How To Email Your List

How to email your listToday we are talking about how to communicate with the people with the money in a way that does not turn you into:

a.) an irritating pest,
b.) a marketing skeezy pants, or
c.) someone they hear from so infrequently, they don’t remember your name.

I think we can both agree that those are bad things you do not want.

But! Problems! Danger!

If you avoid C, you might end up being A or B. Everyone will hate you and mark you as spam.

If you avoid A and B, you’ll probably end up being C. Everyone will forget you and mark you as spam.

Fun, right?

Hello, rock. And hard place! What a surprise! We really must stop meeting in such close quarters like this. People will talk.

OK. Let’s get on to the good stuff.

How often can I email my list?

You may email your list as often as you have something valuable to communicate to at least 20% of them.

So if you have 500 people on your list, and it’s not unreasonable to assume that 100 of those people will gain some potential value from hearing what you have to say today, feel free to email them. Even if you emailed them yesterday.

Now, if your potential financial payoff is particularly high and you can limit the irritating or skeezy quotient, you can email when you have something to say that would be potentially valuable to 5% of your list.

For example, if you are opening up private coaching and there’s a good chance you’ll make $10,000, annoy whoever you need to annoy. You’ve got ten grand worth of skin in the game.

But won’t they unsubscribe/unfollow/de-friend/shoot me?

Definitely. It’s part of the game. You really need to try and get over that. It’s hard as hell, I know, and you’ll never fully succeed. But you have to try.

Try to remember that people sign up for mailing lists or blog feeds or social media updates for some VERY bizarre reasons.

I received a nastygram from someone once who told me they were annoyed I kept selling things. They were only subscribed because they thought I might actually show screenshots of a topless Skype call.

I have heard from someone who was upset that I kept telling personal stories since they’d only subscribed so they could put me in their swipe file of subject lines to steal.

I have been told on more than one occasion that the only reason they signed up was because they were drunk and bored.

Weird, anomalous subscribers become weird, anomalous unsubscribers. IT’S FINE.

Your list is NOT a list of hot leads. Your list is a motley crew of random internet strangers, some of whom are hot leads. If non-hot leads unsubscribe, you MUST STOP CARING.

No, but seriously! Every time I mail, I get unsubscribes! Every time!

Yes. So do I. And it’s hard to click “send” when you know it’s going to make certain people click “spam”. I know that.

But let’s look at some math.

If you email 200 people and 4 of them unsubscribe, you lose 4 people.

If you DON’T email 200 people, you lose 200 people.

And the 196 people who LIKE hearing from you get totally screwed out of the kind of stuff they signed up for because you’re freaking out about the four.

That’s really dumb and you have to stop doing it.

OK, but how do I know what’s “potentially valuable”?

Well, think of the things you’re a relatively active fan of. What do YOU find valuable?

I’m subscribed to six blogs. One I read religiously. I click refresh to see if it’s come in yet. The second, I read maybe half the articles. The rest I read about one in five of their posts, generally based on the compellingness of the title, but sometimes if I’m trying to avoid work I’ll read all of them at one time, plus back posts.

(This means include links to your other, or recent content. I’m bored! Give me something fun to do!)

I probably open 3 out of 5 emails from Sunwing Vacations. They have sort of a “deals of the week” newsletter that they send out, and I read it more often than I don’t. (It should be noted that the last time I took a vacation through Sunwing was when I went to Cuba – years ago. I’m still reading.)

Norwegian Cruise Lines sends me probably four emails a week and I at least glance at about half of them, even though their “sales” are hardly sales at all. (Norwegian: I adore you. More than you could possibly know. But onboard credit is not a sale, it’s a bonus. I like both, but one is not the other. A dog is not a cat, and you can’t say it’s a cat just because cats get a higher open rate. It’s cheating.)

Given that the average launch gets 50-60% of its sales on the last day, and 50-60% of THAT in the last few hours, I mail twice on the last day. So should you. You think everybody’s heard about it, and you may, theoretically, be right. (You’re not actually right, but you could be in theoretical alternate universe land.)

Just because they’ve heard about it doesn’t mean they haven’t forgotten about it. You know, maybe I’ll say that again in bold. Just because they’ve heard about it doesn’t mean they haven’t forgotten about it. People are busy. They don’t spend their entire day thinking about you and your fantastic offerings. You MUST tell them again. And again. And again.

OK, I get that I have to mail. But what should I say?

Start with the simplest possible version of the truth you can think of. Get fancier as you get better at it.

If you don’t know what to put in your subject line that’s introducing your new line of jewelry, start with “We’re introducing a new line of jewelry”.

As you get better, start throwing “limited edition” or “get it while it’s hot” or “sale ends Tuesday” in there.

For most people, that’s really all you need to do if the communication is primarily commercial.

If the communication is pure content, or more content than commerce, lead with the title. If your ittybiz is at the point where you already have serious fans, put the title in sentence case. It makes you look friendlier. (This means capitalize the first letter, but not the first letter of every word.)

If you don’t have serious fans yet and you’re still proving yourself, you can leave it in title case. It makes you look smarter. (This means capitalize the first letter of every word, or the major words.)

Don’t put “newsletter” in your subject line. It’s a waste of ten characters, eleven if you include a colon, or twelve if you include square brackets. That’s just wasteful. This also applies to your name or your business name, unless it’s contextually relevant and necessary. They know who’s sending the email. That’s what the Sender field is there for. (Example: “IttyBiz is having a sale!” is fine. “IttyBiz: How To Write A Better Tagline” is not.)

Whatever. I’m still freaked out and confused.

OK, if you take nothing else from this article, take this:

The purpose of your list is to give people who like you the opportunity to hear what you say and buy what you sell.

Therefore, you must say it. And sell it.

It’s like reruns. People will watch their favorite TV show every day of the week, no matter how many times they’ve seen the episode. And if they don’t watch it, they still want to know it’s on. They might want to watch it, and if it went away, they’d be sad.

Your job is to become their favorite TV show.

You’re not going to do that by airing an episode once every five months.

The truth is, if you email your list frequently, whether it’s once a week, twice a week, or hell, even five times a week, EVERYONE will unsubscribe except for the people who love what you say and what you sell.

But here’s the secret…

They’ll bring their friends.

My point here is not that you should overwhelm your list with emails, especially if you don’t have anything valuable to say. My point is that you should write to the people who love what you say and what you sell, and give them as much good stuff to love as you can.

That is the only sustainable way.

Naomi writes more things like this in The Letter. Get it for free today. (It also comes with free marketing courses. You can’t move for free here.)

Your 5 Customers, or How To Sell To Damn Near Anybody

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.

When You Feel Like A Raging Failure

(Originally published in 2008)

You’re not alone.

I’m typing this in bed, on the new laptop my IttyBiz readers bought me. (By the way? Thanks for that.) To my right, on the floor, on Jamie’s side of the bed, sit two Macintosh computers. They belong to my mother. For those of you who are new, I’ll take this opportunity to mention that my mother moved to Europe in 2005. I have yet to get off my ass to put them in storage.

To my left is a floor full of books. They used to live in my busted chipboard bookshelf, but Jack likes to play with them, taking them down and putting them back in an order he feels is more appropriate. The last time he played this game was about 10 days ago. The books are still on the floor. Neither of us can get into bed from the sides, so we come up from the foot.

Jack is covered in a rash from ankle to neck and scratches himself every hour of the day and night. My bathtub is full of baby sleepers and cold water where I tried, and failed, to get the blood out of his clothes. He is crying in his room and Jamie is trying to comfort him — nothing I was doing was helping and I am now under my covers sporting silent headphones, trying to drown out the noise so I can cry and type in peace.

I fear he either has or will shortly get an infection from the cuts that don’t heal, and all the doctor does is tell us to try Aveeno. Because I guess we never thought of that.

I missed a client call. I want to reschedule but everything is so up in the air, I don’t even know when to tell them. I feel horrible, guilt-ridden and sick. I feel like I’m drowning. I feel like my home business, doing what I love, is a fabulous sparkly present and I’m stomping on it daily.

I feel like every time I screw something up, little bits of sparkle wash down the drain and soon I will be left with nothing. I don’t know how in the hell I’m ever going to deliver on all of the promises I’ve made — promises I want to keep, promises I had every intention of keeping, promises that I didn’t think would be a problem.

There is no how-to in this post. I do not know how to dig my way out of this. Sometimes when something is wrong, it’s helpful to pretend that the problem belongs to someone else and you can think of the advice you’d give them. Unfortunately, under these circumstances, my advice would be trite and ridiculous. I would tell people to plug away, item by item, list by list, until they had fought their way out.

I think we all know that’s delightful advice in a vacuum, but it doesn’t account for emotional states that include bursting into tears watching Ellen give away $100 gift cards to Trader Joes. Overwhelm does not occur in a vacuum and vacuum advice doesn’t help worth a damn.

The only thing I really hope to accomplish with this post is this: If you feel terrible, you’re not alone. If you feel like, now that you’ve got your itty bitty business off the ground, you’re furious with yourself for not skipping with glee every moment, it’s not just you.

If you feel like nobody on the damn planet understands what you’re going through, at least I do. If you feel like, now that you’re at home full time, you should provide your children with home-cooked meals and wash the sheets every other day and only show quality, commercial-free programming on your television and have sex with your husband six nights a week and have a floor that’s more carpet than ground-up-Cheerio, you’re not the only one.

1 2