How to Make a Newsletter Your Career's Secret Weapon

I'm Nicole Lappin, the only financial expert you don't need a dictionary to understand. It's time for some Money Rehab.
Hi, it's Morgan, the executive producer of Money Rehab, and today's episode is all about making a newsletter that helps you further your career and business goals. But first, I want to tell you what we're doing next week.
Next week, the guest hosts of Money Rehab will be Mosh Manunu and Jill Wagner. Mosh and Jill co-host a daily news podcast called Mo News, which is my favorite daily news podcast.
I swapped the daily out for Mo News a long time ago. Sorry, Michael Barbaro.
it's just the truth. Next week in the Money Rehab feed, you'll be hearing the week of Mo News episodes, and it's going to be a really jam-packed week for news because of the inauguration, so you're definitely going to want to tune in.
But back to newsletters. Today, I'm going to be giving you a deep dive on the step-by-step process of creating a newsletter, or if you already have one, making it better.
There's a few reasons you'll find this useful. First, if you've been thinking about starting a newsletter, or if you have one and want to get more people to read it, well then obviously this is going to be helpful.
But if you don't have a newsletter and it's not on your bingo card for 2025, you might want to consider it anyway. If you run a business or if you have a side hustle or if you're interested in dipping your toes into the creator economy, a newsletter is a really good way to connect with your customers or community.
If you're wondering why, look no further than TikTok. At the time I'm recording this, it's looking like TikTok is probably going to be banned in the US.
If you had hitched your business wagon to TikTok star, you're going to lose the community you built there. Some TikTok creators are scrambling now, trying to get their audience to follow them on other platforms, but this is just the inherent issue with being dependent on a platform that you don't control.
The algorithm could change and all of a sudden your posts are shadow banned or the app could go away entirely and then you lose that base. But newsletters are different.
In business speak, the difference is that with a newsletter you quote own your customer. That sounds weird, but the big point there is that you are in control of your relationship with the customer because you have a way to reach them that is independent of the platform and that's just because you have their email addresses.
Yeah, you could be on a newsletter platform that goes the way of TikTok, but you would still be able to quote, keep those customers because you can just export the email list and then write to them on another newsletter platform. So that's the business use case for newsletters.
There's also, of course, the creative use case. If it makes you happy to write things and put them out in the world, that's cool too.
And that's sort of the bucket I fall into. Kind of.
I've been really interested in the idea of starting a newsletter for reasons I'm going to explain a little bit later, but for now, all you need to know is that I have wanted to start a newsletter for over two years now, and I haven't. Because I have a lot of

questions and there's a lot that I don't know. And when I say a lot, I mean I don't know anything.
I have both left brain and right brain questions on this. I want to know what makes newsletter creative stand out, and I want to know what technical best practices I need to know so that my stuff just doesn't end up in spam folder limbo forever.
So today I'm talking to two experts. First, you're going to hear advice from Jason Pfeiffer, editor-in-chief of Entrepreneur Magazine, the host of MNN's career and business podcast, Help Wanted, and author of the newsletter, One Thing Better.
I went to Jason for advice because I always go to him for advice and also because his newsletter is one of my favorites that I subscribe to and definitely one of the only ones that I actually read every week. I saved all of my questions on creative for Jason.
We talked about what makes a good newsletter, what he learned through going through three iterations of his current newsletter, and I asked him for feedback on my idea. So then you'll hear more about what I'm trying to do with this thing.
Then you're going to hear advice from Alyssa Doolin, who manages the growth team at Kit, formerly known as ConvertKit. Kit is a newsletter platform that I decided to go with because Jason does his newsletter there and I will just do whatever he does.
And so that leads me pretty perfectly into sharing the advice that I got from him on making a good newsletter. Can you describe your newsletter in one sentence? I can because I've spent a lot of time thinking about it.
each week the editor editor-in-chief of Entrepreneur Magazine, which is me, gives you one way to be more successful and satisfied and build a career or company that you love. That's so good.
How did you get there? Because when I first subscribed to your newsletter, it was called something different, actually. Yeah.
So my newsletter has gone through three phases. And then I have spent a lot of time iterating inside of each of those phases.
So let me give you the quick rundown. The newsletter began as the Pfeiffer Five, which is a terrible name.
That's before my time. Yes, that is before your time.
That was a terrible name. And the idea was simply that each month, I would send out five things that I found useful.
And it was called the Pfeiffer Five, because my last name is Pfeiffer, and there were five things. Terrible, absolutely terrible.
Because it didn't communicate anything about anything. It set absolutely no expectations for why you should sign up for this thing.
And then the cadence at monthly, you forgot that you even subscribed to it by the time the next one showed up.

Then it became Build for Tomorrow, which was the name of my book. And I thought would also be the name of my newsletter.
And the book is about change. And so I thought I would make the newsletter about change, how to navigate change, how to thrive in times of change.
but I found that to be too abstract,

too difficult to write to.

And also, you is like a thing people deal with, but it isn't a thing that people wake up in the morning saying, I need to read about. So then I rebranded it as One Thing Better, which is what it is now.
And my thinking behind it was, people get too many newsletters, and they get too much information inside of those newsletters. It is a deluge inside of a deluge.
And I know that if you give people 10 things to do, they'll do zero of them. And so instead, why don't I orient this newsletter around a promise? And that promise is that every time you read this, it will be simple.
It will be straightforward. It will be one thing that you can do.
Feels very manageable. I was dealing with the problem of I speak to a broad audience.
I think that newsletters actually have an advantage if they speak to a very specific audience. I speak to a broad audience.
So that was my way of approaching it. And then how did I get to that line each week? One way to be more successful and satisfied and build a career company you love.
Honestly, the answer was that I kept changing the words in it in response to things that people would be most responsive to in the newsletter. I eventually found that people like the idea of success.
Newsletters that were in some way or another about finding satisfaction, finding happiness, finding calm seem to really resonate. I still always have the impulse to change this language.
But I think the best thing that you can do is put something out in the world, see how people people respond to it try to identify the language that they use to describe why you are valuable to them and start using that language back to them that is so helpful and you know the reason the reason why I ask is because I know you've gone through these different iterations and my hope is that I can sort of use you as a little bit of a cheat code so that I have to go through fewer iterations myself. That's the goal.
That's the goal. But realistically, I know that I will have to respond in real time to feedback and things like that.
But I'm curious why you knew or how you knew that you needed to make these changes in the first place. Like I hear you say that people don't wake up in the morning thinking, I want to learn about change.
And so that's sort of where the build for tomorrow transition came from. But were you getting that feedback or were you seeing something that made you feel like it wasn't working and then thought that you needed to

change something? Okay. So my answer is pretty hyper-specific to me, but I think inside of this answer is something that's really useful to everybody.
So let me just tell you what it was. The Build for Tomorrow version of this newsletter, so that was the second iteration of the newsletter, coincided with me getting this incredibly sweet deal from Facebook, which I dragged Nicole into as well.
So Nicole got this sweet deal from Facebook too. So the sweet deal from Facebook was that they were launching a competitor to Substack.
For those who don't know, Substack is the leading free newsletter tool that you're supposed to monetize with subscriptions. So in other words, like you don't have to pay to use Substack.
You do have to pay to use some other tools like Kit or Beehive. These things have a, there's a cost associated with using the product.
Substack is totally free to use. They hope that you will create like a paid version of your newsletter and then they'll take a cut.
And they had been, to launch, Substack had been paying creators to use the product. So like they would find some, you know, some popular blogger or something and they'd be like, hey, we will pay you $200,000 a year to put your newsletter on Substack.
So when Facebook was creating a competitor to Substack, which was called Bulletin, they started calling people like me and basically making that same offer. They were like, we will pay you gobs of money to just use this product.
And that was pretty good. They were offering a lot of money.
So I said, yes. And then I said, oh, you should talk to my friend, Nicole.
I bet she would like your money too. And so that's how that happened.
So I took this deal and I rebranded my newsletter as built for tomorrow. And I started getting paid by Facebook.
And a couple of really interesting things happened. Number one was the way to grow on Facebook at that time was to write a newsletter that could be promoted inside of Facebook news, which barely exists anymore if it does at all.
But back then was, you know, like Facebook's attempt at being a kind of something of a news aggregator. And so they would surface your newsletters inside Facebook News.
So that created this incentive to write newsletters that would show up in Facebook News, which were very different from the kinds of newsletters that were really good to readers as they showed up in inboxes, right? Like I had a different audience in mind. I was writing differently.
And so my newsletter would grow only when it showed up in Facebook news. And when Facebook eventually killed that product and I was like out in the cold, you know, with like nothing but my money jacket from Mark Zuckerberg.
You know, I started to think like, what works about this newsletter? And I realized that the only time in which I got any feedback or I heard from audiences or I saw any growth in this newsletter was when it showed up in Facebook news. Otherwise, nothing was happening.
And the reason I tell you the story, the reason I think this is relevant to you, even

if you don't get a bunch of Zuck Bucks, is because you have to have the right incentives in order to build something for your audience. So you need to be out there in the cold.
You need to be able to see and feel what people respond to and what they don't respond to. You need to live or die by whether or not people really genuinely like and care about and want to read and share the thing that you make.
And if you are not seeing that, no amount of paid growth or partnerships or whatever can get you to escape the death spiral that that will be. So I really liked actually getting kicked out of this Facebook thing and having to figure it out on my own.
And what I realized was I was not being something that people were excited about. And the newsletter was not growing organically by itself.
And I stepped back and I thought about why. And I thought, if I subscribed to this newsletter, I would not know what in the hell it was.
Just like day in, day out, this newsletter shows up. I don't know what this is.
I don't know why I'm getting it. I believe, Morgan, we do a good job of this on the podcast that we make, but I don't know how explicitly we ever think about this.
Here's a formula for media that you inherently know, but that you need to apply to your newsletter and that everyone should apply to everything that they make. the formula for media that you inherently know, but that you need to apply to your newsletter and

that everyone should apply to everything that they make. The formula for media, whether you are just

thinking about this for your own Instagram channel or a newsletter that you make or anything,

the formula for media is the right combination of predictability and surprise. That's it.

So predictability, it has to reliably deliver upon something that people want and they know

how it adds value to their lives. Surprise, they don't know what you're going to say next.
If you get that balance wrong, if you are too predictable and therefore too boring, or if you're too surprising and it's just like every week a newsletter shows up and it's like, what is this? Why are you writing about that now? That's bad. People will tune out.
I needed to figure out what can I do that really lives in that. I need to establish a promise.
I need to pay off on that promise reliably, but I need to do it differently and surprisingly each time. That is what took me away from the old formula and forced me to come up with something that would actually resonate.
Yeah, that makes so much sense as a reader of your newsletter as well. And something that I really like as a reader of yours is that the predictability isn't just in the promise of the newsletter, but it's also in the format.
And so I wanted to talk to you about that, too. in addition to, again, just the reader having that element of predictability, they know that they are going to be reading about one change that they can make

that will benefit their career or business in some way. But you also use the same sort of formula week over week to tee up the newsletter.
You describe a problem that people are most definitely having, and then you tease the solution with a hook that tells people what they can expect to learn in that day's newsletter if they keep reading. And it might be easier to just give an example.
I'd love to hear it in your voice. Just the one maybe from yesterday's newsletter, The Secret to Loving Without Regrets.
That's exactly what I had in front of me. This is why we work well together.
Okay. Yeah.
So that's exactly correct. Let me just read this to you.
And for context, my newsletter, for those who haven't read it, my newsletter is about a thousand words, and it's usually broken up into three or four sections. Sections are just, you know, it's like a big header that makes it a little easier for you to feel like you know where you are in the newsletter.
And so this is the beginning.

This is what I think of as the opener for a newsletter that I just published. The headline

was how to prevent miscommunications. And here's how it starts.
You're being misunderstood. You

shared a great idea or made something wonderful or told someone something and they are confused,

unimpressed, maybe even annoyed. Now you're upset.
Why don't they just understand? But here's the problem. You started in the wrong place.
I fall victim to this all the time, including here in this newsletter. So today, I'll share some of my own stumbles and a powerful two-step exercise that will make your intentions and ideas clearer so everyone understands you.
So that's the opening. And then it goes on.
The thing that you see underneath that is the first header for the first section. And the header says, first, my own mistakes.
And then I tell a little story about how I screwed up. So, okay.
Now we've established that. Questions? Yes, questions.
So can you talk about the choice to have that repeating format? Because I imagine that it benefits both you and the reader, right? Like there's some sort of outline that you have as the person writing this thing that you can kind of shade in. But also to your point, your readers know what to expect.
There's that predictability element. And it would be very easy for me as a reader of yours to pick one thing better out of a lineup.
Like if I just saw it on a PDF and somebody said, whose newsletter is this? I would say, this is Jason's. It's a really strong brand.
So can you talk about that choice? Yeah. Okay.
A couple of things. Number one, as a young writer, I loved stem winders.
I loved the idea of like starting in some random place and building with some narrative and eventually getting to the point. I thought that was really fun.
And as a consumer, I sometimes do enjoy that style if someone's really, really good at it. The only person right now who I can think of that's really good at it is the host of this podcast called 60 Songs That Explain the 90s colon the 2000s, which you must listen to.
It's fantastic. And it always, it takes for like, it takes like 20 minutes to get to the point of the podcast.
He's such a good storyteller that it works. But generally speaking, it's a terrible, terrible way to open something.
And the reason for that is because people are very busy. And especially if you are serving any kind of business audience, those people are really utility oriented.
They want to know what they're going to get from this because they have very limited time and they have too much coming at them all at once. And the only things that will survive are the ones that are clear in value.
I have this concept that I wrote about in a previous newsletter, which I call the first question. The first question is the first question that anybody asks about anything.
And that question is, is this for me or is this not for me? They're always asking that. I mean, think about it.
You are asking that every time you encounter anything in the first couple seconds of this episode of this podcast, you were like, is this for me or is this not for me? And then Morgan said something that answered yes. And that's why you're this far into this episode.
But it could have gone the other way. People might have been like, I don't care about newsletters, and then they're out.
So when somebody opens my newsletter, the first thing I want to do is identify why this is for you, which is why I open by stating the problem, which in this case is you're being misunderstood. Now, you don't have to do it exactly like that, but I do think that it's really important to be as straightforward as possible so that people appreciate value.
You would ask about structure. I do it for a couple of reasons.
Number one, I do it because I want the newsletter to be an easy read. I don't want anyone to ever feel lost in it.
I know that a lot of people are reading it on their phone while they're on the go or on the toilet or who knows. You know, there's a lot of distractions.
So like the format is basically this. It opens like that.
Then it steps back and it tells some kind of story. Sometimes it's about an entrepreneur.
Sometimes it's about me. Sometimes it's some interesting psychological study.
And then it applies that

story to you and your problem. And then it gives you some kind of exercise, a couple of questions to ask, something to do.
And then it just kind of takes it home with a big idea of thought. I repeat that every single time.
It's because the world is full of so much noise that you have to create signal for people. And you do that by being repetitive, but useful.
And so I created a structure that was useful for my reader, but also very useful for me. I know now every single time, once I have an idea for what the newsletter is, I basically just need two things, three things.
I need three things. I need to know what problem am I solving? I need to know what compelling story or anecdote illustrates it.
I need to know what the exercise is. And once I have that, I can sit down and I can write the newsletter.
This newsletter now only takes me, I mean, people, people email me and they're like, you must work on this all week. No, you know, the answer is I, it takes me about an hour and a half to write the newsletter.
And then I like futz with it and polish it. My wife reads it and gives me feedback.
But like the actual writing of it is like an hour and a half. And that's because I have set this formula up and therefore I know exactly what I'm doing and I know what I need to do.
And that makes writing so much easier. Can I get some feedback on my newsletter idea? Please.
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Can I get some feedback on my newsletter idea? Please. Okay.
I'm going to explain this in parts. It's sort of a nesting doll of stories, but you're actually a part of this in a couple of ways.
Oh, great. But do you remember when we went to dinner with Terry and Matt? Yeah, sure.
Okay, great. And Terry Rice, who is multi-hyphenate entrepreneur and consultant, and Matt Gartland, who you introduced me to, how do you even describe Matt? Oh, yeah.
How do you even describe Matt? Well, Matt has a deep background in building companies, mostly digital companies. He was the CEO of Smart Passive Income.
Now he's building a whole bunch of different companies, some of which I'm involved in. He's just one of those guys that builds a lot of things and knows everybody.
Yeah. So super, super smart, interesting group of people.
And you asked a question that I really love and I've asked a lot of people since, which is you asked people, what is the idea for a project that you're holding on to that you just haven't done yet? Oh, yeah. Yeah.
You know what? That was funny. I think that's a great prompt for a dinnertime conversation.
I have all sorts of answers, like this thing that you've wanted to do forever, but you haven't done. But I've actually tried that in a couple of spaces, and most times people don't have an answer to that.
But you did. I did.
I did. And it goes back to so I studied neuroscience in college, and I had a genetics professor who was kind of giving his background.
And he was like, well, like a career advisor asked me once, what's the most important thing that you should be doing right now? And he said, it's studying the brain and genetics. And so that's what he did.
And my answer to that question has always been around the climate crisis and everything that's going on in Los Angeles right now has just been sort of like echoing that back to me. And I'm not actually doing anything.
I'm not doing anything helpful where that's concerned. And so that also led me to go through an exercise, which I learned from you, which is your mission statement exercise.
Can you describe what that is? Okay. So the mission statement exercise is a way to feel grounded in a time of constant change.
So many of the things that you do or that you identify with or that you think you're good at are things that are very easily changeable. And so it's helpful to anchor yourself into something that won't change, to find the thing that does not change in times of change.
And so anyway, what I tell people to do is to come up with a single sentence that starts with I, and then every word is carefully selected so that it is not anchored to something that's easily changeable. The example that I always give is, it's the difference between me saying, I am a magazine editor, which is very easily changeable.
All it takes is one phone call from my boss at Entrepreneur Magazine saying, you're fired, and then I'm not a magazine editor. So very easily changeable.
Two, I tell stories in my own voice, which is not changeable. Stories can happen in any format, in any medium.
In my own voice is me setting the terms for how I want to operate at this stage of my career. So for you, it could be, I solve the most complex problems.
I help teams achieve greatness. Whatever it is,

once you have that clarity, you realize that anything that changes in your work or life

is just a new opportunity to do the thing that you already do best.

I have found that so helpful. And I applied that to this problem because I thought,

okay, so the problem is global warming. Yeah, okay.
Global warming, that's a problem. Global warming, it's a problem.
Heard of it. But what am I actually good at? And that's kind of more how I thought about using the mission statement exercise.
How can I leverage what I'm good at to make any sort of an impact? So what I arrived at for my mission statement is I am good at simplifying academic topics through storytelling. That's something that I've always been good at.
I was a tutor in college and I helped people in their science courses who like, you know, had to take them liberal arts major. It was a requirement to graduate and just tried to use storytelling to explain the academic concepts.
I do that at MNN through writing business and finance content, often very academic, but I can make them more palatable through storytelling. So I think a newsletter is actually a good format for me for this.
But where I feel like there is need is a lot of the people who write about climate, write about the very far end of the spectrum in terms of action, which looks like making lifestyle changes that are very dramatic. Like people writing about not flying on airplanes anymore or only wearing hemp.
Things that people are just not going to do. I'm not going to do that.
And so what I want to see and what I would benefit from is somebody writing from the perspective of what can you do to be better, but not the best. And so I have sort of in my head called my newsletter greener for that exact reason.
Like, how can you be greener? And so my idea is that throughout the course of the week, I would focus on one thing that's hurting the planet, like microplastics, the meat industry, things like that. And then I would think of something that I could do consistently throughout the week as a sort of challenge to help that problem.
Like this week, I'm not eating any meat. How did that feel? What was hard about that? This week, I'm not using any single use plastic.
What was hard about that? Did I do it? And then writing about that and my experience with it. And then, you know, sort of like at the top, my first section would be, why is this a problem in the first place? And something that I am thinking about doing too is at sort of the end of the newsletter, I would say what the challenge that I'm setting for myself is going to be throughout the next week

so that people could try it too. And I think that that would sort of incentivize people to continue to read because they are kind of like following along.
We're doing this together sort of a thing. So that is my idea.
What do you think? There are parts of it I like. There are parts of it I don't like.
Yay. Perfect.
I want to hear all of it. What I like is that you have a point of view and that you are approaching it in a way that feels relatable and useful to an audience.
I think that's great. I like that you have identified that you have a specific approach that differentiates you in a market.
What I don't like is how complicated it is. Because I don't think that you can actually sustain doing a different kind of experiment on yourself every week in a weekly newsletter.
I think you will burn yourself out instantly on that. It's too much work.
I think you need to find ways to produce a newsletter that really don't take you that much time. Because putting together news, look, consider the experience of a newsletter for people.
It's pretty short. People are going to open it.
They're going to read it once. They're going to likely delete it.
Some people tell me that they save my newsletters, and that's cool. But it's a pretty...
It's like an experience in aggregate. It's about building a long-term relationship with people.
So each newsletter should be good, but you shouldn't pour a full week's worth of personal experimentation effort into each newsletter. You will run out of topics too quickly, and you will burn yourself out.
I'll give you an example of something that is much smaller in scale, but takes this same sort of approach of distilling academic information to something that's useful. There's a guy I know named Thomas who has a newsletter called Science Says.
And it's very simple. Each week he finds some academic paper on marketing where they're studying like, you know, if you put the price above or below the product in an advertisement, which drives sales more? But these things are buried inside of complicated academic papers.
And so he makes it simple. He just brings out the biggest, most important piece of information, quickly summarizes the main points of the study, gives you some actionable takeaway.
I find it very useful. It's a great distillation of insights that are otherwise trapped inside of academic journals.
And it's great for marketers, which I'm interested in. I feel like you could probably do a version of that.
There's got to be all sorts of interesting science out there about the climate that could be made useful for people without consuming a full week's worth of your time. And also, look, you also, one other thing, you have to, especially when you're starting a newsletter, you have to guard yourself against the dispiriting experience of not that, newsletters are hard to grow.
And if you get like a, you know, if you get a 40% open rate, you are killing it. So you're not going to reach that.

You're not reaching that many people.

And so if you spent like a full week not eating meat

and like chronicling everything

and putting together this like loving thing

and then very beginning, like a hundred people read it,

you're going to be like, screw this.

I hate this, right?

So you've got to do something that's just,

that's just like lighter for you

and lighter for your audience.

But I like the starting point that you have and I think that there's a lot to build from there. Hold on to your wallets.
Money Rehab will be right back. And now for some more Money Rehab.
So that's the advice that I got from Jason. And oh my God, it's so painful to listen back to me explaining my idea.
If it takes you five minutes to explain a newsletter concept, it probably needs some work just as a general rule. But let me just take a step back.
The idea for greener hit me two years ago on a day in June when the sky in New York was red. And this wasn't the first time I had felt anxiety around climate change.
I doom scroll on climate news and click on any headline about how the world is going to end in 150, 30 years. So while it wasn't a new feeling.
I had never really done anything about it. And like I said to Jason, I'm not going to pull up a seat alongside Greta Thunberg on a sailboat in order to get to my friend's wedding in California.
To be honest, whether it's my love of my carbon indulgences or just laziness and a dependency on convenience, that extreme way of living is just not going to be something that I do. But I know I have to make some changes because I see it happening.
I see the effects of climate change all the time. I grew up in Maine and Maine winters used to be just the bane of my existence.
We used to get so much snow that at our local movie theater, the people that worked there would change the names on the marquee by climbing the snow banks. That's how high it was.
You could reach the marquee in the movie theater just by standing on the snow bank. But now winters are just manageable.
January used to be so bitterly cold that it felt wrong to be outside. But now the mildness, it just feels worse.
It's kind of like the quiet, too quiet of temperatures. But there are bigger signs, of course.
I mean, look to Los Angeles, which we'll be covering more in the coming weeks. But beyond that, flooding, earthquakes, hurricanes, wildfires, I know I need to change and I know I need to be greener.
But I couldn't find a resource out there that was situated in this middle ground that I wanted to occupy. Every resource I found was either a really drastic departure from what my life looks like now a la sailboats and Greta Thunberg or just eye rollingly obvious ordinances to turn the lights off and take shorter showers and I couldn't find anything for where I was at just non-judgmental advice for someone not wanting to be perfect, but just better.
So I thought that I

could make it with my newsletter. And I could try to do one thing every week that would help me live

a greener life and talk about why it worked and how it worked. But Jason is totally right.
My idea

is too complicated. And it actually used to be even more complicated.
I was going to include

interviews with people solving climate issues at scale. I'm definitely not doing that anymore.
I've been thinking a lot about what Jason said since we spoke. And again, he is totally right and his advice is really solid.
But I am going to inexplicably still try to do the unmanageable thing. The thing that he said would make me burn out.
And that's because I'm not thinking about doing these climate experiments, as he called them, just to write about them in a newsletter. I want to do them anyway because I think I should be more conscious about my footprint.
So I actually think that writing about it and starting this newsletter will help me make some real change in my life and hopefully in others too. But I am going to forget putting in interviews and some of the other section and segment ideas because I should try to decomplicate this workflow for myself.
He's totally right. This conversation left me feeling really excited.
So once I felt like I had my idea workshopped, it was time to make the thing. So this is when I talked to Alyssa Doolin.
Again, she manages the creator growth team at Kit. I asked her all of my technical questions like, how do I protect myself from being sent to spam? How do I get people to open my emails? Oh, and importantly, I'm not a celebrity, so how do I actually get people to find my newsletter? She helped me out with all of these questions.
Here she is. I have some questions for you, Alyssa, but my biggest worry is that I just don't know what I don't know.
So I actually want to start by asking you generally, what are some important best practices when starting a newsletter? Yes, this is a great question. Starting with your subscribers that are coming onto your list, remembering that these are all humans.
I know sometimes we see email addresses and we are trying to get the biggest list as possible. Sometimes it gets lost in the shuffle that like, okay, these are real humans.
How do I take care of them as my subscribers? And so I think first electing those subscribers, doing so in a way that's consent-based, making sure people want to be on your list and not trying to grow your list in a way that's all about growth. Sometimes that can get us in tricky situations where we're like, what if I run a giveaway for a Peloton if you give me your email address? And then it's like, well, those people just wanted a Peloton.
They don't really want your newsletter. How do we get them excited about your newsletter? And then once they're on the list, what's the experience? Are you welcoming them? Do they know what to expect? How often are they hearing from you? And all of those things cover a lot of email deliverability issues where emails might start going to spam.
You're having trouble. Some of that can get into technical weeds, but a lot of times it comes down to the humans, the subscribers.
Are they happy on your email list? Do they want to be there or are they marking you a spam? And then that's causing some issues. Yeah.
You just touched on so many things that I want to circle back to and double click on, but you mentioned the user experience and how you're welcoming people. And that reminded me of the fact that for the newsletters that I subscribed to, when I first subscribed to them, I did get like a welcome email.
Is that something that you recommend creators have? I do. I do recommend it for a few different reasons.
But one of them is just that we have some short attention spans a lot of us do and we're signing up for things and we're forgetful and so if you don't have a welcome email someone might sign up to your list after they see something you've you know posted somewhere or they're excited about something they've seen and then a week goes by they've lived a whole life in a week and then they get your email and they're like, what is this? Who is this person? I've forgotten this name. I don't know.
I didn't sign up for this. Marcus Bam.
So that welcome email is a great way to write out of the gate, someone just signed up, welcome them, remind them, hi, here's who I am. Here's what to expect.
I'm going to be sending you XYZ over X amount of time. And another little pro tip, in that welcome email, ask them to reply to you.
It boosts your sender reputation and will help with deliverability because that helps the algorithms that like Gmail and Microsoft have think, oh, this is a wanted email. It's kind of a one-to-one email where they're emailing each other instead of seeing you as this bulk sender who's just blasting out emails to a bunch of people at once.
Okay, interesting. And so that is something that would potentially help my email not be flagged as spam.
Yes. So let me know if this is getting too deep, but essentially your subscribers are sending signals to the mailbox providers like Gmail, Yahoo, Microsoft that tell them whether this is wanted email or whether it's spam email.
And those signals are replying. That's a really positive signal.
Opening the email, positive, clicking, positive. So that's all great.
And you want to optimize for those. Some negative signals are not opening emails after time and time

again, you've sent them emails or the most negative one marking a message as spam. So you want to

avoid those signals and optimize for those positive ones where it's showing engagement.

Okay, great. So say I am sending out my first email and I've asked some friends to subscribe.

So I have some people that are on the list already, but I haven't sent anything yet. Is there anything I should be doing for the very first newsletter that I send out that will increase the probability that my email doesn't just automatically go to a spam or junk folder? That's a great question.
I think I would do exactly what you're doing, which is starting small with people who you know or they've signed up to be there. And then you should be in a really healthy place.
And then from there, if you grow your email list with, again, people who want to be there, then I wouldn't expect to see any issues. Where I see some issues sometimes is if someone starts that very first send off with a larger list that's maybe gone cold.
You haven't emailed these people in a while. You might be like, well, this is from my other side hustle I had two years ago that I kind of abandoned.
I collected an email list back then, but now I'm starting a new newsletter. Let's send them this new newsletter.
That's when I see things start to go wrong. And that very first send does not go well.
So again, I think as long as you're starting on a really healthy starting point with people who want to be there, a smaller list, and then you ramp up slowly, then you should be good to go. That's great to hear because I have sort of been sitting here thinking that I don't have a big list to start.

Like I'm not going to get a lot of people to sign up initially.

I just know that to be true.

And I have been sort of taking myself thinking that that's a bad thing. But it's nice to hear that there are some kind of good things about it too.

So that's really good to know.

Some other things that you mentioned around user experiences like length and cadence. How often are your subscribers going to be hearing from you? These are the things that I'm thinking through right now, like all of these little decisions around how long the newsletter is going to be and what is the cadence? And should I have headings in different sections and things like that? Are there any lessons from Kit's top writers about what works? Definitely.
Yes. Everyone has their own take on this and there isn't a one size fits all, but what we can learn from the top senders is that consistency is key.
You know, we all have heard that before, um, making sure people know what to expect. So I'm thinking of like Tim Ferriss's five bullet Friday is one of our most successful newsletters.
Everyone knows you're going to get it on Friday. It has the same format every week.
There aren't a lot of surprises and it's consistently great content. So whatever you choose, I would just keep it consistent, whether it's a monthly roundup or it's a weekly digest, whatever it may be, just stick to it.
And then when I think of our top performers, they keep consistent formats, like I just mentioned, making it easily skimmable too. You don't want someone to open it up to a wall of text or a huge list of links.
When I think about Tim Ferriss or Sahil Bloom or James Clear's weekly newsletter, I think of the fact that, again, they keep their format consistent every single time. And it's really easy to see the heading.
There's some information below, maybe a call to action with a button or an image, and then another heading. And then you can kind of pick and choose where you want to give your attention.
So you don't have to read the full newsletter if it's not all related to you. So those would be my two top recommendations are consistency in the frequency and then consistency in the layout and making it really easily skimmable.
Okay, great. That's really, that's really helpful.
I know another thing that people look at really closely and want to make sure they optimize for is a good open rate. Do you have any tips on getting a good open rate? It's such a loaded question because really over the last like five years, open rates are a tricky metric.
They're not totally accurate. So look at open rates more directionally than this is exactly true.
50% of people open my message. Definitely not the case because again, I'll keep it really high level, but an open is triggered whenever a little invisible pixel in the email is loaded.
It's basically like an invisible image. And that tells us and mailbox providers, the email was opened, but people like Apple, Apple mail, the app on your phone or your computer will automatically open emails on your behalf as like a data privacy protection measure.
So you're going to see a lot of people that say they're opening emails and they're not really opening emails. Yeah, which is a bummer state of, you know, email marketing right now.
But the way that I find open rates to be helpful, again, is looking at trends. So if you are used to having a 40% open rate, and then one week you send it and it's 32% open rate, then you know something's definitely going on here.
But to get to your original question, like how to have those high open rates, I would say some important things are your subject line, making sure that it's grabbing people's attention. You also don't want to be clickbaity.
I know sometimes you can get into that territory, but still like making it engaging so that you stick out in the sea of other senders. For some people, adding like an emoji is helpful.
Other people doesn't work as well. That's another thing is get to know your audience.
Everyone's audience is different. Run some tests.
In Kit, you can A-B test your subject line. So you could do one with an emoji, one without an emoji, and see which one wins.
That's one really important way to increase your open rate. And I think other than that, it's really just providing consistent value so that your readers are excited to go open that message every week.
I think you can build trust that way, get people excited for your email versus if you start to kind of drop off in consistency or quality of content, then it's going to be a situation where your subscribers aren't like jumping to open the email every week. That's really helpful.
And I alluded to this before, but I am not a celebrity. I am not Tim Ferriss.
I don't have a big audience of people that I know are going to subscribe to the newsletter. And so I effectively, in order to grow it, need to kind of get strangers to discover it.
I don't have an audience that I'm tapping into. And so how do I do that? Like, how do I grow a newsletter beyond what my own personal reach or network is? I have a few ideas here.
That's one thing my team at Kit helps people with. And I've seen such really creative ways to do this.
One of my favorite ways I'm seeing people do this lately is using Instagram to create reels that are related to your newsletter, whatever it may be. And then using, I think the tool a lot of people use is mini chat, where you say like comment newsletter and I'll send you a link to the newsletter.
So grabbing people's attention that way is really great. And then it kind of goes along the second idea.
You could kind of combine the two, which is lead magnets, or I've seen people do this through an email course. So let's say you're an interior designer and you say, I have a five day redo your house on a budget course, sign up here, and I'm going to send you an email every day.
Or you can do email challenges, things like that really get a lot of subscribers. And then they'll start receiving your newsletter.
And then they know you better. They know your content better.
You provided them free value off, you know, right at the beginning. And that sets such a great subscriber relationship up when you've already given them free value.
They're usually a lot more loyal to your newsletter, really engaged. So I would think about how can you create some sort of free email course challenge, something like that, where you can get people opted in and then they'll start receiving your newsletter.
So lead magnets, that's something I'm familiar with. I don't know if I've ever heard of someone doing an email challenge or a newsletter challenge.
What would that look like? Like what's an example of something someone has done before? Let's say it's the new year and you are a copywriter coach. You can say, join me in this writing challenge in January every single day.
I'm going to send you an email with a prompt. And I'm going to want you to journal on that prompt.
Send me a reply. Let me know how it went for you.
And then you can start to include people's replies in future emails, which is really cool way to tie things in. On the money side of things, budgeting, you could say, we're going to do a no spend budgeting challenge together, sign up for my email, I'm going to send you a daily email with tips on how to budget better.
I mean, I'm like, I would sign up for that right now. Somebody offered that.
So just sort of like in sending daily short emails where you're giving someone a prompt or a challenge. And then it's really fun again, if you can tie it into like reply and tell me how it went or go to this Facebook group, we're all going to be in this group together.
And we're going to talk about the challenge, the prompt of the day and create some community there. And I know that another tool that Kit has, so I'm going to start my newsletter on Kit.
I have not sent anything out yet, but I did create an account. And I know that there is tech within the platform to cross-promote newsletters.
So I could do a recommendation swap with another writer on kit. And I think the way that this would work in, correct me if I'm wrong, is if like someone subscribes to my newsletter and I'm recommending some, you know, let's say Jason's newsletter that when they subscribe to mine, they would get a pop-up that's like, you might like, or like this author recommends or something like that.
Do you have any sense of best practices around that? Because I can see like it being a really good idea to just try and get a recommendation from someone with a really big audience, but is it perhaps more important to work with someone who's like writing in the same genre that you're writing in? Or like, what are some of the considerations for using a swap tool like that? Yes, such a great question. I love chatting about this.
It's our recommendations tool. You might've heard us call it the creator network, but I would say that it's helpful to kind of think about it through your subscribers perspective and think about which creators would be helpful for them, which newsletters would be helpful for them.
That might be within the same niche as you, which is great, or it might be an adjacent niche. So, for example, I have a newsletter on there that's all about email deliverability.
And I have people who recommend me who are focused on email marketing strategies. And our content's a little different, but it's similar niches.
Or you might have like a lifestyle blogger recommending a food blogger and it's very related. So I think that's what I would look for.
Luckily, our discover tab, you'll see it in the app where you can kind of browse through people has gotten this. I actually was looking at it today.
I was like, wow, this has gotten so robust where if you start to find people that make sense for you and you recommend them, that page is going to get way smarter. And now it's going to show you people that we think you might be a good fit with based on who you've started to recommend, because we're going to look at, well, who are they recommending? You might like who they're recommending.
So there's cool. Yeah.
The tool will kind of help surface some ideas for you. And then from there, just wanted to call out that once you start using it, which it's been awesome for me, I don't even touch it.
And I've gained like 2000 subscribers really doing nothing. Some people, those numbers are way higher.
It's crazy. But I would say, make sure that you have a welcome email set up for anyone who comes through recommendations because they're really not going to know much of who you are at all.
So that introduction is so important. And then you can also set up an automation that will automatically remove anyone who comes in through recommendations and doesn't open an email within X amount of days.
So you can decide whether you want that to be really strict at 30 days or 90 days, something like that. So those are the two big things I would recommend to have success with it.
Okay, great. That's really helpful.
And in terms of like, you know, because in a best case scenario, I would recommend a newsletter and they would recommend me back. If I recommend a newsletter, does the writer of that newsletter see that on their end? They do.
They receive an email too, letting them know. Yeah.
So there are multiple kinds of things because we want the same thing like for people to find connections and to recommend each other. So the interface is going to give them plenty of prompts and let them know that you're recommending them, which is great.
It helps a lot of people get visibility that they wouldn't have had otherwise or like get to know other newsletter operators that they wouldn't have known previously. Great.
This has been really helpful. I really appreciate it so much, especially just because I'm going through this myself and it's all very new.
So getting expert advice is really helpful. Is there any other last parting piece of advice that you would give me and anyone else who's starting a newsletter from scratch? One, I'm thinking of like two things.
If you're like me and the weekly consistency is hard, there's a tool I've used in the past that's so helpful, which is setting up an evergreen newsletter. And again, this is like, if you're not able, or you're having a hard time keeping up that writing an email every week, you can set up an automation where someone will subscribe to your list and then they start, they get email one.
And then it says one week later, send them email two. And you can have this just set up, take the time to write the content for as many weeks as you'd like.
And then it's there, it's running in the background for you until you can go update the copy anytime. So you definitely want it to be pretty evergreen to where it makes sense in any month or whatever.
But I've just found that so helpful for me to make email more sustainable for me. So if you're a person who's like always wanted to do this, but it feels scary to commit to it, look into doing an evergreen automatic newsletter.
Wow. I didn't even think about that as a possibility.
That's really useful. And so before I let you go, Alyssa, what's the name of your newsletter so people can subscribe? Yeah, it's called Deliverability Dispatch.
Honestly, it's not getting a lot of love right now. But if you're listening to this and you're like, oh, I want to learn a lot more about email deliverability, we do have a podcast.
It's called Deliverability Defined that we have here at ConvertKit or it now. It's me and my coworker, Melissa.
So we have a few seasons out and highly recommend checking that out if you're interested. That was my conversation with Alyssa.
And not only did I find her technical advice helpful, but it also helped me think about my creative. Both Jason and Alyssa mentioned that a newsletter should be easily readable.
The way I had been thinking about my newsletter was part journal almost, so that's not particularly readable and definitely not skimmable. So it made me start to think that I should have some sort of heading at the top for out-of-the-box tips for being more sustainable that could suit people who were just looking for a quick read.
But I'll be honest, I started to kind of freak out at this point. I started to doubt my concept.
I worried that Greener would not be successful, and that's actually the reason this episode is coming out so late today. I've been having a bit of a crisis of confidence, and I think that's why it's taken me two years to get to this point.
In all of my jobs, I've been behind the scenes. I'm a producer.
Before that, I was an assistant. I've always put work out under someone else's name.
And it's scary to think about putting something out with your own name. Nowhere to hide.
So today, I just kept going back and forth about how to get my concept perfect. But I think what I've come to accept is that it just won't be.
And that's okay. My newsletter doesn't have to be in its final form

now. I can try things and then try some other things and then keep doing that until I like it.

So giving myself a little grace made me put some of the final touches on my welcome email

and my landing page. All right, now we're looking at fonts.

How do I make this bigger? Feels like it should be bigger. I want the font to be a little bit more blocky.
Dare we just do aerial? We don't dare. We don't dare for that.
I guess I can always change this if I end up hating it. I heard once that medical school applications that used Georgia were accepted at higher rates.
What if I just make everything Georgia? I'm so confused, I did this already. What's the difference? Nobody knows.
Did I break it? I wonder how I fix that. That is actual audio of me tinkering with my landing page.
There's actually 25 minutes of that, but I am going to spare you. And now I have a newsletter.
It exists. It's not perfect.
When you subscribe to my newsletter, it says something weird like, thank you for subscribing. You will receive my emails when I send them in the future, which is not something that I would actually ever say to anyone.
And in the picture of myself that I used for the photo from my newsletter, I have a gigantic sunburn on my chest. The URL for my landing page is greener.kit.com slash F6A2222630.
And I don't know how to change that, but I have it. It exists.
Tomorrow I'll make it better. And right now that's enough.
And so if you're listening to this and it's helped

you think about how to make a newsletter that will further your mission, work or otherwise, just know that's enough. Don't wait two years.
The day for making it perfect will be tomorrow because perfect and tomorrow are both concepts that are just not achievable. But today, just make it.
I can't wait to read it. And hey, you can subscribe to my newsletter at greener.kit.com slash F6A2222630.
But I also put it in the show notes. Money Rehab is a production of Money News Network.
I'm your host, Nicole Lappin. Money Rehab's executive producer is Morgan Lavoie.
Our researcher is Emily Holmes. Do you need some money rehab? And let's be honest, we all do.
So email us your money questions, moneyrehab at moneynewsnetwork.com to potentially have your questions answered on the show or even have a one-on-one intervention with me. And follow us on Instagram at Money News

and TikTok at Money News Network

for exclusive video content.

And lastly, thank you.

No, seriously, thank you.

Thank you for listening and for investing in yourself,

which is the most important investment you can make. Thank you.