This Week in Startups

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Today's show:
*Before Bespoke's "travel concierge" chatbot could actually hold a conversation, founder/CEO Akemi Tsunagawa and her team quietly answered customers themselves. That "fake it till you make it" strategy paid off. Bespoke landed Narita Airport as a customer based on the strength of their "chatbot" answers, and now the team runs three companies, and is expanding into shipyard robots.
In the fourth and final edition of TWiST Tokyo for Summer '26, Jason and Akemi discuss her thesis: "solve the labor gap first, [then] build the tech to math." Plus insights into Japan's tourism boom, how founders should consider the country's accelerating population decline, the economics and politics of importing foreign labor, and why AI may already be taking over more jobs than you think.
Guest
Akemi Tsunagawa on X: https://x.com/AkemiTsunagawa
Bespoke: https://www.be-spoke.io/
Bebot: https://www.bebot.io
BeTrained: https://www.be-spoke.io/en/be-trained
Relevant Links
Disrupting Japan: "Silicon Valley Has Chatbots All Wrong": https://www.disruptingjapan.com/silicon-valley-has-chatbots-all-wrong-heres-how-they-really-make-money/
CNN on Japan's population decline: https://www.cnn.com/2025/08/07/asia/japan-biggest-population-decline-record-intl-hnk
Paul Graham: "Do Things That Don't Scale": https://www.paulgraham.com/ds.html
Wispr Flow: https://wisprflow.ai/
TripAdvisor: https://www.tripadvisor.com/
KPMG on Japan's Business Manage Visa Reforms: https://kpmg.com/xx/en/our-insights/gms-flash-alert/flash-alert-2025-195.html
Business Traveller on the "Akiya" renovation trend: https://www.businesstraveller.com/insights/features/japan-akiya-boom-buying-abandoned-homes/
THR on the 2004 satirical film "A Day Without a Mexican": https://www.hollywoodreporter.com/news/general-news/a-day-without-a-mexican-20-years-later-1236293209/
Founder University x Japan: https://tokyo.founder.university/
JETRO: https://www.jetro.go.jp/en/
Antler in Japan: https://www.antler.co/location/japan
Timestamps:


0:00 Founder U Japan Cohort 3: Coming in Jan 2027!
1:06 Introducing Akemi Tsunagawa, founder of Bespoke
3:08 Why investors passed in 2015
4:49 Selling Narita Airport on Bebot
6:29 The roots of Japan's tourism explosion
9:27 Odoo - The all-in-one business platform. Get started for free at https://Odoo.com/twist
14:17 Japan's population decline, by the numbers
20:06 Quo (formerly OpenPhone) - Quo gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at https://quo.com/TWiST
21:38 Training foreign workers via smart glasses
27:50 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 https://northwestregisteredagent.com/twist
33:06 Moving into shipyard robotics, too?
37:44 Some customer development lessons
48:21 Plans for even more expansion
52:52 Q&A: How AI changed hiring
 
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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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Today's show:
AI models can solve PhD-level math equations and code an app in minutes… So why does everything they design look like identical slop? Thais Castello Branco, founder of Taste Labs, raised $18.5M in seed funding to teach frontier models about aesthetics and outputting quality content. She talks to Jason and Lon about why even frontier models regress to the mean on subjective tasks, how paid "TasteMakers" can improve output quality, and whether AI accelerates or destroys the half-life of "what's cool."
PLUS Leopold Aschenbrenner's AI hedge fund liquidated its public stock portfolio, but it may be too soon to count this 25-year-old completely out. Google Earth adds AI generation and turns into a misinformation factory. LinkedIn and Substack join the AI slop crackdown. And why does every venture capitalist seem to have an opinion about the Ceuta border crisis?
Guest
Thais Castello Branco on X: https://x.com/thaiscbranco_
Taste Labs: https://tastelabs.com/
Amplify Partners: "Kill the Slop": https://www.amplifypartners.com/blog-posts/kill-the-slop-announcing-our-investment-in-taste
Relevant Links
Leopold Aschenbrenner's essay "Situational Awareness": https://situational-awareness.ai/
CNBC on SA fund collapse: https://www.cnbc.com/2026/07/31/leopold-aschenbrenner-situational-awareness-fund-fire-sale.html
Henk van Ess thread on Google Earth + Nano Banana: https://x.com/henkvaness/status/2082912544394498228
Substack CEO Chris Best: "Against Claudefishing": https://post.substack.com/p/against-claudefishing
NPR on the Ceuta crisis: https://www.npr.org/2026/07/31/g-s1-136507/morocco-spain-migration
Ethan Goodhart's self-driving golf cart post: https://x.com/EthanGoodhart/status/2082136189998682598?s=20
"Wind" app on TestFlight: https://testflight.apple.com/join/zZqmhhwf
TechCrunch: "Gritt exits stealth": https://techcrunch.com/2026/07/21/gritt-exits-stealth-with-34-million-for-robots-to-build-solar-plants-then-everything-else/
CA Gov: Project Nexus solar-covered canal announcement: https://www.gov.ca.gov/2026/04/29/governor-newsom-announces-the-completion-of-first-of-its-kind-solar-covered-canal-in-the-central-valley-piloting-a-new-way-to-save-water-and-reduce-costs/
Molly Wood's "Everybody in the Pool" podcast: https://www.everybodyinthepool.com/
Timestamps:
 
0:00 Coming up on today's show…
1:23 Thais Castello Branco on teaching models to have good taste
10:45 YSecurity - The on-demand security team for startups. Need enterprise-grade security without hiring a $400k CISO? YSecurity gives you 40+ expert engineers, matched to exactly what you need, by the hour, with your first six hours completely free. Go to https://YSecurity.io/TWIST
15:19 The "TasteMaker" community of paid human curators
20:37 MongoDB - AI-assisted and agentic coding is helping you build faster than ever. Start building at https://MongoDB.com/ai
24:40 Jason's personal "cool hunter" prompt
30:16 Odoo - The all-in-one business platform. Get started for free at https://Odoo.com/twist
37:36 Situation Awareness lacked situational awareness
46:59 Claude models hacked three external organizations
50:54 Google Earth adds Nano Banana for some reason
54:24 The AI Slop crackdown spreads
57:54 Too many opinions about the Ceuta migrant crisis
1:04:05 Self-driving golf carts and also cars
1:09:53 Robot arms are installing solar panels
 
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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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Today's show:
*There are $100 trillion in global assets sitting on top of what Hanover Park co-founder/CEO Chris Hladczuk calls "human duct tape": armies of accountants in offices patching together work from various legacy tools (QuickBooks, Excel) that are holding funds' own data hostage. Can all of this be replaced with AI? Find out how their startup went from overseeing $1B to $20B in assets in just 15 months.
PLUS, we flash back to March 2020, when Jason and Figma co-founder/CEO Dylan Field broke down the design tool's initial go-to-market strategy, made some WILDLY inaccurate COVID predictions, and considered anxiety about "SaaS burnout" years before the category went full apocalyptic.
Guests:
Chris Hladczuk on X: https://x.com/chrishlad
Hanover Park: https://www.hanoverpark.com/
Dylan Field: https://x.com/zoink
Figma: https://www.figma.com/


Relevant Links:


Turner Novak on X: https://x.com/TurnerNovak
Banana Capital: https://www.bananacapital.vc/
Emergence Capital: https://www.emcap.com/
Lux Capital: https://www.luxcapital.com/
Susa Ventures: https://susaventures.com/
Bill.com: https://www.bill.com/
METR: https://metr.org/
Granola AI note taker: https://www.granola.ai/
Vanta: https://www.vanta.com/
Foo Camp on YouTube: https://www.youtube.com/c/foocamp
TechCrunch Mahalo coverage: https://techcrunch.com/2014/01/27/inside-mobile-news-launch/


Timestamps:

0:00 Hanover Park & the fund admin problem
3:32 Why funds outsource instead of building
5:44 Why fund accounting is so complex
10:38 The "one-click migration" goal
10:48 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 https://northwestregisteredagent.com/twist
13:51 Context vs. intelligence gaps
16:11 No PMs, No Designers
20:46 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
23:18 This is a $100T opportunity
25:36 Flashback w/ Dylan Field of Figma
29:15 Sentry - Your team should be focused on shipping features — not chasing down bugs. New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST
31:22 Pre-AI enterprise security worries
36:30 SaaS overload and SaaS burnout
37:30 The evolution of Figma pricing
42:38 The rise and fall of Mahalo dot com
51:38 The work-from-home revolution begins
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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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This Week In Startups is made possible by:


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Today's show:
Forget the triple-triple-double-double-double; the new bar for startups hoping to raise venture capital has reached the stratosphere, though our venture panel is worried that startups are focusing too much on today's problems that may not become companies tomorrow. During a lively VC roundtable, Cowboy's Aileen Lee, Floodgate's Mike Maples, and Lerer Hippeau's Ben Lerer joined Alex to dig into exiting pre-AI startups, rising valuations, token spend, why they are keeping their funds small, and whether the government just tripped OpenAI and Anthropic!


Guest Links:
Aileen Lee https://x.com/aileenlee
Cowboy VC https://cowboy.vc
Mike Maples https://x.com/m2jr
Floodgate https://www.floodgate.com
Bene Lerer https://www.linkedin.com/in/benjlerer
Lere Hippeau https://www.lererhippeau.com


Timestamps:
0:00 Aileen Lee, Mike Maples, and Ben Lerer join the show
5:13 Venture liquidity returns: what SpaceX/Stripe distributions mean for LPs
9:13 Bending Spoons prices IPO at $29/share, roughly $18.4B valuation
10:31 Agree.com - Stop chasing invoices and automate your entire contract-to-cash stack. Go to https://agree.com and tell them Jason sent you to get 50% off for life!
12:09 "Companies get bought, not sold" — Ben on taking first offers seriously
17:41 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
19:34 Mutiny's burn-the-boats AI pivot with Jaleh Rezaei
20:19 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 https://www.northwestregisteredagent.com/twist
22:15 Mike's KeepSafe story: the "rule of 70" and profit-first companies
25:12 The new growth bar: 5x, 4x replaces triple-triple-double-double
28:55 Fund size is your strategy: why Floodgate and Lerer Hippeau stay small
30:11 CLA - Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at https://www.claconnect.com/withyou
37:39 The $100M Series A: Starcloud, General Intuition, Scale Cognition, Scout AI
40:35 King-making rounds and why mega-seeds destroy optionality
54:11 Open-weight models: the GLM-5.2 moment and going model-agnostic
55:30 Why fine-tuning open models is a treadmill, with Cursor/Kimi as an example
1:03:28 Grading the Trump administration on Mythos and Fable
1:06:33 Rising anti-AI sentiment, the wealth gap, and lessons from social media
1:11:43 Raising kids in the post-intelligence era
1:12:35 Where to find the panel and what each firm is investing in


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Check out all our partner offers: https://partners.launch.co/
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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Today's show:
*It's another All Star Summer, as we welcome back some of our favorite guests from throughout "This Week in Startups" history.


Chamath Palihapitiya's development platform 8090 just raised $135 million, and he's using it to go after a $4 trillion market: the software maintenance, migration, and middleware spending that's currently "pure waste" for enterprises.


Find out why the All-In Podcast bestie says every company should use AI to build custom software the way that Google, Facebook, and Meta already do, then go inside Software Factory, the "system on a chip" organizational model, and why Chamath believes AI will allow every human on Earth to start their own company.


Guest:


Chamath on X: https://x.com/chamath
8090: https://www.8090.ai/
Learn With Me on Substack: https://chamath.substack.com/p/learn-with-me
Drink With Me: https://www.drinkwithme.com/age-verify.html
All-In Podcast: https://allin.com/
Social Capital: https://www.socialcapital.com/


Relevant Links:


8090 Series A announcement: https://x.com/chamath/status/2071571183665881515
Salesforce Ventures: https://salesforceventures.com/
Craft Ventures: https://www.craftventures.com/
The Production Board: https://www.tpb.co/
WNDR: https://www.wndr.vc/
LAUNCH: https://www.launch.co
Coatue Management: https://www.coatue.com/
Jack Dorsey: "From Hierarchy to Intelligence": https://block.xyz/inside/from-hierarchy-to-intelligence
Thomas Keller's The French Laundry: https://thomaskeller.com/tfl/


Timestamps:
0:00 It's TWiST All-Star Summer!
0:44 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
3:21 Chamath's origin story
7:54 Tom Sawyer entrepreneurship
11:29 Shopify - Turn those What If's into sales with the ecommerce platform powering millions of businesses. Sign up for your $1-per-month trial today at https://shopify.com/twist
16:25 The $5 trillion software market
21:06 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist
25:00 Building "a co-founder for every human"
31:51 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 https://northwestregisteredagent.com/twist
35:00 How product development lost its way
45:00 Regulated industries are the beachhead
50:00 Raising the $135M Series A
55:00 8090's "System on a Chip" model
1:04:44 What to tell your kids about AI


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