That's a lot of moving! In this post I'll briefly outline why the company moved around so much. 


This is where the company was founded April 4th, 2008 with the initial seed investment from the Director of PayPal, Japan. See PlaySay's Love Story, How it All Began. Tokyo is my favorite city in the world, without doubt (and I've been to 21+ countries). 

PlaySay's 2008 office in Tokyo (my room).

By 2010 I decided to move PlaySay Inc. out of Japan mainly because of Japan's:

  • high risk adverseness
  • lack of startup climate
  • high small business regulations and red tape
  • two decades of economic stagnation and a rapidly shrinking and aging population
  • scarcity of venture capital
  • 2nd most expensive city to live in the world

I wasn't surprised to read that Japan recently ranked lowest among worldwide advanced economies for attitudes towards entrepreneurship (source). Most know Japan as the land of innovation, but I can assure you it's surely not in small business, software, entrepreneurship, etc. (just maybe skateboarding). 


I've spent more years in Philadelphia than any other place in my life. I love Philly. Once we decided to leave Japan, San Francisco was first on my list. Unfortunately, I couldn't even come close to affording San Francisco. Philadelphia was a no-brainer at that point.

PlaySay's 2010 team in Philadelphia in our free office space from the GoodCompany Ventures program.

By this point we had captured 18% of our initial target market (proven product-market fit) and had a 60% return on investment (proven sales funnel). Taking advantage of the economic downturn, I gathered over eight highly qualified individuals (most were MBA's) to work on a commission basis. The objective was to scale our proven product/model into eight new languages over the course of three months. We did it! 

To our dismay, we could not successfully replicate the success of the model in these other markets we scaled into. We did, however pivot our product for a much more attractive opportunity in the language learning space (see our Lily product in this post). With this and more, we closed venture financing from the most active venture capitalists in the education space of the USA. They strongly encouraged us to move to DC. 


We obliged our investors and decided to move to DC for the following main reasons:

  • was next door to our investors
  • highly stable economy relative to other US cities
  • ~$15M in R&D spent locally by federal government (a big potential customer for us in particular at that time)
  • 24th best startup ecosystem of the world
  • constant influx of well-educated and multi-cultured people

Here's us in our 2011 DC office and that goofy social gaming advisor of ours, Sameer.

By July we recieved a second follow-on investment from our investors. We launched as a TechCrunch Disrupt Finalist in September of 2011. By November we received another follow-on investment from our investors. We were actively in search for cheap all-star developers willing to work for equity (sound familiar, startups?!) and were finding it very difficult to find such in DC. After all, it's the city with the highest income of the USA. Also, by the end of 2011 we were no longer pursuing the government as a potential customer. We were no longer seeing too much value in having our company in DC. 

San Francisco

Location, location, location! As I formerly mentioned, I was eager to move PlaySay to San Francisco since our initial departure from Tokyo. We found two incredibly talented and affordable developers that were eager to work for us in San Francisco. They were both happy to forego a high salary in exchange for more company equity. We adamantly moved the company to San Francisco because: 

  • #1 startup ecosystem of the world!
  • access to better mentors and advisors
  • access to better talent
  • access to more funding options

Here's our new 2012 sunny office in San Francisco (SoMa) - we even have a foosball table!

We cut our burn (i.e. monthly spend) in half since we moved to San Francisco. Our team chemistry and productivity has never been better! As our friend Greg says, "We're living the dream!"

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