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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:

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

Deel - http://deel.com/twist

LinkedIn Jobs - http://linkedIn.com/twist

Today’s show: 

Some pitches sound just like ads… and it’s a huge red flag for investors.

On our latest edition of TWiST Tokyo, Jason welcomes legendary angel investor (and long-time friend of the pod) Thomas McInerney. His list of investments reads like a Who’s Who of the tech elite, including Notion, SpaceX, Uber, OpenAI, Anthropic, and Perplexity….

At Founder University x Tokyo, they discuss how the angel investing landscape has shifted, why it’s so important for founders to stay humble, the reasons that investors need to stay not just optimistic but aggressively so, and what angels can add to companies beyond just writing checks.

Plus we revisit some classic TWiST clips featuring Thomas from over 10 years ago AND take a look at three of our favorite pitches from our Japanese founders.

Timestamps:

(00:00) FLASHBACK: Clips from Tom’s classic TWiST appearances

(02:54) Why Jason and Tom love hanging and building in Tokyo.

(05:30) How has the angel investing landscape changed over the last decade plus?

(09:38) “Being an investor is a commodity… You have to provide more than just money.”

(12:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(13:34) How Thomas evaluates very early stage startups

(14:56) Why Thomas invested in nuclear tech when it was hugely unpopular

(17:31) Why it’s so important for new founders to be both humble and smart

(18:50) The relevance and accuracy of Marc Andreessen’s “Idea Maze” metaphor

(20:40) Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit http://deel.com/twist to learn more.

(21:41) How Elon Musk brings oversized, visionary ideas to life

(26:11) Why founders using buzzwords is a huge red flag

(27:13) The little “poker tells” Thomas and Jason look for in a founder

(28:26) “If there’s any doubt, there’s no doubt.”

(30:47) LinkedIn Jobs - post your job for free at http://linkedIn.com/twist then promote it to get access to LinkedIn Jobs’ new AI assistant.

(32:04) PRO TIP: Don’t run out of money!

(38:10) The importance of being an aggressive optimist for investors

(43:27) The human brain cannot comprehend 1000x growth

(45:33) PITCH #1: Sakenomist is the cross-border commerce platform, starting with sake exporters (Hiroshi Takeuchi)

(51:47) PITCH #2: HomiiWorld, the IRL social app which helps you meet new people anywhere in the world

*

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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/

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Thank you to our partners:

(12:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist

(20:40) Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit http://deel.com/twist to learn more.

(30:47) LinkedIn Jobs - post your job for free at http://linkedIn.com/twist then promote it to get access to LinkedIn Jobs’ new AI assistant.

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

Avoiding buzzwords and marketing-speak (feat. Thomas McInerney) | E2236

This Week In Startups is made possible by:

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

LinkedIn Jobs - https://www.linkedin.com/twist

Zite - http://zite.com/twist

Today’s show: 

Why do 40% of Japanese students want to build a company rather than join the corporate workforce?

On TWiST, Jason considers this question along with special guest Kathy Matsui, general partner of the global VC fund MPower Partners.

Their wide-ranging discussion also features a look inside one of Jason’s favorite international companies, Japan’s own fashion retailer Uniqlo, where Kathy is a board member. (While in town, he took the opportunity to check out their flagship store in Ginza.)

They also take a look back at Japan’s economic crisis in the ‘90s, and why recovery took such a very long time… MPower’s philosophy while raising their second fund, and why they’re so focused on what they call “Japan Dynamism”… the key question of whether Japanese startups should focus on the domestic market first BEFORE chasing global customers… why an ESG (environment, social, governance) focus in Japan is so different from DEI in the US… and much more.

Timestamps:

(00:00) Kathy Matsui is on the board of one of Jason’s favorite companies, Uniqlo (and its parent, Fast Retailing)

(10:52) Why deflation in the ‘90s was “poison” for Japanese businesses and workers

(13:41) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit http://every.io/

(15:05) Why do American entrepreneurs keep falling in love with Japan?

(18:17) How the Japanese government is encouraging more founders to start tech companies

(20:05) LinkedIn Jobs - post your job for free at http://linkedIn.com/twist then promote it to get access to LinkedIn Jobs’ new AI assistant.

(21:15) Why more Japanese grads are becoming entrepreneurs

(23:46) What MPower means by “Japan Dynamism” and why they’re focused on it for Fund 2

(24:26) The various reasons so few female founders are getting funded in Japan

(27:38) The differences between MPower’s approach and corporate DEI in the US

(30:03) Zite - Zite is the fastest way to build business software with AI. Go to https:/zite.com/twist to get started.

(31:48) Is the “first Japan, then the WORLD” approach a waste?

(35:34) In Japan, you don’t build trust in just one meeting…

(39:19) Kathy’s take on the complex relationship between Japan and the MENA region

(42:13) Why the UAE and Saudi Arabia aren’t “dumb money,” as some in Silicon Valley assume

(43:49) Can Japan still rely on the United States as a strong geopolitical partner? There are question marks…

(48:16) Regarding China: “When you move up the stack… be careful what you wish for!”

(49:06) Q: Aladdin is developing smart trash cans… Kathy and Jason’s tips on founder Yuki Kanai’s pitch

(54:31) Q: Maya Hojnacki from AltSource Capital asks about how MPower helps startups facing regulatory or policy obstacles

(57:17) Q: Hiroki from Goi wants Jason and Kathy’s take on Japan’s point-based immigration policies

(1:06:38) Why Japan desperately needs AI to start taking more jobs

*

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

Thank you to our partners:

(13:41) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit http://every.io/

(20:05) LinkedIn Jobs - post your job for free at http://linkedIn.com/twist then promote it to get access to LinkedIn Jobs’ new AI assistant.

(30:03) Zite - Zite is the fastest way to build business software with AI. Go to https://zite.com/twist to get started.

Check out all our partner offers: https://partners.launch.co/

Japan’s Startup Revolution (feat. Kathy Matsui) | E2235

This Week In Startups is made possible by:

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

LumaAi - https://lumalabs.ai/twist

Squarespace - https://squarespace.com/twist

Today’s show: 

Government fraud and waste has become a prominent issue in the last month.

That’s what we are looking at.

On Today’s episode of TWiST, Jason interviews Alex Shieh of the The Antifraud Company.

Under the False Claims Act, enterprising Americans, like Alex, can receive up to 30% of fraud dollars they uncover! Jason digs into the business of fraud with Alex Shieh and how a generational company could be built around it!

PLUS Alex Wilhelm and Marcus Brotman take a look at the history of BOOM, $1.5 Billion dollar startup bringing back supersonic commercial travel!

Jason first interviewed Blake Scholl almost 10 years ago in 2016. Back then, BOOM was a dream to bringing back supersonic travel. The Concorde’s failure, and why BOOM is different, is central to Blake’s thinking. What is fascinating is Blake’s mindset and vision for the early stages of this future unicorn startup.

THEN, Jason answers live Q/A at Founder University Tokyo! In partnership with JETRO, Jason and the LAUNCH team are bringing Founder University to 35 Japanese startups over the next 9 weeks!

Timestamps:

(00:00) Why the Concorde failed and how BOOM Supersonic is bringing back faster than light travel

(08:34) The 30% efficiency rule for Mach 2 flights

(11:46) Netsuite - Get the free business guide Demystifying AI at https://www.netsuite.com/twist

(17:12) Building million dollar planes on a startup budget

(20:22) 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

(24:11) The Checklist Manifesto: Lessons for pilots and founders!

(26:02) How to build a team that can go supersonic

(32:49) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(33:55) Private Sector Doge: The Anti Fraud Company

(38:48) The $500B in Fraud uncovered

(48:34) How Alex Shieh’s team uses AI to hunt down fraud

(52:48) How you can win 30% of exposed fraud with the false claims Act

(56:27) Founder University Tokyo Q&A

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:

(11:46) Netsuite - Get the free business guide Demystifying AI at https://www.netsuite.com/twist

(20:22) 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

(32:49) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

Check out all our partner offers: https://partners.launch.co/

How to Make Billions from Exposing Fraud | E2234

This Week In Startups is made possible by:

Northwest Registered Agent - www.northwestregisteredagent.com/twist

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

Pipedrive - http://pipedrive.com/twist

Today’s show: 

TWiST is coming to you all from TOKYO as we launch Japan’s first-ever Founder University! That’s right, a full week of key insights from Japan’s top founders, investors, and tech visionaries… when we can pull ourselves away from our favorite izakaya spots, that is.

First up, Jason welcomes HyreSearch.com co-founder Sho Takei, a veteran of Uber and CloudKitchens who now helps startups recruit top talent from around the world.

Together they discuss the massive changes AI is bringing to every facet of the hiring process, Sho’s experiences working for infamously “super-pumped” Travis Kalanick, his tips for for establishing a corporate culture when hiring your first few employees, why being a co-founder is just a bit like getting married, and LOTS MORE.

Timestamps:

(00:00) We’re in TOKYO JAPAN for Founder University with Hyre co-founder (and Uber vet) Sho Takei.

(03:13) The challenges of early Uber recruiting in Asia

(05:22) Are Japanese workers motivated by stock-based compensation? Or is cash still king?

(08:24) Why tax rates give Singapore and Dubai a competitive advantage.

(09:17) Do in-person startups have an edge against entirely remote companies?

(11:50) How Jason thinks Hyre could grab their ultimate domain name…

(13:26) Northwest Registered Agent: Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at www.northwestregisteredagent.com/twist

(15:32) Just because a startup tactic works in the US… doesn’t mean it will work in Japan

(17:39) Travis Kalanick and Uber’s unique “super pumped” approach to recruiting

(20:01) It’s hard to fire someone in Japan! The high stakes for hiring mistakes.

(23:35) Sho’s tips for establishing a culture and hiring your first few employees (“hiring is guessing, and firing is knowing”)

(25:33) Why being a co-founder is kind of like getting married

(27:46) 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.

(28:59) How AI is revolutionizing the hiring process, and why you still need a human in the loop

(34:02) How do you win over amazing talent that’s already happy at another company

(39:47) Pipedrive: Bring your entire sales process into one elegant space. Get started with a 30 day free trial at http://pipedrive.com/twist

(43:19) How Hyre operates as an agency and also an in-house recruiter

(44:57) The surprising importance of “candidate experience” when hiring in Japan

*

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:

(13:26) Northwest Registered Agent: Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at www.northwestregisteredagent.com/twist

(27:46) 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.

(39:47) Pipedrive: Bring your entire sales process into one elegant space. Get started with a 30 day free trial at http://pipedrive.com/twist

Secrets of Startup Recruiting in the US AND Japan! (feat. Sho Takei) | E2233

This Week In Startups is made possible by:

Hubspot - http://clickhubspot.com/twist1

Circle.so - http://circle.so/twist

Sentry - http://sentry.io/twist

Today’s show: 

On the last TWiST episode before Jason goes to Japan and Alex begins on paternity leave, the hosts break down the blockbuster tech news that is kicking off 2026.

Discord AND Strava both eyeing billion dollar IPOs, two massive social media apps with millions of daily active users. Jason unpacks Discord’s the growth story, from a gaming-first product launch in 2015, to a community/work platform and social media for all. Jason explains why Strava proves that data is the MOAT for consumer apps.

PLUS Jason and Alex are joined by Producer Oliver to rank the top CES products. Jason gave his thoughts on the different robots, self driving cars, and multi-fold phones on display.

Would you buy a triple-fold phone?

Timestamps:

(00:00) Discord looks to go public at $7 Billion!

(10:05) Hubspot: Check out the guide “How to Get Your First 100 Customers.” Download it for free at http://clickhubspot.com/twist1

(13:37) Strava going public and why data IS the moat for consumer software

(19:28) Circle.so: the easiest way to build a home for your community, events, and courses — all under your own brand.

(22:25) Anthropic’s $350B valuation and why it makes sense

(31:59) Sentry: New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST

(33:05) Why is China upset about META’s Manus acquisition — and why Jason is hopeful for the US-China relationship

(37:24) Jason’s favorite part of CES: The rise of open source AI!

(40:59) Why Jason LOVES his self driving Tesla — why public companies need to be safe and not push too quickly

(44:24) Producer Oliver’s Top CES Tech products

(54:46) Jason’s Major Takeway from CES

(59:43) How many times can you fold a phone?

(1:04:04) New interfaces for smartphones

*

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

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

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

*

Follow Lon:

X: https://x.com/lons

*

Follow Alex:

X: https://x.com/alex

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

*

Follow Jason:

X: https://twitter.com/Jason

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

*

Thank you to our partners:

(10:05) Hubspot: Check out the guide “How to Get Your First 100 Customers.” Download it for free at http://clickhubspot.com/twist1

(19:28) Circle.so: the easiest way to build a home for your community, events, and courses — all under your own brand.

(31:59) Sentry: New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code 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

Jason’s Top CES Products and Takeaways | E2232

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

*

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

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

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

*

Follow Lon:

X: https://x.com/lons

*

Follow Alex:

X: https://x.com/alex

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

*

Follow Jason:

X: https://twitter.com/Jason

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

*

Thank you to our partners:

(10:12) 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! 

*

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

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

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

*

Follow Lon:

X: https://x.com/lons

*

Follow Alex:

X: https://x.com/alex

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

*

Follow Jason:

X: https://twitter.com/Jason

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

*

Thank you to our partners:

(9:48) 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

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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

*

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

*

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/

*

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

*

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

(0:00) Jason Kicks off the show

(2:49) Brad Feld, Co-founder of Foundry, talks about starting out in investing

(13:30) LinkedIn Jobs - Post your first job for free at https://linkedin.com/angel 

(14:56) Brad’s thesis for whom he’ll get in the “trenches” with

(20:48) MasterClass - Get 15% off an annual membership at https://masterclass.com/startups

(22:22) Fighting to the end + Investing through the dot-com bubble

(38:13) Microsoft for Startups Founders Hub - Apply in 5 minutes, no funding required, sign up at http://aka.ms/thisweekinstartups

(39:43) Surviving the GFC

(44:23) Brad’s perspective on the investor/CEO dynamic + being a leader in a down market

(1:00:02) Reflecting on the speculative asset bubble

(1:16:44) Looking forward into 2023

FOLLOW Brad: https://linktr.ee/bfeld

FOLLOW Jason: https://linktr.ee/calacanis

FOLLOW Molly: https://twitter.com/mollywood

ANGEL: Brad Feld on investing through 3 economic cycles, CEO/investor dynamics, and more | E1660

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