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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:

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

Today’s show:

It’s a brand-new PACKED episode of TWiST. Jason and Alex welcome guest Zach Dive of Adam.new, to tell us why he made a deepfake AI ad starring Jason and the All-In besties.

PLUS a rundown of the biggest tech and startup news of the day, including Disney’s decision to sunset Hulu, OpenAI’s new open-weight models, the Cloudflare vs. Perplexity feud, Uber’s newly-announced stock buyback, China’s Luckin Coffee coming to Manhattan, and much much more!

Timestamps:

(0:00) Luckin Coffee hits NYC… along with COMMUNISM?!

(09:15) Is China taking on major American brands on PURPOSE?

(10:16) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(11:29) Show Continues…

(20:17) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech

(21:30) Show Continues…

(26:02) RIP HULU: Why Disney is sunsetting the iconic app.

(28:37) Nostracanis Returns: Jason’s 2017 Disney vs. Netflix predictions came true

(30:24) .TECH - Say it without saying it. Head to www.get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.

(31:28) Show Continues…

(35:39) Zach Dive of Adam.new joins to tell us about making a viral deepfake ad starring JCal and the Besties

(44:10) Zach shares thoughts on AI and copyright, and why it’s a problem for the “big dogs,” not him… yet

(48:12) Jason wants to wet his beak… but is there room in the Adam.new seed round?

(53:07)OpenAI’s new models are open-WEIGHT; how that’s different from open-source.

(58:36) Do Nvidia and Apple devices NEED kill switches and backdoors? Why it’s such a tough question.

(01:02:10) GPT-5 arrives TOMORROW?!

(01:03:31) Cloudflare vs. Perplexity… let them fight?

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:

(10:16) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(20:17) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech

(30:24) .TECH - Say it without saying it. Head to www.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

Communist coffee hits NYC, RIP Hulu, GPT-5 arrives and more | E2161

Today’s show:

Jason and Alex are running down the biggest tech, startup, and business stories of the day on a brand-new Monday TWIST.Which countries are leading the AI race, based on academic papers? Why Jason thinks covert agencies are spying on Meta’s superintelligence team. Lina Khan’s taking a victory lap on the Figma IPO but what did she REALLY accomplish during her Biden administration tenure? PLUS, why we’re bringing Founder University to the MENA region.

All that and MORE on a packed episode! Find out why we’re the #1 podcast for startups and founders.

Timestamps:

(0:00) Why Jason is attending more TV poker tournaments

(4:02) Did you know Founder University is headed to MENA? Calling all Riyadh founders.

(10:01) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(11:27) Show Continues…

(19:52) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist⁠⁠⁠

(21:01) Why Jason doesn’t think Lina Khan deserves her Figma IPO victory lap.

(23:17) Jason thinks Figma is overpriced: how quickly could a rival build a competitor?

(27:53) For an investor, there’s a huge difference between a home run and a GRAND SLAM.

(30:42) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST

(31:55) Show Continues…

(40:59) Why Jason thinks covert agencies are spying on Meta’s global Superintelligence Team…

(50:43) Which countries are leading the AI race in terms of research? Producer Claude helps with the answer.

(57:12) Fact-checking the viral BYD TikTok: can their self-driving cars really drive themselves off the ship?

(59:52) Jason and Alex check out some of their dream cars

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

(19:52) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist⁠⁠⁠

(30:42) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.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

Lina Khan’s Figma victory lap, Meta’s Superintelligence Team, BYD mega car-carrier video & MORE | E2160

Today’s show:

Alex is back with three more awesome interviews with founders on the bleeding edge of innovative tech.

 • Dr. Hon Weng Chong walks us through the basics of biological computing and Cortical Labs’ first-ever commercial computer running on living human cells.
 • Turing founder Jonathan Siddarth unpacks the secrets of LLM benchmarking, and explains why even our most advanced tests need to get much much harder right away.
 • Finally, Mercor founder Brendan Foody on how AI is about to reinvent the hiring process, and marrying the effectiveness of recruiters with the ease of online job boards.

It’s three — count ’em, three — can’t miss TWiST interviews guaranteed to make you smarter

Timestamps:

(0:00) OpenAI’s GPT-5: When is it coming out? Is it going to be TOO smart?

(08:06) Cortical Labs’ Hon Weng Chong on the electric connection between neuroscience and machine learning

(10:20) 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!

(11:27) Show Continues…

(15:17) The extreme difficulty of going from the lab to a shippable product

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

(21:05) Show Continues…

(28:15) Why data is a factor of time

(29:52) 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

(31:16) Show Continues…

(42:44) Turing CEO Jonathan Siddarth explains why it’s so important to keep benchmarking our LLMs

(47:24) What it means when a model “saturates” a test, and why benchmarks need to get HARDER

(50:22) What happens with the LLMs can answer all of our smartest questions?

(53:44) AI Agents train in gyms? Wait, really?

(01:01:33) Coding teaches models how to think, and more training mysteries don’t understand

(01:03:11) Brendan Foody from Mercor explains the “matching problem” that makes hiring such a pain

(01:07:02) How Mercor combines a job board’s distribution with the value of a recruitment agency

(01:10:49) Brendan recalls building his first AI interviewer in his college dorm

(01:20:16) Mercor has the opposite of a retention problem and crazy growth

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:

(10:20) 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!

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

(29:52) 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

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

TWiST 500 interviews with Cortical Labs, Turing, AND Mercor | E2159

Today’s show:

It’s another All Star Investor Panel! Jason and Alex welcome TrustFund VC founder Sophia Amoruso AND WeekendFund investor/Product Hunt founder Ryan Hoover.Together they’re going DEEP on the current environment for startups, founders, and investors. How do tell durable from brittle revenue… Everyone’s different approaches to follow-on investments and recycling… Strategies on when to trim a position… The benefits of hosting co-working events and jam sessions… And LOTS LOTS more!

It’s an essential watch for anyone building or investing in companies in 2025!

Timestamps:

(0:00) Introducing our amazing investor panel!

(03:15) The panel shares their First Fund experiences

(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(11:27) Show cont…

(12:46) Where we’re at on the investor Greed-Fear Index

(13:54) The delicate art of investor discipline

(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(21:59) Sophia’s criteria for a follow-on investment

(24:17) Founders are going direct on social media

(29:35) 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.

(30:49) Show cont…

(32:33) Why we’re seeing so many more Series Bs

(33:30) So when do you trim a position?

(39:35) There are SO MANY COMPANIES! Why surface area matters.

(43:25) Durable vs. brittle revenue and how to tell them apart

(46:15) When it’s time to angel invest outside your fund

(49:04) The panel’s approaches to capital recycling

(57:15) The benefits of co-working “jam sessions”

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:

(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(29:35) 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.

DISCLAIMER

*All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.Rate as of 7/18/25. APY is variable and subject to change.

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

All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158

Today’s show:

SYDNEY SWEENEY’S AMERICAN EAGLE AD DIVIDES OUR PANEL!PLUS WHAT STARTUPS CAN LEARN FROM THE VIRAL ASTRONOMER RESPONSEJason, Alex, and Lon are looking at some of the biggest media stories of the day before returning to their favorite topic, tech. Tune in for deep dives on IMAX’s new AI film festival, Figma’s big IPO and much more!

*

Timestamps:

(0:00) Jason and Alex kick off the show!

(3:45) Lon’s joining Alex and Lon to discuss the controversial Sydney Sweeney genes/jeans ad

(7:20) A look at the polarizing takes on this jeans ad.

(10:10) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠

(11:46) Hear the verdict from Jason, self—proclaimed Chairman of the Interwebs

(16:42) Alex points out the economic impact of the controversy

(20:26) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(21:25) Back to the show!

(26:35) Paltrow’s Astronomer ad, meme-processing and the ideal way to change the conversation

(30:04) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

(31:28) Back to the show!

(36:48) Netflix and the growing controversy around AI’s role in filmmaking

(42:53) IMAX/Runway collaboration and Hollywood’s shifting attitude toward AI

(47:34) Everything that went wrong with the Tea App

(54:27) Why Jason thinks app stores should ban “anonymous” forms and message boards

(1:04:19) Figma upped its IPO price… what does it mean for the return of liquidity? And is this too high or fairly priced?

(1:07:53) Paul Graham says you shouldn’t drop out of college to work on a startup… Why Thiel Fellows disagree

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Thank you to our partners:

(10:10) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠

(20:26) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(30:04) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist

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

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Substack: https://twistartups.substack.com

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Figma IPO, IMAX AI Festival, the Tea app spill, that one Sydney Sweeney jeans ad, and more! | E2157

Today’s show:

Jason’s back and filling us in on his experiences in Washington DC, at the All-In AI Summit, including getting a Trump shoutout from stage, debating immigration with VP Vance, and calling out Sec. Wright for dismissing solar power.THEN Jason and Alex talk about the immense promise of open-source robotics and check out Hugging Face’s Reachy…PLUS picking apart the White House’s new AI-related executive orders, why Jason is afraid of China repeating its Huawei success, a free exchange about tariffs vs. free trade, AND a pressing query from a founder on Reddit: how bad is it to add AI to your product too early?

Timestamps:

(0:00) INTRO, Alex updates Jason about all this week’s TWiST 500 interviews

(03:33) Inside Jason’s experiences at this week’s All In AI Summit with POTUS!

(05:33) Jason’s back and forth on solar power with US Energy Sec. Chris Wright

(09:56) Inbound - Use code TWIST10 for 10% off your General Admission ticket at [https://www.inbound.com/register](https://www.inbound.com/register.) (Valid thru 7/31)

(11:02) Promo end

(16:54) Jason asks AMD CEO Lisa Su about reaching “superintelligence” and whether it could trigger an unemployment crisis

(19:51) 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.

(20:44) Promo end

(23:42) Jason says… any time you have to wait days or weeks for a service or product, there’s a MASSIVE opportunity.

(26:16) What do Trump’s new AI executive orders actually say?

(27:27) Which EO’s are red meat for Trump’s base, and which ones are likely to become laws and have real impact?

(29:50) 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 https://public.com/twist.

(31:05) Promo end

(35:17) How Huawei went worldwide and why Jason doesn’t want that to happen again with AI.

(38:32) Jason and Alex have a little tariff vs. free trade debate.

(47:03) VP Vance complained about US tech companies laying off Americans, then hiring immigrants; Jason gives his take

(53:35) Jason answers a Reddit question: Is adding AI to your product too early a TRAP?

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

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

Thank you to our partners:

(09:56) Inbound - Use code TWIST10 for 10% off your General Admission ticket at [https://www.inbound.com/register](https://www.inbound.com/register.) (Valid thru 7/31)

(19:51) 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.

(29:50) 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 https://public.com/twist.

*Disclaimer:All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.Rate as of 7/18/25. APY is variable and subject to change.

Behind the scenes at the ALL-IN AI SUMMIT w/ POTUS, JD Vance, Jensen Huang, Lisa Su, and more… | E2156

Today’s show:

TWiST is back with a three more hugely insightful (and also fun!) founder interviews.

First up, Trey Holterman from Tennr tells us why getting in to see a specialist is so time consuming, and how AI is making the entire health care industry more streamlined.THEN Gill Verdon from Extropic AI unpacks deterministic vs. probabilistic computing, and how thermodynamics can make everything from robots to VR more effective.FINALLY, Tyler Denk from our fav newsletter platform Beehiiv walks us through their future roadmap, and explains why they’re adding new features SO OFTEN.It’s a packed episode full of fresh insights for founders. Check it out!

Timestamps:

(0:00) Alex opens the show with the venture/investor POV on TWiST 500 med tech company Tennr

(03:38) Tennr CEO/co-founder Trey Holterman on the inefficiencies facing medical specialists and why patients are actually “leads”

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

(11:44) Paid Promo END

(14:05) How Tennr trained an AI model to comb through clinical histories, medical files, and doctor’s notes

(18:19) Why automation matters for Tennr but it’s not the WHOLE story

(20:03) 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!

(21:10) Paid Promo END

(22:57) The incredible cultural influence of the Dominos Pizza Tracker

(29:57) 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

(31:20) Gill Verdon from Extropic on the difficulty of keeping up with the demand for compute and the “scaling law”

(35:37) Thermodynamic regimes, the differences between deterministic vs. probabilistic computing, and why this matters

(41:31) Gill on expanding Extropic’s research team while keeping a close eye on burn

(52:17) Will robots ever be FULLY autonomous, with no ties or connections back to the fleet? Gill says… maybe!

(58:52) Beehiiv’s Tyler Denk on hitting $20M ARR while ALSO scaling up their ad network

(01:00:35) The practical and psychological importance of product velocity and shipping as many features as possible

(01:01:57) Why Tyler says “Substack vs. Beehiiv” is analogous to “Amazon vs. Shopify”

(01:08:08) How much larger can the newsletter market still GROW? (And the promise of moving beyond content and into marketing emails.)

(01:09:00) Why Tyler thinks the strongest publishers own their audience and distribution

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:

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

(20:03) 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!

(29:57) 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

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

AUTOMATING HEALTH CARE, THERMODYNAMIC COMPUTING, AND PRODUCT VELOCITY | E2155

First, Jason covers OZY media's attempted deception of Goldman Sachs & investors (1:50), then covers Clubhouse's monetization problem with special guest Ashley Carman from the Verge (24:26). To wrap up, he discusses VC retirements (46:30) and Disney's Star Wars Visions (56:29).

OZY Media’s deception, VC retirement, Clubhouse’s monetization problem with The Verge’s Ashley Carman & more | E1292

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