Derek Shanahan

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.



So damn true. My startup ruined me. From pissing off every last employee when we went broke, to angry angels and a family that won't speak to me, the startup life just plain sucks. People also don't talk about how hard it is to get a job after your startup folds. When you've got 3 years at a failed startup on your resume it's like having a 3-year black hole. Even though I worked my hardest, learn the most, accomplished the most--despite ultimately failing--won award, got patents, made cool stuff, non of that counts to employers who just want to see a slow and steady work history. Since I haven't yet recovered, I can't say whether I will one day look back at the experience with fondness. Right now, I hate everything about that company I started.


Dude - I stumbled onto your blog and this is awesome stuff.  Your speaking my language.  I can honestly say I've been a part of startups for the past 5 years and it is no cake walk at all. Startups are hard work.  And when you get started with little to no cash in the bank, they become a bear.

Thanks for sharing this - excited to read more of your work. Cheers!


ktschoenberg 1 Like

Incredible post Derek. Sounds eerily familiar to when I lost $200+k and spent my last $6 on a pizza.  Did I mention that I also had 2 kids to support at the time?  Memories of those days keep me focused..Startups are not cool, and the fear scares the shit out of most (including me)..but you just have to tell fear to fuck off and keep moving forward...

saradavidson 1 Like

Incredible post, DShan. Thanks for being vulnerable enough to share your own experience. I can totally relate. ;) You also didn't touch on the toll it can take on your health, aka no sleep, countless all-nighters, crazy amounts of stress, no time for exercise, unhealthy eating, and then filling your veins with caffeine and cigarrettes to combat all of the above. It took me a year to recover from the burnout. Certainly not glamorous. But it was quite the experience. 

So proud of you for going for it, and excited to catch up soon!! :) xo

dshanahan moderator

@saradavidson Sarah with an H thank you so much. That almost rhymed. I'm actually hoping to dig deeper into the moments - the health, the mental, the social experience. It's crazy, and it's worth it, but it's crazy and most people don't every experience it. I'd say I'm about a year "out" and just now itching to dig into the details. Talk soon? xo

cr8ivecodesmith 1 Like

This is definitely true. Not everyone understands why we're doing what were doing. The "road less travelled" was less travelled for a very good reason. Thanks for the awesome post! :)

Caryn 1 Like

I love the honesty and vulnerability in this post. I agree with you that a lot of people just see the glamour of the successful startups and don't see the hard work, sacrifices and pain that goes into *hopefully* getting there. 

I appreciate you showing the real - non glamorous side of the startup world. You're creative and inspiring I'd love to chat or skype with you about my endeavor and get some advice from you. Bummed we never got to connect while I was in Chicago- I'm in DC now. Any plans to come out this way?

rtanglao 1 Like

wow. great beautiful back to reality summary. thanks! miss seeing you here in VanGroovy. If you have time, love to grab a coffee with @econwriter5 next time you are in Vancouver!

dshanahan moderator

@rtanglao Roland, thanks so much. I miss VanCity bad. Just had a long catch up with Anthony about the city and what's going on around town. I'm hoping to stop thru this summer and would love to connect with you and @econwriter5 for some amazing coffee:)

tjt 1 Like

Great post. Starting to realize that this type of insight needs to be published more and more. Definitely not an easy thing to be so open about. Even as an early employee of a failing/failed start-up I found it hard to be honest about the current state of the company, or my personal well being for that matter. But a group of people buying into a founder's vision for as long as they possibly can, regardless of if there is money in the bank or not , is very inspring thing. Kudos to you, man.

dshanahan moderator

@tjt Appreciate you reading. You're right, the tribe you build in the early stage can be really inspiring, even if it is hard.

brandonzeman 1 Like

Damn. I would have bought the shit out of some meals for you buddy. Been meaning to catch up with you but seems like you've been kicking ass in San Fran.

dshanahan moderator 1 Like

@brandonzeman Dude you're awesome. I'd love to catch up - let's see if we can't cross paths in Chicago this summer.

CKana 1 Like

Wow D. Great writing. Great post. Lord I had no idea it was *that* bad. You did a great job of keeping your chin up and putting a positive flow on the whole thing. I wish I would have known that you were stretched so thin - I would have bought you a ticket to go see a show or at least a few beers. ;) Means everything to me that despite your struggles, you made it to our wedding. I'm sure that wasn't easy to pull off.

I am definitely one of those naive people that thinks everything about start-ups, and you in general, is ultraubercool. Thank you for being so honest and for showing us the flip side, the real side. Very interesting and inspiring. You are a dedicated dude. I am so damn proud to know you and to love you. xo

dshanahan moderator

@CKana Sweet Cha, first of all, you were a big part of making it all work - you got quite a few late night emails spilling if I remember. Those were as much for me as you. The wedding thing's a whole 'nother post. I struggle with the ones I missed, but yours was non-debatable. Duh:) 

You've given me more than any show or beer could. Love you endlessly.


  1. […] two years working on a startup that never really got the kind of traction we were looking for. I went broke in the process of learning quite a bit (as anyone will if they crack at it for two years). We made plenty of […]