Aussie Entrepreneurs Taking On Tokyo!

BIG thank you to Paul for the feature in Australia's number 1 commercial news title, realcommercial.com. I've cycled with Paul on the Tokyo West-Side Cycling & Food Tour and had a blast hosting him on each of his visits.

Below is a small extract of Paul's article published on Real Commercial. The entire piece, featuring a small selection of the many talented Australians 'giving it a crack' in Japan, can be found here: Aussie Entrepreneurs Taking On Tokyo.

While the bustling, neon-lit metropolis of Tokyo might seem a world away from the laid-back beaches of Australia, a wave of True Blue entrepreneurs are proving that Aussie ingenuity knows no bounds.

Leaving the familiar shores of home behind them, a growing number of Australians have set their sights on the Land of the Rising Sun and have found remarkable success.

From tech innovators to hospitality heroes, read on to discover the secrets behind their triumphs, the challenges they’ve overcome, and the unique blend of Aussie spirit and Japanese savvy that’s helped them shine on the Tokyo stage.

DIG Tokyo Tours

When Melbourne-born storage and warehousing manager, Andy Miller, relocated to Tokyo in 2016 he had no idea just how drastically his career direction would change.

“My wife was presented with the opportunity to assist her company enter the Japanese market and we thought it’d be a brilliant opportunity to put our two young boys into the public education system and get them fluent in Japanese,” explained Mr Miller.

No stranger to the country, Mr Miller had first lived in Japan back in 2001 and had since travelled extensively back and forth after meeting his Japanese-born wife.

It was this knowledge and appreciation of the local culture that proved to be the genesis for a life-changing business.

“I’ve always enjoyed playing around with bikes,” he said. “Most of the Tours back then in Tokyo were pretty formulaic by design and I thought it’d be a great opportunity to get people out into the local neighbourhoods on bikes to complement their trip and provide an honest local insight into the city.”

DIG Tokyo Tours offers unique and immersive experiences that go beyond the typical tourist traps. Socially responsible, the small-group, family and private tours delve into the heart of Tokyo’s vibrant neighbourhoods, showcasing hidden gems, local traditions, and authentic culinary delights.

In the decade-plus since he started, the business has grown and amassed a raft of accolades including Traveller’s Choice Awards on Tripadvisor, global media coverage, and an inclusion in Airbnb’s ’10 most popular cycling tours’ globally.

Part of this success believes Mr Miller is his Aussie “no BS” approach to business: “Authenticity is valued over superficial and flashy. I want guests walking away feeling that they were part of a living neighbourhood on a non-manufactured day out.”

But navigating the complexities of bureaucratic red tape and language difficulties in the Land of the Rising Sun isn’t for the faint of heart, said the tour operator.

“The language has been the biggest barrier and something that I’m always working on,” he said.

“Particularly when dealing with the copious amounts of technical paperwork and the business taxation requirements. As advanced as Japan seems on the service level, it’s swamped with paperwork and ‘rubber stamping’ for even the simplest of tasks.

“The banking system is often a good example of this. However, now that most of the company’s internal systems are in place, and trust has been established, daily operations tend to run much smoother.”

Looking back on the last 10 years, the 45-year-old concedes that he might have done things differently but that his priorities have also changed along the way.

“I most definitely undervalued my services and skillset in the initial years,” he said.

“It was a long hard slog building a reputation and earning a respectable wage in the early stages. The small amounts of surplus income I had in the initial years should have been directed towards experts in the necessary fields instead of spending endless hours educating and trying to figure everything out myself. Work life balance could have been a hell of a lot better. I’m sure many small business operators can attest to this.

“I was initially looking at world domination but in all honesty as long as I can bring a smile to guests faces and spark some curiosity in Japan, that’s all right by me. Keeping the operation intimate, local and working on strengthening partnerships with local personalities, vendors and likeminded small tourism providers such as myself.”

Source: Real Commercial (29th December 2025)

Author: Paul Ewart