CREDIT: @striatic on flickr 

Are Startups Cool?

Getting Into Startups With Your Eyes Open

An old friend of mine dropped into San Francisco recently with her team from a Big Four firm, and while we caught up at the Owl Tree in TenderNob, she said the following:

“I don’t really get what you do… but it just sounds cool. Anything with ‘startup‘ in it sounds cool… so good job!”

That’s pretty much how the world thinks about startups right now.

I think that’s an unhealthy way to think about startups.


I didn’t get into startups because they’re cool, but I have a sense that people are starting to do just that.

A tough economy and bleary professional prospects have made even my most risk-averse friends consider leaving traditional (and stable) jobs to start a startup. The excitement surrounding early stage tech is so high right now that for some people “sitting on the sidelines” has become the risky career move.

That’s insane. The idea that starting or joining a startup is a rational career move is counterintuitive at best, scary at worst.

Anyone who’s started a startup would likely agree that last reason they got into this game was because they were thinking about their “career”.

Broke, Dead Broke

I’m not writing from a pedestal here, having sold a startup company for millions. My first startup is in its third iteration having struggled to find sustainable traction. My incredible co-founder now runs that company and I’ve joined a friend’s team to help them grow.

To be clear, my first go as a startup founder left me broke and more than a little bit beaten up.

And when I say broke, I mean broke. The kind of broke that people get uncomfortable talking about.

It was the kind of broke that left me unable to pay rent in Vancouver, having relocated there following our seed funding in 2009. Effectively homeless after foregoing a paycheck for two years, I ended up living on an entrepreneur friend’s couch for more than six months in late 2011.

At 30 years old I was living on someone else’s couch without a dime in my pocket, working on our startup at every spare moment.

That’s not very cool.

Passion & Pain Are Close Friends

Every day for about a year, each morning presented two major challenges:

1. Relentlessly search for a successful business model and co-lead our team in pursuit of our vision.
2. Find a way to survive by acquiring food.

If that sounds pretty basic, that’s because it was. When was the last time you worried about eating?

Every morning, I woke up on the couch in my friend’s 1,000 square-foot apartment, grabbed semi-clean clothes out of my backpack, took a fast shower and went to the office wondering how I’d afford lunch that day.

Oh, did I mention he lived with his girlfriend?

I reached a point at which I’d ration out my week on less than twenty dollars. I was forced to ask for help from other entrepreneurs who would buy me meals. I couldn’t always feed myself.

Unable to pay bills, I stopped doing so. My pre-startup credit card debt taunted me via collection agency voicemails. My phone went dead.


The fallout of going really broke is immersive. You lose your feel for the normal day that most people experience. As a founder you have a sense that you’re in that position as service to the dream you’ve committed to, so you’re left with nothing except for the work that you’re doing.

And so you work. All the time.

There’s nothing else you can afford to do.

Let’s Not Forget Startups Are Really Hard

The reason I feel it’s important to highlight the hardest parts of my particular founder journey is because not enough of us talk about the ugly bits. Not everyone has this kind of extreme experience, but startups can be brutal.

They can be mentally brutal in ways that can only be overcome if you believe in what you’re doing. Emotionally brutal in ways that can only be overcome if you truly love the company you’re trying to build.

A startup unequivocally means short- and long-term uncertainty. They involve real, tangible risks.

A startup can mean pain and embarrassment.

A startup can even mean homelessness.


I think it’s important to recognize how hard it is to get a startup off the ground, and I do believe that the endeavor is incredibly admirable.

Anyone who’s pursuing their dreams deserves credit for the risks they take to achieve them.

With that being said, however, I also think it’s important to recognize that startups certainly aren’t for everyone.

In fact, they’re not for most people.

It’s important to know that the real risks you’re taking on with a startup include the catastrophic kind. There are entrepreneurs who’ve lost relationships to their pursuits. They’ve lost homes and financial security and certainty about where they’ll live and work three months down the road.

There are entrepreneurs… good ones… who’ve lost their life to this crazy ride.

Let’s never forget this, people.

Let’s never let the cool factor bring people towards this kind of life for the wrong reasons. Let’s never let someone find themselves with the world crashing down around them without them having been prepared for that reality.


In my mind, startups are cool. I love what I do and want to do it for the rest of my life.

I just know that there were moments when things got really, really tough when it felt as if the cool factor was all anyone talked about. I’m not here for the wrong reasons, but if I were it would have ruined me.

I want anyone contemplating this journey to do it with open eyes.

Our community is responsible for the picture we paint, so I hope more of us continue sharing the real stuff in an effort to complete the painting as best we can.