Jason came to Japan from Australia to study martial arts, and his company MakeLeaps is now kicking ass in online invoicing. Jason bootstrapped MakeLeaps himself and he and his partner, Paul Oswald grew the company organically,  acquired two of their domestic competitors, and recently became the first Japanese company to receive funding from an AngelList syndicate.

Jason and I sat down over way too many beers and talk about what life is like for foreigners who start and grow a companies in Japan.

Show Notes

  • How to identify a promising niche market in Japan
  • Japanese “invoice culture”
  • Fundraising strategies for Japanese startups
  • How to buy-out your competition even with limited funds
  • The best way for foreigners to sell effectively in Japan
  • How to turn a terrible work situation into a successful company


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Tim: Welcome to disrupting Japan straight talk from Japan’s most successful entrepreneurs. I’m Tim Romero and thanks for joining me.

Today I sit down with my friend Jason Winder of Make Leaps over frankly way to many beers and the interview gets a little silly near the end of it but you know that’s where all the best conversation always happens. I’ve been a friend of Jason’s for more than 10 years. I’m an investor in his company and drunk or sober, he’s always a fascinating guy to talk with. His company Make Leaps is fundamentally changing the way that Japanese companies do invoicing and that is a huge thing here in Japan, as Jason explains.

We’ll also talk about some of the advice he has for companies that are just starting up in Japan, how the sales process is different in Japan and outside Japan and he gives some advice on how to grow a company, via acquisitions even as a small startup run by a foreigner and news was released shortly after we recorded this that Make Leaps has become the first Japanese company to be funded via an angel list syndicate. So we’re expecting great things from Jason and Make Leaps, so let’s get to it.

== Interview Starts ==

Tim: So Jason we’re here in your office next to the beautiful Meguro River.

Jason: It’s a gorgeous, gorgeous river especially in the soccer season.

Tim: Actually it’s true in the sakura season it is. In the summer, it’s a bit of a concrete bunker. Rivers aside, you have started two companies in Japan so far and currently running MakeLeaps … and actually rather than have me talk about it, why don’t you talk a bit about it?

Jason: So I’ve been in Japan since 2001. I came over originally to study martial arts. After about a year here, I set up my first business called WebNet IT which helps foreign companies who are setting up in Japan and also banks and embassies with their IT requirements and then we had a lot of problems when we started to get to scale at sending tons of invoices a month so we decided to build our own software to scratch our own itch which was both as I often say the best and worst decision that I have ever made because I had no idea how to build software, so I went thru…

Tim: So originally you weren’t planning for this to be a separate company you were just trying to solve a problem that you were having.

Jason: That’s correct and well the thing is, this is back in like 2004 and back then, there was no software that was available for the Japanese market that you know scratch this itch, that would allow companies to manage they’re documents with yen and with decimal points correctly because of course you know you use English software designed for the American market and you make an invoice in yen and it’s got decimal points in the kanji, doesn’t show properly and you have got all sorts of internationalization problems and it’s just a giant nightmare so we tried many of the American solutions, didn’t have any luck and so we realized well if we are going to do this, we’re going need to build it ourselves. So we built it and it kind of became a bit like a hobby project for me much like you’ve got a terrible car that’s rusting in your garage and you just go out there every weekend and try to make it look better and then like four years later, it’s something that you start to show your friends. That is pretty much exactly what happened after years of working on this and slowly chiseling away at it.

Tim: How long did it take from time from the time that you decided, okay we need a solution for this internally to the time you said okay we have a product we can sell, how many years was that?

Jason: This is an embarrassing answer to your question, Tim, but it took years and it’s not something that I wish, unfortunately you know, I wish I could say oh yeah I’m a very visionary entrepreneur and I saw the market opportunity from miles away and went out to take hold of it that is absolutely not what happened. So it got to the point where I just enjoyed showing it to other people, like oh wow check this out, I’ve got this new report and now I can say wow this guy is doing a really good job and that’s great, and this customer is my number one customer now and now that’s fantastic, I didn’t know that before because I couldn’t add up all the invoices because they were all in Excel and they were all in a folder somewhere and it was just dead data, and people started looking at that and say wow that’s really cool, are you selling that? If you do, I’d be interested to buy that and I’m like oh okay whatever, but it really did not dawn on me until finally after hearing this and having this conversation several times over, one person said I need your tool. I said oh yeah sorry it’s not for sale, and he said no no, I have no idea what is going on in my business, I don’t know if I’m profitable or not, I have hundreds of excel documents in a folder, I don’t care if this costs $500, $5,000 or $50,000 dollars, I just need this tool, how can you make that happen?

Tim: So your great brainstorm when you realized that you could sell this was when people start asking you to sell it to them.

Jason: Exactly! Exactly! Yeah, it sounds obvious in retrospect,

Tim: Well let me tell you, I’ve explained Make Leaps in the intro, but could you explain very briefly what the company does and who uses it.

Jason: Sure. So at this point 98% of our customers are all in Japan. Essentially what it does is in Japan right now almost everybody uses Excel to create, send and manage their invoices while overseas, almost everyone starting a business is using an online tool or cloud tool and there’s many many cloud tools for the American and English-speaking markets. So essentially we are helping Japanese companies manage their invoices in the cloud as opposed to through Excel which is what everybody is currently doing.

Tim: Actually tell me a little bit about your customers because you seem to have quite a range of users, everyone from like one person freelancers to some pretty large enterprise clients you’re working with right now.

Jason: That’s true. When we started, the system was extremely basic so it was only really capable of serving the needs of freelancers but as we built out the system and added more and more features, more and more businesses started to use Make Leaps and they stated sending us requests and, of course, business requirements for invoicing is slightly different to freelancers, so we started working on those kinds of features and then eventually we started to get interest from large enterprise companies and they had a set of features that they needed to do, so yeah as we continue to build out features, we are moving more and more upstream into larger and larger enterprises and very big public companies. We’ve got a very wide range of customers. One thing that I suppose I find interesting is, the information that’s on an invoice that a freelancer sends out is pretty much 95% identical to the information on an invoice that a very large company sends out. Right, so it’s a lot of the complexity and difficulty in building software to scratch that itch is in the way that you handle large amounts of data, large amount customers and large amount of documents and that’s where the tricky part is and that’s where we’re spending a lot of time and effort right now improving that area and making it so it is very simple and easy to manage huge quantities of data and invoices, so when a company comes to us and says okay, we are sending thousands or tens of thousands or hundreds of thousands of invoices a month, we need to have a really good answer for them.

Tim: One thing I think is really interesting about you and a handful of other foreign entrepreneurs here in Japan, the bulk of entrepreneurs seem to target language sensitive niches, so language training, translation, tourism, where they are dealing with a lot of foreigners but Make Leaps has really targeted on its Japanese clientele, you are running this like a Japanese company and that’s quite a bit different from your first company which was providing services to largely foreign companies. How is that different, what’s been different between the two?

Jason: So I would say firstly the buying; the way that foreign companies make buying decisions is very different to the way that Japanese companies make buying decisions.

Tim: How so?

Jason: Basically if you show a foreign company or a foreigner a product, typically their response is wow that looks like a good product, I think it would benefit me, how much does it cost? And then that’s where the discussion starts. Typically we found that if we go out and talk to a Japanese company and say here’s a great product, they’ll say that’s really interesting who else is using it? So back when we started we didn’t have a great answer for that right like no Japanese business wants to hear oh you would be the first. It’s kind of like oh okay, like there is safety in crowds, right like you know you want to be on the system that everybody else is using and if you are trying to build a system that you want people to use, it can be very frustrating and easy to give up in the early stages because a lot of people are very concerned about who else uses the software. So that was really big difference that we found and I think a lot of people encounter this and say, oh this is ridiculous like they get frustrated but I never really understood why you would get frustrated. It is like well, if you’re an entrepreneur your goal is to figure out the problem space and solve the problems related to the problem space and yeah we just accommodated that particular requirement by going out and doing a lot of case studies, interviewing users, looking for opportunities to share the fact that we have other, you know back then we had like oh we have tens of customers using Make Leaps, then you have the ability to say that now it’s hundreds, now it’s thousands, now it’s tens of thousands like the way to kind of share that with people, it was very critical for Japanese businesses or freelancers or business owners to look at the tools to say oh wow a lot of people are using it, I’m happy with this, okay I feel safe, let’s try it out and away they go.

Tim: But early on, you were doing a lot of sales yourself. What are some of the advantages and disadvantages of doing sales as a foreigner in Japan?

Jason: One thing is you are not part of the Japanese social structure so you can work outside that a little bit in a way that where you can do things that other Japanese people would have trouble getting away with right so I would go around to my friend’s office and say oh yeah we got this new version of Make Leaps and they’ll say oh wow that looks interesting, we’ll try it out some time and I’m like great well I’ll just sit here until you have a moment, I don’t want to bother you and they’re like what do you mean you’re going to just sit here? Oh well you know we really need feedback on this, so yeah yeah, no problem, no rush, whenever you have a minute in the next hour or so.

Tim: And a Japanese person could never get away with that.

Jason: It would be difficult right.

Tim: You’re violating all kinds of social conventions.

Jason: Right, right and you know of course I’m sensitive to social conventions but I also needed feedback. So you know, it kind of trying to get a nice balance between you know working towards what you need to move the business forward, maintaining relationships, keeping people happy and all that kind of stuff so I think that you often see this in Japanese companies like in Sony where sometimes they hire a foreign CEO because he can get away with things and do things that it would be much harder for a Japanese CEO to do. Right, so in much the same way, I think there are certain advantages in that area. There’s also definitely disadvantages which I’m very sensitive to, right like if you are a Japanese business and you find out that the invoicing company, an invoice in Japan is a very sensitive document with a lot of information in there that is very nuanced right and if I was a Japanese business owner and I thought well, you know I might use Make Leaps, but it’s run by foreigners, hmm would they really understand the particular requirements and needs of my business and I might be a little bit concerned about that, so we try to really present a Japanese face where it’s appropriate and where it is good so people can feel comfortable. One area where I was very happy was we ran a user meter probably about a year and half ago and this Japanese guy came through the door and he looked around and I heard him say, “Why are there so many foreigners here?” I walked over and I said like, “Hello, thanks for coming, and it was like.

Tim: Did he mean it in a good way or a bad way or he was just surprised?

Jason: He was just surprised. He’s like why are there so many foreigners, what’s going on here. So I walked over and said hello thanks for coming, what do you mean, why is there so many foreigners? Well I just assumed that this was a Japanese company run by Japanese people and I was like oh, well, it’s not. Yeah right so he was kind of surprised by that and for me that was very interesting because he was completely under the impression it was a domestic company.

Tim: Did he think any less of the company or was it more like that’s interesting, where’s the beer?

Jason: That’s exactly right, oh that’s interesting, where’s the beer? Up until that point he just had an impression because we really do sweat the details. Because we’re foreigners, we work doubly hard to make sure that we get all the details correct and nuances right and obviously we must be doing that well if somebody can use Make Leaps for a long time and not be aware whatsoever that this foreigner is actually running the company. So yeah that was pretty satisfying actually for me to hear that.

Tim: Actually you mentioned something earlier that sounds really interesting that Japanese companies view their invoices in a fundamentally different way than foreign companies do. What are the differences?
Jason: Well I would say a Japanese company sending out an invoice, the invoice is kind of an extension of that company and it’s an extension of the company both in manners, in the way that they are communicating, or the external face that they want to show to their customers, so if you send out an invoice that’s got a bunch of mistakes on it or you know the yen mark is wrong or looks weird or the kanji is garbled or something like that.

Tim: Or even something as simple as having the decimal places.

Jason: Or decimal places on yen or something like that, you are essentially presenting yourself as a company who doesn’t really know what it’s doing or is unable to grasp the nuances of Japanese business and in Japan of course image is pretty important and you don’t want to make mistakes like that on such an important document where you’re asking for money from your customers. They’re putting in their document and we are essentially creating documents for them on their behalf to send to their customers and there’s a lot of trust in that and we take that pretty seriously. You know we are very grateful when someone uses our software and we really want to make sure we make them look really, really, really good.

Tim: You actually acquired one of your competitors last year, right?

Jason: We acquired two.

Tim: Two, oh I didn’t know that. Tell us about that.

Jason: One situation was where this Japanese guy and maybe one or two others put together an invoicing company and the thing is, when you build a company, sometimes the first version of the MVP (the minimum viable product) is easy to put together, right like you put it together in a week or two, you get people to use it, they’re like oh wow that’s pretty good, but that’s not where the real work like ends. Right, that’s where the real work begins. Then it becomes a huge slug of you got to go out, talk to customers, customer acquisitions exactly, say okay what do you like about this, what don’t you like, what could we do better and you have to start to iterate and build on that, and get more and more people and listen to their requirements and start to understand customer segments and it’s just a marathon,

Tim: So these guys weren’t really willing to do that?

Jason: Um I think they got just a little bit tired and I’m not being down on them for that. It is hard work running a company, it’s really really difficult and if you’re not very passionate about the problem space, it is very hard to remain motivated right. For me I’m very passionate about invoicing and I realize how ridiculous that sounds.

Tim: No, no the world needs people who are passionate about invoicing.

Jason: Oh not too many hopefully, but just one.

Tim: So the companies you acquired, did you acquire for the technology, for the people, for the user base, what was your motivation?

Jason: So for the original company, I got in touch with a guy over at Twitter, originally not really thinking at all about purchasing his company or anything like that, but he responded to me and said hey would you like to get coffee. I said sure, why not. So we sat down and he said listen, you know, I’m looking at some other projects, would you be interested in buying us and Luke taking on our customers and looking after them. I said well of course if the price is right. So we thought about it and we decided okay, this is a really exciting opportunity to number one do a press release, number two add 1500 potential users, number, there is a positive aspect to being a company that is buying other companies, that is quite nice and reassuring for people as well. So in the end, even thought it was a bunch of work to do it, we decided to go ahead and bring more them on board and yeah, we got a lot of benefit from that. At that time, we doubled our user base, which was great as well.

Tim: Did most of them end up sticking with you?

Jason: Surprisingly yeah. We look in the system these days and a lot of them have stuck around which has been great. Definitely it has justified the purchase price that we paid. So, that has been really, really good. The other company that we ended up kind of acquiring or let’s say acquiring and basically there was one guy that contacted us out of the blue and said hey, we run a Make Leaps competitor, we are shutting down our service but we are looking for someone to take on our customers, would you be interested? To us, it sounded a little bit like Oh, you’ve won the lottery, just put in your credit card details or something like that but it sounded a little bit too good to be true, but we asked him to come in and have a meeting. Essentially his company was being acquired by a larger Japanese company and they said okay we have got no interest in this business, we want to shut it down. So the manager that was working there wanted to basically find a soft landing for all of his customers that were using that system. Some of the customers weren’t interested, of course, they were a little bit burned by the idea of using an online invoicing tool that is going away. _____ exactly exactly so _____ absolutely absolutely. Well I think in this guy’s position he really put his own reputation on the line to get all his customers onboard so it must’ve been just shattering for him to you know come into the office one day and say oh yeah, we are being acquired and we are shutting down this division. It is like just ah Geez.

Tim: It was his baby, right.

Jason: Yeah, yeah and he put his own reputation on the line and so he wanted to do the right thing by all of his customers and people that he introduced to the system. So in the end, he was comparing okay well I’ve got all of these customers and some of them are very big customers. Do I introduce them to Make Leaps, the scrappy startup run by foreigners or do I look for a Japanese company that is maybe a little bit more trustworthy and has been in the game for a bit longer. So in the end, he went around and had a meeting with us and explained the situation. He said okay, maybe it makes sense for me to give you the smaller customers and I will give the bigger customers to someone else and we said, well sure but if we are going to work on this, you know it’s a lot of work for us, we want all the customers and he said, well we’ll see how we go. I said okay sure. So then after the meeting with us, he went and had a meeting with a very large Japanese engineering company, 6000 engineers, you know publicly listed, big offices around all Japan and all that kind of stuff and he explained the situation to them. From what I understand their response was that sounds like a really interesting project, we are going to have a meeting in three weeks with a committee to discuss whether we are interested to continue discussions.

Tim: So that sort of ended the discussions.

Jason: Well that’s the thing, he was kind of like I don’t really have a tremendous amount of time here and I need to figure out a solution pretty soon and so he came back to us and said okay, so I wanted to give you an update. We said no, we want to give you an update. Here are all of the features that we worked over the weekend that we think is what you need, is this correct. He looked at that, and said what you did that over a weekend. We were like, yeah, not all of it is finished yet and not all of it is wired up in the backend but this is what we’re planning to build, is this satisfactory. He said this is great, this is exactly what we are looking for.

Tim: Oh my God, so in the time that it took the large company to get back to him to let him know that they were going to have a meeting in three weeks, you’d already prototyped the key features he needed to bring the customers over.
Jason: Absolutely so it took about a day for him to sort of realize, I am just going to go with Make Leaps, they seem to know what they are doing.

Tim: What is one of the biggest misconceptions foreigners and foreign entrepreneurs have about doing business in Japan.

Jason: I would say that it’s similar to the way they are used to doing business in their own home countries. Then they turn up in Japan. They have a meeting and they think wow that meeting went great. This is this is absolutely going to proceed, this is going really, really well, then they don’t hear back from them for three weeks and they find out the whole deal was canceled. There is a tremendous amount of nuance in Japan and indirectness that I originally found to be extremely frustrating, but now I have gotten used to it.

Tim: It is just that people don’t realize when a prospect is saying no or is it more subtle than that.

Jason: It is a little bit more subtle because I have a friend who wrote his entire thesis on all the ways Japanese people can say no.

Tim: Boy it’s a long thesis.

Jason: There were 52 ways and some of those ways were yes. Right, it was really hard to like work around if you are a business person trying to get a deal done and they are like wow this is a really interesting and we would love to continue discussions. The guy is like great, oh fantastic, this is going really well and he tells his bosses yeah this is going go great and they are all really excited and then of course, the deal never happens right, so that can be difficult to wrap your head around especially if you are used to coming from a more direct culture like America or Australia where people value directness, in Japan, people do not necessarily value directness and over time, you get used to that and you adapt but it takes a lot of time. It comes down to business making processes, how Japanese companies actually make decisions and one thing that can be very frustrating for foreigners is decisions are made in committees in Japan and those committees can take a long time to come together to discuss all the different various options and then to agree to move ahead. Now that is very frustrating. The positive side for that, is once the committee has made the decision to move ahead and it is all steam ahead right and they will make fast progress along the objectives the committee has agreed to. Getting the committee to agree can be frustrating and take time. So even if you’re pressuring somebody for an answer and they haven’t yet spoken to the committee, they are not going to be able to say anything to you that makes sense, so I mean, the appropriate thing is to say okay well, we are thinking about it, it is very interesting, I need to talk to the committee about it, and that might happen in three weeks’ time or whenever it actually ends up happening.

Tim: Right, right.

Jason: So foreigners are a lot more comfortable with making decisions on an individual basis and Japanese companies are not always comfortable with that, right and there is far more value in Japan to making decisions as a group and being happy with that decision as a group and then if it goes wrongly or if there is a problem, it is like well, we made this decision all together so really none of us are really to blame for this right because we all agreed it was a really good idea at the time.

Tim: But we will all take credit if it works out.

Jason: Absolutely right so there is a lot of upside and limited downside and so from that perspective, it is not necessarily a bad way or it is not a completely ridiculous way to make decisions I would say.

Tim: Okay. And it’s just the way it is.

Jason: Yeah, but you have to get used to it right.

Tim: So you can’t expect to walk out of the meeting with a deal.

Jason: No. You can hope to walk out of the meeting with the precursor to building a relationship that happens over days, weeks, months or years and then over time, if things go well and the committee agrees, everything is great and it will move forward and it will move forward very quickly once that decision happens, but that decision could take a long time to make.

Tim: Let’s shift gears a bit. You organized and you run the Hacker News meet-ups every month here in Japan.

Jason: Right.

Tim: How long have you been doing that now?

Jason: About three years. We are about to do our 38th, no 37th Hacker News event tomorrow.

Tim: Awesome, I’ll be there.

Jason: Awesome, I look forward to that.

Tim: So how has it grown over that time?

Jason: It started out with us just posting a thread on Hacker News saying, “hey is there anyone else in Tokyo, let’s get together for a drink” and we managed to rustle up 3 or 4 people and then over the years, it has kind of just grown out and I hear a lot of great stories where people have met employees or investors or they have found cofounders even, which is fantastic. Yeah we have met a lot of people that we have ended up hiring through Hacker News which has been very beneficial for us personally and it is just a lot of fun to just get drunk with a bunch of nerds.

Tim: That’s always fun.

Jason: Or work on interesting projects.

Tim: Well, I’ll tell you, the Hacker News meet-up is the first place I recommend that people coming from San Francisco or London visit to get plugged in the tech community here in Tokyo, it is a really great event.
Jason: Yeah.

Tim: The URL will be on the website so everyone can go find you and show up for an event when they are in Tokyo.

Jason: Cool, that’s great.

Tim: But tell me about the composition of it. Is it mostly foreigners, it is mostly Japanese or is it a good mix?

Jason: It depends on the event, but we get around about 30 to 40% Japanese people which is pretty good considering that hacker news is 100% in English so we can tend to get a very interesting mix of Japanese and foreigners or foreigners doing business in Japan or people who are traveling in from San Francisco or Silicone Valley. We actually had an interesting experience where maybe 2 Hacker News’ ago, two Y Combinator partners came and joined the event. We were a bit nervous and we were like, we hope it’s okay that we are doing this right.

Tim: Right.

Jason: They came in and they took the microphone and they were like, “oh we came here, we work at Y Combinator and we run the hacker news website,” and we were like oh, oh, here it comes.

Tim: Here is comes.

Jason: Yeah exactly.

Tim: And exactly, just to be clear, you are officially affiliated with Y Combinator.

Jason: Absolutely not. There was a meet-up that we had no official representation or connection to Y Combinator so the Y Combinator guys came over and said, “Yeah, we are really happy that you are sort of extending the Y Combinator brand and it is a really great group of people, and yeah thank you very much for doing this, it’s a lot of fun for us to come here,” and we were like oh wow, “That’s great,” whew! Yeah so that was very nice, very satisfying to.

Tim: Well, you are obviously doing something right.

Jason: Yeah, I’d like to think so. I’d like to think that sometimes we do some things right.

Tim: I think it is great that you limit speeches and announcements to 30 seconds.

Jason: Yes.

Tim: In fact, I think you have kicked me off stage once or twice for going over that.

Jason: Sometimes you just run shop, Tim.

Tim: Sometimes I just need to be kicked off stage.

Jason: I have been kicked off stage myself.

Tim: That’s right, I almost kicked you off.

Jason: That’s true, Jay you are at 35 seconds now, it’s time for you to shut up. I’m sorry, I’m sorry everybody. So it’s fine, no it’s nice because we find that if we don’t set a time limit, they drift right. People will start off at like 10 seconds and then like after 5 or 6 people will go 30, then like you just got some guy doing a monologue and everyone is bored to tears so we really need to just keep things moving along. We don’t want the focus to be on announcements and the lecture so much.

Tim: Well let me ask you this because actually both you and I came to Japan on nonbusiness reasons.

Jason: Sure.

Tim: And suddenly found ourselves starting a company, what made you decide to stay in Japan and start a company?

Jason: Well, I feel like I’m going to try to take the term back of opportunistic. It seems like a really negative term with a lot of negative connotations, but I think being opportunistic is a wonderful thing right.

Tim: You can be able to seize the opportunity.

Jason: Absolutely, right, you see an opportunity and you are like oh wow, I’m going to seize that opportunity and try to take advantage of that.

Tim: You’re right there should be a better positive word for that shouldn’t there.

Jason: The only other positive word is “hustler,” and that is also not necessarily a positive word exactly. Oh, “He’s a real hustler, oh shit, I should check my wallet.”

Tim: That’s an interesting point.

Jason: Yeah, you’re right. So I would say that I had an opportunity to start a company where a guy that I had met happened to like me, which was really nice and he said listen, I’m starting my own company and I need someone to do the IT, would you be able to do that and having no idea about how to do an IT project on a large scale, I said, “Yes.”

Tim: Right, so bite off more than you can chew and chew like hell.

Jason: Chew like crazy and so I was chewing like crazy for several months and it was very difficult. So then I failed very miserably and yeah this guy, he ended up firing me several times throughout the course of our engagement.

Tim: Oh my.

Jason: Yeah the first time was the hardest, right.

Tim: I imagine it would be.

Jason: Yes, so I’m sort of.

Tim: Sounds like a wonderful place to work.

Jason: Oh yeah, it was intense but this guy was under a tremendous amount of pressure. He was trying to set up a company in Japan not knowing a huge amount of how to do that. He was trying to get investments from overseas so he was under a tremendous amount of pressure and he suddenly realized oh no, perhaps this IT guy who I like that I hired is completely incompetent and doesn’t really know what he’s doing and that’s kind of a valid concern, but I don’t really fault him for that.

Tim: You don’t fault him for the concern but he could have handled it better.

Jason: Well yeah sure, right but this guy is sort of a bit master of the universe, kind of captain of business and he was very intense, and I was not prepared from either an inexperience perspective or an emotional perspective or an intelligence perspective back then to be able to handle that in a very appropriate way. Now I would handle that very differently.

Tim: Yeah, let’s talk about that because in a very short time, you went from being a somewhat introverted IT guy to running your own company, having to go out and sell something to make payroll.

Jason: Sure.

Tim: How did you make that transition?

Jason: Well honestly you know, I kind of owe a lot to this guy who was an extremely intense, very, very, very focused and aggressive guy and I would say three months with this guy really kind of changed the way that I look at the world right like, three months into this engagement, I was so much better prepared to deal with any situation because I had to think on my feet, I had to be razor sharp, lightning fast to respond to whatever it is that he might say.

Tim: So after dealing with your boss, dealing with customers became a piece of cake.

Jason: Yeah it was simple. Honestly after three months with this guy, I am like this is what business is like, this is terrible.

Tim: I want to get the hell out of here, right?

Jason: I was ready to quit after three months, right, but then I started working with another company and they were very friendly and polite and I was like oh wow, this was way easier. It was much, much, much simpler and so starting with a client like that is very aggressive and angry made things very simple and straightforward when I was dealing with pretty much any other situation, so I owe this guy a lot.

Tim: Are you still friends?

Jason: Yep.

Tim: Alright, that’s awesome, that really is.

Jason: Yep.

Tim: That says a lot.

Jason: Yep, no we are still good friends, I like him a lot, he’s a great guy.

Tim: That’s cool. So it sounds like it you’re kind of stumbling your way into success. You suddenly found yourself running an IT services business, you suddenly found yourself with a great invoicing product that your customers were begging you to sell to them.

Jason: Stumbling to success that will be the title of my memoirs.

Tim: There you go.

Jason: I’ll take it, I just want an acknowledgement in that book, I’ll write the forward. But, at the end of the day, you know, doing your business in Japan comes with its own unique set of advantages and disadvantages, positive things and negative things right. Some of the positive things are once your customers start to use your product, they will be extremely loyal. You would literally have to physically assault someone in their office to get them to stop using the service.

Tim: I have a friend who did that actually.

Jason: Oh I think you told me this story. Yeah.

Tim: However this is a story for another day, another set of beers.

Jason: That’s okay.

Tim: So if people want to get in touch with you in Make Leaps whether it is investors, customers, enemies, stalkers, whatever, what is the best way.

Jason: So for stalkers, I would recommend following me on four squares so they can see where I’m at because sometimes I publish my location so they can come and stalk me a little bit more efficiently. For investors and customers or just people who are interested to connect with me, I am on Twitter at @JasonWinder and I am also on email at JayJ@makeleaps.com and they are the two best ways to get in touch with me.

Tim: Okay and we will all that information up on the website so people who didn’t write that down right now will still be able to get in touch with you.

Jason: That’s very nice of you Tim, thank you very much.

Tim: Thanks for talking with me.

Jason: My pleasure. It’s always good to see you man.

== Interview Ends ==

Alright, we are back and sobered up again. Listen, if you want to check out any of the things that Jason and I talked about, have a look at the show notes for this episode disruptingJapan.com. If there’s people you want us to interview or questions you want us to be asking be sure to drop us a line at feedback@disruptingJapan.com and the best thing that you can do if you like what we are doing and you want to help us get the word out, please go to iTunes, write us a good review, it’s really the absolute best thing you can do to help us support the show and we really do appreciate it. I’m Tim Romero, thanks for joining me.