The Delphi Roar: October 19th, 2025
Dear Members and Advisers,
On Sunday, I was slightly surprised to be asked for a coffee by one of the regular Delphi cocktail attendees. She had not attended for several months, so I had reached out to invite her to the October event…
The rest of this content is for Delphi members only, given its sensitivity.
The Shifting Sands of Entrepreneurship in Japan: Navigating New Realities
A new frontier in online shopping is opening in the United States, and its tremors are already being felt across the Pacific. The launch of "Instant Checkout" on ChatGPT, powered by a partnership between OpenAI and Stripe, signals the dawn of a new era.
This development in Conversational Commerce Japan is not a matter of if, but when. The potential for OpenAI E-commerce to disrupt established players is immense, but its success will hinge on navigating Japan’s unique market dynamics and its complex ecosystem of payments. For business leaders, the critical question is how this model will adapt—and which Japanese giants will move first to claim this new territory.
Seen in the Network
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Delphi Cocktails September 2025
Connect with Tokyo’s top executives over curated cocktails and high-level conversation, 51 floors above the city skyline.
Rebuilding LEGO Japan Post-COVID
LEGO Japan's leader shares exclusive insights on post-pandemic strategy, digital agility, and resilient leadership.
Heard in the Network
“AI is less of a priority in Japan, from the Country Manager point of view, because s/he finds it so challenging to reduce staff. So one of the key benefits of AI is rules out.”
“We found that AI worked for a while with our staff, but when it started to spit out patently inaccurate information, they were shocked and became much more sceptical. In my company this was the big “stopper”. ”
“People think investing for their future is boring, but you can invest in things which are really quite fun - cars, watches, swords. Some friends bought the very last examples of the Holden, an iconic but discontinued Australian car brand, and it’s gone up 1000%. ”
“I am amazed that after 30 years in Japan we still have so low market shares. What have my predecessors been doing? ”
“One country manager of a very large foreign firm said he did not need my consulting services, because his Japanese staff were already 100% familiar with the company’s vision, values and strategy. I challenged him to introduce me to 3 random staff members, and none of them could mention a single company value or the mission or what made that company unique. Nor could they explain the corporate logo. I was hired.”
“A lot of country managers don’t know that their sales team is using slide decks which have been “unofficially” revised to be effective in the Japanese market. ”
“We are pushing hard on AI (country manager for a leading European company). HQ is fully behind us and encouraging us to start. We are planning some serious training for staff, including specialized training for e.g. Sales and Logistics. I am telling our staff that “you will keep your job BECAUSE of AI, not in spite of it. AI is going to make our company and processes quicker, better and more profitable!””
“There is a very active “grey zone” in corporate AI. The staff officially set the barrier very high, because they are scared AI will replace them. So officially AI is not used much. But in private, everyone is using AI for personal translation and drafting. ”
“I am the Head of AI in my company, and I get very worried looks from my colleagues, as I go round trying to implement the introduction of AI into my company. ”
“Be careful (as a company) about sending more than ¥1 million offshore - it will trigger a visit from government tax inspectors.”
“My aim is to make my foreign product part of the Japanese cultural landscape and part of daily life for Japanese people. If we don’t achieve that, we are doomed. ”
“When I work with a Japanese company, I infiltrate middle management. I tell the country manager to leave me alone, because I don’t want to be seen as the head office spy. After months of drinking and bonding, I get accepted and I can roll out my suggestions. ”
“Every country manager should be looking at how digital marketing is being affected by AI compared to Google. You might do very well on Google, but do very badly on AI search. And AI search is threatening to bury Google. ”
“We had to fire our high-performing GM for sexual harassment. It turned out he was out of control, and was a repeat offender. The problem was not that none of the victims told me about it! However, staff were pleased and impressed that I fired him once I found out, even though he was a top performer. ”
“I am picking up some amazing people from the luxury industry who are either being downsized or not enjoying luxury culture any more, or who want to be a “big fish in a small pond” rather than a small fish in a huge (and sometimes toxic!) pond. ”