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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:

Gusto - https://www.gusto.com/twist

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

Quo - http://quo.com/TWiST

Today’s show: 

We keep hearing about how AI is killing our ability to think, filling our media with slop, and ruining our kids’ ability to learn. It seems the internet is filled with negative sentiment about the future AI is bringing.

Jason is joined by Grant Lee, CEO and co-founder of Gamma, as well as Steven Johnson, editorial director of NotebookLM to tackle these questions on today’s AI roundtable!

Grant and Steven break down how they are using AI to push forward their own productivity as well as their teams. Both say that AI makes you more creative! Steven points out that it helped him write his books by having AI do the “chore work” while he got to focus on the valuable insights and higher level thinking.

One valuable tip was that AI can be used to uncover customer insights in a new medium. Steven and Grant both put customer feedback into an LLM, allowed them to have high level conversations with their whole user base about what features and products they each enjoy. If that isn’t creative, then what is?

Learn about all this and more in today’s roundtable!

Timestamps:

(00:00) Introducing Steven Johnson and Grant Lee!

(10:12) 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

(11:28) How Jason and the TWiST team uses NotebookLM

(12:37) Will AI replace lawyers in startups and VC? Should they?

(16:08) How the Gamma team uses AI understand their consumers

(19:43) Lemon.io: Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

(22:38) How the Google team uses AI to “talk” to their whole user base.

(24:45) Is AI replicating our brains and consciousness?

(28:18) The ways that AI is changing how companies process information.

(30:39) 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

(31:43) Jason thinks groupchats are the modern coffee shop for interesting ideas!

(32:48) Why Steven thinks AI makes creatives MORE ORIGINAL

(40:02) HALF of US adults think AI makes you less creative

(43:20) Grant defends using AI for doing research + making business decisions

(45:28) Superforecasting — How to think about your thinking

(53:00) Is education going back to blue books and oral exams?

(56:30) Jevons Paradox and How AI will increase jobs for all!

(59:50) Edison put whale hunters out of business but brought in electricians and movie industry

(1:02:36) Jason coaches his employees to 10x themselves with AI tools to push value

(1:05:54) Jason’s call to join the AI revolution

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X: https://x.com/lons

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X: https://x.com/alex

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

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

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Thank you to our partners:

(10:12) 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

(19:43) Lemon.io: Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

(30:39) 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

AI makes you more creative, AI Roundtable with Steven Johnson and Grant Lee | E2231

This Week In Startups is made possible by:

Crusoe Cloud - https://crusoe.ai/build

Uber - http://uber.com/twist

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

Today’s show: 

Jason and Alex are BACK on TWiST for 2026! 

This holiday season was anything but calm, with deca-corn acquisitions, massive Polymarket bets, and major new startups breaking from stealth!

Jason talks the recent Nvidia-Groq $20B acquisition, a major exit for Chamath as the lead investor back in 2017! Jason delves into how the VC fund math shapes out for pre-seed VC funds vs. Series A VC funds.

Jason and Alex delve into drama swirling META’s AI team. Yann LeCun, META’s former Chief AI Scientist, announced that he would be leaving META to become Executive Chairman at AMI Labs. LeCun left the META team in the new year, calling the new Chief AI Scientist, Alexandr Wang, inexperienced. LeCun now looks to move AI beyond the era of LLM at AMI Labs.

PLUS Jason and Alex talk about the new social media app Tangle, from Biz Stone, co-founder of Twitter, and Evan Sharp, co-founder of Pinterest. Their Startup, West Co, launched tangle, which seeks to become an “intentional living” app. The two look to improve how humans interact with modern tech. Jason points out that very few news products have worked, but is eager to see how two industry veterans build in the space. 

Timestamps:

(00:00) Why Restaurants are OVER — Peptides and other self medications

(06:41) Nvidia Acqui-Hires Groq for $20 BILLION

(9:48) 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.

(11:00) The VC fund math between seed vs. Series A funds

(15:00) META buys TWiST 500 Company, Manus! Why it matters.

(20:20) 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/twist

(21:24) Why Yann LeCun left META, and what could be behind it

(25:27) Producer Claude on the Gondola Crash in Zurich

(29:13) Jason’s Request for Augmented human intelligence

(30:11) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit http://every.io/

(32:04) How one Trader made $436.8k on one bet on polymarket!

(36:05) Jason’s Predictions for 2026 IPOs

(40:01) Is news broken? How Tangle is tackling it.

(45:53) How much should startup incur in legal expenses? Should founders try to use AI to avoid costs?

(50:59) Why Google should let NotebookLM cook, make it a standalone brand! 

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Follow Lon:

X: https://x.com/lons

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Follow Alex:

X: https://x.com/alex

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

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Follow Jason:

X: https://twitter.com/Jason

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

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Thank you to our partners:

(9:48) 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.

(20:20) 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/twist

(30:11) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit http://every.io/

2026 Starts with a bang: META AI Drama and Nvidia’s $20B Groq Acquisition | E2230

This Week In Startups is made possible by:

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

Squarespace -https://squarespace.com/twist

Hubspot - http://clickhubspot.com/twist1

Today’s show: 

We’re saying goodbye to 2025 with our annual TWISTY Awards, looking back on our favorite pod moments from throughout the year.

Featured clips include Jason’s message to the members of Reddit’s r/AntiWork community…

Why JCal would NEVER work with Sam Altman or OpenAI…

The time that Jason got doxxed and then found the guy responsible on LinkedIn…

Why LA Mayor Karen Bass earned a *disgraziad*…

Alex saying “Yessir!” in a weird way…

And much more classic TWiST content.

See y’all next year!

Timestamps:

(00:00) It’s the final episode of the year: The TWiSTY Awards for our favorite moments and guests of the year

(2:06) The nominees for Best Name Drop

(7:02)2025 in Trends

(9:52) 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.

(14:28) The best Jason anecdotes and personal stories

(19:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(22:28) Our favorite 2025 guests, including Doug Leone, Coffeezilla, Anton Osika, and more

(29:03) The year in Jason Rants

(30:18) Hubspot: Check out the guide “How to Get Your First 100 Customers.” Download it for free at http://clickhubspot.com/twist1

(36:11) Controversial moments and the year’s hottest takes

(44:11) DISGRAZIAD! Here are the most shameful people and companies of 2025

(50:50)Alex’s best/worst Dad Jokes

(54:32) It’s a simple word… groceries

*

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

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Follow Lon:

X: https://x.com/lons

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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/

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Thank you to our partners:

(9:52) 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.

(19:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(30:18) Hubspot: Check out the guide “How to Get Your First 100 Customers.” Download it for free at http://clickhubspot.com/twist1

THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and more | E2229

This Week In Startups is made possible by:

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

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

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

Today’s show: 

Jason’s already a millionaire many times over… but what are the huge, blockbuster, dream purchases that he’s still holding off on? BESIDES the private jet we all know he wants? The Noti Gang has asked, and JCal finally answers, on a holiday TWiST where we’re taking questions from viewers and fans.

Check out the episode for lots more intriguing queries, like how to push forward and glean useful information when your first customers aren’t using your product the way you’d envisioned. Plus, is there room for both AI agents and great SaaS startups in the coming years? Hear why Jason thinks there IS.

AND we’ve got the very last Gamma Pitch Deck Competition entry before we announce our winner in the new year. Check out AskHumans, an innovative approach to improving market research.

Timestamps: 

(00:00) On a special holiday TWiST, we’re answering YOUR pressing Founder Questions!

(8:35) 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!

(09:35) What should a founder do when a VC reaches out cold?

(13:37) The importance of maintaining “ball control”

(15:35) A European founder asks: Should I take European investments if they’re targeting American customers?

(19:47) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(20:51) A member of the Noti gang asks for JCal’s dream mega-purchases

(24:12) Why Jason thinks there’s room for BOTH AI agents and great SaaS companies

(27:18) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

(28:23) It’s our final Gamma pitch with Zak from AskHumans!

(29:24) How AskHumans uses AI to improve on marketing surveys and research

(34:33) Management and measurement were designed before computers could understand language… why this matters.

(35:48) Why no one ever wants to give feedback in a video

(39:01) Why Zak’s pitch is “two chapters of the same story”… and was this a pivot?

(44:14) Why founders need to assume LLMs are going to get exponentially better

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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

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Follow Alex:

X: https://x.com/alex

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

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Follow Jason:

X: https://twitter.com/Jason

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

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Thank you to our partners:

(8:35) 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!

(19:47) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(27:18) 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

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week In Startups is made possible by:

Caldera + Lab - http://calderalab.com/TWIST

Crusoe Cloud - https://crusoe.ai/build

Uber - http://uber.com/twist

Today’s show: 

Why did a power outage in the Bay Area cause Waymos to pile up on city streets?

Jason was actually in San Francisco to take in the spectacle of Waymos blocking traffic. But why did this happen? And can we look forward to a day when automated cars are more graceful and coordinated than ballet dancers performing “Swan Lake”? We’re asking the tough (and also culturally erudite) questions!

PLUS self-driving cars are coming to London, Coinbase’s buying spree continues, another entrant in our nearly-complete Gamma Pitch Deck Competition, AND why Jason predicts that Google is going to buy UBER!

You won’t want to miss this holiday TWiST!

Timestamps:

(00:00) It’s a holiday TWiST! Jason’s calling in from vacay in Lake Tahoe.

(03:11) Jason was in SF for the great Waymo power outage!

(06:06) Why Jason says one day Waymos will be better coordinated than dancers in “Swan Lake”

(07:33) We predicted Starlink coming to every Tesla nearly 3 years ago!

(09:05) Caldera + Lab: Whether you’re starting fresh or upgrading your routine, Caldera Lab makes skincare simple and effective. Head to http://calderalab.com/TWIST and use TWIST at checkout for 20% off your first order.

(11:29) Jason calls what Tesla’s Optimus team is planning “otherworldly”

(14:39) Why Jason thinks we’re all going to live in an “Opt-In Truman Show” someday soon

(18:52) Baidu, Lyft, and Uber bring self-driving cars to London… they don’t have them already?!

(20:49) 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.

(24:02) When do we get to 50% of all rides being done by autonomous vehicles… and how many robotaxis will that take?

(27:50) Why Jason thinks Google is going to buy… UBER?!

(31:12) 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/twist

(32:30) Will it eventually come down to which car can drive a mile for the cheapest?

(35:08) Coinbase picks up The Clearing Company, which makes frameworks for prediction markets

(39:50) How much did the biggest AI models improve this year?

(44:09) Who’s going to actually buy Warner Bros? We’re checking the Polymarket.

(47:06) GAMMA PITCH w/ Jonathan Sherman of Lumix Ads

(51:00) Why Jason says Jonathan’s pitch is a 9.5 out of 10

(52:50) What Jason looks for in a founder: “a big audacious vision”

(54:18) How Lumix (safely) collects users’ “mobile ad ID” on the go to identify them

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:

(09:05) Caldera + Lab: Whether you’re starting fresh or upgrading your routine, Caldera Lab makes skincare simple and effective. Head to http://calderalab.com/TWIST and use TWIST at checkout for 20% off your first order.

(20:49) 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.

(31:12) 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/twist

Waymo Madness in SF! Why robotaxis clogged the streets | E2227

This Week In Startups is made possible by:

Luma AI - https://lumalabs.ai/twist

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

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

Today’s show: 

DID YOU KNOW… most of the tried and true techniques devised by marketing gurus in the ‘40s and ‘50s still apply today?

On TWiST, we’re joined by online marketing expert Sam Parr, host of “My First Million” and founder of Hampton. He’s sharing all of his top tips and tricks for making your writing more compelling, and converting your readers into new customers.

In this essential pod for any and all founders, hear Jason and Sam run down their list of the best-ever marketing books, why there’s no such this as “too long” only “too uninteresting,” when to use AI and when to rely on your own brain, why you’re the average of your five best friends, and lots more deep insights.

Timestamps:

(00:00) Sam Parr of The Hustle, Hampton, and My First Million is here to teach us how to become better copywriters

(03:59) How Sam got interested in the (then-shady) world of internet marketing

(06:26) Why Sam recommended THESE advertising books to Jason

(08:15) All the principles that ad execs developed in the ‘50s still work!

(09:43) Glengarry had it right; the magic of A.I.D.A.

(11:19) Luma AI - Stop guessing and start directing with Ray3 Modify from Luma AI, the AI-powered post production tool. Explore it at: https://lumalabs.ai/twist

(14:30) There’s no such thing as “too long,” just “too uninteresting”

(16:15) The goal is to write at a 4th grade reading level

(18:12) Why Sam only uses AI for “The Big Idea,” not the actual writing

(19:37) Why you’re the average of your five best friends

(21:14) 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!

(22:15) Using AI to dig in and research, to make your writing more interesting

(23:42) CopyWork: The technique that helped Sam fine tune his writing

(28:41) Avoiding “The Feature Death March”

(30:56) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

(32:00) Words are better than images, but videos are better than anything

(34:43) Why stories make such a huge impact

(37:36) Sam and Jason are both obsessed with the book “How to Be Rich”

(43:02) First World Problems are still problems!!

(44:31) Why Sam launched Hampton and what it takes to get in

(47:10) Why scaling a community is so much harder than launching

(51:04) The lessons founders can take from Ted Turner

(58:36) What Jason likes best about My First Million

(1:00:28) It’s never too early to get your first $10 million

(1:04:07) How accurately did Producer Claude guess what Sam was going to teach us?

*

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:

(11:19) Luma AI - Stop guessing and start directing with Ray3 Modify from Luma AI, the AI-powered post production tool. Explore it at: https://lumalabs.ai/twist

(21:14) 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!

(30:56) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

Level up your copywriting w/ Sam Parr | E2226

This Week In Startups is made possible by:

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

Squarespace - https://squarespace.com/twist

Enterpret - http://Enterpret.com/twist

Today’s show: 

How do top tech CEOs hire? AI has thrown out the playbook for getting hired — so what are the most innovative firms looking for? Anyone can learn any skill and automate much of it, what is to be valued in the modern labor market?

On our first AI Roundtable episode of TWiST, Jason is joined by three top tech CEOs: Wade Foster (Zapier), Mikey Schulman (Suno), and Ali Ansari (Micro1). They each give their perspective on the tech talent wars and how to get hired in 2026.

The resounding answer on how to get a job? JUST START DOING THE JOB! If you want to be a designer, start sending designs to companies you want to be hired by — don’t just sit around waiting to be hired. The biggest value you can bring is a “high agency” mindset to your company and the role. Show you get after it!

They are also hitting on:

- How AI is getting used to make music today

- The tech industry’s communication problem

- How to raise kids in the age of AI

Timestamps:

(00:00) It’s our first ever “This Week in AI” Roundtable, and we’ve got an amazing panel

(05:50) How Meta and OpenAI skew how everyone thinks about compensation

(09:37) The importance of looking beyond SF for talent

(10:24) 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.

(14:39) Is AI making more people seek out developer jobs?

(18:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(19:36) When design becomes its own bottleneck… and some workarounds.

(22:37) It’s not how much you know, it’s how adaptable you are

(24:10) The best way to get hired: just start doing the job

(30:09) Why Ali says we’re entering the "Post-Training"

(31:34) 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.

(33:32) Understanding the value of your company’s data and using it to get better outputs

(41:14) Mikey calls Suno the “GLP-1s of the music industry”: everyone uses it but no one admits it

(46:39) Mikey Talks break out AI artists like Xania Monet

(49:32) Questions raised about how AI will effect job markets

(54:43) How AI and robotics will unlock new jobs and opportunities

(58:48) Possible solutions to the AI and automation question.

(01:04:03) Technology's communication problem and how to fix it.

(01:05:24) Are people replacing their friends with AI?

(01:08:11) How CEOs are thinking about raising young kids in the world of AI.

(01:12:21) Lightning round on AI agents, workflows vs. agents

(01:16:49) Trapped value in sales calls, questions, company meetings that are unlocked by AI

(01:22:10) How Ali pitched the LAUNCH team outside of a Jeni's Ice Cream store

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 Jason:

X: https://twitter.com/Jason

Thank you to our partners:

(10:24) 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.

(18:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(31:34) 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.

INSIDE How AI Startups hire, AI Roundtable with Wade Foster, Mikey Schulman, and Ali Ansari | E2225

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

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Follow Alex:

X: https://x.com/alex

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

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X: https://twitter.com/Jason

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

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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

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Follow Lon:

X: https://x.com/lons

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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/

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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

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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

Follow Arlan: https://twitter.com/ArlanWasHere

Join Backstage Crowd: http://backstagecrowd.com

Follow Jason: https://twitter.com/Jason

https://linktr.ee/calacanis

E1080: Arlan Hamilton on launching Backstage Crowd, disrupting VC with syndicates, how the tech industry can be better for underrepresented founders & more

E1080: Arlan Hamilton on launching Backstage Crowd, disrupting VC with syndicates, how the tech industry can be better for underrepresented founders & more

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