Risky Bidniz

IMG_2258Monday, 2:26pm
Visalia, CA
He wants to dream like a young man, with the wisdom of an old man. He wants his home and security. He wants to live like a sailor at sea.” (Bob Seger, “Beautiful Loser”) 


We’re in for a treat today.

One of the best storytellers in copywriting — my longtime cohort Jimbo Curley — has sent us a riveting tale sure to send shivers up the spine of every entrepreneur alive…

… while simultaneously delivering one of the most primo lessons in getting after your own success. I laughed out loud several times — Jimmy has a real talent for doing that to readers.

Enjoy… and reap the profits of learning the lesson. Here’s Jimbo:

Thanks for the intro John.

Something crossed my mind the other day — just after I ran over my neighbor’s dog.

Here’s what I was thinking: As an entrepreneur, a business manager, or just a plain working stiff, you may not be taking enough risks.

Or perhaps not the right kind of risks.

I’ll tell you about poor Rex in a second. For now, fasten your seatbelt. You’re in for a wild ride.

“Risk” is the base ingredient for success. It’s the secret sauce to landing a spouse who’s outta your league. The mechanism for pole vaulting over your competitors. It’s how you’ll win big, and make your nay-saying friends and family look like idiots for ever having doubted you.

I’m serious. Today I own and operate a couple companies that earn in the millions each year…

… but twenty-something years ago it wasn’t like that. Back in the early 90s I was managing a near half-million dollar marketing budget for a hardware and contracting operation – at $28K a year. I figured I had a secure job, a good title, and would safely “ride my way up” the escalator of success while others risked their necks climbing up the rickety ladder.


I opened my eyes. The media reps who landed me as a client were wearing silk ties and gold watches. The guy running the crumby print shop I frequented was driving a new Beemer. The owners who employed me were living in obscene homes and enjoying three or four lavish vacations a year.

And yet there I sat for 8 to 12 hours a day at a particle-board desk. I ate a bag lunch and drove a 10-year old beater.

I wanted new stuff. I wanted lavish. I wanted obscene.

It began to sink in.

Achieving such noble and lofty goals in total safety was a delusion.

Simple math and ruthless honesty made it clear — I could NEVER get there “working my way up” from $28K a year.

In the “death zone” of Mount Everest climbers must use ropes and ladders to traverse a sheer 40-foot rock-face before they can reach the peak. It’s called the Hillary Step. (It has nothing to do with Clinton, but Sir Edmund Hillary, the first nut-job ever to summit Everest and come back alive.)

One screw-up on the Hillary Step… one minor bobble… and you’re dead meat. 

Yes, you CAN refuse that terrifying climb up the Hillary Step, but it means forfeiting your shot at basking on top the world with your pals, (who you’d promptly leave for dead if anything went wrong).

No risk, no reward. Simple.

You want to get your kid into private school and a decent college? You want that cozy beach house where your family can enjoy memorable summers? You want to travel the world and see the pyramids? You want to make sure your parents are comfortable and well-cared for in their old age?

These wants require resources – sometimes known as “money”. Lots of it.

And without skills… a realistic game-plan… and some risk-taking to acquire said money, your insatiable “wants” amount to, (sadly), only impossible fantasies.

Like some teenage dream of playing lead-guitar in a world-famous rock band. Speaking of which: About six months ago I met Martin Pugh, a very English dude, at a local dinner party.

Ever hear of Martin? Neither had I. But it turned out to be a mind-blowing chance encounter. During our polite conversation, Martin happen to mention that in the 60s and 70s he played lead guitar in the rock bands Steamhammer and Armageddon.

Hmmm… wait a second… I HAD heard of them. The chat continued… and the plot thickened. Among his friends – guys he knew and had played with regularly — were members of the Rolling Stones, Led Zepplin and The Yardbirds.

What? In case you’re missing it, his “mates” included such guitar gods as Jimmy Page, Ron Wood, and Eric Clapton. Martin once even jammed with, live and onstage, the legend himself… (wait for it)… Jimi freakin’ Hendrix. 

So don’t get me wrong. I am a big believer that — with ability and a willingness to “put yourself out there” — anything is possible.  Sky’s the limit. Dreams happen.

Anyway, back to my rookie days.

It eventually sunk through my thick skull that a river of cash would not flow its way to my doorstep just because I really wanted it to. I had no rich uncles near death. No wealthy friends willing to support me. I didn’t live near a casino or even know how to play craps.

So I had to figure something out. The clock was ticking and none of us has forever.

As you can guess, entrepreneurship was the only vehicle readily available that could possibly transport me to the kind of life I wanted for myself and my family. It’s the same for you. Because any job that has you “working for the man” means you’re actually riding piggy-back on risk takers.

The more you feel like dead-weight to them, the worse off it is for you. How “secure” is that?

I mean, who’s really the bigger risk-taker here? In my $28K marketing director position I had many, many successes — but I could not easily account for them.

Yes, I worked hard producing TV, radio, newspaper, magazine, direct mail, and sales support materials — but it wasn’t direct marketing, (a skill I learned later on, from Carlton, in a series of the greatest “eureka” moments of my life.) In other words, I couldn’t prove how much money I had actually earned the company. This meant that even at a paltry $28K salary, I was still a liability to my employer because my salary was on the WRONG side of the accounting ledger.

I was in the “expense” column. Any downward trend in the business and the owners could simply scan down the expense report with a red Sharpie and ask: “Hmmm, do we really need this guy?”

That’s not security.

And if you hold a private-sector job where you’re unable to definitively prove, with real numbers, that you’re worth more than your salary, then you too are secretly on that list.

Now, Bud was another story.  He was the hot-shot outside sales person. He was earning three times my salary. He was at home having fun in his new pool with his harem of whores while I was working late.

The owners loved Bud. His skills landed them whale-sized clients that brought in hundreds of thousands of dollars week.

The bastard would never have a red Sharpie hovering over his name because firing him would be like burning money. Bud was on the right side of the accounting ledger — in the “major fat asset” column. (For the record, Bud and I were actually good friends. I learned a ton about bare-knuckles salesmanship from him.)

So yes, I’m encouraging you to take a hard look at who’s putting-up the money to pay your salary – with an honest evaluation of how they may view your “worth” on an accounting ledger.

Think about becoming an entrepreneur. If you’re already there, consider pushing your skills and risk-taking abilities to the next level.

But before you do, let’s dig a little deeper. Because not all risk-taking is created equal. So I’ve broken it down for you.

Here we go.

Risk Taking #1: The treacherous go-for-broke “Banzai” charge. 

And here’s where I tell you the sad tale of Rex the wonder dog and how my neighbor Lou – Rex’s owner – came to start calling my car “The Death Machine”.

Rex loves to chase cars. Rex loves to chase MY car. Problem is, Rex hasn’t a clue of what to do if he caught my car. It’s the thrill of the chase. Makes him “feel alive”.

If Rex had thumbs, he’d climb Everest and dance the Macarena on the Hillary Step.

So last month I’m driving to the market when Rex, being Rex, galloped full throttle across his yard and performed a perfectly executed vault – launching his muscular 80-pound bulk through space and time like a gymnast soaring off the parallel bars.

Slow motion. So gorgeous. Until of course he hit my front tire. Rex’s behavior is what I call Banzai Risk Taking… … which includes such activities as Russian roulette, sharing needles with homeless strangers, and betting your house on a business “premonition” with little or no hard evidence that it will ever pay off.

Been there, done that. I used to race around on motorcycles without a helmet… fly an ultra-light (basically a flimsy kite with an engine)… and, in my very first entrepreneurial venture, risked my house on a “hunch”. I had cleared-out my entire savings account and maxed out a $41,000 line of credit to finance a “custom motorcycle painting” instructional package.

I paid – upfront — for expensive 2-page long copy magazine ads in three major publications. When my worried wife expressed concern, I assured her in the strongest possible terms that I knew exactly what I was doing.

I didn’t. And when the money was distributed and gone the full realization of what I had done hit me. I could lose my damn house. I shivered at the thought of explaining that little mishap as we packed our bags.

Then it happened. The magazine ads hit. On that day $12,300 shot through my merchant account and plopped into my bank account.

And it just kept coming.

By week’s end, I paid off the loan.

By month’s end, I purchased a new car and had a damn good start on a savings account that would eventually pay for the design and building of a new home.

I took a deep cleansing breath. I was on my way, at last.

But the approach I took on that initial project was the stuff of compulsive gamblers and adrenaline junkies. Perhaps similar to Rex’s desire to “feel alive”.

John Lennon was once asked: “What is life?” 

His answer: “Life is what’s going on while you’re thinking about something else.”

You wanna snap out of the daydream? You wanna experience the full brunt of life in the here and now?

No problem. Just lose your footing on the Hillary Step. Fly an ultra-light at tree-top level in high winds. Or risk everything you own in the world on an unproven business hunch.

That’ll wake you up… and fast. 

Sure, the rewards can be extravagant. But it is, (in the words of Lynyrd Skynyrd): “One hell of a price for you to get your kicks, hell yeah”.

In retrospect, there were smarter ways I could have approached this.

Today, following two high-speed motorcycle crashes, I don’t ride cycles anymore.

After a few near-misses with trees and high-voltage electrical wires, I don’t fly ultra-lights either.

And I have no brilliant plans to climb into the death-zone of Everest.

Oh yeah… and I no longer risk every penny I’ve got on unproven “hunches”.

Risk Taking #2: The ticklish “thin-ice” silly chance: This reminds me of the time Carlton and I were in a Reno casino. The scene played out something like this: “Hey, John, teach me how to play craps.”

“Okay. How much you got in chips right now?”

“Two hundred.”

“Good. There’s no hand in action. Place a hundred on the pass line for the come-out.”


He rolled his eyes and pointed. “Put your chips there.”

I plopped down a hundred on the pass line and, as the dice rolled and the fast-talking stickman shouted gibberish, Carlton expertly guided my odds bets, having me disperse the other hundred in additional wagers behind the pass line. It was an exciting blur of raucous activity…

… until quite suddenly the chips were scooped up and gone. John threw up his hands, “Well, that’s it”.

“That’s what?”

“That’s it. You lost your money. Fun, huh?” We looked at each other… and burst out laughing.

Look, nobody likes losing money. But for a couple hundred bucks I learned a thing or two about craps with one hell of story to boot.

Now if that money would have represented a huge percentage of my net worth or was the only cash I had on hand for Tiny Tim’s lifesaving operation, then it would have fallen under the category of Bonzai Risk taking.

Okay… so what does this have to with entrepreneurship?

A lot. Because in direct marketing walking out on thin ice is absolutely necessary. Risking some time and money is the only way you’ll know for certain where your hardcore buyers hang out and which sales pitch will work best.

Think of it like hunting for gold. No sane miner decides to “go for it” and throw all his manpower, equipment and resources into a piece of ground until he’s completely confident that it will produce hefty profits. So he risks a much smaller amount, sinking strategically placed test holes.

If the holes don’t produce, the miner has gained valuable insight at relatively low cost while moving on to new ground.

On the other hand, if the test drilling coughs-up magnetic black sand and gold flakes… well, the gloves come off and it’s time to take things to the next level.

Risk Taking #3: The educated roll-out: This is the next level. The stuff of savvy entrepreneurs.

Once you’ve got a proven offer that converts and a damn good idea of exactly where your demographic congregates… it’s time to open the flood gates.

I mean, if someone said he’d pay you two dollars for every dollar you handed him – how much money would give him? The short answer: Every penny you could manage. 

But play it smart. Start by giving him a dollar. He gives you back two. You now give him two dollars. And so on. It builds fast.

Same with purchasing traffic for a high-converting campaign. You can start small and roll the winnings back into the next round, (and skim a little something to wet your beak).

Of course this isn’t risk free. Nothing is.

But today there’s a little something called the “internet” to make testing fast and relatively cheap. There’s mountains of traffic too — and MOST of it has nothing to do with Google. Once upon a time direct marketing involved testing ads and demographics inside expensive magazines and through rented direct mail lists. It meant placing a lot of money on the line for an extended period – up to a month or two at a time – before you could even determine results.

And here’s where we flash back to my early days as an entrepreneur.  I had already worked with Carlton for almost 5 years when I decide to create an instructional product for hunters. It was well researched, well produced, and testing showed the pitch had serious promise.

So I rolled it out to a larger audience with an initial media buy of $20K, then rubbed my hands together and waited for my shopping cart and call center to explode.

Tick. Tick. Tick… tock.

I’m still waiting.

It was not to be. Despite having all my ducks in a row, the quest failed. I lost my time and a lot of the money I had invested.

And yet… here I am. Still alive.  Not only alive, but thriving.

My point is that, unlike plunging off the Hillary Step, failing during a roll-out rarely involves bouncing off rocks like a ragdoll for thousands of feet until your battered frozen body is wedged for eternity inside some lonely glacial crevasse.

No. It certainly feels like that for a while, but it’s different.

It stings, but you survive – a little wiser – and get up… tweak your campaign (or turn to an entirely different product)… and try it again. And again. And again, until you get better. Until you get it right.

The key is to learn the craft and tolerate some risk. The trick is to nail down exactly WHO is purchasing your product (i.e. women, 35 to 45, with children and dry skin), split test your campaign until it’s as good as you can get it.

Then split test some more until it becomes smokin’. As your profits increase, roll it out with bigger media buys directed at prospects precisely matching those who responded to your test offer.

Then continue to take “silly risks” on promising but untested traffic sources that have similar demographics.

It eventually becomes like a steamroller to your competitors.

And it just keeps going… and growing.

But at the core of it all is a sales funnelthat converts. Without that, forget it. You have nothing.

So the question is: How do you build a sales funnel that converts?

Well, again you must learn the craft. Study guys like Claude Hopkins, Dale Carnegie, Napoleon Hill and Robert Cialdini. Check out Carlton’s “Kick Ass Copywriting Secrets”… his “Simple Writing System”… the Marketing Rebel resources… or his latest Kindle book “The Entrepreneur’s Guide To Getting Your Shit Together”. This kind of coaching is critical because knowing what makes your prospect tick is at the very heart of selling.

It’s not about understanding technology… but rather understanding people.

How you handle the risk-taking is (of course) up to you. But the resources you’ll need to build and hone your direct marketing skills are right at your fingertips.

There is no need to “go it alone”. That’s just plain foolish. And I assure you, you won’t “figure it out” without help.

I get nothing for telling you this. No kickbacks. This is just my advice to you. Take it for what it’s worth.

Because for me personally, without John’s mentoring, it’s likely I would still be sitting at a particle-board desk, dreaming of greater things without ever possessing the necessary skills to achieve them. Working with Carlton has been my chance to jam, live and onstage, with the legend himself. Word.

And Rex?

Well, I saw him just the other day. He was sitting in his yard with a goofy plastic “healing funnel” wrapped around his head. Lou had chained him down for his own protection, but as I drove by, Rex tugged and whined… … pleading for just one more shot at being smashed under the wheels of The Death Machine.

Some dogs never learn.

Thanks for letting me share this tale.

Jimmy Curley

P.S. Love to hear your take on this subject, down in the comments.

How has risk played a part (either as hero, villan or bystander) in your career so far?


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  • Jeremey says:

    Love it, Jim. I pop over to your blog every now and then to see if you’ve made any updates since 2011 🙂

    This hits home with me – I got a great job in sales right out of college…salaried, but with a company car and expense account. Between the ages of 24-30 I sat back and spent as much money as I could on food, booze, guitars, and shoes.

    Around the age of 30 or so, I started to notice at all our regional meetings that most all of my colleagues were in their mid-50s to early 60s, MUCH better at my job than I … and making the same amount of money as me.

    That’s when I realized I’d peaked. There would never be anything better than what I had RIGHT THEN. And I thought, Jesus, if you ever find me at the age of 55 sitting in a regional sales meeting next to a 30 year old making my salary and listening to a 35 year old VP making twice my salary, strike me fuckin’ dead of an aneurism right there.

    So from that point forward I’ve taken lots of risk…it hasn’t always paid off but it’s gotten me a lot further than where I’d be if I was still hauling donuts and pizzas around for a living.

    Great read & thanks for the share JC!

    • Jimbo says:


      You busted me man.

      I’ve been a slacker on my own blog for a long time and seem to be better at being a “guest” blogger.

      Glad you enjoyed this. There’s that moment of clarity when you look around at all the grey entrenched souls and that little voice in your head cries, “get out now. Get out while you can.”

  • Kevin Rogers says:

    Raucous tale, Jimbo. Priceless lessons and full mastery of your instrument. What a treat to read.

    My favorite word in all this was the perfectly placed “rarely” in this paragraph:

    My point is that, unlike plunging off the Hillary Step, failing during a roll-out rarely involves bouncing off rocks like a ragdoll for thousands of feet until your battered frozen body is wedged for eternity inside some lonely glacial crevasse.


    Thanks for the ride, my brother. And please post more.


    • Jimbo says:


      Always a pleasure my man. This was a fun one to write. Looking forward to your next guest appearance as well.

      Thanks for the kind words brother.


  • Sharon A says:

    Good Morning, Jim! Thanks for an awesome post.

    My first, and biggest, go-for-broke risk was becoming homeless. Deliberately. I moved into my car to escape a life-threatening situation and I never looked back. People said I was mentally ill, but it was actually the sanest decision I ever made. I’ve never regretted it.

    I spent seven years out there, honing my survival skills. I was assaulted a few times; I had the car shot full of bullet holes when I was sleeping in it; and I had to put up with law enforcement asking for “favors” in the middle of the night. That was my “rental fee” for being allowed to live in my car.

    I walked five miles every day picking up bottles and cans so I could eat. I also put myself through four years of college, got into therapy, and learned I could think for myself without getting hospitalized. I refused to leave the streets until I’d saved enough money to support myself. It took me seven years to get my first apartment. Then I had to learn how to live like a civilized person, lol. The mindset is totally different.

    I ran a laundromat for ten years. In that time, I tripled the client base for the owner by setting up a lending library, a coupon exchange, a kids’ corner, and a coffee station in the laundromat. I also put in flowerbeds all around the building, so the customers would have places to relax and read while their laundry was going. We went from being an ordinary laundromat to being called the best laundromat in the northwest corner of the state. People came in from eight different towns for laundry service.

    But I left. After ten years, I was making $9.50 an hour. The siblings that owned the laundromat (both millionaires) were fighting, and I was being paid by one while being bossed by the other. My proposed business plan for expanding the client base even further was used for scrap paper. The corker? When I asked for a raise, I was told that the job wasn’t worth paying me any more because it wasn’t a very hard job, and it didn’t take a lot of brains to do it. I gave my two weeks’ notice then and there, and I walked away from all of it. It broke my heart but I had no other choice.

    As an aside, my old boss tried selling the laundromat two years ago because the client base was almost ZERO. No one wanted to buy it. I was tempted, but buying a business to prove you can run it is never the right reason to buy it. I heard recently it may close soon. His loss!

    I started my own landscaping business on a shoestring the day after I left. I threw all my tools into the back seat of my Geo Prizm and began doing volunteer gardening projects as a way to advertise. I didn’t have a budget, so my work was my advertising. It was a hair-raising, exciting time, and I loved every minute. Within two years I had 32 clients, all word-of-mouth. The only time I had any turnover was during the recession of 2008.

    Now (five years later) I’ve closed the business, because I shattered my leg and ankle in a freak accident last year. I broke five bones, needed reconstructive surgery (including bone grafts) to repair all the damage, and I didn’t walk for five months. My foot is partly paralyzed now due to nerve damage, and that may be permanent. Despite not losing a single client last year, I still had to close the business. I can’t ask them to wait another year while I continue to heal.

    I don’t know yet what my next risk will look like. But if I want to get us out of the hole we’re currently in, it will have to be a biggie! 🙂

  • Jimbo says:

    Hey Sharon — glad you made it.

    This is hair-raising, and I’m glad you’re still around to tell the tale. Amazing what people are capable of enduring.

    Once upon a time, when I was a 19-year-old starving college student, I lived in my truck for a week while job hunting. Looking back, the thing that bothered me most was that damn automatic transmission shifter sticking me in the side.

    Remember the words of John Quincy Adams: “Patience and perseverance have a magical effect before which difficulties disappear and obstacles vanish”.

    Thanks for dropping a note Sharon.

  • Great post, Jim.

    Makes me want to fly out to Vegas and play some blackjack.


    • Jimbo says:

      David… I’ve got a “system” for you. It really, really works. Problem is, if you get caught, you get your legs broke.

  • Jae Markham says:

    Excellent Article Jim…Great Insight that many of us have felt as the working stiff for someone elses pocketbook!

    • Jimbo says:

      I’ve was a working stiff since 4th grade, when I asked my dad for an allowance.

      He looked at me curiously… left… came back with some paperwork and handed it to me. He had bought me a paper route.

      “You got a job now. You never have to ask me for money again.”

      Cool thing was, I was the only 4th grader walking regularly around with 20 bucks in my pocket.

      Thanks for writing Jae.

  • Kevin Dawson says:

    Risk? I take on risk every time I put pen to paper. And any copywriter who doesn’t take it serious enough to think they’re risking their reputation, their abilities, and their client’s cash every time they write…

    …isn’t worth the ink to blot out their pathetic existence.

    Yeah, I’ve won big. Lost big, too, although losses get considerably less with experience. I can’t tell you how many times I’ve quit this business. Gotten down and disgusted with crawling face-down through the mud of marketers, clients, and yeah – my own bullshit.

    Failure is a tough teacher. It makes you reach down inside and see if you’ve got real guts – or just a hollow space filled with empty delusions of who you tried to pass off as the real you.

    But you’re right. Failure isn’t permanent unless you don’t pick yourself up from that last crevice you mentioned.

    Hell, maybe I just forgot how to quit. Or maybe it’s that Irish Alzheimer’s… we forget everything but our grudges.

    And like you said, there are others to help. I’ve appreciated your help in the past. Real eye openers. There are are others in our circle I’ve reached out to, and they’ve been there for me too.

    Thanks, Brother. Nice to see you posting up again. And giving me pause for thought.

    • Jimbo says:


      Funny. Got a lot of that Irish blood coursing through my own veins too.

      You’re absolutely right about taking risks in your writing. You always take the chance of a client or a buddy or a family member reading over your work and asking “What the F__ is THIS supposed to mean?”

      Scary stuff.

      Glad you popped in. Appreciate the comment.

    • Jimbo says:


      Sales copy is a LOT of risky decision making.

      Do you dare say this? How strongly do you make the point? Do you risk insulting people (of course you do)?

      Humor is also especially risky writing. People can take things the wrong way rather quickly. Or feel like you’re making fun of them.

      But, like you suggested, you gotta push the envelope… always.

      Good comment. Thanks Kevin.

  • Scott Rewick says:

    Such a great read! So much wisdom in so few words. Your words made me think of this…

    How in the hell could a man enjoy being awaked at 6:30 am by an alarm clock, leap out of bed, dress, force feed, shit, piss, brush teeth and hair and fight traffic to get a place where essentially you made lots of money for someone else and were asked to be grateful for the opportunity to do so?

    Charles Bukowski, Factotum 1975

    • Jimbo says:

      Scott. Well said.

      I just want to add that your media buying course helped me understand a lot of the ins and out of taking chances with traffic purchases.

      Thanks that… and for stopping by.


  • Jane Pimentel says:

    OMG – I’m sitting in a regional sales meeting w/ 30 year olds around me. And I”m not close to 30 anymore. Hmmm.

  • Mark L says:

    Hey Jimbo,
    Great post and a riveting read!
    I do remember when you put out your first products.
    I was running camera when you made them, I believe.

    Yes, you’ve taken risks…but along the way you’ve turned into a world-class marketer and copywriter.

    Always a pleasure to absorb your wisdom!

    Mark E Mark

    • Jimbo says:

      Mark E Mark.

      You not only ran the camera — YOU found the talent for me. Folks, it was a guy by the name of Bob Kovacs. Bob had worked for George Barris and painted the original Batmobile from the 60s TV series. The Green Hornet too.

      He had also painted a lot of bikes for the Hells Angels.

      Oh the memories…

  • Robert Gibson says:

    Great post Jimmy!
    Reminded me of my favorite Churchill quote:
    “Play the game for more than you can afford to lose…only then will you learn the game.”
    Take Care,
    Robert Gibson

    • Jimbo says:

      Love Churchill.

      I read something about his visit to the White House. Apparently Winston liked to stay up all night shooting the shit, smoking stogies, and drinking copious amounts of booze.

      That visit damned near killed Roosevelt.

  • Stan Dahl says:

    Nice post, Jim.

    Risk – not understanding it, irrationally managing it, and being terrified of it – is, IMO, tops on the list of reasons the vast majority of our fellow humans should not be entrepreneurs.

    It’s just not for everyone.

    • Jimbo says:


      It definitely isn’t for everyone.

      Some feel much more balanced simply working 9 to 5 for someone else — but that’s not necessarily any more secure.

      It’s kinda like Helen Keller once said: “Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing.”

      And when it comes to entrepreneurship there’s a misconception out there that “you’re either born with it, or you’re not”.

      That’s really not true. I’ve discovered is that a person CAN learn to manage it. Forget panicking. Forget the “all-in or nothing” thinking.

      As you suggested, it’s about rationally dealing with risk. It can be as uncomfortable as hell, especially at first. But if one can get over the initial “scardie-pants” phase and learn to maneuver using rational thought instead of raw emotion, you’ll be alright.

      Thanks for commenting Stan. Good stuff.

  • preston says:

    good stuff. i’m ripping off the email that got me here


    • Kevin Dawson says:

      Hey Preston,

      Good to see you posting up. I’ve studied Jim’s stuff too. His genius has left its mark.

      And you’re no slouch – you’ve got tons of personality in your writing as well. I can’t count how many young bucks I’ve seen online ripping it off.

    • Jimbo says:

      Preston… you are the email master. Been following your stuff for a long time.

      Thanks for checking this out.

  • Jimmy, sonce again, you show how talented you are…You got me to actually read something! True talent here folks. You won’t find a nicer guy either, but one that still has ruthless sales chops where it counts.

    I love taking chances….what’s the worst someone can say? No?

    What’s the other word people usually forget when it comes to taking a chance or dealing with someone else on the end of a sale?

    Yes. I believe people want to say yes. If you ask enough, you get to the be the person they said it to.

    • Jimbo says:

      Lawton my man.

      Good to hear from you. Was just talking to Carlton about your mad Kindle-book skills.

      You’re right about that. Like the old cliche, Better to ask forgiveness than permission.

      Although I tried that once by putting the words “Hell’s Angels” in the headline of an ad.

      Should’ve asked for permission first.


  • Doberman Dan says:

    What a fun and instructional read, Jimmy.

    I’ve done the gambling approach with several of my business projects. One time I ended up homeless living in my car.

    The other time my income shot up so much higher than my broke white trash Barberton, Ohio comfort zone I started reeling it back in as fast as possible. I would NOT do that these days knowing what I know now.

    Keep this stuff coming please. I need to hear it regularly.

    All the best,
    Doberman Dan

  • Jimbo says:

    Doberman Dan!

    You’re describing here something that inspired the idea for this blog in the first place. Namely that risk taking doesn’t have to mean the same thing as “gonzo”.

    Like we’ve both learned (the hard way), you gotta make educated bets.

    I didn’t do it that way at first, but thankfully it happened to work out in my favor. I suspect that’s pretty rare.

    As you know, it’s a methodical process. Build the sales piece, split test it to targeted traffic with small amounts of money until it proves profitable then use the profits to roll it out bigger.

    A less nerve-racking that way.

    Thanks for stopping by. Always good to hear from you.

  • Rob Gramer says:

    Thanks for the blunt truth.

    On the train back from a central america surf trip. I bet the farm on some monster waves in Nicaragua and it’s a hell of a lot more fun than watching from shore (even when you get smashed).

    It’s all risk or sitting on the sidelines. Thanks Jimbo.

    • Jimbo says:

      I saw these guys BASE jumping with a “winged” fight suits. Basically just some Dacron material between their arms and body.

      Allowed them to soar and hug the mountainside on the way down. Looked like fun — but of course one wayward gust of wind and it’s over… forever.

  • Bernie says:

    The older I get, I fully realize that self reliance is the key to survival…period. I’m 50+, been unemployed for longer than I want to say…to the point where nobody wants to hire me. Working for someone else is no longer an option. Oh, my college degree is, and always has been, a useless piece of paper.

    My bank account is far from being depleted. I have always saved for a rainy day. And there have been many. Today I am enrolling in an online training course for PPV marketing. Not cheap, but I have to do it. I am also learning copywriting. That should help me with offer creation.

    “Beautiful loser
    Never take it all
    ‘Cause it’s easier
    And faster when you fall.”

    Not for me…if I have any control over the situation.

    Great Post.

    • Jimbo says:

      I thought the Seger lyrics at the front were uniquely appropriate — a guy who wants it all without risk or effort or taking a stand. Classic.

      You on the other hand are taking the effort. Congrats on that.

      I’ve particularly found “PPC-Coach” to be helpful. It’s really geared toward the affiliate marketer — which is not how I make my money — but has lots to offer and isn’t much money.

      Stick with it. Fight the good fight. Skills and educated risk taking is where it’s at.

      Thanks for the comment Bernie.

  • […] Läs artikeln på Risky Bidniz | The RANT. […]

  • Timmy C says:

    Great post Jimbo. It was fun to read and I could dance to it. I give it 4 stars. I was seriously inspired to re-evaluate working for “the man”…..because you are correct, ‘no risk, no reward…simple.” Thanks for sharing. 🙂

    • Jimbo says:

      It’s easy to “boxed in” to a position. You’re managing to pay the bills, you’ve got a comfortable routine set up — but pretty soon your stagnating.

      For me, the worst of it was then sinking feeling that life was passing me by.

      In my own business, there’s now never a dull moment. That of course can be taxing — unless you learn the trick of “disengaging” from your biz (the subject of another blog).

      Thanks for writing Timmy.

  • John Lee says:

    I think your advice can be applied to any situation in life, not just business. Keep speaking up!!

  • Ken Ca|houn says:

    Great post, you had me riveted, on the slide, reading from start to finish. Good ‘closed loop’ w/Rex story. What you say makes sense, especially about different types of risk, and learning the craft. No guts, no glory. Play large or go home. Bring it.

    To taking intelligent risks,


    • Jimbo says:

      Yes. Of course there IS a weird no man’s land — a DMZ just between Bonzai and Educated risk taking. Entrepreneurs have to walk that thin line everyday.

      I mean, you’re not gonna risk everything you have on a hunch, but you make choices with limited information all the time and risk enough to make it sting pretty bad if things go wrong.

      You gotta push it… but not too far.

      Thanks for the kind words Ken.

  • Mark says:

    I know, I know… the voice of reason. But somehow it seems we’re hardwired to go “all in” and it takes gettin’ bitch-slapped a few times to see the wisdom of taking educated risks.

    You guys ever see a successful person that didn’t try to free climb the “Hillary Step” at least once?

    Very clever writing, Jimbo. Love the way you wove stories around the cluster of your main points.

    • Jimbo says:

      Hey Mark — yeah this was a blast to write. I craft a lot of sales letters but don’t get a lot of chances to just let loose and have some fun.

      Being methodical and disciplined is a tough thing in direct marketing for a lot of people. It’s like reading the directions before assembling a complex toy.

      The promise of big money is just on the horizon and there’s a real temptation just to sprint across the minefield.

      Bad idea. Better to read the directions, get well-prepared, and be willing to take SOME risks.

      This is what the survivors are doing.

      Thanks for writing Mark

  • Took me a while to read it all, Jimbo – but it was well worth my time. I truly enjoyed the story and the delicious way you told it.

    There is a downside though (it was a bit strenuous to the eye, with such a small font size) but luckily I have a huge screen, lol.

    Anyway, back on topic – life is full of risks all the time, but we don’t even remember taking many of them (think flying a plane, or even driving your car).
    The ones we remember, though…. make good stories, no matter the results for the risk-taker. The stories are still teaching a lesson, of sorts.

    I recently read a blog post from a traveler writer co-national of mine (no point in naming her here) about the life-transforming experience she had entering the cages of the tigers of Chiang Mai.

    I was thinking, while reading… even knowing that thousands of tourists have done it before me, would *I* do it too?
    To my shame, I decided I wouldn’t… like I wouldn’t do bungee-jumping or mountain climbing.

    Business-wise, however, I took many risks in my life. Some paid back a nice ROI, some almost threw me out in the streets.

    What gives?
    Am I a risk taker, or not?


    • Jimbo says:

      You officially sound like a risk-taker to me.

      When it comes to risk-taking though, it’s hard to hit that sweet spot — the zone hovering just between throwing up your hands and going for it and cautiousness.

      It’s annoying to do research. Studying tracking numbers and demographic stats is akin to grinding your teeth.

      But it allows a degree of certainty in your decision… an edge… that can’t be achieved any other way.

  • Rex says:

    Watch it bud! My name is Rex! And I don’t know much about chasing cars. But I DO know something about taking marketing risks the wrong way.

    I am trying to cut back! 🙂


    • Jimbo says:

      Just saw Rex again today.

      The stupid funnel is off his head and he’s officially off his chain and back on the prowl. I’m driving by his house a lot more carefully from now on.

  • Thanks for the reminder that risk is GOOD. Since we’re entrepreneurs our very existence is based on risk. It can be a lonely and self-doubting road sometimes. This post was a terrific reminder to feel the fear and do it anyway. Risk is a part of life on the edge.


    • Jimbo says:


      Yep. The flip side of “gonzo marketing” is “mother hen marketing”.

      I’ve seen this a lot. There’s a campaign that’s proven. It converts. It makes money. It’s doing everything you dream a sales funnel could do. But the roll out never happens.

      Or the roll-out is done in increments of $5 a month.

      I understand the need to be cautious, but there’s a time to let go of the reins and let your horses run free. Allow the campaign to do it’s thing and make you rich.

      Thanks for the comment Lo.

  • Mike Martel says:

    Excellent article and reminder that there are very few Hillary steps in normal life. We always fear the worse, but reality is most always not as bad as our imagination can make. I have been through several episodes that I thought looked pretty bleak at the time and each time I have come out better for them.

    I do like the story of Rex. I always respect people who just go full out for it!

    • Jimbo says:


      As a former Green Beret I imagine you’ve “gone for it” a time or two.

      Absolutely right though. Seems most times the fear is whacked out of all proportion from the actual potential negative consequences of the risk-taking.

      It’s a matter of conditioning though. The more educated risks you take, the easier it becomes and the fewer panic attacks you experience.

      The fear never goes away, (it shouldn’t). Just becomes more manageable. Thanks for the comment.


  • Dean Horine says:

    Great read Jim! For me risk is a great tool not only for making money, but for purging my brain of the half-baked theories, which I convince myself of from time to time (mostly out of laziness and complacency). Even I can’t honestly believe my own BS when the money is on the line. Nothing like a little butt-puckering risk to bring on the clarity!

    • Jimbo says:

      Perfect! You got it Dean.

      We all have our theories, but real direct marketers allow the hard numbers to guide them.

      Of course you gotta stick your neck out now and then with your best educated guess… but then track everything so that the next decision is no longer guesswork.

  • Nate says:

    Hey Jim
    Great stuff! Found my way here searching deep rabbit holes as I’ve found myself increasingly interested in a advertising.

    Not to expect advice but I do have a question I hope you might address. Of all your endeavours have you ever lost interest or passion in your current state to the point where you don’t want to work any harder and would rather cut it up and walk away? My situation: I own a custom bicycle design and fabrication company and it has turned from a passionate hobby into an up and down business. 6 years into the project and I am running on fumes, emotionally. I have found that I like telling the story of my brand more than making the products and this can be a bad thing as all my bicycles are “one-off” labor intensive custom bikes built with my hands only. I enjoy selling by product more than making it. I do everything in my business.

    Anyway. I look forward to more of your humorous and insightful writings. Can’t wait for another one!


    • Jimbo says:


      You’re describing something here that’s common to entrepreneurs.

      It’s typical for start-up entrepreneurs to adopt a kind of independent stubborn persistence — a one-man-band mindset that has you wearing a lot of different hats and doing a lot of different things.

      The thinking basically says, “I can do it all. I’m the only one who really knows how to do this and I’m the best at everything in the company”.

      But now that you’re a well-established business owner, this type of Rugged Individualism no longer serves you well. In fact, it’s probably one of the biggest reasons you’re frustrated, stalled, and feel like you’re spinning your wheels.

      The key is delegation. You should be constructing a team around you that you trust while you begin to disengage from the stuff in the business that you don’t like.

      I mean, if you enjoy selling, get or train someone to build the bikes. Again, that little voice tells you “but nobody can do it as well as me”.

      Ignore it.

      Get the best in the biz to build your bike while you sell. He may never be as good as you, but you’ll keep your business, you’ll enjoy your business, and your productivity will skyrocket.

      Hope that helps.

  • Mike says:

    This article was amazing.

    I just recently went through one of those “hunch” moments and lost my backside. Only my problem wasn’t the ability to sell the damn thing – it was the follow through on the other end – the risk associated with hiring others to do work for you.

    Thanks for sharing this!

    • Jimbo says:

      I’ve personally avoided products with a “long tail” fulfillment, (i.e. a fulfillment model that forces me to continually expend time and money long after the initial sale).

      It’s great when the initial cash comes in, but then you find yourself working your butt off long after the money is spent and gone.

      Glad you liked the article.

  • Jay C says:


    Couldn’t agree more with your sage wisdom here. There’s this pernicious stereotype of entrepreneurs as risk takers…when, in reality, the successful ones are really astute risk *managers.*

    For instance, I recently went full-time with my biz…but only after six straight months of growing revenues. And securing key partnerships. And having a deep network. And building cash reserves. And paying off debt.

    In other words, by the time I “made the leap”, there were lots of nice fluffy pillows underneath instead of a spike pit.

    That said, you can never completely eliminate risk. Nor should you. Sometimes you honestly need that me against the world, “cornered animal” mentality to shove the bullshit aside and take care of business.

    I’ll close with a searingly relevant quote from Y Combinator’s Paul Graham…

    “The number one thing not to do is other things. If you find yourself saying a sentence that ends with “but we’re going to keep working on the startup,” you are in big trouble. Bob’s going to grad school, but we’re going to keep working on the startup. We’re moving back to Minnesota, but we’re going to keep working on the startup. We’re taking on some consulting projects, but we’re going to keep working on the startup. You may as well just translate these to “we’re giving up on the startup, but we’re not willing to admit that to ourselves,” because that’s what it means most of the time. A startup is so hard that working on it can’t be preceded by “but.”

    In particular, don’t go to graduate school, and don’t start other projects. Distraction is fatal to startups. Going to (or back to) school is a huge predictor of death because in addition to the distraction it gives you something to say you’re doing. If you’re only doing a startup, then if the startup fails, you fail. If you’re in grad school and your startup fails, you can say later “Oh yeah, we had this startup on the side when I was in grad school, but it didn’t go anywhere.”

    You can’t use euphemisms like “didn’t go anywhere” for something that’s your only occupation. People won’t let you.”

    • Jimbo says:

      Jay. Love the quote.

      The thing about taking risk is that it’s really the only true filter that keeps the rookies and wannabes at bay. I mean, let’s imagine a business that rakes-in piles of moola without ANY risk on the owners part. He or she just shows up to cash the checks.

      Obviously that business doesn’t exist (except in over zealous sales copy) because if it did, there would be 6 billion people in that business.

      So risk is what makes possible that little cleared out section of ground from where you can build your business and earn your fat profits.

      Thanks Jay. Good stuff.

  • Dana H says:


    Can I call you Jimbo? I guess I just did… this is the internet and I can do anything I want.



    Great post though. Entertaining… inspiring… and motivating. I don’t know what it is, but I think risk to entrepreneur’s is like crack. You kinda get addicted to it, but learn to be careful.

    Note:(I’ve never smoked crack)

    But I have taken a lot of risk. And even though I still haven’t hit the jackpot I know it’s coming because I keep learning, and reading, and trying, and testing, and very few, if any, ever hit the jackpot on the first roll. Maybe not even the first 100 rolls of the dice. But when they do, mmmmm, how sweet it is.

    The only draw back, if there is any, is that the people are watching think most successful people just woke up, rolled the dice one day, and hit it big. And I think that’s why a lot of people give up early in the game. The don’t realize and/or aren’t willing to do the work, take the risks and put it the time it takes to make something happen.

    But back to the crack(risk). You can’t reach the high(success) without it. And a true entrepreneur, someone that’s driven to succeed on their own, won’t quit no matter how many times they fail. Marijuana won’t satisfy a crack addict, just like working 9-5 in a cubicle won’t satisfy an entrepreneur.

    This post really hit home because I’m in bounce back mode, coming out of rehab after closing a business after 6 years and helping my brother build his, only to realize that I have to get back to MY dreams and goals or I’ll NEVER be satisfied.

    Thanks again.


    P.S. I’ve seriously never smoked crack or even played a crack addict on t.v. Somehow that analogy just popped into my head.

  • Michael F says:

    The one thing I’ve noticed that sets me apart (and the rather considerable success I’ve had in a number of ventures) is that I’ve been willing to take massive action on something, often for weeks or months at a time, before I can hope to see a payoff. A lot of people see that as “too much risk.” And because they would never “risk” such effort without someone writing them a check each week along the way, they never do ANYthing. And so they never go ANYwhere.

    What’s funny is that they look at me as if I’m some kind of charmed individual. But really, all it is … is my willingness to say, “Nothing to it but to do it!” and jump in, guns blazing, and make it happen.

    I’ve been 100% commission in everything I’ve done for the past 12 years. There’s no guarantee on anything I do. But there’s also no ceiling to what I can accomplish.

    And because I’ve taken chances no one else around me would take, I’ve been able to earn more in a WEEK than many of them have ever earned in three solid years.

    But it all comes from my willingness to take “risks” in moving forward with GUSTO, no guarantees, no safety net. Just guts and excitement and a damn good work ethic.

  • Stevo says:

    Here it is! I’m here sitting in a **”cube”… if you know what I mean? Last week I wrote my first draft of copy ever. My roommate liked it, so now I think I have to re-write it lol All kidding aside though, now I just want to learn how to implement it. I know this certain market but I don’t want to sell it, I want to market it for people. Autonomy and agility is my goal. All these guys like: Carlton, Jimbo, Kennedy and the late Gary Halbert have that same real world no nonsense… ok ok, no bullshit and “do it” attitude. Thank all of you!
    I finishing it off and posting by this weekend.

    P.S. I will post here again and give an update soon on my results.

  • Gary Pearce says:

    So Funny Jim mate, My favorite word in all this was the perfectly placed “rarely” in this paragraph:

    My point is that unlike plunging off the Hillary Step, failing during a roll-out rarely involves bouncing off rocks like a ragdoll for thousands of feet until your battered frozen body is wedged for eternity inside some lonely glacial crevasse.

    So So Funny!

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