Disrupting Japan is four years old, so we decided to invite a few hundred movers and shakers from Tokyo’s startup community over to have few drinks and to hear three of Japan’s most successful foreign startup CEOs talk about what it takes to succeed in Japanese when you are not Japanese.

Our panel included some of the most influential foreign startup founders in Japan.

We talk about strategies for growth, how to leverage your “foreignness” to your advantage, how to best manage multi-cultural teams, and what the future looks like for foreigners in Japan.

It’s a great conversation, and I think you’ll enjoy it.

On a personal note, thank you for reading and listening and for being a part of Disrupting Japan. When I started this project ago, I never imagined how large and influential the show would become, or how large and passionate the worldwide interest in Japanese innovation truly is.

I want to offer a sincere thank you to everyone who has pitched in to help make Disrupting Japan a success. There is no way I could have done this alone. But the best is yet to come. There is an amazing amount of innovation going on right now in Japan, and I look forward to bringing it to you.

Thanks for listening!

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A Special Note

For those of you who listened to the podcast know that the recording equipment cut out about half-way through the show. Fortunately, Jason Ball from Business In Japan was live streaming the show. Although the audio quality wasn’t high enough for the podcast, you can watch the whole show (minus a bit of Q&A) online.  Also, the transcript below represents the full show.



Welcome to Disrupting Japan, straight talk from Japan’s most successful entrepreneurs. I’m Tim Romero and thanks for coming out tonight. Now, you guys are awesome!

You know, actually, that’s exactly what I hear in my head every time I say that line. Now, for our listeners at home or wherever you may be in the podcast land, we got a special show for you tonight. To celebrate Disrupting Japan’s 4th anniversary, we are podcasting live from Super Deluxe in Roppongi with some of the most innovative people on the face of the planet, that is Japan’s startup ecosystem.

So, let’s everyone get their drinks together for a kampai, and listeners at home, feel free to drink along with us.

Over the last four years, Disrupting Japan has become bigger and more influential than I ever imagined it could be. Thank you so much for everything you’ve done to support the show. Thank you for listening. It’s been an amazing four years, and the next four years are going to be even better. So, kampai!

Audience: Kampai!

Tim: For these anniversary shows every year, we have a theme and this year, it is foreign founders in Japan, and on stage tonight, we have three – well,  I guess four fearless foreign founders who have taken very different roads to developing their companies here in Japan.

So, with introductions, on my far left is Jay Winder who has established MakeLeaps which is Japan’s leading SaaS invoicing system, and before that, you had another company, but I think a lot of you know Jay for running the Hacker News meetup here in Japan.

In the middle, we’ve got Paul Chapman, co-founder and CEO of Moneytree which is one of Japan’s fastest-rising fintech startups, and a true B2C SaaS success story in Japan.

Paul Chapman: Thanks, Tim.

Tim: And on my immediate left is Casey Wahl, CEO and founder of Wahl & Case which is a recruiting company which doesn’t sound that startup-y to begin with, but Casey’s also founded Red Brick Ventures which was an accelerator that spun out several startups. His company is deeply involved in artificial intelligence projects. And, you are now on the long hard march towards IPO. So, you’re doing something right.

Casey Wahl: That’s correct. Thank you.

Tim: Okay, I want to start this out on a positive note. So, I don’t know, I’m someone who’s on the firm belief there’s not real fundamental advantages or disadvantages; it’s just differences that you can take advantage of. So, what I’d like to lead with is, let’s talk about what advantages foreign founders have in Japan.

Jay, you want to lead that off?

Jay: Yeah, I think that’s a really good point you just made, Tim, where there’s good things and there’s bad things, and at the end of the day, you just have to figure out how to make something work, right? Actually, I think one of my favorite quotes about entrepreneurship that I think is really interesting is, “Entrepreneurship is the pursuit of a goal without regard to currently held resources,” right? And so, that means how much money you have in your bank account, it even means how much are in your current skillset, right? It even means how society is kind of currently configured right now. You’ll have advantages, perhaps, in some areas, and you won’t have advantages in other areas, and you have to understand those things and move forward the best way that you can at the end of the day. So, yeah, there’s good things and bad things and it’s your job to figure out the bad things and compensate or offset them.

Tim: So, what are the good things you got working for you as a foreigner?

Jay: Novelty, right? Like, if you turn up to a meeting, it’s like, “Oh, that foreigner, yeah, what’s he doing here?” It’s like, “Oh, he’s raising money.” It’s like, “Oh, hey, for what?” It’s like, “Oh, an invoicing company to help Japanese companies send invoices.” It’s like, “But, he’s a foreigner.” Honestly, that’s kind of a fair point, right? I am foreign, right? And so, for a Japanese person who doesn’t understand much about me or MakeLeaps, to think that somebody could come to Japan, understand all the intricacies of how Japanese companies communicate with each other to the depth where companies would trust that company to putting all their financial details, that’s a fair point. So, that’s something that we need to offset, right, by having a really solid team full of people that are really competent and have a lot of expertise and experience.

Tim: So, kind of just generates that curiosity and makes it easier to start the conversation?

Jay: Yeah, that’s right.

Casey: So, Jay, how did you get there? How did you get there where you can get between the Japanese companies where they, as a foreign founder?

Jay: Well, that’s a good question, Casey, I’m glad you asked.

Casey: Where they actually trust you well enough to do it, like what’s the advantage to get to that point? It’s a lot of discipline, I just know.

Jay: Sure. So, essentially, it is momentum, right? Because I remember, when you’re first starting out, you’re like, “Hey, I’ve got this idea,” like in Japan, people tend to use Microsoft Excel for managing their invoicing, and Microsoft Excel was released in 1982. So it’s not really like Microsoft Excel is like, traditional Japanese business software, right? Like, people just kind of adopted that and started using it for all sorts of different things in Japan. So, we’re like, “Hey, we’ve got a new way of doing things. How about this?” and people were like, “How about no? How about we just keep doing things the same way we’ve always done things?” like, “Well, I don’t know, okay, fair point,” right? So, from that point, you have to kind of go out and just get a first customer, right? Just get somebody to use the software, and at that point, you’re not even worried about how much money you’re making. It’s like, “Will you use this? Will this be interesting for you?”

Tim: While you were doing that, did you ever kind of play on your foreignness? Did you ever kind of say, “Oh, well, this is how they do it in San Francisco, and you should take a look at it for that reason.”

Jay: Not so much. I found what’s much more convincing is if you get some customers, get some momentum, get some user testimonials from them, and then say, “Hey, whatever you want to do is fine, but your competitor is doing things now with MakeLeaps, and they say it’s pretty good,” or you don’t need to be that direct necessarily, but, “Other companies are starting to adopt this and it’s giving them these benefits, so if you’d like to consider it, we’re very happy to give you a demo at your office,” kind of thing, and then once you got enough of that, it’s easy to kind of build off that momentum.

Tim: Casey, what about you? I mean, obviously, it’s an advantage when you’re selling to foreign companies, but when you’re selling directly to Japanese companies, does being a foreigner come with any advantages?

Casey: I think the novelty part there and the willingness that you can break rules and you don’t mind skipping out some of the processes that a usual Japanese salesperson would go through, you can go straight to the top a lot. Even when I was 25, 24, I can meet big company CEOs. I don’t think you could do that anywhere else, having been a foreigner here in Japan, but I think ultimately, kind of where we are with our SaaS products, is we need a Japanese sales team to kind of take it through. We’re kind of feeling that at some point, we have to hire this Japanese team to work through the Japanese processes, and being a foreigner is a disadvantage to go through large enterprise sales.

Tim: Paul?

Paul Chapman: I agree with Jay that novelty is useful. You speak Japanese pretty well, right?

Jay: Yeah. I think you speak Japanese pretty well.

Paul: I think I’m speaking English now, but sometimes, I can’t tell. No, but that helps, of course, if you could speak to people in their own language and even having a face like this, but everything else kind of more or less is familiar. So, from the way you hand across a business card, the way you bow, I mean, I learned how to speak and act like a banker from our senior advisor. The fact that we found him because I think we were foreigners and another foreigner introduced him to us. He lived in North America for 14, and I think the two other founders of Moneytree – that’s Mark and Ross. Ross is on his honeymoon so he’s not here tonight – we are the exact same age as his daughters, the three of us, so we’re the three sons he never wanted.  No, it helps. He sort of is kind of not having – we kind of started with a blank slate. He didn’t judge us for being this or being that, like, oh. I think when you come from overseas, you start with a clean record. And so, that’s an advantage, so people will meet with you, and so senior people will meet with us, but what we found was, they wouldn’t meet with us again, so I got to meet the head of SMCC six years ago, but I haven’t met anyone that senior at that company.

Tim: Oh, so that might be the novelty effect playing into it.

Paul: That’s right. It doesn’t really help you get ahead, it just gives you an interesting experience, like I was to go to my first  first executive lounge which is lots of big, old leather chairs, really long, you get tea. So, some of you guys know what I’m talking about, but in terms of the advantages of being a foreigner, I’m thinking differently because I think I have this in my own country because my family’s background is not like a long history in Australia. I’m the child of two cultures. So, if you come from overseas, you have two perspectives. Hopefully, you have two. If you don’t have the Japanese perspective, you don’t really have anything to offer. If you have the Japanese perspective for something else, then you can understand what’s good and what’s bad about both, and then you could start trying to bridge that, and that’s a unique skill that I think being a foreigner or being what they call a ‘third culture kid,’ you can do that.

Tim: There’s something I’m hearing here, and I just want to see if I’m hearing it right. It sounds like when you’re first starting out, when you’re a small company, you can really leverage the uniqueness of being a foreigner and the novelty, but as you scale up, that advantage becomes less and less, and you need to become sort of more Japanese. Is that in your experience?

Paul: It would have to be real. You can’t just – none of us get by on novelty alone; we have to deliver. We might get a shot at it because they think, “Well, give him a chance.”

Tim: But does the novelty scale up with the company?

Jay: No, in my experience. It’s a door-opener, essentially, right? But I think that as Paul was saying, once you show that you can speak Japanese, essentially, that’s a signaling mechanism. That’s saying, “Look, I get Japan, I get the culture, I’m not going to do anything crazy, right? You can trust us to deliver on the things that we promised to do,” so if you can show that, that’s what get you approved, like that’s what allows you to progress,  but the novelty thing might open a door, maybe not. Who knows?

Paul: So, just jumping in, one point there, so when we did our Series A around – we have to make a lot of bank investment committees because we got money from all three megabank funds. So, I think two years before that day, maybe three years, our chairman, Jonathan Epstein who’s in the crowd here somewhere – hi, Jonathan – he introduced us to someone who said if you got all three megabanks to invest, it would be amazing, but I have no idea how you’re going to do it. Just give yourself a lot of time, but when I was there, our jyokyuukomon basically, he did this thing that at the time, I didn’t know how to think –  I didn’t how to feel about it. I was a little bit in a state of  Japanese, a little bit conflicted because you say, “This is Paul and Paul speaks Japanese, Paul’s wife is Japanese,” he could have just as well have said, “Paul puts his kids in the bath, joining them every night.”

Tim: He can use chopsticks, yeah.

Paul: Yeah, I think he made me a fifth dan in IPO, and I got my fourth dan a long time ago. So, it’s been a while, so that was nice. I got a promotion, but the upshot was, he had to show them that you can trust him; he’s familiar. I’m going to match with him, so he acted as a trust bridge, but now, we’ve earned our own trust to an extent, and of course, we do everything we can to keep it.

Tim: Okay. Actually, along the same lines, so none of us have Japanese co-founders, and I know in my own experience, certainly early on around 2000 and such, when I was meeting with VCs, I would have tremendous pressure to have a Japanese co-founder or it definitely made it harder to raise money. It made sales harder as well, and so I’m curious, what’s been your experience? Have you had those questions? Have you felt those pressures and how did you answer them? Casey?

Casey: I don’t think I got the co-founder thing right anyways with – I did back a long a long time ago. Yeah, like really, no. So, I mean, we started professional services with recruitment, so we can become profitable pretty quickly and it’s a difficult business to scale, so you can kind of scale without a lot of VC money into there. So, only when we decided on the exits and we started to shift into HR technology in the last couple of years have I gone around to VC and yeah, none of them really loved me. I don’t know if it was me or it was because we have a recruiting company and recrutiting is  not that sexy or not many people understand HR tech, or not many people understand SaaS, or we have four different business lines and people don’t want to give them business lines.

Tim: As you started moving towards IPO, did those pressures, did you start getting the questions then about having a Japanese co-founder or a more Japanese control of the company?

Casey: Absolutely not. Actually, going back to the question about does novelty scale? It’s like, we’ve gone deep into this IPO process, but the novelty is definitely scaling, like there is not really many – maybe one foreigner that second founded in taken the company public in Japan, so as you start meeting with investment banks –

Paul: Is that Bryan?

Casey: Yeah. So, the only one but a lot of that don’t know, like most of the investment bankers around auditors, they’ve never really met other ones, so you get a lot of reaction and it’s kind of easier to hire people as well ., as you’re doing this, so I found that it’s an advantage in nothing.

Tim: All right. Excellent. Well, I mean, being able to stand up in a crowded market for any reason is an advantage. Jay, have you felt any of this pressure for Japanese cofounders?

Jay: So, to some extent, but I think that in Japan, if that is happening, you don’t find out about it directly, right? It’s just kind of like, “Wow, really interesting company. Thanks very much, we’d love to stay in touch with your progress,” you’re like okay, right? That could be for any reason it could be –

Paul: The long maybe.

Jay: Yeah, the long maybe, exactly, right?

Tim: Actually, believe it or not, that is progress. Back in I think it was 1999, I was not able to open a bank account until I had a Japanese cofounder.

Jay: Oh, wow, that’s crazy.

Tim: Not a loan, just a bank account.

Paul: That sucks. If you ever remember that I think until the late 1980s, a foreign entity needed a Japanese partner to own about half of company. I think China is still that way. So –

Tim: Yeah, passive aggression is better than active aggression.

Casey: If you can choose, yeah, that’s true.

Tim: You have to pick.

Jay: So, we talk about this a lot. Our network wasn’t very good so we just didn’t know anyone at the time who would want to take a risk, a chance on us, leaving some fantastic job to join this really tiny company six years ago, and the other thing is, I mean, just having a Japanese cofounder really helps in the early days, I imagine, because I haven’t done it, but that’s not really what you need. What you need is someone who speaks not Japanese natively, but speaks investor, so you need a CFO, and none of us were money people. Our chairman Jonathan was great. He had great network, met my first VCs, but took a really long time to kind of figure out how to get money out of them. He sort of turned them upside down and shook them by the legs. That didn’t work, but no, when we finally got a CFO who came from Goldman Sachs, he is Japanese, and having worked with GS and being a Japanese banker, I speak Japanese pretty decently, I don’t speak the language he speaks to investors, and if you’re a lawyer, you speak about the lawyers in a different way, and so that’s what you need, really is someone who can speak to that constituency, because I think it’s worth proving to some extent, if you speak Japanese and you’re not Japanese, you can make it work, but if you don’t speak investor and you don’t grow just purely organically from profits, then you’re not going to raise money easily.

Tim: Well, I think there’s also, there’s a legitimate concern behind that, especially before a startup gets traction, an investor wants to know, I mean, can you guys really sell in Japan? Can you really operate here? Especially on technology-focused startups. There’s a lot of foreign engineers who come to Tokyo, builds great software and I think VCs have a legitimate concern saying, okay, well, can you really operate? Can you really sell it?

Paul: They’re also secretly always wondering, is he going to go home? I kid you not.

Tim: I think so.

Paul: And you go to show them, no, I’m committed, I’m here. I was here on 3/11, that was actually three days before my wedding.

Tim: Oh, that’s a bummer.

Paul: Yeah, well, luckily, the reactor wasn’t so bad at that point, so I did get married, but no, when you tell them those stories, they’re like, oh, you’re in here too? Okay. So, I think that’s the thing about trust comes from shared experience and you need sharing and understanding. At the same time, the other things is, the Japanese startup ecosystem compared to other places is still fairly early, right? There’s still not a huge network of angel investors like there are in Silicon Valley that have kind of done everything and know the process, and I think that’s happening now, and once that happens and that’s also in Japan, things are going to make a lot more sense. You’re not going to be the outlier, you’re just going to be another person doing a company in Japan.

Tim: I think so, but also, I think that San Francisco is the outlier, so if you compare Tokyo to Silicon Valley, that’s kind of unfair. If you compare Tokyo to places like London or Berlin, I think Tokyo is actually more advanced. If you compare to places like maybe Singapore or Israel, less so but in the same lead. It’s just – you can’t compare anything to San Francisco.

Jay: Okay, well, since I made a comparison to San Francisco … –

Tim: It’s not illegal.

Paul: He needs another good one.

Jay: Yeah, perhaps try again. Well, I mean, I think it’s important to just take into account that the Japanese startup ecosystem is at a certain stage, right? And, once there’s a lot more foreigners that have done IPOS, like there’s only one or two right now. Once there’s 20, 50, it’s just not going to be a big deal, right?

Casey: It can still be a big deal.

Jay: Oh, well, yeah, sure.

Casey: I think kind of going back to my answer. If you can get an investment banker to join you once you’re scaling or kind of raising funds, or going towards an IPO, I think that’s just going to be gamechanger for you, right? If you’re a foreigner, it doesn’t matter, but if you have an investment banker who can speak very well to all the constituencies that they need.

Paul: I’d just to apologize to Jay for my comment before. But I don’t disagree with you. I mean, we all compare ourselves in this ecosystem to San Francisco and New York. London does raise tons of money in fintech and it’s like, there’s a lot of friendly jealousy. It looks so easy, it will make me so much money. The thing is, in Japan, we often look in – in particular, Tokyo because that really is a part of the VC ecosystem here. We compare ourselves to San Francisco, we compare ourselves to Tel Aviv – there is nothing similar between Israel and Japan in that regard other than we all like technology, but a country that we probably could look at as a good example that’s not so far away from us like San Francisco, I don’t mean in distance but in maturity, and so Stockholm, Sweden. So, you got Atomic, so the Skype founder and he’s putting a lot of money back in to the ecosystem through Atomic which is his fund, and then you’ve got a bunch of companies like Aquilno] which is a fintech unicorn. They seem to have that cycle going. We don’t have a cycle happening yet, and I think there’s a couple of reasons. There’s no M&A or there’s very little. Soracom 200 million by KDDI, that’s a huge improvement because before, the only thing you could hope for, I think it was web cache, what they got acquired by WebPay  for about  a billion yen, so $10 million. A billion yen, that’s like a billion cents.

Tim: We are seeing an uptake in M&As for sure.

Paul: But, it’s not at the point where those founders are now out and then going, “Okay, I’m going to put my money into the next generation,” and we need that to get it out of the cycle.

Casey: I see it a little bit differently. I’ve seen a lot more M&A happening in the last couple of years, and I just look at Kash, for example,  got bought for  $70 million cash, six months after launch, by DMM. I know that funders are putting a lot of money, and I know there’s quite a few funders putting a lot of money. So, I think the money is flowing a little bit more, but the point saying, there are still –

Paul: It’s early-stage. That’s really good to hear because without that, we’re not going to get that flywheel going.

Tim: I met three people before the show tonight that were involved with MNA in Japan, so it is – I mean, they didn’t tell me what their deal flow is like, but they’re out there – there’s interest. I mean, things are moving in the right direction.

Paul: I’m an M&A of venture businesses instead of big  IT …

Tim: Oh, no. Real startup M&A stuff, little startup MNAs.

Paul: OK. OK.

Casey: And I think the flywheel is still going to go. I think there’s more money going but it’s such a small start is where we are now, and usually, most of the founders have more than 50% in VC, typically want – Japanese VC want them to have a big person.

Paul: That’s another problem. I’m sorry, I don’t know if I should say greed, there are a lot of ungenerous founders in Japan and I think it’s not a case of them doing that intentionally. A lot of people don’t ask for stock options. They will happily break their backs working in a company and not get a lot of options. They should be asking for them, and the reason why is because it’s very binary. When the founder decides to put out cash, great. If they don’t, too bad, you’re out of luck, and therefore, no flywheel, but if one startup meets a few people with a couple of millions dollars to spend and thinking, “I want to put half of that money into the next generation and mentor them,” that’s a flywheel.

Tim: Yeah, I think we’re seeing the first generation of that right now, and the stock option thing is really interesting. Just from the founders I interviewed only like, three or four years ago, it was really unusual for a founder to be giving his staff stock options. Now, it is the norm. Not everyone does it, but it’s unusual if you don’t, and I think part of that attitude shift has been more and more startups that are being founded by teens, a group of people – so, it’s kind of this group from the start rather than the one great man who established the company and just everyone else follows him.

Paul: There is sort of a thing that probably most of you don’t see – I didn’t see it until I looked at my investment contract to Series B, and that was basically, sacho is seen as the company, and you’re handcuffed to it, and they don’t ask to lock anyone else in. It’s just you which is kind of short sighted because you need your CPO, you need your Chief of Sales, you need all these people who are key founders and you want to keep them for as long as you can, but I think it’s just an old way of thinking and it hasn’t caught up, but yeah, it does seem to be going in the right direction.

Tim: Okay, but actually, another thing, and this is just something that I’m going to break my own rule and compare us to San Francisco – it’s my podcast, my rules.

Casey: You’re vindicated.

Tim: Yeah.

Paul: No, the point still stands. It’s the correct points.

Tim: But no, even in San Francisco, foreigners have an oversized impact on the startup ecosystem. There’s a very large number of non-Americans that start companies in the US and Japan. I’m wondering, what are your thoughts on why that is? I mean, I’ve got my own but I want to throw that to you guys first.

Paul: Well, the pilgrim’s going to make it, and for that – sorry, at the risk of sounding insensitive, that really is the heart of the dream of startups and venture in the world. So, they all go to the Bay Area –

Tim: Well, I mean, it’s not just San Francisco; if you go to Singapore, there’s a very high percentage. The percentage of startup founders who are foreign is much, much higher than the population, and within Japan as well, foreigners make up 2% of the population, but probably, I mean, I’ve never counted, but 8% or 9% of the startup ventures.

Jay: Well, I think it comes down to incentives as well, right? Like, if you’re a Japanese founder, to some extent and I feel like we’ve all been saying this for years, like it’s changing, right? You can start a company people will be like, “Oh, okay, great,” but in America, that’s a high five situation, right? You’re starting a company? Well done, high five, that’s great. In Japan, there’s still a live societal aspect of, oh, you can get a real job. Oh, okay, well, good luck with your company.

Paul: That’s Japan and my mother.

Jay: Were they?

Paul: Four years here, four years here.

Jay: And so, I think as foreigners, we just don’t have that societal baggage. We don’t have that expectation of what we should or shouldn’t do, put honest by people around us, and so I think we have, to some extent, a slight degree more freedom to look at something that should be like this. I mean, at the end of the day, doing a startup is an extremely egotistical activity; it’s looking at the world and being like, that’s wrong. It shouldn’t be like that; it should be like this and I’m going to make it like this. I’m going to go out, I’m going to get a team together, and we’re going to change the world this way because it’s wrong how it is right now and it’s kind of if you’re a Japanese person, it’s sometimes like you accept society as it is a little bit, right? That it’s a little harder to kind of step outside that and make a change unless you got a lot of societal support, family support, and all that kind of stuff, so I think from that perspective, foreigners have some advantage to – yeah, from that perspective.

Tim: I think it makes a lot of sense.

Paul: More of us can read TechCrunch? No, I’m kidding. No, I think we see this with immigrants, right? And so, the question is, are we foreign founders, are we new Japanese? And Diamond had an article on this. It’s the only time I’ve seen it. They call it shinnihonjin. I read that and I kind of had these chills up my back because that’s what my parents got called in the 50s – new Australians. I’m Australian, and so Australia was a destination and is a destination for people to immigrate to, is Japan that? And I think we’re at this point in history where Japan needs it, and government policy is starting to say we needed them. Let’s look at Singapore, but I don’t think anyone wants to go to that extent, but at the same time, it has never really been done. A hundred years ago, after the Meiji restoration, they had a ton of engineers come out to Japan from Europe with bringing skills that didn’t exist, and most of them knew that they were all going to go back home, but are we going home or are we home? I mean, for me, is home Melbourne, is it Naka-meguro?

Tim: That’s an interesting question. I mean, I think my impression of talking both with founders and with government officials is that particularly the company founders and that type of foreigner, they envisioned coming to stay and building companies, and being here for the long haul, and I hadn’t heard the shinnihonjin term, and that is weird.

Paul: Well, we speak Japanese and my favorite gag is – well, I’ll say it in English for the benefit of the listeners, but it’s “Hi, I’m Paul.” I basically show them that I speak Japanese and all, but my face looks like this because people will say, “Oh, it’s true. You sound like you’re Japanese. If he was on the phone, I wouldn’t know.” That’s the greatest compliment because when I was 18, I’m like, “I’m going to speak Japanese really well,” and locked myself in my bedroom for 10 years and just studied, but my point is, it’s possible, and that’s a really new thing: can someone be – I mean, look at – sorry, I’m going to change the topic just briefly – Naomi Osaka, is she the new US Open champion? Is she Japanese or not? And so, I think –

Tim: Well, the Japanese are definitely claiming her.

Paul: It’s true. In Australia, we do that as well. You see your parents and bring them in, and say, “You’re Australian now, congratulations. Go win Wimbelton.”

Tim: Well, everyone does that. “Obama was the first Black president, full stop.” Don’t get –

Paul: No, but that’s just everyone. I mean, Money Tree, Wahl & Case, and many other businesses like  Make Leaps, we’re Team Japan. It’s just who we are.

Jay: That’s a good point, and actually, I think as well if you can go to advisors like the kind of advisors that you’ve gotten and as well at MakeLeaps, we’ve been really lucky to get some really fantastic advisors. Dr. Semoto, the guy the founded KDDI became our advisor which was a huge deal, right?  That was great, and when you sort of go there and say, “We’re here,” like you say for Team Japan, like Japan is doing things right now in a way that’s generating so much unnecessary work and it’s causing a lot of people to work 20 hours a day during their invoicing at the end of the month, and that hurts people. They should be spending that time doing other more productive things, so we’re here to try to do our best, to try to fix that, and I think if you’re somebody like Dr.Semoto], a high-level advisor, you’re kind of like, huh, okay, well, yeah, it seems like your heart is in the right place, so we’ll help you out. Okay, so – and then, you sort of become part of that system.

Tim: Alright.

Casey: Yeah, I’d say I’m kind of really curious how this is all going to turn out in like, 10 to 20 years from now because you’re saying  shinnihonjin, and I get the concept, but how many of us are really going to become Japanese?

Paul: I mean, when dual citizenship is a thing, I’ll do it because look, let’s put it this way: I have no plans to go back to anywhere by nakameguro, just talking about how I couldn’t imagine living anywhere else but nakameguro], it sounds really bad, right? But, the truth is, I have no plans to go back except for business trips every six weeks because we have a Sydney office. So, maybe I’ve made that possible at Money Tree and it’s good for the company, but ultimately, I don’t know either – will Japan accept us? Will this thing that we’ve been doing still be accepted and supported? I think it will, but I don’t know.

Tim: I think so too, but it is an interesting two-edged sword with greater acceptance, because I mean, Japan is a place that if you basically want to get along and follow most of the rules, and are a bit eccentric and do your own thing, and want to have people let you do your own thing, it’s a wonderful place to do that, but yeah, as foreigners become more common in Japan, there might be more pressure to behave properly.

Casey: That would be weird. How does it ebb and  flow, right? I think we’re having a wave coming in through Justia which is a platform we have to hire for startups. You see a lot of foreign engineers coming in.

Paul: Justia.io

Casey: Awesome, thank you. You see a lot of really good foreigners and we see a lot of really good product people coming in. I think you built this community of hundreds of people being here tonight, and this didn’t exist four years before and we got founders here, we’re going to have more and more founders, and as we actually start to have more of an impact in society and we’re not following all the rules out there, it’s going to be kind of the backlash in how this is all going to work. I think there’s question marks over this, but I think over the next few years, we’re definitely going to see a lot more for us.

Tim: Let’s bring it back to the present now because one of the things, almost the archetypal mixed team is, you end up with foreign engineers and Japanese sales staff which sure, that makes sense, but honestly, managing a company with mixed teams, I mean, it’s difficult. You have to spend a lot more time on communication, it’s less efficient in some ways, but other than just the access to a broader talent pool, do you think there’s advantages to having mixed teams? Are there more creativity? Do people think outside the box more? Is there anything like, any inherent advantages with mixed teams.

Jay: Absolutely. For a start, you have many different ways to look at a problem, much broader range of experience. I love the movie – I didn’t read the book – Moneyball, right? So, I clearly have some deficiencies in the eyes of most Japanese investors. However, I was able to get the trust of the senior advisor who filled that in for me. So, between me and him, we were a well-balanced founder and invested money, so he filled the gap. So, he filled the gap. Across the teams as well, the same thing happens. We have the CFO who’s never worked in IT but he knows a lot about IT now, but we filled the gap, we didn’t intend to teach him, he’s just very clever, but he filled that in, so a team is really made up of, even more so than a sports team because not everyone has to do – I mean, one or two roles, building and batting, and pitching. Across an actual company, it makes a lot of sense to have that kind of variety of ability. Also, right now, I mean, it’s no secret – it’s hard to get engineers or it’s hard to get project managers, it’s hard to get marketers, digital marketers – our digital marketing came from Berlin. We – I was going to say we imported him – we invited him to join us. He came on a plane in the sea – no –

Tim: And all your marketing is in Japanese?

Paul: That’s right. But digital marketing is digital marketing and it wasn’t like that six years ago that all the tools that everyone in Japan users: flyer, Facebook, Google AdWords, and it’s changed its name recently, Facebook, the tools are the same. The domestic tools have really mostly given way the tools that are made in like, Singapore or the Valley, or Tel Aviv, Berlin, and Berlin is a hotbed of talent for digital marketing, and so we get to take advantage of that. Now, on the flipside, it fills the team and a lot of the pure companies that are Japanese, so pure Japanese teams, when they start thinking, “You know, we need more people to help us.” You know what they’re doing? They’re going to Vietnam and setting up shop there, but what we’re doing is I think much more efficient. We’re bringing the foreigners here or hiring them here which means we’re much closer to the customer and that makes the communication overhead lower, it means we can move faster. If you outsourced to Vietnam or to India, you have the same problems with that – they’re too far away from the actual users.

Tim: Yeah, and even bringing everyone to one place means you’ve got one team.

Paul: That’s a big advantage as well. The challenges come from managing everyone’s expectation, and I imagine my job these days is, other than just hiring people and finding good people, I have this big wrench and an oil can, and I’m running around oiling the machine, and whenever it goes clunk, clunk, clunk, clunk, clunk in one area, I have to run there and do something. Otherwise, I stand back and let them do the job, and that seems to be the role, but with the foreigners, there’s different problems with the Japanese stuff. My CFO has really been saying, he says, “Look, just because someone’s allowed not Australian –“ and I think he’s talking about me – “Or American –“ he didn’t say that, no. He said, “If they have a big voice, they’re going to be heard in the end, but we have to give a megaphone to the Japanese staff so that their voice will be heard, and so we tell everyone that, so that way, they know they can come to us. We get sometimes, a bad channel because people often don’t like confrontation. Sometimes, it’s not bad at all; it just depends on the person, but that’s our policy, so we call ourselves a foreign global company in that we are not a multinational company, we’re not a foreign company, and we’re not a domestic Japanese company, but we are a Japanese company.

Tim: Jay, you guys are about half- foreign, half-Japanese, are there any intrinsic advantages to multi-national, multi-cultural thing?

Jay: I mean, I’ve never ran a company that wasn’t fairly multinational, right? So, it’s hard to compare it to anything else, but yeah, like yeah, I mean, it’s nice to have a diversity of opinions and different set of approaches to problems, but yeah, I guess build a team to also much more easily go international at some point as well. If your team is already configured like that, that’s a huge advantage for you at some point when you want to do that as opposed to starting from scratch, so I think a lot of Japanese companies, and I don’t know how successful this has been but they’re like, “Okay, now, the whole company works in English, but now, we have an important meeting –“

Paul: Rakuten stopped that.

Tim: Yeah, usually, it does not work out very well.

Jay: Yeah, it’s hard, right? So, it needs to be built into the – well, it’s much easier for it to be built into the organization from an early stage and that gives you a lot more places to go.

Paul: Make Leaps is a Japanese-English, both equally, or more or less interchangeably.

Jay: More or less – it just depends on the groups of people that are talking to each other and meeting each other. So, yeah, generally, everyone speaks Japanese very well, but yeah, we have no particular kind of on-high dictation. You have to speak this language.

Tim: No official language. You guys have an official language?

Casey: English. We have 19 nationalities, there’s all kinds of conversations going on …

Paul: I think you helped place someone in one of our companies. We have 20 now.

Casey: Wow! We have to get some more in there.

Paul: Yeah, we better get off your ass on that.

Casey: But I think Jay’s putting a really good – and as a foreign founder here, once you, I guess overseas, but in the early days, we were confronted with the default thinking of the product space we were in, which in our case was personal finance apps, and in Japan, it’s a very specific thing, and these days, it includes taking a photo of a receipt. We’ve had a lot of arguments about whether we do that or not, but ultimately, we built kind of a millennial app for Japan where there’s only half as many millennials as in the US, percentage, and on top of that, we ignore some of the – what I would now call market requirements. Basically, there are some things there are some things where regardless of how much we push the envelope in this market, they always want you to do this, and I think a lot of foreign companies make that mistake and for us, we were sort of starry-eyed: “We’re going to change all this stuff,” but building to what we though was an international standard, it made it harder to succeed because it was more because usually, something succeeds in the US, then they bring it to Japan, and the first thing that they could say is push the envelope.

Tim: But in some ways, it’s sort of similar to the effect of having a foreign founder because you are doing something different and it might – little different and take more explaining but will get that interest and you will stand out for it.

Listen, I’ve got time for one more question before we wrap up and after that question, we’re going to have a Q&A session, so if you want to have questions to ask, you can line up right over there. We’ll get to you in just a minute.

So, our last question is, I want to ask, what is – and this is probably the question I get asked the most by fans of the show, a lot of my listeners, and what is the best advice you can give to foreigners who want to start a startup in Japan? It could be about anything, but what is the most important thing you’d say to them?

Casey: And Japan being the key component here, right?

Tim: Japan being the key component.

Paul: Don’t –

Tim: No, no, I wouldn’t say.

Tim: No, no, I make the same joke all the time, but –

Paul: I would say don’t do it lightly, don’t do it lightly.

Tim: What do you mean?

Paul: Well, we all suffer from fatal optimism as founders. I mean, Japanese, non-Japanese, we’re like, Jay said –

Tim: I’m going to change this!

Paul: Then go do it. Don’t do it lightly. You are not going to be the great white or the great non-Japanese hope, you will have more of those than you expect but less probably less than what we went through because time has marched on. I would say that do it if you really, really, really believe in doing something not just to change the world and not just to make a business but to do something good for Japan. People will appreciate that and that will come through in what you do. If you don’t, you might as well do it anywhere else, maybe  Stockholm – they speak English there really well and it’s a great ecosystem. Do it in San Francisco. Here, being a foreigner, on the whole, it is not a big gamechanger, right? But everyone starts from where they are, so if you’re a foreigner, you can’t easily even if you naturalize. So, if you really feel you want to do that, like I think Jordan from Zehitomo is here with I spoke with him earlier today, so he’s doing something really cool, so he’s introducing people to people who provide direct services, and – sorry, for giving a free plug – and that’s something I think that people understand: that’s helpful for Japan, that’s helpful for people who are unemployed, it’s helpful for matching out people and getting rid of the middleman which seems to just take money, not provide a service which is maybe not a fair way to cast it, but that’s a pro-social startup. So, if you’re a pro-social startup, like most social gaming companies, then you will definitely have people who will say, “I like what you’re doing. I’m going to go out of my way to help you,” and then that can snowball.

Casey: I’d say in Japan, it’s a slow market. It’s a relationship-driven economy, so you have to be in it for the long haul and it takes a lot of time to win a Japanese customer, but they’ll stay with you for a very, very long time, and even if you make a mistake and you’re willing to apologize, they don’t just say it but there’s not any exits; the road to IPOs have at least two years if you get everything absolutely right at that point, and it takes a long time to build all that. So, I think you have to be all in like Paul said, and I met a lot of foreigners that have started companies and they don’t want to take a bank loan of a sizeable amount because you’re liable for this, and I think if you have that mindset, you’re probably not going to build something here, so I think just do everything is what I would say with a long-term horizon.

Jay: Yeah, I agree completely with that. I think in general, the sunny, broader point is, I don’t think you should start a company unless you absolutely have no choice, right? I’ll explain what I mean by that, right? Some people, I think, try to be an entrepreneur for a career choice. It’s like, “Oh, I saw it on Tv. Oh, Shark Tank, that’s interesting, I’ll try that,” right? And you sort of – some people kind of try to do that, but if you have a problem that you cannot stop thinking about, that you just think – you’re thinking about it all day, then you go to bed, and you have a dream about that, and then you wake up thinking about it, you just have no escape from it, then you should start a company because that kind of motivation on drive is your eye on the horizon; it’s seeing the future and how it could be, and unless you have something like that, there’s a lot of adversity in doing a startup and sometimes, it’s pretty difficult, right? But if your eye is on the horizon, it doesn’t matter what happens day to day, it doesn’t matter if you have a setback or a problem, or an issue because your eye is on the horizon of you can see how it’s going to be once your startup comes to fruition and once the world has changed in the particular way you want it to be changed. So, to tie that to – once you’ve got – that trust and momentum, it’s a train – it’s much harder to stop once you’ve taken off.

Tim: And really, that’s two sides of the same coin: the difficult in getting the customer the first time is like mathematically equivalent to the ease of keeping that because it’s just as hard for them to change to a new vendor from you as it was for them to change from their old vendor to you. I think it’s really interesting that we’re all giving very similar advice, and I expected a big variation, but I think this just emphasizes how incredibly important this is, and really, my advice is quite similar as well with one caveat. So, it does take a long time in Japan, but there’s also this kind of mythology that’s build up around sales here that it’s some mystical process and that it takes years of relationship-building and you just never know until you suddenly make a sale – sales don’t work like that here. They move through the same logical processes in Japan as they do anywhere else, just takes a little longer, and the direct advice I would give to anyone who wants to start a company here, it is not only be willing to wait, but be willing  to put your time into the ecosystem, to give to that industry community for a while before you expect to see results. So, whatever niche you’re stumbling into, show up to the meet-ups, not to push your product on anyone, but just to be there – to meet people and to introduce people, and then amazing things do happen, but it does take longer.

So, well, we got to kind of wrap up this part of the show, but we’re going to have Q&A immediately, so if you got questions, please step to the mic and while people are getting your questions ready, let’s have a huge hand for our panel tonight.

Alright. Questioner number 1, step on up.

Bob: Thank you, all. Thank you, Tim, for this platform that you created. The guests, you’re obviously up here because of the things made, things you’ve built, but I’m really interested to know what was the first major lesson you had, the first big failure? I just like to get a feel for each.

Tim: You mean like a personal failure or business failure?

Bob: Business failure that was the most valuable lesson for you, unless this was the thing that you’ve achieved, was the first thing and I don’t think anyone really becomes successful the first time around.

Tim: Well, I’ll throw mine out there. Biggest mistake I made was kind of a combination of personal and business, and it was kind of – I didn’t realize that nobody really cares about my vision. I mean, for its own sake, so what I created what I considered to be an amazing software and I couldn’t understand why no one else wanted to use it, and it took me a while to realize, like no, it’s not about me. It’s about them, and so it took me a couple years to get my head around that and once I did, success came – I don’t want to say easy but easier, so that was my biggest failure.

Casey: Of course, if you’re still standing, you haven’t really failed in the end, so just keep going, but I think the first thing that I did wrong was I set up the initial team wrong – it had a family atmosphere and I don’t think it should be a family atmosphere in a startup or actually, really any business situation. It should be a team and a high-performing team, and everybody knows what all the members are accountable for,  but in a family, you’re going to have members that don’t show up or whatever.

Tim: Pretty much like a sports team.

Casey: Exactly. I think we’re all going it alone, we’ll take care of each other, and this is great but there’s a lot of low-performing people, people are going in different directions, how to clean it all out to replace them with a team, and I would recommend you don’t do that.

Paul: In my experience it might feel like a family atmosphere but it’s not, so even if I’m doing it – if I’m doing a bad job, and I’m sure people would let me know. I would say my biggest failing was my first startup when I was 23 which I started in – I come through the startup ecosystem in Australia. That’s a long time ago, and I chose – well, we all chose bad co-founders who were not right for each other. It’s a bad marriage and it was very, very messy. There were four of us. We two knew each other well, the rest of us didn’t really know each other that much at all. We’d all gone to the same schools – University of Australia, and that put me off startups for many years, and then I came back and found the people that I was working with here, and I said, “Hey, let’s go do something else,” and actually, they said – I remember having this meeting in Roppongi when I was trying to convince them to do Moneytree because we’ve been doing apps, and I said, “Paul, we want to know, would you do Moneytree without us?” My friend’s response was, “What makes you think I would not do Moneytree?” and we’re still talking about that today.

Jay: Okay, so what I would say is my biggest mistake is I think really not deeply understanding the concept of leverage, right? So, my first company that I did was a services company where we had engineers who went down on site and the issue with services business is to some extent, it’s very difficult to scale them. Even if you get successful and you get a lot of business, you have to then go out and hire 10, 20, 50 people, and then if that client goes away for whatever reason, then you have a big kind of issue. So, yeah, once I kind of really clicked onto the idea of how powerful leverage can be with latest available practices and technology, and software, that set the stage from being able to create a software company like Make Leaps and yeah, that was a huge quantum leap.

Tim: SaaS is the way to go, for sure.

Jay: SaaS is the way to go, yup, absolutely.

Tim: Okay, next question.

Quest 2 : work for insurance company, 140 years old which is very conservative. Can you share with us what was something you did, or something that worked, that  moment you broke through the barrier  to client to change, like go to talk with CEO or something?

Tim: I’m going to – please talk to me after the show because I’m actually working with a number of companies on exactly this, but I’m going to keep my answer short because there’s a lot of people who are waiting, but I’d say that all sales, whether you’re selling to an enterprise or you’re selling to a one-person freelancer of all sales with personal, so it’s still selling to what that one person wants, whether he’s worried about his boss judging him or he’s worried about whether his competition is doing something first. It’s enterprise takes longer but it’s fundamentally the same – you’re selling to a person, not a company.

Casey: So, we have our latest SaaS product, it’s called Atune is AI for hiring organizations and team construction, and what we had found is actually, Japanese large companies are pretty sophisticated buyers, like they do a lot of research, they know exactly what’s out there, they’re very interested in your products, and they’re quite happy to take you along in the process, but I think the key switch where we’re happy to talk to them and there’s a novelty being a foreigner with a product that they’re interested in, in Japan, but as Tim said, we need a Japanese senior level sales person to take it through the whole process, but it just can’t do it consistently as forieners.

Paul: I don’t think you necessarily need that super senior guy, like you would have said, “Oh, it’s the senior guy, it’s going to do.” For us, we keep selling it until it’s sold, and selling this would be talking to them, hearing their problems, trying the te-an process and it’s a Japanese company and it’s endless tean until the end and of course, it’s like, “Oh, I have this idea. Let’s take it to them,” and then that champion takes it to their bosses and then they bring it back with some problems, and we fix the problems, we take it back to them, and this endless cycle of proposals, and at some point, we have to decide is it going to close, or we pull our resources back and leave it for a while. So, it’s a good sales process, but it’s elongated its time, so to give you an example. One of our clients is a big credit card issuing group – some people will know who that is – it took two years to close the deal and it was one of our biggest deals ever because their app is built on our platform. So, every one of their app users has to become Money Tree account holder because we’re a financial debt aggregation platform. We’re not just an app. It took two years, but it was worth it, and we didn’t have a super senior sales guy going in there. We didn’t talk to the yakuin, the executives, but we went through the normal process through normal channels. If you go to the senior guys, it can backfire as well. Of course, it worked, but just more time.

Jay: I don’t know, I think in any startup, there’s always various inflection points, but I think through Make Leaps, the biggest inflection point was one day, the phone rang and this guy said, “Hi, I’m also running kind of a cloud invoicing company and we just got bought by another company, and so the company that’s buying is has decided to shut down the cloud invoicing part and we’re looking for somebody to take on all of our customers.” We’re kind of like, that’s awesome].

It sounded great, but  well, okay, do you need my bank account details too? It just sounded like too good to be true, right? It’s like a scam.

Paul: I need iTunes gift cards.

Jay: Exactly, yeah, yeah. As quickly as possible. So, we had a meeting with that guy and he came into the office and said, “Yeah, it sucks because I spent the last two years putting my reputation on the line by selling to all these companies, and now, I’m just trying to find a soft landing,” right? Which I was really impressed by, right? Like, that kind of thing is really, yeah, it’s unique in some ways to Japan, I think, where it sort of feels like that’s going to be more common. So, anyway, he sort of said, “Look, we’re at the moment comparing between MakeLeaps and a huge Japanese system integrator, and we noticed that MakeLeaps, you’re missing these five key features, so we’d probably give the big system integrator, the big clients will give MakeLeaps the little clients,” and we’re like, “Oh, my God, if we do this work, if we build these features, we want all the clients.” It’s like, “Yeah, well, okay, well, I have a meeting with them next week, let’s see how it goes.” I was like, “Do you have the list of features?” He’s like, “Yeah, sure.” So, I was like, “Okay, cool.” So then, I kind of ran back into the development section of the company. I’m like, “Hey, guys, I’ve got good news and bad news. So, the good news is, we could just double our customer base, get these really great customers. The bad news is, here’s the five features we desperately need by the next meeting. It’s Tuesday. What do you think?” They’re like, “Let’s do it! Let’s do it! Whoo!” So, we worked the whole weekend, right? And then, the guy came back in for the meeting on Tuesday and he sort of said, “Okay, well, thanks for your time again.” We’re like, “Okay, we’ve done these features. We’ve done this one here, we’ve done the front-end design for this one, this one, there’s a lot of stuff that still needs to be done, but this is basically what we’re thinking, is this kind of what you needed?” He’s like, “You did this over the weekend?” It was like, “More or less.” It’s like, “Oh, okay. Well, I met the big Japanese system integrator yesterday and they’re having a committee meeting to decide whether or not they’re interested to take on this project, and since you’ve already done all the features, you know what, you seem like you know what you’re doing, we’ll just give it to you,” and so out of that list of customers came Rakuten, and Rakuten then became a customer, then they became a partner, and then they became our investor for our Series A kind of round of funding. So, that was a huge inflection point for us.

Tim: Thanks so much.

Tim: If we are super efficient, we can do two more questions, so step right up.

Guest 3: I’m pretty sure you guys have big troubles, like clash with the banks or employees, or investors, or I think co-founder, and I was wondering, because you’re in Japan, how do you manage these kinds of clashes differently than if you were in your home country?

Tim: I’m going to give a more general answer to that. I think Japan, more than the US which is the other kind of business culture I really understand, personal reputation counts for a lot more in Japan than it does in the US. It’s when you sell something, when you go into business with someone, you’re kind of either explicitly or implicitly putting your personal reputation on the line for that deal. So, disputes have to be handled behind the scenes. Any drama is not helpful to anybody, but quite honestly, of all the problems that I’ve had over the years, it tends to wash out in the long run. You don’t remember the problems, especially I guess if you handle it behind the scenes, but yeah, that’s my approach to it.

Casey: Yeah, I think if we don’t forget our problems, we couldn’t keep going, right? Like, just step on up, but I think  like when you’re clashing, it’s because you have different values, okay, your intrinsic values that you have are going to be different than other members of the team. It doesn’t matter across cultures, but kind of specifically to Japan, and this kind of goes back to the stock option conversation that we had before, I’ve been seeing founders giving shares to people early on in the company and it’s very hard to get those back, and they’ve gone and moved. on like that and because the exits are so slow in Japan and you can’t rely on them and they had all, that’s why a lot of Japanese founders don’t do it because there’s all kinds of horror stories of a lot of equity sitting outside of the company, they’re not aligned with your interest, so how do you handle that? I think you have to do that very delicately in Japan, as well and more so

Paul: It’s in the shareholder’s agreement. So, don’t let them exercise their stock options until there’s an exit event, so that you never have all these shareholders that used to work for you and they don’t like you anymore, or just disagree –

Casey: That sounds like good advice.

Paul: I had a good advisor.  No, but I mean – so, would I do it differently? I am doing it differently. My first startup was not an good experience, it was tough to get out of it with my stock – I was the CTO, I was 23, and I was bought by Thompson Reuters which was cool, but it was an Australian company so very small, and I vowed that if I ever did that again, so I chose good co-founders as I said in that previous story, but ultimately, if you start a company here, you will change because of it, but you’ll change differently if you compare yourself to starting in another company because the environment’s different. It’s different environment, different experiences, you’ll be different. I think as Tim said, you don’t air out your dirty laundry; you do it in private and this definitely a greater sense of not having a tantrum in public in Japan than say, Australia or America, maybe France, I’m not sure. Ultimately, you have to be a better version of yourself every day, you have to be good enough to keep – if you’re a founder – to keep running the company that you’re building because one day, it will be better than you are if you’re not careful. So, hang on it differently –