US Immigration is completely broken for startups

A lot of talk has been made recently about the shortcomings of US immigration policy and how it’s hurting the US’s competitive edge in the global economy.  A good friend of mine who is a Canadian, and acting president of an LA based company valued at > $100M just had his visa revoked and isn’t allowed entry to the US.  That was enough to get me to write this post informing people of my personal experience with starting and working for companies in the US as a foreigner which I believe demonstrates some of the problems.  For more of a history on the shortcomings read about it the Startup Visa act here.

3 Canadians get funded

In 2007 after myself and 2 Canadian friends spent about 6 months bootstrapping Attassa from Edmonton Canada, we raised almost $1M from Silicon Valley based Tandem Entrepreneurs – who at the time had a slightly different investment model than they do now.  We were building software to solve a lot of the pain in document and email collaboration and were tightly integrated with the Microsoft technology stack – Windows, Outlook, and Office applications.  Once we closed funding we decided it was best for the company to nestle up closely to Microsoft in Seattle.  Seattle obviously has a deep talent pool of Windows engineers, and we viewed Microsoft as a potential partner or acquirer.

2 Canadians get TN Visas

Myself and Rod both arrived in Seattle with our investment money, and our freshly printed TN visas and set up shop next to Dwayne.  We spent about a year working on product.  We hired a full time engineer, and paid for several part time consultants, and a book keeper.

2 Canadians get TN Visas revoked

During our time in Seattle, I traveled back to Edmonton about once a month to visit family.  I did this for about a year without issue.  That all changed one day in October.  Rod had been travelling back to Canada earlier that month and was denied entry on his trip back to the US.  His Visa was revoked.  I was actually in Canada when his visa was revoked, and naturally, this flagged our company, and when I returned to Edmonton International to fly to Seattle a few days later, my visa was also revoked.  I was given 2 days to get in and out of Seattle to deal with my apartment and belongings.  If I wasn’t back in Canada after 2 days, I’m not sure I’d ever be allowed back.  Ultimately, they believed that the job I was performing went above and beyond what was allowed for my visa type.  I won’t go into too many details about what went down at the airport but at the risk of sounding overly dramatic, I will say that those 3 hours of interrogations were quite possibly the most brutal 3 hours I’ve ever experienced in my life.  If you’re interested, read Zack Homoth’s story.  He was a Y-combinator kid that got rejected at the border.  It pretty much describes the nightmare I experienced.  At this point though, it was as if USCIS told us they didn’t want us or our ~1M investment.

One Canadian gets an H1B, the other … no dice

We put our hellish experience at the border aside and both applied for H1B’s.  We still wanted to do business in the US.  Our applications were pretty near identical, at least the company portion of the application.  Rods was approved, mine was not, for reasons I still don’t quite understand.  They claimed we were missing evidence (tax info, payroll info) that we clearly had sent them.  The cost to re-apply was too high so I ended up staying in Canada and working remote.

During this time period I travelled to the US to play Ultimate frisbee (of all things), and to visit friends on weekends.  Each time crossing the border, I typically spend 45 minutes in secondary screening answering questions about the intentions of my trip.  Believe it or not, I once was turned away at the border when trying to drive down to Seattle from Vancouver.  The reason?  I was carrying too much laundry in my Rav4.  Yup … I’d forgotten to drop my dirty laundry off at home before heading down to Seattle, and they thought it was a red flag that I was entering for the weekend, but had 2 weeks worth of cloths.  Fair enough I guess …

We get acquired by a US company

In December of 2010, Attassa was acquired by Yousendit, a successful exit for us and our investors.  By this point though, Rod and I are both back in Canada, largely due to the immigration nightmares that we’ve faced.  A bunch of cash that could have stayed in the US basically left the country that day.

But … I decided to move to the bay area after the acquisition, while Rod stayed in Canada

I decided to move down to the US after the acquisition.  I worked at Yousendit for a year and as of last week gave notice that I’m leaving in April.  I’m starting another venture but ….

I’ve got to do it from Canada

Despite preferring to start from the Bay Area, and having the financial means to bootstrap for some time, Immigration policy doesn’t allow for that.  All options require significant investment, either from yourself or institutional investors.  While those may be viable options, I can’t help but believe that raising money to facilitate immigration is a ridiculous idea.  Instead I’ll raise money if and when it facilitates the acceleration of an idea with traction.  At this point I simply don’t want to experiment and learn on someone else’s dime.  So instead, I’m going to return to Canada to start the next company.  I love the Bay Area, I have a truly amazing support network there, so I will be back, but it’s going to require time, investment, and a stupid amount of paperwork.


Over the last 3 years, the US has made it damn hard for me to spend 1) investment $ 2) acquisition earnings and 3) seed money in starting.  Most other people probably wouldn’t have gone through what I have and moved down there post acquisition, and most probably wouldn’t think about starting something down there again.

I think a lot of people read about the startup visa and have a theoretical sense that it sounds worthwhile, but they don’t see first hand what effect it’s having.  I’m sure most of you have never heard of Attassa but we’re just one of many lesser known foreign companies that tried desperately to get Uncle Sam to allow us to spend our capital in the US.  It really shouldn’t be that hard …

Moving on from Yousendit

It was just over a year ago that Rod, Dwayne and I joined Yousendit after they acquired our startup Attassa.  After much thought, I’ve decided it’s time to move on.  There’s a lot of amazing people at Yousendit who’ve made me feel completely at home.  For that, I leave with nothing but respect and thanks to the people I’ve worked with.  In addition to leaving some truly great people, the hardest part is leaving a green card process.  The thought of trading permanent residency for the world of H1B’s, B1’s, E-2’s and ultimately the whims of USCIS is a little sad.  The US needs to take a serious look at immigration policy.  I dream that in 10 years, people look back at this time and view it as archaic and asinine.

Paul Graham would say that true “hacking” is not science, it’s not math, but rather, it’s art.  It’s creating things.  A hackers tools are a compiler and an IDE rather than a canvas and a paint brush.  Call it what you will (I like the artist analogy since it makes me look way cooler, hipper, and trendier than I really am), but whatever it is, I love it. I also believe that if you define hacking as “seeing a vision and implementing it”, it becomes something very hard to experience outside of starting up.

In larger organizations, it’s necessary to avoid disaster.  Only a very small number of programmers can actually envision and then design software;  and it’s super hard to find these people.  So … organizations gravitate towards designing by group thought, mostly lead by PM.  In this world, developers implement the design and vision.  And this works since for larger organizations to win, they just need to suck less than other big companies.  You could argue that strategically this is the way it should be.  You’d be foolish to pin the corporate strategy on the design and vision of a few hackers.  But for startups, the corporate strategy IS the design of a few hackers.  That’s your only choice.  Companies like Google used to get away with a hybrid by encouraging hack days, 20% time, and innovating from within.  Their revenue / employee afforded the luxury to innovate from within while still producing the bottom line.  That’s rare.

Most hackers can’t “hack” for a living; much like musicians can’t play music for a living; they mostly hold down day jobs at bigCo to afford their true passion to build what they want on evenings and weekends.  But I’m in the fortunate position to step back and hack full time again.  For all I know, I may be implementing someones vision in 4 months, and I’d be ok with that.  It annoys me to no end hearing engineers complain about working for bigCo and their lack of ability to engage their creative minds.  What a first world problem.  But for the time being I can’t wait to get started …