Building Global: Why Timing Trumps Perfection in Entrepreneurship

Davide Rossi turned study abroad struggles into a 25-nationality company spanning five markets. Here is the story of that success.

Most entrepreneurs wait for the perfect moment to launch their business. Davide Rossi, co-founder and CEO of Go! Go! World, proves that imperfect timing can be your greatest advantage. What started as personal frustration with Japan’s complex student visa process has grown into a global study abroad agency operating across five countries with over 25 nationalities on staff.

Rossi’s journey from Italian web developer to international entrepreneur reveals a counterintuitive truth: entering markets when conditions seem challenging often creates the biggest opportunities. His approach to scaling across cultures—letting regional leaders run their markets their way—offers a practical blueprint for building truly global companies without losing your core identity.

From code to classrooms to CEO

Rossi’s path to entrepreneurship began with a mid-career language learning goal. Working as a web developer in the UK with good pay and perfect work-life balance, he decided to learn Japanese before getting “too old.” The six-month language program in Japan became what he calls “the best experience of my life.”

But the preparation process nearly derailed everything. “When I decided to come to Japan as a student, it was really hard to do all of the preparation by myself,” Rossi recalls. “I had to research the information and choose the school, accommodation, and try to understand how my life in Japan was going to be. Doing this from Europe was a really difficult process.”

The contrast was stark. After months of stress and nearly giving up twice, Japan exceeded every expectation. “Once I arrived, I thought, this is the best thing I could do! I had the best time of my life. Everything was so good.”

That gap between expectation and reality became his business opportunity. “I thought that there must be a lot of people that are dreaming to go to Japan but they get stuck in the preparation process and give up,” he explains. Using his web development skills, he created a site that quickly gained popularity, allowing him to transition from Italian language teaching to running his own company.

Learning business the hard way

Rossi entered entrepreneurship without an MBA, business connections, or prior startup experience. “I went through all the possible challenges that a person can when setting up a business, especially in a foreign country,” he admits. Language barriers, legal complexities, and basic business fundamentals like balance sheets and recruiting were all learned through trial and error.

“If I had that knowledge, I think the first 4 or 5 years could have been much smoother,” he reflects. “Some people get started through education, others through connections. Then there are those like me who just keep hitting their face against a wall and eventually get there.”

The Japanese business environment added its own learning curve. Decision-making timelines stretched far beyond Western expectations. “Even a simple business transaction can take much longer, as it’s natural for the Japanese to be very cautious with an initial approach,” Rossi notes. But he learned to see this as strength rather than weakness. “While they may take a while to consider and make a decision, once the decision is made they take action exceptionally well.”

The secret to scaling across cultures

Go! Go! World’s expansion to South Korea, and eventually to Italy, France, and Spain, required rethinking traditional top-down management. Rossi’s solution was radical delegation combined with cultural authenticity.

“I think one key factor for us has been putting global leaders in charge of their own regional market and giving them the flexibility to run it the way they see as best,” he explains. “Our South Korean business is run very differently from our Japan headquarters. What works great in one market may not work well in another.”

This approach proved its value during COVID-19. When Japan closed its borders for two years, cutting off Go! Go! World’s core business, the independently operating South Korean division kept the company afloat. “I know companies bigger than us, with much more experience and many more knowledgeable people than us, that struggle to replicate their business in a different country,” Rossi observes.

The key is maintaining a common core while allowing regional adaptation. Regional leaders get support when needed but are responsible for developing their own ideas and strategies. “I find it better than leading top-down and giving a million guidelines for running the business unit.”

Managing 25 nationalities without missing a beat

With over 25 different nationalities across offices in five countries, Go! Go! World faces communication challenges that would overwhelm most organizations. Rossi’s solution is elegant in its simplicity: stop trying to manage cultural differences.

“After you pass a certain number of different nationalities, when there is no longer a predominant nationality, how do you adapt to that? For Go! Go! World, it’s about letting everyone be themselves. That brings out the best work.”

This wasn’t an intentional strategy from day one. “We didn’t really have an intentional company culture at the beginning. I didn’t have a business background. I couldn’t think about all these things.” But as the company grew, they realized that authenticity trumped forced cultural adaptation.

“At this point in our company, we don’t really look at differences in culture. We just go straight to the point,” Rossi explains. “We have so many nationalities that nobody has to adopt another’s culture to fit in. Everyone can be themselves, and because of that, communication turns out smooth for us.”

Why now is the perfect imperfect time

Rossi sees current global tensions and Japan’s economic challenges as opportunities rather than obstacles. While political leaders push “our country first” policies, he argues this creates openings for entrepreneurs willing to move against the trend.

“If you want to start a business in Japan, you can’t wait 10 or 15 years until it’s the perfect time,” he says. “It’s better to move now when less people are doing it than when everyone is doing it.”

Japan’s weak yen and stagnating salaries might deter many, but Rossi sees these as temporary conditions masking deeper opportunities. “Japan is finally opening up to the startup world, and foreigners. After the experience with COVID when the Japanese government closed everything down, I think they realize that they must reopen.”

The infrastructure is rapidly improving. Fifteen years ago, Japan lacked startup events, social media networks, incubators, and coworking spaces. “Japan maybe takes a bit longer to start things, but when they start they do it really well,” Rossi notes. “So I think it’s a good time now to be part of this entrepreneurial movement and be one of the first rather than one of the last.”

The language investment that pays 10x returns

While Go! Go! World serves international students, Rossi strongly advocates for Japanese language learning among foreign entrepreneurs. “You can definitely be successful with just your native language,” he acknowledges, adding that knowing Japanese “will probably unlock 10x more opportunities, 10x more money, and 10x more success.”

He recommends six months in a language school as the optimal investment. “From my personal experience, 6 months in a language school worked amazingly. It was the right timing for me and it helped massively.”

The timing matters. “Once you get working, life in Japan can be very, very busy. You could be too late,” he warns. Those initial months also provide networking time and cultural understanding that prove invaluable as business relationships develop.

Building for the long game

Go! Go! World’s future plans reflect Rossi’s systematic approach to growth. The company is expanding in two directions: more destinations and deeper services. Neither is simple to execute.

Adding new countries requires extensive on-site research, relationship building, and understanding complex visa procedures. “We don’t just add any school to our network, we need to visit them and understand what’s good about them,” Rossi explains. “The complication increases each time we add a destination.”

The second direction involves supporting students beyond their initial study period. “How we can support students even more, even in their life in Japan after they study. That’s something we’re always looking into.” It’s a long-term play that could take five to ten years to fully develop.

The courage to leave your comfort zone

Rossi’s final message transcends business advice. He advocates for international experience as essential personal development, regardless of age or circumstances.

“I think people should, at least once in their life, get out their country, get out their comfort zone and study abroad,” he urges. “Maybe push yourself to learn a different language. You will meet people in your life and make connections.”

The experience doesn’t require permanent relocation. “You don’t have to stay abroad forever. But I think it’s something that everyone should try once.” The key is action over analysis. “Just do it, and just don’t think about doing it. I know it’s difficult to leave your home, but just do it, and you will never regret it.”

So, take note: While others analyze market conditions, the smartest entrepreneurs are already there, building relationships and learning languages.

Executive takeaways

Move when conditions look challenging: perfect timing is a myth—competitive advantages come from entering markets before they become crowded.

Give regional leaders real autonomy: common core values matter, but local execution should reflect local expertise and cultural understanding.

Stop managing cultural differences: when you have enough diversity, let people be themselves rather than forcing cultural adaptation.

Invest in language learning early: six months of focused language study can unlock exponentially more opportunities than years of struggling without it.

Scale systematically, not rapidly: adding complexity through new markets or services requires thorough research and relationship building—shortcuts create problems.

Learn business fundamentals the easy way: formal education or mentorship beats learning through expensive mistakes, even for naturally entrepreneurial people.