Clawdbot is an inflection point in AI history | E2240

Jason is back from Davos and Tokyo! We are jumping right back in with a group of Clawdbot power users: Alex Finn, Matt Von Horn, and Dan Penguine. Clawdbot is a hot open source AI project that lets users automate… everything! Dan helped his automate his aging parent’s tea shop, Matt built news sourcing bots, and Alex runs his one-man SAAS startup with Clawdbot as an AI employee! But with all of that power comes the responsibility of making sure you are not giving your AI too many authorizations that could come under fire! Whether fisching emails, “injections”, or bad decision making from incorrect information online. Check out how these 3 experts, Jason and Alex are thinking about the bleeding edge of AI!

From Blood Transfusions to Burritos, How Zipline is Automating Delivery | E2238

On today’s TWIST episode, Alex interviews two of the top startup co-founders: Keller Cliffton of Zipline and Anastasis Germanidis of Runway. Zipline announced its $600 million raise at a $7.6 BILLION valuation. Kellers breaks down the origins, economics, and future of Zipline’s contrarian bet in drone delivery. What was science fiction a decade ago is now a regular part of life for many. In fact, Zipline operates more flights than United! Zipline is set to leapfrog the car delivery apps AND self driving cars with the superior economics of drone delivery. It is much cheaper to transport your burrito in a lightweight drone than a 6,000 pound self driving car! Then, Alex is joined by Anastasis Germanidis, the CTO and co-founder of Runway, to explain why the next frontier of generative AI is world models!

How startups suddenly became “cool” in Japan (feat. Shin Takamiya of Globis Capital) | E2237

Not long ago, promising young Japanese graduates wanted to go work for the largest, most established, and even oldest corporations: Sony, Mitsubishi, and the like. But now, just over the last few years, more and more Japanese people are becoming entrepreneurs and founders. TWiST Japan continues with a fascinating look inside the country’s growing startup ecosystem with special guest, venture capitalist Shinichi “Shin” Takamiya. He’ll walk Jason through how Japan stayed ahead of the rest of the world in technology, but started falling behind when it came to founding companies, and how the Japanese are now starting to level the playing field. PLUS why his fund, Globis, sees other VC firms as collaborators rather than the competition… How AI is helping Japanese and America founders build their companies more quickly…

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

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.

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

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.

How to Make Billions from Exposing Fraud | E2234

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.

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

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](http://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.

Jason’s Top CES Products and Takeaways | E2232

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?

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

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.

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

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 returns and investment considerations 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.

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

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!

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

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.

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

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!

Level up your copywriting w/ Sam Parr | E2226

DID YOU KNOW… most of the tried and true techniques devised by marketing gurus in the ‘40s and ‘50s still apply today? On TWiST, we’re joined by online marketing expert Sam Parr, host of “My First Million” and founder of Hampton. He’s sharing all of his top tips and tricks for making your writing more compelling, and converting your readers into new customers. In this essential pod for any and all founders, hear Jason and Sam run down their list of the best-ever marketing books, why there’s no such this as “too long” only “too uninteresting,” when to use AI and when to rely on your own brain, why you’re the average of your five best friends, and lots more deep insights.

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

How do top tech CEOs hire? AI has thrown out the playbook for getting hired — so what are the most innovative firms looking for? Anyone can learn any skill and automate much of it, what is to be valued in the modern labor market? On our first AI Roundtable episode of TWiST, Jason is joined by three top tech CEOs: Wade Foster (Zapier), Mikey Schulman (Suno), and Ali Ansari (Micro1). They each give their perspective on the tech talent wars and how to get hired in 2026. The resounding answer on how to get a job? JUST START DOING THE JOB! If you want to be a designer, start sending designs to companies you want to be hired by — don’t just sit around waiting to be hired. The biggest value you can bring is a “high agency” mindset to your company and the role. Show you get after it!

Is this the end for the Roomba? Why iRobot went bankrupt | E2224

Domestic robots have never been hotter… so why is iRobot in so much trouble?! On TWiST, we’re investigating the recent troubles facing the automated vacuum robot, Roomba. We’ve all seen these little discs sweeping up our friends’ floors… but now the company behind them is running out of cash. What happened to iRobot, and would things have turned out differently if they had been sold to Amazon back in 2022? PLUS why Jason thinks you should spend your disposable income on investing… Is Alex still a journalist, and what does that actually mean for his portfolio?… Are founders and investors too cautious when it comes to signaling risk?… Why did all those internal Pipe documents leak online?… And MUCH MORE!

Disney and OpenAI sign landmark deal… and we saw it coming! | E2223

FINALLY, you can hang out with Kylo Ren and Olaf the Snowman… thanks to the magic of AI. On TWiST, we’re digging into the mega OpenAI-Disney deal. Mickey is giving Sam Altman a $1 billion investment AND will allow is copyrighted characters to appear in Sora and ChatGPT images. Of course, Jason predicted this would happen WAY BACK during the summer months and even showed off his “Darth Calacanis” creation on the “All-In Podcast.” PLUS Amazon has been launching and pulling AI features from Prime Video… what gives? Jason’s predictions on the coming AI blowback and who’s on what side. Why he’s so focused on Education, Health Care, and Housing as issues. AND why founders should always take calls from Big Companies, even if it might just be a fishing expedition. It’s a new Friday TWiST! Check it out!

“The best founders find a way to make it happen”: VC Roundtable with Bryan Kim and David Clark | E2222

Boom is still making supersonic jets but ALSO plans to start selling their turbines as power sources for AI data centers. It’s a perfect example of problem-solving on the go and how “the best founders… MAKE IT HAPPEN.” Join us for another insightful VC roundtable episode, featuring special guests Bryan Kim (a16z) and David Clark (Ven Cap). They’re discussing why Boom’s turbine announcement is about necessity AND opportunity PLUS… - Why we might NOT be in an AI bubble after all - Promoting your startup without spending your entire runway on marketing - Why founders need to be RELENTLESS - Bill Gurley’s classic response about Uber’s Total Addressable Market - AND LOTS MORE

FLASHBACK: The future of remote work, juggling APIs, and dream integrations with Wade Foster of Zapier | E2221

Today, Zapier’s a multi-billion company helping enterprises integrate AI agents and other time-saving shortcuts into their workflows… but we had the founder on TWiST when they were just getting started! In a 2016 chat, founder Wade Foster walked JCal through their 2012 seed round, running a small entirely remote team with no HQ, the complexities of building a tool that relies on third-party APIs, and why Microsoft Office was the “Holy Grail” for his integration software. PLUS we’ve got a new entrant in your Gamma Pitch Deck competition! Tour CEO/CTO Amulya Parmer tells us how his app is saving property managers time and grief, while eliminating “looky-loos” and increasing their “hit rate.” FINALLY, Alex chats with Tomas Puig of TWiST 500 marketing analysis startup Alembic. It turns out, LLMs aren’t ideal for scrutinizing marketing campaigns because they lack the requisite historical data. Find out how they’re using Spiking Neural Networks (SNN) to dig deeper than GPT and Claude can go.

What’s REALLY going on with those “ads” in ChatGPT | E2220

A screenshot showing a “Target Ad” in ChatGPT results went viral… over the weekend, but the OpenAI chatbot has NOT actually opened the advertising floodgates just yet. As ChatGPT staffers were quick to explain on social media, this was actually an invitation for a user to integrate their Target account into ChatGPT, for an easier agentic browsing and shopping experience. But it does prompt Jason and Alex to ask some intriguing questions… Is OpenAI just waiting for Google or someone else to launch AI ads first, and face the inevitable flood of backlash they’ll presumably receive? Is there someone at OpenAI already thinking DEEPLY about how these in-feed ads should work? And what does this mean for their wager on when ChatGPT is going to actually get ads? Is that already decided?