Tim Romero is a Tokyo-based innovator, author, and entrepreneur who finds speaking of one’s self in the third person to be insufferably pompous and pretentious.
So I’m going to stop.
My dreams of being a rockstar never worked out, but over the years I’ve managed to have fun, make friends, fall in love, sell a couple of companies and bankrupt a couple of others. At 51, I’m still trying to decide what I want to be when I grow up.
I believe in Japan and the startup community here. Japan’s best days are ahead of her. If you listen to the founders and creators here, you hear a very different story than the politicians and academics tell. I participate actively as an investor, founder, mentor, and all-around noodge. I work with TEPCO and other large Japanese firms to use new technology to create new businesses, I teach corporate innovation at NYU’s Shinagawa campus, I’m a Forbes contributor and in my copious spare time, I publish Disrupting Japan, which is a labor of love.
That’s me in a nutshell, but if you really want to know, let me just open this bottle of wine and I’ll tell you …
My Life Story
On September 17, 1966 in Washington D.C., I came into this world naked and confused, kicking and screaming. My outlook on life has changed little since then. My parents were too young to take care of me and put me up for adoption by a wonderful couple (aka “Mom and Dad”) who would treasure me, feed me, and move me from my cosmopolitan Georgetown home to the Virginia suburbs.
I had a boring childhood. I recommend a boring childhood if you have the option. Like all eldest sons, my treatment of my two little bothers fell into that grey area between play and abuse. We fell out of trees and caught tadpoles in the creek. I once cracked my skull open trying to jump my bicycle over the Leoni’s driveway. I required stitches, but somehow emerged from childhood without significant brain damage.
When I was 13, I started my first money-making venture. I planted tomato seeds and when they sprouted, I went around our neighborhood selling the plants. It was not a scalable business, but the money was good for a 13-year-old boy in Virginia.
I wasn’t one of the cool kids in high school. I had friends, but as an overweight kid with glasses and bad skin, my social options were limited. The fact that I sold tomato plants probably did not help. I was on the debate team and spent most of my free time playing Dungeons & Dragons and programming my Commodore64.
My sophomore year I noticed that girls liked boys who played guitar. I learned to play guitar. Girls liked it. I was onto something. I lost weight and got contact lenses. Things began to look up.
College and Southern Rock
Before I started classes at the University of Virginia, I wanted to be a lawyer. I attended the first meeting of the pre-law student union and realized I was mistaken. Fortunately, Carl Sagan and my high school physics teacher had given me a fascination and awe of astronomy, and I ended up majoring in physics. Physics and cosmology engross me to this day.
I took only one computer science class, Introduction to Pascal. After the first month, my professor strongly urged me to drop his course. He claimed I had a bad attitude. In retrospect, he was probably right, and when your professor suggests you drop his class, it’s usually a good idea to do so.
I was still poor, but being poor doesn’t really matter in college. I paid for school with a mix of part-time jobs, a few debate and public-speaking scholarships (yes, that’s a thing), a $3,000 gift from my grandfather, and by playing cover music in bars and clubs throughout Virginia and the neighboring states.
A lot of people were telling me I had talent. I was at least good enough for people to pay me to play, and that’s what mattered. My bands and I played some rough bars. A few biker bars. Bars with metal detectors and gun lockers. We once played on a stage behind chicken-wire. I still nurse a grudge against our bassist David for not having the guts to play Rawhide.
But even in the worst bars, the audience was wonderful. The South is like that. Music is special. We played some Creedence, a bit of the Allman Brothers, and a lot of Skynyrd. My God, so much Skynyrd! If I never hear Freebird again, I will die a happy man.
Tokyo and Pop Rock
By graduation, music had become far more interesting than physics. A strange series of coincidences resulted in me being signed by a Japanese record company. I received my diploma and flew to Japan to be a star. My music career was brief, even by Japanese standards. A month after my arrival, the company unilaterally canceled my contract and wished me the best of luck on whatever I thought I could do about it.
No one knew it at the time, of course, but the end of the eighties in Japan was the peak of the biggest economic bubble the world has ever seen. Salaries were high, and everyone was in a party mood. I spent my days writing speeches for Japanese businessmen, my evenings playing music, and my nights dancing at Julianna’s until the first train.
Two years later, both my music and professional careers had stalled. I decided to move to Los Angeles to give music one more shot.
Los Angeles and Rock Bottom
The rock and roll lifestyle involves far less sex and drugs and far more macaroni and cheese than most people imagine. I played coffee houses, parties, in back-up bands, and did a bit of studio work. The problem, however, was that I was an undifferentiated product. I was good, but not significantly better than thousands of other singer/songwriter/guitarists taking up space in Hollywood. A famous producer once told that I was too “goofy looking” to be successful as a singer. I was still not one of the cool kids.
Two years later, I was 26 years old, $35,000 in debt, and effectively living in my car. I was done. I cut my hair, read a few books on database programming, and landed a job programming dBase at an import/export company called Limousine International. The business had nothing to do with cars. The Japanese founder had simply liked the feel of the word. He pronounced it slowly and with unconcealed satisfaction.
Starting Things Up In Japan
Limousine International transferred me back to Japan. I built and maintained a distributed inventory management system for them and tried my hand at being a wholesale buyer. I traveled around North America buying jewelry, building materials, vintage sports memorabilia and (I swear this is true) used cowboy boots. By 1997 I had paid off my debts. This new Internet thing seemed promising, so I quit my job and began freelance web design and programming.
After a series projects that never gained traction, I started Vanguard in 1999. Vanguard was an e-commerce ASP (“ASP” is what we old-timers used to call SaaS). Over the next eighteen months, Vanguard grew to more than $1 million in revenue, 16 staff, and marginal profitability. I sold Vanguard to Digital Garage as the dot-com bubble burst around us.
The dot-com crash was the Cambrian extinction of Japan’s startup ecosystem. Many well-known startups and VCs folded, and the impact left a smoking crater where a vibrant, overfunded startup community had once thriven. As in all mass extinctions, however, the fit and adaptable survived to rise up and fill the ecological gaps that had opened up.
Between 2002 to 2007, I launched a dozen projects and two actual companies in domains including document classification, inventory management, web-tools, and customs clearance. Most had customers, some were profitable, but none could scale into a billion-dollar business.
Digging up Roots
A subplot that wound its way through this period of my life was the search for my birth parents. I never thought much about them when I was young, but I began to realize that they probably hadn’t forgotten about me. I didn’t really have any questions for them, but I wanted to get in touch to let them know that I turned out alright. I was happy. They didn’t need to worry or wonder about me anymore.
The search itself took over two years, but the time was mostly spent waiting for various agencies and organizations to get back to me. Our reunion was more casual and less emotional than any of us expected. It turns out both of my birth parents are lifelong serial entrepreneurs. My birth father died of cancer a few months after our little reunion. I am deeply grateful I had the chance to meet him. My birth mother and I still send email and Christmas cards.
I Almost Cut My Hair
Back in Tokyo, I was working 60-hour weeks but none of my projects were gaining real traction. I began questioning the entrepreneurial path I was on. The questioning felt familiar. Walking away from my startups hurt deeply in the same way that walking away from my music did over a decade before. I spun down or sold off my projects and started building software for other people. The pay was better. The stress was lower. Life was good.
In 2008, I married a wonderful Japanese girl named Ami. I get along well with her whole family. I’m thankful for that. Too many mixed-race couples have hostile in-laws on at least one side.
Within a few years, I was, by all external measures, thriving in my new role as a responsible member of society. I was now running software development for Zurich Financial in Japan. But something was horribly wrong. Before I could figure out exactly what it was, my story and everything else in Japan was interrupted by …
The Tohoku Earthquake
On March 11, 2011 a massive 9.0 earthquake and several large aftershocks slammed into Japan. What I saw in Tokyo that afternoon demonstrated the absolute best aspects of both Japanese society and the Japanese people themselves. All public transport had shut down. Phone networks were overloaded and useless. No one really knew what was going on or if their loved ones were safe. Electric power was spotty.
I joined the throngs on the packed sidewalks as we all tried to make our way home. People were obviously stressed and worried, but everyone was unfailingly polite. Displaced and anxious office workers and students were waiting for the green light at intersections, asking and answering questions on how to navigate Tokyo’s labyrinth of surface streets, and patiently queuing to buy supplies at convenience stores. No shouting. No pushing No one telling anyone else what to do.
After a major disaster, five million people calmly walked out of Tokyo and went home.
It would not have happened like that anywhere else on the planet. I knew Japan would be OK. She would get through this earthquake. She would find a way through the current economic slump.
You Can Take a Founder out of the Startup but…
The shaking had stopped, and I was back at work at Zurich. This was the job everybody is supposed to want. Stable company, high pay, short hours, supportive company culture, (mostly) friendly co-workers. But I was miserable, and I felt guilty for feeling miserable. I had to change.
I made some calls, set up some meetings, and worked out a plan to bring Engine Yard (an American cloud-computing company) into Japan. Just thinking about the new job and the new challenges got me excited.
Explaining this to Ami was harder. She really tried to understand, but there was no rational way to explain why I wanted to take a job at an unstable company where I would work much longer hours for much lower pay. In the end, I think she just accepted that this was something that would make me happy. Somehow she also managed to convince her parents that the job change was a good idea. I don’t know how she pulled that off. It could not have been easy.
I tore into Engine Yard like it was my own. I recruited a truly amazing team, and after two years Japan was accounting for 9% of new revenues and 15% of new customers globally. Sadly, in the fall of 2014, headquarters pivoted out from underneath me. Globally the company was not achieving the explosive growth startup investors demand, so the decision was made to consolidate around a core team in San Francisco and shut down the Japan office. There was talk of moving me to headquarters, but my place is in Japan for now.
I went back in project mode, and by the spring of 2016, ContractBeast was in private beta with strong investor and customer interest. Two weeks before investors were to wire funds and the rest of the team was going to quit their jobs, however, I pulled the plug. Some were upset at the time, but we all now agree it was the right call.
An article I wrote about it that went viral. Why I turned down $500K, Pissed off my investors, and Shut down my startup. Being internet famous for two weeks is less fun than you might imagine. It also turns out Thunderbird crashes when you have over 2,000 emails in your inbox. I responded to as many as I could.
I eventually would like to leave this world a slightly better place than I entered it, and I’m still figuring out the best way to make that happen.
Things are relatively stable right now. That’s nice for a change. In addition to my writing and teaching, I work with companies like TEPCO to help develop new lines of business in Japan, often using Western startup technology. I seem to be pretty good at it.
So that’s me. Tim Romero. A work in progress. If you decide to get in touch, you won’t be talking to a stranger.