This Week in Startups

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Orchestrating Smarter AI Systems with AI21 Labs' Yoav Shoham | AI Basics with Google Cloud Jul 10, 2025

Show notes

In this episode of AI Basics, Jason sits down with Yoav Shoham — Stanford professor emeritus and co-founder of AI21 Labs, creators of Jurassic-2, Wordtune, and the new orchestration system Maestro.

They unpack:

Why enterprise AI struggles with reliability
What orchestration really means (and why LLMs alone aren't enough)
The pitfalls of "agent-washing"
Small vs large models, agent-to-agent protocols, and where real opportunities lie

This one is for founders building with AI — if you're navigating hallucinations, chasing automation, or exploring multi-agent workflows, this episode is a must.

Timestamps:

(0:00) Yoav Shoham joins Jason to discuss AI Basics.

(1:05) What AI21 Labs is building — from Jurassic-2 to Maestro

(5:49) The overuse and confusion of the seductive term "agent"

(8:22) Small models vs large models: what's best for enterprise?

(10:53) The verticalization of AI: legal, accounting, and beyond

(12:17) The challenge of agent-to-agent communication and shared semantics

(17:08) What's overhyped vs underhyped in AI — Yoav's advice for founders

Uncover more valuable insights from AI leaders in Google Cloud's 'Future of AI: Perspectives for Startups' report.

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 episde:

Google Cloud — Build smarter with AI tools built for startups
AI21 Labs — Makers of Wordtune, Jurassic-2, and Maestro
Maestro — Orchestrate AI agents and tools across workflows
Jamba — AI21's hybrid language model with breakthrough efficiency

Learn About Google's A2A (Agent-to-Agent) Protocol

The next evolution in agent interoperability and coordination:

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Starlink + Tesla? $4T Nvidia? Perplexity Browser? Linda Yaccarino Steps Down? | E2149 Jul 09, 2025

Show notes

On a brand new TWiST, Jason and Alex ponder… What if every Tesla doubled as a Starlink-powered Wi-Fi hotspot? Plus, Nvidia's historic $4T valuation, Perplexity's fancy new AI browser that literally books flights, Linda Yaccarino steps down as X CEO, Waymo launches teen accounts, and maybe recording everything all the time has some disadvantages? Later, Tim Ranzetta joins to explain how his nonprofit is making personal finance mandatory in high schools. A must-watch for founders, investors, and anyone navigating the future of tech.

Timestamps:

(03:04) Linda Y is out at X but it's NOT because of Grok's Hitler moment

(09:59) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(13:23) Nvidia is worth more than any other company EVER?

(17:40) Granola's charging individuals MORE than business accounts? But why?

(20:42) INBOUND - Use code TWIST10 for 10% off your General Admission ticket at https://www.inbound.com/register. (Valid thru 7/31)

(23:39) Jason thinks the AI recording and transcript lawsuits will begin by next year…

(24:05) Perplexity launches the Comet browser: we're checking how it compares with Dia and other rivals!

(30:07) 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.

(34:09) Waymo is expanding… Why there's no shame in the robotaxi game…

(41:28) Robinhood is tokenizing US equities for EU investors… we unpack what it all means and how it works.

(49:18) Tim Ranzetta of Next Gen Personal Finance tells us what we don't teach kids about finance and what they most need to know

(01:29:25) Why finance and investing is all about psychology, and how to "think in bets"

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Thank you to our partners:

(09:59) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(20:42) INBOUND - Use code TWIST10 for 10% off your General Admission ticket at https://www.inbound.com/register. (Valid thru 7/31)

(30:07) 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.

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

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Cloud Seeding, Conspiracies & the Texas Floods | BONUS EPISODE! Jul 09, 2025

Show notes

Today's show:

Cloud seeding startup Rainmaker faced a viral backlash after deadly floods in Texas—so @Jason hosted an emergency X Spaces with founder Augustus Doricko to unpack what really happened. Did Rainmaker cause the floods? How much water can cloud seeding actually produce? Is it safe, and should we even be doing it? They dive into the science, conspiracy theories, regulation, and how cloud seeding compares to desalination as a tool to fight drought and preserve ecosystems. A fascinating, good-faith convo on the future of climate tech.

Timestamps:

(0:00) Cloud seeding controversy and its impact on Texas floods(2:24) Background and impact of the Texas flooding event(8:05) Comparing cloud seeding to other environmental solutions(10:20) Discussing population, water distribution, and environmental restoration(14:22) Cloud seeding timeline, feasibility, and solar panels on water canals(17:17) Ethics, concerns, and regulatory framework for cloud seeding(24:07) Public safety, ethical considerations, and social media interactions regarding cloud seeding(26:00) Closing remarks and future collaboration

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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

Check out Jason's suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

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

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Exits Are Back, QSB Stock & The New America Party? | E2148 Jul 07, 2025

Show notes

Today's show:

Startup exits are heating up with $67.7B in Q2 activity, QSBS just got a major expansion, and Robinhood is pushing boundaries with tokenized SPVs. In this episode, @Jason and @alex break down what it all means for founders and investors, plus the rise of Elon's "America Party," TikTok's potential reboot, and why SaaS startups must rebrand around AI to stay competitive. A must-watch for anyone building, investing, or navigating tech in 2025.

Timestamps:

(04:29) Jason's thoughts on Elon Musk's America Party

(10:05) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist

(15:02) M&A keeps heating up and why a big fintech IPO could be on the way!

(20:00) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠

(26:32) Unpacking liquidation preferences for non-experts

(29:11) AI companies are soaking up the majority of investment dollars but what does that really MEAN?

(30:02) MonarchMoney - Get 50% off your first year by going to MonarchMoney.com and using the offer code TWiST

(36:26) Why Jason's group chat will love the QSBS expansion but it's not really that big of a deal…

(46:27) TikTok seems poised to make a deal… Why Jason thinks they do pose a national security threat.

(59:22) Why is CoreWeave picking up Core Scientific, and is now a good time to sell your shares?

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Thank you to our partners:

(10:05) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist

(20:00) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠

(30:02) MonarchMoney - Get 50% off your first year by going to MonarchMoney.com and using the offer code 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

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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Startup Valuations, Biotech's Crunch & AI's Massive TAM | E2147 Jul 02, 2025

Show notes

Today's show:

It's another blockbuster panel of insiders, as Alex sits down with Astasia Myers from Felicis, Matt Turck from First Mark Capital, and D.A. Wallach of Time BioVentures. AI is reshaping early-stage investing, with startups raising record-setting rounds adn chasing $100B+ markets. Meanwhile, biotech faces a "Great Depression" as public markets stay shut, putting added pressure on private capital. In healthcare, AI-powered virtual doctors promise to bring world-class medical advice to everyone, while fertility tech could revolutionize IVF by automating embryo handling and slashing costs. Hear our VC experts exclusive thoughts on these trends and much more!

Timestamps:

(2:21) The post-Q2 landscape and everyone's immediate reactions

(05:00) Why biotech is in a "Great Depression," even for AI companies!

(9:36) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(12:14) Overpriced vs. high-performing: Do high prices ALWAYS mean low expected returns and vice versa?

(14:50) Mega markets: how AI is different from past software shifts(18:58) Everyone's companies are CRUSHING IT: why genAI has crazy tailwinds right now

(20:33) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(21:46) Product-market fit and revenue durability in AI(24:29) Marketing and community development for early stage founders(25:14) AI advancements in humor, avatars, and healthcare(29:30) 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.(30:45) Healthcare innovation and AI foundation models(35:37) AI differentiation, OpenAI valuation, and infrastructure companies(43:08) User experience in LLMs and AI inference costs(51:21) AI healthcare applications and founding team trends(56:28) Hiring trends, burn rates, and outsourcing in biotech(1:01:51) Government investment in biotech and the European AI ecosystem(1:06:43) Academic founders and the Felicis Fellows program(1:09:10) Recent exits and the outlook for the upcoming quarters(1:12:27) Innovations in fertility treatments and prenatal testing(1:15:51) Summary of bullish trends and future outlook(1:16:14) Closing remarks and future check-in plans

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Thank you to our partners:

(9:36) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech

(20:33) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(29:30) 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

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The Grammarly–Superhuman Megadeal, plus TWiST 500 chats with LabelBox and Apptronik's founders | E2146 Jul 01, 2025

Show notes

Today's show:

Grammarly is acquiring the beloved email app Superhuman! In today's extremely timely episode, @alex sits down with Grammarly CEO Shishir Mehrotra and Superhuman founder Rahul Vohra to unpack why they're merging, how they plan to combine apps and AI agents, and what it means for the future of email and work. PLUS they reveal how Grammarly's 40M+ daily users already rely on email—and why this deal is the key to building the ultimate communication assistant. Don't miss this deep dive into one of the most exciting AI acquisitions yet!

#AI #Startups #Productivity #Grammarly #Superhuman #VentureCapital #MergersAndAcquisitions

Timestamps:

(0:00) Introduction to the future of robotics and AI regulation(1:11) Introduction of hosts and overview of today's topics(4:19) Cloudflare's new pay per crawl product

(09:37) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(10:41) Polymarket segment on Apple's acquisition prospects(14:29) Grammarly and Superhuman CEOs interviews

(19:42) Retool - Visit https://www.retool.com/twist and try it out today.(24:09) AI in productivity tools and email agents discussion(29:23) 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(30:46) Grammarly's AI platform and the acquisition of Superhuman(41:16) Introduction of Manu Sharma from Labelbox(41:47) The role of data labeling in AI and Labelbox's data factory(53:44) Labelbox's market position and capital efficiency post-ChatGPT(1:03:00) Advances in humanoid robotics with Jeff Cardenas from Apptronik(1:07:09) Market readiness and capabilities of Apollo 2 robots(1:13:27) Humanoid robotics: Google DeepMind partnership and international competition(1:20:54) US federal support for R&D in robotics(1:22:10) The evolution of humanoid robotics and Apptronik's growth in Austin

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Thank you to our partners:

(19:42) Retool - Visit https://www.retool.com/twist and try it out today.

(29:23) 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:

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

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Rebuilding Civilization from First Principles: Inside Balaji's Network State Vision | E2145 Jun 30, 2025

Show notes

Today's show: Jason sits down with Balaji Srinivasan in Singapore to explore how he's turning years of theory into reality with Network School—the first node of a broader vision for internet-native, decentralized societies. Balaji explains how these "sharp societies" combine education, co-living, and startup culture to create physical communities aligned by values, not geography. From digital nomads to aspiring founders, people are opting into these new systems as an alternative to broken traditional governance. They discuss everything from Starbase and sovereignty to the future of democracy, Bitcoin, and America's place in a multipolar world.

Timestamps:

(0:00) Introduction of Balaji Srinivasan and the impact of Bitcoin(1:39) The concept of Network School and Network State, including startup societies(4:05) Benefits and historical context of network effects in communities(7:08) Economic and social benefits of Network School(9:35) Global appeal and diverse motivations of Network School participants

(10:22) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(12:30) Media perspectives on new societies and the challenge of self-determination

(19:35) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(24:00) Personal experiences with US state migration and critique of California politics(27:11) The right to exit, thousand city system, and the two-party system

(29:44) Vouched - Trust for agents that's built for builders like you. Check it out at http://vouched.id/twist(31:09) Choosing a country like choosing a college and impressions of new cities(34:03) America's global reputation, politics, and the decline of empires(39:25) Dollar devaluation, Bitcoin's future, and global currency dynamics(41:26) Global power struggles: China versus the Internet and US demographics(44:01) Trump's tariffs, MAGA, and international trade realities(48:12) China's manufacturing dominance and US diplomatic legacy(54:39) The Internet's counterbalance to China and Bitcoin's future risks(1:00:31) Role of cryptocurrencies, quantum computing, and Bitcoin security(1:02:12) Cryptocurrency challenges and the resilience of Bitcoin(1:03:27) Network school state community and opportunities for investors(1:04:01) Closing remarks and final pitch for Network School

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

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Follow Lon:

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

Thank you to our partners:

(10:22) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(19:35) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(29:44) Vouched - Trust for agents that's built for builders like you. Check it out at http://vouched.id/twist(0:00)

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:

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

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Travis' Uber Comeback, AGI's Stakes, Meta's $100M AI Hires & Prediction Market Gold Rush | E2144 Jun 27, 2025

Show notes

Today's show:

EVs are igniting a global tariff war, and Xiaomi's shockingly cheap, high-quality electric cars threaten to obliterate Western automakers, sparking fears of a manufacturing wipeout. In today's brand-new TWiST, Jason and Alex dive into the EV price war, Uber's rumored plan to team up with Travis Kalanick on a self-driving takeover, and DoorDash's mega-drones giving us a glimpse of the future of food delivery. Plus, Tesla's cautious safety driver rollout shows we're only in the early innings of the autonomous revolution, a consideration of Meta's talent shopping spree, AND a new edition of Reddit Rapid Response. Don't miss this deep dive into the future of cars, delivery, and AI.

Timestamps:

(02:24) Guess who's BACK at Uber? On the Travis Kalahnik-Pony AI deal.

(10:43) Superpower - Visit superpower.com/twist to get $50 off your membership. This offer is only for the first 100 twist listeners who sign up.

(17:24) All the huge opportunities for Kalshi, PolyMarket and prediction markets

(19:44) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(25:37) TODAY'S POLYMARKET: How well will Apple's "F1" do at the box office?

(30:03) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

(31:58)What actually IS AGI? And why does it matter for the Microsoft-OpenAI negotiation?

(45:57) Inside Meta's massive Superintelligence shopping spree: maybe it's not so crazy to pay AI experts $100M?

(01:05:15) Reddit Rapid Response: Can you be a great founder if you hate doing cold sales?

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:

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Follow Jason:

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

Thank you to our partners:

(10:43) Superpower - Visit superpower.com/twist to get $50 off your membership. This offer is only for the first 100 twist listeners who sign up.

(19:44) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(30:03) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.

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:

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