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How to Get Lifetime Customers with Stellar Emails: 5 Wine Businesses Doing it Right

Imagine this:

You start getting repeat orders from email subscribers.

You no longer spend so much on acquiring new email subscribers.

You get more than ¼ of your revenue from simply sending out emails to readers.

But here’s the catch:

You have to stop sending so many discounts…

...So that subscribers choose you because you answer their questions, overcome their objections, and show them why you’re the right choice over competitors.

Yes, it’s a long game and you won’t get so many sales right away.

It’s a lot of work in the beginning, but what if it meant you could stop leaking thousands of potential buyers to your competitors?

Would you do it?

The five wine businesses whose emails I chose to break down do it brilliantly. I’ll explain why they’re so effective so that you can learn how to stand out in the inbox and use your company’s strengths to beat your competitors.

Wine Folly

Let’s start with Wine Folly because it’s Canadian and I’m Canadian.

Canadian Pride, YEAH!

It makes me incredibly excited that there’s such an awesome wine newsletter in Canada. You know how I know they’re doing so well?

I was going to buy some products from them last week and most of them were out of stock. These are things like charts, journals, wine-tasting kits, etc. It’s not like selling your own wine that when you’re out of stock, you’re done for the entire year. You can’t just whip up more wine, but I’m sure you can whip up more charts and things like that.


Let’s take a look at this email:

1. If you know your readers well, then you’ll know exactly what to email them to remove the mental barriers they set up to buy from you.

Wine Folly does this well.

Lots of people who love wine and want to know more about wine want to feel more confident about tasting wine and ordering wine. It’s what drives them to buy wine.

No one likes trying to pick out of thousands of options if they’re only 35% sure that they’ll enjoy their choice.

So if you’ve been wondering why many of your email subscribers aren’t buying from you, it has to do with much more than the price. Address other buying objections your subscribers might have by listing all the reasons why they’d be hesitant to buy.

Then, answer those objections. Use every answer as a subject line. Elaborate in the email. There, I just gave you a bunch of ideas. You can even write them down now and then get back to reading this.

2. Email is a written conversation. It allows you to connect with another human being, no matter where that person is located. When you can connect with another human being, it becomes easier to trust her, and eventually buy from her.

Madeline from Wine Folly completely understands this. That’s why she includes her name beside the company name. She wants to invite you into the email for a conversation.

Now, I’m not saying that you can’t just use your company name. You absolutely can as long as the body of your email helps your reader overcome an objection. Either way, always test what works best for you.

3. Madeline starts off the email beautifully: by addressing the problem that’s now on the reader’s mind. Now, the reader will want to find the answer to that problem. She provides a link if you’re ready to take a look at some ways to solve the problem.

4. She also gives a visual representation of the problem and the solution so that the reader can quickly interpret how to go from having a problem to solving it. That’s a good way to use a graphic because it actually enhances the email copy, making people interpret the information faster. You never want to include a graphic just for a graphic’s sake.

5. Then, Madeline goes into the reasons why the reader should go for that particular solution. It gives the reader another chance to go for the solution if she’s ready for it.

6. If the reader isn’t ready, Madeline provides social proof that others just like the reader have enjoyed the solution and why. Reviews and testimonials like these are always great ways to strengthen the trust between you and the reader. It’s a chance to show the reader that you’re not just selling fluff, you’re selling solutions and experiences that have made others happy.

7. Here’s the reader’s final chance. Notice that Madeline isn’t talking as much about selling products as she is about selling solutions to readers’ problems.

I can tell that Madeline’s playing the long game with readers.

She placed multiple links in the emails and she always wants readers to have as much knowledge as possible before they make a decision to buy something wine-related. Since she’s the one giving readers all of that information, who do you think they’re going to go to when they realize they need to buy a wine-related product?

Probably Madeline at Wine Folly.


Not to be confused with “The Wine Society”, these guys are the new kids on the block.

And guess what?

They’ve got canned wine! Apparently, it tastes pretty good. Unfortunately, I wouldn’t know because U.S. wine doesn’t ship to Canada. (Come one guys, it’s 2020. Loosen up the alcohol restrictions.)

But I can analyze their emails.

Here’s everything that WineSociety gets right:

1. Questions can work extremely well, but only if you use them sparingly. Just like with discounts, you don’t want to bore your readers with the same types of subject lines all the time. WineSociety hadn’t sent me any questions yet, so when they sent me such a straight-to-the-point subject line like this, it worked.

Why did it work? It addressed me directly. It implied that I had forgotten something valuable. It implied that I already started to do something. When you get ideas like that into your reader’s head, oh boy, that makes them want to finish the task.

If you haven’t asked your reader a question that’s personal and direct in a while, try doing it this week. It could be as simple as “Do you want a Crisp and Light White Wine right now?”. Try it.

2. People get a lot of emails. Naturally, some people will forget about the discounts and offers they’ve received just because they were inundated with so many other emails. Don’t punish your reader for that. Instead, remind your reader that their discount is still available like WineSociety does in this email.

It doesn’t look like a hard sell, but it is. They’re just checking in like a friend. Notice how they use “reward” to make their discount sound different from others. If you’re going to send an email like this, try using similar language so that the reader feels special for their efforts of signing up to your email list.

3. If you’re promising a discount, you have to explain how to use it and what it is like what WineSociety does here.

4. This is a great image of what an email subscriber can look forward to receiving after they place an order.

5. Perfect CTA placement. Simple and tells you what you’re getting.

6. Again, really personal email copy. They focus on showing you what’s going on rather than telling you. You always want to get your readers to visualize by using language that gets them to imagine a scenario.

Use this type of email when you haven’t used a question subject line for weeks. It’ll intrigue the reader and make them want to see what the email’s about. In the email, you can either be quick and simple or you can use the email to teach your reader more about wine.

Wine Enthusiast

Wine Enthusiast has been around for decades. They even have multiple email newsletters for different topics. I forgot which newsletter I subscribed to, but I had to break down this email that tackled an important question for emerging wine lovers. If you want to read some of the best information online on the topic of wine...Wine Enthusiast is the place for you to be.

Now, let’s go through this email:

1. This is a brilliant subject line if they got their segmentation right. I’m definitely in the right segment because while I know quite a lot about wine, I’m still no expert. That’s why the conundrum of “Should I Decant?” is a perfect one to throw at me. You always want to make sure that you’re throwing relevant conundrums at the right people at the right time in their journey of getting to know a product.

2. When you open up the email, you can feel that they’re with you. They get it. Your question is a hard one to answer, however, they’ve made it easy for you by pointing to an article all about decanting. It would be nice if they included an infographic within the email so that I wouldn’t have to leave it to read the article. This way, I’d see the next block in the email and realize they can solve my issue of decanting.

3. Makes sense that they’re selling decanters in this email. Makes even more sense that they’d mention best-selling ones. It’s a great way to include social proof without using reviews or big testimonials. A way to go deeper on this is to explain which decanter would be best for a certain wine or occasion. That overcomes another objection that your reader would have before hitting the ‘buy’ button.

4. High shipping costs are a big deterrent for many people. Why would you get something delivered if the price of shipping is the same as the product itself? That’s why it’s always a good idea to include information on shipping and how buyers can get their shipping costs down. It would be great to see the conversion rates on these emails if the shipping information was bigger, bolder, and higher up in the email.

The “When to [Do/Use Something]” email formula would be a great one to use when a holiday or special event is coming up.

For example, “When to pour Cab Sauv vs. Pinot Noir”, “When to use an [type of glass] Wine Glass”, or “Who Should Buy [Type of Product]”.

The Small Winemakers Collection

I’m a subscriber of MANY winery newsletters. (Yeah, sue me.)

But the ones who put their heart and soul into telling their readers about the origins of the wine give me the most joy. I’m sure I’m not the intermediate wine lover who’s always trying to learn more about the story of a wine, where it’s from, and how it’s made.

That’s why I wanted to break down this email from the Small Winemakers Collection. Also, they’re based about 40 km southeast of me, so I thought it would be cool to break down a winery email from a “neighbor” ;)

1. When you mention a particular type of wine, obviously you’re limiting yourself to the people who love that type of wine or to people who want to get a present for people who love that type of wine. Contrary to popular belief, limiting your audience is not a bad thing. The more specific you get, the more likely that your audience will buy from you because those are their exact tastes.

This subject line spoke to me in particular because 1) I love a good Syrah 2) I’m a big fan of history so “oldest winery in Morocco” made my eyes light up.

2. Since I’m subscribed to so many wine lists, I often forget the sender of the email, unless it’s coming from a person from the company (like Wine Folly). A lot of the readers on your winery newsletter like me, will be subscribed to lots of winery lists. That’s why it’s a good idea that the Small Winemakers Collection reiterated who they are at the top of the email. They import fine wines. Right, thank you for reminding me. I totally forgot about that!

3. When you’re featuring one specialty product on display like wine, cheese, organic clothing, chocolate, coffee, etc., including product details is always a good idea. People like having the option to do their own research, knowing the price before they click through, and seeing the process they have to go through to get the product.

4. Let me tell you why you want to write stories like these to your email subscribers:

Chances are, the subscribers who stick around to read these stories the whole way through are going to be your lifetime buyers. Why? They’re buying the wine because it’s a lifestyle choice, not because they need to make a quick decision for a party gift. It won’t matter that emails like these take longer to read than 8 seconds. A person’s attention will stay on whatever’s important to them. The more you teach them about what they want to know, the more likely they are to buy.

5. When you’re selling wine, the easiest objection to overcome is how to drink the wine. Most of the time, people don’t drink wine as is. They pair it with food.

6. Again, they’ve provided a simple way to order. Beautiful.

7. I love this sign off. It’s simple and I know exactly who’s been emailing me.

8. Just because I don’t want to take the current deal, doesn’t mean I’m not interested in whatever else they’re offering. Email subscribers are bogged down by hundreds of emails per day so they might’ve missed your previous emails and don’t want to go through the hassle of reading through every email you’ve sent. A small link to your website is a great way for them to explore other options.

If you sell high quality products like the Small Winemakers Collection, the best way to build trust and excitement for your next email is to tell your email subscribers all about your products. People want to know what they’re investing in and they want to teach their friends all about it.

Wine Awesomeness

These guys do curated wine boxes from around the world. They tell the stories behind the wines and they offer packs or cases. They paint a great picture and always make you wonder what’s in the email.

Let’s take a look:

1. I’m usually not a fan of emojis. A lot of companies use emojis for the sake of emojis, but Wine Awesomeness used it correctly this time. Why? Because they replaced “glass of red wine” with the emoji instead of just adding it on to make the subject line stand out. Either way, this subject line stands out because “gulp-able” doesn’t often come to mind when you think of a red wine. That’s more for fruity, white wines (at least for me).

2. This is a nice, simple graphic that shows the reader what they’d be getting if they order a Douro wine.

3. Now, here’s the story behind the “gulp-able” red wine. It’s a great use of showing rather than telling, taking you out of your inbox and through the vineyards of Portugal. Readers love going on a journey in their inbox. It’s crowded enough with ads and work emails so help them relax.

4. Reiterating free shipping is always a good idea, especially after you took the reader on a journey. Travel is expensive but your shipping doesn’t have to be!

5. These are great details that people often wonder about when they’re buying wine. Wine Awesomeness did a great job of answering them succinctly.

6. They also make it really easy to order the option you want. Anymore than three options and people tend to get overwhelmed.

7. They also handle reader objections about discounts and expiration dates. I love how they do this because obviously they’re not putting a big emphasis on scarcity. They’re putting a bigger emphasis on the quality of the wine, otherwise they wouldn’t have bothered to tell the story behind it.

Wine Awesomeness does a great job of taking you on a journey and teaching you about your wine, how to drink it, and what to drink it with. They also make it incredibly easy for you to figure out how to order it.

How to Get Lifetime Customers vs. Customers Only Waiting for “The Deal”

1. Teach your readers something that they’d wonder about. Make them feel like they’re a part of the wine people club. When people want to explore something like wine, it can be intimidating to join the experience because there’s so much to learn and movies have given it a bad reputation for being snobby. When you teach people more about wine, it makes them feel more confident, and therefore want to be a part of the journey and buy wine more often.

2. Remove objections that email subscribers would have before ordering online. This means making it easy to order and being transparent about shipping costs.

3. Have the same call-to-action throughout the email. You want your subscriber to take one action. It’s best not to overwhelm them with many options, however, you should always test to see if having an option to see other products would also work.

4. Only discount when absolutely necessary. When you discount, give a reason for your discount so that the reader knows you’re not just doing it for the heck of it.

5. Tell interesting stories that readers can tell their friends at a dinner party, their spouse during an anniversary dinner, or to family during the holidays. Wine is an experience and it’s meant to be shared. When was the last time you poured someone some wine and they didn’t ask you all about it?

Think about that.

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