How to Spot a Con Man

Sleazy guy two thumbs up

During my career as a freelance copywriter, I’ve encountered a few exceptional negotiators and a handful of con men.

How do you spot a con man? First, it helps to know the definition.

According to Princeton’s WordNet, con man is short for “Confidence Man: a swindler who exploits the confidence of his victim.”

With that in mind, here are three traits to watch out for.


This is the first and foremost thing to look out for. A compliment is normal. Flattery is not.

Whenever somebody flatters me, I watch my wallet. Flattery is normally a prelude to an unusual or out-of-the-ordinary request.

The psychology works like this:

Flattery makes you feel all puffed up and great about yourself. But this is a set up so you’ll agree more easily to whatever request comes next.

You are more likely to make a bad decision when you are feeling overconfident. Flattery is an easy way to build your confidence.

“…a flattering mouth works ruin.” Proverbs 26:28


A person who brags is not necessarily a con man; he could just be insecure.

It’s the type of bragging that matters.

Some people brag about how good they are at a specific skill. This is your garden variety braggart, relatively harmless.

Others brag about their good character or how much money they give to their church, poor people, etc. This is your con man variety of braggart.

It is designed to get you to lower your guard… to get you thinking about what a good person it is you’re dealing with. Next thing you know, the con-man lowers the boom.

Watch out for people who brag about their good character.

“But when you give to the needy, do not let your left hand know what your right hand is doing, so that your giving may be in secret.” Matthew 6:3,4

Unrealistic Promises

A common negotiating tactic is to build neediness in the other party.

For instance, a potential client might tell you that there’s “huge” potential, and that you could make “tens of thousands of dollars.”

He’s building your confidence to the point where you believe this future pay-off will really happen.

The next thing he’ll do is ask you to work for free for an indeterminate amount of time. If you believe the vision he’s painted, you might agree to unreasonable terms, work hard for months… then never see a single cent.

“Like clouds and wind without rain is a man who boasts of gifts he does not give.” Proverbs 25:14

Safeguard Yourself

A con man uses all kinds of techniques to build your confidence in yourself and in him. Once your confidence is high enough, you’re in a vulnerable position. That’s how you get conned.

Ask yourself: “Am I feeling overly confident? Why?”

Ask yourself: “Why is this person flattering me? Why is he telling me all about his good deeds? Why is he promising me a huge pay-off somewhere down the road?”

Answer these questions. Be honest with yourself. Don’t be taken in.

-Ryan M. Healy

P.S. The truth is finally coming out about certain marketers who do business on the Internet. Here are three posts you may be interested in:


  • Stephen Dean

    June 5, 2008

    I swear Ryan, I think we’re on the same page 99% of the time. Of course, a lot of copywriters know exactly what you’re speaking of.

    PS I’ve got your questions answered, I’ve been procrastinating on my questions for you.

  • Chris Lake

    June 5, 2008

    Your post is sage advice indeed. I fell in with a character last year about this time and only six months later realized I had nothing but empty, broken promises to show for my work. It’s easy to see in hindsight, but the overconfidence blinds us in the heat of the moment. I will remember your words next time I start feeling those misgivings.



  • Joseph Ratliff

    June 5, 2008


    I think there are “con men” on both sides of the coin…and it’s really unfortunate for honest copywriters who market value added services.


    There are also so-called copywriters out there who “take the money and run”, and perform very little work for the client in exchange.

    They use “con” to gain the trust of their clients, and once they get that payment…they are gone.

    That, or they misrepresent their level of experience or qualifications etc…and pass it off as marketing themselves.


    Great post Ryan! :)

    Joseph Ratliff

  • Ryan M. Healy

    June 5, 2008

    Stephen – Well, now I know I’m writing about stuff that’s on your mind! ;-)

    Feel free to mirror back my interview questions or similar ones.

    Chris – I can relate. Live and learn, I guess.

    Joseph – I agree 100%. I’ve come across a few potential clients who were really hesitant to pay anything up front because they’d recently been ripped off by a copywriter.

  • IncBlitz

    June 7, 2008

    Hi Ryan…

    I just noticed, isn’t that
    what copywriters do?

    Make the client feel

    Make them feel good
    about themselves.

    Tell them who you are
    and what you do.

    Give credibility.

    Paint the picture of the
    product/service your

    “Future pacing” it so that
    the client feels as if he/she
    already owns the stuff.

    It has parallelisms…

  • Ryan M. Healy

    June 8, 2008

    @IncBlitz – Certainly, there are parallels.

    But let’s clarify…

    A con man is a “swindler.” And to swindle somebody, you must use deception or fraud to take what is not rightfully yours.

    In other words, you must lie.

    I do not believe copywriters are inherently liars. And I don’t believe there is anything wrong with building confidence, so long as that confidence is based on truth.

    For instance, Honda has built confidence that their engines are reliable. Is that wrong? No! Most evidence supports that claim.

    Have I been defrauded by purchasing a Honda minivan? No! I got the dependability of a Honda, just as I expected.