Entrepreneurial Lessons from the Coolest Man in Prison

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Entrepreneurial Lessons from the Coolest Man in Prison

10 Secrets to Lifelong Happiness on a Mexican Beach

It’s a favourite film of mine, and has ranked for years as the number 1 film amongst western cinema goers. So there has to be something very special about Shawshank Redemption and the character of Andy Dufresne.

Something so special, that we can apply this hero’s qualities to business and be a winner just like him. Considering he spent 19 years in a violent prison for a double homicide he didn’t commit this may strike you as a bit weird.

So I’m going to take you on a journey with the coolest man in prison up to his escape and new life in Mexico and show you how his qualities are the very ones you need to be a successful entrepreneur.

#1 Play the Long Game

Andy Dufresne is serving a double-life sentence. There is no overnight success ‘hack’ when facing 50 years inside especially in Shawshank a violent micro-society. It’s Andy’s willingness to take small daily actions over 19 years that eventually lead to his wealth & freedom. He achieves the hipster dream. The final scenes of the movie see him driving over the border to Mexico where he spends his days on the sandy shores of the Pacific Ocean, renovating a fishing boat by hand.

But what got him to this idyllic life?

In the first scenes we see Andy arrive in prison & be very quiet. He observes, listens and builds his knowledge of both prisoners & guards before developing a plan. In other words, he does his research.

Business Lesson 1: Do your research & take your time over it, not as a procrastination tool but so that you are fully aware of your niche & avatar before you develop plans & build products.
Nothing sucks on your time more than to go blindly into battle. In fact it can suck on your money too. I developed a ‘quick’ product which cost me £10k (about $15k in USD) and it completely flunked because I forgot the first rule of business – never assume, do your research, ask the marketplace what they want & deliver the solution they are looking for.

#2 Have Useful & Ethical Friends

Which may sound bizarre when talking about prison culture but there are definite choices between good, Red & his tribe and evil, The Sisters.
Andy’s first friendship, and most enduring, is with Red, the man who can get things – very useful when you want a rock hammer & babe posters. Notice though that Andy is willing to pay the going rate, a 20% mark-up for what he needs rather than expect mates’ rates or even free.

Business Lesson 2: When you first start out as an entrepreneur you will meet many other hungry entrepreneurs and while joint ventures, helping each other can be awesome, you can also end up doing business with the wrong type.

This doesn’t just mean crooks, though there are plenty of unethical liars in business, but it can also be that their personality type doesn’t sit well with yours or that their skill set is not as extensive as you initially thought.

Another lesson I have learned from this comes from Maya Angelou, to paraphrase, people show you who they are when you first meet them, you just don’t believe it. Now although I am a massive fan of strategy & logical thinking, I am also a fan of trusting your gut and not working with people who do not feel right. And if you do fuck-up on who you choose to work with, get out fast.

Obviously I am warning you of this because I did neither in the past. I was blind to my own influence & how people could use me & contacts I had worked hard to establish but lesson learned, now I have a tight team & am very selective on who I bring on-board.

This also links to point #4 but first let’s talk about how we form relationships and loyalty with our equals.

#3 Treat Your Peers

Well it is not only Andy’s quiet, deliberate nature that helps him form strong bonds with his chosen tribe, but it is also his generosity. When negotiating with Captain Hadley, Andy’s first thought is to secure the work gang ice cold beers.

“We sat and drank with the sun on our shoulders and felt like free men – as for Andy – he spent that break hunkered in the shade, a strange smile on his face, watching us drinking his beer”

The power of this scene is when we realise Andy doesn’t drink therefore at this moment in time he does not benefit at all by helping Captain Hadley avoid paying tax on his windfall.
Business Lesson 3: too many entrepreneurs are full of take-take-take. I get it, money is tight, they are desperate to succeed, and they are very self-focussed. However you can be all of those things and still be a ‘giver’.

Treat others well, whether that’s in helping them or financially.

When you are an entrepreneur many, many people will offer you free in the hopes of getting your business in the future.

You may well do the same thing.

How does it feel when nothing comes of it? It sucks big time. You get burned out & are unable to pay your bills. So treat others how you would like to be treated. Only be cheap, if you want to be treated cheap.

But pay your dues. If no payment was asked for, or wanted, send a decent gift.

Same goes for colleagues – you may not be able to pay the going rate for your assistant(s), so reward in other ways. Over the last two years, people I have worked with have received champagne, books, flowers, thank-you messages, bonuses, free training courses.

Do your best by people at all times – you will be rewarded by hard-work & loyalty.

#4 Know Your Influencers

While being friends with Red this has many benefits for Andy, he also knows to implement his long-term plan, he needs the guards & prison warden on side. Through word-of-mouth & networking, Andy’s expert status as a finance whizz grows.

Within 2 years he is fully trusted with everyone’s tax returns and Warden Norton’s book-keeping. His expert status gives Andy access to know & book-keep every dollar of corruption money and he is even trusted to undertake the banking.

“I’m a convicted murderer who provides sound financial planning

Business Lesson 4: The power of Influencers cannot be underestimated. Those higher are the greasypole are human & were once you. So have some balls & talk to them BUT not about what you want but how you can help them.

Very early on in FPCR I made a video documentary with Ben Coomber, an Influencer in the niche for that product. The making of the documentary cost me quite a bit of money as did advertising & promoting it. But the pay-off was worth it. I received some business feedback, unasked for, by Ben which was incredibly helpful and my own profile was raised by my association with him.

Ben was not the only Influencer I became friends with. You see you can identify current influencers through using social media well, Facebook & LinkedIn being good sources of information when you don’t take everything at face-value & do some digging.

Rising Stars – You also need to be friends with rising stars. Now they are not always as easy to identify, it might just be that you like them & their attitude…just ensure their attitude includes endless hard-work & driven focus and not Facebook glamour. Do not concern yourself with those seeking fame & adulation they are in it to win a popularity contest. Question why that might be on a psychological level and what that will lead them to do on a business level. Choose people with a strong why & good values.

Chris Burgess, Lift the Bar and Luke Johnson & Lawrence Judd of Shredded by Science, also became friends because I admired their work ethic & values. They are just really nice guys who do their best with massive action backing up their words.

Over the last two years, unsurprisingly, their starts have risen. They have greater reach & influence. My business is one they recommend. In fact their members get a 50% discount because I admire their values & the values of the people attracted to their tribes. Another side-note, if you love a player, they attract players to their tribes. Like attracts like. Anyway, 40% of FPCR business comes from LTB & SBS referrals. Awesome for me but also something for you to remember, if you choose your rising stars well, this may have future dividends you didn’t imagine at the time. Just don’t go into it with that in mind, that’s a surefire way to fail. Be generous & be genuine.

#5 Take Risks our hero takes many risks

The most dramatic being on the roof when questioning Captain Hadley at one point Andy is seconds from being thrown off the roof for impertinence.

Throughout the movie we learn of other risks, for example the smuggling in of the rock hammer, its concealment in a bible, the escape tunnel hidden by Rita Heyworth (and others), the depositing of stone in the exercise yard, the opening of false bank accounts & keeping a second set of books. Without taking risks Andy would never have escaped to Mexico a rich man.

Business Lesson 5: business is never safe. If you need security do not go into business. To succeed you will have to take risks, many of them financial. You have to be willing to put it all, and sometimes more than all, on the line. When starting FPCR, I was a single mum of 3 with £15k in the bank after spending a third on a mentor, I had £10k ($15k USD) left which was quickly swallowed by development costs & marketing. At one point I was maxed out on credit card, loans & overdraft to the tune of £25k ($40k USD) and that was on top of my original investment.
It could have gone badly wrong. I was in eternal doubt about what I was doing. I felt sick with worry for a good 6 months.

And yet, the strategy, the marketing, taking action, did pay off. Only a year later, I was taking my girls on a three week vacation to Greece, having already bought a new car, remodelled half my house & visited San Diego earlier in the year.

You have to be prepared for the worst. You have to have some big balls. You have to work your arse off. No amount of vision boards will get you through start-up phase, putting your head down, taking daily actions & taking risks will.

#6 Make Your Own Opportunities

From roof scene, to the obtaining of a rock hammer, to building trust with both prisoners, guards & the warden, Andy makes the most of every opportunity presented to him and rejects Red’s advice
“This is just a shitty pipe-dream. Mexico is way down there and you’re in here – and that’s the way it is”

Business Lesson 6: Nothing will land at your feet. It’s your hard-work that creates opportunities. It’s your ability to sort the gold from the manure that will help you action the right opportunities. You will make mistakes. You will waste time. You will feel like it would have been easier to set fire to a pile of bank notes. But with the right plan, attitude, connections, product & actions, it will come good.

Be realistic about what you really want to achieve & what that really takes. Step-away from the bullshit promises of the gurus. They are living it large on the money of lazy people who want to get rich quick. Don’t be a sucker. There is one born every minute, don’t let that be you.
If you want to achieve a millionaire lifestyle, work as they work for years. Take the risks they take, for years.
If you want to live a comfortable lifestyle, work hard for the first few years & get systems in place so you can have work-life balance further down the road.

Be truthful about who you are what you really want & the price you are willing to pay to get to it.

Oh and have some f**king fun on the way too. Life is not constant grind. It’s okay to get drunk once in a while. It’s ok to watch box set TV series once in a while. Plan it, do it, move on.

#7 Be a Quiet Rebel

Not only does Andy not listen to Red’s advice but he also challenges authority & the status quo. We see him locking a guard in the toilet so he can play opera over the tannoy for all the inmates to enjoy, an act of rebellion that gets him a few weeks in solitary confinement.

“those voices soared higher and further than anybody in a gray place dares to dream. It was like some beautiful bird flapped into a drab little cage and made those walls dissolve away, and for the briefest of moments, every last man in Shawshank, felt free”

He fights from the inside. He uses his expert status to change others’ lives. He knows how to quietly get his own way.

“I don’t run the scams Red, I just process the profits. Fine line, maybe, but I also built that library and used it to help a dozen guys get their high school diploma. Why do you think the warden lets me do all that?”

Business Lesson 7: Too many entrepreneurs think they are alpha wolves when they are actually sheep following the gurus to the letter. Now it’s hard to be a rebel if that’s not your natural personality. And although no-one seems to say it much, it’s ok to be a sheep. You can be vanilla & can do very well if you at least think for yourself rather than blindly follow others.

Not all businesses need tribes & leaders. Be honest with who you really are before you fall off the cliff lemming-style.

Do you really have leadership traits that are useful in business or are you best suited to a business that needs no tribe?

Two years ago I would have said I had no leadership or tribe building skills and I would have genuinely meant it.

I am the accidental leader.

The educated rebel who got so pissed-off with the guru-cons, I decided to take-on the snake-oil salesmen because friends of mine were being financially ruined buying into their bullshit.

Looking back it’s not a surprise, my tribe, I have always been a black-sheep, the underdog supporter, the person who cares in a pragmatic & practical way. I am an alpha-female without realising it, I am the rebel, I am a leader … but I never sought it out, or even thought I was. However the traits were there, I didn’t get crippled by inactivity & procrastination when under threat or at financial risk, I took action. Maybe the only skill you initially need is to take action.

Notice I say initially as that brings me nicely to point 8.

#8 Persistence Pays

As a geologist Andy understands about two forces, pressure & time. We learn of his tenacity when seeking extra funds for the library.

“Son, six wardens have been though here in my tenure, and I’ve earned one immutable, universal truth: Not one of them born whose arsehole wouldn’t pucker up tighter than a snare drum when you ask them for funds”

Andy takes on-board Brookes’ experience, by-passes the warden and writes directly to the Senate. He writes a letter a week. After 6 years they release $200 & some second-hand books. But instead of being satisfied with the first pay-out, Andy’s attitude is to double his efforts – imagine what we could get if I send two letters a week.

The action pays off. Andy secures a fund of $500 a year which builds the best prison library in New England.

Therefore should the viewer be surprised that Andy spends 19 years digging an escape tunnel with a tiny rock hammer. He should be called Mr Persistent Dufresne.

Business Lesson 8: You will go through tough times. These can last for months. Do you have the endurance & stubborn determination to keep going?

I am not very good at mind-set stuff. I am good at taking daily action. Action that means something, not the piddling little stuff many entrepreneurs get caught-up in.

However I am very good at calling it as I see it. I could be wrong of course, but I will tell you my opinion.

I have told one client they are not cut out for business & should go back to their former life in the City. They just don’t have the resilience & emotional detachment to run a business. Well they didn’t at the time I mentored them, maybe they’ve developed it. If they haven’t, it doesn’t matter how much money they make, they will always be emotionally crippled by their business <<< and that is no life.
So there it is #8 isn’t just persistence, its persistence, resilience & emotional detachment from the outcome.

#9 Make Good Use of Your Time

It would be very easy for a double-lifer to give-up on entering Shawshank. But Andy makes 100% full use of his time, not only in helping other inmates, carving a chess set, setting up a library, cooking the books for the warden, doing tax returns for the guards, but also spending every night for 19 years digging his way out of hell. The reward, freedom, is substantial but a long-way off however sitting on his arse, doesn’t get the tunnel dug.

Business Lesson 9: How many entrepreneurs really work for their desired results with consistency over long-periods of time? I meet & talk to a lot of entrepreneurs well into the hundreds every year.

By far the majority, 95% as a guestimate, procrastinate, live in fear, don’t take risks, get side-tracked doing menial stuff, avoid the real work, outsource at minimal levels and look for the cheap-arsed solution every time. Yet they want to attract high-paying 1-2-1 clients who make instant decisions, stay on-course, work really hard to achieve.

I think you see the problem with that. I will say this again you attract what you are.

If you aren’t willing to do the work, when you have coaching clients why do you think they will?

The most successful entrepreneurs I meet work damn hard on the important stuff & outsource the menial tasks to move projects along quickly.

#10 Take Daily Action

All of Andy’s plans & connections would have come to nothing if he had not seen his ideas through by taking action culminating in him crawling
“through a river of shit and come out clean on the other side”

And out the other side to freedom, riches & a laid-back lifestyle in the sun but it didn’t happen overnight nor on a 4 hour week nor with a get out of jail quick scheme.

Business Lesson 10: the 4 hour week is a lovely theory. It may just work if you are happy to live in a cheap-arsed country like the Philippines. It takes very little money to live like royalty out there. And that was actually the premise of the book. It’s just you that have misinterpreted to suit your own daydreams. If you want to live in the First World to a Royal standard, that takes considerable money. To have considerable money you have to work hard to a plan.

That plan will have objectives, strategies & tactics. Tactics are actions. The daily grind. The things you have to do to get to your ultimate objective <<< which will change by the way.

If you are ambitious, have clear focus, you will be writing 12-week plans & be a force of nature in getting it done.

Bad days may exist but you still take daily actions. I like numbers, actually that’s not true I hate numbers, I failed maths with an unclassified grade, but I like numbers because they answer the question did we get there? Without a number whether its sales, awareness, shares etc…we cannot answer the question with certainty.

Paul Mort taught me another number on Mindset X. He said write down & take 5 daily actions every day. I like this. Every day you can see you have taken 5 daily actions as you tick them off the list. So I have adopted this.

By the way, I mean money making actions, not routine tasks. Think on this When you take 5 daily actions this means – In 12 weeks you’ll have taken 420.

In a year this is 1825. Whose business would not grow if they took 1825 significant actions in a year?

When you are on an entrepreneurial journey you will experience many emotions from fear to excitement to stress to depression to elation – repeatedly. Just like prison life, entrepreneurialism, to be successful, has to consist “routine, and then more routine”

This life has amazing highs and lows. The biggest mistake I see people making is to treat their business like a hobby. To fail to have routine, systems and strategy.

You are at “the start of a long journey whose conclusion is uncertain” but if you have a plan, have good strategies & take daily actions, you will ‘control’ the outcome.

You are not likely to be blown over by a stiff wind as long as you have some, or preferably all, of the qualities displayed by Mr Andy Dufresne, the coolest inmate around.

NEXT – this bit is IMPORTANT I work with bad-arse entrepreneurs, those who get it & want a qualified marketer in their corner.

The black-sheep that are cool, work hard, understand the importance of strategic plans & daily actions. I take no prisoners & accept no bullshit. If you want to talk about whether we are a good-fit, email me on>>> karennadkarniruffle@gmail.com

Be warned, if I think I can significantly add monies to your business, what you do interests me and I like you, you will be working f**king hard for 90 days.
If you are lazy, think of your business as a hobby, do not put business first, don’t email me – you will be wasting my time & yours.
Cool rebels >>> karennadkarniruffle@gmail.com

2 Comments on “Entrepreneurial Lessons from the Coolest Man in Prison”

  1. Wonderfully written piece referencing my favourite film.

    I think a lot of people have the dream of coming out smelling sweet on the other side, but few are either prepared or willing to crawl through the fecal material to get there.

    I’ve said it before and I remind myself constantly – the road to easy Street goes through the sewer……but there is plenty of light in the dark tines if you look for it.

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