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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

This Week In Startups is made possible by:

Vanta - https://www.vanta.com/twist

NetSuite - https://www.netsuite.com/twist

Lemon.io - https://lemon.io/twist

*

Today’s show: 

Domestic robots have never been hotter… so why is iRobot in so much trouble?!

On TWiST, we’re investigating the recent troubles facing the automated vacuum robot, Roomba. We’ve all seen these little discs sweeping up our friends’ floors… but now the company behind them is running out of cash.

What happened to iRobot, and would things have turned out differently if they had been sold to Amazon back in 2022?

PLUS why Jason thinks you should spend your disposable income on investing… Is Alex still a journalist, and what does that actually mean for his portfolio?… Are founders and investors too cautious when it comes to signaling risk?… Why did all those internal Pipe documents leak online?… And MUCH MORE!

Timestamps:

(00:00) Why Jason loves Incentivizing New Ventures and Economic Strength Through Capital Formation!

(09:48) Jason warns “no one is coming to help you with your job loss”; you’re on your own!

(10:21) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(13:05) Why Jason thinks laid-off HR folks should be starting their own “micro-funds"

(14:13) Does Alex consider himself a journalist? Is it unethical for him to invest in companies? (Let’s get INTO IT.)

(16:02) You can’t become complacent when you’re in the lead!

(20:03) Why you should use disposable “entertainment” income on investing

(22:32) Netsuite - Get the free business guide Demystifying AI at https://www.netsuite.com/twist

(23:36) $9B in new funds?! What is Lightspeed up to?

(26:10) Is everyone too cautious about “signaling risk”?

(28:39) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(31:21) How does Jason think those Pipe documents leaked? And WHY?

(38:15) The critical importance of diversification

(39:35) iRobot went BANKRUPT! Who killed the Roomba?

(44:47) Are there ANY potential deals that would bother Jason? It’s all about market share.

(48:18) HuggingFace is moving major Reachy Minis! How open source turns everything upside down.

(53:22) How Polymarket will decide when/if the AI bubble “bursts.”

*

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

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

Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

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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:

(10:21) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(22:32) Netsuite - Get the free business guide Demystifying AI at https://www.netsuite.com/twist

(28:39) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

Great TWIST interviews: 

Will Guidara

https://youtu.be/pvJa2pzuXWQ

Eoghan McCabe

https://youtu.be/9dHN4YFkgv4

Steve Huffman

https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424

Brian Chesky

https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112

Bob Moesta

https://youtu.be/y2UMzSqX94Q

Aaron Levie

https://podcasts.apple.com/ca/podcast/box-ceo-aaron-levie-breaks-down-box-ai-and-generative/id315114957?i=1000612384545

Sophia Amoruso

https://podcasts.apple.com/ca/podcast/sophia-amoruso-on-branding-raising-a-fund-portfolio/id315114957?i=1000601352978

Reid Hoffman

https://podcasts.apple.com/ca/podcast/reid-hoffman-on-ais-crescendo-moment-regulation-and/id315114957?i=1000612548498

Frank Slootman

https://podcasts.apple.com/ca/podcast/snowflake-ceo-frank-slootman-on-moving-the-needle-win/id315114957?i=1000602560622

Is this the end for the Roomba? Why iRobot went bankrupt | E2224

This Week In Startups is made possible by:

LinkedIn Ads - http://linkedin.com/thisweekinstartups

DevStats - https://www.devstats.com/twist

Crusoe - https://crusoe.ai/build

Today’s show: 

FINALLY, you can hang out with Kylo Ren and Olaf the Snowman… thanks to the magic of AI.

On TWiST, we’re digging into the mega OpenAI-Disney deal. Mickey is giving Sam Altman a $1 billion investment AND will allow is copyrighted characters to appear in Sora and ChatGPT images.

Of course, Jason predicted this would happen WAY BACK during the summer months and even showed off his “Darth Calacanis” creation on the “All-In Podcast.”

PLUS Amazon has been launching and pulling AI features from Prime Video… what gives? Jason’s predictions on the coming AI blowback and who’s on what side. Why he’s so focused on Education, Health Care, and Housing as issues. AND why founders should always take calls from Big Companies, even if it might just be a fishing expedition.

It’s a new Friday TWiST! Check it out!

Timestamps:

(00:00) Lon joins Alex and Jason to talk about the big Disney-OpenAI deal bringing Disney characters to Sora

(03:10) Jason totally called the Disney-OpenAI stuff on All-In

(9:42) 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.

(18:59) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.devstats.com/twist.

(20:15) Why Amazon Prime Video pulled its AI recaps and anime dubs

(24:44) Who gets to set the rules around AI: The Debate Continues

(26:13) Jason’s predictions on the AI blowback coming in 2026… with clips!

(30:11) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.

(31:21) Is AI here to help people or replace them?

(35:55) It’s all about EHH: Education, Health Care, Housing

(40:47) How all of this and MORE will be impacted directly by AI automation

(45:35) Why Alex wants to lower the temperature around AI Doomerism

(51:19) JUST FOR FOUNDERS: When should you take a call from a BigCo?

(53:45) Why Jason thinks just about everyone in media will lose to TikTok and YouTube

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

Check out the TWIST500: 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/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:

(9:42) 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.

(18:59) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.devstats.com/twist.

(30:11) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.

Disney and OpenAI sign landmark deal… and we saw it coming! | E2223

This Week In Startups is made possible by:

Uber - http://uber.com/twist

Pilot - https://pilot.com/twist

Northwest Registered Agent - https://www.northwestregisteredagent.com/twist

Today’s show: 

Boom is still making supersonic jets but ALSO plans to start selling their turbines as power sources for AI data centers. It’s a perfect example of problem-solving on the go and how “the best founders… MAKE IT HAPPEN.”

Join us for another insightful VC roundtable episode, featuring special guests Bryan Kim (a16z) and David Clark (Ven Cap).

They’re discussing why Boom’s turbine announcement is about necessity AND opportunity PLUS…

- Why we might NOT be in an AI bubble after all

- Promoting your startup without spending your entire runway on marketing

- Why founders need to be RELENTLESS

- Bill Gurley’s classic response about Uber’s Total Addressable Market

- AND LOTS MORE

Bill Gurley’s iconic “Miss By a Mile” post: https://abovethecrowd.com/2014/07/11/how-to-miss-by-a-mile-an-alternative-look-at-ubers-potential-market-size/

Link to David’s LinkedIn (including the AI Bubble chart): https://www.linkedin.com/feed/update/urn:li:activity:7404139606398443520/

Timestamps:

(02:11) It’s a VC Roundtable with special guests Bryan Kim (a16z) and David Clark (Ven Cap)

(03:07) Why Bryan is leading a Series A into learning app Oboe

(06:20) Calculating a startup’s value to make everyone “somewhat unhappy”

(09:19) How Oboe hits a lot of the same metrics that LAUNCH looks for in startups

(11:58) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at http://uber.com/ai-solutions

(12:57) How funds decide when to cash out and lock in some DPI

(18:12) When some LPs want to sell and others want to buy…

(19:57) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year. 

(24:07) Is the threat of AI job displacement boosting self-improvement apps?

(27:37) Why Jason says we’re all standing on the shoulders of Bill Gurley

(29:46) 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!

(31:28) Boom’s turbine pivot, and why it’s about necessity AND opportunity (in that order)

(34:14) THE BEST FOUNDERS find a way to make it happen!

(39:10) So… are we in an AI bubble? David says NOT NECESSARILY! Checking out the actual metrics.

(44:36) We’re still SO EARLY in AI… We’re still seeing mostly skeuomorphic uses! (It’s a real word!)

(48:06) William Gibson was right: “The Street finds its own uses for things”

(51:11) How AI startups should think about margins

(55:58) Why LAUNCH tells founders to “start at the high end”

(57:33) Should founders spend a lot of $$$ on marketing in 2025? The panel disagrees!

(1:00:05) Momentum vs. Product Release Velocity

(1:03:26) It all comes back to the “relentlessness of the founder”

(1:05:17) Our panel’s hopes and dreams for the coming year

*

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

Check out the TWIST500: 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/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:

(11:58) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at http://uber.com/ai-solutions

(19:57) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year. 

(29:46) 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!

“The best founders find a way to make it happen”: VC Roundtable with Bryan Kim and David Clark | E2222

This Week In Startups is made possible by:

Goldbelly - Goldbelly.com

Every.io - http://every.io/

Zite - zite.com/twist

Today’s show:

Today, Zapier’s a multi-billion company helping enterprises integrate AI agents and other time-saving shortcuts into their workflows… but we had the founder on TWiST when they were just getting started!

In a 2016 chat, founder Wade Foster walked JCal through their 2012 seed round, running a small entirely remote team with no HQ, the complexities of building a tool that relies on third-party APIs, and why Microsoft Office was the “Holy Grail” for his integration software.

PLUS we’ve got a new entrant in your Gamma Pitch Deck competition! Tour CEO/CTO Amulya Parmer tells us how his app is saving property managers time and grief, while eliminating “looky-loos” and increasing their “hit rate.”

FINALLY, Alex chats with Tomas Puig of TWiST 500 marketing analysis startup Alembic. It turns out, LLMs aren’t ideal for scrutinizing marketing campaigns because they lack the requisite historical data. Find out how they’re using Spiking Neural Networks (SNN) to dig deeper than GPT and Claude can go.

Timestamps:

(02:40) Amulya from Tour opens the show with praise for Jason

(03:34) Tour’s 2-minute Gamma pitch: automated property tours for managers

(06:47) Why Jason thinks Tour is an ideal tool for Gen Z

(10:01) Goldbelly - Goldbelly ****ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.

(13:32) How Tour can eliminate “looky-loos” and increase the “hit rate”

(14:38) Why Tour prices based on individual properties and apartments

(19:13) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.

(20:23) Jason wants to sprinkle some AI into Tour

(24:29) Welcoming Tomas Puig from Alembic

(25:12) Does epic-scale brand marketing actually pay off for these brands?

(27:27) The hardest thing about being a marketer…

(28:31) Alembic’s origins: organizing huge unstructured data sets

(30:18) Zite - Zite is the fastest way to build business software with AI. Go to zite.com/twist to get started.

(31:27) Case Study: making sense of Delta’s Olympics data

(33:37) Applying simulation models and supercomputers to marketing data

(35:48) How Spiking Neural Networks (SNN) help Alembic spot trends and link causal relationships

(41:13) The key advantage of training models on private data

(43:16) Building their own clusters vs. renting

(44:41) “You don’t ask if you have Product Market Fit… You hold on for dear life.”

(46:28) Flashback with Alex and Lon to Jason’s 2016 chat with Wade Foster of Zapier

(54:48) The dangers of building atop other platform’s APIs

(01:03:00) What Zapier learned pre-pandemic about leading remote teams

(01:13:12) Why MS Office was the “Holy Grail” for early Zapier

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:

(10:01) Goldbelly - Goldbelly ****ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.

(19:13) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.

(30:18) Zite - Zite is the fastest way to build business software with AI. Go to zite.com/twist to get started.

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

FLASHBACK: The future of remote work, juggling APIs, and dream integrations with Wade Foster of Zapier | E2221

This Week In Startups is made possible by:

Goldbelly - Goldbelly.com

Every.io - http://every.io/

Zite - zite.com/twist

Today’s show:

Today, Zapier’s a multi-billion company helping enterprises integrate AI agents and other time-saving shortcuts into their workflows… but we had the founder on TWiST when they were just getting started!

In a 2016 chat, founder Wade Foster walked JCal through their 2012 seed round, running a small entirely remote team with no HQ, the complexities of building a tool that relies on third-party APIs, and why Microsoft Office was the “Holy Grail” for his integration software.

PLUS we’ve got a new entrant in your Gamma Pitch Deck competition! Tour CEO/CTO Amulya Parmer tells us how his app is saving property managers time and grief, while eliminating “looky-loos” and increasing their “hit rate.”

FINALLY, Alex chats with Tomas Puig of TWiST 500 marketing analysis startup Alembic. It turns out, LLMs aren’t ideal for scrutinizing marketing campaigns because they lack the requisite historical data. Find out how they’re using Spiking Neural Networks (SNN) to dig deeper than GPT and Claude can go.

Timestamps:

(02:40) Amulya from Tour opens the show with praise for Jason

(03:34) Tour’s 2-minute Gamma pitch: automated property tours for managers

(06:47) Why Jason thinks Tour is an ideal tool for Gen Z

(10:01) Goldbelly - Goldbelly ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.

(13:32) How Tour can eliminate “looky-loos” and increase the “hit rate”

(14:38) Why Tour prices based on individual properties and apartments

(19:13) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.

(20:23) Jason wants to sprinkle some AI into Tour

(24:29) Welcoming Tomas Puig from Alembic

(25:12) Does epic-scale brand marketing actually pay off for these brands?

(27:27) The hardest thing about being a marketer…

(28:31) Alembic’s origins: organizing huge unstructured data sets

(30:18) Zite - Zite is the fastest way to build business software with AI. Go to zite.com/twist to get started.

(31:27) Case Study: making sense of Delta’s Olympics data

(33:37) Applying simulation models and supercomputers to marketing data

(35:48) How Spiking Neural Networks (SNN) help Alembic spot trends and link causal relationships

(41:13) The key advantage of training models on private data

(43:16) Building their own clusters vs. renting

(44:41) “You don’t ask if you have Product Market Fit… You hold on for dear life.”

(46:28) Flashback with Alex and Lon to Jason’s 2016 chat with Wade Foster of Zapier

(54:48) The dangers of building atop other platform’s APIs

(01:03:00) What Zapier learned pre-pandemic about leading remote teams

(01:13:12) Why MS Office was the “Holy Grail” for early Zapier

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:

(10:01) Goldbelly - Goldbelly ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.

(19:13) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.

(30:18) Zite - Zite is the fastest way to build business software with AI. Go to zite.com/twist to get started.

Great TWIST interviews: 

Will Guidara

https://youtu.be/pvJa2pzuXWQ

Eoghan McCabe

https://youtu.be/9dHN4YFkgv4

This Week In Startups is made possible by:

Superhuman - https://superhuman.com/podcast

Squarespace - https://squarespace.com/twist

Enterpret - https://www.enterpret.com/dlp/this-week-in-startups

Today’s show: 

A screenshot showing a “Target Ad” in ChatGPT results went viral… over the weekend, but the OpenAI chatbot has NOT actually opened the advertising floodgates just yet.

As ChatGPT staffers were quick to explain on social media, this was actually an invitation for a user to integrate their Target account into ChatGPT, for an easier agentic browsing and shopping experience.

But it does prompt Jason and Alex to ask some intriguing questions… Is OpenAI just waiting for Google or someone else to launch AI ads first, and face the inevitable flood of backlash they’ll presumably receive? Is there someone at OpenAI already thinking DEEPLY about how these in-feed ads should work? And what does this mean for their wager on when ChatGPT is going to actually get ads? Is that already decided?

These answers and more are coming your way on today’s action-packed TWiST… PLUS the latest on the Warner Bros Discovery-Netflix deal, PR guru Lulu Cheng Meservey’s new venture fund, and why Jason and Lon are obsessing about Apple TV’s “Pluribius.”

Timestamps:

(01:59) They put Target ads in ChatGPT? Or was it just an integration? Is there a difference?

(5:24) Is someone at OpenAI really thinking deeply about how in-feed ads should work?

(07:36) Is OpenAI just waiting for Google to start running ads to post their own? Jason has suspicions…

(10:01) Why Jason thinks startup people have so much trouble communicating with normies

(10:32) Superhuman - Get AI that works where you work. Unlock your Superhuman potential at http://superhuman.com/podcast

(13:22) The insane competition now facing down OpenAI and Sam Altman

(18:40) Why Jason will no longer use data from SaaS companies looking for a marketing win

(19:52) Does this mean ChatGPT TECHNICALLY has ads? Does Alex win the bet?! What does Polymarket think?

(20:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(25:17) Why Jason is already tired of the Netflix-Paramount-WBD story

(30:06) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to http://Enterpret.com/twist to book a demo and see it in action.

(34:03) President Jason’s new proposal: A 60-day “pre-approval” antitrust window

(47:29) Why Jason’s not interested in news commentary… just the facts.

(51:40) Jason and Lon take a few moments to praise “Pluribus”

(54:45) PR guru Lulu Cheng Meservey is starting a venture firm… here’s why she wants to start a “movement”

(58:05) Why PR people hate but also respect Jason

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

Check out the TWIST500: 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/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:

(10:32) Superhuman - Get AI that works where you work. Unlock your Superhuman potential at http://superhuman.com/podcast

(20:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(30:06) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to http://Enterpret.com/twist to book a demo and see it in action.

What’s REALLY going on with those “ads” in ChatGPT | E2220

This Week In Startups is made possible by:

Sentry - http://sentry.io/twist

LinkedIn Ads - http://linkedin.com/thisweekinstartups

Pipedrive - pipedrive.com/twist

Today’s show:

Netflix wants to gobble up Warner Bros. Do they just want to own Batman and Harry Potter, or is this secretly about destroying movie theaters?

Sure, this is usually a startup show, but news THIS BIG warrants attention! So Lon stops by to tell Jason and Alex about the big Netflix acquisition news, why so many theatrical movie fans are terrified for the future, and why this might face particular regulatory scrutiny both at home and abroad.

PLUS… are Googlers gaming Polymarket? This is one scenario in which prediction markets are NOT exactly like stocks.

THEN we’re looking at some of our favorite startups from the Fall ‘25 Y Combinator cohort (and asking Producer Claude for his picks)… Considering why Perplexity keeps getting sued and how they can stop it… and doing a victory lap for Jason’s early investment in breakout AI training project Micro1.

Timestamps:

(02:05) Netflix buying Warner Bros! Jason, Lon and Alex react.

(05:04) Jaytrade Update: J kind of missed the boat on this one

(05:36) What does this mean for theatrical cinema?

(08:42) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(09:52) Jason’s pitch to Disney CEO Bob Iger (please send this to him!)

(19:36) 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.

(23:29) Is this deal going to get approval, at home and abroad?

(25:52) Are Googlers gaming Polymarket?

(28:02) Can you do “insider trading” on a prediction market?

(29:23) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at pipedrive.com/twist

(37:00) How accelerators like Y Combinator serve as “finishing schools” for startups

(37:52) A Quick Look at some of our fav companies from YC’s Fall ’25 cohort

(39:01) Why startups need to “skate to where the puck is going”

(40:08) Why sometimes old ideas (like solar-powered aircraft) are often worth revisiting

(45:29) Jason’s advice for founders (and investors) in the “feel good” or activist space

(50:48) Why Lon, Alex, and Claude ALL thought Hyperspell sounds like a hot startup

(52:58) Perplexity getting sued again! Why can’t they make friends!

(57:51) Meanwhile, Meta’s signing AI deals with news publications.

(59:21) Micro1, which Jason helped to fund, has hit $100M ARR! Why do AI companies need so many experts?

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:

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Netflix buys WB + why Jason should run Disney | E2219

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Today’s show: 

Delegating is its own unique skill, requiring training and a real investment of time and attention.

On TWiST, Jason chats for a full hour with the founder of one of his favorite startups, Athena, which trains online assistants and pairs them with busy founders and executives. (Jason has 2!) 

But getting the MOST out of your executive assistants is less obvious than it looks. Jonathan unpacks some of the secrets to “Black Diamond Delegating,” and how he manages to keep 6 different high-level helpers operating at once.

Plus, Jason and Jonathan look back at the Open Angel Forum days, where Jason invested in Jonathan’s previous company, Thumbtack, praise the “Checklist Manifesto,” discuss the telltale signs you’ve achieved market pull, and lots more insights.

Timestamps:

(01:53) We’re joined by Jonathan Swanson from one of JCal’s fav startups, Athena!(02:02) Jason and Jonathan first met during the Open Angel Forum, when Jonathan was working on Thumbtack(06:44) Finding the “little touches” that can help make an app more delightful(9:47) 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!(12:05) The shift from Thumbtack to Athena was all about time(12:52) How Jonathan delegates to 6 exec assistants at once(14:22) Pricing Athena’s EAs: Jason runs the numbers(15:09) Why Athena made Jason believe in hiring assistants again(18:15) Getting past the “Cardinal Sins of Delegation”(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(20:48) Will AI ever be able to replace Athena assistants?(23:41) Inside how Athena finds and trains assistants from around the world(27:01) How JCal became an Athena Ambassador… and almost crashed the system!(30:55) 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 https://www.gusto.com/twist(32:11) The magic of having assistants work on “backstop projects” and creative tasks(37:14) How to know when you have achieved market pull(40:05) Why getting the most out of delegating takes real investment and training(44:36) More praise for the Checklist Manifesto(46:26) Jonathan gives us a peek at what “Black Diamond Delegation” looks like(52:14) Jason’s early experiences hiring overseas assistants, from the Mahalo days*Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://twist500.comSubscribe 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: https://www.linkedin.com/in/alexwilhelm/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis/*Thank you to our partners:(9:47) 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!(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(30:55) 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 https://www.gusto.com/twist

Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218

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Today’s show: 

Did you know there’s actually a shortage of US bricklayers? It’s TRUE! So feel free to marvel at Monumental’s brick-laying robots. They’re not putting anyone out of work, but filling a much-needed gap.

Join Alex and Monumental founder/CEO Salar al Khafaji for a deep-dive on how the startup is making construction robots play nice together by maintaining separate “zones” of operation, why Salar thinks startups need to focus on truly complex, real-world problems to truly blossom, and the secrets of fundraising in Europe.

PLUS Alex chats with Seasats CEO Mike Flanigan about designing the next generation of autonomous marine crafts. (That is to say, ocean drones.) From their home base in San Diego, the company is trying to get completely independent of all Chinese parts. Find out how it’s going, how they’re overcoming the “wildly negative” ROI on maritime tech, and why we have so few defenses against tiny, agile drones.

All that AND Jason takes some of YOUR Founder Questions.

Timestamps:

(03:23) How Monumental determined what kinds of robots construction sites need the most

(06:49) How maintaining “zones” ensure that the robots all play nice with one another

(07:52) There’s a shortage of bricklayers, so Monumental’s NOT taking anyone’s job

(9:16) 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.

(13:21) Why startups need to tackle large-scale, complex, real-world problems to really grow

(15:44) Why Monumental is building in The Netherlands, and running pilots in the UK

(19:07) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(20:44) Why construction is unique among applications for automation and robots

(26:01) Salar argues that fundraising in Europe is not as hard as you may have heard

(27:55) We don’t just need housing, we need BEAUTIFUL housing

(31:11) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year. 

(33:25) How the Scout autonomous boat challenge inspired Seasats

(35:28) Trying to make drones into an “iPhone Style” project

(37:39) Why Seasats is focused on endurance and staying power more than launches

(39:15) The complexities of working with fuel cells

(42:27) The importance of beautiful design even when working on government technology

(45:51) Why they’re building Seasats in beautiful San Diego, CA

(47:29) The challenge of getting entirely free from Chinese components

(53:52) “The Power of Small Things Has Changed”

(55:18) The “wildly negative” ROI on most humanoid robotics companies also applies to maritime tech

(59:09) Why there are so few defense nets against people with tiny but agile drones

(01:02:32) FOUNDER Q’s: Is a founder working 24/7 a red flag?

(01:10:11) How bad is it to use VC money to pay off credit cards?

(01:12:49) A look at Cursor’s unique recruitment strategy.

(01:19:57) Should young VCs go to startup conferences?

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(9:16) 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.

(19:07) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(31:11) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

Monumental Makes Construction Bots Play Nice Together | E2217

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Today’s show: 

Michael Saylor’s Strategy play is struggling with the price of Bitcoin on a steep decline… Is his new “dollar reserve” the answer?

On TWiST, we’re looking into the state of $MSTR and why Jason remains SO skeptical about this increasingly convoluted financial scheme.

Is CNBC giving Michael Saylor a pass? Is that why he won’t go on “All-In”? And do investors realize that loans go BEFORE equity? We’re asking the TOUGH questions…

PLUS Jason’s Four Red Flags for companies with convoluted tactics… Why S&P Global downgraded Tether, and why Jason thinks the US government waited TOO LONG to pass stablecoin regulations… Jason reacts to the NYT “hit piece” on Bestie David Sacks… we’re checking out the new Matic robot vacuum and Sunday Robotics’ Memo bot… PLUS much more of the day’s biggest tech news and stories.

Timestamps:

(03:04) Why Jason broke his “No Demo Day” rule for the LAUNCH 35 Accelerator

(07:08) What we can learn from BitcoinTreasuries.net about the marketplace

(07:42) Why Jason remains SO skeptical on $MSTR… and any sufficiently convoluted financial scheme…

(7:56) Jason’s Four Red Flags for rogue companies and financial schemes

(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST

(14:31) When loans go before equity, and how this can dilute your investment!

(18:05) Is CNBC giving Michael Saylor a pass? Why Jason thinks he won’t go on “All-In.”

(19:30) Checking in with Polymarket’s thoughts on potential MicroStrategy Bitcoin sales

(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(22:58) Speaking of complex schemes… why S&P Global downgraded Tether

(29:26) Is Tether too good to be true, as an investment?

(25:17) Why Jason thinks the US waited too long to pass stablecoin regulations.

(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!

(36:15) Jason’s reaction to the NYT piece about Bestie David Sacks

(43:14) Is there a growing divide within the GOP about how to engage with tech companies?

(44:04) What are “Glue Employees” and why are they important?

(45:03) How to tell your “Glue Employees” apart from the “union reps” and other rabble rousers…

(51:50) Sunday Robotics: another human-ish robot but with WHEELS (and a baseball cap)

(56:05) We’re checking out the Matic robot vacuum as well… Should these products be combined?

*

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

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Thank you to our partners:

(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST

(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!

Great TWIST interviews: 

Will Guidara

https://youtu.be/pvJa2pzuXWQ

Eoghan McCabe

https://youtu.be/9dHN4YFkgv4

Steve Huffman

https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424

Brian Chesky

https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112

Is $MSTR over? Jason takes his victory lap. | E2216

Today’s show:

Jason sits down with Wilson Sonsini partner Chris Paniewski for part two of our Startup Legal Basics series on AI law — this time tackling the question every founder is asking: who owns the output of AI systems?

Chris has advised on some of the biggest AI deals in history, and in this episode he helps break down how intellectual property law is colliding with generative AI.

Jason and Chris cover:

 • What kinds of IP rights might apply to AI-generated output (
copyrights, patents, trade secrets • )
 • Why human authorship is central to copyright law
 • Whether prompts are protectable IP
 • How GenAI platforms’ terms of service affect ownership
 • Real-world examples from Star Wars to Wirecutter to Warhol
 • What startups should document when using AI in development
 • How investors diligence AI companies on IP strategy

If you’re a founder, investor, or operator trying to understand how to responsibly use AI without losing your IP, this conversation is essential.

*

Timestamps:

(0:00) Jason introduces part two of Startup Legal Basics with Chris Paniewski

(1:20) Star Wars example: using LLMs to generate existing IP

(3:10) Human authorship requirement in copyright law

(5:25) Prompts, super-prompts, and the role of creative control

(7:45) Photography analogy & the “monkey selfie” case

(10:00) Patents, inventorship, and AI-generated inventions

(12:05) Startups balancing speed to market vs. protectable IP

(14:15) How to layer human creativity on top of AI output

(16:20) Fair use, derivative works, and investor diligence

*

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

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

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Who Owns the Output? AI Copyright & IP Explained w/ Chris Paniewski | Startup Legal Basics

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