5 Newsletter Growth Lessons From 2.5 Years of Publishing

Summary

Episode Summary: "5 Newsletter Growth Lessons From 2.5 Years of Publishing"

Growth In Reverse hosts Chenell Basilio and Dylan Redekop delve deep into the strategies and insights behind building a successful newsletter. In this episode, featuring a conversation between Chenell Basilio and Darrell Vesterfeldt, they unpack five crucial lessons learned from Chenell's 2.5 years of publishing her own newsletter, Growth in Reverse. The discussion offers valuable takeaways for anyone looking to grow their email list and transform their newsletter into a thriving business.

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1. Origin Story of Growth in Reverse

Chenell shares her journey from leaving her day job in 2017, where she specialized in helping online businesses through Facebook and Google Ads, to founding Growth in Reverse. After experiencing significant burnout during the COVID-19 pandemic surge, she pivoted towards creating valuable newsletter content. Inspired by Mario Gabrielli's success with his newsletter, Chenell invested extensive time reverse engineering successful creators, leading to the inception of her newsletter in December 2022. Starting with just four subscribers, including herself, her dedication and passion fueled the growth to 40,000 subscribers.

Chenell [01:50]: "I went back, I listened to all the interviews he had done and went through all of his posts and his tweets and everything... that first issue went out to three people."

2. The Power of Valuable Content

A recurring theme in the conversation is the paramount importance of creating insanely valuable content. Chenell emphasizes that regardless of the growth hacks employed, the quality of content remains the foundational pillar for success.

Chenell [08:13]: "There’s three things. The first one is something everybody hears all the time, but insanely valuable content... If you don’t have good content... you’re going to struggle."

She further breaks down what constitutes valuable content into six key elements:

• Save Time
• Make Money
• Save Money
• Make Them Feel Something
• Teach Them Something
• Speed to Market

Combining multiple elements from this list magnifies the content's impact.

3. Building Community and Collaborations

Chenell highlights the significance of community building and collaborations in sustaining newsletter growth. Being part of communities like Jay Clouse's lab and engaging in masterminds has been instrumental in her journey. Collaborations, whether through cross-promotions, guest posts, or joint projects like summits, are identified as the backbone of sustainable growth.

Chenell [13:18]: "Most of the growth levers I’ve seen sustainably work over time just come off the back of collaboration."

Darrell echoes this sentiment, contrasting collaborations with the often less effective strategy of purchasing ads or subscribers.

4. Consistency and Time Investment

Consistency emerges as a critical factor in newsletter success. Chenell advises starting with a manageable frequency, preferably weekly, to build trust and maintain engagement. She cautions against jumping into daily newsletters unless one can sustain the effort, as frequent sending can lead to higher unsubscribe rates.

Chenell [17:57]: "If you can only do two, two times a month, that’s fine too. But have the goal of getting to weekly."

Darrell underscores that building a successful newsletter is a long-term commitment, emphasizing that trust and audience relationships are cultivated over time.

5. Monetization Strategies

Monetizing a newsletter is explored through various avenues:

• Sponsorships: Chenell successfully secured her first sponsor with 1,100 subscribers by leveraging strategies learned from Josh Spector.
• Affiliates: She incorporates affiliate links by promoting courses from creators she features.
• Community Memberships: Launching a community for newsletter growth has become a significant revenue stream.

Chenell underscores the importance of sponsorships as a low-lift entry point into monetization, transitioning into more substantial revenue streams as the newsletter matures.

Chenell [38:34]: "Affiliates are great. I naturally write about creators who might have a course... I also launched a community for other folks growing a newsletter."

Practical Steps to Grow from Zero to One Thousand Subscribers

Chenell provides actionable strategies for beginners aiming to grow their newsletter audience:

1. Engage on Social Media: Focus on one platform to start, actively commenting and interacting with other creators to drive interest.

2. Build Relationships: Join communities and mastermind groups to network and collaborate with like-minded individuals.

3. Consistency: Maintain a regular publishing schedule to build trust and reliability with your audience.

4. Refine Content: Continuously improve your content based on feedback and engagement metrics.

5. Collaborate: Initiate cross-promotions and partnerships to tap into existing engaged audiences.

Chenell [19:22]: "Pick one social media platform and go there first... it’s okay. But I would say start engaging on other people’s content."

Overcoming Emotional Barriers

Chenell addresses the emotional challenges of outreach and collaboration, advising creators to view subscriber growth as a game to mitigate self-worth issues tied to numbers. She encourages resilience in the face of rejection and emphasizes the importance of persistence.

Chenell [24:34]: "If I'm like, oh, I had five today and tomorrow I have six, it’s like, not about me anymore. It’s about that number."

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Final Thoughts

The episode reinforces that while there are no shortcuts to building a successful newsletter, unwavering commitment to creating valuable content, fostering community relationships, and maintaining consistency are pivotal. Chenell's journey with Growth in Reverse serves as a testament to the effectiveness of these strategies, offering listeners a blueprint to emulate in their own newsletter endeavors.

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Notable Quotes:

• Chenell [08:13]: "If you don’t have good content... you’re going to struggle."
• Chenell [13:18]: "Most of the growth levers I’ve seen sustainably work over time just come off the back of collaboration."
• Chenell [17:57]: "If you can only do two, two times a month, that’s fine too. But have the goal of getting to weekly."
• Chenell [19:22]: "Pick one social media platform and go there first... it’s okay."
• Chenell [24:34]: "It’s about that number."

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This episode of Growth In Reverse is a treasure trove for aspiring newsletter creators, offering both strategic insights and practical advice grounded in real-world experience. Whether you're just starting or looking to refine your growth strategies, the lessons shared by Chenell Basilio provide a roadmap to building a lasting and impactful newsletter.

Transcript

[Chanel]

Hey, friends. Chanel here. Today I'm sharing a conversation I had with my friend Darrell Vesterfeldt on the Mighty Network Summit. We just had a great conversation. I heard a ton of great feedback. People personally reached out and said they enjoyed it. So I wanted to share that with you here. We talked about a bunch of stuff, but we really dug into the exact steps you can use to go from zero to a thousand subscribers without using ads. We got real about handling rejection when you're asking for collaborations or outreach and that kind of thing, and kind of knowing how to stay the course versus when to pivot your content. Plus, of course, I can't do anything these days without talking about insanely valuable content. You'll also hear why I was comfortable spending 30 to 40 hours a week on my newsletter before it made a single dollar. For months. We just kind of sat down and talked about, you know, nerdy newsletter stuff, which I always enjoy. So I wanted to share that with you here. Hope you enjoy.

[Darrell Vesterfeldt]

We are going to talk to my friend Chanel, and Chanel is a hero to me in a lot of ways because Chanel didn't wait around to have a mentor who's been there before. She didn't wait around to have somebody tell her exactly what to do. She has been spending the last several years reverse engineering some of the most successful creators and what they've done to grow their audience and their newsletter. Chanel is the founder of Growth in Reverse, one of my favorite newsletters and one of the most popular newsletters in the creator economy. So excited to welcome Chanel to the main stage today and excited to have a conversation. Chanel, welcome.

[Chanel]

Hi, Darrell. That was way too kind of you to say all of that. Thank you so much.

[Darrell Vesterfeldt]

Way too kind. It's just the truth. I only speak the truth, Chanel.

[Chanel]

Okay, I'll take your word for it.

[Darrell Vesterfeldt]

Tell us a little bit about Growth in Reverse. I want to hear the origin story, a little bit of it, because I think it's so inspiring that you basically were just like, how does this work? And you just started reverse engineering a bunch of successful creators. So tell me more about it.

[Chanel]

Yeah, sure. So I actually left my day job back in 2017, and at the time, I was helping online course creators and other folks online build their businesses through Facebook and Google Ads. And so I was doing that for a few years. Covid hit, my business boomed. I was doing super, super well, to the point where I took on way too much work and ended up burning out really hard. So after that, I was Like, I don't want to do services anymore. I'm not sure what I want to do. I was always interested in stuff like this. And then I found this guy named Mario Gabrielli. He writes a newsletter called the Generalist. And I've saw a post that he had written where he said that in his first year as a newsletter writer, he was making $300,000 by himself. And I was like, hold on, wait, What? A newsletter making 300 grand? I am naturally a curious person. So I was like, okay, how did he do this? I went back, I listened to all the interviews he had done and went through all of his posts and his tweets and everything. And I put together, like, probably 50 to 60 hours of research into this long form article. And I was like, you know what? He wrote a newsletter. I wonder if other people would be interested in reading this. Like, why don't I send this out as a newsletter? That first issue went out to three people. Well, four. One was myself, my own email address. That was back in December of 2022. And since then, I just kind of kept going with this whole newsletter growth thing. And now we're at about 40,000 subscribers. So. Been a journey, but it's been a fun one.

[Darrell Vesterfeldt]

How did. How did you decide the topic of the newsletter? How did you decide that this is the newsletter that you would get really excited about doing for a long period of time?

[Chanel]

I didn't, to be honest with you. Like, I just started and I was like, you know what, this is super fascinating. I don't know if I'll do another one of these, but I really enjoyed the process. And it was cool to learn about how this guy grew a newsletter. And then people started eating it up. Like, I shared, I think I posted a thread on Twitter and like, you know, six people liked it or something. And I was like, that's pretty good. And then thankfully, Jay Clouse was one of my early subscribers, and he ended up sharing it out in his newsletter. And I got to like 55 subscribers. And I was like, all right, I'm just going to keep going with this. And so every week from there, I wrote another deep dive. And they took like 30 to 40 hours each one to write. So it was a lot. But I'm. I don't know, it was just fun. So I enjoyed it.

[Darrell Vesterfeldt]

Other people, like, 30 to 40 hours to write a newsletter.

[Chanel]

Yeah. So I would go on these long walks and listen to podcast episodes and figure out how people grew their newsletters.

[Darrell Vesterfeldt]

That's so crazy to me. How. Okay, So I want to. I want to tap into that, because you're not making any money from the newsletter. You've got 55 subscribers, and you're spending 30 to 40 hours doing it. Like. Like, that. That equation doesn't make sense in my head. Tell me, like, how it made sense to you and why you decided to commit in that direction.

[Chanel]

It wasn't logical, I will say that. But I was enjoying it. And, like, coming from this place of extreme burnout, I was like, I'm just gonna follow what I'm enjoying right now. And, like, thankfully, my business had done well, so I had probably a few months of savings saved up. So I was like, okay, I'm just gonna see what happens here. And I'm somebody who, like, picks up hobbies and drops them like, three months later. So I didn't know if this was gonna last, but I was like, you know what? I'm gonna. I'm gonna try it out and see what happens. And I just kept going with it. There wasn't, like, this strategy. Like, I didn't stop at any point and be like, should I continue doing this because it's a good business? Like, I just did it.

[Darrell Vesterfeldt]

Well, what. What kept you going then? So if you didn't, like, stop and be like, okay, well, this is working well, like, what kept you going? Because, hey, that's a huge commitment. Like, just. Most people don't even do real work for 30 hours a week. They're, like, scrolling on Instagram or Facebook most of the time anyways. But, like, how do you decide to do that when you're not making money yet? What's, like, pulling you forward still in the midst of all of that?

[Chanel]

Yeah, I was just having fun. Like, I was honestly, genuinely having fun with it and being able to combine my natural curiosity with something people could read and enjoy themselves on the Internet. Like, I thought that was super cool, and so I just kept going with it.

[Darrell Vesterfeldt]

That's so fun. I didn't even realize that you were spending that much time on a newsletter. Otherwise, we would have maybe called this how to spend 30 hours writing a newsletter session. That's so inspiring to me. Rick said something here in the comment, and Rick is a legend in the Creator Summit world, but Rick said, like, the power of doing something you're passionate about or something that you really enjoy. I think it's totally underrated. I think a lot of times people think about, like, well, is this a good business? Or, can I make money doing this? And what they don't realize is that you can burn out really quickly if you don't actually enjoy the thing that you're doing along the way. And if you're going to create a business, you might as well do something you enjoy or that you're passionate about along the way, too.

[Chanel]

No, totally. And if I wasn't, I probably wouldn't have kept going with it, because I was. At that point, I just needed something fun to do. Like, I just needed to get out of my head from failing at my last business. So it worked out well.

[Darrell Vesterfeldt]

And fun to you is 30 hours per newsletter. I love that before you and I maybe are a little bit different, which I love. Okay, so you started writing these newsletters, you were listening to podcasts, you go for long walks, you're reverse engineering other successful folks. When did you start making money? Or, like, what was the inflection point of growth where you, like, woke up one day and you're like, this is actually going to work and I should keep doing this, not because I love it, but because this is actually going to turn into a business. Like, what was that moment for you?

[Chanel]

That's a good question. I think I had seen enough people making money with newsletters that I was like, this could potentially be a thing. And then I think it was like, 1100 subscribers in. So probably five months in, I had my first sponsor and I was like, okay, that's how I made money. I followed a guy named Josh Spector, and he actually had outlined this way that he gets sponsors on JCloss podcast. I just followed that to a T, essentially, like, add a spot at the top of your newsletter and say, like, hey, I'm thinking of potentially adding a sponsor here. Are you interested? And then you can say, yes, no, maybe, and have people click the specific link of their vote. 98% of people said yes. One person maybe said no. And the other people were like, yeah, I'd potentially be a sponsor. So you actually have this pipeline of potential sponsors before you even launch, which is kind of cool. And from there, all the sponsors have been inbound. Knowing Justin Moore's strategy now, it's probably not the best way to go about it, but it's worked out well in terms of sponsors.

[Darrell Vesterfeldt]

So, yeah, that's great. So reverse engineering the most successful newsletters and how large creators are building their audience, this begs the question, what have you learned in the last couple of years about the people who are doing this at the highest level? What are some of the key takeaways or points that you've learned from them?

[Chanel]

Yeah, so I think there's three things. The first one is something everybody hears all the time, but insanely valuable content. Like I just, I've outlined this before. Everybody wants to gloss over it, but it is literally the thing that got me going. My content was unique. People really enjoyed it, so they were sharing it without me asking them to. If you don't have good content or something good to say something that's going to catch people's attention and hook them really well, you're going to struggle. And I hate to say that, but it's true. Every other growth hack off the back of that either works or doesn't based on the level of the quality of your content.

[Darrell Vesterfeldt]

So that is like foundational pillar, hence spending 30 hours.

[Chanel]

But you don't have to necessarily. But yes, that is one way to stand out.

[Darrell Vesterfeldt]

That begs the question, what qualifies as valuable content or what makes something valuable?

[Chanel]

Yeah, so I. There's been like over the years people have had some version of this, but I think there's six things. So it's either you're helping someone save time, make money, save money, make them feel something. So whether that's like entertaining them, making them laugh, telling a great story, maybe even make them cry at some points and then being able to, if you can combine multiples of those, like that is where the gold is. So I took these long deep dive articles. I'm like saving people time of having to go through and research the whole thing themselves. But they're also learning something, which is the fifth one I didn't mention. And then I think those two are good. And it's also unique. If you can combine multiples of those. That is really where the magic happens.

[Darrell Vesterfeldt]

Okay, so say those again really quickly. It was feel something.

[Chanel]

Yeah. So it is make money, make money, save money, save time, make them feel something, teach them something, or speed to market. Which is just like you are the first one to talk about this thing now. A lot of people tend to try and do that last one by itself. I don't think that works. If you're not going to help them with any of the other ones. Like it's still going to fall flat. So I think you need to combine multiples of those.

[Darrell Vesterfeldt]

Yeah, that's really good. Super, super clear. That was, that was the number one question. People are like, okay, so what is, what is valuable content? This is where empathy becomes a superpower again. It's like, I think something that I often think about Chanel is like, does this even jump over the bar of something that you would read and I can't tell you the number of creators who I know are sending newsletters that they wouldn't even read themselves. So why are you sending it out if you wouldn't even read it yourself? Why are you sending it out to a bunch of other people? It's like, that has to be a framework of like, is this even interesting to me? Would I even read this? Would I be interested in this?

[Chanel]

Totally.

[Darrell Vesterfeldt]

It's actually the lowest bar you possibly could set for yourself, even before you kind of get into that framework. Make money, save money, save time, make them feel something, teach them something, or speed to market.

[Chanel]

If you're bored with your own content, like, it comes through so obviously on the other side of the computer screen, everyone else is gonna know you're bored. They're gonna stop reading it. And the whole name of this game is trust. If you have built trust and then you all of a sudd deplete it, that is really hard to gain back. Please take the time and focus on this stuff. It is like the most important thing above growth tactics, I will say, because again, it just makes everything else work better.

[Darrell Vesterfeldt]

Okay, so interesting contents. Thing one, what else have you learned from the most successful newsletters?

[Chanel]

They're part of communities or they've built relationships. And I'm not just saying that because this is like a mighty thing. This is probably the. One of the other keys to the whole thing is like, you have found your group of people. You are talking every week, you are sharing ideas, you're just being empathetic towards the other person's journey. Like, this stuff is so hard to do on your own. And if you can find other people to collaborate with on the growth side or even just talk through the bad times, the good times, it's going to make a huge difference. But collaborations are a huge part of growth.

[Darrell Vesterfeldt]

How have you done that? Okay, first of all, I just saw you two weeks ago in Idaho.

[Chanel]

Yes.

[Darrell Vesterfeldt]

And so, like, I know that you, like go to events and I've met you at events before, but like, how are you actually building those relationships and building that community?

[Chanel]

Yeah. So before I actually started this newsletter, I was in Jay Clouse's lab. I'm still in his lab community, which he had an in real life event on the front of crafting commerce. So that was fun. It was like two events in one. So I was part of that, which was great. But honestly, I was just lurking. I didn't have anything that I felt worth sharing, but I knew Jay's content was good. I trusted him. So I joined and even now I am in a mastermind with five other people that I met through Jay's community. And we've been in the same group for probably two years now. So masterminds are a big piece. That too. So that was like the beginning of my community journey, if you will. And since then I've just started reaching out to other folks. I met Caitlin Burgoyne because I replied to her newsletter and then she followed me on Twitter. And then we've had this relationship. Now it's really cool to see. So it's just the small things that you don't see that might happen in the DMs or something like that.

[Darrell Vesterfeldt]

So finding your community, creating incredible content, what are the secrets? Tell us all the secrets of the best newsletters out there.

[Chanel]

Still on that second piece with the relationships, I think most of the growth levers I've seen sustainably work over time just come off the back of collaboration. So whether it's putting together a summit like this, or you're doing a cross promotion and you're sharing each other's work in their newsletters, or you're doing like a podcast guesting or you're writing a guest post, like, that's still a version of collaborations. And I think those are the backbone of a lot of newsletter growth.

[Darrell Vesterfeldt]

Yeah, I've seen that be true as well. The folks who I've known who have built their brands or their newsletters just buying ads or buying their subscribers, they're never as powerful as the ones that are built in collaboration with other creators or with other people. This kind of event is the kind of event where you can do collaborations really easily. It's part of the reason that we do it. So this is like us practicing what we talk about a little bit and creating collaborations this way as well.

[Chanel]

And you can get really creative with them. Like, I recently did a 30 days of growth where I did 30 collaborations in 30 days. Every day I had a new creator come in and share one of their biggest growth tactics. And so I would share that out to this pop up daily newsletter that I launched. It was kind of like a summit, but as a newsletter, if you will.

[Darrell Vesterfeldt]

This has always existed. When I was blogging in like 2007, 8, 9, we used to do this thing where we would repost each other's blog posts on our sites. And this is like collaboration. And this type of thing is massive if you think about it. If you just break it down to its lowest common denominator, there's an audience of people who I know are already engaged, who are not my audience. And if we can tell our audiences about each other, like, these are people who are already engaged, they're already subscribed, especially in the same medium. And so they're going to be highly qualified to be engaging in my content if it's complimentary or if it's similar, but not exactly the same. And that makes a lot of sense. If I'm just posting out an ad on YouTube or Facebook or Instagram, the person's random and they weren't even necessarily searching for what I was talking about. I just interrupted their day and in the middle of their feed, and then they showed up. And so I think collaboration is a massive part of success of your newsletter.

[Chanel]

Yeah. And I think a lot of people, when they're growing something from the beginning, they're like, I'm just gonna immediately go to ads. And I'm like, that is the biggest mistake you can make, in my opinion. I think if you can't get to, let's say, a thousand subscribers organically of just like putting in the work, figuring out what your audience wants to read, figuring out, like, who they are, you should not be running ads. I feel like it's a waste of money until you hit that, like, bare minimum point. I don't think it's a good. A good call.

[Darrell Vesterfeldt]

Yep, I agree with that. Okay, so collaborations.

[Chanel]

Yeah.

[Darrell Vesterfeldt]

Great content.

[Chanel]

And then the last one I would say is like, focus, slash, time. This stuff just takes time. You can't. Even if you got magically lucky tomorrow and you went viral and you ended up with 40,000 subscribers on your email list, it's still going to take time for you to build trust with those people. Like, it's not like this stuff just comes overnight. If you look back at any of the top creators you follow now, most of them, I would say 99.99% of them have been at this for like five plus years in some capacity. There are people who grow newsletters faster, but again, if you go back to the years before that, they've been in the space, they've been doing this stuff.

[Darrell Vesterfeldt]

I think the. So you're saying that the secret is. There's no secret.

[Chanel]

The secret is there's no secret.

[Darrell Vesterfeldt]

There's no shortcuts. Like, I'm looking for the hack, I'm looking for the. I'm looking for the hack, I'm looking for the shortcut. You're saying that doesn't exist?

[Chanel]

No, not exactly.

[Darrell Vesterfeldt]

I think you said something here that's really important is that I think you didn't say these exact words, but trust is the foundation for building a great business. And the way that you build trust is. One of the key elements of trust is time. Right. And consistency. Tell me about the consistency piece of it. So a lot of questions are coming up about, okay, so how frequently am I emailing? Do I have to do it every single day? Can I do it just once a month? What have you learned? Is the right frequency for consistency to exist, for building trust?

[Chanel]

Yeah, that's a good question. I think it does depend. But I would say most of the time weekly is great. Daily is very hard, and if you can't sustain that, I would start small. Uh, maybe you move up to daily if you really want to get there, but that's a very hard barrier to, to keep yourself at. So I would start weekly if you can. If you can only do two, two times a month, that's fine too. But have the goal of getting to weekly. There are daily newsletters obviously that do well, but you have to remember, like, every time you send a newsletter, you're going to be getting unsubscribers. So you have to like continuously grow a little faster if you're going to be publishing daily. You will have a more engaged audience. Though I will say a lot of daily newsletters have like that core foundation of people that stick around.

[Darrell Vesterfeldt]

I have a friend who's been sending a daily newsletter for like 20 something years. And the level of, first of all, he has like 30 staff writers. So I'll like, this is not for everybody. And he's built this over a long period of time. But the amount of engagement that he has on a large list is insane. But it's because he's built up that repetition. He has the ability to send out really valuable content on a daily basis. And by the way, like, I'm not a daily newsletter person. I can't even, I can't even keep track of that myself. So it's not for everybody. But that's, that's a pretty intense thing. If you have to start slower, you can but try to try to ramp.

[Chanel]

Up or at least like, maybe you write a few additions before you launch and to get yourself like, to a place. However, I don't like giving that advice all the time because I think people will take that and they'll be like, oh, well, then I have to get to 50 editions before I send one. And I'm like, that's not a good move either because maybe your readers don't enjoy what you're writing and you need to get that feedback loop as well. So maybe get like three weeks ahead and then start publishing, but I wouldn't build too big of a ramp for you.

[Darrell Vesterfeldt]

Okay, I like that. That feels like a very practical. Getting started is having three weeks of content. How do I decide? Or how do I get that first thousand? Like, talk me through the mechanisms of getting to that first thousand subscribers. You said, like, do that organically. You do that naturally. Like, what should I be doing from zero to a thousand? Or if I'm not to a thousand subscribers, at which I would bet there's quite a few folks in the room who haven't gone to that point yet. How should I be thinking about growing my newsletter at that point?

[Chanel]

Let's get practical. I would say pick one social media platform and go there first if you can. You don't necessarily have to be posting on social, but start engaging with other people. This is what I did in the early days. I was commenting on other people's posts and just like, they would then go to my profile. If they were interested, they would subscribe. And, you know, I get one subscriber a day or something like that. And it's super slow in the beginning and it's going to feel frustrating. But just remember, like, one subscriber is a whole person reading your newsletter. And those people in the early days, a lot of them will stick with you over time. So, like, just. It's okay. But I would say start engaging on other people's content. Start posting eventually, but I would start engaging if you can get a couple of articles or issues published and then reach out to someone in the space and start building a relationship with them. Being able to then reach out, like months later and say, like, hey, do you want to do a cross promotion? Like, that's going to start helping you build that feedback loop and that flywheel of getting other people on there. As much as I don't love social media, it's an easier way to get started if you're willing to do it.

[Darrell Vesterfeldt]

Let's talk about the collaboration thing for a little bit, because I have talked about collaborations a lot in my career and there's a ton of objections that come up.

[Chanel]

Yes.

[Darrell Vesterfeldt]

And it's like all of a sudden it's like people forget, like, how to, like, build relationships and they're like, well, I don't even know what to do. So let's break this down to some of the common denominators of, like, if you're getting started or when you are getting started. What are some of the collaboration types that you did and kind of like walk us through step by step, exactly how you would approach a collaboration.

[Chanel]

Totally. I think the easiest thing for newsletter creators is a cross promotion to start. I won't say they're the most effective, but they're the easiest to start getting like the wheel spinning. I would say go to other newsletters in your space or maybe social media and find other creators there and just reach out and say like, hey, I would love to do a cross promotion. Like, here's what I write about that kind of thing. You can also take the approach of like sharing a lead magnet that you've built with them and saying like, hey, I know that you know, I teach personal finance for moms or something. Go to other people who are talking, maybe it's like a recipe blog or something and say like, hey, I have this thing about how moms can do personal finance better. If you go to them and say like, hey, I have this 10 part checklist of like 10 things you could do to improve your finances by tomorrow. And go to that person and say like, you don't write about this, but I know your audience wouldn't be interested. And just offer that up to their audience for free. They share it with their audience and then some of those people come over and join your list. So it's like those small things in the beginning, but they can have a big impact.

[Darrell Vesterfeldt]

So a lot of people, I'm. I'm guessing this is like triggering a lot of like the ick for people. Like I've gotta like ask people to do this. Like, yes, like get like, how did you like mentally overcome that or emotionally overcome making that ask? Cause I think again, it's actually pretty simple when you start breaking it down to the steps here. But it's simple and people just don't do it. Like, what's your advice for people who are just getting stuck? They're not doing it. They're afraid to do it. They are afraid. Maybe I'm too small. I can't make this ask yet. What, what are some advice for like the mental and emotional barriers that we might hit doing this?

[Chanel]

I feel you. And I think that's one of the reasons that I went so deep in my research, because I knew it was good because I spent so much time doing it that I wasn't, I didn't have any like qualms about sharing it. But if you know what you're talking about is important and it's going to help at least one person I think you almost have like an obligation to try and grow your audience and help help those people, but you can do it like in private. So if you subscribe to the person's newsletter who you're going to ask for, you know, to do a cross promotion with, once they send out a newsletter, just reply and be like, hey, really enjoying your newsletter. I have this thing wondering if your audience would like it. What do you think? And if they don't answer, it's okay. Maybe they're busy, maybe it got lost, Maybe it was a no, that's all right. Just do it again. And like, don't let that make you feel any less about yourself. Your content's still important, it's still going to help someone, but it's just maybe not that audience right now.

[Darrell Vesterfeldt]

Yeah, I think the hard truth here is you're probably not ready to grow your business until you're ready to have the courage to make these kind of asks in your business. And I think at some point, like, there's a balance of pain, like, which pain you'd rather have. Like the pain of doing uncomfortable things and making ask for collaborations or asking people to sign up for what you're doing or the pain of not having a business that's sustainable. And I think it's like, it sounds like I've been there before. And it sounds like that's kind of where you got where it's like, okay, this is uncomfortable. But like, I want this to succeed so bad that I'm willing to do this uncomfortable thing even though it's uncomfortable because I know that it works and it's going, it's going to make my business grow. And that's a larger priority than my comfort or discomfort in this moment.

[Chanel]

Yeah, I think in the early days I was thinking of it more of like a game so that I wouldn't associate my own like self worth to how many subscribers I had. But if I'm like, oh, I had five today and tomorrow I have six, it's like, not about me anymore. It's about that number. I don't think that's a good healthy strategy long term. But in the beginning it can really help you do that.

[Darrell Vesterfeldt]

Well, it helps you take it not so serious or not not take yourself so serious along the way too. If you're playing a game, it feels more fun. And by the way, the point of a game is it's supposed to be fun. So if you can make fun out of it too, it helps.

[Chanel]

So yeah, yeah, totally.

[Darrell Vesterfeldt]

How many no's do you Think you heard to every yes that you heard when you were asking for collaborations?

[Chanel]

I would say probably 75% yeses. So there, there were definitely some no's or like just ghosts, like I never heard back, which is fine. I don't know. I think there is always going to be a no. And maybe it's because there's this thing where if a creator has been around for two plus years, three plus years, however long, and they see you just coming into the space, they're like, is this person going to be around in six months? Like, am I going to put my name on the line just because they want to do this thing? So some, some people are more close to the chest with actually doing those collaborations, but if you let the time happen and you keep going with this stuff, over time, you're going to get more people reaching out to you to do these things because they see that you're consistent and you're going to be around. So that's a big piece of it too.

[Darrell Vesterfeldt]

Okay, so collaborations. Okay, so going from zero to a thousand, it's consistency, it's asking for collaborations and doing collaborations. What else should we be thinking about? From going from zero to a thousand subscribers?

[Chanel]

I would say refining your content, making sure it's actually something people want to read. Making sure it's something you want to read. Like if someone had sent that to you, are you interested?

[Darrell Vesterfeldt]

Exactly.

[Chanel]

And some of those early folk, the early readers, they're probably going to give you some decent advice, you might hear some bad advice. So it's kind of a tricky balance to not listen to everything, but if you start hearing something multiple times, it could be something that you can pay attention to.

[Darrell Vesterfeldt]

That's a good one. Let's double tap into that because I think I've seen both of these things happen. So thing one is, I'm super passionate about this thing, but if I'm objective about it, it's kind of boring and people don't really like it. And I see people spend years and years and years and they're being true to themselves, they're being authentic, but the content's just not that good or it's not really connecting to people, or I see people who are listening to every single piece of feedback and they're switching up too often and the reason they're not growing is because it's like for six months it was this and then for three months it was that. And for like, then I stopped doing it because I was sad or upset that I wasn't getting the feedback. I Wanted. Talk to me about the recipe here for success of, like, honing my content, staying true to myself, and then finding the level of consistency to really see this thing through. Like, how do you think about those three things which feel like maybe they're pulling in different directions all the time?

[Chanel]

That's a good question. It's a hard answer because on one hand I could say, if you're super passionate about this thing and nobody's enjoying it, you probably just haven't found your people yet. And there's truth to that in a lot of cases. But there's also, like, a marketing angle and, like, maybe you're just not positioning it right. And so once people get in there, they understand and they love it. But you're not able to grow as fast because you're not able to explain it well on the outside. But I think there is something to be said about, like, again, if you're passionate about this thing and then all of a sudden you start making these changes that end up with you hating what you're doing, like, that's going to carry through, through the screen. Like, there is something about energy and like, the way people can understand how much is coming through. So it's a tricky balance. And I would say don't change too much, especially if you have something decent going. But if you don't have something decent going, maybe try some minor changes and see if they hit, and if not, then don't do them again.

[Darrell Vesterfeldt]

I think that this is, like, these are the real questions that I want to be asking people, because the real challenges that people have here is like, how do I know this is even good? Yeah, how do I know this is worth doing? And how do I keep going when it feels like it's not working and I'm spending a lot of time doing this thing that just isn't seeing results? And so it's like knowing the balance between, like, do I keep going on this thing and I just haven't found my people yet, or is my content just not good and I need to adjust and change? I think that's the real question that I feel like a lot of people struggle with. And I, I'm curious to, To. To dive into that a little bit deeper.

[Chanel]

Yeah, I, I'm always a big fan of, like, paying attention to how many replies you get to something, especially when you're not asking for a reply. So if you put out a piece and, like, you really put your heart and soul into it and you got a couple replies, like, that's a good sign. It's not easy to get replies, but yeah, I think paying attention to replies, see what people say, are people sharing it with others? Like, one of my favorite questions to ask in my welcome email is, where did you hear about this? And I often find, like, people like, these little pockets of the Internet will start, like sharing some of these articles. And I'm like, oh, this is awesome. You can kind of like pay attention to those signals as well. But it's again, it's hard because it's not like quantitative data. Like, you're not going to be able to go into Google Analytics and like, see exactly where every person came from. You can get some of that, but not a ton.

[Darrell Vesterfeldt]

We've got lots and lots and lots of practical questions that are coming up. And so I want to just kind of go through a round of these questions and see where it takes us. But we've talked about consistency and you're saying weekly is probably like the right rhythm to get started with. What about what day of the week to send it on? Is there a day of the week that's better or not to send your newsletter?

[Chanel]

I think there's so many articles, if you Google what day of the week to send newsletter, you could probably find some pocket of day of the week that's best. But honestly, like, I sent mine on a Sunday because that's when I finished the article and I was like, okay, I'm just gonna hit send.

[Darrell Vesterfeldt]

So I think this is one of those check engine like questions too that I'll say. And this is, this is not to throw shade at anybody who's asking this question. But it's like, sometimes we ask a lot of questions that don't actually matter a whole lot to stop us from actually doing the work. And some of the most successful newsletters and the successful people I know who have large newsletters are like, send on Monday. And then I have people who have equally large audiences, like, never send on Monday. And it's like, okay, that just proves that because you can, you can Google this answer and get like, probably all seven days of the week is the right answer. Just do it when what makes sense for you. I think the more important thing here is like creating the rhythm of consistency for yourself. And so for you it's like, Sunday, okay, I'm done. Great. Hit send. And creating that consistency and creating a system for you to be consistent on that day, I think that's more important than what actual day of the week you send it on.

[Chanel]

Yeah. And I sometimes kick myself for choosing Sundays because I'm a natural procrastinator. So Saturday rolls around, I'm like, oh, now I really have to finish this thing. It doesn't really work out well for personal things.

[Darrell Vesterfeldt]

So, yeah, Mike, Mike's question is, what should I wear while I'm writing my newsletter? Okay, so it doesn't matter what day. What about what time? What time of day? Morning, afternoon, evening, midnight, 2am Is that another one of these questions or does it actually matter what time we're sending our newsletters?

[Chanel]

I think it might matter more than the day, just because if you're naturally like trying to speak to people who live in North America or like on the east coast or something, it's probably a good idea to send it like in the morning or early afternoon versus like midnight because it's going to get buried by the time they wake up. So I would say during the day of the time of the people you want to reach, but there's not like a 7am versus 8am is better. Although again, there probably is data to back up multiple times. So I would just say like a reasonable hour for people who are in your audience. But if you're like speaking to gamers who are up until 2 in the morning, like, it probably doesn't matter. You could probably send it at midnight and that's a better time than others.

[Darrell Vesterfeldt]

So, yeah, that's good. Okay, we keep getting this question a lot. What platforms do you think are best for. For sending newsletters? And I'll put, especially if you're just getting started and you're trying to grow to a thousand subscribers, which one or which ones do you think are best?

[Chanel]

I think it depends if you have a website or not. If you don't have a website, I'd probably start with a substack or a beehive just because it's easier. Kit is getting to a place where it's working with like landing pages and stuff. But I still don't think it's great yet. However, if you have a website, I love Kit. It's like, that's what I use. But yeah, if you don't have a website, I would say the other one of the others is a great place to start.

[Darrell Vesterfeldt]

Awesome. The next biggest question in consistency is what do I write about? And so historically somebody was asking about content pillars. Is that a thing? Do you think about content pillars or do you like, just have one thing that you talk about all the time? How do I know what to write? Because writing a newsletter, 52 newsletters a year, if I'm doing Weekly. It's a lot of newsletters. So how do you think about what to write? How are you ideating? How are you creating a list of ideas? Are you thinking about pillars? Or are you just kind of doing one thing over and over again?

[Chanel]

Yeah, I'm still really not thinking about pillars, but for me it was just like, okay, I have to pick a new person and then I just research that person. But it's the same concept. Like, it's still, how did they grow their email list? How do they grow their audience? So I think it depends on the topic and like what you're doing. Like, if you're a service business owner and you're trying to grow a smaller email list just to keep potential clients interested, I think maybe a content pillar strategy could work well of like, here are the three big things that I talk about. And then there's smaller topics on the bottom of that. If you're just getting started and you are just picking a topic out of thin air that you're hoping is going to be like your thing, I would say sit down, create a empty Google Doc and try and hit 30 bullet points of topics you can write about. And if you can't get to 30, it might be a sign that maybe it's not the right thing for you. But if you're going to have to write 52 in a year, getting to 30 should be kind of easy. Just remember that's going to be a hard exercise over time, you will come up with more ideas just naturally as you're writing these things. If you can't hit 30 exactly, it's okay. But try and get close to that.

[Darrell Vesterfeldt]

I love that. That's a piece of advice I've never heard before. Whatever your topic is, sit down. And if you have 30, if you can't even get to 30 ideas, like, it may be the not the right thing for you. Like, that feels super practical. And this is a case where AI is actually not your friend because AI could cause you to get really lazy and AI could give you 50 ideas in three seconds. But if you don't actually have the passion or the understanding or the empathy to write 30 ideas down about whatever the topic is, that that maybe is a good telltale of why you should maybe choose something else or go a different direction.

[Chanel]

Yeah, and I think that exercise can also help you distill like the actual topic. So maybe you're thinking of like these big chunks of topics. But as you start writing that list of 30, you realize like, oh wait, that one is actually five different articles that I could write. And so then you have like a little series that you could write. And so I think it could help you actually formulate your topic better.

[Darrell Vesterfeldt]

Yeah, and the other thing I'll say is just keep going. We have a mutual friend, Matt, and this was on YouTube, not on his newsletter. But it was like he was writing about productivity. Was. Was his whole thing. And it was like lots about productivity, lots about productivity, lots of productivity. And then he did something on the bullet journal and it took off. It was like went crazy. It was like, oh, like I found like as I'm writing, I'm actually finding out like what's resonating with people and what's not resonating with people. And it's like sometimes it takes you doing the work and having responses and getting replies or the lack of replies and that helps you kind of hone in the content and what to write about along the way.

[Chanel]

Yes, totally. Matt's great. I'm glad he found his. His little niche there.

[Darrell Vesterfeldt]

Same, same, same thing. So your newsletter is free?

[Chanel]

Yes.

[Darrell Vesterfeldt]

And monetizing a newsletter a couple of different ways, but talk to us about how you like or first of all, why newsletter? And then how to monetize it as, as like as you're trying to sustain this long term. But what ways are you monetizing?

[Chanel]

Yeah, why a newsletter? Like it just in general for people. I just, I mean email is just like the. It's never going to end. People have been saying email's been dead since like the day came out. So I just think it's going to morph, it's going to change. But there is something awesome about being able to just like send an email to a friend or send an email to 40, 000 people and be like, hey, saw this thing this week. I really enjoyed it. Thought you would too. You actually land in people's inboxes. And aside from other places like Instagram or even YouTube, like you might have 40, 000 followers, but only like 02% of them will see that post, which is very frustrating. As someone who's creating these long form pieces, I would say email is just like a pillar.

[Darrell Vesterfeldt]

One more, I'll say here, you mentioned this. I'm double click into this, which is like owned versus borrowed. I think this is super huge. I know a lot of people who have spent so much time building their social channels and I think there's a place for that. But at the end of the day, if email not changing an algorithm where only 10% or 5% or 2% of people are seeing the emails that you send out. It's going directly into somebody's inbox so you can communicate with somebody. And no matter what changes happen in email, you still have the ability for somebody to see it. The other thing I think is a low key that not a lot of people talk about is social media is often seen as a communication form of one to many. Email can be written one to one. Even though you might send it to 40,000 people, you're communicating from me to this one person's inbox. And so it's one to one, even though you're sending it out in mass, it's a one to one communication. And so you can just communicate at a more personal level than you can on social or other platforms. And I think that one to one connection actually creates a foundation of trust that I think is super important.

[Chanel]

And there's a thing where Justin Walsh had this huge audience on LinkedIn, right. He had hundreds of thousands of followers and he was getting great engagement. And then one day he went to log into his LinkedIn account and it was gone. He couldn't open his account. So he actually started a newsletter right after that and diversified over to Twitter. So he realized that pretty quickly. But you just don't have control over that with email. You could take your list and download it from kit and go somewhere else. But yeah, you can't really do that with threads or Instagram or anything like that.

[Darrell Vesterfeldt]

Okay, so monetizing. So that's the why of the newsletter. Why that is a thing.

[Chanel]

Yeah.

[Darrell Vesterfeldt]

So monetization. And you do it a couple different ways, but talk to me about how you want to monetize.

[Chanel]

Yeah. So I mentioned sponsorships before. Affiliates are great. I naturally write about creators who might have a course. So I'm like, I'm going to talk about this course anyway. I might as well sign up for their affiliate program. So that's adds a little bit into the revenue mix. And then last August, I also launched a community for other folks growing a newsletter. So that's been the bigger piece as well.

[Darrell Vesterfeldt]

Yeah, and that's what I love. It's like when you have this owned audience, it's like you can do sponsorships. That's a great way to get started. It's really low lift. But then like creating things that are yours and you own is really great. So it's like, I think you started the exact right progression, which was like, all right, sponsorship's really low lift. All I have to do is like have the audience and People pay me money and then it's like affiliates as I can sell other people's stuff and make money from it. And then it's like, now I can own my own thing. And we're going to talk to Jeff Walker tomorrow and Jeff's one of my online business heroes and he talked about like, this is a thing that's been in my mind for years and years and years. It's when you have an email list, it's kind of like a money printing machine because you've just got to ask them what they want and need and you got to go make it for them and give it to them.

[Chanel]

Yeah.

[Darrell Vesterfeldt]

And it's like just doing that over and over and again. Like that is such a sustainable, defensible business when you have an audience in email form in that way, baby. Cuz just ask them what they need and then go give it to them. And you can do that over and over again. It's such an easy way to monetize your audience is basically just serving people. All right, we've got a couple minutes left. What have we not talked about that feels really important when we're thinking about newsletters? What haven't we. We broached it that you feel like is really important for us to hit on.

[Chanel]

I think I'll just come back to creating good content. Like it just does not go out of style. This is like going to be. As AI gets even more and more ingrained into everything we do do, it's going to be the way that you can stand out, like, period. I think if there are so many people who are looking to just build audiences and you know, send out like a curated list of links that AI put together for me this morning. Like you have to be able to stand out and create something unique that other people are interested in and are going to keep reading. So I don't know. I will harp on that until the day that I die. I think.

[Darrell Vesterfeldt]

Yeah, like laying in bed tonight thinking about 30 hours for a newsletter, you've got to create something that is worthwhile for somebody. This is something that the mighty founder Gina talks about often is. Like so much stuff in this world is generic. And like we try to be so allergic to generic. If you are not even wanting to read your own newsletter, that's the first red flag. If you're not even looking at your content, reading your own newsletter, if you wouldn't even read it, that's step number one. I just think creating compelling content is the basis for all of it. And what a waste of time and energy and, like, attention. If you're spending all this time writing a newsletter that, like, isn't even interesting to you, and if it's not interesting to you and you care as much as you do, how is it possibly going to be interesting to other people?

[Chanel]

Totally. I saw someone asked if you can just send out like a video in your email of you talking. I think that can work. I think you can also transcribe that video and turn it into like a short blog post as well. I recently launched a podcast and I'm learning that podcast folks and newsletter folks are not necessarily the same people. So I've been taking transcripts of the podcast and turning it into a blog post. And a lot of folks actually really prefer the blog post version, which is super interesting. So I would do both if you can.

[Darrell Vesterfeldt]

Well, Chanel, thank you so much for your time today.

[Chanel]

It's.