I started my first startup in 1991 Tokyo, and I’m still building - Ikuo Hiraishi
And what made bubble era startups so special...
This week’s The Cool People Podcast, I had the honor of sitting down with Ikuo Hiraishi, a serial entrepreneur, venture capitalist, and professor who has resiliently shaped Japan’s startup ecosystem over the past two decades.
From co-founding his first company in 1991 to co-founding nine ventures, going public and an M&A exit, Ikuo has been in the arena since the early days of the internet.
In our conversation, we trace his journey from those early startup experiments to the rise of Tokyo’s Bit Valley movement, a time when Japan’s digital future was still being imagined.
Along the way, we dive into the structural and cultural forces that continue to define Japan’s startup ecosystem — including its cautious approach to risk, the stark difference in venture capital deployment compared to Silicon Valley, and why so many founders aim for "first base" instead of swinging for the fences.
Ikuo shares not only his professional path but also his personal philosophy — how he reframes setbacks, finds meaning in challenges, and remains committed to building even after success.
We also explore his current work as a professor at Musashino University, where he's helping rethink how entrepreneurship is taught, and his latest initiative, Go Global Catalyst, which aims to connect Japanese innovation to the world.
If you’re curious about why Japan’s startup culture is both quietly special and frustratingly behind, or how its current state fits into the long arc of Japan’s history as a nation of builders, artisans, and reinvention, this is a masterclass in both context and perspective.
Ikuo doesn’t just understand Japan’s startup ecosystem — he’s helped shape it.
This is a thoughtful, wide-ranging episode for anyone interested in where Japan has been, where it’s going, and what it means to build for the long term.
→Find Ikuo here: https://www.linkedin.com/in/ikuohiraishi/
→Go Global Catalyst: https://www.goglobal-catalyst.com/
No time to listen? Scroll down for the full summary👇
Summary
Ikuo Hiraishi’s entrepreneurial journey began in March 1991, sparked by a regulatory window that briefly slashed the capital needed to start a company. This shift opened the floodgates for new ventures and catalyzed his decision to become a “builder” rather than follow Japan’s traditional corporate track. It was an early lesson in how policy can unlock entrepreneurial energy — a theme that would shape his view of innovation for years to come.
We explore the early days of the internet in Japan, from Ikuo’s first exposure via Netscape Navigator, to helping startup launch in Japan, to co-founding Inscope in 2000. He later played a key role in Web Crew, a pioneering auto insurance comparison site that went public in 2004. These stories paint a vivid picture of the "Bit Valley" movement in late-'90s Tokyo — a chaotic, creative time when Japan's startup scene was just beginning to take shape.
One major thread of the episode is the stark gap in venture capital between Japan and Silicon Valley — a 63x difference that Ikuo attributes to deep-rooted differences in culture, history, and institutions. He reflects on how Japan’s stable domestic market, language barriers, and a lower tolerance for risk create headwinds for bold, global-scale innovation.
Ikuo offers a nuanced take on the mindset of Japanese founders, who often aim for a “first base” outcome — typically an early IPO — instead of a high-risk, high-reward “home run.” He connects this to the rise of TSE Mothers and NASDAQ Japan, which made it possible for startups to go public early, often as a means of de-risking personal guarantees rather than scaling globally.
Reflecting on execution vs. ideation, Ikuo expands on a quote from TechCrunch’s Keith Teare: “Entrepreneurs don’t always have the ideas, but they know how to execute.” He connects this with Peter Drucker’s philosophy that entrepreneurship is about recognizing and acting on change — highlighting how deregulation in Japan’s insurance sector gave rise to Web Crew.
Today, Ikuo is a professor at Musashino University, where he’s pioneering a new kind of entrepreneurship education — one that’s grounded in Japanese context but designed for global impact. His goal: cultivate a new wave of entrepreneurs who can thrive amid Japan’s shrinking population and shifting industrial needs.
On a personal level, Ikuo speaks candidly about navigating setbacks. After his initial success with Web Crew, he hit a trough that forced him to redefine his purpose. His mindset now centers on extracting meaning from obstacles — a resilience forged through decades of building, failing, learning, and rebuilding.