I’ve been in full blow obsessive mode for a couple weeks now diving deep into a startup idea.  Forgetting where I parked the car … driving 5 minutes towards downtown before realizing I was supposed to going southside … waking up at 5AM unable to fall back to sleep … without sounding too much like a blow hard … that’s been life.

So I thought I’d take the chance to articulate what the last 48 hours have been like.  I think they’re typical of anyone starting a new tech company.

Sunday 4AM – Wake up, second guessing the domain we have registered.  I’ve received mostly positive feedback … but a few negatives from people I have a lot of respect for.  Also received mixed responses for the logo we had done on 99 designs.  Damn.

6AM – Still laying in bed.  I now have a list of 8 potential names written on the notes app of my glowing iPhone.

7AM – Lucy (my super awesome 2 year old) wakes up.  Spend the next 2 hours acting like I’m her age.

9AM – Go for a workout with lucy.  They have babysitting there.  Fully intend on running.  But I’m still obsessing about the name.  Crack open my lap top and start looking for domain variants.

11AM – Have registered 10 different domains.  Have grown a very unhealthy hatred for domain squatters and over priced international domain registars.  Suddenly godaddy doesn’t look so evil.

11:30AM -> 2PM – Acting like a 2 year old again with Lucy.

2PM-4PM – Lucy’s napping.  I’m emailing friends asking for feedback on domain names.

4PM – 8PM – More acting like a 2 year old.  We go over to a friends house for dinner.  I can’t help pitching them on the idea and getting feedback.  A huge part of me always feels like a duche doing this.  They say they love it, but I can tell they don’t really get it.  Damn, I need to work on how I communicate the idea, and just listen to them express their problems instead of just “pitching” the idea.

8PM – 1:30AM – On my computer.  Emails, catching up on hackernews and techcrunch for the day.  More emails to Yen Lee, we’re planning a CTO follow on event  to the one we had already. Have a 15 minute online chat with Dwayne about the importance of design.  He’s dropping knowledge bombs again.  Watching a Ng video about machine learning.  His lectures are pretty awesome.  Feeling pretty pumped about the new domain names I registered.  Spend an hour looking at muulabo’s api documentation for natural language processing.  Joined dribble,com.  I read somewhere it’s where designers hang out.  I want to learn more but after 30 minutes I’m sorta confused about it’s purpose.  Damn.  I didn’t write any code today.  Bed time.

Monday 8AM – Wake up, playtime with Lucy

9:30 – Drive Lucy to daycare, pull up a chair at a coffeeshop.  Start getting a bunch of responses about names.   Most of which are ironically favoring the original name.  Along with a lot of feedback, Josh Kerr points out that there might be a copyright concern.  Damn.  Spend about 30 minutes trying to figure out how the hell to figure that out.  Stumble upon the US Patent and Trademark database.  There’s nothing obviously conflicting with the name I’m happy with … but I still have a knot in my stomach thinking about evil Microsoft henchman.

11AM – an hour chat with Steve Wandler.  Love that guy.  General feedback on the idea.  Talk a lot about SR&ED, IRAP, mitacs, incorporating in Canada vs. the US.  He tells me I’d be crazy to not keep things simple and only incorporate in Canada.  That’s what Kevin Swan told me too … I’m starting to believe it now.

12AM – Go for a 45 minute run.

1PM – 4PM – Respond to a request for legal advice re: immigrating to the US from Canada for your startup.  My advice … talk to a lawyer.  Responding to people that have been kind enough to respond to my “Which domains do you like best” email.  I convince myself that I’m not harassing them … but rather giving the opportunity to shape a new company … even though I know I’m just harassing them.  20 minute call with a rep from IRAP.  Looks promising.  But damn, they need a business plan as a first step.  This is going to be annoying.  Spend 10 minutes writing an email to Rod summarizing my day so far.  End up responding about 5 times to my own email … keep forgetting to mention things.  Jennifer Turliuk points me out to a competitor in this space.  I’m feeling embarrassed cause I haven’t heard of them.  In the process of reading their techcrunch article I uncover 2 other competitors.  Damn.  But I convince myself that they’re not really going after the same pain.  So we’re cool.  If anything, this confirms the market.  Although that’s one of the things I love telling myself whenever I see a competitor.  I get that pit in my stomach again thinking about how hard it is to get distribution for consumer apps.  The competitors I stumble upon have decent value props, but essentially 0 distribution.

4PM – 8PM – Pick up Lucy, her Wendy and I hang out all evening.  Save for checking my email a couple times I’m completely offline.  As a side note … I seriously recommend that anyone having a problem with “work / life balance” should have a kid.  Wait … I don’t mean they should have a kid for the sake of establishing balance … I more mean that I don’t see how you can’t be balanced when you have a kid.  I have 0 problems completely detaching myself from work when I have a 2 year old tugging on my coat sleeve.

8:30PM – now – A 15 minute call with Ethan Anderson turns into an hour call.  Awesome to hear what he’s up to.  This is the first time we’ve connected.  Great feedback from him about the whole service provider space and some of the inherent challenges.  Brainstorm a bit about our respective ideas.  Awesome dude.  Feeling a bit overwhelmed about the idea.  Feels like there’s 3 very different types of products / pains we’re looking at.  Is that a sign of a good idea or bad idea, or an early sign I lack focus?  Damn.  Think I’ll spend the rest of the night thinking about where the real pain is.  Notice my square reader came in the mail.  Reminds me I really need to start coding again tomorrow.  Think about looking into a business plan for the sake of IRAP … but decide I need to blog about my day.  Voila.

 

I’ve been a fan of the paleo diet for a while.  Tonight, I’ve started another paleo challenge.  Anyone catching me breaking the paleo rules between now and Christmas wins themselves $100.  I allow myself the following affordances to the rules: coffee, an occasional social glass of wine.

For those unfamiliar, with the paleo diet, you essentially eat what presumably those in the paleolithic era would – lean meats, vegetables, fruits, and nuts.  Refined foods, sugar, dairy, and grains, are a big no-no.  The “science” behind the diet states that we haven’t been able to evolve to digest these non-paleo foods.

According to S. Boyd Eaton, “we are the heirs of inherited characteristics accrued over millions of years; the vast majority of our biochemistry and physiology are tuned to life conditions that existed before the advent of agriculture some 10,000 years ago. Genetically our bodies are virtually the same as they were at the end of the Paleolithic era some 20,000 years ago.”

That said, I’m a fan of this diet, not because of the quoted science.  It’s a bit wonky.  I’m a fan because if forms the basis of what any good diet has:

1. Simple rules:  They don’t get any easier than “eat only vegetables, lean meats, and fruit”

2.  A diet consisting of mostly vegetables, lean meats, and fruit.  It’s really hard to eat unhealthy just eating that.

In Omnivores Dilemna, Michael Pollan boils “healthy eating” down to 3 very simple rules: “Eat food, mostly vegetables, not too much.”   The key point in this is “Food.” Food isn’t highly refined and preserved food.  Food is what you find on the perimeter of a grocery store.  Food goes bad in a week (or less) if you leave it out.  That’s how “food” should behave.  This line of thinking absolutely resonates with me and my paleo diet leaning thoughts

I had the honor of speaking on a panel at AccelerateAB yesterday where someone asked a question to the effect of “How did you keep momentum throughout your startup?”  Here’s an answer given an evening to think about it.

I’m going to assume that at the root of the question was:

In a startup that had so many hard moments, how did we stay motivated and driven to keep grinding it out until finding product market fit?

I think for that, it’s pretty simple.  Almost all of the drive came from one thing.

Pride.  We wanted to win, and were too proud to relent.

We had ample opportunity to demotivate.  We ran out of money several times, had several flops for launches, and our Techcrunch articles never resulted in anything but a few thousand customers who abandoned the service quickly (sometimes because the servers failed to scale, and were now on fire).  We were even kicked out of the country once.

One thing that I think helped us was our ability to execute.  All 3 of us were technical, and Dwayne is without a doubt the fastest / most competent programmer I’ve ever worked with.  If we didn’t have an ability to get up off the mat and quickly, and relatively cheaply to try again, I think it would have been much harder.  This is one of the reasons why I hold so much value for a startup with an ability to execute like mad on product – house.

It sounds great to say that it was pride, our passion to succeed, and our ability to fight back that carried us through the entire journey.  But I’d be lying if I said that was it.  As bad as it sounds, I think that there were a few rare moments where we wanted to quit, and where motivation was really low.   But what motivated us in those situations was simply a fiduciary responsibility we felt for our investors.  I remember talking about this at length with Rod, in particular the personal pressure he was feeling.

When you raise money, you raise money from a fund.  Your investor (unless it’s an angel) isn’t investing their own money.  But yet, at least for me, it’s impossible to not feel a personal connection and responsibility to the man / woman investing in your company.  I think people need to be aware of this when raising money.  It’s something you hear mentioned, but probably not enough.

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.

Concluding

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 …