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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 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)

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

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

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:

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.

Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit

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.

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

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.

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:

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!

https://luma.com/cm0x90mk

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

Today’s show:

*Why rebrand an app with 40 million daily active users?

On TWiST, Grammarly CEO Shishir Mehrotra swings by to explain why he’s renaming his company after the mail app he just purchased, Superhuman.

Plus he’s giving us a first look at the startup’s new AI assistant, Superhuman Go, digging into their new agent-centered strategy, looking ahead at the potential for AI job displacement, and more.

Jason and Alex also talk about our new nuclear deal with Westinghouse and Japan, OpenAI’s conversion and what it means for Microsoft, 1x’s tele-operated Neo-bot for chores, and much more!

Timestamps:

(00:07:56) Jason is headed to Tokyo, and NOT just for skiing this time!

(10:00) Uber AI Solutions**:** Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist

(00:12:21) Untangling this US government-Japan-Westinghouse deal for nuclear power… and why nuclear power is SO important

(20:00)DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twist

(00:20:04) Why Jason says sabbaticals and 4 day work weeks are for established brands, not startups

(30:00) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.

(00:33:01) Will income inequality become a concern, even for the wealthy? Jason says YES.

(00:37:29) Shishir Mehrotra from Gram— NO WAIT, Superhuman! joins us to talk name changes

(00:38:16) Using Grammarly as a model for the new AI assistant, Superhuman Go.

(01:08:39) Nvidia shot past $5 TRILLION in value… How is no one freaked out about this?!

(01:14:52) OpenAI executed their conversion… but Jason says “public benefit corporation” status is pretty meaningless

(01:25:02) Checking out the Neo robot from 1x… he wants to help you with chores and he’s for sale!

(01:32:09) Uber’s speeding up its self-driving plans

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Thank you to our partners:

Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.

DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twist

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

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

Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201

Today’s show:

Jason’s been skeptical on Apple lately, but he’s BLOWN AWAY by his new iPhone Air.Hear why JCal thinks Cupertino’s latest release is “completely inspiring,” and why he’s sure it’s the next step on the road to Apple Glasses.

We’re chatting with LAUNCH founder Zach Handshoe of spacial video startup SpatialGen about designing products for Cupertino AND the intense pressure of performing a Steve Jobs-level keynote.

PLUS Raiza Martin of Huxe stops by to tell us why they’re using audio to make AI assistants more personalized AND proactive, and how they’re already getting noticed in an increasingly crowded App Store.

AND we’ve got another Gamma Pitch Competition entrant! Chess Grandmaster Vasif Durarbayli presents his expert-focused app, ChessEver.

Timestamps:

(2:05) Friend of the pod @ZacharyHandshoe stops by to talk about supporting Apple Immersive Video (and staying up during the AWS outage)

(9:37) Enterpret - Turn feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.

(15:55) The iPhone Air can already shoot spatial video! Just part of why Jason calls it a “completely inspiring” product.

(21:25) Crusoe Cloud - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.

(24:30) Jason offers viewers a peek inside LAUNCH’s Whisper Network

(32:09) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(33:10) Huxe co-founder (and NotebookLM vet) Raiza Martin wants to make your AI assistant more personalized and proactive.

(37:14) Why Raiza and her team went with an audio-forward interface instead of a chatbot.

(43:25) How Huxe is getting noticed in the App Store as a brand new arrival.

(50:25) The big LLMs still aren’t great at writing engaging content for humans, so Huxe is doing it themselves.

(52:41) Chess Grandmaster Vasif Durarbayli from ChessEver joins us for his Gamma pitch!

(54:26) Why Vasif is focusing on very serious players FIRST before appealing to more casual chess fans

(1:05:28) Jason thinks ChessEver is at the moment of “triangulation” in their journey to finding Product Market Fit… what do Grandmasters really want?

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Follow Lon:

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X: https://x.com/alex

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

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X: https://twitter.com/Jason

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

Thank you to our partners:

Enterpret - Turn feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.

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

Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/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

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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

iPhone Air is “inspiring,” and a first step toward Apple Glasses (w/ Zach Handshoe of SpatialGen) | E2200

Today’s show:

Australia has accused Microsoft of employing a dark pattern… Hear why Jason says these kinds of sneaky tactics aren’t usually worth it.

It’s a brand-new Monday TWiST and it’s PACKED with news. In addition to Australia’s allegations against MSFT, we’re looking at Chinese drone fails and wondering how live experiences will change in the age of AI.

PLUS has Tesla finally “solved” FSD after years of promises? Does it matter that so much of Mercor’s revenue goes back out to contractors? Do Chinese LLMs have a major advantage when it comes to the stock market over Western counterparts? Why Jason avoids overseas deals when he doesn’t speak the language or know the culture. And much more!

Timestamps:

(00:03:44) Fall is here! And Jason is already looking ahead to “BFCM” and the holiday season.

(00:07:13) We’re bringing back the TWiSTies and a Prediction 2026 show

(00:07:33) People are using AI to create fake receipts for fraudulent invoices!

(10:00) Pipedrive - Bring clarity and control to your sales process with Pipedrive, the #1 CRM for small and medium sized businesses. Supercharge your sales today. Start with a 30-day free trial at pipedrive.com/twist.

(00:14:23) It’s earnings week for Meta AND Alphabet AND Microsoft AND AMAZON!

(00:19:55) What happened with the disastrous Chinese drone and fireworks show?

(20:00) Monarch - Thanks to our partner, Monarch! Try the app and get 50% off your first year by visiting monarchmoney.com/twist.

(00:27:37) Why Jason thinks live experiences are going to get much bigger and more impressive in the age of AI

(00:29:34) Why Tesla is training FSD on synthetic data now… Has FSD finally been “solved”?

(30:00) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits

(00:45:10) What’s going on with these new Sequoia funds? Jason unpacks the strategy…

(00:50:50) Jason doesn’t like to invest overseas unless he speaks the language and knows the culture

(00:51:11) Jason’s thoughts on the controversy surrounding Sequoia partner Shaun Maguire’s comments

(00:58:34) Mercor pays out 60-70% of its toppling revenue to contractors… does this MATTER?

(01:06:14) Do Chinese LLMs have a major advantage when it comes to investing? (Humans are now betting on all this on PolyMarket)

(01:09:45) Australia alleges that Microsoft is employing a dark pattern… why Jason says that’s a problem.

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

AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits

Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST

Pipedrive - Bring clarity and control to your sales process with Pipedrive, the #1 CRM for small and medium sized businesses. Supercharge your sales today. Start with a 30-day free trial at pipedrive.com/twist.

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

Jason Unpacks Sequoia’s New Funds | E2199

Check out Founders Fund: https://foundersfund.com

FOLLOW Keith: https://twitter.com/rabois

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

Keith Rabois on Miami vs. Bay Area, cognitive variety, America’s self-examination & more PLUS Keith’s Best Twitter Dunks | E1182

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