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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:

On a brand-new TWiST, Jason and Alex are asking why there are SO MANY note-taking AI apps?

Plus another death has been linked to ChatGPT… is it too easy to get past chatbot guardrails? Why Donald Trump Jr. is joining Polymarket…. How the US Navy could catch up with its international rivals… AND should Apple just buy a big AI company to help them catch up?

All that PLUS a visit from Colin Russ, whose viral H1B Visa thread might just inspire Jason to reach out to his good friend, Vice President JD Vance. Check out the full episode!

Timestamps:

(0:00) Intro, Jason’s checking out Notion’s new AI note taking app… is it time to cancel Granola?

(06:57) How Google Gemini’s new 2.5 Flash Image tool (formerly known as “nano-banana”) could change advertising

(10:28) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(11:40) Show Continues…

(17:50) Another death linked to ChatGPT… is it too easy to get around AI chatbot guardrails?

(19:26) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

(20:34) Show Continues…

(28:10) Donald Trump Jr. invests in Polymarket and joins the board…

(29:45) 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!

(30:49) Show Continues…

(33:30) How Jason thinks the US Navy could catch up with China and other rivals, with help from startups

(40:01) Do Jason and Alex think Apple might REALLY buy a big, expensive AI company? Would that be admitting defeat?

(45:57) Colin Russ (@ThaaatColin) tells us about his viral X thread and why he’s worried about H1B visa fraud

(55:32) Jason’s solution for the H1B system, and a message for VP Vance.

(01:08:25) Jason responds to Kara Swisher, who accused him sucking up to power

(01:19:07) Jason responds to his old pal Sam Harris, who thinks he’s loyal to the wrong people

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:

(10:28) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(19:26) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

(29:45) 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!

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

Google is Nano Banana, Apple AI plans & The Great H1B Visa Debate | E2170

Today’s show:

On an upbeat and optimistic new TWiST, Jason and Alex are debating why any new innovation or technology gets hit with a wave of bitter cynicism.

PLUS Jason defends the government taking shares of Intel, explains the importance of interoperability, and predicts how AirBnB’s Joe Gebbia will upgrade the US government’s website design.

All that PLUS thoughts on the Netskope IPO, Perplexity offering publishers actual revenue share, a deep dive on the new AI-based PAC, thoughts on open-source LLMs, and much much much more.

Timestamps:

(0:00) Cynicism vs. Optimism and why Jason thinks cynics go after any interesting new technology

(10:02) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(11:04) Show Continues…

(14:37) Why Jason supports the Intel deal but worries it will become a trend

(20:46) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.

(22:00) Show Continues…

(27:02) Is it hypocritical to oppose socialist grocery stores but support the Intel deal? Jason says NO.

(29:41) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(30:58) What does xAI hope to get out of this OpenAI/Apple lawsuit? Jason and Alex theorize…

(39:12) Why Jason thinks interoperability is so important and how App Stores OUGHT to work

(41:12) How AirBnB’s Joe Gebbia could potentially upgrade the US government’s websites

(49:27) What does Netskope do exactly? SASE?! Producer Claude explains…

(58:32) Alex and Jason celebrate Perplexity rev sharing with publishers

(01:10:02) Jason’s thoughts on the Leading the Future PAC, and US AI policy

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:

(10:02) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(20:46) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.

(29:41) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.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

xAI’s App Store lawsuit, Intel shares vs. grocery stores, and Netskope’s IPO | E2169

Today’s show:

Terra’s collapse, Powell’s pivot, and OpenAI’s explosive growth all collide in this TWiST deep dive.

Do Kwon has pled guilty after Terra/Luna’s $60B implosion, Fed Chair Powell hints at a September rate cut, and OpenAI has officially crossed $1B in monthly revenue (on a $12B run rate). Jason and Alex unpack what this means for founders, LPs, and the next wave of AI + crypto.

They also cover Canva’s $42B comeback, Anthropic’s doubled $10B fundraise, and the brewing battle between Figma & Canva.

Plus: Uber, Nuro & Lucid’s $6B robotaxi push — and why drivers are already protesting in Wuhan & Boston.

#Startups #Crypto #AI #VentureCapital #OpenAI #Anthropic #Canva #Figma #ThisWeekInStartups

Timestamps:

(0:00) INTRO

(01:15) Fed rate cut signals & market reaction

(05:36) Jason’s $400K in new fund bets

(10:25) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(11:30) Show Continues…

(16:22) Do Kwon & the Terra/Luna collapse

(20:22) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.

(21:23) Show Continues…

(29:43) 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

(30:55) Show Continues…

(36:14) OpenAI’s $1B/month revenue run rate

(42:13) Anthropic’s $10B round & AI market sizing

(51:31) Canva’s $42B valuation & Figma comparison

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:

(10:25) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(20:22) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.

(29:43) 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

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

Do Kwon Guilty, Powell Pivot & OpenAI’s $12B Run Rate | E2168

Today’s show:

In this TWiST 500 double feature, Alex sits down with two breakout founders: Chalk’s Marc Freed-Finnegan & Tollbit’s Toshit Panigrahi!

First, Chalk’s CEO Marc Freed-Finnegan is tackling one of AI’s biggest bottlenecks—data freshness. Instead of relying on stale batch jobs, Chalk delivers real-time pipelines for inference compute, automatically transpiling Python into C++/Rust so it can run blazing fast in production. Investors are calling it the ‘next Databricks’—and after hearing this convo, you’ll see why.

Then, Tollbit’s CEO Toshit Panigrahi returns after raising a $24M Series A and signing up 1,400+ publishers. With RAG traffic exploding and robots.txt losing its teeth, their ‘bot paywall’ could reshape how AI agents pay for the content they consume. Are we heading for a Spotify moment for data licensing?

A must-watch if you care about the economics of AI, from data pipelines to publisher monetization.

Timestamps:

(0:00) Intro + sponsors

(1:03) Alex tees up two Twist 500 interviews: Chalk & Tolbert

(2:47) Why AI is shifting from training compute to inference compute

(4:41) Data freshness & real-time inference explained

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

(12:00) How Chalk transpiles Python into C++/Rust for speed

(18:52) Chalk’s business model, margins & $500M valuation

(20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(21:24) Show Continues…

(28:02) Tollbit returns: $24M Series A & the rise of RAG bot traffic

(30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

(31:41) Show Continues…

(36:53) Robots.txt losing relevance & the case for bot paywalls

(39:19)Publishers, AI agents & the future economics of the web

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:

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

(20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

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

Is Chalk.ai the ‘Next Databricks’? + Tollbit’s Bot Paywall for AI Agents | E2167

In this AI Basics episode, Jason sits down with Matt Rouif, Co-founder & CEO of Photoroom — the AI photo editing app with 300M+ downloads and 5B images processed annually.

They break down:

 • Why Photoroom built its own specialized AI models
 • How they grew from a scrappy startup to $50M+ in revenue
 • Lessons in product-led growth (from eBay sellers to DoorDash & Amazon)
 • Red-teaming, brand safety, and building trust in AI imagery
 • The future of personalized ads, content, and design

This one is a masterclass for founders, operators, and builders.

Timestamps:

(0:00) Matt Rouif joins Jason to discuss AI Basics.

(0:45) Meet Matt Rouif: Photoroom’s $50M+ AI photo startup

(3:15) Live demo: background removal + virtual try-on

(7:40) From indie sellers to DoorDash & Amazon

(12:20) The “Barbie Movie” API moment

(17:05) Red-teaming AI: trust, safety & brand protection

(22:10) Running a 100-person AI startup

(26:30) The future of personalized ads (put you in the ad?)

Explore Further:

Google Cloud’s Report: The Future of AI

Get insights from 23 leading experts on how startups can leverage AI for real business impact.

👉 Read the full report

More AI Basics Episodes

Founders, operators, and builders — catch up on our full Startup Basics series (Legal, Finance, Growth & AI):

👉 thisweekinstartups.com/basics

Links from episode:

Check out Photoroom: https://www.photoroom.com/

Check out Google Cloud: https://cloud.google.com/

Follow Matt:

X: https://x.com/matthieurouif

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

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

Scaling AI Photo Editing to 300M Users with Photoroom’s Matt Rouif | AI Basics with Google Cloud

Today’s show:

We’re back with two insightful new TWiST founder interviews.

First up: Dean Leitersdorf of Decart tells us about squeezing maximum productivity out of your GPUs. But it’s not all talk: he also shows us the incredible open world model that can magically transform live footage.

THEN! Jason and Alex chat with Syncere AI founder Aaron Tan about Lume, his robotic lamp device that went viral for folding laundry. Hear why Aaron thinks the future of robotics is not necessarily humanoid, and all about his future plans for the Lume arms.

Timestamps:

(0:00) Alex introduces our TwiST 500 interviews

(02:27) TWiST 500 Interview #1: Dean Leitersdorf, CEO and Founder of Decart

(04:37) Setting out to build a “kilo-corn,” a trillion dollar company

(06:27) How making AI much faster opens up a world of new opportunities

(09:48) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠

(11:00) Why Dean thinks chatbots are the interface of the future

(17:24) How Decart builds and trains its models more efficiently (and for less money)

(20:01) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(21:14) Show Continues…

(24:36) Interview #2: Aaron Tan of Syncere AI

(25:13) Behind-the-scenes of that viral Lume “robot lamp folding laundry” video

(30:23) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.

(31:25) Moving beyond laundry: what else these Lume robots do?

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:

(09:48) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠

(20:01) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(30:23) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.

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

Decart makes AI faster, Lume teaches lamps to fold laundry | E2166

It’s a Friday TWiST and Jason and Alex are FIRED UP about this internal Meta doc laying out appropriate vs. inappropriate AI behavior… You won’t BELIEVE with what Zuck approves for 8-year-old users.

PLUS… AI job displacement is HERE, at least in the Big Apple… Jason’s getting kind of paranoid about the surveillance state… AI remains frothier than ever through new Cohere and Cognition rounds… and why we’re dubious that Sam Altman REALLY plans to spend $1 trillion on OpenAI data centers.

It’s all happening on a brand-new This Week in Startups. Give it a click!

Timestamps:

(0:00) Intro - How Opendoor became a meme stock

(06:58) When companies have less value than cash on hand… what gives?

(10:23) - (11:24) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist

(19:13) New York’s not adding jobs… Jason and Alex dig in and offer some theories.

(20:25) - (21:30) 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!

(26:56) AI job displacement is HERE and it’s happening, folks…

(30:05) Why Jason predicts unemployment will be 20% higher 1 year from today… add it to the TWiST Calendar

(30:24) - (31:37) 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

(33:02) Wait, Meta AI is having “sensual” chats with children? WHY?

(40:00) Will there be fallout to the Meta exposé? Legal? Staffing? Otherwise?

(47:47) AI remains frothier than ever with new Cohere and Cognition rounds.

(52:33) Sam Altman says he’s going to spend $1 trillion on data centers… Jason’s dubious.

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:

(10:23) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist

(20:25) 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!

(30:24) 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

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

Meta’s “Sensual” AI Doc LEAKS, Opendoor’s dreams became memes + OpenAI plans $1T data center spend | E2165

Today’s show:

We’re back with another all-star VC roundtable discussion.

Joining Jason are Dave McClure of Practical VC, NVNG’s Grady Buchanan, and Tomasz Tunguz of Theory VC. Together, they’re having a deep insider discussion of the state of venture, secondary markets, running funds of funds, the legacy of Lina Khan, the difficulty of recruiting, and why the pendulum has potentially swung in founders’ favor.

Timestamps

(0:00) INTRO, The origins of Practical VC and how secondary funds work.

(05:44) So… how does Dave decide what to BUY?

(09:27) Melanie - Companies are staying private longer… Is this good for fund managers?

(10:02) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(11:18) Show Continues…

(14:17) We’ve all heard about unicorns but… what about centaurs?!

(16:19) Jacob - Are VC marks… bullsh*t?! How long until your LPs should see DPI? The panel debates.

(17:22) Jacob - Is Jason too hard on Lina Khan? Dave says VCs created the problem!

(20:07) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits

(21:30) Show Continues…

(30:01) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.

(31:16) Show Continues…

(31:34) When it’s time to embed an expert into a struggling startup

(34:15) How investing in SO MANY COMPANIES gave Dave a trove of data

(40:33) Sometimes VCs have to be the “voice of reality”…

(45:53) Are stock buybacks the best use of capital?

(49:29) Jacob - The End of the ZIRP Era meets the Dawn of the AI Era

(51:04) Why running your business on debt, not equity, requires tough choices

(58:23) When you need to “take the medicine” on returns and live to fight another day.

(01:11:17) Is Grady actively seeking managers that have shown a demonstrated ability to produce liquidity?

(01:13:24) Dave says the pendulum has swung into founders’ favor.

(01:20:25) Dave teases his new secondary podcast, “Trading Places”!

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:

(10:02) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(20:07) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits

(30:01) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.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

The End of the ZIRP Era, and why recruiting is SO PAINFUL | E2164

Today’s show:

On an all-new Monday TWiST, Lon joins Jason and Alex to talk about a whole bunch of stories at the intersection of tech, business, and pop culture.

First up, is GPT Psychosis real? And if so, what are the warning signs that your loved ones have been ONESHOTTED.

Then, why did Jason get so upset at the NY Times piece about Mark Zuckerberg’s Palo Alto compound?

PLUS we’re discussing Trump’s export fees on AMD and Nvidia, Jason’s pitch for why the president should work more closely with Congress, a new tool in the search for rare-earth minerals, just how many self-driving trucks are on Chinese roads today, and much much more!

Timestamps:

(0:00) INTRO, Why Jason hated the NYT story about Mark Zuckerberg’s compound.

(09:54) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

(11:14) Show continues…

(19:54) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist

(21:01) Show continues…

(27:25) GPT Psychosis: Is it real and how widespread is it?

(29:13) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(30:16) Show continues…

(45:45) What it means to get “One-Shotted”: is Sam Altman doing this on purpose?

(53:56) Jason says working multiple jobs at once is STEALING… is that fair?

(01:04:53) Are Trump’s Chinese export fees for AMD and Nvidia a justified licensing process? Or a shakedown?

(01:09:22) Jason’s pitch for working closer with Congress, and why Alex has concerns about clarity

(01:12:02) PolyMarket: Will tariffs generate >$250b in 2025?

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:

(09:54) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

(19:54) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist

(29:13) Vanta - Get $1000 off your SOC 2 at https://www.vanta.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

GPT Psychosis is spreading, the NYT is Super-Doxxing Zuck, and Trump is wetting his beak on Chinese chip exports | E2163

Today’s show:

Jason and Lon recorded a Thursday night special edition, so no Alex this time, but still lots to talk about.

First up, Jason thinks it’s time for Tim Apple to exit the stage in lieu of a product obsessive innovator. Speaking of new products, GPT-5 is here and the hosts are… not exactly blown away. Are we in the midst of the AI trough of despair?

PLUS we’re talking Ripple’s acquisition of Rail, Donald Trump’s new AI chatbot, Bumble’s new direction, Airbnb’s potential paths forward and MUCH MUCH MORE.

Timestamps:

(0:00) Why Jason thinks Apple lacks innovation (plus a look back at his 2019 thoughts)

(08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(09:54) Show continues…

(20:10) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!

(21:18) Is GPT-5 coming for Lovable and Bolt?

(29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.com/Twist.

(30:55) Show continues…

(35:05) Ripple buying Rail, and why sometimes regulations are GOOD for companies

(43:28) Is Ripple about to become the MicroStrategy of XRP?

(47:48) Truth Social AI is perplexing, powered by Perplexity

(53:27) Should people be using ChatGPT for therapy? What do you think? How does that make you feel?

(01:04:42) Anthropic’s Dario Amodei recalls his greatest haters

(01:11:04) Bumble but… for friendship?

(01:12:20) DoorDash’s crazy growth, and the guys discuss who should buy Airbnb

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:

(08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(20:10) 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!

(29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.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

GPT-5 comes alive, Apple is struggling, and Ripple bought Rail | E2162

In the news segment, Jason reacts to the Tether CTO & General Counsel's interview on CNBC (2:22) and digs in to Netflix's latest earnings report (37:35).

Then, Vincent founder Slava Rubin joins to discuss all things alternative assets (44:26), his work founding Indiegogo, Launch’s investment, trading cards (1:17:19) & more.

Reacting to Tether’s CNBC interview, Netflix earnings + Vincent’s Slava Rubin on alt assets | E1250

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