How Bespoke faked AI until it actually worked (w/ Akemi Tsunagawa) | E2320

How Bespoke faked AI until it actually worked (w/ Akemi Tsunagawa) | E2320

Author: Jason Calacanis August 3, 2026 Duration: 1:02:15
This Week In Startups is made possible by: Odoo https://Odoo.com/twist Quo https://quo.com/TWiST Northwest Registered Agent https://northwestregisteredagent.com/twist 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 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 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 Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 50

This Week in Startups
Podcast Episodes
Jason turned $11 and one tweet into 1.1M views | E2311 [not-audio_url] [/not-audio_url]

Duration: 1:29:50
This Week In Startups is made possible by: Quo https://quo.com/TWiST PayPal Open https://paypalopen.com Northwest Registered Agent https://northwestregisteredagent.com/twist Today's show: *Jason spent $11 building out Po…
Danny Bernstein left Big Tech to fund farm-bots | E2310 [not-audio_url] [/not-audio_url]

Duration: 1:00:53
This Week In Startups is made possible by: NetSuite https://NetSuite.ai/TWIST Squarespace https://squarespace.com/twist YSecurity https://YSecurity.io/TWIST Today's show: *America posted 400,000 farm jobs last year, and…
Why Data Is the Next $1 Trillion Market [not-audio_url] [/not-audio_url]

Duration: 1:06:00
This Week In Startups is made possible by: Digital Ocean - do.co/twist Agree.com - agree.com Every.io - every.io. Today's show: How many startups matter in tech? Fewer than you think. That's why venture capitalists are t…
$100T is managed by "human duct tape" | E2308 [not-audio_url] [/not-audio_url]

Duration: 58:01
This Week In Startups is made possible by: Northwest Registered Agent https://northwestregisteredagent.com/twist Vanta https://www.vanta.com/twist Sentry https://sentry.io/twist Today's show: *There are $100 trillion in…
Why the VC Hype Cycle Always Gets It Wrong | VC Roundtable | E2307 [not-audio_url] [/not-audio_url]

Duration: 1:14:10
This Week In Startups is made possible by: CLA - www.claconnect.com/withyou Northwest Registered Agent - www.northwestregisteredagent.com/twist Agree.com - www.agree.com Today's show: Forget the triple-triple-double-doub…
Chamath on why young people need more agency, risk, and adventure [not-audio_url] [/not-audio_url]

Duration: 1:12:05
This Week In Startups is made possible by: Plaud https://Plaud.ai/twist Shopify https://shopify.com/twist LinkedIn Jobs https://LinkedIn.com/twist Northwest Registered Agent https://northwestregisteredagent.com/twist Tod…
Why F1 Teams are Replacing Wind Tunnels with Smart Tape | E2305 [not-audio_url] [/not-audio_url]

Duration: 1:30:26
This Week In Startups is made possible by: Plaud - https://Plaud.ai/twistSentry - https://sentry.io/twistNorthwest Registered Agent-https://northwestregisteredagent.com/twistDigitalOcean - https://do.co/twist Today's sho…
Why the Future of Video Games is Moving Back to the Dinner Table [not-audio_url] [/not-audio_url]

Duration: 1:08:51
This Week In Startups is made possible by: Deel - deel.com/twist Northwest Registered Agent - northwestregisteredagent.com/twist LinkedIn - linkedIn.com/twist Today's show: Jason sits down with Brynn Putnam, CEO and foun…
The hottest running app has nothing to do with speed | E2303 [not-audio_url] [/not-audio_url]

Duration: 1:03:04
This Week In Startups is made possible by:Agree - https://agree.comQuo - https://quo.com/TWiSTSuperhuman - https://superhuman.comToday's show:In this double-header, Jason and Lon chat with Louis Phillips, founder of the…
Why SpaceX Buying Cursor Changes Everything [not-audio_url] [/not-audio_url]

Duration: 1:41:05
This Week In Startups is made possible by: Deel - deel.com/twist LinkedIn - linkedIn.com/twist Northwest Registered Agent - northwestregisteredagent.com/twistPlaud - https://Plaud.ai/twist Today's show: Anthropic stabbed…