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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

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

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

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

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

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

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

Deel’s growth overshadows SpyGate, Claude learned new skills, and the great “momentum is moat” debate | EXXX

Today’s show:

*Deel’s growing fast enough that investors are overlooking the espionage allegations and jumping on board anyway. (LAUNCH now owns a lil taste of Deel, so Jason is on board!)

PLUS is the Mag 7 about to become the Mag 70… Why legendary investor Roelof Botha thinks VC is not an asset class… How startups can use capital as a weapon… AND Anthropic gave Claude more skills, which they hope will help pay their bills.

Timestamps:

(00:01:34) Jason’s excited for ski season and checking his favorite powder app, OpenSnow

(00:04:02) Why Jason’s done with meetings; he’s pulling a Doug Leone!

(00:06:27) Jason can tell the market’s heating up because people are starting to lose their minds.

(00:09:31) How much will global AI tools one day be worth? Alex is crunching the numbers.

(10:00) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(00:15:22) PREDICTION: The Mag7 is about to become the Mag70

(20:00) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist

(00:25:36) Deel’s big raise… Why major growth overshadows spying allegations

(30:00) 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.

(00:33:31) Why Roelof Botha says VC is a “return-free risk,” and not an “asset class.”

(00:40:49) The two reasons why VC firms end

(00:44:18) How startups can use capital as a weapon

(00:57:52) Anthropic gave Claude Skills to pay the bills

(01:00:51) Jason’s vision for what Grammarly could become

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:

Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at 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.

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

Deel’s growth overshadows SpyGate, Claude learned new skills, and the great “momentum is moat” debate | E2194

Today’s show:

*On a very special TWiST, Jason’s joined by “one of the greatest investors in in the history of VC,” Steve Jurvetson of Future Ventures.

Together, they look back at some of Steve’s earliest investments and learnings, the promise and ultimate failure of nanotech, breaking down the AI hype cycle, the primacy of neural networks, the return of nuclear power, why “AI safety” might be illusory, and much more.

It’s a packed show full of deep insights from one of the greatest minds in technology today. Do not miss this ep!

Timestamps:

(00:00)Jason’s 1-on-1 today with “one of the greatest investors in the history of VC,” Steve Jurvetson

(00:03:04) The early origins of Steve’s fascination with “deep tech”

(00:08:03) Jason and Steve recall playing around with the TRS-80 (“The Trash-80”)

(10:00) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.

(00:15:13) Keeping your portfolio diverse when so many companies look the same

(20:00) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

(00:20:49) The promise of nanotech and why it fell apart

(00:25:46) Breaking down the “hype” cycle and how trends get co-opted

(00:26:27) Why Moore’s Law and the Power Law are so important for investors

(30:00) 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!

(00:33:36) Understanding the rise of GPUs and how they resemble tiny brains

(00:51:32) Revisiting a classic clip of Steve talking about robots

(00:54:04) How Jason and Steve got their hands on some of the earliest Tesla Roadsters

(01:00:09) Flashback Clip: Elon predicts 2025 in 2015… how’d he do?

(01:02:46) Why did the world turn SO strongly against nuclear energy?

(01:16:06) Can we make AI “safe” in the age of GPT Psychosis? Is it too inscrutable?

(01:21:54) Why Steve thinks technology will ultimately doom autocratic regimes.

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:

 • TECH: Say it without saying it. Head to 
get.tech/twist • or your favorite registrar to get a clean, sharp .tech domain 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 
https://www.northwestregisteredagent.com/twist • today!
 • Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to 
getperspective.ai/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

Legendary VC Steve Jurvetson looks ahead at neutral networks, Tesla, nuclear power, and more | E2193

Today’s show:

*Eric Glyman of Ramp joins us to share the fintech unicorn’s growth secrets AND their Lab full of research data.

On TWiST, Jason and Alex chat with Eric about Ramp’s counter-intuitive mission — helping startups spend LESS money — PLUS they take a deep dive into the company’s treasure trove of startup trend data. Why is there a huge spike in unemployed recent college trends? Is “static team size” as a big a story as Jason and Alex think? What does it actually take to get companies to adopt AI Agents? The answers all might be in these Ramp numbers.

PLUS Eric joins us for some hot Founder Q’s, and what’s going on with all this Y Combinator drama? We’re sifting through the angriest tweets for the inside scoop.

FINALLY, Jason recommends some of his favorite startup accelerators of the moment (aside from his own) including…

PearXArc from SequoiaAntlerSpeedrun from a16z
Timestamps:

(00:02:18) The 72-hour rule strikes again: Trump’s China’s tariff reversal

(00:03:10) Why crypto got hit even HARDER than the stock market post-Trump announcement

(00:07:32) Market manipulation “at a scale we’ve never seen before…”; what does this mean for everyday investors?

(10:05) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(00:12:55) Ramp CEO Eric Glyman swings by to update us on his fintech unicorn’s growth and their “Lab” for research data

(20:09) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(00:21:40) Is “static team size” a real trend? What the Ramp data shows…

(00:26:25) Ramp’s “counter-intuitive” mission: to help companies spend LESS money, not more.

(30:24) Paper OS offers the largest library of AI-driven Workflows for both founders & fund managers. Claim your $10K credit at paperos.com/twist

(00:38:07) WHY the huge spike in unemployed recent college grads? Especially among the guys?

(00:49:16) What it actually takes to get companies to adopt AI agents into their processes

(00:52:25) Why Jason thinks Eric is a top-tier TWiST guest. We’re going through the metrics…

(00:54:05) There’s YC drama on social media now… we’re spilling the tea.

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 • Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at 
https://www.netsuite.com/twist • PAPER OS - Building an empire? PaperOS offers the largest library of AI-driven Workflows for both founders & fund managers. Whether you’re raising capital, launching a fund, or wading through diligence, PaperOS unlocks simplicity and scale for your ever-growing empire. Claim your $10K credit at 
paperos.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

What Ramp’s data tells us about AI, unemployment and more with CEO Eric Glyman | E2192

Today’s show:Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason to break down what’s happening in today’s startup market. From excess dry powder on the VC side to companies struggling to “grow into” their valuations, Becki shares what founders need to know about deal terms, pay-to-play provisions, and the shift from the 2021 heyday to today’s more structured environment.

 • Why down rounds and structured deals are becoming more common
 • How “pay-to-play” works (and why it’s showing up so often now)
 • The psychology of VCs vs. founders during tough fundraises
 • What the M&A landscape really looks like in 2025
 • Legal provisions investors are using to protect themselves in today’s talent wars

Whether you’re a founder preparing for your next round or an investor navigating tougher terms, this conversation will help you understand the new realities of startup fundraising.

*

Timestamps:

(0:00) Becki DeGraw joins Jason for Startup Legal Basics

(1:12) The “perfect storm” shaping today’s startup market

(4:30) Companies struggling to grow into 2021 valuations

(6:31) Why down rounds and structured deals are rising

(8:59) Pay-to-play explained: what happens if investors don’t participate

(15:43) The mid-market M&A wave vs. big tech acquisitions

(20:37) Talent wars, acqui-hires, and protective legal provisions

*

Check Out Wilson Sonsini: https://www.wsgr.com

Check out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics

*

Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/

*

Follow Jason:

X: https://twitter.com/Jason

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

*

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

Market Update and Trends w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

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