I will try to be brief. Please understand that it has taken me five years to write this article, so if I cannot be brief, please forgive me.

Long ago, before I started this company and before I started this blog, I realized there was something wrong with marketing and sales training. It wasn’t right. It’s not that it wasn’t working, per se. It was working okay, I guess. Buyers were happy enough. It just wasn’t right.

You read a book, you got what you could out of it, and you tried to apply it as well as you could, given the constraints of your resources and capacity. It seemed that there was perhaps a better way, and that nobody had found it yet. I started making my own training and development guides, figuring I may as well try my hand at it. But still.

People were paying attention to why people buy generally. But nobody was even considering what made people buy specifically.

What makes a person buy something completely new, something they’ve never even heard of before? What kind of person does that? What weird and wonderful path must they walk to arrive at a space and time where they say, “Yes. Yes, I think I would like to buy that?”

What makes a person buy a service as opposed to a product? Surely, it must be different? But conventional marketing training says that no, marketing is marketing. It seemed like that couldn’t be all there was to it, but what did I know?

What makes a person buy a one-time service? Is it different from what makes them buy a service they’ll use again and again? Do we do something different when we don’t get a do-over — like getting our house painted or our wedding photographs taken — as opposed to something we’ll do again and again, like getting our nails done or our back massaged? Surely it’s different, I thought.

But conventional marketing training said no, buying is buying.

And if a transaction has more than one part, do we act the same in part two as we did in part one? Do we buy the shoe polish the same way we buy the shoes?

And what about from the seller’s side? When we learned something new — in a blog post these days, or a seminar or newsletter or even a book, back in the day — we had to think, how does this apply in my situation? And if it didn’t seem to apply, the person doing the teaching kind of said, “Yeah. Gee. I guess that won’t really work for you.”

If we found a teacher we could trust, we begged them for more detailed information. Action steps! Specifics! What do *I* do? What do I do *next*? What do I do *now*?

I teach marketing for a living. I understand that desire. People beg for it. Yes, but what can a photographer do? What can a craftsperson do? A dog walker? A coach?

I didn’t know how to improve things. If I created general training, it couldn’t help any one individual as much as they needed to be helped. If I created specific training, I couldn’t help enough people. Plus, it’s not financially viable. Copywriting for Dog Walkers would have to be VERY expensive to keep my people in health benefits.

I did a lot of private coaching, but there are really only so many hours in the day.

So I decided to do go away and not come back until I had the answer.

Hi. I’m back.

First, we’ll talk about how this applies to you. Then we’ll talk about how it applies to your customers.

Existing and accepted marketing theory says that you based your marketing strategy around, essentially, your resources. If you could afford big, splashy stuff, you should do big, splashy stuff. If you couldn’t, you should do some other next best thing and pray to the Patron Saint of Big, Splashy Stuff that one day you’d have more resources.

Failing that, you could pray to the Patron Saint of Cash-Strapped Business Owners and hope for some mercy.

If you think about it for long enough, you’ll come to the conclusion that this method is dumb.

You should really base your marketing strategy and tactics on how people tend to buy what you happen to sell.

Well, again, that’s not exactly rocket science. You’re going to sell soda differently than you’re going to sell a house. Sure.

But it turns out, there’s a system.

The way you sell what you sell is actually based around how often people are likely to buy it.

This is why, as a wedding photographer, you’re so frustrated when your friendly local marketing expert tells you how important it is to get repeat business.

This is also why, as an esthetician, it never really made sense when you were hearing how crucial it was to get new customers when, frankly, you had tons of customers already.

This is also why, if you sell handmade jewelry, absolutely nothing seems to apply to you.

We’ll come back to this.

So, one of the things I did when we went on our little marketing vision quest is talk to people. I’m pretty sure we spoke to, surveyed, watched, interrogated and harassed approximately 7.2 billion of them. We talked to ittybiz owners and customers and children and adults. We talked to Canadians and Brits and Americans and Australians and Germans. We talked to people in France and people in Turkey and people in the Czech republic and people in Greece and people in Italy.

(Although, to be fair, the people I talked to in Italy were mostly interested in talking about drinking a lot of wine, but that’s because I was on vacation. Also, Germans tend to demand refunds a lot, but that’s neither here nor there.)

We watched them shop. They showed us their junk mail and told us what they thought of it. They showed us what they bought. They told us about what they didn’t buy. We asked them how they liked to shop. We asked them what infuriated them.

We asked them what made them buy forever.

We asked what made them never buy again.

We asked what kind of annoyed them but they kept buying anyway.

Here’s what we found out.

The psychology of purchase when the person buys a first thing is very, very different from the psychology of purchasing a second thing.

The only research I had seen investigated the brain when it buys the first thing, but other oft-cited and well proven statistics show that it’s (around) 13 times easier to sell to an existing customer than it is to convince someone new.

So if the existing customer is the Holy Grail, why were we only studying the brains of people who hadn’t bought anything yet and basing our marketing strategies on them? What if we studied customers’ minds instead of prospects’? What would it change?

Well, I like nothing better than spending a very long time stalking strangers and calling it work, so I decided to find out.

Why people buy the first thing

People buy the first thing for many surface reasons but essentially, they move towards hope and away from fear. That’s pretty accepted among marketing nerds.

But here’s the interesting thing. After the first purchase, the hope and fear thing tends to fade and the buyer’s normal personality is much more likely to come out.

If you’re generally happy, you’ll shop happy. If you’re generally depressed, you’ll shop depressed.

If you’re generally logical, you’ll shop logical. If you’re generally emotional, you’ll shop emotional.

Cool, right? Well, yes. Cool, but useless.

Then we ran the math and things got a whole lot cooler.

Amy is a basically happy and logical human being. She’s reasonably confident, mostly optimistic, and her purchase is a fairly logical act. She has a high risk tolerance.

You rolls the dice, you takes your chances, but on any given day, as long as you sell something reasonable, Amy is around 80% likely to buy whatever you sell her next. (The numbers are rounded, but I have a feeling you’re not as much of a stats nerd as I am.)

If you offer, and do it properly, 4 out of 5 Amys will just go ahead and buy it, almost no matter what.


We talk in-depth about Amy right here.

Bob, on the other hand, is capable of happiness, but tends towards stress and anxiety. On the surface, he seems quite logical, but his buying behavior is driven by emotion. He is anxious, concerned, and risk-averse.

He’s around 60% likely to buy.

We talk in-depth about Bob right here.

Carol is happy and confident like Amy, and they share the same high risk tolerance. She’s emotionally driven, like Bob, but unlike Bob, she only makes the most cursory attempts at appearing logical. She LOVES to shop.

She’s around 40% likely to buy. That’s not a typo.

We talk in-depth about Carol right here.

Daniel tends towards depression. like Amy, he’s very logical and loves efficiency. Like Bob, he’s pessimistic and has a low tolerance for risk. At any given time, he’s pretty sure things are not going to work out in his favor.

He’s around 20% likely to buy.

We talk in-depth about Daniel right here.

This part is really important.

So, in that part about Daniel up there? Where we said he was only 20% likely to buy? And we kind of get annoyed and we don’t really like him very much because the son of a bitch put his Visa back in his wallet? Do you get what that means?

That means that of your most cynical, jaded, depressed, eye-rolling customers, the ones most likely to mope and moan and get irritated, 1 out of every 5 of them will still buy your upgrade, upsell, or cross-sell.

And he’s your worst case scenario.

Take a minute to consider what your upsell, cross-sell and upgrade strategy is at the moment. Do you think you might change it if you knew 20% of even your most depressed and jaded customers would buy more stuff, as long as you presented it right?


But hang on a second. The title says “Your 5 Customers”! That’s only 4!

This brings us to customer five, otherwise known as, “the reason you’re terrified of upselling, cross-selling, upgrading, or getting the maximum potential revenue out of your customers and clients.”

Meet Auntie Vera. Auntie Vera is angry. Very angry. She has a highly dysfunctional relationship with commerce. She takes all but a very few commercial transactions personally. She yells about junk mail. She screams about sale signs in the mall. She spends a lot of time bitching in social media.

Something inside her feels ashamed that she bought something in the first place, so asking her to buy again is like backing an animal into a corner.

She’s about 0% likely to buy and 100% likely to complain her Congresswoman.

We talk more about Crazy Auntie Vera right here.

The reason you pull your punches when you’re selling stuff is because while Auntie Vera represents between 1 and 3 percent of the buying public, she’s also the loudest. By far.

On some level, we think Auntie Vera is the majority. She’s the majority of who we hear from, so we think she’s the actual majority. She squawks when we sell, so we don’t sell. What we don’t pay attention to, however, is that she was going to squawk anyway.

Back to the system.

So here’s what we’ve done.

We’re completely changing our training based on learning tracks.

If you’re a service provider and it’s reasonable for someone to buy what you sell more than once a month, you take track A. Life coaches, estheticians, dog walkers, acupuncturists, massage therapists, and ghost bloggers, I’m talking to you.

If you’re a service provider and it’s not likely for someone to buy what you sell more than once a month, you take track B. Photographers, interior designers, animal hotels, web designers, and wedding harpists, I’m talking to you.

If you sell products, you take track C. (And if you’re feeling industrious, think of whether your customers are likely to fit in the “more than once a month” or “less than once a month” category. Then give a few of those modules a glance, too. Neat, but not compulsory.)

Very soon, our first learning track-based course Same People, More Money will be available.

You’re going to learn about how to sell what YOU sell to Amy, Bob, Carol, and Daniel. You’re going to learn how to deal with Auntie Vera.

You’re going to learn about the five places in the upgrade process and what (and how!) to sell in each. (An add-on at the point of purchase is not the same as an upgrade months later, but we’ll tackle that and a whole lot more.)

You’re going to learn why your existing upsells, upgrades, and cross-sells aren’t working, and stupidly simple ways to turn it around.

You’re going to learn how to overcome the hurdles your customers have. (How to not BE icky.)

You’re going to learn how to overcome the hurdles you have. (How to not FEEL icky.)

You’re going to learn whether your customers and clients are Amys, Bobs, Carols, or Daniels — I’m pretty sure you can spot your own Veras — and you’re going to learn how to tailor your offers to maximize your success with each.

You’re going to learn how to sell to a group of strangers without spooking the hidden Bobs or pissing off the lurking Daniels.

And you just might learn what I got up to in Venice.

So, my apologies for being gone for so long. I hope you’ll find it was worth the wait.

Welcome to Act Two.

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