All posts tagged playerize

Are Startups Cool?

I was catching up some friends and someone at the table said, “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 sad economy and bleary job prospects have made even my most risk-averse friends consider leaving their jobs to join 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 straight up crazy.

Any startup founder would agree that the last reason they got into this game was because they were thinking about their career.

My Story

An early draft of this post didn’t include much about my own experience and the few I asked to read it suggested I include a bit about my own experience. I think they’re right in that it’s helpful context. I’m not writing from the top of the hill, having sold my company for millions. My first startup is still alive but it’s a company we’re still pushing to find real success in.

I went broke as a startup founder. Dead 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 round. Unable to pay rent, I ended up taken in by an entrepreneur friend to crash on his couch. 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.

Every day, waking up presented two major challenges:

  1. Find a way to push our startup towards success and find a revenue model that worked.
  2. Find a way to survive by acquiring food.

If that sounds basic, it was. When was the last time you worried about eating enough?

I reached a point at which I’d ration out my week on less than 20 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 credit card debt began to build all around me. My phone went dead.

The fallout of going really broke is immersive. You lose your sense of the normalcy most people experience. You’re doing it for the dream you’ve committed to, so you’re left with nothing except for the work you’re doing.

You work.

You have nothing else you can afford to do.

It’s brutal. It’s not glory.

A startup means uncertainty. Startups mean risk and pain and embarrassment. Startups can mean homelessness.

So…are startups “cool”?

Let’s look at the good and the bad. This is by no means an exhaustive look at startup life. If you’re in it, please share your insights in the comments for my mostly non-startup audience.

The Good Stuff

  • DREAMS – Creation IS cool: Building something new is cool. It’s as cool as writing a hit song or making a beautiful movie. Mainstream culture is now idealizing Sean Parker in the ways that they used to idealize The Rolling Stones.
  • INNOVATION – Risk aversion drives innovation: Startupheads are risk averse and face uncertainty in a way that most people don’t have the stomach for. Facing failure forces people to keep on pushing their boundaries. The survivors persist because it’s what they’re meant to do. That selection process benefits all of us.
  • BENEFITS – Work your own hours, unlimited vacation, blah: Startups build their own culture from the ground up, and we are lucky to have that fortune. It’s not 9 to 5. It’s a life very driven by results.
  • COMMUNITY – Altruism makes it all possible: Startup people are passionate. That passion birthed an industry full of collaboration and support that puts other industries to shame. Newbies in the startup world are met with encouragement and mentorship. It’s a competitive world, but it’s generally more friendly than other industries (I’ve worked in high finance and law, others can comment otherwise).

The Real Stuff

Here’s a bit about the stuff that isn’t “cool”.

  • DREAMS – Uncertainty is horrible: Imagine never knowing if you’ll have a job tomorrow. Or if you can pay your bills next week. Founders have it the hardest, but no matter where you are in the ecosystem, you’re always living a life that’s got no guarantees. Startups aren’t a career, they’re a lifestyle.
  • INNOVATION – Failure, always: In a startup you’re always fucking everything up. There’s nowhere to hide; you will feel bad at your job. You will often go to sleep knowing you could have done more. You will always know how much more there is to do. Everything but work can become “not working”, if you aren’t working.
  • BENEFITS – Paychecks are unstable: In Startupland, salaries are kind of a joke. Being an early team member on an unproven technology venture means you may find yourself elated every time you get paid. Financial instability is pretty consistent and it affects nearly aspect of a startup team members’ life.
  • COMMUNITY – You don’t complain: Whether you’re a founder or an early employee, every early stage ship is a rocket ship, and saying otherwise is sacrilege. There isn’t a lot of room in the startup culture to complain about your job. Startup jobs aren’t jobs. They’re tribe memberships.

I think it’s important to recognize that joining a startup is an admirable endeavor, but it’s equally important to acknowledge that it’s not for everyone. In fact, it’s not for most.

Startup work is a mishmash of incredible strength and passion living right next to complete uncertainty about a final outcome.

That uncertainty is the result of a 99% chance of dying early. Have you ever taken a job with a company you expected to fail?

That’s a prerequisite to working in Startupland.

I’d love to hear more thoughts on the hype I’m seeing around being a part of Startupland. We need to talk about how hard this is. We need to recognize that we’re all choosing to struggle.

If we deserve the accolades that we get when we succeed, we should honor and celebrate the challenges we take on for what they are.

Thoughts?

Where I’ve Been & Where I Am

A big thanks to everyone who still finds me invading their inbox or RSS reader.

I’m going to be writing a lot more going forward, but things will change a bit. It’s like that time you told your dog she was going to the park and really you were taking her to the vet.

(Your intentions were great, by the way.)

I’ve always written extensively about my relationships on this blog in the past, and I’m not sure that will go away. I can’t really write without including the deeply personal stuff.

But…I am sure that I’m a different person than I was when this blog started. I’ve gotten into the frame of mind that nearly anything is possible if you dive in head first, learn as much as you can as fast as you can, and stay close to amazing people.

The last few years have been transformative, and I’m passionate about the role that technology plays in our lives. I need to explore that with you, and I hope that while I do that it will benefit you (no matter how much you think about tech).

As to the title of this post, I’ve been through the amazing process of being a first time startup founder. To all the people out there who’ve started businesses or hope to start one some day, I’m going to do my best to share my experience (finally).

Today, I’m working on another startup that two friends founded, hell bent on helping them turn their already measurable success into a true game changer. It’s brought me back to San Francisco, a city I adore on every level and a community I’m deeply excited to be a part of.

Going forward; moar writing.