The Challenge for an AI English Conversation App:
Creating a Language Acquisition Technology to Globalize Asia
In this final part of our three-part series, we look back at the greatest crisis SpeakBUDDY faced in its 13-year history.
President Tateishi shares how he navigated a dire situation, with only three months of runway left, by being brutally honest with his employees. We also discuss the company’s unique organizational culture, where a multinational team of over 10 nationalities balances autonomy with discipline, and explore his grand vision for leading Asia’s globalization. Finally, we reveal how their partnership with D-POPS GROUP is accelerating SpeakBUDDY’s ambition to become a unicorn company. (This interview was conducted in January 2026.)
See Part 1 and Part 2 of the interview here.
◆Understanding How Long a Year Can Feel to an Entrepreneur
Sugihara:
It has been exactly 13 years since you founded your company. During that time, you’ve navigated various shifts, including the COVID-19 pandemic. Looking back over these 13 years, what were the major turning points or obstacles that you encountered, both personally and as a company?
Tateishi:
While the company was founded quite a while ago, for the first three years, I was developing non-AI English learning apps and operating solely on my own personal capital. The situation changed dramatically around 2016, when we pivoted fully to AI-driven English conversation and began receiving investment from venture capitalists.
In that sense, it has been a long road. One thing that surprises you when you become an entrepreneur is that one year feels incredibly long. You’ve likely heard of Janet’s Law, which suggests that time feels like it passes faster as you get older. By my seventh year at the investment bank, my colleagues and I would often say, “This year is already almost over!” I think that happened because I had mastered most of my tasks, the work had become routine, and there were fewer new stimuli.
However, when you start a business, new challenges appear one after another, day after day. Each time, you have to acquire new skills or come up with fresh solutions. This density of experience makes a single year feel exceptionally long. Doing that for over a decade has been a very lengthy, yet fascinating process.
Regarding the COVID-19 pandemic, AI English conversation benefited a lot from the stay-at-home environment at first. However, as the period of restricted travel dragged on, Japanese people sadly stopped studying English. With no business trips, no international visitors coming to Japan, and no overseas vacations, their opportunities to think about English virtually disappeared. The entire English learning industry slumped, and it was a very difficult time for us. Fortunately, demand has now fully returned.

◆The Ultimate Crisis: An Honest Confession with 3 Months of Runway Left
Sugihara:
Of all the situations you’ve faced over the years, if you had to pick one, what was the biggest hurdle? And more importantly, how did you manage to overcome it?
Tateishi:
It was undoubtedly the period during the lead-up to our funding round, when our runway (the time left before we ran out of cash) was nearly gone. In a startup setting, you’re constantly accelerating hiring to fuel growth. When the pressure to raise capital hit at the same time as the need to keep the organization unified, it was incredibly intense.
Developing AI services is a marathon. At first, the tech can’t quite match human performance, so you go through years of not being able to amount to much. But then, you hit a tipping point where the AI suddenly starts outperforming humans, and growth just takes off. 2019 was that turning point for us, and it was also our hardest year.
We were right on the cusp of our Series A, but we only had about three months of cash left in the bank. I was running myself ragged trying to secure funding, while the team seemed—at least to my eyes—a bit too relaxed. Eventually, I couldn’t bear the stark contrast between my stress levels and their composure any longer.
Until then, I had kept our financial numbers and cash flow concerns private because I didn’t want the team to worry, but I had finally hit my limit. I called everyone together and told them honestly, “This is exactly how much cash we have left, and this is how much we burn every month. If you do the math, we have three months. Our payday is the 25th, so I can pay you this month, but three months from today, I won’t be able to pay you any more.”
I knew the risk that everyone might jump ship. But I couldn’t keep going with that emotional disconnect, so I decided to put all the cards on the table.
While one person did choose to leave, the remaining ten members said, “Let’s find a way to push through this together,” and they really worked hard. That moment erased the inconsistency I had been feeling, and seeing them commit gave me the courage to keep going myself. First, I went to my former boss and humbly asked for a bridge loan to extend our runway by another three months. Then, during those three months, a new feature we developed became a massive hit.
Our KPIs skyrocketed, and revenue went up as well. People started telling me, “Since you’ve come this far, I’ll throw in my investment.” We successfully raised about 300 million yen in our Series A. That was the most grueling time of my life. Since then, I’ve made it a point to share the details of our company’s expenses and exactly how much cash we have on hand.
Sugihara:
By doing that, I imagine the employees feel like they are truly in the same boat.
Tateishi:
Exactly. At the end of the day, you can’t reach the same decision if you don’t have the same information. I believe that if you make that information open to others, you’ll eventually reach a shared understanding.
◆A Team of 10+ Nationalities: The Strength and Struggle of True Diversity
Sugihara:
SpeakBUDDY is a remarkably global company. About a third of your employees are non-Japanese, representing over ten different countries. What are the benefits of this multinational team, and what challenges have you faced?
Tateishi:
It’s a bit of a chaotic mix, ha ha. ‘Diversity’ sounds great as a buzzword, but in reality, managing it is incredibly difficult. Everyone has different perspectives and values. It’s a constant challenge to keep everyone aligned.
However, the upside is that it naturally brings in ideas we never would have had otherwise. We can flexibly adopt global best practices and viewpoints that aren’t bound by Japanese common sense. Plus, since we are a language company, many of our Japanese hires join specifically because they studied English and want to work in an international environment. For them, working in a cross-cultural team is a source of genuine professional fulfillment.
From a management standpoint, it’s a huge strength. For specialized roles where the domestic talent pool is small, such as engineers and designers, widening our search to include global talent allows us to hire elite performers. Although, running all-hands meetings in both English and Japanese with simultaneous interpretation can be rough, ha ha.
◆Encountering D-POPS GROUP
Sugihara:
You recently attended our business briefing and social gathering. What were your impressions?
(Click here to read more about the event.)
Tateishi:
I was primarily struck by the sheer number of people in attendance, since they were all executives! It made a deep impression to see leaders of that caliber listening so intently to our story, asking sharp questions, and offering collaboration ideas on the spot.
During the formal briefing, I felt a bit of a distance, but once the drinks started flowing at the social gathering and we got into our personal stories, I felt like I was immediately accepted as a companion. I really felt that D-POPS GROUP is a company with a strong family vibe.
Actually, we have a new feature currently in the R&D stage that hasn’t been released yet. When I shared the idea at the briefing, the reaction from the audience was overwhelming. Afterward, our Executive Officer Morimoto and I were talking about it, and we’re pretty sure that idea is going to be a hit. Having that kind of validation from a room full of entrepreneurs gave us the confidence that we’re heading in the right direction.
Sugihara:
SpeakBUDDY already has many supporters and investors. Why did you decide to accept our investment, and what has the experience been like so far?
Tateishi:
The biggest reason was that President Goto, and you as well, really listened to us with such sincerity. It made us really want to grow alongside you. D-POPS GROUP is a very unique organization, and there are many elements of your company that make me think, “This is the kind of company I want to build.”
When we were raising the funds, I told my team, “I want entrepreneurs whom I truly respect to become our shareholders. I want us to aim to become a company like D-POPS GROUP, so I absolutely want to accept their investment.” My thoughts at the time were, “I want us to learn from you, so please invest in us!”

◆Building a Great Company that Balances Autonomy and Discipline
Sugihara:
Regarding our company’s aim of realizing a Venture Ecosystem, are there any parts of that vision that resonate with you?
Tateishi:
Above all, I deeply resonate with your commitment to developing unicorns. To be honest, I’ve never been the type of person to put stickers on my laptop, since I always felt, “I don’t want to ruin a machine that I’m trying to keep clean!” However, since the D-POPS GROUP unicorn sticker has a genuinely cool design, and more importantly, it serves as a constant reminder of your ambition for us to reach unicorn status, I decided to put that sticker on my laptop.
Sugihara:
We really appreciate that, especially since you don’t even put your own company’s stickers on it, ha ha!
Now, where do you see SpeakBUDDY in 5 to 10 years?
Tateishi:
Over the next five years, our vision is “to become the AI language acquisition startup driving Asia’s globalization”. And in ten years, we want to fully realize our mission: “Open a world of opportunities by achieving true language acquisition.”
Lately, one thing I’ve been consciously trying to pursue is “to build a truly great company”. This may be an abstract goal, but I want SpeakBUDDY’s very existence to make people say, “I’m glad this company exists.” To achieve that, I feel like we really need to return to the roots of our mission, vision, and values.
Organizationally, we spent the last year significantly strengthening our discipline. Startups are often free-spirited, autonomous environments, and we ourselves operate on a hybrid model centered on full-remote work. I’m personally someone who didn’t originally like to create rules, but as we grew past 60 employees, errors and accidents inevitably started to occur. So, I decided to steer us toward a culture that strongly asks for discipline and accountability.
I recently read that “only by balancing autonomy and discipline can one create a great company”, and it struck a chord. Autonomy without discipline is chaos, but discipline without autonomy is stagnation. I want both at a high level.
Sugihara:
Autonomy and discipline seem like opposites, but they are actually two sides of the same coin. At companies like Google, the environment looks free, but the governance and the focus on achieving goals are incredibly intense. You are free to choose how you work, but you are also held totally responsible for the mission. Both aspects co-exist.
Tateishi:
Very true. That’s directly related to the recent moving of our office and us paying closer attention to the culture we’re building.
◆From Asia to the World: Leading Global Integration
Sugihara:
Do you have concrete plans or an outlook for expanding into the market in Asia and the rest of the world?
Tateishi:
We do. While we’ve temporarily paused our efforts to enter the Taiwanese market, we’re looking at opportunities to move into East Asia first, followed by Southeast Asia. Ultimately, we want to expand to Europe and the rest of the world.
Sugihara:
Right, since Southeast Asia alone has a population of over 600 million.
Tateishi:
It is a remarkably attractive market. There are billions of people worldwide struggling with English, so we want to provide our services to them, for sure. First, we’ll focus on succeeding in Japan, and then scale up from there.
◆A Message to Readers: “A New Way to Master English”
Sugihara:
Finally, do you have a message for our readers? This column is read closely by executives, entrepreneurs, and investors who have a real eye for professionalism.
Tateishi:
Everyone can feel the staggering pace of AI evolution every day. In an era like this, I believe we are being asked to question traditional methods and try something new. For English learning, too, I encourage everyone to try different methods from what you’ve done before.
At the risk of sounding biased, I believe English is only going to become even more important for business professionals as AI makes international collaboration easier. We are seeing an increasing number of young people for whom English fluency is a given. We hope the professionals currently leading our industries will also take advantage of SpeakBuddy to brush up on their language skills, develop their own unique English style, and not get left behind by the younger generation.
Interview conducted by D-POPS GROUP’s advisor Genta Sugihara.
SpeakBUDDY, Ltd.
President and CEO: Tsuyoshi Tateishi
Address: 3F +SHIFT Nihonbashi Sakuradori, 3-14-3 Nihonbashi, Chuo-ku, Tokyo
Established: May 2013
Website: https://www.speakbuddy.com/en
