Prison Break: Escaping From Shawshank Inc. For A Startup

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Prison Break: Escaping From Shawshank Inc. For A Startup


I first laid eyes on Andy Dufresne during his orientation session here at the Shawshank Software Corporation. To tell you the truth I didn’t think much of him—I figured a couple of 4-hour mind-numbing “planning” meetings and he’d break down in tears. That’s what happened to most new developers at Shawshank. Sometimes it took a day. Sometimes a week.

Rumor had it Andy was some hotshot programmer fresh out of MIT. Usually someone that talented can write their own ticket, so why Andy was at Shawshank, I can’t say. But I’m betting it had something to do with a recruiter. Or his parents. That’s how a lot of programmers end up at Shawshank, pounding out mindless code like convicts churning out license plates. “I’m better than this,” they all say straight-faced. “I don’t belong here.”shawshank

In the beginning, Andy hardly said more than a few words to me. It was obvious Andy wasn’t like the others that were passing through Shawshank’s gate. Most fish start whimpering as soon as our CEO, “Warden” Norton finishes his your-butt-belongs-to-me speech, and the goons from HR begin their interrogation routine. Andy, though, had a quiet way about him. He was not like the others. It’s safe to say I liked Andy Dufresne. I liked him a lot.

It was a month before Andy actually spoke to me. He said that he heard I was a man who could get things done. Which was true. Shawshank required approval forms in triplicate for every little thing, and I was the only one on the team that knew where to get the forms, and who to submit them to. When I nodded, Andy slipped me a yellow Post It note with a list of items—pens, dry erase markers, white out. “And a large poster of Rita Hayworth,” he added.

rita hayworth

Warden Norton took notice of Andy, and soon he had Andy doing all sorts of pet projects, like working on the Macro Infrastructure Guide to Releasing An Incomplete Engine (MIGRAINE). I can’t even count all the Fridays when I’d be getting a drink from the bucket that replaced our water cooler, and notice Captain Hadley standing just outside Andy’s cubicle, giving him another shakedown he didn't deserve.

The fact that laptops were invented years ago or that if we upgraded the computers developers worked on more than once every 4 years, we might get the Eclipse IDE to load in less than 2 minutes was not something we talked about at Shawshank. Better just to start off a build and stare into space than make waves. Inmates at Shawshank are supposed to read specs and write code. Thinking was not encouraged at Shawshank.

Some nights, I’d find Andy sitting there alone in his cube with Rita Hayworth looking down condescendingly as he gamma tested Shawshank’s latest software release The fact that Andy didn’t know that most of his code would never actually get used by anyone was a blessing. It allowed him to carry on. Ignorance is bliss at Shawshank.

The Warden liked to use motivational tactics that he claimed were invented by Japanese monks, but we since discovered he had read about in an in-flight magazine. Like helping developers break-up the monotony of their long day by scheduling mandatory meetings every three hours.

Andy was probably the toughest screw to ever do a turn at Shawshank Software, which only made me more curious about him. “Hey, Andy, what’s up with Rita Hayworth there?” Andy glanced behind him. “Rita? Well she’s a symbol,” he said. “A symbol of a better place out there, where you’re appreciated, where people like coming to work, and you get to build products and release them to actual users.”

I thought he was crazy. “That kinda thinkin’ will drive you insane, Andy. There ain’t nothin’ like that out there.” Once you get sentenced to Shawshank, there is no other world. After a while, the place gets to you so you can’t function beyond the tombstone-grey cloth panels of your cell. Andy wouldn’t hear it—said he’d prove me wrong one day. I had no idea what he meant and thought he might be cracking up right in front of me. The circles under his eyes looked darker than usual.

Staring into his monitor, Andy got in the last word before I walked off. “There’s only two things you can really do in a place like Shawshank,” he said. “Get busy livin', or get busy dyin'.”

Get busy livin', or get busy dyin'. I couldn’t escape Andy’s words.

A week later, Andy was gone. The Warden and Captain Hadley were tearing his cubicle apart when I showed up. I didn’t know what was going on until they threw Andy’s resignation letter at me and then ordered me to take down that stupid picture of Rita Hayworth.

shawshank rain

Andy’s gone. I was still in disbelief. Andy Dufresne—put up with a world of crap, and escaped to the better life he knew existed outside these walls. A world where developers got Macbooks with SSDs and dual monitors. Where programmer productivity was not an oxymoron. And most importantly, where you got to actually write code that mattered to millions. I took the small slip of paper I found behind the poster of Rita. All it said was “”. I smiled.


Are you an awesome developer trapped inside a place like Shawshank Software? HubSpot can maybe help you break free and join a startup.  [We're also paying referral bonuses.  $1,000 for every year of time you've served in a big company.]

Posted by Dharmesh Shah on Mon, Aug 01, 2011


Outstanding Dharmesh. Beautifully written and with much truth in it. You may be the best reason to break out of Shawshank.

posted on Monday, August 01, 2011 at 8:59 AM by arjun moorthy

Anybody got a rock hammer?

posted on Monday, August 01, 2011 at 9:29 AM by Denise Reiter

Love "Shawshank" and I've had the startup bug for some time. Nice twist on both.

posted on Monday, August 01, 2011 at 9:39 AM by Tom Denison

After this reminder I'm busy living now!  
Thank you

posted on Monday, August 01, 2011 at 9:39 AM by Sandra Donoghue

Very creative! Thanks for breaking the monotony... :)

posted on Monday, August 01, 2011 at 9:40 AM by Erin Currin

Excellent piece. And what are you doing over there? Get yourself an editor and start shooting best sellers!

posted on Monday, August 01, 2011 at 9:42 AM by Chiefenette

Ditto to all the above...I'd like to get to know you. 

posted on Monday, August 01, 2011 at 9:44 AM by Robert Munoz

Holy cannoli. That's the best job posting I've ever read. And payment for time served? Classic.  
Nice job.

posted on Monday, August 01, 2011 at 10:04 AM by Kathy Ver Eecke

Very creative.

posted on Monday, August 01, 2011 at 10:07 AM by Mohib Sheth

Thanks for the kind words, folks. 
This is not the usual kind of article I post to OnStartups.  
Hope you're planning your escape.

posted on Monday, August 01, 2011 at 10:09 AM by Dharmesh Shah

Just another story about some sucker who escaped the Shawshank Software Corporation by resigning. Sorry, Andy -- you did it wrong. A better man would have taught his company how to innovate, how to sprint, how to be productive. Leaders of Big Companies don't want their workers to be mired in red-tape and bureaucracy; they want them to be just as agile, fun and creative as workers in a small start-up. But don't put that all on their shoulders -- you need to help lead the way.

posted on Monday, August 01, 2011 at 10:16 AM by JP Seabury

Great piece. This is applicable far beyond the walls of programmer prison! Any curious person who has worked at a very large company has either known, or become, an "Andy." 
The fact that big companies cannot see this fact, is exactly why they are vulnerable to small companies with big ideas. 

posted on Monday, August 01, 2011 at 10:16 AM by Dan Walter

Very well done. You added 3 dimensions to a routinely 1 dimension type article. Keep it up,

posted on Monday, August 01, 2011 at 10:23 AM by Coach Michael

Great movie; Great article. Thanks Dharmesh.

posted on Monday, August 01, 2011 at 10:28 AM by Jennifer Marotta

Nice article, that is one of my favourite films ever. I have broken free from a big corporate, and loving life..

posted on Monday, August 01, 2011 at 10:32 AM by Joe Haugh

very creative piece....quite motivating

posted on Monday, August 01, 2011 at 10:54 AM by Chaitanya Gupta

Macbooks & dual monitors?  
Try the real startup life--emachines laptop with broken monitor and after-factory ram boost -- with the blade marks around the sides to prove it. and missing o key, slow Android emulator and throwaway test machines with a tangle of cords in the bedroom.  

posted on Monday, August 01, 2011 at 10:59 AM by Aaron Evans

Well, i am confused or being very critical.. Luved shawshank but eh..andy was there for a reason (he commited a crime and was booked under a law) and u know he looted the warden robin hood style..r u encouraging that Mr Shah..Secondly if everybody is going to be redeemed from shawshank..then a prison shawshank or any shawshank will exists. If everybody will be free starting their own, then who will work for themselfs.. I just feel Mr. Shah is being a nice marketier, and a Andy for his Hubspot..and also lucky to be accepted by google..but it should not be mistakenly take all to be andy.. All business needs andy and all andies need businesses.. Will hubspot afford to loose a Andy and taken some millions of you Mr Shah, the warden..(smile..)..Sorry for this analogy.. 
Well wisher and bit critical thinker

posted on Monday, August 01, 2011 at 11:04 AM by Karmasoftra

Great writing but it should be pointed out there there a lot of unemployed and under-employed programmers who wish that had a job at "Shawshank Software." 
It's easy to say "do a startup" ... but not so easy when you have a family to support.

posted on Monday, August 01, 2011 at 11:45 AM by William D. Volk

Haha, great analogy and cultural reference! Entertaining and insightful.

posted on Monday, August 01, 2011 at 11:52 AM by Jonathan Jaeger

@JP Seabury, 
I don't know which large companies you've worked for, but trying to get them to change and be agile as a software developer is like the cooks trying to steer the Titanic away from the iceberg...ridiculous. 
As for @karmasoftra, your first mis-statement was that Andy was guilty of the crime he was sentenced for...he was not. Regardless, Shawshank was a bad place because they treated the inmates (even the guilty ones) inhumanely. Secondly, the point Mr. Shah is making is that if you're stuck in a large company, AND you fit the criteria for a startup (i.e. MIT hotshot, outside-the-box thinker, etc.), then you should not waste yourself there and either start your own OR find a smaller, more nimble, and better fitting environment to work at. Your last mis-statement is also an insult that HubSpot is "lucky" to be accepted by Google. As if hard work, determination, perseverance, and sacrifice by Mr. Shah and his entire team to accomplish such a feat. I challenge you to do better. 
Kindest regards, 
D. Kazanis

posted on Monday, August 01, 2011 at 12:10 PM by Dean Kazanis

A motivating and creative article.It is insightful!!

posted on Monday, August 01, 2011 at 12:24 PM by Emilie

Very well written...clever, entertaining and informative which makes it refreshing. My partner (who writes the #10 top IT technical analyst blog in the world)and I run a service that helps storage industry startups hire experienced people from the big companies. Startups are at a severe disadvantage when you consider the millions of dollars large companies spend on recruiting talent and for premium placement of ads in search engine results. We limit our practice to helping only startups and emerging companies. It's too easy for a really talented achiever to get stuck in a big company working to make something for themselves - a salary - when they could be working to make something of themselves.

posted on Monday, August 01, 2011 at 12:51 PM by Ray Holley

While there is some truth to what you speak, I can tell you from our experience as a a founder/engineer (of 2 startups) that engineers need to think about more than code/technology/coolness. They need to think about health insurance, benefits, having a safety net, having mentors who can help. Bunch of folks I talked with in startup have the mentality that they will hire and fire in 2 weeks. A company, small and large, needs to give engineers room/time to grow instead of just firing them. This is what you get in larger company. Of course, if you are 21, and have no family and relatively good health, Startup may be just the right thing (or older person who kids have gone to college and mortgage is almost paid off). 

posted on Monday, August 01, 2011 at 1:03 PM by alok sinha

thank friendships, unforgettable, you get healthy and long life

posted on Monday, August 01, 2011 at 3:33 PM by yusuf toklu

A very interesting article. Shawshank happens to be one of my favorites.

posted on Monday, August 01, 2011 at 9:11 PM by Reginald Jackson

For Entrepreneurs its a guide, a path shower, shaker and mover article

posted on Monday, August 01, 2011 at 9:37 PM by Lava Kafle

Nice article...

posted on Monday, August 01, 2011 at 10:21 PM by Ajay

That was really amazing! I really liked the movie and so this article now.. :)

posted on Monday, August 01, 2011 at 11:13 PM by Swetha Padakandla

A good perspective from a different angle altogether. I agree with the overrall idea of breaking free if u are upto it.

posted on Monday, August 01, 2011 at 11:30 PM by Srinivas D

Wow, Dharmesh! This is an awesome & inspiring article. I have dabbled in startups but to keep the mortgage & family going, have been trapped in the vicious Shawshank world!  
Any openings in India or plans to open up shop in India? I would love to help you establish Hubspot's presence in this part of the world!!! :-)

posted on Tuesday, August 02, 2011 at 12:07 AM by Deven Shah

You could have used more honest means to attract awesome developers to Hubspot. 
You shouldn't punish your captive audience so severely. 
Following you may be a crime,but the punishment is totally disproportionate. 
God bless you and your audience, 

posted on Tuesday, August 02, 2011 at 1:07 AM by Shyamsunder Panchavati

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posted on Tuesday, August 02, 2011 at 4:07 AM by ugg boots

Loved, loved, loved this! As someone who has been stuck in the grey walls of a prison cubicle, this was hilarious! 
I am hoping to break out soon myself... the startup dream lives!

posted on Tuesday, August 02, 2011 at 11:25 AM by Julie Benson-Grant

i hop 2 break soon

posted on Wednesday, August 03, 2011 at 6:52 AM by stephen osure ofwaya

Nice article Dharmesh, nice comparison . Just one difference - no on is holding you back in real life SS.

posted on Wednesday, August 03, 2011 at 7:32 AM by Maries

Yes, my escape really does feel like I'm digging through 10 feet deep brick walls with a spoon and a tiny hammer.

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My little brother does the best Morgan Freeman impression, so I asked him to read the entire post to me in the car while I drive. We both couldn't stop laughing the entire way through. Awesome post!

posted on Thursday, August 04, 2011 at 12:20 AM by Alex

Thank you for this!!!!! 
That's all I am going to say

posted on Thursday, August 04, 2011 at 9:58 AM by GJimenez

Hi Dharmesh -- This is so good. I'm finding so many great resources for MOSO (micro owners/solo owners). I appreciate having reading the stories of likeminded people like you. Though our visions are different (mine to fuel the aspirations of MOSO with editorial content and other things that may spark the passion of people stepping out), I'm glad to know I'm not ALONE.

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