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Once upon a time, I hated daily emails.

I thought daily emails were spammy and horrible. You probably do too. Why? Because you’ve experienced horrible, daily emails! Naturally, those are what you think of when you hear “daily emails.”

But if you’re interested in bass fishing, are you going to wake up tomorrow no longer interested in bass fishing? No, of course not. You’re going to look at your subscriptions and watch videos and read magazines and articles about bass fishing.

It’s the same with growing your business or hand lettering. The people interested in hand lettering don’t wake up the next day and look at their Instagram feed and say, “Why am I getting all of these lettering posts in my feed?! Get them out!” That’s preposterous. They’re going to consume because it’s what they’re interested in!

There’s no question that people will consume content in the area of their interest every single day. The true question is whether it’s going to be your content or someone else’s content.

In this episode I’ll tell you how I had people sending me messages begging me not to stop sending daily emails on hand lettering. I’ll also explain why you don’t have to write every day to send daily emails (it will make sense when you listen).

You’ll also learn how to beat me by two years because I foolishly (like you) resisted this idea for years and robbed my audience of a ton of value and also missed out on opportunities for revenue. If you learn this lesson from me, instead of the hard way, you’re going to be so far ahead.

Highlights, Takeaways, Quick Wins
  • People are going to consume content on a given subject every single day. The question is not whether people are going to consume daily, it’s whether it’s going to be your content they consume.
  • Unsubscribes do not matter if you’re getting positive replies from real people to your newsletters.
  • Recency is not king—people do not care whether you wrote this thing last night or last year. Relevancy is king.
  • It’s not about sending the newest content to the greatest number of subscribers in the least amount of time. The most powerful thing about email is sending the most relevant content to a single person at the right time.
  • You’re not emailing 1,000 people; you’re emailing one person 1,000 times.
  • Find the thing that has resonated really well in the content you’ve already put out and put that right up front.
  • Repurpose content that resonated in the past.
  • Always look to your audience for what to write about. What are they struggling with?
  • Create an email course is creating an asset.
  • If you’re putting out one or two pieces of content a week and you have no daily email course, stop everything and make a course that will send daily emails to people who sign up.
  • Tell a cohesive story with your emails (like a tv show) and tie the narrative together. Provide value and insert soft and hard sells every few emails as you go.
  • If you do not already have a product to sell, that is your first priority. Go make a product that solves a problem first. Then come back and create an email course.
Show Notes
  • 06:53 Sean: If you want to do daily emails, maybe you aren’t convinced yet. You will be convinced after this show. You might be thinking right now, “I have to write every day to do daily emails.” You don’t actually have to write every day to do daily emails, and I’m going to tell you why and how. I still think you should write every day, but you don’t have to. Since there is a lot of writing, no matter how you slice it or how often you do it, I do want to promote my upcoming workshop. It’s an online writing workshop at This is going to be a paid workshop that’s going to show you how to write, why you’re not writing, how to get started writing, some prompts, some worksheets, how to take your business to the next level with writing, and supercharge your content writing. This is going to be a super awesome workshop; you definitely want to check it out. That’s going to help you a lot with the concept we’re talking about today when it comes to daily emails.

People Are Interested In Things Every Day

  • 08:09 A lot of people, including myself, hear “daily emails” and think, “That sounds terrible.” The problem is, you think of spammy emails that are sent daily when you think of daily emails. You don’t really think about the valuable things you consume on a daily basis as being spammy, because it’s just invisible to you and you’re enjoying the content. You really only notice something because it stands out for some reason, and bad experiences, like spammy emails that you don’t want every day, stand out. When people are interested in something, they’re passionate about it, they enjoy doing it, and they want to learn about it or get better at it.
  • 09:04 If someone is very interested in bass fishing, most likely this person watches TV shows about it, watches YouTube videos about it, follow Facebook pages about it, and they might even subscribe to emails about it. They certainly have gear about it, they certainly go out and fish regularly with their buddies—they’re all about this. If there was a podcast for bass fishing, they would probably be subscribed. They’re very interested. Cory, give me another example. What’s something someone is interested in?
  • 09:39 Cory: How to grow a business.
  • 09:42 Sean: I like this one. I’m all about this one. I am subscribed to a ton of email newsletters on growing your business. I am subscribed to quite a few podcasts on growing your business. I follow people who talk about growing your business. I subscribe to people on YouTube who talk about growing your business. I am considering going to very premium conferences where people talk about growing your business. I have bought courses that show you how to grow your business. I’m very into this. When I wake up tomorrow, when the bass fisher wakes up tomorrow, he’s going to be interested in bass fishing, just like I’m going to be interested in growing my business. I’m not suddenly going to stop being interested in it.
  • 10:28 With Learn Lettering, my course that teaches people how to make a living as a hand lettering artist, the target audience is people who are interested in hand lettering. They’re not going to wake up tomorrow and suddenly go onto Instagram to the 50 hand letterers that they follow and say, “I don’t want to see any of this.” They’re going to love it. They’re going to double tap some photos and scroll down in their feed because they’re interested. Every day, they’re going to watch some videos. They’re going to go on their Twitter, on Facebook, they’re going to consume this stuff and they’re going to make stuff. This is how people think.

We don’t suddenly become disinterested in things.

We wake up the next day and we consume more content on the thing that we’re interested in.

  • 11:11 My question for you is: is it going to be your content that they consume tomorrow, or is it going to be someone else’s? The question is not whether people are going to consume, it’s what they’re going to consume.
  • 11:26 Ben: That association really does become an issue to overcome. Even as somebody who understands the value of daily emails, knowing that there are people who are focused on providing value, who do that consistently, and who’s emails I would gladly open every single day, I’ve been so conditioned by what I’ve experienced in the past that I still have to overcome that. Even when I sign up for a newsletter that’s not daily, even if it’s weekly, there’s still this nagging feeling in the back of my mind, “Is this really going to be worth my time?” Part of the equation is every experience that people have with you leading up to signing up with their email address.

If you want people to expect value from you, you’ve got to be providing value consistently, even before they sign up for your email list.

Learn Lettering Daily Emails

  • 12:42 Sean: When I was leading up to the launch of the Learn Lettering course, I was doing 30 days of daily emails—an average of 1,500 words a piece (Related: e199 Behind the Scenes of a $177,803 Hand Lettering Course Launch That Made Six Figures in 26 Hours). 30 days of hand lettering emails were going out, and people were eating them up, because these people are interested in hand lettering. I picked a very specific niche, and I delivered consistently on it. These people are interested in that niche, this thing. I’m giving them consistent content, and they were responding to me saying, “I can’t wait to open my inbox in the morning. Please don’t stop doing this.” I was giving them so much value, they were learning so much, and they were soaking it up. They were excited about it.
  • 13:39 The crazy thing was, I even got emails from people who were developers or other random pursuits, like teachers, and they were inspired by these emails. Even though they were super specific and not what these people were even about, it was just value to them, and they were learning a bunch. That was a byproduct; that’s not the reason you do it, but so many good things come of this. It’s incredible. These people are saying, “Sean, don’t stop writing these. I look forward to opening my inbox every day.” Hardly anyone unsubscribed. A year ago, I stopped looking at unsubscribes completely. Best thing I ever did, because the only metric that matters is the replies you get to your emails. That is all that matters. If you get someone replying and saying, “You’re the worst person ever, I hate you, these emails are terrible, they’ve made my life worse,” then you can take that into consideration and say, “Have I been doing something wrong? Have I been emailing people terrible, horrible things and making their day worse, or have I been making their day better?”

Unsubscribes do not matter if you’re getting positive replies from real people to your newsletters.

Those replies are all that matters, and you should stop looking at your unsubscribes.

  • 15:28 An unsubscriber is like someone who pokes their head in a room and realizes, “Oh no, I’m not really interested in what’s going on in here.” You’ve got to think of it that way. It’s the back button the browser, not a big deal. You don’t need to be looking at it at all. I stopped looking at the unsubscribers, and everything grew. Everything was better, because all I was tuned into, all my energy, was focused on the people who were loving the daily emails. Not a single person wrote back and said, “These are terrible.” A few people left the list, maybe. That’s it.
  • 16:15 I don’t know if I’ve mentioned this on a podcast yet, but people look at open rates, too. Forget the open rates. Why? I just realized this. I subscribe to a guy who’s podcast I also listen to. I saw the podcast in my podcast app, and I listened to it. I consumed it. I’m not sure if I finished it. The email came in later that day, and it had the title in the email subject. I was like, “Oh yeah,” and it reminded me of the episode, but I had already heard most of it, so I didn’t need to open the email to tell me what it was about. I clicked “Archive” without even opening it. I saw it and it reminded me, and it was one more brand impression.
  • 17:04 Ben: Sean did consume the content. Just because he didn’t open the email and click one of the links doesn’t mean that he didn’t consume content from that person.
  • 17:17 Sean: I just convinced myself never to clean up my email list again.
  • 17:27 Ben: Charli asks, “Wait, but should I stop looking at my unsubscribes?” I’m going to let Sean take this one.
  • 17:35 Sean: You should stop looking at your unsubscribes.

Shifting Your Mindset: Relevancy Over Recency

  • 17:44 You need to re-think emails. I had this wrong. I was creating so much content that I had a direct correlation between creating content and sending emails. I was only sending emails when I had new content to share. I was convinced that the sharing of the new content was the most important thing. I was convinced that recency was king. Every time I get fired up, it’s because I learned a lesson the hard way, and I want you to avoid it. Recency is not king; people do not care whether you wrote this thing last night or last year. They do not know and they do not care. I struggled with this when I came to podcasts. We used to put podcasts out the next day; I don’t even know how I edited it, wrote the shownotes myself, and put it out the next day. I was convinced that it had to be fresh.
  • 18:47 We did this with seanwes TV. When we first started the show, the first 60 episodes, we got to the point where we had no buffer and we were putting out episodes the next day. It was the worst; it was horrible. We were convinced that we needed to have an active conversation with people. We thought we needed to put out stuff that was made yesterday so people could come and say, “It’s so fresh!” No one cares and no one knows. It’s the same with emails. They don’t care if you wrote it last night. There are a bunch of people listening to it who, kudos to you, started an email newsletter. Kudos to you for sticking to a consistent schedule. That’s awesome. What’s not awesome is writing it Friday night, staying up until 2am the night before to write it. Enough of that.

You need to build up a newsletter queue—you need a buffer.

  • 19:50 I always say four weeks if you can. If you do weekly, do four to eight weeks of content. If you do daily, do two weeks of buffer. We have 14 seanwes TV episodes ready to go. We are that far ahead of what’s actually out, and you have to do this if you’re going to survive. I have to get back to my rant here. People don’t care if you wrote something last night or last year, it’s about relevancy over recency. Right now, you think emails are for sending your new posts to your existing subscribers. This is one thing emails can do. It’s also the weakest thing emails can do. If you want to make money, you have to listen to me. I messed this up. I thought the most important thing about emails was sending the newest content to the greatest number of subscribers in the least amount of time, and I was wrong.

The most important thing about emails is to send the most relevant content to a single person at the right time.

It’s Not About the Numbers

  • 21:15 Once you understand, internalize, and comprehend this, it will change the game for you. We had a question, “Does audience size matter when it comes to whether or not you should do daily emails?” Whether you’re sending an email to 10 people or 10,000 people, it’s always a one-on-one interaction. Don’t talk to an audience. Don’t say, “all you guys,” “all you people,” or, “I’m sure many of you know…” Talk to one person. Write this email to one person. Here’s a tip: open a new compose box, put your friend’s email in the “To” line, and write it to them. That should be your email. You’re not emailing 1,000 people, you’re emailing one person 1,000 times.
  • 22:23 Ben: There has been something nagging at me, and that’s the idea that there are people listening who’s personal preference, regardless of what it is or how valuable it is, is not to get daily emails, particularly long-form emails. If you’re a content creator and you’re trying to reach your audience, the worst thing you can do is impose your personal preferences on how your audience might want to receive your content. I like to think of it as channels. If you establish a weekly or daily video show, that’s a channel through which your audience can receive information. Some people really like video, and that’s where they’re going to consume the most from you. Some people really like audio, so podcasts can be a channel.
  • 23:19 A blog can be a channel. Twitter can be a channel. Your email newsletter, if you do it daily with 1,000 to 1,500 words, that channel is well suited for a particular kind of person. You don’t have to worry about whether all of your audience likes to receive content from you through this channel. The only question you have to answer is, “Is there a portion of my audience that exists that would prefer to consume content from me through this channel?”
  • 23:56 Sean: You’ve nailed it, Ben. There’s people in the chat room saying, “I would never read daily emails. I would never subscribe to daily emails. I’m too busy of a person; it doesn’t matter how valuable it is.” It’s not for you. So many content creators are worried about that person, and that person does not matter when it comes to the decision to do daily emails. I’m not saying that person does not matter, I’m saying that you want to reach them another way. That person is going to watch your weekly video, read every single tweet you do every day, and they’re just saying that they won’t read your email every day. You have to over-index on what works. It’s not about breadth, it’s about depth.

It’s not about reaching every single subscriber, it’s about reaching the top 10% that are the most engaged, because those people are your customers.

  • 24:50 Those are the people that will buy from you. Those are the people you have to think about. The rest don’t matter, everything else is just numbers.
  • 25:00 Ben: You have to think about this, too. Maybe you have a weekly newsletter, and you’re considering flipping the switch and going to a daily email newsletter. It could be any channel; you’re thinking about changing the frequency. When you change the frequency, there are going to be people who no longer want to receive content from you through that channel, but that doesn’t mean that they’re not going to want to receive content from you at all. It just means that they’re going to look for it in a way that is most suited to their personal preference.

It Doesn’t Have to Be Daily Forever

  • 25:33 Sean: There’s a lot of people freaking out right now because they’re thinking, “I can’t create emails every single day.” I want to clarify what I’m talking about here; I’m not actually talking about doing it forever. We are starting to produce a daily video show which is also in written form in shownotes, which is also a daily podcast, seven days a week. That’s insane. We have crazy processes to be able to do this, and that’s not what I’m saying you should do. I’m saying that you should essentially create an email course. When someone signs up for your newsletter, they get five days of emails—or 10, 30, 60, or 90 days. When someone subscribes to your email newsletter, they’ve given up their email address. This is the peak time, the peak of their interest in your thing. They will never be more invested.
  • 26:33 Ben: Let’s address somebody who’s asking the question, “What is so powerful about daily emails? Why is that something I should consider?”
  • 26:44 Sean: At the time when someone subscribes, they’re at peak interest. So many people are not capitalizing on that; that is the time when you should be giving them as much value as possible. Send them an immediate welcome email with more, and then send them an email the next morning, the next day, and the day after that. They’re not feeling daily emails; you’re feeling daily emails. You’re thinking, “This feels like too much.” Tomorrow morning when they wake up, it’s a new day for them. They start over, they reset. They don’t think about you. They’re only thinking about you if they see something from you. Capitalize on that. You don’t have to do this forever. Eventually, maybe you get to the point where you’re producing content daily, but you could spend three months coming up with a 30 day autoresponder.

Repurpose Old Content

  • 27:34 Take the very best content you have and repurpose your old content—replay your best hits. Put it all together in a cohesive format, and imagine that you’re writing a book. Imagine that you’re writing a course. What comes next? String things together in a natural flow. Focus on the transitions between those. We’re going to talk about open loops later. Tell the story and read their minds by answering their questions preemptively. This is advanced level stuff. Start out with a welcome email that tells people who you are, what they can expect, when they can expect it, and then you end with, “What are you struggling with?” Do that for a while, for some months or a year, and you’ll get a ton of questions back. Sort those by the most common. Write an autoresponder that preempts all of those questions.
  • 28:31 You no longer ask them what they’re struggling with, because you know. You start out straight away addressing their questions. You’re answering them right off the bat: “A lot of people tell me they struggle with this, so here’s what I tell them. Here’s a relevant video. Check out this podcast.” Or, write 500 words right there. Give people a quick win right off the bat, and they’re going to love you. When they get a quick win immediately, they think, “Wow, this is going to save me an hour a day, this one little thing that I read from this person.” They’re going to love you.

Find the thing that has resonated really well in the content you’ve already put out, and put that right up front.

  • 29:13 Let everyone else get that immediate win from you every time they sign up. People don’t know about your backlog. They don’t know about all the value in the blog post, going back 26 pages. They’re not going to go back 26 pages. That’s what the email autoresponder is for; it’s delivering to them the very best content over time, strung together in a natural way that flows.

Use Open Loops to Tell Stories

  • 29:44 Open loops are what people use to tell stories, especially in TV shows. You experience this a lot, you just may not know what the name is. It’s where a certain plot line, maybe of a certain character, opens up. The really addictive TV shows have dozens of plot lines; you’re not even thinking about it. Every character has a relationship with another character, and these little things are happening, but they’re not concluded in every episode, so you’re left hanging. That’s why you get to the end of Breaking Bad and you’re on the edge of your seat or you binge House of Cards; it’s because there’s so many open loops. You don’t know what’s happening. The story is opened up and an open loop is created. You start a plot, you start telling the story. For emails, you open the loop and then you close the loop. You always have to deliver on it. You can’t leave people hanging forever, or they’ll get frustrated and quit. I never saw Lost, but I think a lot of people got mad about Lost.
  • 31:01 Ben: That’s the worst. I’m a professional binge-watcher; that’s what I call myself. I notice every time when there’s a thing that they didn’t resolve; it’s like the writers got tired of that plot line and they just kept going. Even if it’s something small and it doesn’t really matter to the story, it leaves you a little bit unsatisfied.
  • 31:33 Sean: You try and bribe a kid, “Hey, clean up your room and you’ll get a chocolate bar.” If they clean up their room and you give them a chocolate bar, they’ll think, “Yeah, alright, every time I clean my room, I’m going to get a chocolate bar.” If you tease a little bit and they say, “Okay, I’m done,” and then you say, “You’ve got to do the hallway, too,” you can only string them along so far. If you say, “Clean up the bathroom with a toothbrush,” they’re going to say, “Forget this!” You can’t string them along indefinitely. You have to have the payoff. The key is the balance between payoff and leaving people on the edge of their seat, excited, wanting more.

You open a loop, but before you close it, you open another loop.

  • 32:30 This can be very subtle, even in a sentence. This is your first email, and you’re answering the most common question people ask you. You’re giving someone a quick win, and you say, “You know what, in addition to this thing, there’s something else that you really need to be aware of. You didn’t even know that you needed to know this, but it’s going to make every difference in your process and save you a ton of time. I’ll talk more about that later. Back to my…” See what I just did there? You want to know, but then you’re distracted by me coming back to the main story, the main plot. In the back of your mind, there’s an open loop created. You’re thinking, “I want this.” You get to the end of the email and you get the payoff on the first loop that was opened, so it feels good; you got the chocolate bar, so you start getting addicted, but you haven’t gotten the payoff on that second loop that was opened. That’s because you don’t close it until the second email.
  • 33:32 The second email comes along, but before you close off the past one, you open a new loop. You start off with a brand new story. I have this friend, his name was Brent, and he was talking about doing freelance work. I tell a little story, we give someone an analogy, we teach someone a lesson, and then, by the way, one of the things that really helped Brent was this little process, this trick. It saved him an hour every single day. I share that; I close the loop from yesterday, and you feel that payoff. I continue on, open another one, close the first one, and on and on and on. You create these open loops to keep people addicted. People only think they won’t read emails every day because they’ve only read bad emails. There’s a reason I have 34,000 people subscribed to Learn Lettering. There’s a reason they were opening the emails every single day. There’s a reason I made $177,000 at the launch of that course; it’s because I got them addicted, I provided value, and I delivered on it consistently. It’s the same reason you watch that same TV show on Netflix every single night.

Scheduling & Automating

  • 35:01 Ben: I’m curious to know about the new subscriptions, the auto-follow up, and that kind of thing. Should you make that a daily touch-point? Let’s say you have a weekly newsletter and that’s what you promise; is it okay, after they sign up, to give them three to five daily emails as an auto thing that happens? Any time someone signs up, they get these five emails before the regular campaign kicks in.
  • 35:38 Sean: You can absolutely do that. That’s probably the most prominent thing I was concerned with when shifting my mindset. I was creating content regularly, I had a newsletter going out every week, I had these podcasts going out, and I was all about the new content and the recency rather than the relevancy. You think you’re doing people a service because you’re creating new content every week and you have this new newsletter that you want people to care about, but you don’t know if they care about it yet. You haven’t tested it or gotten a response from it yet, but you have gotten the response from a bunch of other stuff you’ve made in the past. You know what works well. You know that one blog post that has an extra 2,000 views. People like that for a reason; pay attention to that and give it to people automatically. Stop thinking that recency is king and focus more on relevancy.
  • 36:35 There is kind of an advanced strategy of automating the delivery of emails every day and exempting a certain day. Let’s say your newsletter is on a Sunday; you could say, “Send daily emails Monday through Saturday.” It will stop for everyone on Sunday, no matter when they signed up, so you can insert your blast, campaign, or newsletter. You can do that. That was probably the thing that held me back the most; I was too focused on the new content. It was like the Magic of 700 for me. I heard all these people talking about autoresponders, daily emails, and I thought, “No, but they won’t get the new stuff! I just made this; I want people to care about it.” I didn’t realize that was completely selfish. I wanted them to care about that thing because I made it last night because I didn’t have a buffer.
  • 37:34 I worked really hard and I wanted as many people to see it as possible and to care about it. Instead, I should have been reading their minds and giving them exactly what they wanted even if they didn’t know they wanted it yet, at the right time. I should have been taking content from the last several years and organizing it, writing transitions, and creating open loops between those, creating this email course that may be 30 days or something, that exists like a season of something, an actual story that goes together. If I were to give you a crash course on getting better at growing your business, this is what you need to think about. Here’s what you need to consider first, second, third, fourth, fifth, how this ties together, how to get to the next level, how to branch out, and how to systematize.

Think about what you’re sending out for people instead of throwing out random bits of content.

  • 38:26 Admittedly, I still do that. I still am sending out new pieces of content: “Hey, we’re talking about hiring today. We’re talking about unsolicited advice. We’re talking about getting the most out of conferences as an introvert. Next episode, we’re going to be talking about Imposter Syndrome.” Yes, this stuff helps people, but that order of things is less than ideal. I’ve been saying, Sign up for the newsletter, there’s this big thing coming.” It’s this epic email course that you get when you sign up. I’m going to be treating the course like I’m writing a book. It’s going to all go together, make sense, and hold your hand along the way. It’s going to be something you actually want to open every day.
  • 39:27 Ben: It’s a daily email course that will help you get better at, provide more value, and feel more comfortable with doing daily emails.
  • 39:41 Sean: I should do that, Ben. This is where it gets awesome, because once you get into this mind space and you understand this, you can replicate it. You go to and sign up, and you get several emails and several videos about value-based pricing. You have all these different entrance paths, so eventually it’s going to be that when you sign up at, you get this. When you sign up at, you get that. It’s all very tailored. It’s going to feel like I’m reading people’s minds, because the place they sign up is going to be at the end of this landing page that says, “Hey, you want to get better at writing. You want to find out what you should be writing about. You want to grow your business with writing.” They get to the bottom of that and they’re thinking, “Yeah, yeah, yeah.” If they sign up, I know they’ve said yes to all of these things.
  • 40:34 I send them that content. They’re going to love it. You have all these different channels and paths. You spend your time creating these email courses, these paths, for each individual sign up. People are going to love that. People go down these different email course paths and then, eventually, come to a single bucket where the weekly or semi-weekly blasts go out to. If I come out with something new, everyone who’s gone through these courses will get the new stuff. They’ve already gotten tons of value. By that point, those people will be as addicted and invested in the seanwes brand as the people who have already listened to 211 podcasts.

Why Should You Reuse Content?

  • 41:26 Ben: I recently heard a concern from a client, partially about the recency thing, but partially because they felt like what they were providing to their email subscribers was exclusive. He said, “I want it to be exclusive. I don’t want to send them something that I have somewhere else or that’s going to show up a few days later. Then, what’s the point of signing up for somebody’s newsletter?” One of the pieces of value they’re getting is not just exclusivity of content, but it’s the fact that you’re delivering something directly to them that you’ve hand-picked, curated, and put together for them. That’s the way you need to think about it.

It’s not necessarily the exclusivity or the recency of content that’s valuable to people, it’s the relevancy and the fact that you’re putting it together with them in mind.

  • 42:33 They don’t have to go to your website, search through things, go through Google, or try to look through your social media feed to find the information they’re looking for. You’re sending them something that’s answering their questions, meeting their needs, and providing value for them right there in their inbox. That in itself is very valuable, and that’s really the reason people sign up—not so that they can get exclusive content, but so that they can get content delivered directly to them that is valuable.
  • 43:33 Emily Carlton asks, “Should you always look over older content before re-sending or repurposing to see if your views have changed or if you have an add-on?”
  • 43:49 Cory: I think you should look back before deciding to repurpose. Your views will change as you go on. That’s true especially if you’ve been doing it for several years. Your views are going to change on how you feel like you can provide value, so I think it’s good to look at it. Even if you think, “I think totally differently; I shouldn’t even look back.” You’re going to find some stuff that you thought several years ago that is still good, and you might change it up a little bit.
  • 44:22 Ben: There’s an underlying principle that repurposing content is not about copying and pasting; it’s about having a piece of content that lives in a specific channel and is formatted for that, so if you’re going to repurpose that for another channel, you have to format it for that channel necessarily, and as you’re doing that, you’re going to go over that content again. It’s not like you’re saying, “I like the title of this one; I’m going to copy and paste the text without thinking about it.” You really do want to be thoughtful about how you’re formatting it to fit that channel. You might even need to add three or five paragraphs to make it fit with the style of everything else that goes out in that channel. As you’re doing that, you’ve learned new things, so repurposing the content might look like taking that title or that topic and re-writing it based on your new understanding but using some of the outline of what you communicated before.

Repurpose content that resonated in the past, not just something that sounds good, but something that your audience needs, wants, and is looking for.

  • 45:44 Hopefully, as you’re looking for feedback, people are asking questions, and the way repurposing content is the most powerful is when you know that you put something out that answered this question before.

Get Help Sending Daily Emails Now

  • 46:18 Sean: I want to help people with this, but I know there’s a lot more struggles that we can’t quite get to. There’s a lot of mental hurdles to overcome. It took me years to get to the point where I understood this so I could unlock it, and I’m only just now starting to see the benefits of unlocking it for my business. I want to help people get there, because when I got into this, I heard all these people talking about daily emails and autoresponders, and they were talking about it as if they were already on the other side of that hump, that fence. They got it, but I didn’t get it yet. I didn’t know how to get to that point, and it was really awkward and hard. I want to help people smooth out that transition, help you get from wondering how you could possibly do it, why, and feeling like it’s maybe not a good fit, to actually being able to do it and seeing the results.
  • 47:17 You can go to, and I am going to help you get to this point. I’m going to do exactly what I’ve been preaching on this podcast. The people that sign up there are going to get a course. I’m going to send you daily emails, and we’re going to get people who sign up for that. As much as you say you don’t like daily emails, guess what? The people that got this far into the podcast want to learn how to do this. I’m getting super meta here. They’re going to sign up voluntarily to get daily emails from me on this thing that they’re interested in. I guarantee it.
  • 48:18 I’m going to write a specific course just for them, to help them and to provide value. Obviously, we’re going to get a lot of existing subscribers there, but there are going to be new people who have not signed up for any of my lists. They’re going to go to, they’re going to get this course, and eventually, they’re going to go into the main bucket where they get more value from the new things that I put out. This is what you do:

Create these paths, read people’s minds, and speak to their struggles.

  • 49:03 Emily asks, “If you begin daily emails, should the content reference previous content or build on itself? I wonder if people should miss a day and then be confused.” What do you do when you see this sentence: “In the last email, we talked about…” if you haven’t read the last email, you missed it, and you’re very interested in the topic? What do you do when you see that sentence? What do you do when you see a video you’re really interested in and they say, “In yesterday’s video, we talked about such-and-such,” something relevant to you, what do you do? You go back.
  • 50:01 Ben: There’s this other thing that happens. When you’re watching shows and you accidentally skip ahead to the next episode, and they do the little recap at the beginning, I turn it off as fast as I can because I don’t want spoilers. I check, and I see that there was no progress on the previous episode, so I need to watch that one first.
  • 50:23 Sean: “Oh no, what if the person picks up my book and jumps right to page 88 and things are happening?” They’ll probably figure it out and go back, if they’re smart. If someone skips one of your emails, they open the latest one, they missed it, and you referenced the past one, they’re going to go back to it. Yes, absolutely, you do want to string these together.

Answer the Questions People Are Asking

  • 51:18 Brandon asks, “Any suggestions on how to generate valuable content on a daily basis? Other than the time tested Early Wake Daily Write. I’m struggling with generating ideas to write about.” If you’re creating new content every day, it’s okay for that content not to always be incredible content. I’m not actually saying that you need to write this daily autoresponder every single day and have every new day be a new day in the autoresponder. It could take you a lot of time, it could take referencing past material and putting it all together. Writing daily is great, but you don’t have to take every day’s writing and say, “This has to be the email that goes in the sequence next.” It does take some time to come up with really good stuff.
  • 52:05 He’s saying, “I’m having a hard time generating ideas to write about.” You should never be generating ideas. Don’t ever just conjure ideas or say, “What do I want to write about today?” Always look to your audience for what to write about. Go watch seanwes TV or episode 99 of the podcast—it’s about finding what people are struggling with and getting those questions people have. How do I start writing daily emails? Dive in a little bit deeper. I already have an existing weekly newsletter; how do I incorporate daily emails into my process, workflow, and output? Now, some people’s ears just perked up. The kind of thing I’m going to be writing in the daily email course is a little bit more focused. I don’t mind plugging my own stuff.
  • 53:11 I also know that someone out there is going, “I don’t have an audience. What do you have to say to that, Sean? Nobody’s asking me questions.” No, you’re not off the hook. You look to the forerunners in your industry, go to their Twitter, look at their mentions, find the questions people are asking them that they’re not responding to because they’re too busy. Boom. You go to the forums and find the questions and the struggles people are writing about, and that’s what you write about. Find the discussion.

Where are the people you’re trying to reach hanging out?

Listen to them.

  • 53:52 Talk to them. Observe their questions. That’s what you write about. Don’t ever generate ideas. That’s the slow way to go about this, and I don’t like the slow way.
  • 54:07 Ben: You’re guessing, and you’re throwing stuff out there and hoping something sticks. When you are answering real questions, it’s amazing how powerful that is in building and growing and audience.
  • 54:21 Sean: Maybe I should stop doing a daily video show. There’s too many people who don’t have time to watch five minutes of a video every day. If it’s daytime, there’s a new seanwes TV. It’s as simple as that. Why do people get excited about that? I started getting tweets, YouTube comments, and people in the chat saying, “It’s daytime, there’s a new seanwes TV!” They’re excited because they get value out of it. That’s who we’re doing it for. For the people who don’t have time, that’s why we have highlights, shownotes, podcasts, and why we’re going to be doing a weekly digest.
  • 55:26 Cory Miller and I are working on that. Every week, we’re going to send out a digest of the past seven days’ worth of seanwes TV. Bobby says, “Sean has it so you can get value no matter how you consume information, eliminating all excuses.” That’s what we’re trying to do. If you’re just starting out, you shouldn’t not do daily emails because some people don’t want it, you should do it for the people who do. Eventually, think about what those other people do want, and also do that. On a recent AskGaryVee episode, someone asked, “Should I be focusing on quality of content or quantity of content?” What do you think his answer was? Both! Work harder! Do both. It’s about both.
  • 56:47 Ben: I’m thinking about the person who is thinking, “But look at all the time Sean has. He’s doing all these things and he has all this support.” You have to stop looking at the people you follow and being envious of their output. Measure yourself against yourself. What are you doing right now? If you feel like that’s not enough, what are you doing about that? How is next week going to be different? How is next month going to be different in your output?

Email vs. Other Daily Content Streams

  • 57:52 Sean: Matt says, “What are the benefits of moving to daily emails as opposed to increasing the frequency of other content streams (blog, podcast, etc.)?” They’re not mutually exclusive. It’s the Gary Vee answer—both. I don’t necessarily just mean work harder, I mean that once you create an email course, it’s an asset. It’s just there. Every time someone signs up, it’s not a random piece of new content. “I signed up; why am I getting part three?” That is someone’s experience when you don’t have an autoresponder. This time, they get something that’s perfectly tailored to them and their interests based on the page they signed up on. Gary’s answer of “both” really does apply here, because you spend the time once of creating an email course, and then it just serves you and serves the person over and over and over. You’re freed up. You don’t have to make those every day. Now, you go focus on also doing a blogpost or a podcast.

Daily emails are not meant to be the thing that fulfills your daily exposure to all of your audience.

  • 58:54 Ben: It is meant to fulfill a specific purpose for the type of person who would subscribe to an email newsletter and want daily emails from you. If you just do that, it doesn’t mean that you’re reaching the rest of your audience who wants content from you in different ways. You can’t think about it as whether you should do this or that, what’s more effective. Maybe you are absolutely having to decide between doing a daily email responder vs. some other form of delivering content. The people who subscribe to my email list are giving me access to their space to provide value, and that can be a very powerful tool for converting and selling down the road, more powerful than some other forms. Maybe the follow up question to that is, if you had to choose, is it more worthwhile doing daily emails than starting up a daily video show or something like that?
  • 1:01:01 Sean: To someone who’s torn right now, if I could back in time, I would have created this asset. I would have made an autoresponder, because here’s the beautiful thing. Once you have this email course that reaches a specific audience and answers all of their questions, you can then work toward doing other things daily. Even if you’re not able to do weekly or daily, anything you put out will point people to that course, however often it is. Maybe you only do once a month; it’s not going to be that effective, but once people get in, then they’re seeing you daily. You’re top of mind every day for those people who come in. If you’re trying to decide, stop everything and make a course that will send daily emails to people. Then, everything else you do will point people to that, and that’s all automated.

When Should You Start Doing Daily Emails?

  • 1:02:18 This is a question I will end up answering in that course that I just made up on the fly during this episode at I am going to end up answering this in even greater depth, but when do I want to start doing daily emails? The answer is, when you have something to sell. Now we just set a bunch more people back, because now your priority is creating something to sell. If you’re at this point, you need to not be worrying about automating, but you need to be worrying about creating something that solves people’s problems. If you’ve been having conversations with people, doing your research, and creating other types of content that has resonated with people, you know what they need. You know what they’re struggling with. If you make a course, workshop, a product, an app, a SAS app, whatever it is, then you can use the daily email autoresponder as a method of selling it.
  • 1:03:29 This is where we enter a whole new level at one hour into the podcast. This is where your daily email course becomes like that daily TV show you’re watching—but it’s the adds in-between. I’m not just talking about the commercials, but maybe there’s a coke can in one of the episodes facing the camera with the logo. Sneaky. You mix it up with soft sells and hard sells, but it’s all mixed in with the value. You’re still watching a TV show, even though there’s a coke can or a Swiffer add in-between. You promote your paid thing for the people who want to go to the next level.
  • 1:04:17 We’ve already leveled up. There are people listening to this podcast who can’t be bothered to pull over the car and go to on their phone and sign up to get more value, but I don’t care. It’s not for them. It’s for the 2% of people who will do this. For those people, I’m going to give them a ton of value, but I’m also going to sell some higher, related thing, a paid thing that will be even more personalized. Maybe it will have live group coaching calls or individualized consultations, something even deeper. You have this daily email course, you write this out. This is your TV show, essentially. Then, periodically, every three or seven emails, push your product. I’m not saying to be pushy about it, but you make people very aware: “By the way, if you’re interested in this type of thing, my product will take you from A to Z on this. By the end, you will have an email course with all of the sells at just the right optimal points to where it will convert to optimal revenue for you.”
  • 1:05:33 They think, “Wow, that’s pretty awesome. I could keep getting these free daily emails, but if I sign up for this course that has templates, worksheets, and everything formulaically laid out for me, that’s going to really help. That’s going to save me a ton of time.” You make people aware of that, and that’s a soft sell. In the middle of a value-filled email, you say, “Hey, check this out.” You do a few more emails, and then you can do a hard sell. This is your commercial break. This is, “Hey, I’ve been sending you 10 days so far on how to do this thing. I also have this paid course. If you want to go deeper, go check it out and buy it. It’s x dollars.” Unapologetic about it. If you sign up at the website, this is what you’re going to get. This is what I’m going to make. You’re going to see me do it; I don’t even care if you buy it from me.

Insert soft sells and hard sells into your daily emails.

  • 1:06:33 This is all I can do in a podcast, so if this is interesting to you, go sign up, because I’m going to show you more. There’s an open loop for you.
  • 1:07:05 Ben: I love the idea of how all of this stuff works. You set it up, and then it isn’t that you’ve started this campaign and you have to show up every single day for 30 days or whatever it is. It’s something you put together beforehand and, like Sean said, it becomes an asset for you. I love that. Because you’ve already spent all the time putting this together, you get to spend your free time where you’re not working on this thing fielding the questions and comments that come in and engaging with people. The engagement you have with people throughout the campaign can be value that’s used for the product you’re going to ultimately sell.
  • 1:08:02 Sean: That’s totally true. We’re planning on doing that with the Value-Based Pricing course. We’ve got a webinar that we’re going to give to people that’s going to be live at We’re also opening up a beta at the end of that webinar for people who want to get into that course early and have more direct access to myself and Justin teaching this course. We’re going to go through this with people. There’s going to be an application process where they have to say, “I’m ready to apply this, I’m going to apply this, and I’ll report back with the results.” They’re going to be very engaged; we want serious people, but as a result, we’re also going to turn them into case studies. In the future launch of the course, they get to be someone that we highlight as an actual real life example of how to do this in a real business.


  • 1:08:52 We’re doing just that, taking those real examples with people and putting it as extra value into the paid thing. For me, I’ll be honest, we don’t have things optimal just yet. We’re not where we want to be yet. I really want to have more products available. I have so many things in mind, but admittedly, I haven’t focused down enough to ship more things. Once we have Value Based Pricing, once I’ve done the Super Charge Your Writing Workshop, in the future, I can afford to teach more about writing, because I can give things away and say, “By the way, if you want to actually make money in your business by writing, go to You can purchase the workshop replay.” Boom. I can afford to do that. I can afford to do these podcasts because I can say, “Hey, you want to access other people who are really smart, like-minded, and get personalized feedback on your projects? You’re starting to do daily emails and you want to see what people think about it? Join the Community at”
  • 1:09:56 This whole podcast has so many pitches in it, but it’s all promising more relevant value after I’ve provided a ton of value, and that’s why you’re not done listening to this podcast. That’s why you’re going to tune in the next episode; because it’s just value and I’m being transparent saying, “This is exactly how I do it and I’m just showing you as I do it.”
  • 1:10:21 Ben: When you’re writing this content and you’re trying to come up with a product, or you’re wanting to put together an email course, you have to be answering real questions. You’ve got to be providing real value, and the way you do that is by sourcing your audience for real questions, real struggles, real things that they’re going through. One of the things that makes this episode, or any podcast episode that we do, more valuable, is when we dive into real questions. Fortunately, we’ve got the chat and the audience that’s here. There are people subscribed to your email newsletter who, when you send something out, reply and ask for clarification or ask other questions. Even if you don’t have any of that, even if you don’t have an audience yet, in your industry, there exists an audience for whatever product, service, or idea that you’re trying to create content around.

If you don’t have an audience yet, you’ve got to go where the people are, find out what their real questions are, and answer them.