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Jason Calacanis

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

This Week in Startups

Register here for Founder University Japan’s Kickoff 👉🏻 https://luma.com/cm0x90mk

Today’s show:

The team from Familify had released a well-reviewed storytelling app for kids and parents… but it just wasn’t growing!

Then they noticed that Bible stories and faith-based content was particularly popular. So they decided released a brand new app, Theo, just for these sorts of lessons and stories. And the new product overtook Storybook in just a few weeks!

It’s a vital lesson for founders… Even if you succeed, you may be able to succeed EVEN MORE. Remain flexible and open to strong new ideas (especially if, like Francisco, your wife suggests them!)

PLUS we’re chatting with Collin from En Vérité about how AI can make do diligence much less painful for investors AND checking out our latest Gamma Pitch Deck competitor. Find out why Jason says Jake Triton from Pitch Prfct might just be closing in on Product Market Fit.

Timestamps:

(5:20) How Storybook, then Theo was motivated by a children’s mental health crisis

(5:46) Despite great reviews, Storybook wasn’t growing! Here’s what they did.

(7:13) The Power of Experiments: Theo overtook Storybook in popularity in JUST WEEKS

(10:04) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(11:04) Digging in to the decision to flip from all stories to Bible stories

(12:34) The difference in how users perceive prayer vs. meditation

(14:06) Will they make different Theos for different denominations of Christianity? Other faiths?

(14:55) Jason makes the case for the Theo app and its team

(19:59) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(21:50) Key lessons for founders from Francisco’s pitch today

(26:51) Collin Sebastian from En Vérité joins the show to tell us how En Vérité helps prepare founders for the due diligence process

(30:00) Enterpret: Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.

(31:03) Jason recalls some diligence horror stories from his past

(32:14) Where En Vérité gets their data and how they use it

(36:39) What Collin learned from his time at SoftBank

(39:44) The Gamma Pitch Deck Competition returns with Jake Triton from PitchPrfct [https://x.com/JakeTriton] @pitchprfctsms

(42:29) Why Jason thinks Jake is closing in on Product Market Fit

(45:51)How PitchPrfct plans to have AI help build your campaign and workflow

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.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/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(10:04) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(19:59) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(30:00) Enterpret: Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Even great startups sometimes need to pivot (feat. Francisco Cornejo of Theo) | E2214

Register here to join Founder University Japan’s kickoff: https://luma.com/cm0x90mk

Today’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 CLUB

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.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/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank 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 McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

Jason predicts a “major M&A moment” in the next six months! | E2213

Today’s show:

The race for more compute gets all the headlines, but Mistral AI CEO Arthur Mensch tells us the REAL danger is running out of data!

On TWiST, Jason and Alex are chatting with the head of France’s largest foundation AI company, Mistral AI, about how enterprises can get more out of their AI pilots, whether the West is lacking leadership on open-source, why Mistral AI isn’t pursuing every possible kind of AI application, and optimizing your models for performance rather than benchmarks (aka benchmaxxing). Find out what it’s like to run a huge AI company in today’s intense environment!

PLUS… why everyone made the wrong call on OpenAI vs. Google… Kraken’s fresh $20 billion valuation… Jason’s urgent message to every company thinking about M&A… and much more!

Timestamps:

(3:35) Why did everyone get it wrong on Google vs. OpenAI?

(10:51) Why Jason thinks drone delivery will make everyone safer

(9:52) SQUARESPACE: Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(11:26) Mistral AI CEO Arthur Mensch joins us! What’s it like to run a foundation model AI company in this intense environment?

(14:50) Why enterprises aren’t getting enough value out of AI and how Mistral AI aims to correct this

(18:45) Why Mistral AI’s goal is, ultimately, to disappear…

(20:19) 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.

(22:49) Are Europe and the US lacking leadership on open source AI?

(24:53) Mistral AI doesn’t need to compete in every category... how big of an advantage is focus?

(27:05) The “two bottlenecks” in Machine Learning: Compute and Data

(29:01) How Mistral AI works with human experts to annotate their models, and where they source them from

(30:06) 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.

(34:24) Is optimizing your model for benchmark tests (aka benchmaxxing) like cheating?

(40:08) Will we ever be able to run smaller AI models on our phones?

(44:21) When does Arthur think we’ll have truly helpful humanoid robots in our lives?

(49:42) Suno lawsuits and why Jason says you should NEVER break the rules, ESPECIALLY with the music industry

(54:28) Release the Kraken! They’re now worth $20 billion.

(56:48) Jason is going to F1… should he take up the offer and do a dry run?

(58:30) How Meta beat the FTC and why Jason is so excited about it

(1:01:37) Who should buy Crunchbase?

Why data is the biggest AI bottleneck (feat. Arthur Mensch of Mistral AI) | E2212

AI Model Showdown: Grok 4.1 vs. Gemini 3 | E2211

Register for Founder University Japan’s Kickoff! https://luma.com/cm0x90mk

Today’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/dimsum

Timestamps:

(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.com

Check out the TWIST500: https://www.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/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank 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

AI Model Showdown: Grok 4.1 vs. Gemini 3 | E2211

*Are we finally reaching Peak eVTOL? Jason and Alex on Joby’s big Abu Dhabi moves and Archer’s purchase of LA’s Hawthorne Airport.

On a PACKED Monday TWiST, Jason is BACK from MENA and Tokyo. Hear tales from his whirlwind trips launching new Founder University satellite programs… and find out why construction and fintech are BOOMING across the Middle East.

PLUS Ramp raised $300M… here’s why Alex calls the round “pretty baller.” We question why AI companies are growing SO MUCH FOUNDER than their SaaS counterparts. We’re digging into the Problem with Dropbox.

AND we’re saying goodbye to KitKat, the beloved SF bodega cat who was reportedly run over by a Waymo. Here’s why Jason’s not too broken up about it (but he’s JUST JOKING!)

👉 Register here for Founder University Japan’s kickoff: https://luma.com/cm0x90mk

Today’s show:

Timestamps:

(2:17) Big takeaways from Jason’s MENA Founder University trip

(6:54) Why construction and fintech are booming across the Middle East(9:56) Netsuite. The business landscape is very chaotic right now. That’s why you need NetSuite, by Oracle. Download the CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(12:35) Everything was very different at Founder University Japan! It’s coming in January.

(15:59) Ramp raised $300M at a $32B valuation… why Alex says it’s “pretty baller”

(17:15) Ramp says AI agents are making money more intelligent… the heck does that mean?

(19:26) We’re building more space for machines than humans now… and why Jason’s not sure this will last

(19:48) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(23:41) Why AI is growing SO MUCH faster than even top SaaS companies

(25:32) The Problem with Dropbox…

(30:21) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.DevStats.com/twist.

(32:39) Jason ate his way across Tokyo… here’s all the deets

(33:16) RIP KitKat, beloved SF bodega cat killed by a Waymo

(39:03) So who SHOULD get to make decisions about local roads?

(44:15) Dario Amodei from Anthropic shares Jason’s concerns about AI job displacement

(52:02) What’s going on with crypto prices? Is this vibe-based? Just based on the wider economy?

(58:14) Viewer questions: What strategies should founders employ in the current fundraising landscape?

(1:02:42) Bezos RETURNS to the C-Suite. What IS “Project Prometheus”?

(1:10:24) Jason thinks Bezos still returns to Amazon at some point… or runs for President.

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.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/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(9:56) Netsuite. The business landscape is very chaotic right now. That’s why you need NetSuite, by Oracle. Download the CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(19:48) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(30:21) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.DevStats.com/twist.

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

👉 Register here to join Founder University Japan’s kickoff: https://luma.com/cm0x90mk

Today’s show:

Nox’s new app RPLY reminds you to text your friends back, getting you to iMessage inbox zero.

On today’s TWiST, we’ve got Molly Cantillon of Nox, telling us how she plans to make lackadaisical texters (like our co-host Alex) more effective, even if it means breaking into Apple’s walled garden. Hear about how RPLY maps your relationships so that it can understand your messages contextually, and help you stay organized.

Then, Gregg Mojica of Alloy Automation swings by the show to dispel some common myths about AI agents. For the most part, these little machine learning helps aren’t truly autonomous… Hear how Alloy’s agents decide when it’s time to bring in a human for help. PLUS is AI in a “lull” right now? Hear why Gregg thinks there’s still a LOT of room for these apps to improve.

Finally, it’s another TWiST Flashback. We’re jumping back to 2013 for an eye-opening chat between Jason and Shopify founder/CEO Tobi Lutke. Hear some fascinatingly prescient takes on the rise of SaaS, how early Shopify differentiated itself from other ecommerce and website building solutions, AND why Tobi dreamed of making Ottawa a true tech hub.

Timestamps:

(02:57) Molly Cantillon of Nox is trying to help you get better at texting

(04:01) How RPLY gets even chaotic texters like Alex more organized

(05:10) The complexities of entering into Apple’s “walled garden”

(07:20) Keeping RPLY safe, in case you’re using it for work!(09:24) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(11:59) How RPLY uses relationship mapping to understand and prioritize your messages(19:23) Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.

(21:08) Why Nox wants its AI to become “the Invisible OS.”(29:30) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

(30:40) We’ve got Gregg Mojica of AI agent makers Alloy Automation

(31:42) How the rise of AI agents changed the core of Gregg’s business

(34:03) Why most AI agents still aren’t truly autonomous

(35:00) How Alloy’s agents decide when to bring in a human for help

(37:02) Why the rapid acceleration of AI development has made some enterprises pump the brakes

(39:00) Is AI in a “lull” right now? Why Gregg thinks there’s still room to improve.

(40:31) How close are we to AI apps going truly mainstream?

(43:41) Why Alloy Automation didn’t raise a massive round like so many of its AI peers? (Or are they?!)

(46:48) The difficulty of hiring in today’s AI landscape

(50:21) In today’s TWiST Flashback, we’re revisiting Tobi Lutke of Shopify’s appearance from way back in 2013!

(52:11) Why Shopify switched from selling snowboards to storefronts

(59:37) Turning Ottawa into a tech hub, and the “secondary market” theory

(1:05:32)The constant tension between growing your global footprint and expanding your features

(1:08:52)Who were Shopify’s actual rivals?

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

👉 Register here to join the kickoff: https://luma.com/cm0x90mk

Today’s show:

Just getting our stuff into orbit isn’t enough… Orbital Operations wants to help companies take things HIGHER.

In today’s TWiST 500 interview, Alex chats with Ben Schleuniger, whose startup Orbital Operations is solving the complexity of space logistics. The advent of reusable rockets has made it easier and cheaper than ever for us to place objects in Low Earth Orbit (or LEO).

But what if we want to reach higher orbits? That’s a much more challenging issue: space is already kind of CROWDED, and not all of our vehicles can carry enough fuel to power them that far out into the cosmos.

Orbital’s fix? Cryogenic orbital maneuvering vehicles (or OMVs) like the Astraeus, which uses hyper-efficient propulsion systems, allowing them to travel further and faster speeds, and even potentially get refueled in orbit.

Learn more about this fascinating tech PLUS we’re looking back at classic Jason interviews with Greg Brockman of OpenAI and Vlad Tenev of Robinhood, AND checking in with Oliver’s latest This Week in AI demo for Character AI’s blockbuster conversational chatbots.

Timestamps:

(02:56) Alex opens the show with Ben Schleuniger, co-founder of space tech startup Orbital Operations

(03:47) Why is movement within orbit such a challenging problem?

(4:28) The key importance of launch vehicle reusability

(07:05) How Orbital’s Astreaus vehicle utilizes cryogenic propellants… and why

(08:49) The secret to keeping those propellants cool

(10:04) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(13:57) How Orbital is preparing for their Series A, and how they plan to spend the cash(20:37) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!

(28:09) TWiST FLASHBACK: Revisiting OpenAI Greg Brockman’s visit from 2018

(31:31) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.

(37:57) How GPUs unlocked the AI revolution

(35:02) Tackling early concerns about deepfakes

(41:17) Looking ahead to the dawn of AGI

(50:05) AI DEMO: Oliver stops by to walk us through Character AI’s key features

(50:51) Watch as Oliver simulates a chat with former President Barack Obama

(53:30) How to use ChatGPT to enhance your Character AI prompts

(56:57) TWIST FLASHBACK with Robinhood’s Vlad Tenev from May 2017

(57:14) Back then, Robinhood was valued at a mere $1.3 billion!

(59:21) How Robinhood made financial transactions SO MUCH FASTER than they used to be

(1:00:57) When Robinhood realized they had Product Market Fit… via Hacker News!

(1:06:44) The magic of being better, faster, and cheaper

(1:08:12) This segment was filmed BEFORE Robinhood offered crypto

(1:11: 08) Jason’s Eagle Computer Speech and how to avoid “Taj Mahal Syndrome”

Check out the TWIST500: https://www.twist500.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/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Thank 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/TWIST

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!

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.

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

Register for Founder University Japan’s Kickoff! https://luma.com/cm0x90mk

Today’s show:

Find out why AI is perfectly suited to legal tasks… despite being too fast for “billable hours”

On today’s TWiST, Alex takes a deep dive into LLM Law with Harvey AI co-founder/president Gabe Pereyra. It turns out, much like software development, doing legal work relies on learning specialized language and sifting through a dense and expansive corpus of information… making it an IDEAL use case for LLMs.

Buuuuut AI works so fast… the current structure of legal payments (billable hours) no longer applies. Find out how Harvey is working around these challenges — and what they plan to do if OpenAI decides to get into the legal game — in this fascinating interview.

THEN, Alex chats with another AI visionary — OpenRouter co-founder and CEO Alex Atallah — who allows developers to plug and play all the major models into their applications. Find out why specialized LLMs trained for “resourcefulness” are coming into fashion… why benchmarks and evals have become so crucial to the industry… AND whether we’ll end up spending as much on AI inference as the human workers it’s replacing… in this essential discussion.

PLUS Jason stops by for some more Founder Q’s!

Timestamps:

(0:00) Welcome back to TWiST!

(1:32) Alex kicks off the show with Harvey AI co-founder and President Gabe Pereyra to talk about applying AI to the legal profession

(4:52) How major international law firms (and their enterprise clients) fueled Harvey’s mega-growth

(6:54) Why LLMs are perfectly suited for legal work

(9:24) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.x and build next. Head to Enterpret.com/twist to book a demo and see it in action.

(17:22) Looking ahead: expanding beyond the law.

(20:42) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist

(21:44) The problem: AI can’t charge “billable hours”… it’s too fast!

(23:44) Will the major AI players like Google and OpenAI build their own version of this?

(29:53) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(30:41) Alex welcomes OpenRouter co-founder and CEO Alex Atallah, whose rankings he loves and uses all the time

(33:10) Why Alex says we’re seeing more specialized LLMs trained for more “resourcefulness”

(36:05) How increased competition and diversification makes things tougher for developers

(41:09) Alex suggests that new models are exciting for users, like product launches used to be

(42:29) OK, let’s get into it… How does OpenRouter make money?

(45:38) Understanding what kinds of training data the AI companies want the MOST

(47:47) The important currency of evals and benchmarks

(49:13) Why OpenRouter is ramping up its LLM recommendation engine

(53:44) Will AI inference spend end up costing as much as the humans it’s replacing?

(56:49) Time for a Founder Q! What should founders do about quick vibe-coded competitors?

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

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Follow Lon:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Thank you to our partners:

(9:24) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.x and build next. Head to Enterpret.com/twist to book a demo and see it in action.

(20:42) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist

(29:53) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

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

👉 Register here for Founder University Japan’s Kickoff! https://luma.com/cm0x90mk

Today’s show:

*Three of our favorite TWiST 500 startups — Ledger, 1Password, AND Mercury — are circling IPOs. Find out why the cybersecurity space remains so hot… AND why Jason says you really need to have multiple banks.

PLUS Marc Andreessen called The Pope an AI Doomer on X, then thought better of it. We’re tracking the entire viral controversy…

SPEAKING OF viral feuds, allegations are FLYING around about recently-funded AI agent makers Giga. Does the startup pose some genuine red flags, or was it just a questionable launch video?

AND why Alex and Jason remain optimistic the AI vibes could turn around, presentation maker Gamma is growing FAST, plus an update on Jason and Alex’s Polymarket IPO wager…

Timestamps:

(02:17) Jason is hosting the big show from Tokyo today (tonight for him)… Where is Founder U headed next?

(04:03) Jason’s eating his way across Japan… what are his top “bang bangs” so far?

(07:47) Is The Pope a Doomer? Why Andreessen called out His Holiness (then deleted it)

(9:22) Quo - Streamline and scale your customer communications with OpenPhone. Get started free, plus get 20% off your first 6 months, at http://quo.com/TWiST

(12:08)Why Jason still thinks mass AI job displacement is coming

(17:48) Will AI-related job loss lead to an explosion in startups and small businesses?

(19:24) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist

(20:39) Have lots of Americans suddenly turned on AI Why?

(25:30) Why Alex and Jason remain optimistic that the AI vibes could turn around

(29:44) Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.

(31:01) Alex’s new favorite definition of Product Market Fit, or “Market Pull,” as Jason clarifies

(33:31) Delving into the Giga controversy… “ugly” talk, wild X allegations, etc.

(46:11) THREE TWiST 500 are readying IPOs… Catching up with Ledger, 1Password, and Mercury

(53:42) Why Jason and Alex think you need multiple banks

(57:40) Why presentation maker Gamma is growing even faster than we thought!

(1:00:37) Checking in with Jason and Alex’s Polymarket IPO bet…

(1:03:44) Could startups become so richly valued that they become “uninvestable” without an IPO?

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.twist500.com

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Follow Lon:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(9:22) Quo - Streamline and scale your customer communications with OpenPhone. Get started free, plus get 20% off your first 6 months, at http://quo.com/TWiST

(19:24) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist

(29:44) Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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

Register for Founder University Japan’s Kickoff: https://luma.com/cm0x90mk

Today’s show:

*The key to avoiding long airport delays? Low-altitude sea planes! Why didn’t you think of that?

We’ve got an awesome line-up of TWiST 500 founders giving us an inside glimpse inside their startups on this Friday special edition.

FIRST: Billy Thalheimer of REGENT introduces us to their aircraft/boat hybrid The Seaglider, and walk us through how it all works, AND why they’re operating in BOTH the commercial and defense sectors from their Rhode Island HQ.

THEN, we’ve got Convexia co-founder Ayaan Parekh showcasing how they’re using a collective of specialist AI agents to exploit other pharma labs’ leftovers and turn them into new drugs and treatments for rare diseases.

FINALLY, Hunter Leath of Archil joins the show to tell us why efficient utilization of cloud data remains a surprisingly complex, and unsolved problem. His solution? Caching-as-a-Service! Find out how it all works, and why pre-caching is SO difficult to do, in this TWiST exclusive chat.

Timestamps:

 • (03:01) Billy Thalheimer of REGENT introduces us to the Seaglider
 • (05:06) Inside the EV aircraft/boat hybrid’s three modes of operation
 • (08:22) How REGENT uses low altitude flight to avoid airport-related hassles

(9:42) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to ⁠http://sentry.io/twist⁠ and use code TWIST
 • (13:57) The converging tech that makes Seaglider possible
 • (18:20) How REGENT is operating in BOTH the commercial and defense sectors
 • (19:39) LinkedIn Ads - Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to 
⁠http://linkedin.com/thisweekinstartups⁠ • to claim your credit.
 • (25:05) Why Rhode Island?!
 • (29:23) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at 
⁠https://pipedrive.com/twist⁠ • (31:04) Convexia co-founder Ayan Parekh joins Alex to discuss “the world’s first AI-maximalist pharmaceutical company”
 • (33:02) Using AI agents to revisit leftover bio IP and unused data
 • (33:22) Why so many drugs fail to reach market
 • (35:46) Applying different agents to different kinds of tasks
 • (44:26) The unique opportunities posed by rare diseases
 • (46:58) On the road toward vertical integration
 • (50:48) Hunter Leath of Archil tells us why utilizing cloud data effectively remains a complex, unsolved problem
 • (51:56) What is “Caching as a Service”?
 • (55:53) Why pre-caching is NOT obvious and “tremendously difficult to do”
 • (57:00) Why the major cloud players didn’t built this themselves
 • (01:00:37) Deliberately keeping the focus narrow… for now…

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.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/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

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.

Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at https://pipedrive.com/twist

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

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Substack: https://twistartups.substack.com

It’s a boat, it’s a plane, it’s REGENT’s Seafarer | E2205

FOLLOW Zach: https://twitter.com/zachcoelius

FOLLOW Jason: https://linktr.ee/calacanis

Ask an Angel with Zach Coelius: is moving to SF still worth it, bubble/recession potential, post-COVID funding & more | E1172

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