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.