The Ultimate Cheat Sheet For Selling Anything

I was a salesman snob.

Like many people, I always looked down on the concept of “selling.” It seemed like something lower than me.

To some extent, selling appears manipulative. You have a product and you try to portray that it has more value than it actually does. So you need to manipulate people into buying it. This seems sad, as in the book “Death of a Salesman” sort of sad.

I was wrong. And for the past 25 years, all I have been doing is selling. Selling products, selling services, selling businesses, selling myself.

Sometimes I have been manipulative. And sometimes I’ve sold things I’ve had such passion for that I practically gave them away just to get the message out.

And often, it was very much in the middle: I needed to sell something because I had to pay my bills. I wanted to make sure my family got fed.

We live in a hard world where our basic needs cost money, and as we get older we become responsible for the basic needs of others. We become adults.

None of this cheat sheet comes from a book. All of this is from my own experience. Which means it might not work for you. Which means it might go counter to the basic rules of salesmanship. I have no idea.

But I can say that over the past 25 years, I’ve sold hundreds of millions of dollars of stuff. That stuff being everything in Pandora’s box that I had to sell just to stay alive. When I thought of what worked for me, here’s what I came up with:


A) Friendship

Nobody is going to buy from someone they hate. The buyer has to like you and want to be your friend. People pay for friendship.

This sounds sort of like prostitution, and it is.

One time when I was raising money for something, the buyer was going through a business catastrophe and was worried he would go out of business. I didn’t like him but I called him every day for three months at the same time to see if he “wanted to talk” and to offer my advice on how he should deal with his situation.

I eventually raised a lot of money from him even though the first time I met him he said, “It seems like you don’t know your industry very well.”

Which just goes to show that friendship outweighs almost every other factor in selling. One time I wanted to do a website for How did I do it? The main decision-maker volunteered at a school in Harlem. I went up there four weeks in a row and played 20 kids simultaneously in chess. Everyone had fun. I got the website job. My competitors were all bigger, better financed, and probably better.

Unfortunately, I didn’t like either of those people personally. And eventually, I lost the business.

The only good outcomes come when both sides like each other.

Now I only do business with people I like. The fastest way to lose all your money, mutilate your heart, and then kill yourself is to work with people you don’t like. I will never do that again.

Nor do you have to, despite what you might think.


B) Saying no

If someone wants to do a big deal with you, it’s hard to say “no.” But “no” is valuable for many reasons, and one big one in particular:

Opportunity cost. Instead of pursuing something you really don’t want to do, you could free up time and energy to find something more lucrative or something you would enjoy more. Opportunity cost is the biggest cost in all of our lives. We spend it like there’s no tomorrow.

And guess what? Eventually there’s no tomorrow.

When I say “yes” to something I don’t want to do, I end up hating myself, hating the person I said “yes” to, doing a bad job, and disappointing everyone. I try really hard not to do it anymore.


C) Over-deliver

If someone pays $100 and you give that person just $100 in value, then you just failed. You’ll never sell to that person again. someone pays $100, you need to give him or her $110 worth of value.

Think of that extra $10 as going into some sort of karmic bank account that pays interest (as opposed to a U.S. bank account). That money grows and compounds.

Eventually, there’s real wealth there. And that wealth translates into the real world.

People are 3-year-olds. They like to get presents. People want to do business with people who give them presents. Over-delivering is a present. And it makes you feel good. Give and you will receive.


D) Never take “no” for an answer

This statement, which everyone knows, is usually applied incorrectly.

People think it means keep pushing and trying new things until you get a “yes.”

That’s not what it means. If you do that, you end up in the spam box. Then you end up in a coffin. In other words, you end up dead to the person you are trying to sell to.

Instead, remember point A. Be a friend. However flimsy that connection of friendship is. Follow on Twitter, follow on Facebook. Say nice things about the person to other people. Never gossip.

Do the art of the “check-in.”

Send updates after the “no” on how you are doing, on how the product or service or business or whatever is doing. Not every day. Maybe once a month. Maybe once a year. Eventually you will find the “yes” with that person. It could be, and often is, up to 20 years later.

You plant a seed and eventually the garden blooms.


E) Under-price (if it’s your passion)

I once wanted to do the website for Fine Line Films. I loved their movies. I met the guy running their site. He kept saying over and over again, “We can’t afford a lot,” and I kept saying, “Don’t worry about it,” and would show him more and more of our work.

Eventually we did the websites for every one of their movies at $1,000 per website. We made amazing websites for $1,000. Then, when Con Edison wanted to hire us, Nevin at Fine Line was a reference. Price for (a basic four-page website): $250,000. And that was the first of five websites we did for them, plus monthly maintenance.

I write for a lot of places right now for free. Any medium I love, I am willing to write for. The benefits from doing that have been incalculable. Not always financial, but always real.


F) Be the source

One time I wanted to buy a company.

At the critical moment, the owner called me and said, “What should I do? I have this other offer and I have your offer.” He described the other offer to me. I told him to take it.

I missed out on what could have been a lot of money to me. But there was a slight chance we would have all gone bust. Now he is thriving and eight years later he is a friend.

Will we ever do business together? I can’t predict the future. But I know I delivered value to another human being. That value is real and I can put it to use whenever I want.

Often the best way to make friends and customers for life is to direct them to a better service or product than yours.

Be the source of valuable information rather than just the source of your product.

Then they will know forever that you are a trusted source.

Trust is worth more than next month’s rent being paid. Trust builds a bridge that will never wear out. At some point in the distant future, when you are on the run in every other way, you may need to cross that bridge.


G) Sell everything

Your offering is not your product. Your offering is your product, services, your employees, your experiences, your ideas, your other customers, and even (as mentioned above) your competitors. Sell them all.

When you are good at what you do, the product or service you offer is just the way people build the first link to you. It’s the top of a huge pyramid.

But the base of the pyramid, the real service, is when they have access to you and you can provide advice and the full power of your network and experience. This is when you are over-delivering on steroids and how real wealth is built and not just a one-time fee for a service or product.

Many people say, “No! My product is high margin and I want to make money when I sleep.”

Stop going to BS entrepreneurial get-rich-quick conferences. In the long run, nobody cares about your product. In the long run, it is the entire holistic view of your offering, your service, you, that you are selling. Without that, you will build a mediocre business that may or may not pay the bills. With that, you will create wealth.


H) Sell the dream

People can see what your product is right now. What they want to know is the future. Will your product make them more money? Will it get them a promotion?

Everything is possible. When you get in the door, do not sell your product. People make a decision on your product in five seconds. Sell the dream. The dream has infinite value. Build up images of the dream. Give a taste of what the dream is like. Let it linger. Let it weave itself. Let the imagination of the buyer take hold and run with it.

But then, you might ask, do I risk under-delivering?

Answer: Yes. Don’t do that. Be as good as the dream.


I) Fire customers

This is similar to point B with the one difference that you have already made a sale.

If it’s not going well or if it’s leaving a bad taste in your mouth, or if they have gone from friend to enemy for whatever reason and it seems like there is no repair, then fire your customer. The sooner, the better.

This applies to not just customers but everyone in your life. Everyone.

If someone no longer has your best interests at heart, then in your own self-interest, you need to back off. Now.

A bad customer (a bad person) spreads like a disease inside you, your employees, your other customers, your competitors, your future customers, your family, etc.

“But what if it’s my biggest customer? How do I pay the bills?”

I don’t know. Figure it out. This is where being an idea machine saves your life and everything around you.

But remember: bad customers will kill you and your family and your friends.


J) Welcome to the pleasure dome

Your best new customers are your old customers. If you need to make more money or build new business, go to your customers (who are now your friends) and say, “I need advice. What other service can I provide you or anyone you know?”

It might be something totally unrelated to your business. No problem. Do it. It might be your customer is looking for a new job. That’s great. Make it your business to find him a new job. Now you have a new customer.

It might be your customer needs a boyfriend. OK, introduce her to all of your friends who might be good for her. If you’ve been following this approach to sales, then your customers are now your friends, are now your family.


I don’t know the buzzwords to make a sale. I’m not very good at shaking hands. I don’t take people out to baseball games or do any of the things I see other people do.

But I’ve been selling for 25 years. And whenever I’ve been dead broke, depressed, and on the floor, I’ve picked myself up and sold again and again.


P.S. If you are really serious about choosing yourself (and you should be!), then you need to develop a portable, highly valuable skill that let’s you work on your own terms.

Selling is only one of of these skills, but it’s one of the best. If you are seriously interested in learning how to sell, test yourself to see if you can write a letter like this one. 

Share This Post

Other posts you might be interested in: