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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

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

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:

(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

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:

(9:22) 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

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

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

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

Substack: https://twistartups.substack.com

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

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

Today’s show:

*On TWiST, Jason welcomes an all-star VC panel — Deedy Das of Menlo Partners and Jay Eum of GFT Ventures — for a deep dive into the shocking scale of early-stage AI raises, a transitional moment for investors, the growing importance of the “prosumer” market, ChatGPT’s insane smile curves, and much much more.

IN THIS EPISODE

 • What the panelists make of Roelof Botha’s exit from Sequoia… and is he really going anywhere…
 • Why Jason says VC is no longer the best way to get rich…
 • Why so many private companies are growing SO HUGE before going public…

And much more!

Timestamps:

(00:03:37) Jason is fresh from surviving Riyadh traffic but he’s here and introducing our all star panel

(00:04:03) Why Jason compares Riyadh to Silicon Valley in the 1960s

(00:05:21) Friend of the Pod Roelof Botha is stepping down at Sequoia… our insiders try to guess what might have happened…

(10:00) Crusoe - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.

(00:13:11) Deedy moved up at Menlo without being a venture native… he shares the secrets behind his rise.

(00:19:09) Was Roelof wrong about “return-free risk”? Does more capital always = more great companies?

(20:00) 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!

(00:26:54) With so many private companies growing SO HUGE… when is the right time to go public? Considering the case of Glean and Stripe…

(30:00) AWS Marketplace - If you’re ready to really accelerate your sales cycle, AWS Marketplace is your next stop. Head to https://aws.com/startups to learn more.

(00:30:07) Why Jason says venture capital is no longer the best way to get rich

(00:32:34) Why AI apps are so appealing to enterprises after years of paying for SaaS

(00:36:32) The growing importance of “prosumers”

(00:37:31) Why Deedy says a smile curve is the most beautiful depiction of “Product Market Fit”

(00:44:36) Why it’s still tough to raise pre-seed money, even during an AI “boom”!

(00:46:08) Why Jason says the hardest job in the tech ecosystem is being an investor

(00:55:52) “Time is one of the primary drivers of venture capital return.” - Jay Eun

(00:57:42) Deedy on the shocking amounts being raised by early-stage AI companies

(01:00:21) Just how much DO VCs work compared to founders? The panel compares notes.

(01:02:53) Are some investors not doing diligence? Deedy on the speed of some AI deals.

(01:16:51) The panel picks their fav portfolio company of the moment (or one of their faves)

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Thank you to our partners:

Crusoe - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.

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Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

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

Today’s show:

*Starcloud has started sending AI chips into orbit. So is this where the datacenters the power AI will one day live? And does wifi work in the vacuum of space? We’re asking the TOUGH questions.

PLUS Jason and Alex are doing a deep dive on all this week’s OpenAI news. Will they ever be able to pay back all these GPU purchases? What happens to the wider economy on the off chance they don’t thrive? And what’s with these rumors that ChatGPT has stopped giving medical or legal advice?

All that and a look at TrustMRR (and why Jason advises you not to publicly share your Stripe), why Jason thinks Netflix should buy CNN, our hosts favorite Nazi hunter movies, and MORE.

Timestamps:

(0:00) Would you trust an LLM with your health?

(2:08) Jason is bringing Founder U to The Kingdom AND Japan, so he’s streaming in today live from Riyadh

(4:20) Jason’s guide to mastering international travel. (Shoutout to Whoop)

(5:05) Are the big AI companies going TOO HARD on GPUs? And does this matter?

(11:30) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(14:53) What happens to the wider economy if ChatGPT FAILS? Who gets hit by the “contagion”?

(18:22) Jason’s more likely scenario: What if ChatGPT becomes just one player in a larger market?

(21:22) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

(23:57) ChatGPT can still give you general health and legal advice… just not a full diagnosis

(31:57) 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.

(33:09) TrustMRR and startups sharing their Stripe data… Why Jason says total transparency might be too much

(38:35) We’re really sending datacenters to space! Starcloud made it happen.

(41:02) Does wifi work in space? A TWiST investigation…

(47:01) Checking in with Polymarkets on the NYC mayoral election and the government shutdown

(53:09) Legal AI startup Legora (from Sweden) is now a unicorn… why this niche is growing so fast

(58:14) Netflix wants to buy WBD… Here’s why our hosts think they should keep CNN.

(1:07:58) BUT WE DIGRESS: Lon and Jason’s favorite Nazi hunter movies

(1:10:25) Founder Q’s! The best way to track runway and burn rate for early stage companies.

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

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

Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

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.

Sending datacenters into orbit | E2203

What will be OpenAI’s IPO price? Place ya bets! | EXXX

*Polymarket’s sharps are already placing bets on when ChatGPT maker OpenAI will go public… and Jason and Alex want in on this action. They’re placing side wagers on how the House that Sam Altman built will be valued once it finally goes public.

PLUS find out why Amazon is Jason’s stock pick for the next five years… Why startups are starting to release their own foundation models, and what this means for major players like OpenAI and Anthropic… AND Producer Oliver stops by with an in-depth look at the music-generating Suno app.

Friday shows don’t get any bigger than this.

Register for Founder University's Japan Kickoff!

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Today’s show:

*Timestamps:

(0:00): Jason doesn't trust Sam Altman... Stay tuned!

(2:24) Jason’s been using Tesla FSD’s “Mad Max” Mode and it’s a SPICY ride!

(8:54) Jason and Alex checked out Higgsfield’s new Face Swap tool… Jason thinks this will revolutionize the movie casting process

(10:39) 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.

(14:03) Here’s what Jason thinks: there are acceptable uses of Higgsfield’s tech but some are OVER THE LINE

(17:23) Here’s why Jason says the music industry deals with startups like the Mafia

(19:59) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!

(21:02) Producer Oliver has been playing around with AI music app Suno… here’s a live demo

(22:47) We’re using Suno to make a Dire Straits song about JCal!

(30:11) PaperOS - Whether you’re raising a round, launching a fund, or managing a venture portfolio, PaperOS can unlock simplicity and scale across your empire of capital, contracts, and companies. Claim your $10,000 credit at https://paperos.com/twist

(39:42) IT’S EARNINGS WEEK! What Jason and Alex make of the fresh numbers from Amazon, MSFT, and Alphabet

(40:58) Jason’s checking out his Grokipedia page… could this be the internet’s new go-to resource?

(45:15) Why Amazon is Jason’s pick of THE stock for the next 5 years

(46:42) Three startups made their own AI models! Is the era of paying big co’s for their LLMs coming to an end?

(50:09) Jason’s warning for anyone “dumb enough” to use OpenAI’s API… they are studying you!

(57:16) It’s a new Jason-Alex bet… What will OpenAI’s IPO price be?

(59:35) What happened with Navan’s IPO? Jason and Alex dig into the numbers.

(1:07:37) Why Jason compares some later investors to Wormtongue from “Lord of the Rings”

What will be OpenAI’s IPO price? Place ya bets! | E2202

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Budgets, models & what investors are looking for with Scott Orn | Kruze Consulting Startup Finance Basics

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