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.
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*There are $100 trillion in global assets sitting on top of what Hanover Park co-founder/CEO Chris Hladczuk calls "human duct tape": armies of accountants in offices patching together work from various legacy tools (QuickBooks, Excel) that are holding funds' own data hostage. Can all of this be replaced with AI? Find out how their startup went from overseeing $1B to $20B in assets in just 15 months.
PLUS, we flash back to March 2020, when Jason and Figma co-founder/CEO Dylan Field broke down the design tool's initial go-to-market strategy, made some WILDLY inaccurate COVID predictions, and considered anxiety about "SaaS burnout" years before the category went full apocalyptic.
10:48 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://northwestregisteredagent.com/twist
13:51 Context vs. intelligence gaps
16:11 No PMs, No Designers
20:46 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
23:18 This is a $100T opportunity
25:36 Flashback w/ Dylan Field of Figma
29:15 Sentry - Your team should be focused on shipping features — not chasing down bugs. New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST
Forget the triple-triple-double-double-double; the new bar for startups hoping to raise venture capital has reached the stratosphere, though our venture panel is worried that startups are focusing too much on today's problems that may not become companies tomorrow. During a lively VC roundtable, Cowboy's Aileen Lee, Floodgate's Mike Maples, and Lerer Hippeau's Ben Lerer joined Alex to dig into exiting pre-AI startups, rising valuations, token spend, why they are keeping their funds small, and whether the government just tripped OpenAI and Anthropic!
*Schools teach kids to memorize formulas. AI helps them skip thinking entirely. Brilliant founder Sue Khim joins TWiST to tell us how her new AI tutor, Koji, uses the Socratic Method to help students solve complex problems on their own. Find out why she says "People aren't anti-AI. They're anti-being replaced and anti-slop."
PLUS Jason's take on the VC horror stories going around X… and his own anecdote about the tenacity and passion of legendary investor John Doerr.
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 to reserve your capacity for the latest GPUs today.
Why data is the biggest AI bottleneck (feat. Arthur Mensch of Mistral AI) | E2212
Épisode 2212
jeudi 20 novembre 2025 • Durée 01:05:14
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?
*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.
Archer buys an airport, Ramp's huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210
Épisode 2210
mardi 18 novembre 2025 • Durée 01:14:16
*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!)
(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
Stop ghosting your friends with Nox's RPLY, plus Alloy Automation and a Shopify flashback | E2209
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!
Why We Need Ferries and Tugboats in Space w/ Orbital Operations | E2208
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
Inside Harvey AI's $8 billion AI lawyer app, PLUS How OpenRouter unites the LLMs | E2207
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 to book a demo and see it in action.x and build next. Head to to book a demo and see it in action.
0:00 Aileen Lee, Mike Maples, and Ben Lerer join the show
5:13 Venture liquidity returns: what SpaceX/Stripe distributions mean for LPs
9:13 Bending Spoons prices IPO at $29/share, roughly $18.4B valuation
10:31 Agree.com - Stop chasing invoices and automate your entire contract-to-cash stack. Go to https://agree.com and tell them Jason sent you to get 50% off for life!
12:09 "Companies get bought, not sold" — Ben on taking first offers seriously
17:41 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!
19:34 Mutiny's burn-the-boats AI pivot with Jaleh Rezaei
20:19 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/twist
22:15 Mike's KeepSafe story: the "rule of 70" and profit-first companies
25:12 The new growth bar: 5x, 4x replaces triple-triple-double-double
28:55 Fund size is your strategy: why Floodgate and Lerer Hippeau stay small
30:11 CLA - Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at https://www.claconnect.com/withyou
37:39 The $100M Series A: Starcloud, General Intuition, Scale Cognition, Scout AI
40:35 King-making rounds and why mega-seeds destroy optionality
54:11 Open-weight models: the GLM-5.2 moment and going model-agnostic
55:30 Why fine-tuning open models is a treadmill, with Cursor/Kimi as an example
1:03:28 Grading the Trump administration on Mythos and Fable
1:06:33 Rising anti-AI sentiment, the wealth gap, and lessons from social media
1:11:43 Raising kids in the post-intelligence era
1:12:35 Where to find the panel and what each firm is investing in
1:41 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!
4:10 Brilliant: from launch to product market pull
10:46 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://northwestregisteredagent.com/twist
15:08 Pricing against tutors, not apps
19:25 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist
21:22 Koji demo
24:11 Keeping Brilliant local while expanding
30:22 Shopify - Turn those What Ifs into sales with the e-commerce platform powering millions of businesses. Sign up for your $1-per-month trial today at https://shopify.com/twist
40:10 Every founder has a VC horror story
44:33 John Doerr went the extra mile to hear JCal's pitch
(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
(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!
(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?
(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!
(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.
(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.
(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
(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.
(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
(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"
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.
(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
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