Brandon W Proposal to Laura P at Shibuya Crossing

There’s Always a Way – The Time I Almost Spent $10,000 to Impress a Girl

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I almost spent $10,000 to impress a girl. Almost.

Three years ago last month in June 2009, I proposed to my wife. From idea generation, coming up with a strategy, drafting a plan of attack, setting priorities, scheduling, budgeting, all the way to the execution and implementation, the entire “operation proposal” took several months and lots of brain juice. I wanted it to be special, I wanted it to be fun, and I wanted it to be something we could talk about for years to come.

I had several ideas for how I could “pop the question”:

1. Propose while bungie jumping:
I’d always wanted to try bungie jumping, and it seemed like a great way to kill two birds with one stone. ;)

Problem: I sneakily poked around the idea of going bungie jumping to my fiancee-to-be, and quickly realized the problem with the plan. The likelihood of anyone saying yes to any type of proposal drops significantly when under stress. Bungie jumping isn’t something she was particularly excited about, and I could already imagine her saying no a whole lot during the bungie jumping before I even asked the question. This idea had no future.

2. Propose on the train while going to Shibuya:
We lived in Toritsu Daigaku, which is about 10-15 minutes west of Shibuya on the Toyoko train line. The plan was to rent out all of the ad space in a carriage – the area above the head on the side of the carriage, and propose on the train while we were commuting into the center of the city.

vicious business (ad train)

Problem: Even though I was really excited about this idea, I quickly found out a huge hole in this plan before I even started looking into how to do it. If everything went to plan, I would surprise her on the train with pictures of us plastered all over the carriage, she would say yes, people around us would clap their hands, it would be great.

But here’s the problem. This whole sequence would probably take 3 to 5 minutes. And then we would have had to deal with the awkwardness of being the center of the attention on the train for the remaining 10 minutes. It would be hugely uncomfortable, with the train stopping every other minute to pick up more passengers. The embarrassment would overtake the excitement and become the focus of the story in the years to come.

3. Propose at the Shibuya crossing:
The busiest and most exciting crossing in the world, Shibuya was our gate way to the center of Tokyo, a place where we go almost every day to meet up with friends, find new restaurants, and have crazy nights out. It’s a place full of memories and seemed perfect for the proposal.

Shibuya Crossing in particular was the center of our universe. No matter what we did, we’d always start there, and come back to there at the end. There are three big TV display at the crossing on the buildings – if you’ve seen the poster for Lost in Translation, you’ve seen the one in the center – the one with the dinosaur on the poster. 

Lost In Translation Lost in Translation 17

This idea seemed to have legs. Now I needed to make it a reality.

The big TV display is one of the key components that makes the crossing so iconic and used in many films the world-over. I decided I want our pictures up there when I proposed.

But how to do it? All the ads I’d seen on those TV displays were, naturally, big brands – Coca Cola, MTV, Nike. It wasn’t clear how I could make this happen. My first reaction whenever I am in a similar situation is to spend hours and hours online searching for an answer. Unfortunately/fortunately, my ability to navigate the Japanese internet was severely limited by the tiny number of friends I had on Mixi (Japanese version of Facebook) and by my inability to read and type none-food-related Japanese. I had to find help outside of the Internet.

At the time, for one of our projects at work, my Japanese colleagues managed an outdoor display campaign. So I asked around and found out roughly how much a smaller outdoor TV display in a less busy area would cost. It was for an hourly 5-minute spot for a few days. Not exactly the same but it gave me an idea how much this might cost – the number was quite discouraging.

Nevertheless, I liked the idea and I wanted to find out more. I remembered a business man from Adobe Japan who I’d been talking to for months on a deal. We had a business relationship, but we’d also had drinks outside of work a few times (to help with the negotiation of course – that’s how things work in Asia). In one of our none-business conversations I had learned that he had worked for an outdoor TV display technology company prior to joining Adobe. Perfect! As soon as I remembered this, I contacted him to see if individuals could rent out ad spaces on the TV displays, who I should contact, how long the wait was, and how much it would cost.

He was excited about my plan and started making connections for me, handling all the communications with the various contacts he had. We found out that it is possible for individuals to rent these out, that the three TV displays at Shibuya Crossing operated separately, and the earliest spot available were synchronized ads that get displayed all at the same time across all three TVs. The good news was that we knew we could do it, and do it in time for the proposal (I didn’t want to wait months.). The bad news – this was going to cost $10,000 (USD)!

Right. “No wonder you don’t see these kinds of proposals more often”, I thought to myself. Even if I had the budget to do it, I knew my hopefully-fiancee-to-be would not be amused when she found out how much this had cost.

But as I always believe, there must be a way. This was something that I really wanted, and I wasn’t ready to accept it not being a possibility. I considered the options – maybe I could try to get just one TV at a slow time of the day/week, or shorten the air time, or find a sponsor, or… something. I asked my friend to keep looking and try different requests, and at the same time I reached out to a few Japanese friends for ideas.

A couple weeks went by and things didn’t progress. My options were still $10,000 for a grand show, or no show at all. And then I got a text message from a friend who I was in the Sony orchestra with.

“message on TV display, FREE!”

Really?! I didn’t believe the words. Free to put up any thing on the huge TV display in one of the busiest intersections of the world where millions of people walk past every day? I was sure he was mistaken. But nonetheless, I couldn’t help but feel a little bit excited that I might just be able to propose the way I wanted.

So I called him, and he had found out that the company operating the biggest TV display at the crossing was offering a service to let people show short messages to their friends. They do this every day after 6pm, 5 minutes before each hour, until 10pm. I went to the crossing the next day at 6:50pm, waited to see if they did indeed show none-commercial messages, and he was right! All of the messages were text only and mostly happy birthday messages, but this was a good start.

At the end of these messages, there was the contact info for the company offering the service and I quickly jotted it down. My friend helped me communicate with the company in Japanese the week after, and asked if they could put a photo background with a text message over the top, were okay with a proposal message in English, and we then scheduled a date that worked perfectly.

I sent in the final request, photo, and everything else they requested. We were good to go! A personal message with a photo of me and my fiancee-to-be on a big outdoor TV display at one of the most famous intersections of the world, all at the cost of free.

Of course, no amount of planning was enough to prepare me for the actual moment. I downed a beer at a convenience store three blocks away from the crossing, tricked my confused lady to look at the ads on the TV display while I was waiting, got down on one knee when the photo and message appeared on the screen. The world stopped for a moment until she read the message, noticed I was kneeling on the floor, and screamed.

Unaware Victims

I used to drive past this huge billboard ad in downtown San Francisco when I commuted from East Bay to EA in Redwood Shore. On the billboard was Mohammed Ali in the ring with the words “Impossible is nothing.” Maybe I was conditioned by this, to believe that wherever there is a will, there is a way.

It’s a theory that can’t be proved, but in my experience, if you look hard enough there is always a way. Always.

Probably why my now-wife calls me the “Yes-man“.

(Picture of the TV display I took on the night of the proposal.)

(bonus picture: the Impossible is Nothing Ad at the Shibuya Crossing, on the building opposite of that TV display.)
Adidas - Impossible Is Nothing


How a Simple Technique Helped Me Figure Out What I Want to Do with My Life


The hardest questions to answer are the ones about ourselves.

When I was having my quarter-life crisis at the grand age of twenty-eight, I started looking for an answer to this all-important question: What Do I Really Want to Do with My Life? The answer to this probably changes depending on my age. But I knew if anyone asked me on the spot, I would have no answer. I couldn’t live with not having at least one answer to this question. 

After all, shouldn’t this be pretty easy? If you ask me what I want for dinner tonight, I can tell you in less than two seconds (the answer is Pad See Ew). If you ask me what I want to do tomorrow, this Friday night, or on my next trip aboard, I can give you an answer without much hesitation. But when you extend the timeline to an extreme – a Lifetime, it suddenly becomes an almost impossible question to answer. The risk of giving a wrong answer becomes much bigger when the time is extended. Spending Friday night at a boring event would only cost me a couple hours and I can easily recover next day/week, but when it comes to a lifetime – I risk steering my life in the wrong direction! 

Another problem with trying to answer this question is, where do you start? How do you know the logic and reasons you’ve given yourself to answer this question now will still hold truth later? How do you know the choice you make now, which presumably you based your decision on making your future self happy, will satisfy all the needs and desires you’ll actually have in the future? 

The fact is, we can never know for sure. (read more about this topic on Stumbling on Happiness) But that doesn’t mean we shouldn’t try. So I dreamed about doing different things, being different people, and having other’s lives. As you can probably have guessed, day-dreaming and imagining didn’t really resolve anything for me. It felt too … unreal. I needed something more concrete if I were to buy a one-way ticket to my life’s journey. 

Then I draw inspiration from one rather mundane event that happened during that time – a performance review. Not unlike many other companies in the US, Sony in Japan also had performance reviews every six months. Since I was interviewed by my direct superior who I’d worked with closely every single day and knew me inside out, the review process was more or less just a formality. However, one question from the review stood out and lingered in my head days after. 

Where do you see yourself in 5 years?

Such a simple question, and yet it puts me in the right frame of mind. If I know what it feels like in 5 years of time to be at a certain position, I can at least have a pretty good guess if I will like it or not! 

So not unlike the performance review, I gave myself an interview. 

I pretended to be a journalist for a major magazine, and interviewed my future self in 5 years in different roles that I think I’d like to be in – as a full-time writer, a founder of a software company, a founder of a game studio…etc.

I started with simple questions like, “What is the name of the company” “What is the title of your first novel?” to more specific questions like, “What projects are you working on?” “Who inspired your products / your style?” “How many people are in the company?” “What does your office look like?”. 

Then I wrote down all the questions in as much detail as I could imagine, pretending that I were in those particular positions – as an established writer, a CEO of a software company, a core member at a game studio. The more questions I answered, the more words I put down, the more I felt like I was that person.

I experienced what it was like to be that future me. I learned quickly if I will be happy being that particular person

That’s when I decided I am going to start a creative studio, with a small team, flexible location, and focus on independence, creativity, and people. 

If you are also trying to figure out what you want to do, instead of trying to answer that question directly, try interviewing yourself. It’s a quick way for you to understand the “What If’s”, and best of all, it is fun to do :)

BBC Radio London interview Sir Richard
Brandon, Why is Sir Richard Branson all over this post?
Why reader, you’ll have to stay tuned to find out!


BUT I am NOT a Programmer, or an Artist, or a Writer, or a Marketer…

People are given titles. Our titles give us an identity, a way to introduce ourselves to the world, a sense of security. If you are in a well-respected position, you feel powerful when stating your title. “I am the CFO of Billshut Financials.” See there, instant power shot. It validates your skills and your accomplishments. It confirms your importance professionally.

200px Fleming007impression
“Bond, James Bond, and I am a spy.”

But what happens when you want a different title? What if this thing you want to build requires people with different hats than the one you currently wear? “I have a great idea but I am not a programmer.” “I am a programmer but I can’t design for shit!” Many people stop here. These thoughts have prevented some of the most brilliant ideas from being executed.

If you find yourself in this position, you have two options.

1. Find someone with the right hat to work with you.

If you have the resources (money, network, contacts, power, persuasion skills…etc.), you can hire or partner with people with relevant skills to help with your projects. The challenge is finding the right people who share your value and motivation. This is a topic for another day.

2. Do it yourself!

If you are like most people who are just starting out, you may not have the resources to hire help. But don’t let that stop you, and Just (learn to) Do It!

When I first started Studio Pepwuper, I wanted to go with option 1 and hire people to help me build my games. I spent a few weeks looking at candidates, outsourcing studios, partnering development houses, and eventually found a great candidate that has all the experience needed for the project. But very soon I realized that with the money I had saved up, I could only hire them for 6 months. And if at the end of that 6-month period I didn’t have a game out, or if the game didn’t sell, it would be GAME OVER for the studio. It was too risky of a position to be in and I had to re-evaluate my approach. Instead of hiring out the development, I decided to put my head down and learn to do it myself – learning to code, to make art, and to design. (more on this here & here)

To be frank, it wasn’t easy. It was an 8-month exercise of banging my head against the wall constantly. It was like being back in school, except instead of knowing when the exam is, I had to fight against time – every month in prolonged development was another month of living expenses gone from my savings.

But I did it. I wrote all the codes and got all the art work and music/sound into the project. The game was released. It was done. 

That isn’t the end of the story. The real benefit of doing it yourself is not in getting it done. It’s in all the the side-effects that happen while you are making it happen. I got to learn the in’s and out’s of game development on a tight budget. I understand how to write codes, and more importantly, how to read them, so when I looked for help I knew what to ask for and knew what my team was talking about. I learned to know how long things take so I knew how to better evaluate opportunities and partners. I learned to really appreciate artists and designers and learned that good design and good art takes time. 

And I got to share my experience, through which I got to know many talented, motivated, encouraging, and inspiring individuals. Without this experience I wouldn’t have my current team, and who knows where the studio would be if I hadn’t gone through this 8-month marathon. 

So next time when you think you can’t do something because you are not a programmer, not an artist, not a writer, not a marketer, not a networker, not a public speaker, not a journalist, not a photographer…etc, STOP.  Don’t let your title limit what you can do. You are what you do. And don’t be afraid to spend time learning. There’s rarely any downside to be more skilled, especially in what you want to do. 

Note: I was lucky enough to quit my job with savings that would allow me to survive on pot noodles for at least a few months, but I know that many people don’t have this “luxury”. To you I point you in the direction of Gary Vaynerchuck‘s presentation at the Web 2.0 Expo NY (

“If you want this, if you’re miserable, or if you don’t like it or you want to do something else and you have a passion somewhere else. Work nine to five. Spend a couple hours with your family. Seven to two in the morning is plenty of time to do damage. But that’s it. It’s not going to happen any other way. …Everybody has time. Stop watching fucking Lost!…”

p.s. I never look good in hats. I spent 20 years looking for a hat that fits me across the world wherever I go, but I can never find one. Maybe I am just not meant to be wearing any particular hat.