The Most Awesome Lesson I Learned From Gary Halbert

Wednesday, 1:50pm
Reno, NV
Nothing is impossible for a man who refuses to listen to reason.” (Gary Halbert)


I learned a lot from Gary Halbert, but the lesson that most affected my life had nothing to do with copywriting.

Rather, it was about living well.

I began my freelance copywriting career back in the “dark ages” of the mid-eighties, when direct response advertising had gone out of fashion and there were just a handful of us “true believers” in the game, devouring the ancient (and often out-of-print) books on advertising while doing the hard work of becoming masters at old school salesmanship…

… so we could relentlessly obliterate our clueless competition in every market we went after.


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I was fortunate to live in Los Angeles at the time… because multiple large agencies had just opened up branches there and were starved for competent copywriters. I quickly became the guy the creative directors snuck in the back door to do the work their house staff couldn’t pull off (because none of them studied the craft).

Then the large mailers back east caught wind of my work, and I found myself moving in the “A List” crowd of now-legendary copywriters like Gary Bencivenga and Jim Rutz (who I ghost-wrote for).

However, the corporate world bored me to tears.

It was primarily financial and health newsletters with the large mailers, and insurance and equipment sales with the agencies. Yawn.

That’s when I met Gary, at Jay Abraham’s house. He was the most arrogant, vain and outrageous person I’d ever met in the business world…

… and I liked him immediately.

I began doing odd writing jobs for him, and the day arrived when he asked if I was ready to become his main full-time writer.

The lesson I learned was hidden inside of the ensuing dilemma.

I was a rising star in the corporate world, and the fees (with royalties) were quickly entering “small fortune” territory.

If I went off with Gary, I’d be turning my back on a million-dollar career.

But what Gary offered was a chance to be true to my own mojo. With him, we’d be working mostly with entrepreneurs, and each new gig would be wildly different than the one before. And we’d be ushered into the back-rooms of powerful businesses, to observe and influence how entire markets operated.

I realized how little I was motivated by money. And how alive I felt in the entrepreneurial world, where rules were constantly broken and reinvented, and we could field-test our wildest ideas (the ideas that made the corporate beasts squirm).

Without Gary’s unique vision of how fun and exhilarating advertising could be, I might have stayed in that corporate world.

But we have such a short ride here on earth.

Sometimes, the riskier path is the one you need to take. And damn the torpedoes.

What I learned from Gary over the ensuing decades was both financially and intellectually fulfilling, to the point of being ridiculous. I got to watch the growth of direct response in the nineties from a ring-side seat, and I became a pioneer in online marketing when it became viable in the early aughts. Gary and I produced some of the very first marketing seminars, we invented the Hot Seat method of “speed consulting” with new clients, and we influenced the way nearly all successful copywriting is now used all over the world.

The lesson I learned is simple:

Find out what rocks your boat, and go for it with everything you have.

Gary was the first living example I’d ever met of someone who went for the gusto, every time.

And after 30 years of sharing what I’ve learned, I’m still not done tapping into the deep well of tactics, insight and savvy gathered from the raw wonder of working with the man.

The only way you can measure the worth of your life is later in the game, looking back. With Gary, there were as many misadventures as good ones, and what saved our butts time and again was our brutal sense of humor.

No one here gets out alive, and you gotta play the hand you’re dealt.

There is no room for regret or wishful thinking when you’re deep into life.

Sometimes, the riskier path is the only sensible one to take.

Stay frosty,


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  • Dang it, John…

    I think about the path I took many times.

    About how much “easier” corporate life would have made life now…

    I could slow down a little…

    I’d be “more set” right now…

    and then I think about it a little more honestly…

    and I know the path I did choose was the right path after all.

    Thanks for the lesson.

  • Tom Andrews says:

    Hey John,

    The more I read about Gary, the more I wish I got to meet him. Not only was he a world-class copywriter (and that’s understatement of the century), he also seemed like a top guy.

    Anyway, in terms of your point about taking a risk and doing what gets you excited, I couldn’t agree more. Leaving the corporate world was the best decision I ever made.

    As I was reading, I got thinking… What do you think your life would look like now if you made the decision to stay in that world?

    Thanks for an awesome read, John.


    • John Carlton says:

      I think about that all the time, Tom.

      No good answer, really. I was so bored, I may have drifted off to some other gig eventually. Not being motivated by money kept me loose, and not having a family at the time made moving around easy.

      The way my own life went, there are around 4 thousand decision points that would have sent me off in a completely different direction, all of them leading to lifestyles so foreign to what I do today that it’s like science fiction.

      Worth cogitating on. Really tough to imagine the outcome, though…

  • Marcelo Tolosa says:

    Mr John Carlton,
    Have you ever been so stressed out that you want the day to end but not sure about waking up tomorrow?

    Or just thinking about it makes you dizzy?

    A few years a go a started building houses.

    But to enter the market I was cutting costs like almost giving them for free.

    And I had everyone on my neck.

    Old debts were haunting me. Federal agencies will send people to charge me, my closest workers were abandoning me.

    The construction workers where doing the job pretty badly because I owned and i have to convinced them to work anyways.

    Then the worst, the clients where on my neck.

    And I just needed one more house to keep the circus going.

    And the worst is that I didn’t study architecture neither civil engineer.

    And i wasn’t passionate about this. I hated it everyday and this story was everyday.

    But something gave me relief. I found the during that time.

    And i found that i truly love marketing, sales and copywriting.

    And it was the first thing i will read in the morning and then after coming home.

    So that lesson hit homes with me: “Find out what rocks your boat, and go for it with everything you have.”

    But i don’t regret anything i learned a lot and the idea of working the 9-5 terrifies me.

    Just sitting there and taking orders and waiting so i can go, no way.

    As you pointed out:”I realized how little I was motivated by money. And how alive I felt in the entrepreneurial world, where rules were constantly broken and reinvented, and we could field-test our wildest ideas

    So yes, “the riskier path is the one you need to take.”



  • You guys were rockstars. It’s obvious in the ads you both wrote. I’m in China now, writing copy and doing my best to have as many adventures as I possibly can. Copywriting is a gift and you and Gary have both inspired me to use it to find the best experiences I can. Money’s nice too. Can’t wait for your next book.

  • Joseph Derer says:

    as always great post John…

  • I too have learned from Gary’s lust for life through his writing and the all too brief times I was privileged to spend with him — the adventure of the Key West Seminars, creating mayhem in the streets of Key West and New York City, and marauding through halls of Phillips Publishing.

    And I’ve been lucky enough to continue to get that inspiration from you, John — through your writings like this and our friendship.

    I shutter to think what a more far more boring person I would be today had I not said “Yes” to Gary’s unexpected invitation to join him and you for those seminars, or stayed in the world of ad agency advertising.

    • John Carlton says:

      Hey, DD. Good to see you on the blog, my good pal.

      Yes, you and I have been through a Russian novel’s worth of adventures with Gary. It’s so cool to sit with old colleagues like you and recall both the whacky stories, and the powerful lessons learned.

      I appreciate you more and more as the years slog on…

  • Davin says:

    Do you have any advice on handling the fear and anxiety that comes with the riskier path?

  • Several years ago I definitely took the riskier path, and only this year do I feel that things are finally coming together. Thanks for your advice John.

  • Jimbo says:

    Hey John:

    Another good one.

    Anyone who’s not delving deep into Gary’s old newsletters and sales pieces is missing out. Personally I’ve studied his style and the way he lays out a pitch. Funny. Effective. Masterful.

    I’ll often read a few of his newsletters just as a “warm up” before writing my own sales letter. Just to get the voice on the right path.

    Wild man or not, his work and teachings stand the test of time.


    • John Carlton says:

      They do, indeed.

      I’ve gotta go reread a few myself. I still have the originals, mailed to me in the late 80s. Once I saw the first one (which I stole from John Finn, who had an office near Jay Abraham where I hung out a lot), I was convinced this was a guy I needed to get close to and learn from. It was always risky, but never dull.

      It was invigorating to experience the entire direct response world open up before me as I became Gary’s right hand man. The details alone were staggering (I toured post offices to see how our bulk email was being handled, saw the entire printing process from paste-up to finished product, handled projects from meeting client to cashing royalty check, and more), the rewards staggering, and adventures thrilling.

      It all ended when the Web hit — at least the direct mail part of our gigs. I went online with a vengeance, and figured it out. Gary never did, really… though his advice on life, biz and copywriting in general still holds.

      I was lucky to be positioned between the Old School and the new online world order — feisty enough to make direct mail work, curious enough to be one of the Web’s marketing pioneers… and loose enough to enjoy the entire ride. Lucky me.

      I did the narration for Gary’s most famous letter (The Dark Side of Success) for Bond and Kevin’s project. That newsletter came out, I recall, in either the first or second year of his run. Very early. Very insightful stuff that has stayed with me all these years.

      I didn’t get filthy rich working with Gary, in cash terms. He was too unpredictable and got bored too easily for any long-term projects to pay off. But the knowledge I gained took care of that in short order. Cash can be lost. A vicious skill set, though, can be put to use no matter how broke you get from circumstance or dumb moves.

      Jeez, I miss that guy. I still talk to him, all the time, but I’d prefer him to actually be there to respond, instead of relying on past conversations…

  • Kyle says:

    That was a kick in the ass I needed. Thanks for sharing John, I mean it!

  • Brandon Whited says:

    Hi Mr. Carlton,

    Hope you’ve been well. I’ve been thinking obsessively about the “big” questions. About my own imminent mortality/death, about everything that is “me”. My past experiences, all…

    I have a job interview with Agora Publishing for a copywriter position. Since I left a comment last time Mr. Carlton I’ve been on and off with copywriting and now this is the time to get damn good,

    Get “proven” at Agora.

    I don’t know if I’ll be in California anytime soon. Or if it really matters whether I make it to San Diego or die in Minnesota.

    I’ll be somewhere and that’s alright.


    Brandon Whited

  • Eddy says:

    That’s an awesome story about living the life you want.
    I just recently started on my life as copywriter, after events unfolded directed me to Gary Halbert’s newsletter. I’m soon drowned in his mastery of advertising, life values, and his witty humor. Not until I read Perry Marshall and Dan Kennedy’s books that I found you, John Carlton.
    Right now I’m swallowing everything I can get, but in healthy amount, every world-class lessons on copywriting. I’m still writing mediocre copies, but I hope I’ll improve when I know I’m learning from the best, including you.
    Thanks for your lessons!

  • Little late to the show here, but what a nice piece. Thanks John, your work serves as an inspiration to me and probably many others.

  • Thomas says:

    As always, you seem to have the right words to say at the appropriate moment I need to hear them. Thank-you!

  • Archi says:

    Sir, I have a question,

    How can one practice direct response copywriting in today’s world of the internet?

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