we try to keep it subtle.Okay. We try to keep it.Aaron Levie: Okay, fine.Inside Agent Evalsswyx: Um, you, you guys do, you guys do have EVs, you talked about your, your office thing, but, uh, you've been also promoting APEX agents and complex work. Uh, yeah, whatever you, wherever you wanna take this just Yeah. How youAaron Levie: Apex is, is obviously me, core's, uh, uh, kind of, um, agent eval.We, we supported that by sort of. Opening up some data for them around how we kind of see these, um, data workspaces in, in the, you know, kind of regular economy. So how do lawyers have a workspace? How do investment bankers have a workspace? What kind of data goes into those? And so we, [00:32:00] we partner with them on their, their apex eval.Our own, um, eval is, it's actually relatively straightforward. We have a, a set of, of documents in a, in a range of industries. We give the agent previously did this as a one shot test of just purely the model. And then we just realized we, we need to, based on where everything's going, it's just gotta be more agentic.So now it's a bit more of a test of both our harness and the model. And we have a rubric of a set of things that has to get right and we score it. Um, and you're just seeing, you know, these incredible jumps in almost every single model in its own family of, you know, opus four, um, you know, sonnet four six versus sonnet four five.swyx: Yeah. We have this up on screen.Aaron Levie: Okay, cool. So some, you're seeing it somewhere like. I, I forget the to, it was like 15 point jump, I think on the main, on the overall,swyx: yes.Aaron Levie: And it's just like, you know, these incredible leaps that, that are starting to happen. Um,swyx: and OP doesn't know any, like any, it's completely held out from op.Aaron Levie: This is not in any, there's no public data which has, you know, Ben benefits and this is just a private eval that we [00:33:00] do, and then we just happen to show it to, to the world. Hmm. So you can't, you can't train against it. And I think it's just as representative of. It's obviously reasoning capabilities, what it's doing at, at, you know, kind of test time, compute capabilities, thinking levels, all like the context rot issues.So many interesting, you know, kind of, uh, uh, capabilities that are, that are now improvingswyx: one sector that you have. That's interesting.Industries and Datasetsswyx: Uh, people are roughly familiar with healthcare and legal, but you have public sector in there.Aaron Levie: Yeah.swyx: Uh, what's that? Like, what, what, what is that?Aaron Levie: Yeah, and, and we actually test against, I dunno, maybe 10 industries.We, we end up usually just cutting a few that we think have interesting gains. All extras, won a lot of like government type documents. Um,swyx: what is that? What is it? Government type documents?Aaron Levie: Government filings. Like a taxswyx: return, likeAaron Levie: a probably not tax returns. It would be more of what would go the government be using, uh, as data.So, okay. Um, so think about research that, that type of, of, of data sets. And then we have financial services for things like data rooms and what would be in an investment prospectus. Uhhuh,swyx: that one you can dog food.Aaron Levie: Yeah, exactly. Exactly. Yes. Yes. [00:34:00] So, uh, so we, we run the models, um, in now, you know, more of an agent mode, but, but still with, with kinda limited capacity and just try and see like on a, like, for like basis, what are the improvements?And, and again, we just continue to be blown away by. How, how good these models are getting.swyx: Yeah, I mean, I think every serious AI company needs something like that where like, well, this is the work we do. Here's our company eval. Yeah. And if you don't have it, well, you're not a serious AI company.Aaron Levie: There's two dimensions, right?So there's, there's like, how are the models improving? And so which models should you either recommend a customer use, which one should you adopt? But then every single day, we're making changes to our agents. And you need to knowswyx: if you regressed,Aaron Levie: if you know. Yeah. You know, I've been fully convinced that the whole agent observability and eval space is gonna be a massive space.Um, super excited for what Braintrust is doing, excited for, you know, Lang Smith, all the things. And I think what you're going to, I mean, this is like every enter like literally every enterprise right now. It's like the AI companies are the customers of these tools. Every enterprise will have this. Yeah, you'll just [00:35:00] have to have an eval.Of all of your work and like, we'll, you'll have an eval of your RFP generation, you'll have an eval of your sales material creation. You'll have an eval of your, uh, invoice processing. And, and as you, you know, buy or use new agentic systems, you are gonna need to know like, what's the quality of your, of your pipeline.swyx: Yeah.Aaron Levie: Um, so huge, huge market with agent evals.swyx: Yeah.Building the Agent Teamswyx: And, and you know, I'm gonna shout out your, your team a bit, uh, your CTO, Ben, uh, did a great talk with us last year. Awesome. And he's gonna come back again. Oh, cool. For World's Fair.Aaron Levie: Yep.swyx: Just talk about your team, like brag a little bit. I think I, I think people take these eval numbers in pretty charts for granted, but No, there, I mean, there's, there's lots of really smart people at work during all this.Aaron Levie: Biggest shout out, uh, is we have a, we have a couple folks at Dya, uh, Sidarth, uh, that, that kind of run this. They're like a, you know, kind of tag tag team duo on our evals, Ben, our CTO, heavily involved Yasha, head of ai, uh, you know, a bunch of folks. And, um, evals is one part of the story. And then just like the full, you know, kind of AI.An agent team [00:36:00] is, uh, is a, is a pretty, you know, is core to this whole effort. So there's probably, I don't know, like maybe a few dozen people that are like the epicenter. And then you just have like layers and layers of, of kind of concentric circles of okay, then there's a search team that supports them and an infrastructure team that supports them.And it's starting to ripple through the entire company. But there's that kind of core agent team, um, that's a pretty, pretty close, uh, close knit group.swyx: The search team is separate from the infra team.Aaron Levie: I mean, we have like every, every layer of the stack we have to kind of do, except for just pure public cloud.Um, but um, you know, we, we store, I don't even know what our public numbers are in, you know, but like, you can just think about it as like a lot of data is, is stored in box. And so we have, and you have every layer of the, of the stack of, you know, how do you manage the data, the file system, the metadata system, the search system, just all of those components.And then they all are having to understand that now you've got this new customer. Which is the agent, and they've been building for two types of customers in the past. They've been building for users and they've been building for like applications. [00:37:00] And now you've got this new agent user, and it comes in with a difference of it, of property sometimes, like, hey, maybe sometimes we should do embeddings, an embedding based, you know, kind of search versus, you know, your, your typical semantic search.Like, it's just like you have to build the, the capabilities to support all of this. And we're testing stuff, throwing things away, something doesn't work and, and not relevant. It's like just, you know, total chaos. But all of those teams are supporting the agent team that is kind of coming up with its requirements of what, what do we need?swyx: Yeah. No, uh, we just came from, uh, fireside chat where you did, and you, you talked about how you're doing this. It's, it's kind of like an internal startup. Yeah. Within the broader company. The broader company's like 3000 people. Yeah. But you know, there's, there's a, this is a core team of like, well, here's the innovation center.Aaron Levie: Yeah.swyx: And like that every company kind of is run this way.Aaron Levie: Yeah. I wanna be sensitive. I don't call it the innovation center. Yeah. Only because I think everybody has to do innovation. Um, there, there's a part of the, the, the company that is, is sort of do or die for the agent wave.swyx: Yeah.Aaron Levie: And it only happens to be more of my focus simply because it's existential that [00:38:00] we get it right.swyx: Yeah.Aaron Levie: All of the supporting systems are necessary. All of the surrounding adjacent capabilities are necessary. Like the only reason we get to be a platform where you'd run an agent is because we have a security feature or a compliance feature, or a governance feature that, that some team is working on.But that's not gonna be the make or break of, of whether we get agents right. Like that already exists and we need to keep innovating there. I don't know what the right, exact precise number is, but it's not a thousand people and it's not 10 people. There's a number of people that are like the, the kind of like, you know, startup within the company that are the make or break on everything related to AI agents, you know, leveraging our platform and letting you work with your data.And that's where I spend a lot of my time, and Ben and Yosh and Diego and Teri, you know, these are just, you know, people that, that, you know, kind of across the team. Are working.swyx: Yeah. Amazing.Read Write Agent WorkflowsJeff Huber: How do you, how do you think about, I mean, you talked a lot about like kinda read workflows over your box data. Yep.Right. You know, gen search questions, queries, et cetera. But like, what about like, write or like authoring workflows?Aaron Levie: Yes. I've [00:39:00] already probably revealed too much actually now that I think about it. So, um, I've talked about whatever,Jeff Huber: whatever you can.Aaron Levie: Okay. It's just us. It's just us. Yeah. Okay. Of course, of course.So I, I guess I would just, uh, I'll make it a little bit conceptual, uh, because again, I've already, I've already said things that are not even ga but, but we've, we've kinda like danced around it publicly, so I, yeah, yeah. Okay. Just like, hopefully nobody watches this, um, episode. No.swyx: It's tidbits for the Heidi engaged to go figure out like what exactly, um, you know, is, is your sort of line of thinking.Sure. They can connect the dots.Aaron Levie: Yeah. So, so I would say that, that, uh, we, you know, as a, as a place where you have your enterprise content, there's a use case where I want to, you know, have an agent read that data and answer questions for me. And then there's a use case where I want the agent to create something.And use the file system to create something or store off data that it's working on, or be able to have, you know, various files that it's writing to about the work it's doing. So we do see it as a total read write. The harder problem has so far been the read only because, because again, you have that kind of like 10 [00:40:00] million to one ratio problem, whereas rights are a lot of, that's just gonna come from the model and, and we just like, we'll just put it in the file system and kinda use it.So it's a little bit of a technically easier problem, but the only part that's like, not necessarily technically hard, it is just like it's not yet perfected in the state of the ecosystem is, you know, building a beautiful PowerPoint presentation. It's still a hard problem for these models. Like, like we still, you know, like, like these formats are just, we're not built for.They'reswyx: working on it.Aaron Levie: They're, they're working on it. Everybody's working on it.swyx: Every launch is like, well, we do PowerPoint now.Aaron Levie: We're getting, yeah, getting a lot, getting a lot of better each time. But then you'll do this thing where you'll ask the update one slide and all of a sudden, like the fonts will be just like a little bit different, you know, on two of the slides, or it moved, you know, some shape over to the left a little bit.And again, these are the kind of things that, like in code, obviously you could really care about if you really care about, you know, how beautiful is the code, but at the end, user doesn't notice all those problems and file creation, the end user instantly sees it. You're [00:41:00] like, ah, like paragraph three, like, you literally just changed the font on me.Like it's a totally different font and like midway through the document. Mm-hmm. Those are the kind of things that you run into a lot of in the, in the content creation side. So, mm-hmm. We are gonna have native agents. That do all of those things, they'll be powered by the leading kind of models and labs.But the thing that I think is, is probably gonna be a much bigger idea over time is any agent on any system, again, using Box as a file system for its work, and in that kind of scenario, we don't necessarily care what it's putting in the file system. It could put its memory files, it could put its, you know, specification, you know, documents.It could put, you know, whatever its markdown files are, or it could, you know, generate PDFs. It's just like, it's a workspace that is, is sort of sandboxed off for its work. People can collaborate into it, it can share with other people. And, and so we, we were thinking a lot about what's the right, you know, kind of way to, to deliver that at scale.Docs Graphs and Founder Modeswyx: I wanted to come into sort of the sort of AI transformation or AI sort of, uh, operations things. [00:42:00] Um, one of the tweets that you, that you wanted to talk about, this is just me going through your tweets, by the way. Oh, okay. I mean, like, this is, you readAaron Levie: one by one,swyx: you're the, you're the easiest guest to prep for because you, you already have like, this is the, this is what I'm interested in.I'm like, okay, well, areAaron Levie: we gonna get to like, like February, January or something? Where are we in the, in the timelines? How far back are we going?swyx: Can you, can you describe boxes? A set of skills? Right? Like that, that's like, that's like one of the extremes of like, well if you, you just turn everything into a markdown file.Yeah. Then your agent can run your company. Uh, like you just have to write, find the right sequence of words toAaron Levie: Yes.swyx: To do it.Aaron Levie: Sorry, isthatswyx: the question? So I think the question is like, what if we documented everything? Yes. The way that you exactly said like,Aaron Levie: yes.swyx: Um, let's get all the Fortune five hundreds, uh, prepared for agents.Yes. And like, you know, everything's in golden and, and nicely filed away and everything. Yes. What's missing? Like, what's left, right? LikeAaron Levie: Yeah.swyx: You've, you've run your company for a decade. LikeAaron Levie: Yeah. I think the challenge is that, that that information changes a week later. And because something happened in the market for that [00:43:00] customer, or us as a company that now has to go get updated, and so these systems are living and breathing and they have to experience reality and updates to reality, which right now is probably gonna be humans, you know, kinda giving those, giving them the updates.And, you know, there is this piece about context graphs as as, uh, that kinda went very viral. Yeah. And I, I, I was like a, i, I, I thought it was super provocative. I agreed with many parts of it. I disagree with a few parts around. You know, it's not gonna be as easy as as just if we just had the agent traces, then we can finally do that work because there's just like, there's so much more other stuff that that's happening that, that we haven't been able to capture and digitize.And I think they actually represented that in the piece to be clear. But like there's just a lot of work, you know, that that has to, you just can't have only skills files, you know, for your company because it's just gonna be like, there's gonna be a lot of other stuff that happens. Yeah. Change over time.Yeah. Most companies are practically apprenticeships.swyx: Most companies are practically apprenticeships. LikeJeff Huber: every new employee who joins the team, [00:44:00] like you span one to three months. Like ramping them up.Aaron Levie: Yes. AllJeff Huber: that tat knowledgeAaron Levie: isJeff Huber: not written down.Aaron Levie: Yes.Jeff Huber: But like, it would have to be if you wanted to like give it to an Asian.Right. And so like that seems to me like to beAaron Levie: one is I think you're gonna see again a premium on companies that can document this. Mm-hmm. Much. There'll be a huge premium on that because, because you know, can you shorten that three month ramp cycle to a two week ramp cycle? That's an instant productivity gain.Can you re dramatically reduce rework in the organization because you've documented where all the stuff is and where the answers are. Can you make your average employee as good as your 90th percentile employee because you've captured the knowledge that's sort of in the heads of, of those top employees and make that available.So like you can see some very clear productivity benefits. Mm-hmm. If you had a company culture of making sure you know your information was captured, digitized, put in a format that was agent ready and then made available to agents to work with, and then you just, again, have this reality of like add a 10,000 person [00:45:00] company.Mapping that to the, you know, access structure of the company is just a hard problem. Is like, is like, yeah, well, you just, not every piece of information that's digitized can be shared to everybody. And so now you have to organize that in a way that actually works. There was a pretty good piece, um, this, this, uh, this piece called your company as a file is a file system.I, did you see that one?swyx: Nope.Aaron Levie: Uh, yes. You saw it. Yeah. And, and, uh, I actually be curious your thoughts on it. Um, like, like an interesting kind of like, we, we agree with it because, because that's how we see the world and, uh,swyx: okay. We, we have it up on screen. Oh,Aaron Levie: okay. Yeah. But, but it's all about basically like, you know, we've already, we, we, we already organized in this kind of like, you know, permission structure way.Uh, and, and these are the kind of, you know, natural ways that, that agents can now work with data. So it's kind of like this, this, you know, kind of interesting metaphor, but I do think companies will have to start to think about how they start to digitize more, more of that data. What was your take?Jeff Huber: Yeah, I mean, like the company's probably like an acid compliant file system.Aaron Levie: Uh,Jeff Huber: yeah. Which I'm guessing boxes, right? So, yeah. Yes.swyx: Yeah. [00:46:00]Jeff Huber: Which you have a great piece on, but,swyx: uh, yeah. Well, uh, I, I, my, my, my direction is a little bit like, I wanna rewind a little bit to the graph word you said that there, that's a magic trigger word for us. I always ask what's your take on knowledge graphs?Yeah. Uh, ‘cause every, especially at every data database person, I just wanna see what they think. There's been knowledge graphs, hype cycles, and you've seen it all. So.Aaron Levie: Hmm. I actually am not the expert in knowledge graphs, so, so that you might need toswyx: research, you don't need to be an expert. Yeah. I think it's just like, well, how, how seriously do people take it?Yeah. Like, is is, is there a lot of potential in the, in the HOVI?Aaron Levie: Uh, well, can I, can I, uh, understand first if it's, um, is this a loaded question in the sense of are you super pro, super con, super anti medium? Iswyx: see pro, I see pros and cons. Okay. Uh, but I, I think your opinion should be independent of mine.Aaron Levie: Yeah. No, no, totally. Yeah. I just want to see what I'm stepping into.swyx: No, I know. It's a, and it's a huge trigger word for a lot of people out Yeah. In our audience. And they're, they're trying to figure out why is that? Because whyAaron Levie: is this such aswyx: hot item for them? Because a lot of people get graph religion.And they're like, everything's a graph. Of course you have to represent it as a graph. Well, [00:47:00] how do you solve your knowledge? Um, changing over time? Well, it's a graph.Aaron Levie: Yeah.swyx: And, and I think there, there's that line of work and then there's, there's a lot of people who are like, well, you don't need it. And both are right.Aaron Levie: Yeah. And what do the people who say you don't need it, what are theyswyx: arguing for Mark down files. Oh, sure, sure. Simplicity.Aaron Levie: Yeah.swyx: Versus it's, it's structure versus less structure. Right. That's, that's all what it is. I do.Aaron Levie: I think the tricky thing is, um, is, is again, when this gets met with real humans, they're just going to their computer.They're just working with some people on Slack or teams. They're just sharing some data through a collaborative file system and Google Docs or Box or whatever. I certainly like the vision of most, most knowledge graph, you know, kind of futuristic kind of ways of thinking about it. Uh, it's just like, you know, it's 2026.We haven't seen it yet. Kind of play out as as, I mean, I remember. Do you remember the, um, in like, actually I don't, I don't even know how old you guys are, but I'll for, for to show my age. I remember 17 years ago, everybody thought enterprises would just run on [00:48:00] Wikis. Yeah. And, uh, confluence and, and not even, I mean, confluence actually took off for engineering for sure.Like unquestionably. But like, this was like everything would be in the w. And I think based on our, uh, our, uh, general style of, of, of what we were building, like we were just like, I don't know, people just like wanna workspace. They're gonna collaborate with other people.swyx: Exactly. Yeah. So you were, you were anti-knowledge graph.Aaron Levie: Not anti, not anti. Soswyx: not nonAaron Levie: I'm not, I'm not anti. ‘cause I think, I think your search system, I just think these are two systems that probably, but like, I'm, I'm not in any religious war. I don't want to be in anybody's YouTube comments on this. There's not a fight for me.swyx: We, we love YouTube comments. We're, we're, we're get into comments.Aaron Levie: Okay. Uh, but like, but I, I, it's mostly just a virtue of what we built. Yeah. And we just continued down that path. Yeah.swyx: Yeah.Aaron Levie: And, um, and that, that was what we pursued. But I'm not, this is not a, you know, kind of, this is not a, uh, it'sswyx: not existential for you. Great.Aaron Levie: We're happy to plug into somebody else's graph.We're happy to feed data into it. We're happy for [00:49:00] agents to, to talk to multiple systems. Not, not our fight.swyx: Yeah.Aaron Levie: But I need your answer. Yeah. Graphs or nerd Snipes is very effective nerd.swyx: See this is, this is one, one opinion and then I've,Jeff Huber: and I think that the actual graph structure is emergent in the mind of the agent.Ah, in the same way it is in the mind of the human. And that's a more powerful graph ‘cause it actually involved over time.swyx: So don't tell me how to graph. I'll, I'll figure it out myself. Exactly. Okay. All right. AndJeff Huber: what's yours?swyx: I like the, the Wiki approach. Uh, my, I'm actually

This Week In Startups is made possible by:Deel - http://deel.com/twistWispr Flow - https://wisprflow.ai/twistLuma AI - https://lumalabs.ai/twistToday's show:*$110 billion buys you 15% of OpenAI. Amazon, Nvidia, and SoftBank placed their bets on ChatGPT, which now has 900 million weekly active users and 50 million paying subscribers. Find out why Jason is anticipating the wildest J-Curve swing of all time, and believes we've ALREADY hit AGI… it's just not implemented yet.Plus a visit from our roving correspondent Nick O'Neill, checking in on the Crypto Chaos in Miami Beach, and hot demos from three young founders.GUESTS:Nick O'Neill: https://x.com/chooserichEverest Chris: https://openclaw.unloopa.com/Ben Broca: https://polsia.com/Adi Gabrani: https://makemyclaw.com/Timestamps:00:00 Intro01:33 We're hiring a new producer!05:42 OpenAI raised $110 billion08:59 Understanding the LLM J-Curve00:11:25 Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit ⁠https://deel.com/twist⁠ to learn more.00:15:02 CRYPTO CHAOS IN MIAMI BEACH!00:21:10 Wispr Flow - Stop typing. Dictate with Wispr Flow and send clean, final-draft writing in seconds. Visit ⁠https://wisprflow.ai/twist⁠ to get started for free today.00:22:54 Mass layoffs at Block00:30:50 Luma AI - Stop guessing and start directing with the all-in-one Dream Machine text-to-video platform. Visit ⁠https://lumalabs.ai/twist⁠ to try The Dream Machine for free.00:32:04 AI Scott Adams: The Saga Continues00:38:13 Make URLs for local businesses with Unloopa00:45:36 Rent a Polsia agent to run your company00:58:55 Deploy swarms in 60 seconds with MakeMyClaw01:05:05 LAUNCH FEST is coming to SF01:55:49 Will Paramount actually buy WBD?01:06:58 Why Lon loves “Knight of the 7 Kingdoms”01:07:21 On “Neighbors” and First Amendment Warriors01:13:43 All about Jason's favorite chargersSubscribe 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

This Week In Startups is made possible by:Lemon IO - https://Lemon.io/twistEvery.io - https://every.io Sentry.io- https://sentry.io/twistToday's show:We're going behind the curtain today — it's a packed show!We found Tyler Yust, OpenClaw's third EVER contributor to share his insights from within foundation! We've got Deedy Das, of Menlo Ventures, on the show to discuss whether SaaS is cooked! Next we met the creator of an OpenClaw instance that fits in your pocket! We've also got the founder of OpenBrowse showing us how he automatically detects and generates OpenClaw skills!Timestamps:00:00 Intro - Deedy Das Joins the Show!04:54 Anthropic's revenue growth and valuation06:07 OpenClaw Contributor Tyler Yuts joins the show09:24 iMessage integration and Apple's proprietary systems00:10:07 Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist14:31 Anthropic vs. the Pentagon00:20:02 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io.00:30:08 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST00:35:46 The Infamous Citrini article00:32:47 Come to LAUNCH fest! https://fest.launch.co00:36:28 Why Deedy thinks the Cetrini article is a work of science fiction00:44:51 The illusion of privacy in corporate America00:41:18 Deedy thinks Enterprise SaaS apps aren't going to be vibe coded00:49:20 Jason's Reddit Bot00:52:01 Jason's obsession with Singapore's food00:55:22 How Unbrowse pulls any backend API!01:02:07 Sebastian shows off the smallest OpenClaw form factor!01:12:04 The Prolo ring — for people who doomscroll01:20:21 Deedy's Podcast Player App!Thank you to our partners:(10:07) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(20:02) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.(30:08) Sentry - New users can get $240 in free credits when they go to sentry.io/twist and use the code TWISTSubscribe 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

On Monday's Good Morning Hospitality, A Skift Podcast, Wil Slickers, Michael Goldin, Brandreth Canaley, and Jamie Lane dig into the latest headlines shaping online travel, short-term rentals, and platform strategy. Otamiser has secured $2M in fresh capital to scale its AI-driven revenue platform for hotels and STR operators, highlighting continued investor interest in tech that boosts OTA visibility and revenue. Airbnb is testing loyalty benefits — exploring non-traditional perks and potential paid-member mechanics that CEO Brian Chesky says could be a “massive accelerant” for repeat stays. The team also breaks down how Airbnb's hotel strategy is expanding far beyond pilot programs into broader markets, revisiting its competitive stance versus OTAs like Booking.com and others. Tripadvisor CEO Matt Goldberg acknowledged in a confidential memo that recent share price volatility and investor frustration with slow AI progress are weighing on the business, while Sabre Corporation announced layoffs and leadership reshuffles as it pivots toward becoming an “AI-native” tech provider. Connect with Airline Weekly LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/airline-weekly/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://x.com/Airline_Weekly/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/airlineweekly/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/skiftnews/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ WhatsApp: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Subscribe to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@SkiftNews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and never miss an update from the airline and travel industries.

On Monday's Good Morning Hospitality, A Skift Podcast, Wil Slickers, Michael Goldin, Brandreth Canaley, and Jamie Lane dig into the latest headlines shaping online travel, short-term rentals, and platform strategy. Otamiser has secured $2M in fresh capital to scale its AI-driven revenue platform for hotels and STR operators, highlighting continued investor interest in tech that boosts OTA visibility and revenue. Airbnb is testing loyalty benefits — exploring non-traditional perks and potential paid-member mechanics that CEO Brian Chesky says could be a “massive accelerant” for repeat stays. The team also breaks down how Airbnb's hotel strategy is expanding far beyond pilot programs into broader markets, revisiting its competitive stance versus OTAs like Booking.com and others. Tripadvisor CEO Matt Goldberg acknowledged in a confidential memo that recent share price volatility and investor frustration with slow AI progress are weighing on the business, while Sabre Corporation announced layoffs and leadership reshuffles as it pivots toward becoming an “AI-native” tech provider. Connect with Airline Weekly LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/airline-weekly/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://x.com/Airline_Weekly/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/airlineweekly/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/skiftnews/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ WhatsApp: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Subscribe to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@SkiftNews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and never miss an update from the airline and travel industries.

This Week In Startups is made possible by:Gusto - https://Gusto.com/twistCircle - https://circle.so/twistNorthwest Registered Agent - https://northwestregisteredagent.com/twistToday's show:*Getting OpenClaw set up and running without destroying your bank account is one thing.But now that you have your agent or swarm operational, how can you use them to get real work done?We have three builders who are going to show you how to maximize your OpenClaw output!GUESTS:Jordy Coltman: Viral X author and creator of the WeeklyClaw newsletterJesse Leimgruber: Creator of the OpenHome.com smart speaker and kitTremaine Grant: Founder/CEO of PulsePLUS, on Off Duty, Lon and Jason talk “Knight of the 7 Kingdoms” and “The Pitt,” react to the “Mandalorian and Grogu” trailer, and check out some of Jason's favorite headphones and earbuds.Timestamps:00:40 We're gonna show you how to maximize your IRL OpenClaw productivity00:50 Even AI skeptic Lon is blown away by OpenClaw's power01:46 Jordy Coltman's top time-wasting mistakes made by OpenClaw beginners03:00 Why Jordy thinks new hardware is the best home for your agents05:38 Why Jason thinks “OpenClaw is a box” is coming soon08:29 Tremaine Grant of Pulse demos his “virtual office” interface and the “Heartbeat Protocol”00:10:15 Gusto - 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.00:15:16 What's really happening when agents “chat” together?00:18:53 Jesse Leimgruber's demos his OpenHome AI smart speakers00:19:47 Circle.so - The easiest way to build a home for your community, events, and courses — all under your own brand. TWiST listeners get $1,000 off the Circle Plus Plan by going to http://circle.so/twist.00:22:55 Freeing agents from screens and making them proactive00:29:43 Northwest Registered Agent - 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 www.northwestregisteredagent.com/twist00:30:58 Why Jason wants his agent to read Slack and emails to him00:50:05 Who polices autonomous agents? Other agents?00:53:32 Jason and Lon's thoughts on “Knight of the Seven Kingdoms”00:56:20 Lon's favorite picks from Quentin Tarantino's Top 10 movies01:01:13 “The Mandalorian and Grogu” trailer reaction01:05:22 Jason's favorite earbuds and headphonesSubscribe 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:00:10:15 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.00:19:47 Circle.so - The easiest way to build a home for your community, events, and courses — all under your own brand. TWiST listeners get $1,000 off the Circle Plus Plan by going to http://circle.so/twist.00:29:43 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 www.northwestregisteredagent.com/twistCheck 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/@calacanis

Lenny's Podcast: Product | Growth | Career ✓ Claim : Read the notes at at podcastnotes.org. Don't forget to subscribe for free to our newsletter, the top 10 ideas of the week, every Monday --------- Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia's fastest-growing founders as their in-house CEO coach.We discuss:1. His LOCKS framework for evaluating founders2. Why you should build your team like the 2004 Red Sox3. Why hiring “spicy” candidates beats consensus picks4. Why enterprise sales will be the last white-collar job AI replaces5. Some of my favorite “Halliganisms”—Brought to you by:Sentry—Code breaks, fix it faster: http://sentry.io/lennyDatadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Brian Halligan• X: https://x.com/bhalligan• LinkedIn: linkedin.com/in/brianhalligan• Delphi: https://www.delphi.ai/bhalligan• Podcast: https://sequoiacap.com/series/long-strange-trip—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Brian Halligan(03:56) The perpetual state of constructive dissatisfaction(05:25) Coaching CEOs(07:49) The art of interviewing and hiring(11:21) Getting the most out of reference calls(13:10) Homegrown talent vs. big company hires(16:31) Traits of successful CEOs(19:40) Brian's LOCKS framework for evaluating founders(21:34) Are great CEO's born or made?(23:41) Giving effective feedback(25:54) The future of go-to-market strategies(31:56) Understanding forward deployed engineers(34:17) How the CEO role has evolved over the last 20 years(38:10) Halliganisms(01:01:18) The CEO's role in scaling a company(01:02:41) Lightning round and final thoughts—Referenced:• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria• HubSpot: https://www.hubspot.com• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• McKinsey & Company: https://www.mckinsey.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392• OpenClaw: https://openclaw.ai• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159• Dalai Lama's 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin• Glassdoor: https://www.glassdoor.com• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan• Marc Andreessen: The real AI boom hasn't even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution• Delphi: https://www.delphi.ai• Sonos: https://www.sonos.com• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan• The Boston Red Sox: https://www.mlb.com/redsox—Recommended book:• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Gary Tan is the President and CEO of Y Combinator.YC is the startup accelerator behind companies like Airbnb, Stripe, Coinbase, Reddit, Twitch, and thousands more. According to Garry, they've invested in 20% of all startups worth $5B or more started since 2012.Gary has lived every side of the YC ecosystem. He went through YC as a founder, later became a partner, started Initialized Capital where he backed companies like Coinbase and Instacart, and then returned to lead YC.We walk through the different “eras” of YC, from the early Paul Graham and Jessica Livingston days in Cambridge, to scaling in San Francisco, to today's push back toward in person community and what Gary calls “founder mode” for the organization itself.We also talk about why the Bay Area still matters so much for startups, what's happening with California taxes and policy, and why Gary has gotten more involved in local politics to keep it the best place for founders to build companies.Then we go deep on the parts of startups people don't talk about enough. Co-founder conflict, rage quitting, therapy and coaching, and why companies inevitably take on the personality and emotional patterns of their founders.We also cover what YC looks for in applications, how the 13 week batch is structured, how Demo Day really works, how to choose the right investors, and what Gary thinks the next phase of YC looks like, including helping founders even after Series A.At the end, Gary shares his personal AI workflow, including meta prompting, comparing outputs across models, and the tools he uses every day to think and build faster.Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:05) Moving from Winnipeg to California as a kid(1:35) How YC interviews work(2:55) The first batch in 2005(6:46) Why YC moved from Boston to SF(8:17) California's Billionaire Tax(11:00) Tech should care about public policies(17:01) Going direct to your audience(20:28) The 2nd Era of YC(24:01) Rage quitting Palantir, learning to understand himself(32:41) Co-founder conflict kills most startups(35:15) Joining YC as a group partner(37:22) Initialized Fund 1 (55x DPI)(39:44) Why Garry went back to lead YC(42:44) YC funds 20% of all $5B+ companies(44:30) Lessons from Brian Chesky(48:01) Garry's thoughts on YC rejection(51:41) How to get into YC(58:03) What it's like inside a 13-week YC batch(1:02:23) 20% of YC is hard tech(1:05:55) YC's 3rd era: founder mode, re-batching(1:07:56) Escaping the matrix(1:11:26) Garry's personal AI stack(1:20:25) Tech optimismReferencedY Combinator: https://www.ycombinator.com/Initialized Capital: https://initialized.com/Torch: https://torch.io/Perplexity: https://www.perplexity.ai/Anthropic: https://www.anthropic.com/OpenAI: https://openai.com/Airbnb: https://www.airbnb.com/Kyle Vogt on his new startup: https://www.youtube.com/watch?v=XQoFbvyWEy8Follow Aaron Levie on X: https://x.com/levieFollow GaryTwitter: https://x.com/garytanLinkedIn: https://www.linkedin.com/in/garytan/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Lenny's Podcast: Product | Growth | Career ✓ Claim Key Takeaways Check out the episode pageRead the full notes @ podcastnotes.orgBrian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia's fastest-growing founders as their in-house CEO coach.We discuss:1. His LOCKS framework for evaluating founders2. Why you should build your team like the 2004 Red Sox3. Why hiring “spicy” candidates beats consensus picks4. Why enterprise sales will be the last white-collar job AI replaces5. Some of my favorite “Halliganisms”—Brought to you by:Sentry—Code breaks, fix it faster: http://sentry.io/lennyDatadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Brian Halligan• X: https://x.com/bhalligan• LinkedIn: linkedin.com/in/brianhalligan• Delphi: https://www.delphi.ai/bhalligan• Podcast: https://sequoiacap.com/series/long-strange-trip—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Brian Halligan(03:56) The perpetual state of constructive dissatisfaction(05:25) Coaching CEOs(07:49) The art of interviewing and hiring(11:21) Getting the most out of reference calls(13:10) Homegrown talent vs. big company hires(16:31) Traits of successful CEOs(19:40) Brian's LOCKS framework for evaluating founders(21:34) Are great CEO's born or made?(23:41) Giving effective feedback(25:54) The future of go-to-market strategies(31:56) Understanding forward deployed engineers(34:17) How the CEO role has evolved over the last 20 years(38:10) Halliganisms(01:01:18) The CEO's role in scaling a company(01:02:41) Lightning round and final thoughts—Referenced:• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria• HubSpot: https://www.hubspot.com• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• McKinsey & Company: https://www.mckinsey.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392• OpenClaw: https://openclaw.ai• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159• Dalai Lama's 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin• Glassdoor: https://www.glassdoor.com• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan• Marc Andreessen: The real AI boom hasn't even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution• Delphi: https://www.delphi.ai• Sonos: https://www.sonos.com• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan• The Boston Red Sox: https://www.mlb.com/redsox—Recommended book:• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

On this episode of Good Morning Hospitality, A Skift Podcast, Wil Slickers⁠, ⁠Jamie Lane⁠, Brandreth Canaley⁠, and ⁠Michael Goldin dive into the latest shifts across short-term rentals and online travel. They start with Brian Chesky dismissing rivals' chatbots and arguing that Airbnb's AI advantage is rooted in its marketplace and community data, then unpack Airbnb's new report positioning STRs as a critical pressure valve for lodging demand during peak travel periods. The conversation then turns to Expedia Group's Q4 2025 earnings, where stronger B2B results helped offset softer consumer trends, before closing on leadership tension at Casago as franchisees react to shifting power dynamics. The episode wraps with a broader look at AI strategy, consolidation, and who really controls distribution in today's STR ecosystem. Connect with Skift LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/skift/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ WhatsApp: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://facebook.com/skiftnews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/skiftnews/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Threads: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.threads.net/@skiftnews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Bluesky: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bsky.app/profile/skiftnews.bsky.social⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/skift⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Subscribe to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@SkiftNews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and never miss an update from the travel industry.

On this episode of Good Morning Hospitality, A Skift Podcast, Wil Slickers⁠, ⁠Jamie Lane⁠, Brandreth Canaley⁠, and ⁠Michael Goldin dive into the latest shifts across short-term rentals and online travel. They start with Brian Chesky dismissing rivals' chatbots and arguing that Airbnb's AI advantage is rooted in its marketplace and community data, then unpack Airbnb's new report positioning STRs as a critical pressure valve for lodging demand during peak travel periods. The conversation then turns to Expedia Group's Q4 2025 earnings, where stronger B2B results helped offset softer consumer trends, before closing on leadership tension at Casago as franchisees react to shifting power dynamics. The episode wraps with a broader look at AI strategy, consolidation, and who really controls distribution in today's STR ecosystem. Connect with Skift LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/skift/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ WhatsApp: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://facebook.com/skiftnews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/skiftnews/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Threads: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.threads.net/@skiftnews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Bluesky: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bsky.app/profile/skiftnews.bsky.social⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/skift⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Subscribe to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@SkiftNews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and never miss an update from the travel industry.

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia's fastest-growing founders as their in-house CEO coach.We discuss:1. His LOCKS framework for evaluating founders2. Why you should build your team like the 2004 Red Sox3. Why hiring “spicy” candidates beats consensus picks4. Why enterprise sales will be the last white-collar job AI replaces5. Some of my favorite “Halliganisms”—Brought to you by:Sentry—Code breaks, fix it faster: http://sentry.io/lennyDatadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Brian Halligan• X: https://x.com/bhalligan• LinkedIn: linkedin.com/in/brianhalligan• Delphi: https://www.delphi.ai/bhalligan• Podcast: https://sequoiacap.com/series/long-strange-trip—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Brian Halligan(03:56) The perpetual state of constructive dissatisfaction(05:25) Coaching CEOs(07:49) The art of interviewing and hiring(11:21) Getting the most out of reference calls(13:10) Homegrown talent vs. big company hires(16:31) Traits of successful CEOs(19:40) Brian's LOCKS framework for evaluating founders(21:34) Are great CEO's born or made?(23:41) Giving effective feedback(25:54) The future of go-to-market strategies(31:56) Understanding forward deployed engineers(34:17) How the CEO role has evolved over the last 20 years(38:10) Halliganisms(01:01:18) The CEO's role in scaling a company(01:02:41) Lightning round and final thoughts—Referenced:• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria• HubSpot: https://www.hubspot.com• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• McKinsey & Company: https://www.mckinsey.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392• OpenClaw: https://openclaw.ai• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159• Dalai Lama's 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin• Glassdoor: https://www.glassdoor.com• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan• Marc Andreessen: The real AI boom hasn't even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution• Delphi: https://www.delphi.ai• Sonos: https://www.sonos.com• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan• The Boston Red Sox: https://www.mlb.com/redsox—Recommended book:• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Hacer cosas chulas te lleva a gente que hace cosas chulas. Esta frase de Miguel resume mi plan de carrera. Tú solo preocúpate por lanzar un producto distinto y todo encajará luego. Quizá serán unos meses, quizá unos años, pero el éxito tarde o temprano llegará, cuando el contenido que generas es fresco y relevante. No eres la copia de nada, lo que sacas es genuinamente tuyo. Miguel lanzó RevenueCat en 2017 y desde entonces que hace cosas chulas y por eso conecta con gente que hace cosas chulas.Kapital es posible gracias a sus colaboradores:Thenomba es la escuela que te prepara para encontrar un propósito, no un trabajo.⁠Thenomba⁠. La escuela que te hará encontrar tu propósito.Me han hecho embajador del proyecto y puedo ofrecerte un descuento especial en el precio. Si quieres matricularte, utiliza el código KAPITAL20 para llevarte una rebaja del 20%. 42 oyentes de este podcast ya utilizaron el código en la exitosa edición de diciembre. Si te preguntas si esto encaja contigo, te recomiendo simplemente escuchar los episodios de hace unas semanas con Higinio Marín y Ricardo Piñero. Higinio y Ricardo son dos de los profesores del máster y esas dos entrevistas reflejan la vocación humanista de su programa. Si resuenan en tu cabeza algunas de las ideas en esas conversaciones, entonces Thenomba es para ti.Patrocina Kapital. Toda la información en este link.Índice:0:32 Subir el listón y confiar en el proceso.10:13 El mito del overnight success.19:44 La bonita sensación que puedes competir contra cualquiera.22:58 Llega internet a los hogares españoles.30:47 Europa va perdida en la revolución de la IA.33:54 La franqueza de los americanos con el dinero.43:09 Hackear el credit score.46:40 Trump en California.49:20 Relaciones superficiales.54:14 Mítico capítulo de Tesla.59:56 Cómo no pedir un favor.1:04:55 Plan para ir a Silicon Valley.1:09:07 El imperfecto sonido de la Motown.1:12:37 Erlich existe en el mundo real.1:22:04 Triángulos del éxito de Jack Barker.Apuntes:Reflections on computers & humans. Miguel Carranza.The long run. Miguel Carranza.How NOT to apply to Y Combinator. Miguel Carranza.The privilege of free education. Miguel Carranza.8 años, 10 años, 14 años, 18 años. Iñaki Arrola.Hitsville: The making of Motown. Ben Turner & Gabe Turner.Founder mode. Brian Chesky.Silicon Valley. Mike Judge & John Altschuler & Dave Krinsky.

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Intro 00:08 What design actually does at a software company 01:40 The roots of design: from industrial design to software 03:29 Useful, usable, desirable — and used 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 25:11 When lowering the quality bar actually cost the business 27:53 How to build judgment through pattern matching 31:25 How Ryan's design team differs from the rest 34:31 Why Figma is not the source of truth 36:32 How Ryan spends his week: recruiting, crits, and staff meetings 38:39 The "Do/Try/Consider" framework 42:12 The most important decisions of the past year 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution

In this episode, I'm diving into How I Built This by Guy Raz, exploring the incredible story of how Airbnb's cofounders bootstrapped their way to building one of the most recognizable brands in the world. I focused on the chapter detailing Airbnb's early days—when Brian Chesky, Joe Gebbia, and Nathan Blecharczyk were struggling to pay rent and came up with the wild idea of renting out air mattresses in their apartment. This chapter brilliantly captures the scrappy, resourceful spirit of bootstrapping and the power of solving your own problem.Guy Raz has mastered the art of the interview-based podcast, and this book is a perfect example of how that format can be repurposed into compelling long-form content. Each chapter reads like a conversation (if a little jargon-heavy)—accessible, engaging, and full of practical wisdom from entrepreneurs who've been in the trenches. It's proof that great storytelling transcends medium.My article on vibe coding: https://www.pleasehustleresponsibly.com/p/i-tried-vibe-coding-for-90-daysYou may also like this book: https://www.honeyandhustle.co/i-read-a-chapter-of-earn-it-by-steve-pratt-for-you/Thanks for listening! Let's keep the convo going: Join the community, Please Hustle Responsibly: https://pleasehustleresponsibly.com/Find all episodes here: https://www.honeyandhustle.coYouTube: https://www.youtube.com/c/AngelaHollowellLinkedIn: https://www.linkedin.com/in/angelahollowell/Twitter: https://twitter.com/honeyandhustleMentioned in this episode:Subscribe to the newsletter today: www.pleasehustleresponsibly.comDownload the free guide on How to get your first 1,000 subscribers here: https://www.angelahollowell.com/first1000

Brian Chesky is the co-founder and CEO of Airbnb, a company that began with airbeds and grew into a worldwide community built on trust and belonging. He joins to discuss how imagination and design shaped his path from art school to entrepreneurship, and what it means to design the world you want to live in.Learn more about our flagship conference happening this April at attend.ted.com/podcast Hosted on Acast. See acast.com/privacy for more information.

Lenny's Podcast: Product | Growth | Career ✓ Claim : Read the notes at at podcastnotes.org. Don't forget to subscribe for free to our newsletter, the top 10 ideas of the week, every Monday --------- Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Airbnb CEO Brian Chesky talks with TITV Host Akash Pasricha about the company's new CTO Ahmad Al-Dahle and how AI will revolutionize the travel experience. We also talk with Aaron Holmes about Microsoft's growing $500 million relationship with Anthropic and Baseten CEO Tuhin Srivastava about its role in the booming AI inference market. Additionally, we get into the launch of the tech-focused Door Bank with Ken Brown, and we end with Shane Burke discussing whether a proposed wealth tax is pushing billionaires out of California.Articles discussed on this episode: https://www.theinformation.com/articles/californians-want-texas-top-destinationhttps://www.theinformation.com/articles/microsofts-spending-anthropic-ai-pace-hit-500-millionhttps://www.theinformation.com/articles/upstart-tech-bank-trying-shake-financehttps://www.theinformation.com/briefings/airbnb-hires-former-meta-ai-leader-ctoTITV airs on YouTube, X and LinkedIn at 10AM PT / 1PM ET. Or check us out wherever you get your podcasts.Subscribe to: - The Information on YouTube: https://www.youtube.com/@theinformation- The Information: https://www.theinformation.com/subscribe_hSign up for the AI Agenda newsletter: https://www.theinformation.com/features/ai-agenda

Lenny's Podcast: Product | Growth | Career ✓ Claim Key Takeaways Deliberately understaff projects: Constraints force creativity and prevent bloat from politics and bureaucracyYou've gone too far when teams can't ship basic functionalityThe sweet spot is uncomfortable but productive tensionGood teams get tired; great teams run in the red constantly and destroy good teams in that momentHigh alpha, low beta framework: Evaluate people and processes on upside potential (alpha) versus volatility (beta)Prioritize high alpha opportunities even with higher betaProcesses exist solely to lower beta but suppress alpha as a trade-offThe nuanced dance is decreasing volatility where needed (like payroll) without killing upside in innovation areasKnow when to quit your startup: If you're not certain you have product-market fit, you don't have itCompanies that hit big do so quickly; the “never quit” mentality is VC propaganda designed to extract value from founders, not protect themPivot twice or three times maximum, typically by year fourYou're running an experiment to see if the universe has binding receptors for your product. If not, move on… Leadership means fighting entropy relentlesslyTeams naturally optimize for local comfort and disorderExecutives must demand 99% energy levels daily, or the system decaysTop performers don't get 10% more rewards; they get 10-100xBeing “chill” accomplishes nothingWithholding negative feedback is selfish because you prioritize your comfort over making teammates and the company better Read the full notes @ podcastnotes.orgMatt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ça devient une tradition, et cette année elle prend une toute nouvelle dimension. Pour la troisième fois consécutive, je partage le micro avec Clémence Lepic pour ce bilan annuel. Sauf que cette fois, ce n'est plus seulement ma productrice, c'est aussi mon associée. 2025 aura été une année de folie : deux films sur YouTube et un troisième qui arrive, 72 épisodes de GDIY, l'explosion de Combien ça gagne, et surtout... la création de Collision Productions, une société pour rassembler tous nos projets. C'est aussi une année où on a regardé la vérité en face : la dépendance aux IA américaines, ces enjeux de durabilité et de souveraineté de plus en plus centraux, la nécessité de rester positifs quand tout nous pousse vers le bas et tant d'autres sujets qu'on a adoré creuser. Dans ce hors-série, nous allons : Revenir sur les épisodes phares de 2025, de Carlos Ghosn à Ivan Zhao en passant par Esther Perel, Brian Chesky et tant d'autres Vous révéler les coulisses de nos plus grosses productions : notre voyage au Brésil, le lancement de notre série spéciale CAC 40, notre tournage en Chine et le film qui arrive en janvier (nous trépignons d'impatience) et tous nos projets vidéos en coursParler du lancement imminent de notre nouveau podcast — que nous n'avons dévoilé nulle part ! Évoquer notre deuxième formation avec l'EDHEC (qui va vous retourner le cerveau), construite dans l'ombre depuis des mois, avec experts chercheurs et scientifiques Vous dévoiler nos ambitions pour 2026 : nos invités "moonshot", nos prochains projets de films sur YouTube, notre arrivée imminente sur une nouvelle plateforme (vous n'êtes pas prêts)Nous arrivons en 2026 avec des projets plein la tête, des ambitions encore plus grandes que l'année dernière, et surtout avec l'envie brûlante d'avancer et de progresser avec vous, ensemble. Merci pour votre soutien inconditionnel. Vos retours, vos partages, la force que vous nous donnez tous les jours sur les réseaux sociaux nous poussent et nous obligent à tout faire pour être à la hauteur. Continuez de diffuser GDIY partout, de partager nos épisodes à vos amis, à votre famille, c'est le meilleur cadeau que vous pouvez leur faire pour bien démarrer l'année ! On vous remercie une nouvelle fois pour cette année de dingue et on vous embrasse fort, La team GDIY.TIMELINE:00:00:00 : Bilan de cette année de folie00:12:44 : Ce qui nous a choqué en Chine00:15:34 : Le démarrage au quart de tour de “Combien ça gagne ?”00:19:11 : Pourquoi une nouvelle identité visuelle ?00:20:39 : On dévoile un nouveau podcast00:26:20 : L'immense succès de la série CAC 4000:30:00 : Les épisodes pépites de l'année00:45:39 : Nos ambitions folles pour 202601:00:10 : Les meilleurs apprentissages de l'année01:05:09 : Les livres qui nous ont marqué01:10:07 : MERCI 2025Les anciens épisodes mentionnés : #440 - Thomas Jolly - Metteur en scène, directeur artistique - Créer la plus grande cérémonie de l'histoire#441 - Arthur Benzaquen - Masada, réalisateur - Qui a dit que le business n'était pas artistique ?#444 - Charlie Dalin - Skipper - 64 jours pour faire le tour du monde : Nouveau record du Vendée Globe#448 - Owen Simonin (Hasheur) - Flirter avec les interdits puis devenir l'homme de confiance de la crypto en France#458 - Eddy de Pretto - Artiste - Contre vents et marées#460 - Riss - Charlie Hebdo - Toujours se battre pour la liberté#461 - Sébastien Bazin - PDG du groupe Accor - Diriger un groupe coté en bourse sans ordinateur#470 - Maurice Lévy - Publicis - Faire de la publicité son empire#473 - VO - Brian Chesky - Airbnb - « We're just getting started »#478 - Octave Klaba - OVH - La guerre du Cloud commence#479 - Nikola Karabatic - Champion de Handball - 22 titres sur 23 : la légende du sport français#480 - Esther Perel - Psychothérapeute - Comment réparer l'atrophie sociale avec l'experte mondiale des relations humaines#483 - Carlos Ghosn - Out of the box : masterclass business de l'évadé du siècle#487 - VO - Anton Osika - Lovable - Internet, Business, and AI: Nothing Will Ever Be the Same Again#488 - Valentin Kretz - L'Agence (immobilier de luxe) - Le vrai business des Kretz derrière la série Netflix#495 - Anne-Laure Constanza Gorgé - Toulemonde Bochart - “Je me suis battue dans un seul but : mettre à l'abri mes enfants”#505 - Mingpo Cai - Cathay Capital - De la chine profonde aux sommets du capital-investissement#507 - Laurent Alexandre - Vers la fin des études supérieures ?#510 - Carole Benaroya - Kujten - La reine du cachemire#512 - François Ruffin - Député - En finir avec l'État perfusion#513 - VO - Jesper Brodin - IKEA - A $40 billion revenue empire built with no bank loansNos recommandations de lecture :La Chine ou le réveil du guerrier économique, de Ali LaïdiPour le succès des armes de la France, de Pierre de VilliersBelle du Seigneur, d'Albert CohenClear Thinking, de Shane ParrishL'urgence et la patience, de Jean-Philippe ToussaintL'homme qui plantait des arbres, de Jean GionoThe Road Less Travelled, de M. Scott PeckLe déclin du courage, d'Alexandre SoljenitsyneVous souhaitez sponsoriser Génération Do It Yourself ou nous proposer un partenariat ?Contactez mon label Orso Media via ce formulaire.Hébergé par Audiomeans. Visitez audiomeans.fr/politique-de-confidentialite pour plus d'informations.

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

This year delivered whiplash: geopolitics, tariffs, and technology all shifting at once. And heading into 2026, the disruption isn't easing up. In this special episode, host Bob Safian distills five hard-won lessons from Rapid Response this year on how to lead when the ground won't stop moving. You'll hear standout moments from Brian Chesky, Clara Shih, Marc Lore, José Andrés, and more, with practical takeaways for turning uncertainty into advantage.Visit the Rapid Response website here: https://www.rapidresponseshow.com/See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This year delivered whiplash: geopolitics, tariffs, and technology all shifting at once. And heading into 2026, the disruption isn't easing up. In this special episode, host Bob Safian distills five hard-won lessons from Rapid Response this year on how to lead when the ground won't stop moving. You'll hear standout moments from Brian Chesky, Clara Shih, Marc Lore, José Andrés, and more, with practical takeaways for turning uncertainty into advantage.Visit the Rapid Response website here: https://www.rapidresponseshow.com/See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Liderar uma startup não é o mesmo que gerir uma empresa tradicional. O founder encara o caos, toma decisões sem manual e carrega uma responsabilidade existencial pelo negócio — tudo isso enquanto transforma energia em dinheiro.Neste episódio solo, Pedro Waengertner, CEO da ACE Ventures, explora o que torna a liderança do fundador tão única e por que muitos conselhos de gestão simplesmente não funcionam em contextos empreendedores. A partir de referências como Paul Graham e Brian Chesky (Airbnb), ele compartilha reflexões sobre quando o founder deve se envolver e quando deve, sim, jogar o manual fora.Você vai entender:As diferenças entre fundador, gestor e operadorOs seis perfis de foundersQual combinação desses perfis mais contribui para o crescimento de uma startupPor que autobiografias ensinam mais que playbooksComo usar IA para escalar sua atuação como founderSe você está na linha de frente de um negócio, esse episódio é um lembrete poderoso de que sua visão não é um detalhe — é o que dá vida à empresa.Dá o play e vem com a gente!Materiais mencionados:The Science of Startups: The Impact of Founder Personalities on Company Success — Paul X. McCarthyBefore the Startup — ensaio de Paul Graham (blog post) sobre os desafios de empreender.

Register here for Founder University Japan's Kickoff

Register here to join Founder University Japan's kickoff: https://luma.com/cm0x90mkToday's show:Google and Meta had their cases dismissed (or received a slap on the wrist)… Despite all the backlash and cynicism, AI companies continue making bank and releasing hot new products… What does it all mean?For Jason Calacanis, the signs are pointing to a “major M&A moment,” with huge opportunities for increased efficiency and consolidation among America's favorite brands and largest companies?Who will it be? Join Jason and Alex for a round of hot speculation.PLUS why Jason thinks Michael Burry is both right and wrong about GPU depreciation, why NOTHING is certain about these OpenAI mega-deals, Google's Nano Banana Pro can make infographics and they're VERY impressive… and much more.Timestamps:(1:54) Jason's calling in from Vegas… He's doing a hot lap at F1!(3:18) How restaurants are becoming the new Hot IP(6:50) Founder University is heading to TOKYO!(9:27) Why Jason thinks the future of startups is truly global(10:06) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at pipedrive.com/twist(11:39) Nvidia killed it on the numbers… but what are the vibes around AI? Jason sounds off.(13:05) Why nothing is certain when it comes to the Nvidia/OpenAI deal(19:40) Is Google now WINNING consumer adoption of AI? How did it get this close?(19:57) 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.(26:07) Meanwhile, AI apps are still dominating the iOS Store(27:09) Why Jason and Alex think Michael Burry's both right and wrong about GPU depreciation(30:13) 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!(37:46) We're testing out Nano Banana Pro on a BBQ infographic challenge(43:42) What a week for AI models! It doesn't seem like things are slowing down…(46:12) Kalshi is growing fast, but can it catch Polymarket?(47:50) Is a rate cut coming? Jason and Alex read the tea leaves.(50:13) Why Jason predicts a “major M&A moment” in the next six months(52:09) VIEWER QUESTION: What should a software engineer be working on RIGHT NOW.(54:02) Founder Friday is now… STARTUP SUPPER CLUBSubscribe 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:(10:06) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at pipedrive.com/twist(19:57) 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.(30:13) 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!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

AI Model Showdown: Grok 4.1 vs. Gemini 3 | E2211Register for Founder University Japan's Kickoff! https://luma.com/cm0x90mkToday's show:*Will the arrival of two hotly-anticipated, intensely powerful AI models snap the Doomer cycle?On a new TWiST, Jason and Alex consider the current AI landscape, one where cynicism about insider mega-deals, fear of job displacement, and concerns about bubble bursts seem to rule the day. Will the arrival of two powerful new models — xAI's Grok 4.1 and Google's Gemini 3 — help the industry to course-correct? And how do we decide how much these models have improved anyway?PLUS we're investigating Cloudflare's recent downtime and their acquisition of Replicate. Are we heading toward a future in which everyone runs their own models, locally? And how worried should founders get if their products or sites go down for a few hours?Finally, if you're an investor, and want to come to Jason's Dim Sum Demo Day in San Francisco, here's the link: http://launch.co/dimsumTimestamps:(2:01) Why the internet got broadly degraded when Cloudflare went down(5:00) How worried should founders become when their sites go offline?(6:44) Downtime aside, what did Cloudflare want with Replicate?(8:12) Why Jason predicts one day we'll run our own local language models(9:39) Goldbelly - Goldbelly ****ships America's most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.(15:25) How to turn off “Learn From This App” on your iPhone(17:29) Will the arrival of hotly-anticipated new models stop the spread of Doomerism and AI cynicism(20:00) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.(23:53) Checking back in with the “Best AI Model” Polymarket… why has ChatGPT dropped so low?(29:43) Zite - Zite is the fastest way to build business software with AI. Build apps, forms, websites and portals that connect to the tools you already use. Go to zite.com/twist to get started.(31:14) ANOTHER AI mega-deal? Nvidia and Microsoft are investing in… ANTHROPIC(33:06) Why so many AI deals now include “up to…” language around investments(35:04) What Jason thinks of Dario Amodei's warning about white collar job displacement(39:39) If we all agree AI job displacement is coming… what can be done?(45:16) All about Jason's Dim Sum Investor Demo Day in San Francisco!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:(9:39) Goldbelly - Goldbelly ****ships America's most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.(20:00) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.(29:43) Zite - Zite is the fastest way to build business software with AI. Build apps, forms, websites and portals that connect to the tools you already use. Go to zite.com/twist to get started.Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls “column B” thinking: building toward a dream future rather than just using the bricks around you.We discuss:1. How “column B” thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints2. The power of setting “crazy big goals”3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch5. Canva's “two-step plan”: build one of the world's most valuable companies, then do the most good possible6. Melanie's vision for 2050 and why she believes imagination is the first step toward a better world—Brought to you by:Vanta—Automate compliance. Simplify security. https://vanta.com/lennyStripe—Helping companies of all sizes grow revenue: https://stripe.com/Justworks—The all-in-one HR solution for managing your small business with confidence: https://ad.doubleclick.net/ddm/trackclk/N9515.5688857LENNYSPODCAST/B33689522.424104489;dc_trk_aid=616485033;dc_trk_cid=237010502;dc_lat=;dc_rdid=;tag_for_child_directed_treatment=;tfua=;gdpr=$—Transcript: ⁠https://www.lennysnewsletter.com/p/the-making-of-canva⁠⁠—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation—Where to find Melanie Perkins:• X: https://x.com/melaniecanva• LinkedIn: https://www.linkedin.com/in/melanieperkins/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Melanie Perkins and Canva(04:44) Building a “column B” company(06:36) Operationalizing big visions(13:13) Crazy big goals and celebrations(22:00) Challenges and setbacks in Canva's journey(26:30) Fundraising and investor rejections(29:36) Leadership and growth lessons(34:38) Canva's goal-driven structure(35:46) Balancing work and personal life(38:02) Community-driven product development(40:37) The two-step plan for global impact(45:04) Canva's biggest launch yet(48:10) How Canva approaches product expansion(52:37) AI integration in Canva(53:56) AI corner(55:22) Melanie's vision for 2050 and beyond(01:00:07) Lightning round and final thoughts—Referenced:• Canva: https://www.canva.com/• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa• UserTesting: https://www.usertesting.com/• Figma: https://www.figma.com/• Adobe: https://www.adobe.com/• Calm: https://www.calm.com/• Gandhi's quote about happiness: https://www.brainyquote.com/quotes/mahatma_gandhi_105593• Help us improve Canva: https://www.canva.com/help/get-in-touch/general-feedback/—Recommended books:• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/• The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898/• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765• Designing the Obvious: A Common Sense Approach to Web and Mobile Application Design: https://www.amazon.com/Designing-Obvious-Common-Approach-Application/dp/0321749855—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Today's show:*Why rebrand an app with 40 million daily active users?On TWiST, Grammarly CEO Shishir Mehrotra swings by to explain why he's renaming his company after the mail app he just purchased, Superhuman.Plus he's giving us a first look at the startup's new AI assistant, Superhuman Go, digging into their new agent-centered strategy, looking ahead at the potential for AI job displacement, and more.Jason and Alex also talk about our new nuclear deal with Westinghouse and Japan, OpenAI's conversion and what it means for Microsoft, 1x's tele-operated Neo-bot for chores, and much more!Timestamps:(00:07:56) Jason is headed to Tokyo, and NOT just for skiing this time!(10:00) 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(00:12:21) Untangling this US government-Japan-Westinghouse deal for nuclear power… and why nuclear power is SO important(20:00)DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twist(00:20:04) Why Jason says sabbaticals and 4 day work weeks are for established brands, not startups(30:00) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.(00:33:01) Will income inequality become a concern, even for the wealthy? Jason says YES.(00:37:29) Shishir Mehrotra from Gram— NO WAIT, Superhuman! joins us to talk name changes(00:38:16) Using Grammarly as a model for the new AI assistant, Superhuman Go.(01:08:39) Nvidia shot past $5 TRILLION in value… How is no one freaked out about this?!(01:14:52) OpenAI executed their conversion… but Jason says “public benefit corporation” status is pretty meaningless(01:25:02) Checking out the Neo robot from 1x… he wants to help you with chores and he's for sale!(01:32:09) Uber's speeding up its self-driving plansSubscribe 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:Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twistUber AI Solutions: Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/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

Today's show:Jason's been skeptical on Apple lately, but he's BLOWN AWAY by his new iPhone Air.Hear why JCal thinks Cupertino's latest release is “completely inspiring,” and why he's sure it's the next step on the road to Apple Glasses.We're chatting with LAUNCH founder Zach Handshoe of spacial video startup SpatialGen about designing products for Cupertino AND the intense pressure of performing a Steve Jobs-level keynote.PLUS Raiza Martin of Huxe stops by to tell us why they're using audio to make AI assistants more personalized AND proactive, and how they're already getting noticed in an increasingly crowded App Store.AND we've got another Gamma Pitch Competition entrant! Chess Grandmaster Vasif Durarbayli presents his expert-focused app, ChessEver.Timestamps:(2:05) Friend of the pod @ZacharyHandshoe stops by to talk about supporting Apple Immersive Video (and staying up during the AWS outage)(9:37) Enterpret - Turn 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.(15:55) The iPhone Air can already shoot spatial video! Just part of why Jason calls it a “completely inspiring” product.(21:25) Crusoe Cloud - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.(24:30) Jason offers viewers a peek inside LAUNCH's Whisper Network(32:09) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(33:10) Huxe co-founder (and NotebookLM vet) Raiza Martin wants to make your AI assistant more personalized and proactive.(37:14) Why Raiza and her team went with an audio-forward interface instead of a chatbot.(43:25) How Huxe is getting noticed in the App Store as a brand new arrival.(50:25) The big LLMs still aren't great at writing engaging content for humans, so Huxe is doing it themselves.(52:41) Chess Grandmaster Vasif Durarbayli from ChessEver joins us for his Gamma pitch!(54:26) Why Vasif is focusing on very serious players FIRST before appealing to more casual chess fans(1:05:28) Jason thinks ChessEver is at the moment of “triangulation” in their journey to finding Product Market Fit… what do Grandmasters really want?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:Enterpret - Turn 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.Crusoe Cloud - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/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

Today's show:Australia has accused Microsoft of employing a dark pattern… Hear why Jason says these kinds of sneaky tactics aren't usually worth it.It's a brand-new Monday TWiST and it's PACKED with news. In addition to Australia's allegations against MSFT, we're looking at Chinese drone fails and wondering how live experiences will change in the age of AI.PLUS has Tesla finally “solved” FSD after years of promises? Does it matter that so much of Mercor's revenue goes back out to contractors? Do Chinese LLMs have a major advantage when it comes to the stock market over Western counterparts? Why Jason avoids overseas deals when he doesn't speak the language or know the culture. And much more!Timestamps:(00:03:44) Fall is here! And Jason is already looking ahead to “BFCM” and the holiday season.(00:07:13) We're bringing back the TWiSTies and a Prediction 2026 show(00:07:33) People are using AI to create fake receipts for fraudulent invoices!(10:00) Pipedrive - Bring clarity and control to your sales process with Pipedrive, the #1 CRM for small and medium sized businesses. Supercharge your sales today. Start with a 30-day free trial at pipedrive.com/twist.(00:14:23) It's earnings week for Meta AND Alphabet AND Microsoft AND AMAZON!(00:19:55) What happened with the disastrous Chinese drone and fireworks show?(20:00) Monarch - Thanks to our partner, Monarch! Try the app and get 50% off your first year by visiting monarchmoney.com/twist.(00:27:37) Why Jason thinks live experiences are going to get much bigger and more impressive in the age of AI(00:29:34) Why Tesla is training FSD on synthetic data now… Has FSD finally been “solved”?(30:00) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits(00:45:10) What's going on with these new Sequoia funds? Jason unpacks the strategy…(00:50:50) Jason doesn't like to invest overseas unless he speaks the language and knows the culture(00:51:11) Jason's thoughts on the controversy surrounding Sequoia partner Shaun Maguire's comments(00:58:34) Mercor pays out 60-70% of its toppling revenue to contractors… does this MATTER?(01:06:14) Do Chinese LLMs have a major advantage when it comes to investing? (Humans are now betting on all this on PolyMarket)(01:09:45) Australia alleges that Microsoft is employing a dark pattern… why Jason says that's a problem.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:AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/creditsMonarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWISTPipedrive - Bring clarity and control to your sales process with Pipedrive, the #1 CRM for small and medium sized businesses. Supercharge your sales today. Start with a 30-day free trial at pipedrive.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

Today's show:*Working from 9 am to 9 pm, 6 days a week, might seem like TOO INTENSE a commitment for some, but Jason argues that elite performance — and the mega-compensation that goes along with it — sometimes requires personal sacrifice. While 72-hour weeks might lead to burnout for some, it really comes down to individual choice.PLUS Jason and Alex deep dive the NBA gambling scandal and the sketchy reality behind high-stakes home games of poker. PLUS Presh Kumar takes us behind the scenes, to see how AI apps helped him develop and workshop the video for his new wellness startup, Tempo, and what's with Anthropic buying chips from their AI rivals, Google? It's a can't miss This Week in Startups.Timestamps:(00:06:49) Jason and Alex are poker fans… what do they think about this insane NBA gambling scandal?(10:00) 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.(20:00) Nexos.ai - Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at https://nexos.ai/twist.(00:25:09) Is working “9-9-6” a reasonable goal? A guarantee of success? Why Jason compares it to being an Olympian.(30:00) Every.io - Running a startup is hard enough. Every takes care of incorporation, banking, payroll, benefits, accounting, taxes and more so that you focus on building, not back-office admin. Visit every.io.(00:38:00) Our old buddy Presh walks us through the process of making his Tempo launch video(00:42:28) Jason and Alex check out some of Ridley Scott's famous storyboards(00:48:03) Anthropic is buying TPUs from Google… Are these companies in LIKE with each other?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: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.Nexos.ai - Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at https://nexos.ai/twist.**Every.io -** Running a startup is hard enough. Every takes care of incorporation, banking, payroll, benefits, accounting, taxes and more so that you focus on building, not back-office admin. Visit every.io.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

Today's show:*Amazon's dropping a LOT of employees for AI and robots… are Jason's darkest predictions coming true?Legendary investor Elad Gil joins Jason and Alex for the full show today! Together, they're digging into the Amazon news, looking back at Jason's predictions from just last month, and theorizing about just how many people will lose their jobs to computers, and what we're going to do about it. (Is it possible the US hasn't been massively hit by job displacement so far because those gigs already moved overseas?)PLUS… Anthropic's Dario Amodei responds to criticisms from JCal's bestie David Sacks, Sesame emerges from stealth to work on AI wearables, and where will people in the future interact with their favorite apps? A headset? Phones? Somewhere else? The great debate continues.Timestamps:(00:04:04) Our guest is iconic angel investor Elad Gil! What's he working on…(00:04:54) Alexandria AI translates public domain books into all commonly spoken languages… Do people actually prefer AI translations?(00:09:16) Why compute tends to centralize over time… (It's because of economies of scale!)(00:09:29) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(00:12:49) So are we building TOO MANY datacenters? Will AI apps eventually run on your phone anyway?(00:16:39) Jason says “The Age of Efficiency is upon us.”(00:19:24) When companies trade inference for market share(00:19:27) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(00:21:57) Why one of the main challenges of adopting AI is buy-in and convincing teams to use it.(00:25:47) Elad's robotics questions: (1) What % of winners will be incumbents?(00:27:50) Jason called the Amazon news last month and we have the receipts!(00:29:36) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first yea(00:45:33) Jason says Adobe and Figma should abandon the UK entirely.(00:45:55) Time for a Polymarket: The sharps say 80% chance Tesla beats their quarterly earnings(00:51:02) What is Sesame? They just emerged from stealth, they raised $250M, and they're working on AI wearables.(00:53:21) Jason has concerns about AI wearables that are always recording… Does Elad share these concerns?(01:03:17) The crypto industry is now one of the largest purchasers of US government debt… what does that mean? Who owns who?(01:08:53) Anthropic responded to JCal's Bestie David Sacks… Is Dario Amodei a doomer? Fearmongering?(01:19:12) Why Jason thinks AI companies need to self-regulateSubscribe 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:Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTSentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWISTPilot - Visit https://www.pilot.com/twist and get $1,200 off your first yeaGreat 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

Are AI tools in the classroom just time-savers, or can they have genuine educational value?In a must-watch TWiST 500 interview, Alex chats with Magic School founder (and former principal) Adeel Khan about how AI tools can make teachers more effective, and keep students inspired, without just doing all the work for them. He talks about turning an AI chatbot into a true assistant teacher, that keeps the lessons balanced yet challenging, and particularly empowers classroom novices and non-professionals.THEN… is 6 years too long for employees to wait to vest? Is this just another founder trying to reinvent EVERYTHING, just because they can't resist? Ramp CEO Eric Glyman joins Jason and Alex to answer pressing founder questions from viewersPLUS there's a new entrant in our Gamma Pitch Deck competition, and it's so compelling, Jason can't wait to invest! Kris Canete of On the Fly Energy tells us about America's fragile power grid and his elegant solution: flywheel energy storage!Timestamps:0:00 - Welcome to TWiST!02:59 - Former principal Adeel Khan of TWiST 500's Magic School AI tells us why “teachers are magic”09:41 - Goldbelly ships America's most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.10:50 - How AI tools can particularly help out classroom novices and non-pros who are just getting started20:57 - 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.26:58 - How Magic School stays ahead of shifting standards across different states and regions32:57 - Zite is the fastest way to build *business software* with AI. Build apps, forms, websites and portals that connect to the tools you already use. Go to *zite.com/twist* to get started.33:30 - Why the best feedback Adeel ever got came from a teenager36:30 - Making AI a true assistant teacher, that keeps lessons balanced yet challenging38:38 - Is a 6-year vesting schedule too aggressive? Eric Glyman responds.41:00 - When even ambitious founders should sometimes just accept a standard deal.57:33 - What IS flywheel energy storage?01:00:00 - Why Jason loves the Fly Energy Gamma pitch and wants to invest right now.01:34:13 - Gamma Outro*Subscribe to the TWiST500 newsletter: [https://ticker.thisweekinstartups.com](https://ticker.thisweekinstartups.com/)Check out the TWIST500: [https://www.twist500.com](https://twist500.com)Subscribe 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: [⁠  / alexwilhelm  ](  / alexwilhelm  )*Follow Jason:X:   / jason  LinkedIn: [  / jasoncalacanis  ](  / jasoncalacanis  )Great TWIST interviews: [Will Guidara,](   • Lessons in Unreasonable Hospitality with W...  ) [Eoghan McCabe](   • Great Builders & Success First with Interc...  ), [Steve Huffman](https://podcasts.apple.com/us/podcast..., [Brian Chesky](https://podcasts.apple.com/ca/podcast..., [Bob Moesta,](   • Decoding Customer Insights, Trust, and the...  ) [Aaron Levie](https://podcasts.apple.com/ca/podcast..., [Sophia Amoruso](https://podcasts.apple.com/ca/podcast..., [Reid Hoffman](https://podcasts.apple.com/ca/podcast..., [Frank Slootman](https://podcasts.apple.com/ca/podcast..., [Billy McFarland](https://podcasts.apple.com/ca/podcast...)*Check out Jason's suite of newsletters: https://substack.com/@calacanis*Follow TWiST:Twitter:   / twistartups  YouTube:    / thisweekin  Instagram: [  / thisweekinstartups  ](  / thisweekinstartups  )TikTok:   / thisweekinstartups  Substack: [https://twistartups.substack.com](

The NHL has inked an official partnership with Kalshi and Polymarket, marking the first time a major sports league has teamed up with prediction markets. Kalshi co-founder and CEO Tarek Mansour discusses his platform's sports volumes, potential regulatory issues, and competition with sportsbooks. Airbnb has launched new products and features to remake user vacations, and CEO Brian Chesky is just getting started. Chesky discusses the future of his company and the impact of AI. Plus, Netflix streamer numbers missed expectations, Mattel's Barbie sales are down, and Meta has partnered with Blue Owl on a data center.  Tarek Mansour - 19:20Brian Chesky - 27:39 In this episode:Tarek Mansour, @mansourtarek_Joe Kernen, @JoeSquawk Becky Quick, @BeckyQuickAndrew Ross Sorkin, @andrewrsorkinKatie Kramer, @Kramer_Katie Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Deel's growth overshadows SpyGate, Claude learned new skills, and the great “momentum is moat” debate | EXXXToday's show:*Deel's growing fast enough that investors are overlooking the espionage allegations and jumping on board anyway. (LAUNCH now owns a lil taste of Deel, so Jason is on board!)PLUS is the Mag 7 about to become the Mag 70… Why legendary investor Roelof Botha thinks VC is not an asset class… How startups can use capital as a weapon… AND Anthropic gave Claude more skills, which they hope will help pay their bills.Timestamps:(00:01:34) Jason's excited for ski season and checking his favorite powder app, OpenSnow(00:04:02) Why Jason's done with meetings; he's pulling a Doug Leone!(00:06:27) Jason can tell the market's heating up because people are starting to lose their minds.(00:09:31) How much will global AI tools one day be worth? Alex is crunching the numbers.(10:00) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!(00:15:22) PREDICTION: The Mag7 is about to become the Mag70(20:00) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist(00:25:36) Deel's big raise… Why major growth overshadows spying allegations(30:00) 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.(00:33:31) Why Roelof Botha says VC is a “return-free risk,” and not an “asset class.”(00:40:49) The two reasons why VC firms end(00:44:18) How startups can use capital as a weapon(00:57:52) Anthropic gave Claude Skills to pay the bills(01:00:51) Jason's vision for what Grammarly could becomeSubscribe 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:Miro - Help your teams get great done with Miro. Check out miro.com to find out how!Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at 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.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

Today's show:*On a very special TWiST, Jason's joined by “one of the greatest investors in in the history of VC,” Steve Jurvetson of Future Ventures.Together, they look back at some of Steve's earliest investments and learnings, the promise and ultimate failure of nanotech, breaking down the AI hype cycle, the primacy of neural networks, the return of nuclear power, why “AI safety” might be illusory, and much more.It's a packed show full of deep insights from one of the greatest minds in technology today. Do not miss this ep!Timestamps:(00:00)Jason's 1-on-1 today with “one of the greatest investors in the history of VC,” Steve Jurvetson(00:03:04) The early origins of Steve's fascination with “deep tech”(00:08:03) Jason and Steve recall playing around with the TRS-80 (“The Trash-80”)(10:00) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.(00:15:13) Keeping your portfolio diverse when so many companies look the same(20:00) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(00:20:49) The promise of nanotech and why it fell apart(00:25:46) Breaking down the “hype” cycle and how trends get co-opted(00:26:27) Why Moore's Law and the Power Law are so important for investors(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 https://www.northwestregisteredagent.com/twist today!(00:33:36) Understanding the rise of GPUs and how they resemble tiny brains(00:51:32) Revisiting a classic clip of Steve talking about robots(00:54:04) How Jason and Steve got their hands on some of the earliest Tesla Roadsters(01:00:09) Flashback Clip: Elon predicts 2025 in 2015… how'd he do?(01:02:46) Why did the world turn SO strongly against nuclear energy?(01:16:06) Can we make AI “safe” in the age of GPT Psychosis? Is it too inscrutable?(01:21:54) Why Steve thinks technology will ultimately doom autocratic regimes.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:TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.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!Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/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

Amid dramatic disruption, what role should business play in building the future? Recorded live at the 2025 Masters of Scale Summit in San Francisco, Airbnb co-founder and CEO Brian Chesky shares his candid perspective on business, politics, creativity, and AI — taking listeners from Airbnb's humble beginnings to bold plans for the company's future. Through a designer's lens, Chesky also reveals the single question leaders must ask themselves, and explores how best to make tricky decisions in a volatile climate. Visit the Rapid Response website here: https://www.rapidresponseshow.com/See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today's show:*Eric Glyman of Ramp joins us to share the fintech unicorn's growth secrets AND their Lab full of research data.On TWiST, Jason and Alex chat with Eric about Ramp's counter-intuitive mission — helping startups spend LESS money — PLUS they take a deep dive into the company's treasure trove of startup trend data. Why is there a huge spike in unemployed recent college trends? Is “static team size” as a big a story as Jason and Alex think? What does it actually take to get companies to adopt AI Agents? The answers all might be in these Ramp numbers.PLUS Eric joins us for some hot Founder Q's, and what's going on with all this Y Combinator drama? We're sifting through the angriest tweets for the inside scoop.FINALLY, Jason recommends some of his favorite startup accelerators of the moment (aside from his own) including…PearXArc from SequoiaAntlerSpeedrun from a16zTimestamps:(00:02:18) The 72-hour rule strikes again: Trump's China's tariff reversal(00:03:10) Why crypto got hit even HARDER than the stock market post-Trump announcement(00:07:32) Market manipulation “at a scale we've never seen before…”; what does this mean for everyday investors?(10:05) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(00:12:55) Ramp CEO Eric Glyman swings by to update us on his fintech unicorn's growth and their “Lab” for research data(20:09) Netsuite - Download the ebook CFO's Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(00:21:40) Is “static team size” a real trend? What the Ramp data shows…(00:26:25) Ramp's “counter-intuitive” mission: to help companies spend LESS money, not more.(30:24) Paper OS offers the largest library of AI-driven Workflows for both founders & fund managers. Claim your $10K credit at paperos.com/twist(00:38:07) WHY the huge spike in unemployed recent college grads? Especially among the guys?(00:49:16) What it actually takes to get companies to adopt AI agents into their processes(00:52:25) Why Jason thinks Eric is a top-tier TWiST guest. We're going through the metrics…(00:54:05) There's YC drama on social media now… we're spilling the tea.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:Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTNetsuite - Download the ebook CFO's Guide to AI and Machine Learning for free at https://www.netsuite.com/twistPAPER OS - Building an empire? PaperOS offers the largest library of AI-driven Workflows for both founders & fund managers. Whether you're raising capital, launching a fund, or wading through diligence, PaperOS unlocks simplicity and scale for your ever-growing empire. Claim your $10K credit at paperos.com/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

Today's show:*Zach Dell of Base Power joins us at the top of today's show to talk about building batteries in Austin, that $1 billion investment, and why an “all of the above” energy strategy is the only way forward.PLUS Jason and Alex's thoughts on that Tesla non-upside down car announcement, growing resentments toward AI datacenters, Chinese robots actually going on sale, Tim Cook's potential Apple exit, xAI's Nvidia agreement and MUCH MORE.Timestamps:(00:02:10) A MAJOR GUEST! Zach Dell of Base Power joins us from the top of the show.(00:03:31) The basics of Base Power's business model: the best electron is the cheapest electron(00:08:38) Zach teases Base's new, time-saving approach to battery installation(00:10:32) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(00:18:12) How Base's grid can help drive down overall energy prices(00:21:17) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(00:30:12) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(00:36:20) Tesla did not announce an upside fan car… Oh well…(00:44:27) Buy your Chinese robot TODAY on Walmart dot com? Or not!(00:48:12) Is Tim Apple EXITING Apple? Who's next?(00:59:22) ANOTHER mega-deal? Now xAI is circling a Nvidia investment…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:Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twistSquarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTSentry - New users get 3 months free of the Business 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

Today's show:*How many weirdly circular mega-deals is OpenAI going to sign this year?On a new TWiST, Jason and Alex consider OpenAI's latest agreement with AMD, how the biggest American companies keep trading cash and chips back and forth, and whether or not the entire AI economy might be a house of cards.PLUS what kind of fan/leafblower tech is Tesla working on… what can Jevons Paradox tell us about the AI landscape… how easy is it to master games in the YC Arena… and WHY has NASA never built a base on the moon? We're asking the TOUGH QUESTIONS so you don't have to, only on the #1 tech podcast, “This Week in Startups.”Timestamps:(0:00) Jason and Alex open the show discussing hunting and traditional Texas meat exchanges(2:16) ANOTHER weirdly circular OpenAI mega-deal? How many mega-deals can one company MAKE?(3:50) Are all these “bizarre” OpenAI deals creating a house of cards?(10:00) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.(20:00) Oracle - Try OCI and save up to 50% on your cloud bill at https://oracle.com/twist⁠⁠⁠(21:14) Is the Tesla Roadster 2 coming soon? Or maybe a leaf blower?!(22:00) Datacenters in space! Is it getting crowded up there?(26:22) Why no moon base yet? Jason demands a moon base.(27:00) We're playing games in the YC Arena… Can Jason guess which pitches got accepted?(30:00) Coda - Empower your startup with Coda's Team plan for free—get 6 months at https://www.Coda.io/twist(32:00) How Jason picks companies to invest in, based on a few signals and metrics(04500) We found out what Figure's bots are actually doing for BMW(53:00) Sharpies figured out how to make their pens here in the US… who's next?!(57:00) Could ChatGPT really replace Deloitte consultants? Considering the latest controversy…(01:03:29) It's another Gamma Pitch: Welcome Ryan Yannelli of NextVisit AI, which helps therapists take notesSubscribe 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:Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.Oracle - Try OCI and save up to 50% on your cloud bill at https://oracle.com/twist⁠⁠⁠Coda - Empower your startup with Coda's Team plan for free—get 6 months at https://www.Coda.io/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

Today's show:Is Sora not just a copyright-killer but a TikTok-killer? Hear our review!The “This Week in Startups” team has been playing around inside OpenAI's viral app, which just hit #1 in the iOS Store. See all of Lon's creations, explore the land beyond the Uncanny Valley, and find out why the hottest new social app could stand to be a bit more social.PLUS Brave surpasses 100M MAUs… why Jason would sell ALL his OpenAI shares right away, Apple pulls the ICEBlock app from the App Store, AND how one founder hacked his local coffee shop to network and even get face time with a few VCs! It's all happening of a fast-paced Friday TWiST.Timestamps:(0:00) Why Jason started an Executive Training program at LAUNCH(05:17) Perplexity's Comet browser is now FREE to use; Jason unpacks their strategy(10:02) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST(13:42) PLUS browser/search engine Brave passed 100M MAUs!(17:44) How a founder “hacked” his local coffee shop(20:06) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist(21:35) You need to make it EASY for people to give you feedback!(25:41) A look at the leanest startups around and how companies are doing more with less(30:11) LinkedIn Ads: Start converting your B2B audience into high quality leads today. We'll even give you a $100 credit on your next campaign. Go to http://LinkedIn.com/ThisWeekinStartups to claim your credit.(30:38) Why Jason would sell ALL his OpenAI shares right away!(38:56) Lon stops by to review the Sora app; the good, the bad, and the remixes!(48:45) Apple pulled the ICEBlock app… is this a free speech issue?(56:11) A new startup wants to fight gov't corruption… and keep a share of the proceedsSubscribe 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:Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWISTAlphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twistLinkedIn Ads: Thanks to our partner @LinkedInMktg. Start converting your B2B audience into high quality leads today. We'll even give you a $100 credit on your next campaign. Go to http://LinkedIn.com/ThisWeekinStartups to claim your credit.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

In this episode of WORK, Erika reflects on lessons from the Work Like a Girl event in Boston and why optimism may be the most powerful leadership skill. She then unpacks viral business stories, including the Applebee’s executive who went on to become CEO of IHOP and eventually bought Applebee’s, and Brian Chesky's (Airbnb CEO) reminder that the future waits for no one. Erika also breaks down the surprising stat that three in four Gen Z workers bring their parents into job interviews. Later, Jack Fischer, from the finance team at Food52, joins to share insights on building trust, challenging executive assumptions, and the importance of financial transparency at work. Finally, journalist and photographer Nadja Sayej discusses her career in the gig economy, the decline of traditional journalism, navigating celebrity culture, and how she’s building a creative legacy on her own terms.See omnystudio.com/listener for privacy information.