Discover how the best media brands and solo operators are winning at newsletter growth & monetization.
Hosted by SparkLoop's cofounder Louis Nicholls and SparkLoop's newsletter nerd, Dylan Redekop—we take you behind the scenes and share the strategies, trends, and tactics you need to know to build your email audience and revenue.
Featuring exclusive interviews with the smartest media experts and operators out there today. Including from the Hustle, Morning Brew, Workweek, The Pour Over, and more.
S+G Sam Klemens
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Dylan Redekop: [00:00:00] Welcome to the Send and Grow podcast. I'm your host, Dylan Redikov. In my day job at Sparkloop, I spent all my time analyzing how the best newsletter operators and media brands in the world grow and monetize their audiences. I get a behind the scenes look at how they're growing their newsletters and driving revenue.
And there is so much to learn from their success and from their mistakes. With this podcast, you get that access too. Every week, I sit down with a different guest from industry experts to successful operators. And we go deep on the stuff that you need to know about, so you can become really effective at growing and monetizing your newsletter.
Today, I'm joined on the podcast by Sam Clemons. Sam is the founder of The Rollup Newsletter, a finance newsletter he started less than a year ago. Since starting, he's grown The Rollup to over 14, 000 readers. In this episode, we discuss Sam's exact strategy behind The Rollup's rapid growth, his strategy for unique content subscribers will actually read.
And how he's been increasing revenue every month. [00:01:00] Sam, thanks for joining me today. Why don't you start by telling us about you and the rollup?
Sam Klemens: Well, I'm Sam. I write the rollup and it's an investing newsletter that shares content from outside of the mainstream media. So a lot of the other finance newsletters share articles from like CNBC or the wall street journal or Yahoo finance, that type of thing.
But my newsletter only shares content from places like sub stack or YouTube or Twitter or. Other alternative media sources. So it's for people who are interested in getting a different perspective on the markets and don't want to read the mainstream ideas.
Dylan Redekop: Nice. And do you have a finance background or anything like that?
Or how did you get started with that sort of as a
Sam Klemens: topic? No, I don't have a finance background. I, um, got interested in investing about six or seven years ago, and I started really going down that path and learning a lot. And then I actually made some money from investing, which really got me hooked on it.
And in fact, I'm, I'm using some [00:02:00] of that money now to fund growth for the rollup. So investing in finance, these are two topics that I'm really interested in and they've benefited me. So that's, that's how I got into this writing about it. Cool. So
Dylan Redekop: you could say you, you know, kind of pulled on that thread of curiosity in that sort of, in this realm of finance and next thing, you know, you're writing a newsletter about it.
Can you talk to us about some of the content we'll find in the newsletter and also like how your newsletter is growing in terms of, I guess, when you started to where you are now in terms of like subscribers?
Sam Klemens: Yeah. So some of the content it's, I could think of it as the best articles that I find on Substack or.
From other research places. I share a lot of research reports, lots of different people put out investing reports, and I share those. And that's really the, the meat and bones of the rollup. Um, in terms of subscribers, well, I started from zero. I had none about a year ago. I have another newsletter on Substack, [00:03:00] and so that was more of my personal blog, and then every couple weeks I would share the best articles that I was finding, and at a certain point it made sense to split that section of my newsletter out into its own thing, and that became the roll up.
I had 200 subscribers at the point where I transitioned from Substack to Beehive. And I'm at... 14, 000 right now. Do you
Dylan Redekop: run the roll up full time? Is that kind of your,
Sam Klemens: yeah, yeah, that's, that's all I do. And it is a, it is a full time job between the roll up and my other newsletter. It is totally a full time job.
So if you're thinking about starting a newsletter, you have to account for how much time it's going to take and how much time it's going to take to do it well, because it's, it's demanding. And
Dylan Redekop: I think you probably agree that the number of newsletters over the past few years has just kind of You know, 100 X out there, the opportunity with different platforms that have come out of democratize, you know, the, the ability for people to create a newsletter.
So I think it's really important [00:04:00] to, like you said, put that time in. Create that really high value, good quality content that people are actually going to want to read as opposed to, you know, whipping up a newsletter and just, you know, putting a little bit effort in here and there, it's really not going to get you too far these days.
It's not
Sam Klemens: going to get you too far. And I look at a lot of newsletters and a lot of them don't stand out. A lot of them have the same themes, talk about the same ideas, talk about the same content. And so if you're going to do this, you have to find a way to stand out and be different than the other.
Newsletters out there because there, there are a lot, there are more than you even think.
Dylan Redekop: Yeah. And I was going to talk about the general content that you're sharing and how you are being unique later on in the interview. But why don't we jump into that a little bit right now? I noticed you, you do post, I think you start off at least the, all the additions I saw, you started off your newsletter with some memes.
So you You inflect, um, you inject, I should say humor almost right off the hop, uh, which for a, [00:05:00] you know, investing finance style newsletter isn't maybe not quite as common. So can you walk me through how you decide what to include for content, you know, why you went down that path of, of the humor and talk me through that a bit.
Sam Klemens: Well, people like memes. I like memes. They're funny. They get people to open the newsletter because they know there's a meme right at the top there. So that's important. And this is. Part of that is just me injecting my own personality into this thing. I'm not trying to be, there are, there are other newsletters that are catered to like ultimate finance professionals that are very strict and by the books.
And that's, that's just not what I'm doing. I'm interested in a lot of different things. I share different content here. I like, I like memes. So I share that. And. Part of that meme thing is that's that's a strategy that I picked up at some point I saw another newsletter doing that and I noticed that I would open that newsletter because I knew that there would be memes in there I wanted to see them So I said I'm gonna start doing that and a [00:06:00] lot of what you see in the roll up right now is Stuff that I picked up from other newsletters anytime.
I would notice something cool in another newsletter that I liked reading I would steal that For example, every Sunday, I'm, I started sharing an insider trade from the stock markets. That's something I saw in another newsletter last month and I started doing that. So I'm always, I'm always looking for new things to add that I think would be interesting for my readers.
I
Dylan Redekop: guess when you add something new, do you have any way of sourcing feedback or soliciting feedback from it? Or are there specific metrics you check to see if, you know, people are liking that or if it's working at all? I would say
Sam Klemens: that's maybe a bit of a weak point. Don't have a way to check that. I do polling occasionally on the roll up, but I don't, I don't have a specific way to check that other than sometimes I will talk to people who read my newsletter and I have, I've gotten feedback about the memes.
People like that. So I keep that in there. That's definitely a thing. That's good to go. Awesome.
Dylan Redekop: And I noticed you're sharing as [00:07:00] well, like an AI image of the week as well. Which is not necessarily anything to do with finance, but something interesting that's again, is that an example of you pulling on your curiosity?
Sam Klemens: Yeah, that's just something I'm interested in. You know, we take it for granted for now, but mid journey and these AI programs only came out like eight months ago. And when they came out, I was super stoked on them. I love them. I thought the images they were creating were so cool. And I was going through and finding all of these images and I just wanted to share some of my favorites.
So I started putting it in there and yeah, I think. I can't empirically prove this, but I think that's been a good one because I've noticed that I get a lot of link clicks at the bottom of my newsletter, stuff that I put down there, people are really seeing. And so I'm, I think it helps to get them to scroll down to the bottom to see what's down
Dylan Redekop: there.
Yeah, that's a, that's a good strategy to get the. The read through for sure. I've seen other people employ similar, similar tactics. So we talked about a little bit about your journey. You're at 14, 000 subscribers now. What are your open rates and, and how are those looking? I, [00:08:00] because we'll, we'll get into, you know, revenue in a little bit, but, um, let's talk about what your open rates are lately.
Yeah. So
Sam Klemens: my open rate is about. 59 to 60 percent right now, but I don't pay a lot of attention to the open rate because as I'm sure, you know, the Apple privacy, Apple mail privacy protection really distorts that figure now. And for people not familiar with that, anyone using an iPhone, the iPhone will automatically open the email.
Even if the person doesn't open it in their inbox. And so this can massively distort your open rates. So I think, I think that there should be a bare minimum open rate you should have. You should have at least probably 50 percent in this environment. But beyond that, I don't pay a huge amount of attention
Dylan Redekop: to it.
That makes sense. In terms of metrics, is there one that you pay more attention to than any
Sam Klemens: others? Yeah, just the click through rate and number of clicks. And I'm always trying to get that higher because [00:09:00] that's that's how I measure engagement in my newsletter is the link clicks.
Dylan Redekop: Yeah, absolutely. Let's get into a little bit more about growth strategy.
So you had mentioned earlier you transitioned. From kind of a blog on Substack over to your current setup on Beehive. Can you run me through how many subscribers you had again there and then how you've gone from, you know, in a year from basically like, you know, a couple hundred to over 14, 000. What was the process like to get, you know, those first few hundred and then, you know, to get your first
Sam Klemens: thousand?
Getting the first few hundred was some of the hardest work I've ever done. That was really difficult. Some of the things I tried, I posted articles to Reddit that didn't really work very well. Reddit sends a lot of traffic, but very little of that actually converts into a sign up, so that didn't work. I went on Twitter and I would find posts by popular financial accounts and I would reply to every single reply in there.
Linking to one of my articles saying, hey, you like this post, you might like my [00:10:00] article. That was tons of work for not much reward. Within the Substack network, I would comment on different articles. I would leave comments below with my link, with a link to my article. And that, that was okay. And so I used all of these very non scalable methods to get to 200.
It was just, it was a lot of work, but so that's how I got to 200, 200. I transitioned to beehive and then pretty much that's at the point where I integrated with SparkLoop. Basically the reason I transitioned to beehive was so that I could work with SparkLoop and start paid growth there. And so as soon as I got hooked up with SparkLoop, I, uh, started getting 20, 50, a hundred subscribers a day.
And that's, that's been a major source of growth. It was out with a
Dylan Redekop: partner program.
Sam Klemens: Yeah, I was with the partner
Dylan Redekop: program. And so, in terms of your current growth strategy, how has it changed from, say, your first, you know, thousand, two thousand to where you are now? Are you trying new things? Are you [00:11:00] still trying things that maybe don't necessarily scale?
Or are you pretty focused on scaled
Sam Klemens: growth? Yeah, I gave up on the non scalable stuff. That was brutal. I mean, I look back on it fondly, but I never want to do that again. So yeah, I gave up on that. And also the whole thing with Twitter, uh, not linking to Substack anymore. That was a big bummer. So yeah, so I did, uh, did SparkLoop until about eight or 9, 000 subscribers.
And then I started experimenting with Twitter ads and I've used that to pick up another four or 5, 000 subscribers. And I'm also using a little bit of a partner program and a little bit of a beehive boost, but those, those are small compared to what I'm doing with Twitter ads right now.
Dylan Redekop: Got it. So that's the majority of your spend is on Twitter right now for.
For growth, is there something that you tried in terms of growth that you thought, yeah, this is going to work really well and then completely flopped or vice versa, you didn't think would work and worked really well.
Sam Klemens: Yeah. I had a, I had a huge [00:12:00] flop that happened twice. I really thought that in internal with our referral program work, as in you, you offer your subscribers a reward.
If they refer people to your newsletter. And the first time I tried this, I did kind of a standard deal, which was like, I had a mug and other stuff. I didn't even remember. I had different physical items where if you referred people, I would send it to you, drop shipping. And that totally flopped. I got two people.
I got two referrals. So that was disappointing, but I figured, you know, maybe I just don't have the brand for that. People don't really want a mug with my logo on it. Fair enough. That's fine. So I gave up on that for a little while, but then two months ago, I tried it again. And this time, so I write about finance and I had accumulated a lot of financial indicators, different financial and macro indicators that were free to use, that you could use to gauge the state of the economy and look at different [00:13:00] stuff.
And I thought this would be really interesting for my audience. I thought they would really like it. And really, I thought it would be really useful for them. And I tried this and I got one referral out of 14, 000 people. Just nobody was doing it. And so I put a lot of work into that. And so I've just, I've been completely unable to get the referral program to work.
And I don't think I'm going to try again because I just haven't been able to get it.
Dylan Redekop: Yep. That makes sense. I mean, if it, if you've tried it a few times, it's like getting blood from a stone, right? If it's not working, you just let it, let it go. Let it go. That makes sense. Maybe at some point, if there's something else that you.
Are noticing people are wanting that you could offer that might be something
Sam Klemens: you had on the verge a week or two ago, right? And they talked about a shell from the a10 warthog, I think and that see that sounds awesome That sounds super unique and hard to
Dylan Redekop: get. Yeah, that was uh, mike from the merge It was I think that's why his referral program was super successful because it was stuff that his audience was like Yes, [00:14:00] that is super cool.
I want to You know, recommend as many people as I can to get this and I can't go and buy it, you know, at the local shop or anything like that. So, yeah, it's definitely important to have those unique elements that your audience is really going to, you know, want to be interested in when it comes to referral program.
Let's move on to, to revenue. How did you earn your first, you know, newsletter dollars, if you will? Well,
Sam Klemens: I'll tell you what did not work at first. I didn't start advertising until I had 10, 000 people. And I thought, I thought that 100 sounded like a fair price to advertise to a 10, 000 person newsletter, and I naively thought that if I threw that offer out there, a lot of people would take me up on it and they did not.
I could not sell anything at 100. I think just I had no reputation as an advertiser. Nobody wanted to spend that much money on a new newsletter. So. I came across this interesting idea. Um, Anthony Castrillo, he writes body, brain and AI newsletter. And [00:15:00] so he said that he started at a ridiculously low price and then double this price every month.
So I just said, screw it. And I said, you can advertise in the rollup for 10 this month. Yeah, I know it's stupid for a 10, 000 person newsletter, but I did that. And I. Sold out that actually sold out, of course, within a few days. And so I got a bunch of feedback from that. I got people seeing that you can advertise in the rollup.
I got to see what the, what the click rates were like and the success of that. So I did 10, then I doubled it next month to 20 and I sold out. And now I am up to 50 for November and I have half sold out. I still have a few slots left at the end of the month. And so if I, if I sell out for November, that would, that would give me about 450 of revenue for the month, which is, uh, obviously not close to my goals.
This is not sustainable, but it is what I'm working on building up right now. I have no [00:16:00] experience in ad sales. This is all completely. New to me, figuring out how to do all of this. So, you know, I think someone with a business background would do it better, but I'm just, I'm learning all of this right now.
Dylan Redekop: And so what was your, what would you say your biggest learning or lesson has been just in those few months that you've been doing ad sales or trying to. Trying to sell ads in your newsletter,
Sam Klemens: biggest lesson, just, you have to, I have to reach out to a lot of people. I still think 50 to advertise in a 14, 000 subscriber newsletter is a really good deal.
I think people would pounce on that, but it's, it's still difficult. It's still salesmanship. It's still learning how to, how to present a good offer that people want to buy. And I'm just, I'm constantly working on improving that. Yep.
Dylan Redekop: That makes sense. Do you have any other streams for your newsletter? I don't
Sam Klemens: have any yet.
I, I have a vision of when I get larger, there are some things I'd like to try. I might, I might try to start doing interviews if I [00:17:00] can get some large name financial commentators once I have a large enough audience to get them interested. I might start charging a small fee for access to that. But as of right now, I don't know.
I don't have any other revenue source than just the advertising.
Dylan Redekop: Awesome. Yeah. And you've been using SparkLoop's, subscribe recommendations, widget to make paid recommendations to new subscribers too, right? Can you share how that revenue strategy has been working for you? Yeah,
Sam Klemens: it's been massive. It has been absolutely massive.
Combining Twitter ads with Upscribe and getting paid on the back end. It has been, I couldn't, I could not do Twitter advertising at the level that I'm doing it right now without Upscribe. I don't want to show the exact figures, but it covers a fair bit of my cost of advertising. And it's been, it's been excellent.
It's been excellent. If you're not using subscribe, you have to start using it. That's all. That's what I can say about that. In
Dylan Redekop: terms of the rollup, we're at a year in [00:18:00] 14,000 subscribers, we're monetizing. What is the next six months to a year look like for you? Uh, well, it's
Sam Klemens: just going full blast on Twitter advertising.
Trying to get as many people as I can to sign up. I'd really like to get to 2, 000 a month in revenue, 2, 000 a month in my mind. If I can put all of that back into the newsletter, 2, 000 a month of paid growth is a pretty decent level. And again, I'm making so much money on the back end with Upscribe that 2, 000 is, let's say I'm spending 8, 000 on Twitter ads.
I'm getting 6, 000 back. With upscribe. So spending 2000 is really like spending 8, 000 every month. So that's a, that's a lot of paid
Dylan Redekop: growth. It's definitely letting you leverage, um, those dollars to just rewrite, reinvest right into growth. So that's great. So you're looking at. Basically sinking all that in any other aspirations for more content [00:19:00] or anything like that, along with the roll up, or are you just going hard with the twice a week?
Correct? That twice a
Sam Klemens: week? Well, I am doing everything myself. So I am very hesitant to do more than twice a week. One of the things With advertising before I had advertising, I could be a bit more casual. Maybe I would publish on Tuesday or Wednesday. I wasn't, I wasn't losing sleep over it, but with advertising now I'm selling these spots in advance.
They have to go out on that day. So it's a strict schedule. So I don't. Want to over commit to anything that I can't do, but I will say that I have hired someone to just help me do the very basics. They set up the drafts, they put in the image, they helped me with a few other basic things. So that's a start.
Yeah, maybe in time, I'll give them more responsibilities so that I could. Go up to three times a week, which is obviously a super easy way to increase revenue, but with me doing a majority of the work right now, it's, it's not worth it. It's not even feasible.
Dylan Redekop: That makes sense. And we talked [00:20:00] earlier about keeping the quality at a high level, right?
Yeah. So as soon as you increase the number, the amount of content you're putting out there, it just takes up that much more time. So I think. In a lot of ways, lesser is better. Not everybody wants more emails in their inbox necessarily in terms of, you know, frequency, we want the quality, um, substance, right?
Yeah. Yeah.
Sam Klemens: I've had, yeah, I've had people say that they're say, thank you. Two times a week is perfect. That's good. I don't need more.
Dylan Redekop: That's right. I mean, and there are five day a week newsletters that do a great job and are very successful, but it's definitely not for everyone. And I think we can do a lot with a once or twice a week newsletter.
So I think you're a great example of that. I got just two more questions for you. The first one is what would be somebody who is thinking of starting up a newsletter and, you know, wants to eventually kind of make a business out of it. Like you have, what would be your biggest piece of advice, whether something to do or something not to do?
Sam Klemens: My advice would be just plan to be [00:21:00] consistent. You really have to, if you look at the commonality of every successful newsletter, there is one thing that you can say with 100 percent certainty and that's that they're still publishing today and they're still sticking with it. You don't see all of the failures.
So you have to have a plan to keep doing this week in and week out and always publish, especially when you don't feel like it, especially when it feels like. Everything is going to hell and your open rate is going down and you don't know why and nobody clicked on your last newsletter and you're totally bummed out on the whole thing.
You still just have to keep doing it. You have to have that discipline to maintain a schedule and keep publishing because it will get better. And, you know, it's a shameless plug, but get up scribe or I get the partner program and start getting some referrals in there because it feels really good to have new readers coming in.
You know, when I started 1 of the things with my non scalable growth is if I wasn't [00:22:00] doing it. There was nobody coming in and that got a little bit depressing. Whereas when you use spark loop, uh, you can have people coming in when you, you wake up and you have more subscribers and that's awesome. That's a great feeling.
So I wish I had integrated with spark loop earlier to get some subscribers in there and just get that momentum, momentum going.
Dylan Redekop: Yeah. I was going to say the momentum is in some ways priceless, right? Just building that, that feeling that you're, you're making progress. There's a lot to be said there. And yeah, a partner program can definitely help with that initial momentum to get you off the ground for sure.
So we've been chatting for about 25 minutes now, Sam. I'm, is there anything that you think that. I should have asked
you
Sam Klemens: that I haven't. Well, I would, I would just say I think that for any newsletter operator you should be paying attention to your stats. You have to track absolutely everything that's happening with your newsletter.
The open rate is the most obvious one, which I've already said I don't pay a lot of attention to but it's important but you really need to dig down Into your newsletter and find out [00:23:00] what's going on. I can create different segments. I can find out, for example, like the referrals from this newsletter have this open rate and this click through rate and referrals from this source had this 1 and so I can break all of this down and see in granular detail what kind of traffic is coming my way and what kind of sources that makes sense to.
Pay more for, pay less for. And the other thing is your overall number of subscribers. While that's important, that doesn't tell you everything because it doesn't really reflect the quality of subscribers you have, whether they're engaged with your newsletter or not. So I have 14, 000 subscribers right now, but that's with.
a heavy cleaning of my list. I'm always unsubscribing disengaged subscribers. So if I wasn't doing that, I could have 22, 24, 000 subscribers right now easily, but that wouldn't add anything to my results for advertisers [00:24:00] because those were all unengaged readers. Anyways, it wouldn't make any difference. So it would just be a fluffy number vanity metric.
Vanity metric. Exactly. It would sound cooler. 22, 000 versus 14, 000, but it wouldn't make any difference. So you're, you're just, you really need to pay attention to the quality of your subscribers, how engaged they are, and not just see a big shiny number and think that you're doing really well.
Dylan Redekop: Yeah, I couldn't agree more.
So basically. Know where your source of subscribers are coming from. And especially I would say if you're employing a paid strategy like you are with Twitter, primarily, you need to know, you know, the channels that are, that are making your subscribers convert and how much you're paying for those. So that's a great piece of advice.
And then don't chase the vanity metrics of a 50, 000 subscriber list that only gets a 10 percent open rate because that. It doesn't do
Sam Klemens: anybody any good. Garbage, yeah. And I would, I would do the same thing even with SparkLoop when I was, when I [00:25:00] was using the partner program a lot, I would break down every single partner in my newsletter to see what the CTR was, what the open rate was.
And one of the things I really like about Sparkloop is that I could choose to increase or decrease the payout to each partner individually. So that was super cool. So I would pay some, some partners 3 and other partners 1 and that worked out because just based on the quality of subscriber that they were sending me.
So, yeah, you really have to track these stats. Yeah,
Dylan Redekop: and you can really incentivize those partners to, you know, drive you, drive you a lot of traffic too. So, thanks for the shameless plug.
Sam Klemens: Well, it's my, my newsletter, my newsletter would not be here without SparkLoop. So it's been, it's been huge for me.
Dylan Redekop: Well, that's awesome.
We're happy to be part of your journey. And I really have enjoyed chatting with you. Thanks for being so forthcoming with all that information and sharing all those great tips with us. Let our audience know where they can find you and find the rollout. Yeah, well,
Sam Klemens: if you just search Google for the roll up, it'll come up.
It's [00:26:00] blog. therollup. io and despite doing Twitter advertising, I'm not really on Twitter. I don't really post there much. I'm more of a, I'm more of a lurker. So yeah, if you just want to check out my newsletter, that's where you'll find me. Awesome. Thanks,
Dylan Redekop: Sam. We'll include all those, uh, links in the share notes and have a great rest of your day.
Yep.
Sam Klemens: Thanks for having
Dylan Redekop: me. See ya. Thanks for listening to this episode of the Send Grow podcast. If you like what you heard, here are three quick ways that you can show your support. Number one, leave us a five star rating and review in the podcast app of your choice. Number two, email or DM me with some feedback with your questions or with suggestions for future episodes.
And finally, number three, share your favorite quote from the episode on social media and tag both me and our guest. All of the links for that are available in the show notes. And whatever option you choose, I am really grateful for your support. Thanks and see you next week.