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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 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

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:

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

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

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?

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:

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

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

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

Today’s show:

*Working from 9 am to 9 pm, 6 days a week, might seem like TOO INTENSE a commitment for some, but Jason argues that elite performance — and the mega-compensation that goes along with it — sometimes requires personal sacrifice. While 72-hour weeks might lead to burnout for some, it really comes down to individual choice.

PLUS Jason and Alex deep dive the NBA gambling scandal and the sketchy reality behind high-stakes home games of poker. PLUS Presh Kumar takes us behind the scenes, to see how AI apps helped him develop and workshop the video for his new wellness startup, Tempo, and what’s with Anthropic buying chips from their AI rivals, Google? It’s a can’t miss This Week in Startups.

Timestamps:

(00:06:49) Jason and Alex are poker fans… what do they think about this insane NBA gambling scandal?

(10:00) LinkedIn Ads - Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://LinkedIn.com/ThisWeekinStartups to claim your credit.

(20:00) Nexos.ai - Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at https://nexos.ai/twist.

(00:25:09) Is working “9-9-6” a reasonable goal? A guarantee of success? Why Jason compares it to being an Olympian.

(30:00) Every.io - Running a startup is hard enough. Every takes care of incorporation, banking, payroll, benefits, accounting, taxes and more so that you focus on building, not back-office admin. Visit every.io.

(00:38:00) Our old buddy Presh walks us through the process of making his Tempo launch video

(00:42:28) Jason and Alex check out some of Ridley Scott’s famous storyboards

(00:48:03) Anthropic is buying TPUs from Google… Are these companies in LIKE with each other?

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

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

Nexos.ai - Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at https://nexos.ai/twist.

**Every.io -** Running a startup is hard enough. Every takes care of incorporation, banking, payroll, benefits, accounting, taxes and more so that you focus on building, not back-office admin. Visit every.io.

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

If you’re not working 9-9-6, are you working hard enough? | E2198

Today’s show:

*Amazon’s dropping a LOT of employees for AI and robots… are Jason’s darkest predictions coming true?

Legendary investor Elad Gil joins Jason and Alex for the full show today! Together, they’re digging into the Amazon news, looking back at Jason’s predictions from just last month, and theorizing about just how many people will lose their jobs to computers, and what we’re going to do about it. (Is it possible the US hasn’t been massively hit by job displacement so far because those gigs already moved overseas?)

PLUS… Anthropic’s Dario Amodei responds to criticisms from JCal’s bestie David Sacks, Sesame emerges from stealth to work on AI wearables, and where will people in the future interact with their favorite apps? A headset? Phones? Somewhere else? The great debate continues.

Timestamps:

(00:04:04) Our guest is iconic angel investor Elad Gil! What’s he working on…

(00:04:54) Alexandria AI translates public domain books into all commonly spoken languages… Do people actually prefer AI translations?

(00:09:16) Why compute tends to centralize over time… (It’s because of economies of scale!)

(00:09:29) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(00:12:49) So are we building TOO MANY datacenters? Will AI apps eventually run on your phone anyway?

(00:16:39) Jason says “The Age of Efficiency is upon us.”

(00:19:24) When companies trade inference for market share

(00:19:27) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(00:21:57) Why one of the main challenges of adopting AI is buy-in and convincing teams to use it.

(00:25:47) Elad’s robotics questions: (1) What % of winners will be incumbents?

(00:27:50) Jason called the Amazon news last month and we have the receipts!

(00:29:36) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first yea

(00:45:33) Jason says Adobe and Figma should abandon the UK entirely.

(00:45:55) Time for a Polymarket: The sharps say 80% chance Tesla beats their quarterly earnings

(00:51:02) What is Sesame? They just emerged from stealth, they raised $250M, and they’re working on AI wearables.

(00:53:21) Jason has concerns about AI wearables that are always recording… Does Elad share these concerns?

(01:03:17) The crypto industry is now one of the largest purchasers of US government debt… what does that mean? Who owns who?

(01:08:53) Anthropic responded to JCal’s Bestie David Sacks… Is Dario Amodei a doomer? Fearmongering?

(01:19:12) Why Jason thinks AI companies need to self-regulate

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Amazon’s “Age of Efficiency,” LLM distribution, AI wearable worries, and more with Elad Gil | E2197

Are AI tools in the classroom just time-savers, or can they have genuine educational value?In a must-watch TWiST 500 interview, Alex chats with Magic School founder (and former principal) Adeel Khan about how AI tools can make teachers more effective, and keep students inspired, without just doing all the work for them. He talks about turning an AI chatbot into a true assistant teacher, that keeps the lessons balanced yet challenging, and particularly empowers classroom novices and non-professionals.THEN… is 6 years too long for employees to wait to vest? Is this just another founder trying to reinvent EVERYTHING, just because they can’t resist? Ramp CEO Eric Glyman joins Jason and Alex to answer pressing founder questions from viewersPLUS there’s a new entrant in our Gamma Pitch Deck competition, and it’s so compelling, Jason can’t wait to invest! Kris Canete of On the Fly Energy tells us about America’s fragile power grid and his elegant solution: flywheel energy storage!Timestamps:0:00 - Welcome to TWiST!02:59 - Former principal Adeel Khan of TWiST 500's Magic School AI tells us why “teachers are magic”09:41 - Goldbelly ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.10:50 - How AI tools can particularly help out classroom novices and non-pros who are just getting started20:57 - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.26:58 - How Magic School stays ahead of shifting standards across different states and regions32:57 - Zite is the fastest way to build *business software* with AI. Build apps, forms, websites and portals that connect to the tools you already use. Go to *zite.com/twist* to get started.33:30 - Why the best feedback Adeel ever got came from a teenager36:30 - Making AI a true assistant teacher, that keeps lessons balanced yet challenging38:38 - Is a 6-year vesting schedule too aggressive? Eric Glyman responds.41:00 - When even ambitious founders should sometimes just accept a standard deal.57:33 - What IS flywheel energy storage?01:00:00 - Why Jason loves the Fly Energy Gamma pitch and wants to invest right now.01:34:13 - Gamma Outro*Subscribe to the TWiST500 newsletter: [https://ticker.thisweekinstartups.com](https://ticker.thisweekinstartups.com/)Check out the TWIST500: [https://www.twist500.com](https://twist500.com)Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: [⁠ / alexwilhelm ]( / alexwilhelm )*Follow Jason:X: / jason LinkedIn: [ / jasoncalacanis ]( / jasoncalacanis )Great TWIST interviews: [Will Guidara,]( • Lessons in Unreasonable Hospitality with W... ) [Eoghan McCabe]( • Great Builders & Success First with Interc... ), [Steve Huffman](https://podcasts.apple.com/us/podcast..., [Brian Chesky](https://podcasts.apple.com/ca/podcast..., [Bob Moesta,]( • Decoding Customer Insights, Trust, and the... ) [Aaron Levie](https://podcasts.apple.com/ca/podcast..., [Sophia Amoruso](https://podcasts.apple.com/ca/podcast..., [Reid Hoffman](https://podcasts.apple.com/ca/podcast..., [Frank Slootman](https://podcasts.apple.com/ca/podcast..., [Billy McFarland](https://podcasts.apple.com/ca/podcast...)*Check out Jason’s suite of newsletters: https://substack.com/@calacanis*Follow TWiST:Twitter: / twistartups YouTube: / thisweekin Instagram: [ / thisweekinstartups ]( / thisweekinstartups )TikTok: / thisweekinstartups Substack: [https://twistartups.substack.com](

Magic School uses AI to help kids learn, not cheat | E2196

Today’s show: *Is the AI bubble going to POP? And if so, how much of our economy is it going to take down with it?On a new TWiST, Jason, Alex, and Lon debate the size and scale of the AI bubble, whether poppage is imminent, and just who we can blame for the last few economic crises. (HINT: Not the tech industry!)PLUS why Jason STILL thinks the current AI cycle will be the biggest in tech history, how this morning’s AWS mega-failure might impact the company’s earnings, the spread of AI fakes in the wake of this weekend’s No Kings march, why LLMs may soon put your broker out of business, and much much more.**Timestamps:** (00:02:26) Is AI a BUBBLE? And if so, how BIG?(00:05:12) Are all the major bubbles and corrections always Wall Street’s fault?(00:08:39) Why Jason thinks this AI will be the biggest cycle in the history of technology(10:00) LinkedIn Ads: Thanks to our partner @LinkedInMktg. Launch your first campaign and get $250 FREE when you spend at least $250. Go to [http://LinkedIn.com/ThisWeekinStartups](https://www.linkedin.com/thisweekinstartups) to claim your credit.(20:00) Thank you to our partner @trustvanta! TWiST listeners automate your SOC2 and get $1,000 off at http://www.vanta.com/twist(00:23:01) Will this morning’s AWS failure impact Amazon’s earnings?(30:00) Thanks to our partner @Openphone! Streamline and scale your customer communications with Quo. Get started free, plus get 20% off your first 6 months, at [http://quo.com/TWiST](http://quo.com/TWiSThttp://quo.com/perks/twist)(00:32:49) People couldn’t spot AI fakes from this weekend’s protests… are we cooked?(00:49:54) Jeremy Strong shows off his Mark Zuckerberg impression… and Jason is impressed

*Thank you to our partners:LinkedIn Ads: Thanks to our partner @LinkedInMktg. Launch your first campaign and get $250 FREE when you spend at least $250. Go to [http://LinkedIn.com/ThisWeekinStartups](https://www.linkedin.com/thisweekinstartups) to claim your credit. 

@trustvanta! TWiST listeners automate your SOC2 and get $1,000 off at http://www.vanta.com/twist

@Openphone! Streamline and scale your customer communications with Quo. Get started free, plus get 20% off your first 6 months, at [http://quo.com/TWiST](http://quo.com/TWiSThttp://quo.com/perks/twist)*Check out Jason’s suite of newsletters: https://substack.com/@calacanis*Follow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: [https://www.instagram.com/thisweekinstartups](https://www.instagram.com/thisweekinstartups/)TikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: [https://twistartups.substack.com](https://twistartups.substack.com/)*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916All rights for the video shared and linked below belong to the original copyright holder, and we are using the footage under the principle of fair use.Listen here:Apple: https://podcasts.apple.com/us/podcast/this-week-in-startups-audio/id315114957Spotify: https://open.spotify.com/show/6ULQ0ewYf5zmsDgBchlkr9Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audioMore from us:Twitter: https://twitter.com/twistartupsInstagram: https://www.instagram.com/thisweekinstartupsOfficial site: https://thisweekinstartups.comSubscribe to our YouTube to watch all full episodes:https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A?sub_confirmation=1Subscribe to TWiST Clips for all the best moments:https://www.youtube.com/channel/UCS7tJlcUA6PzVHEMo-X7ddg?sub_confirmation=1#startups #entrepreneurship #investing #angelinvesting #tech #news #business

Just how frothy is the AI Bubble anyway? | E2195

0:52 Jason intros Greylock's Sarah Guo

3:37 How did Sarah wind up at Greylock?

5:45 Sarah explains Greylock's "Zero to One" thesis & typical term commitment of a VC

11:53 How does Sarah measure her personal performance and her portfolio's performance? What are her biggest strengths as an investor?

16:12 How does she sharpen her decision-making skills?

17:53 Ranking her investment criteria: People, Markets & Product

20:26 Balancing intensity & life outside of work, the commitment of early-stage startups

27:26 Work-life balance & how the venture landscape changed over time

35:36 Greylock's structured & what was Sarah's first investment & how did it play into her investment thesis?

43:38 Sarah's investments in work-enabling software

48:00 Sarah recommends Dylan Field of Figma join the show - episode dropping Friday!

49:22 Identifying subtle flashes of brilliance in early products

58:28 Female founders being held to a higher standard

1:02:35 Anti-portfolio: Zoom

1:10:06 Sarah turns off her virtual background and reveals her location

E39: “Angel” Podcast: Sarah Guo, General Partner at Greylock Partners shares insights on Greylock’s “Zero to One” investment thesis, sharpening her decision-making skills, ranking team, market & product as investment criteria & the changing landscape of VC

E39: “Angel” Podcast: Sarah Guo, General Partner at Greylock Partners shares insights on Greylock’s “Zero to One” investment thesis, sharpening her decision-making skills, ranking team, market & product as investment criteria & the changing landscape of VC

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