67. The Online Coach’s Guide to What to Email Your List

The Online Coach’s Guide to What to Email Your List

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This episode is the second in a 2-part series on email lists. If you haven’t yet listened to part 1, start here: Episode 65. How to Build an Email List (with & without freebies!)

We’re back to talk all about email lists! In the first part of our series on email lists, we talked all about list-building strategies—with or without the freebies. But once you’ve built that list… what are you supposed to actually send them? Let’s dive into what you can email your list to keep them engaged, how important consistency is, and the different ways you can nurture your audience.

In this episode, you’ll hear… 

  • Approaching your email list with strategy, no matter the size
  • Looking at the big picture in your business
  • The cycle of promotion and nurturing
  • Approaches to the nurturing phase
  • Tips for content and copywriting
  • Ending emails with a question

If you’d like a shoutout (and a chance to win a $20 gift card), just leave a review on Apple Podcasts and send a screenshot of it to me on Instagram via DMs!

The two phases of emailing your list

As you’re building your email list, you need to be sending out emails. Whether you have two people or two thousand, it’s important that you’re consistent and that you’re getting practice emailing your list. But what do you send them? There are two main, cyclical phases in your business: Times when you will be pushing specific things—whether that’s a timed course, in-person events, or sales—and the times when you’re nurturing your list and providing value. You don’t want to just ghost your list until you have something to sell, so you need to be sending emails consistently, either nurturing or selling.

How to approach the nurturing phase

Here are some things you’ll want to keep in mind. Think about what your customers would want to see in their email box—what kind of message is going to get them excited about opening? You’ll want to consider the tone, whether it’s conversational, friendly, funny, educational, authoritative, etc. And you’ll want to know how you structure and design your email. Whatever you choose, consistency is key here.

What to include in your emails

This can be difficult to decide on because there are so many options available, but here are some ideas. You can pair your weekly email with some other piece of content you create, whether that’s a podcast, YouTube video, or blog post. Those can be either consistent or mixed in as they happen, depending on your content schedule. You can treat your email itself as content and use it to directly educate your audience. I like to keep a “sizzle file” of interesting stories I hear about that I can tie into my subject and use in my emails. You can also use your emails to ask and answer questions. Really, there’s no limit to the types of emails you can send. Just get creative and think from the perspective of your audience and what they would want to hear.

Email marketing doesn’t have to be such a hassle. I’ve grown to love it because it creates such a positive community around my business. Hopefully, we’ve taken some of the hassle out of what to write and how to get people signed up, and now you can focus on the fun part: Building a relationship with your audience.

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Resources Discussed in This Episode

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Episode Transcript

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Sam Vander Wielen: [00:00:11] Hey there, and welcome back to On Your Terms. I’m Sam Vander Wielen. I can’t wait to chat with you about email lists today, email list building and what to write to your email list.

Sam Vander Wielen: [00:00:19] So, if you haven’t yet, you’ll want to go back and listen to Episode 65 of my podcast, because that’s part one. This is part two of what to email your list to keep engaged. In part one, we talked about how to actually build your email list, different building strategies. But in this one, we’re really going to talk about what to email your email list. So, I hope you’re excited to dive into this today.

Sam Vander Wielen: [00:00:43] Speaking of email lists, have you signed up for my free legal Q&A called Sam’s Sidebar? Every single Thursday, I send out a newsletter to my list where I take a reader’s question and I answer it for the whole list. People had submitted such good questions lately about, like, how to copyright something and what you should copyright, to what kinds of business insurance you need, to how to follow scope of practice rules as a coach.

Sam Vander Wielen: [00:01:06] I dive into all of your questions there, and so I’d love to see you there. I’ll drop a link below for you to easily get onto my email list without receiving any marketing emails. It’s called the Easy Email Signup List below, I would love to see you there.

Sam Vander Wielen: [00:01:20] Okay. Before we get into this week’s episode, I have to give a shoutout to FFB7 on Apple Podcasts who left a review for the show saying, “Sam was recommended in an online business group and I’m so glad I clicked on the link. She brings so much value in a simple way and helped me keep building an online program without getting stuck on the legal policies. After watching her webinar, I bought the bundle and have been very pleased. Looking forward to Sam’s next training.” Thank you so much for leaving that review in Apple Podcast of my show, On Your Terms.

Sam Vander Wielen: [00:01:48] You can also leave a review and you’ll be entered to win a $20 Starbucks gift card. All you have to do is leave a review on Apple. I pick a new winner every single month and you might even get a shoutout here.

Sam Vander Wielen: [00:01:58] So, in this episode, I dove in deep about what to email your email list, and how important consistency is, how to think of this generally, more like a 30,000 foot view of your marketing strategy, and kind of the different ways that I go about nurturing my email list between promos or sales. I talk about creating a series or referring to bigger pieces of content.

Sam Vander Wielen: [00:02:22] And we talk about, especially for any of you who feel nervous about emailing your list or you feel like a bother or you don’t like to pitch and make the sale, or something like that, I think that I dove deeper than I even had planned to on, you know, kind of some of the mindset strategies, I guess, that I use around this and how this is a muscle that we really have to work to train and strengthen.

Sam Vander Wielen: [00:02:45] So, with that, I hope that you love this episode. I’ll leave some resources for you below. Besides part one of this little podcast series I did for Episode 65, I’m also going to leave the link to Liz Wilcox’s What to Email List Membership. It’s a $9 membership where she teaches you how to and what to email your email list. She’s a wonderful copywriter. So, I will make sure I drop all those for you below. But I just hope you enjoy this episode, and I’ll see you on the other side.

Sam Vander Wielen: [00:03:16] So, I feel like whenever we talk about email lists, it’s a little bit of a chicken or an egg problem, because I feel like people think that you have to get all of these people on your list and, like, focus on that part. But then, they’re like, “Oh, wait. I never thought about what I actually then email those people.” But I can, like, think about what I email those people after I build my list.

Sam Vander Wielen: [00:03:34] And, instead, I kind of see it as, like, this infinite loop that you should be focusing on building your email list, continuously pouring new traffic into it. And at the same time – unfortunate news I guess – you also have to be thinking about and planning for what you’re emailing the people who are already on it. Regardless of whether there are two people, 200 people, 2,000 people, I think you have to give the same energy and attention to what you’re emailing than you do, like, about how people you’re getting on it.

Sam Vander Wielen: [00:04:05] So, we have a hard enough time building our list, and I know we talked about that a lot in Episode 65. I hope you really liked that episode. I hope you’ve already listened to it before this one because it’s the part one of the email list building episodes I’m doing.

Sam Vander Wielen: [00:04:19] But I feel like just as often as I hear from people like, “Where do I start? How do I build my email list? How do I start from scratch? Or, my email list is kind of dead. It’s not growing.” I often hear from people also like, “What should I send them? I feel like I’m all over the place. I don’t know what to email my people.” And I feel like that’s probably the comment that I get about my emails the most.

Sam Vander Wielen: [00:04:41] I mean, people don’t care about how many people I have on my list. They often are just like, “I love your emails. How do you know what to send? Or how do your emails always speak to me?” or something like this. And I don’t think it’s any secret, I think I just follow a process and so I’ve never really laid it out for everybody. So, I thought that today would be a good time to do that.

Sam Vander Wielen: [00:04:58] I don’t think that people always go into their email list with, like, a strategy in mind. I don’t often find that we focus on strategy enough in our businesses. But I’m a very strategic person when it comes to business.

Sam Vander Wielen: [00:05:11] And the same goes with your email list. Like, nothing I do is random. I’m always thinking about what purpose something has in our business, where it’s leading to, why I’m doing it, what it’s building to. Like, very, very strategic. It’s exhausting actually. But it is the way that my brain works.

Sam Vander Wielen: [00:05:31] And, unfortunately, I think if you don’t enter into your email list with some sort of strategy, it leads to random emails. Or it leads to your email list is just kind of puttering along and sitting there and not generating sales for you. And you either get a bunch of lurkers, which is very common, by the way, with email lists and even with social media. It’s like you’re always going to have more people who are reading your stuff and not responding, and they really love it and they hang on to every word you say, but they just never let you know. And that’s just kind of the way that things work.

Sam Vander Wielen: [00:06:03] But you also are going to lead to more of the lurkers. And we really do want people to be engaged. And you’re also going to lead to more people just sitting there and not, you know, purchasing from you or ever reaching out to work with you or taking the next step. Or exiting if they’re not the right person, which I know it sounds counterintuitive, but we do want them to do that, right?

Sam Vander Wielen: [00:06:24] People also stop and start with their email list a lot. So, I hear from people all the time – maybe you’ve gone through a period – where you’re like, “I emailed every week for X number of weeks or months, but then I stopped.” And we lose people along the way. We don’t become this kind of expected part of somebody’s week or day, and I think that that’s a really important thing. Especially with whatever you’re helping people with whether it’s their business, their relationship, their career, their health, you can become a really vital part. You know, something that people look forward to opening up their inbox.

Sam Vander Wielen: [00:07:00] I feel like I hear from so many people about this email guilt that we have. About like, “I don’t just want to be another email in their inbox. I know people are inundated with emails.” It’s like, “Okay. I get it. And I appreciate the concern.” But first of all, people have agency and they can choose to be there and they can choose to leave. We have to give people that power. And we can’t take over that responsibility for them.

Sam Vander Wielen: [00:07:22] The second thing is that, what if you created an email – we can’t make everybody happy – that, for the most part, people look forward to reading it because it’s really helpful, it’s really valuable. And the email itself should have value.

Sam Vander Wielen: [00:07:37] I think where people get confused is when they think about sales emails or emails you might get from J. Crew or Madewell, where they’re just like, “There’s another t-shirt that’s on sale.” They’re just letting you know. They’re not helping you in any way in your life. Unless they have a really good email content marketing game and they’re telling you like, “Here are ten fall outfits you should try.” That’s out of value, I would open those emails.

Sam Vander Wielen: [00:08:02] But a lot of times what we think of when we think of emails are more of these straight sales emails without content. That’s not what you’re going for unless you’re going through a sales period. And we’re going to talk today about how those ebb and flow and how you balance that, and all that kind of stuff. But your email itself should be valuable. I talked about this a lot in Episode 65. And so, if you’re focusing on value and you’re targeting the right people, they’re going to find it valuable. They’re not going to be mad you’re in their inbox.

Sam Vander Wielen: [00:08:30] If it lands in someone’s inbox who doesn’t find it valuable or they’re like, “This person or this service is not right for me,” they’re going to leave and that’s going to help you because it’s going to help your open rate and it’s going to help your deliverability, and getting people off your list who don’t need to be there. So, that’s all a good thing, so don’t worry about it.

Sam Vander Wielen: [00:08:49] The last thing I want to say before we hop into some more concrete tips – I’m going to give you concrete tips about what to email people today – is that I want to kind of put aside any skepticism over like, “Are email lists dead? Is that the old way of doing it, yada, yada?” I really think that’s a missed opportunity, in my opinion.

Sam Vander Wielen: [00:09:10] As somebody who’s focused on email marketing for six years, it’s been the old work horse in my business. We still make a ton of sales from it. We get a ton of engagement from it. The people who are the most dedicated on social come over and get our emails as well and we really become part of this enveloped network with them.

Sam Vander Wielen: [00:09:28] So, it’s part of the larger picture. It’s part of something more than you can own and really get your hands around versus social media constantly changing. We’re creating content, we don’t know if people are seeing it. I know that when I’m sending an email, 40, 50 percent of people are opening it, they’re seeing it. So, that’s a lot more people than what, for example, Instagram is showing my posts to or my Reels to.

Sam Vander Wielen: [00:09:53] So, it is definitely something to focus on. It is more of the long haul approach. It’s going to be something you have to be dedicated to and have patience with. It’s not going to give you sexy vanity metrics. No one is advertising how many people they have on their email list or comparing to one another. It’s just going to be something you got to put your head down and keep going with. But I swear to you, it’s worth it.

Sam Vander Wielen: [00:10:15] All right. So, let’s get into tips on what to email your list to keep them engaged, keep them buying, creating more of a community. Of course, if you haven’t listened to part one yet, I’m going to tell you to go back and listen to Episode 65 of my podcast because you kind of have to have that foundation in order to hop in to today’s conversation.

Sam Vander Wielen: [00:10:32] But, with that, I want you to generally think about when we think about what we’re emailing our email list, it’s very similar, like you can use what I’m going to teach you today to kind of plan out marketing in general. But I want you to think of it as a 30,000 foot view cyclical thing first. We kind of have to, like, zoom out, zoom up above you and your computer and emailing and sitting on your couch and all that, and we have to think about the larger picture here.

Sam Vander Wielen: [00:11:00] Like, if you thought about the quarter or the year, even half of a year, first we have to think of what are the big bookmarks in your business. Do you know that you’re going to have a group program that opens in January? Do you know that you’re offering a course that’s going to open the doors in May and close the doors and no one will be able to buy it after that? You know, there could be some live event or in-person event that you already know that you have that you’re going to be thinking of.

Sam Vander Wielen: [00:11:28] The way that I always start with this is I kind of plug those big, big things in first and put in place holders for them. Because from there, I think about how, depending on what it is, it could be anywhere from a week, two weeks, to a month before that is going to be a lot of lead up time. There’s going to be some warm up, some teasing, what we call the teaser period. We have, like, the teaser-teaser period, then the teaser period, then the invite period, then the sales period, and then the down sell, and thank you period. So, that can sometimes last well over a month.

Sam Vander Wielen: [00:12:03] So, you kind of have to build that out and look at your calendar overall of where these big things are, how much time leading up to it you’re going to be talking about that thing, and all that kind of stuff.

Sam Vander Wielen: [00:12:14] And because we’re still 30,000 foot view, we’re just talking big picture here, the periods in between that. So, if you saw your calendar is kind of having this big splotches on it for the big events that we just talked about and the lead up that we just talked about, then the times in between there are heavy nurture periods, in my opinion.

Sam Vander Wielen: [00:12:35] So, I think where a lot of people go wrong with their email list is that they see it as a little too black and white. Some people focus on their email list as being all nurture and they never tell anybody about any sales. Or they don’t go through a period where they talk about a service and, like, hyperfocus on it for a while, or they don’t talk about their course or something like that.

Sam Vander Wielen: [00:12:53] And then, we have people on the other hand – I feel like we’ve all been there – you feel like you only ever get emails from that person when they’re selling something. And you’re not really getting value from them, you’re just getting sold all the time. That doesn’t feel good either.

Sam Vander Wielen: [00:13:08] You’ll also run into a problem if you don’t focus on nurturing your email list and the new people as they’re coming in, in between these periods of promotion or sales or opening up the doors, or whatever, in your business. What you’re going to run into is people not being warm enough to buy the next time you do talk about something.

Sam Vander Wielen: [00:13:29] So, that’s just kind of the overall big picture of how I think of this all as like a cycle of kind of what season is this in my business. “Okay. This is the season of nurturing.” I’m building the stocks back up. I’m building the supplies back up because we just put them through this long promo period. And now I want to give them thanks and give them more value and share new resources with them. It’s just like that’s the period that we’re in and we just kind of go up and then we go down, we go up, then we go down.

Sam Vander Wielen: [00:13:58] But these are more soft peaks and valleys. Not super high highs and super low lows. It’s a bit more consistent than that. So, when we’re in nurture periods, for example, I’m still educating people about what I do. I’m still educating people about my products and talking about my products. Telling people what’s going on, what’s going on in the community, maybe some new thing that I’ve added to it, or something that a customer has accomplished or something like that. So, that we’re also building up the awareness. We’re staying top of mind.

Sam Vander Wielen: [00:14:31] And then, that way, when the sale period does come, a couple months from now or something like that, it’s like, “Oh. Right. I know what this product is. She doesn’t have to spend a ton of time educating me as to what is that all about, what’s included, what is she talking about.” It’s all been kind of part of the conversation the last several months.

Sam Vander Wielen: [00:14:51] So, that’s how I like to go about is kind of these soft peaks and valleys. Not super high highs, like sales where you’ve never heard of this thing before but now it’s going to be thrown in your face for weeks. And not super low lows, where we never talk about anything and I don’t mention my products for weeks or months or anything like that. It’ s a little bit more chill and consistent.

Sam Vander Wielen: [00:15:09] The idea here is that in between periods where you’re going to focus on – like I would pick out a couple of times throughout the year where you’re going to intentionally focus on different offers in your business – even if you have one-to-one coaching, even if you have a group program, a course, even if that thing is open all the time, I personally would pencil parts of my year, parts of my quarter in to hyperfocus on and fill those things.

Sam Vander Wielen: [00:15:36] Because just having it open all the time will get a little bit of a consistent drip. But if you really want to capture everyone’s attention, you’re going to have, like, dive deep for a couple of weeks or months on the offer that you have.

Sam Vander Wielen: [00:15:48] And the idea would be that in between those offers, we’d be nurturing the crap out of people. And we’re going to establish like, know, and trust during that time. We’re going to build authority. We’re going to make our email list a soft, cozy, safe place to land so that people, again, enjoy opening up their emails. They get excited. I want you to think about this and visualize somebody receiving your email, seeing your name pop up in their inbox, and they’re excited to open your email.

Sam Vander Wielen: [00:16:17] What does your email sound like? What does it feel like for them to kind of receive this kind of thing? Is it like a conversation with a friend? Is it like a hug? Is it like a high five motivational thing? Is it like you’re sarcastic, dark humored, witty best friend? What does it feel like to them? Are they writing back to you? Is it more conversational? Is it beautiful? Is it like the kind of newsletter where it’s designed and has pictures and cool graphics, and almost designed more like a newspaper where it’s laid out as a newsletter? Or is this plain text, like the kind that you would just send to a friend and they would reply to you?

Sam Vander Wielen: [00:16:58] You really want to spend some time thinking about this, I’ve always felt like my emails were more personal. I’ve talked about this in the last episode that I think because I started out with only having a couple people on my email list who are family and friends, I just pictured kind of writing to them and I was little bit more open and vulnerable with them. And then, I’ve considered it this safe place for me to land as well as creating a safe place for people to write me back.

Sam Vander Wielen: [00:17:27] And people write me back all the time and share different things that are going on in their lives, in their businesses, all kinds of legal stuff that’s happened to them, just all kinds of things. And so, clearly, this intention for me to create that kind of space had the intended effect. It’s worked in that sense. And that’s really what I wanted. I wanted it to be like getting an email from your friend who you had coffee with who just happens to be a lawyer.

Sam Vander Wielen: [00:17:54] And I think the more you can kind of nail that down of what that looks like for you, then your emails can come across as that. And we’re building your authority and we’re building this like, know, and trust factor by you establishing that kind of community curating, essentially, the feel, the delivery of these emails, what they’re like, what their intention is, all that kind of stuff.

Sam Vander Wielen: [00:18:18] By the way, I’m going to give you tips in a couple minutes about, okay, that sounds great about creating cozy emails or emails that are like a high five, but, literally, what do I email them. We’re going to talk about that in a sec so hang with me.

Sam Vander Wielen: [00:18:32] But we can’t just nurture in our businesses. Like, as much as we all – I think you’re probably like me – just want to be helpful and you come from a good place and you have really good intentions. And if you could, you would help everybody. You are a business, and I want to give you permission to be a business, and you don’t need to apologize for that. You don’t need to make up for it. You don’t need to do anything. In fact, you’re a business.

Sam Vander Wielen: [00:18:58] Anytime that you feel guilty emailing about an offer or talking about something that’s going on in your business, I want you to think about Target. I want you to think about Target sitting down and sending emails to people, probably, everyday. I don’t know, I don’t get Target’s emails. But I bet whoever is sending those emails and setting them up, do you think that they feel bad for one second sending out an email about how pajamas are on sale and the air fryer is $20 off. And you can get that oyster blender thing for 9 bucks. And they have albums and books, and blah, blah, blah. Nobody feels bad about it over there.

Sam Vander Wielen: [00:19:38] And you know what else is funny about that? Target is not giving you anything of value other than the product itself. You’re giving the product too. Like, you’re giving either a product or a service or whatever, but whatever you’re doing is valuable. You’re also, because you’re in this kind of business, going above and beyond. And you’re giving people tips, and advice, and recipes, and calendars, and templates, and blah, blah, blah. You’re giving so much that so many other businesses don’t have to give.

Sam Vander Wielen: [00:20:12] As I always say to customers or friends, people walk into Target to get laundry detergent and they “accidentally” end up spending $200 on stuff that we don’t need. I’m only saying this as a theoretical example. I’ve, obviously, never done this. Their pajamas are really soft, guys. If you haven’t tried them, I highly recommend it. But anyway, that is happening everyday all day across the country. And they are not offering them a podcast and a YouTube channel and Instagram Reels and swipeable carousels and saveable posts and tips in Instagram Stories, and emails, and blog posts. Oh, my goodness.

Sam Vander Wielen: [00:20:55] Sometimes I just think about, I’m like, “Gosh. We give so much.” So, if you have any moment where you’re like, “I feel so bad emailing them,” please come back, save this part of the episode. Come back and listen to this if this is at all helpful. But I know, for me, this is the pep talk that I give myself where I’m like, “I cannot feel bad about this. I’m a business. I’m allowed to let people know how they can get something in exchange for payment. I’m not collecting money. I’m not passing around a basket and collecting money. I am giving something in exchange. Plus, I’m giving a ton of free stuff on top of it.” This podcast episode you’re listening to right now doesn’t cost you anything. It costs me a lot to put this on.

Sam Vander Wielen: [00:20:55] So, I want you to continue to work on that. It is a muscle that we have to continue to strengthen even after all these years, after the thousands of people I’ve helped. I can’t even tell you how many thousands of pieces of free content I’ve put out there. When I get a nasty email from somebody who’s angry that I charge for my products, it still stings for a moment. It’s that the stings aren’t as deep. They’re not as harsh. And they don’t last as long. And they don’t have as much of an effect on me anymore but it still bothers me.

Sam Vander Wielen: [00:22:06] And so, this is something that you’re going to continue to work on. And I feel like it comes up a lot when it comes to emails. For some reason, people feel like it’s invasive or something to get in there. It’s really okay. You’re just letting people know about an opportunity. And we can give them the chance to walk away if they want. It’s okay.

Sam Vander Wielen: [00:22:26] So, with that, I wanted to talk about how there are a number of different approaches when it comes to the nurture phase. So, what do you email people when you’re kind of in this nurture phase.

Sam Vander Wielen: [00:22:38] So, one way that you could go about it and that you could at least get yourself into a weekly rhythm or something like that, is that you could pair your weekly email with a bigger piece of content that you’re sending them to. So, your weekly email could be a little intro that then leads them to a blog post, a YouTube video, or a podcast that you’ve done. Or maybe you’ve been on somebody else’s podcast or interviewed with someone else or written an article for someone else. It could be the same.

Sam Vander Wielen: [00:23:09] So, your weekly email could be as simple as that or you could mix that in with some of your regular emails. Oftentimes, I’ll write about something kind of semi-related to what that week’s podcast episode is about or I’ll tell a story. And kind of do a little bit of a set up of here’s why this is important, this is why you should pay attention to something, and that’s why I recorded a podcast episode for you on this and here’s what you’ll learn. So, you can do something like that. And that’s a good way to kind of get in a rhythm with stuff.

Sam Vander Wielen: [00:23:40] I also personally like to send direct education to my email list as well. So, I kind of flip flop. I email twice a week, and one of them is leading to the bigger piece of content and the other email is more like this email itself is the content. And then, I take that and I do things with it elsewhere. But the second email is more like a series.

Sam Vander Wielen: [00:24:03] So, in my end, for example, if you get mine – and if you don’t, you can sign up below in the link below to get my weekly Q&A emails. Every Thursday, I send out a legal – like, if somebody submitted a legal question, I give the answer to everybody, people really like them. And so, every week, you could answer a question that you’ve gotten. They could be client questions. They could be topics that have come up in conversation. Things that you’ve seen on Instagram. They could be anything.

Sam Vander Wielen: [00:24:30] I think the point is making it serious so that it’s regular and consistent. And I think if you could give it some sort of name or something like that, that would be even better. Just to kind of create a little bit more of a community around it. You know what I mean?

Sam Vander Wielen: [00:24:45] If you’re struggling with topics at anytime, then what I want you to do really early on, like starting today, is keep a list wherever you like. I have one in Asana. I also have one in my phone for when I’m just out and about. But you want to start a list where you just write everything on it. Like, it could be really random from, like, a story about a little something that happened to you at the grocery store and you’re like, “I’m not sure what relevancy this has but it’s a funny story,” or it was a scary story, or whatever. It had some sort of impact that you remembered it. Or, it can be like you were DM-ing with somebody and they asked you a really good question, you copy and paste that and you pop that in your list too.

Sam Vander Wielen: [00:25:28] So, I think that this helped me early on because I just gotten the habit of doing this, like, when in doubt, the thing went on my list, what I call the Sizzle File. Somewhere along the way, somebody mentioned this to me, it’s what they called this type of list, and I just stuck with it. But I just got in the habit of saving literally every question, everything I would see in an email, in a DM that would happen on a free call, I would pop it into this list.

Sam Vander Wielen: [00:26:00] To the point where I got thousands and thousands of things on this list and it got so unruly that I started searching the list for common phrases. Or I’d say, “Okay. I want to write about website policies this week because I want to let everyone know that I saw website policy templates.” So, let me search this list for what questions people have submitted on website policies. And I would find those questions and then I would answer them. So, stuff like that, I just think it’s a really good habit to get into.

Sam Vander Wielen: [00:26:28] Nowadays, I have an Ideas file on my Asana board and I just put everything in there when I’m out and about. Usually, when I’m watching movies or watching T.V. shows, the way that my brain works is that everything I see, I convert it into an analogy of how that’s like this in business. So, that’s just how my mind works.

Sam Vander Wielen: [00:26:28] Like, when I was on a cruise in August, for example, I ended writing about this to my email list. I remember I was standing in line watching, they had one of those surf-rider things where people get on this surfboard and then tons of water jets out of them and they pretend surf on the back of the cruise.

Sam Vander Wielen: [00:27:08] And I did not want to do it because I had brain surgery and I’m always freaked out about falling and hitting my head. And so, I just didn’t want to do it. I just wasn’t in the mood. I’m still grieving my dad. I just didn’t want to do it. And normally, I would be very adventurous and do it, but I did not.

Sam Vander Wielen: [00:26:28] So, I sat there and I watched everybody else do it. And it was so funny because, like, one by one, everybody would come up to the window and be like, “Hi. I want to do the surf-rider thing.” And the lady would be like, “Okay. Here are 47 steps of things you have to do first before you’re allowed to go on the surf-rider.” And it was so funny to watch all this people be like, “Oh. No. I just wanted to get on the surf-rider.” And so, they would quit. They would just walk away and they wouldn’t even sign up for it.

Sam Vander Wielen: [00:27:50] Other people would start going through the steps. Like, you had to do little physical fitness thing, and this balance test. And then, you had to go on to baby surf-rider and show that you could lay on your belly, then show that you could get up on your feet. There was just a very long list of things that you had to do before you were actually allowed to go surfing.

Sam Vander Wielen: [00:28:09] And it was so funny to watch how little by little, people just dropped off, dropped off, dropped off. And I was like, this is so like business where everybody wants the outcome. Everybody is like, “Oh, yeah. Sure.” I’m like, “Hello. I’m here to start something with your business.” And then, you’re like, “Oh, okay.” So, in order to do that, it’s going to take years and also a lot of money. And people are going to say really mean things to you.

Sam Vander Wielen: [00:28:34] And you’re going to have to show up even when zero people buy or respond back. And you’re going to have to email your email list every week even when there’s only two people on it. And for a while you’re going to feel like it’s not growing. And you’re also going to have to experiment like starting a podcast and a YouTube channel, and writing a ton of blog posts, and doing everything yourself until you can afford to outsource it enough. And go on and on and on like that. And the more that you, I think, would explain it, the more people would just drop off. Because you’re like, “Oh. I just wanted to do something with your business. I don’t want to do all that stuff.”

Sam Vander Wielen: [00:29:09] So, it was so interesting to me and that’s how my brain works. Like, I just saw the surfing thing and I instantly was like, “This isn’t business.” It’s also analogous, I think, to legally protecting your business because everybody just wants to go surfing but there’s all this foundational stuff that you have to do first and you have to learn the basics before you can hop on the surf board. And everybody wants to go out and build this big business but they don’t, sometimes, want to focus on this foundation, or they want to skip that step and go to the surfing.

Sam Vander Wielen: [00:29:38] That’s how my brain works so I jotted that surf story down. And I just remember people were standing in line, people dropped off, people had to do this physical fitness test. Like, I wrote down all the little details and then I crafted that into a story, and I emailed it to my list. And it turned out to be a really popular email and people responded back a lot and all this kind of stuff.

Sam Vander Wielen: [00:30:00] So, that’s what I’m talking about. It’s like you can be a random story. Or if you’re like me and you have a pretty easy time converting things to how that makes sense for your industry or for what you helped people with, write it all down and it’s all going to be helpful at some point.

Sam Vander Wielen: [00:30:18] Have you ever felt lost about where to begin with the legal side of protecting your online business? Some people say you can just wing it at the beginning and get officially set up later. Not a good idea, by the way. Whether you’re afraid to even start working with clients because you don’t want to do something wrong legally and then get in trouble or your business is growing and you sort of forgot to take care of the legal pieces, I’ve got you.

Sam Vander Wielen: [00:30:41] I don’t want you to live in fear of the internet police coming after you and your business. But you do have to do certain things and get certain things in place in order to legally and safely run your business online. As much as it just feels like an unregulated Wild Wild West online, that is very much not the case.

Sam Vander Wielen: [00:30:57] As an attorney turned entrepreneur and former corporate litigator, I can assure you that there are rules. There are real steps that everybody who runs or starts an online business needs to take. And you’re not behind at all. We can get you set up and following the rules right away. In fact, we can even do it today.

Sam Vander Wielen: [00:31:14] I want to teach you the five very simple steps to take to legally protect and grow your online business. You don’t need an MBA to be a successful entrepreneur and stay out of legal hot water. But you do need to dot your legal i’s and cross your t’s in a few key areas that can’t be skipped. That’s exactly what I’ll teach you in my free one hour legal workshop called Five Steps to Legally Protect and Grow Your Online Business. Just head to mylegalworkshop.com, drop in your email address, pick the time, and I’ll send you a link to watch the workshop video whenever you have time.

Sam Vander Wielen: [00:31:44] This is the best place to begin if you’re just getting started legally legitimizing your business, so head on over to mylegalworkshop.com and sign up to watch Five Steps to Legally Protect and Grow Your Online Business now.

Sam Vander Wielen: [00:31:58] Whatever you decide to email your list, whether it’s the emails themselves are valuable or they’re pointing people to a bigger piece of content, I hope that overall this is part of a larger marketing picture for you where everything leads to something that you do.

Sam Vander Wielen: [00:32:12] And so, we talked about this before in the podcast, why are you creating all this content that’s not about the topic that you helped clients with? Or why would your emails be about something that’s not something you address with your clients or in one of your programs or something like that? You would kind of keep it together.

Sam Vander Wielen: [00:32:29] I mean, you’ll see me like I am right now talking about email lists and helping to build the email list. I will talk about what I call umbrella topics to what my customers are struggling with and what I help them with. I would personally tell you that when you’re starting out, until you’ve really established yourself and your business has become a bit more established, I would really focus on what I call the handle of the umbrella of content, which is what you do and everything that leads to what you do. And working on you becoming more synonymous with your topic and your area.

Sam Vander Wielen: [00:33:03] Once people can be like, “Oh, yeah. Sam the legal girl,” then it helps a little bit to be like, “Well, my customers are also struggling with how to build an email list and what to email them. And I feel like no one is saying this, so I’m going to give them this episode because I just think it’s really helpful.” And it’s part of the brand, I guess, to produce a lot of valuable content.

Sam Vander Wielen: [00:33:25] And so, I didn’t do that so much until I got really established in the legal space. But, also, I’ve already done the content on, for example, how to legally build an email list and what you can and can’t do with your email list legally. So, now this is just like building on that.

Sam Vander Wielen: [00:33:41] But if you haven’t taken care of the core content that speaks to your ideal client about what you do, then I would say you’re not yet at a place to go branching off and talking about lots and lots of different things. I think over time, you can stretch your wings a little bit more.

Sam Vander Wielen: [00:33:57] Whatever it is that you decide to pick and whatever it is that you have or you decide to approach emailing them, consistency is king in my opinion. And so, I’d rather you consistently email your list once a week and get it “wrong” or not have a purpose or not have a strategy or something like this, but get in the habit of showing up in their email inbox, establishing who you are and what you do, what you stand for. And maybe it’s not perfect and it’s not the highest converting email or whatever, but you’re showing up.

Sam Vander Wielen: [00:34:31] And I also love the idea of you practicing writing more. I think this is where investing time and energy into all kinds of businesses into copywriting is just invaluable. I think it’s one of the best things you can do. I think there are courses out there and stuff that you could take, and I think that’s good if that’s what you want to do.

Sam Vander Wielen: [00:34:54] I, personally, didn’t find them super helpful. What I found helpful was practice. I was just, like, writing, writing, writing, writing more, getting more comfortable, finding my voice, writing more like I spoke, ditching a lot of the formalities. I talked about this in Episode 65. But coming from being a corporate lawyer, it was a lot to switch over the way that I wrote and the way that I spoke. So, practicing that more and more and more.

Sam Vander Wielen: [00:35:22] And I think something else that really just takes time and takes practice for people is that, a place that I see a lot of people go wrong with copywriting, both on their emails on social, just in their businesses in general, is that they write too much about themselves without converting it to how that’s helpful or relevant to the person that they’re trying to help.

Sam Vander Wielen: [00:35:44] So, I’ll see a lot of people post stuff on social, for example, that’s just kind of about them. And it just drops off there and doesn’t convert to how is this helpful to your customer or how are you involving them in the conversation. Even if it is something that’s a story about you, how are you making it more of a conversation than a one sided sharing. And I think that’s where a business will really shift from being more of a personal brand, blog, influencer to a business, like, it’s not really about you. It’s about shifting the focus.

Sam Vander Wielen: [00:36:20] And so, whenever we do share something that’s kind of more personal – I know I share it. If you’re on my email list, I share a lot of personal stuff. And I’ve talked about grief and what’s it’s been like to navigate the business growing so much, and all of this. But I always turn that into a relevant tip for you.

Sam Vander Wielen: [00:36:38] And you can literally say this – I mean it’s a copywriting tip actually that I remember years and years ago learning from a copy hacker’s blog post, I think – about how there’s – I forget what it’s called even, but it’s the transition, essentially, in copywriting, where I’ll tell a story about something that happened that’s totally random. It could be about going to the grocery store and finding out that Trader Joe’s is out of Pumpkin Bagels or something like this.

Sam Vander Wielen: [00:37:03] And then, you will literally say what does running out of pumpkin bagels have to do with helping you legally protect your business? Or, like, what do pumpkin bagels got to do with this? You can literally use transitional phrases like that. And then, make the connection for them. Make the connection. Teach them what’s really behind that story. What’s the tip, what’s the lesson that they can take away. How is that relevant to what you do and what you help them with. And so, I find that kind of stuff to be really helpful.

Sam Vander Wielen: [00:37:31] Now, I know that a lot of people will think that sending out an email to their newsletter – or a newsletter to their email list, an easy way to do that is by sharing resources. Like, you can share a list of links and helpful resources. And I think that can be helpful from time to time.

Sam Vander Wielen: [00:37:49] I would caution you though that I think there should be more context and more of your personality. I think you should also take it very seriously that if you’re going to offer resources, they should be things that you really like and trust. It should be stuff that you’ve tried and had success with or an article you’ve actually read. Tell them what’s interesting about it, why they should read it, what they can take away from it.

Sam Vander Wielen: [00:38:12] Personally, though, I would not go towards those kinds of emails. I would focus you’re a business and you want to drive stuff back to your own business, and I would kind of focus on doing a quick educational tip email versus sending out that kind of email, in my opinion.

Sam Vander Wielen: [00:38:31] Another really good tip that someone gave me recently was to set a weekly date for yourself for replies. So, you could set a reminder in your Asana, or whatever else you use, that every Wednesday or Friday you respond back to all the replies that you get from emails.

Sam Vander Wielen: [00:38:48] Now, you might be thinking like, “Hey. Nobody replies to my emails.” Or, “Only one person ever replies.” Then, you set aside that time and you reply back to this person. Because right now, it might be that person. Next week, it might be two people. One day there’ll be 12, then 30, then so many that you can’t reply. We all start somewhere and every person is a full-fledged human being that’s taking the time to read your emails. And everybody deserves the reply benefits, “Thank you so much for reading my emails. Thanks for sharing that with me.” That’s fine, but that’s how we start to build.

Sam Vander Wielen: [00:39:21] And my former marketing manager, Margo, she used to say to me that there’s so many things in business that feel like you’re depositing a nickel into a savings account. And it feels like, “What is the point of this? It’s just a nickel.” And you deposit a nickel everyday, and a nickel the next day, and a nickel the next day. And one day, you look back on it and those nickels, not only have added up, but they also gained you compound interest. And you can’t think of the individual nickels. You really kind of have to think of the larger picture here that you are making these deposits, essentially.

Sam Vander Wielen: [00:39:55] Every person that joins is another deposit. Every person you respond to is another deposit. And these deposits in isolation might feel small. But they’re not small. And they add up. And they are going to gain traction.

Sam Vander Wielen: [00:40:08] Now, in order for you to keep that traction, to keep that thing growing, your emails have to be valuable and they have to give people a reason to stay. So, we have to keep focusing on this value, this nurturing. And it also would be a reason for people to refer.

Sam Vander Wielen: [00:40:24] So, one of the things that I think is a sleeper strategy of a way – it’s something we’re starting to play with now – is to get people to refer other people who they know would also benefit from your emails to join your email list. Because if you think about it, if you run something like Facebook Ads or whatever, you’re paying a lot of money – especially these days, Facebook Ads are a bit more expensive, at least in my experience – then you’re paying a lot of money to get people onto your email list.

Sam Vander Wielen: [00:40:50] If you can have somebody who’s already on your email list and be like, “Hey. My friend, Julie, would love these emails. I’m just going to go ahead and send her, like, Sam has this link at the bottom where you can get people to join, I’m going to send this over.” Then, that is a free referral.

Sam Vander Wielen: [00:41:07] Now, we’re going to start playing with some paid referrals or, at least, reward referrals where people are referring people to our email list. I think that’s kind of a cool strategy. It’s not free though, so I think you could start out by running a little bit of a free campaign. You could give people an extra freebie if they refer people. You could have a secret podcast episode. You could offer a free connection calls if they refer a certain number of people. Like, there all kinds of things you could do, too, that would be free. But I do think referrals could be a part of your strategy as you’re figuring out what to email people and how to keep building this list.

Sam Vander Wielen: [00:41:44] Now, the last thing I want to tell you about is that, when we’re emailing our list, I want you to think about ending everything with one question. A singular question that gets people to respond, that’s super easy to respond to.

Sam Vander Wielen: [00:42:00] So, let’s say that you taught people three tips in your email. You can say, “Hey, Sam. Will you hit reply to this email and let me know, was tip number one, two, or three the most helpful to you. That’s all I want you to do, just hit reply and tell me what number,” something like that. It can be super easy.

Sam Vander Wielen: [00:42:17] First of all, it gets people in the habit of understanding that this is not a one way conversation. It also helps on the kind of strategy side of, like, I think the email gods like it when people open your emails and reply to them. And it’s like last chance to going to spam and all this.

Sam Vander Wielen: [00:42:32] But I also just found that people who started doing those little replies, I then eventually see them writing me longer replies or getting in the habit of replying. And it just kind of builds and builds. Again, nickels, nickels, nickels.

Sam Vander Wielen: [00:42:45] So, little things like this can go a long way. In general, I just want to encourage you to, as I always say, treat them like it’s the olive garden. Once you’re in, you’re family. You’re here on this email list. I’m so appreciative that you’re here. Now, it’s like you’re in my digital home. I’m going to treat you well. I’m going to take care of you. Continue to nurture you. Do my best to show up consistently and become a little part of your week, or whatever.

Sam Vander Wielen: [00:43:10] And I think that that is really what’s led to a lot of, not only email list success for me, but for my business. And what’s most important to me is that it’s made it a place where I can’t wait to write my emails.

Sam Vander Wielen: [00:43:27] I just hired a new marketing manager and copywriter, fulltime employee, who is absolutely wonderful. I can’t wait for her to be here. And I was saying to her, “Just so you know, I write my weekly emails.” I am not letting those go because I really love it. And the reason I love it is because it’s created such a positive community. Not to say I don’t get a nasty email every once in a while, but the point is that people find it really valuable. I think they feel the love. I feel it back. And it’s just something I really look forward to doing.

Sam Vander Wielen: [00:43:57] And in my experience, when you create that kind of a community, it just shows. And it ends up showing in the numbers, frankly. And so, that’s kind of my piece.

Sam Vander Wielen: [00:44:08] I also want to share some resources with you below. Liz Wilcox, who I know a lot of people are in her What to Email your List membership, it’s a $9 a month membership where Liz gives you prompts and outlines of what to email your email list. I know so many people use this and love it, so I wanted to share this with you as a low cost resource for you.

Sam Vander Wielen: [00:44:29] I’ll also link to my Episode 65, Part 1 of this little series for you below. And to get my emails so that you can receive free legal tips and business building advice in your inbox, including my weekly legal Q&A series called Sam’s Sidebar every Thursday, you can use the easy email list sign up link below and join my email list automatically without receiving any marketing emails to join.

Sam Vander Wielen: [00:44:55] So, I love to see you there. I hope that you loved this episode. Do me a favor, DM it a to a friend, text the link to a friend if you think that they would love it too. If you haven’t left a review yet, it would mean so much for me if you would just quickly give us a rating on Spotify or Apple. Leave a review on Apple, you might get a shoutout.

Sam Vander Wielen: [00:45:11] With that, I can’t wait to chat with you next week.

Sam Vander Wielen: [00:45:18] Thanks so much for listening to the On Your Terms podcast. Make sure to follow on Apple Podcasts, Spotify, or wherever you like to listen to podcasts. You can also check out all of our podcast episodes, show notes, links, and more at samvanderwielen.com/podcast.

Sam Vander Wielen: [00:45:33] You can learn more about legally protecting your business and take my free legal workshop, Five Steps to Legally Protect and Grow Your Online Business, at samvanderwielen.com. And to stay connected and follow along, follow me on Instagram, @samvanderwielen, and send me a DM to say hi.




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