Send & Grow by SparkLoop

Send and Grow Epiosde 011 - Jason Woodruff
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Louis Nicholls: [00:00:00] Welcome to the Send and Grow podcast. I'm your host, Louie Nichols. In my day job at Spark Loop, I spend all my time helping the best newsletter operators and media brands in the world to grow their audiences. So I get to see firsthand what growth tactics, strategies, and channels actually work, which ones you should copy, and what mistakes you should.

And now with this podcast, you get that access to. 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 so you can become really effective at growing and monetizing your email audience. Today I'm joined on the podcast by Jason

Jason Woodruff: Wood.

Jason is the founder

Louis Nicholls: and c e o of the pour over maybe one of the most exciting newsletter growth stories

Jason Woodruff: of the past few years.

Louis Nicholls: Jason, we're gonna dive into what makes the pour over so special today and [00:01:00] how you're doing growth and monetization. Can you maybe kick things off for us with a quick explainer of what the pour over is and who it's for?

Yeah, so

Jason Woodruff: the pour over. It's current events, summarized current events, so similar to a whole bunch of other newsletters. Our kind of unique proposition is that we're Christian, so we write about eight to 10 stories in each newsletter, and the three largest ones, the longer ones, we provide a Christian perspective with the the remaining five.

We don't do anything and it's just the news and we are politically unbiased, so a lot of Christian news outlet. Have leaned conservative. And so our goal is to say, Hey, we're gonna be politically neutral. The only bias, the only kind of pressure is going to be kind of towards foundational biblical principles and w w we just want to be a good trustworthy news source.

And we've had people that reach out and they're like, Hey, I love. The pour over. I don't like Jesus, but those parts are clearly marked, so I just skip 'em and good [00:02:00] work. It's like, Hey, obviously we like the Jesus parts, but glad we're we. We have also, the reporting stands on its own, so we have 340,000 newsletter subscribers, high 50% open rate.

And then we have a podcast that gets about 10,000 downloads per episode and a hundred thousand followers on Instagram. Awesome. Yeah.

Louis Nicholls: And you are sending out multiple times a week, right? I think not quite daily at this point, but almost daily, right?

Jason Woodruff: It Monday, Wednesday, Friday. Yep. And we've been doing that for a long time, and about every four months talk about whether or not we're gonna go five times a week.

And it, it's been. Kind of interesting to remake that decision over and over and, and we keep deciding to stay at at three for now, but it's, it's kind of constantly an open topic. Yeah.

Louis Nicholls: Well, let's, let's rub some salt in that. We, let's stick into that right now. Yeah. We'll, we'll go into the history of, of the pour over how you got started and how you kind of grew to where you are today.

But if we're talking about that already, [00:03:00] why, why three times a week? Why not five times? Why not a weekend?

Jason Woodruff: Yeah. So when, when it first started, it was once a week. It was just me. It was a, it was a personal exercise to say like, Hey, I'm, I'm sick of not having news that I can kind of relate to. And then we moved to three times a week.

And originally the decision was just capacity. You know, like everyone was working another job, we just couldn't do five times a week. But we've, we've stayed with. The, the argument for staying with three times a week is, it's a little bit like Chick-fil-A being closed on Sunday. You know, like they say like, ah, the, the, the chicken tastes sweeter cuz you can't get it all the time.

And there's a little bit of that and, and we have a really high open rate. We are frequently right around 60 or above 60, which is awesome. And I think in part of that is it's not there all the time. So like when you see it, if you like it, you're like, oh, the pour overs today. So there's a little bit of that scarcity.

It also, With our mission a bit, which is to [00:04:00] say we shouldn't be obsessed with the news. Let's break the 24 hour news cycle. And a lot of daily newsletters will say that as well. And then they send a 15 minute email every day and they, they say it only takes five minutes to read, but. It's much longer than that and it comes out five, six times a week.

And it's like, that's still basically a 24 7 news cycle, you know, and, and you're just really consuming a lot of it. So those are kind of the two things. And then originally we said, Hey, when there's advertiser demand to move to five, like that, the, the pressure will just be too great and we'll do it. And we've certainly reached that point.

We can also just, again, kind of scarcity, keep jacking up the prices and helps with work-life balance, all that. So those are all the reasons that we've stayed with three. The, the reasons to go to five are financial, you know, it just boost inventory by 40% is, it's, it's rare that you have an easy button like [00:05:00] that.

And again, like kind of the missional argument is to say, Hey, we want to inform people and help Christians think about news. Early on when they hear it from a framework of their faith and, and not let it just be rooted in political ideology or whatever. And, and so the sooner we can get to them, I mean, if, if there's a big news story that happens Wednesday morning, they, they're gonna hear about it five times, six times before our email arrives Friday morning.

And so that's, that's the argument, kind of the missional argument.

Louis Nicholls: Interesting. Okay. I like that it's. Whenever you talk to different newsletter operators, you very quickly realize that. Every argument for something also has a compelling argument against that same thing. So you'll have people sitting here with a daily newsletter going, oh, well we went to daily because we wanted to to habit form.

We wanted everyone to go into the habit of reading every single day, and that's why our open rates are so high. [00:06:00] And then you'll have other people going well, The reason our open rates are so high is because we don't send every single day. So when we send something people open, it's, it's almost like we're making it up as we go along.

Jason Woodruff: Oh, there, there's a fair bit of that as

Louis Nicholls: well. So what I want to do before we get into some of the questions about how the, the pour over is, is doing today and, and how you're thinking about the future, I'd love to take a quick look at, at how you got to where you are today and really what I want to do. I want to look at this from the perspective of somebody who is thinking about starting their own newsletter and hoping to grow it to, to, you know, into a sustainable business like the port over, and they're looking at you and they're looking at tens, if not hundreds of thousands of other newsletters that on the surface all seem kind of similar.

And started at the same time and have a couple of hundred subscribers now rather than a couple hundred thousand. So really what I wanna get at is, is why is the poor ever different? What did you do differently? Why have you been successful? Where others who, on the surface were doing similar things, haven't.

Maybe we can start with like the first a hundred subscribers. Like where did the idea come from? [00:07:00] What made you push send on the first edition and where'd you get those first hundred subs from?

Jason Woodruff: So, like I said, the, the motivation it was, it was a personal exercise and it was me. Hey, I, I like the news and it, it is frustrating to me that as a Christian who says, my faith should be the biggest part of my life and my worldview, my options for news are all something that puts a political ideology first.

You know, and, and even news sources that are claiming to be unbiased, are politically unbiased. It's, it's the same yardstick and a lot of news sources that are claiming to put their faith first. It, it's just, Wow. It's amazing how much your faith aligns Exactly. With your political ideology on, on either side, you know?

And so it's like, man, why is this so hard? So that was the motivation. And I was talking with a friend over dinner and I was saying this, I'm like, I'm gonna do this. Like I have, like it wa I was. Getting my MBA at the time, but we had just had finals and I had a few [00:08:00] weeks before my internship started, I'm like, I'm gonna do this.

I'm, I'm gonna send you an email on Friday. And so I did, and we still have that, it's called like unnamed email. And it was right after Barbara Bush died. So that was the big story. And it looks completely. A thousand percent different from what the Pour Over looks like today. And so really, I would say the first thing is the, the first a hundred subscribers came from friends and family.

I knew all 100 of them. Like I had all of their cell phone numbers. That's where they came from. And, and it was, it was scary and hard, you know, like that was one of the first hurdles was to be like, Hey, like, yeah, I guess I'm actually gonna like, promote this and like, put my name behind it. And, and that felt vulnerable and.

Louis Nicholls: When did you actually do that? Did you do that after the first send or like in the first couple of weeks?

Jason Woodruff: The first one actually went to probably like 10 people, so there was a little bit of that, but those were like, you know, [00:09:00] mom, dad, wife, like, really, Hey, even if this is horrible, there's n there's real, there's no real risk.

And I mean, after a year we had like 250 subscribers or something like that. And so that would be my first piece of advice. It exists today because I enjoyed doing it and the early writers enjoyed doing it, and it was like, Hey, this really is because there was, there's no money in a newsletter that has 250 subscribers.

It just, It's only potential. So there were three of us kind of working on it at the time, and I don't remember when this was, but we set a date of like, Hey, by this date we need to have 2000 subscribers, otherwise we're ending this because it's a lot of work and we missed it and no one mentioned it. And we just kept going and very glad we did.

But so I, I think that's part of it is, hey, you gotta enjoy it and you got to. Listen to feedback. Like I said, [00:10:00] the the first it, it looks very different and the changes were like, we changed the name, we changed the type of news we covered, we changed all this other stuff and, and I think part of it was there was a thought.

Like, obviously I liked the content, I also liked the business side of it, and so we monetized way earlier than made any sense. You know, it was like we were wheeling and dealing to get like a $25 ad placement and brought on Mitch, who also works for Spark Loop to help monetize it in early 2021 when I think we had like two, three, 4,000 subscribers, which like, that's a hard job to, to sell ads.

When you just don't have a big audience. And so a big part of that was, hey, we wanted to create a sustainable business model and we really liked the content, but both of those things were. Enjoyment, you know, and the pour over always had to stand on its own. Mitch asked [00:11:00] for a, an email like mitch@thepourover.org email address, and I was like, dude, that's five bucks a month.

We cannot afford that. And so he, he didn't get one, just had to use his Gmail to make the first few sales. And he,

Louis Nicholls: he's, he's still being very cheeky. He's asking us for a sparkly female address. Right.

Jason Woodruff: Yeah, I know this is horrible. So, but there was a, a weird switch where like early on it was like, Hey, I'm not going.

Even if this is something that Jason can afford, it's something that the pour over can't. Now those tides have turned where it's like, Hey, Jason's not covering the, you know, even our, our like mug order, you know, but the pour over can and, and so if I were to start a new newsletter today, I would. Because I know the potential of it.

I would invest a lot more money in it to get it moving faster, but we didn't do that. It was, it was slow. It was less than bootstrapped, you know, like it, it had to provide for itself.

Louis Nicholls: I love it. Yeah, it's, it's one of those really interesting things. Talking to people who started, you know, a couple of years ago, it's [00:12:00] amazing how much, just over the last 12 months.

Mindset has completely shifted to it being acceptable to be aggressive about subscriber acquisition in the early days. Mm-hmm. And to put some money behind it because the, the really frustrating thing for us, even at Spark Loop, just like 12 months ago, 18 months ago, was that. Everybody had this perception that newsletters all sort of just grow one way, and that doing anything paid to grow your newsletter is bad and it's gonna result only in low quality subscribers and basically that, that nobody does that.

And then you had all these, you know, and you'd say, well, look at. I, I won't name any names, but look at these really big newsletters that have grown really quickly. Oh, something, they must have got lucky, or they must just have exceptional content, or something like that. And the answer is

Jason Woodruff: no. They all like, no, they're spending half a million dollars a month on growth.

You know, like there's some articles out there where those, those big newsletters are like, yeah, we grew a ton in 2018 cuz we spent 5 million. It's like, yeah. Well, I mean, [00:13:00] the referral program is awesome and they are still our highest quality subscribers and it's. They're the cheapest, highest quality.

Absolutely. But the problem is that it, it doesn't, it doesn't scale on its own like it is as you scale from paid. It's just a, it's an organic boost to everything else. But like, if you just wait for that alone, which is what we did it, it takes years, takes a really long time and the content's gotta be on point and shareable and yeah, totally.

Louis Nicholls: It's, it's just, you know, all these, these large newsletters that if you peek behind the curtain, nearly all of them had some huge ad spend, or they got really lucky with being recommended in another publication where they had a friend who got them 50,000 supplier. You know, on day two or something like that, or they mm-hmm.

They took part in these, you know, in, in like co reg campaigns where they just get, you know, a whole list of a hundred thousand subscribers [00:14:00] dumped in on like week three and Okay. Most of them were, were rubbish, but they, they still had like 10, 20,000 good ones at the end of it. So it's nice to see that people are being a lot more realistic nowadays about like what's actually happening and that it's okay to, you know, You don't have to sort of suffer in silence for years.

It's not like a noble profession where you have to, to spend three years in pain just to, to earn the right to, to grow. So I guess when was like the, the first inflection point for you with growth and you got sort of. Choling along. You're enjoying it. You're writing, you're learning a lot about the audience.

You are selling these $25, $50, a hundred dollars ad slots. Mm-hmm. When did things start to, to really kick up a, a gear, would you

Jason Woodruff: say? So it was early 2020, and we had someone reach out to us just like a Facebook message, because we were running Facebook ads, but they. Bad. And someone reached out and was like, Hey, like is this a [00:15:00] pandemic project?

Like love the Mission. And he's advised on a bunch of e-commerce business and other stuffs. He, he's in his thirties and, and so we just started chatting. I was like, yeah, like, you know, started before the pandemic, but here's what's going on. And he, he just, Brought like digital ad experience and other stuff and was just like, honestly came in and gave a fresh outside perspective of things that I saw, but just kind of wasn't confident enough to move on where he's like the, the cost per acquisition.

Is a lot lower than the value of a subscriber. Like, why are you not dumping money on this? And I can get your cost per acquisition down. And he did, like, he ran our Facebook ads for a little bit. It was early on and we were benefiting from all sorts of new stuff, but we could get subscribers for like, 25 cents for a few months and it's like we are just started dumping money on it.

And that was the light bulb moment, you know, that, that [00:16:00] you're talking about of like, wow, we don't need to suffer quietly or just wait for purely organic growth. Like these subscribers coming in. We, we have a valuable offering. These subscribers coming in are, are valuable, good, engaged readers. We really need to think about, hey, there's the, there's the content side and we have all the operations set up and running, and then there's the like business side of we need to invest in figuring out how to not just create good news content, but good ad content and figure out how to run TikTok ads and Facebook ads and Instagram ads and all that stuff.

And so it was early 20. That we saw the first inflection point and like we went from 3000 to 10,000 subscribers in the first half of 2020, and it was like, oh wow, this is. Like this could work and ended the year with 25,000 subscribers and then obviously grown [00:17:00] a lot since and just have systems in place that are kind of always on and, and always generating new subscribers.

Louis Nicholls: Yeah. Let, let's talk about some of those, those systems then. Can you give a, a breakdown at the moment of like where, where growth is

coming

Jason Woodruff: from? Yeah, so we, most of our paid, I'd say, It's probably like 75% of our paid growth is still on meta. We're kind of constantly we have not figured out TikTok, I can't make a good TikTok to save my life, but we know that there's a potential there.

And so we keep putting a a few thousand dollars a month into that of like, I'll make a few, we'll pay people for a few. And it's like we're kind of waiting for that to hit. We know we see the potential and then the other 10% or so would be on, on the partner program and just kind of more affiliate stuff. We, we have the pour over up on the partner program and then we like reach out to people.[00:18:00]

And say like, Hey, you should go do this, and, and we're launching an influencer version of the newsletter where basically it's all the same content, but instead of get 10 referrals and get a mug, it's like, Hey, we'll just send you the mug and the shirt and the sticker and we'll give you $2 per referral.

So it's more than just putting it out there on the partner program, although, That gets us a lot. It, we, we do kind of push that as well.

Louis Nicholls: Yeah, I I love that. I was, I was talking to Stephan who runs the, the Alts, the alternative investing newsletter. Yeah. Who they've, they've been doing the referral program with us for a while and it's, it's, it's going well.

And then they started bringing in the partner program as well where they can, you know, in effect pay the high quality subscriber and they said like the difference there in terms of like, just figuring out people who, like the newsletter who have large audiences inviting them to become a partner and saying, Hey, for every good subscriber you send through, you can make whatever it is, a dollar, $2, $3, and so on.

It's just been, been huge for them, [00:19:00] and they've been able to invite so many different influencers and other newsletters and people to do that. So I I, I'm very excited about that part of it over the next, let's say, year or so. I think that's super smart. Cool. So that's the paid growth. How about. The non-paid stuff, what have you got going on there?

So we have

Jason Woodruff: the referral program and, and that, honestly, I don't even pay attention to it. It's just always on. It's always working. We do some like, Paid on that of like, we'll do giveaways and things to kind of push it and love doing that because one, the cost per acquisition is still so low and we have found like guaranteed instead of like, Hey, enter for a chance to win an iPad.

We'll do, if you get to referrals, we'll send you a $5 Chick-fil-A gift card. And on the surface that. Oh, we're paying for a $2 and 50 cent lead, but a bunch of people get 10 referrals and a bunch of people get one. And so like it. Way cheaper than that. And it has [00:20:00] the benefit of that then pushes, there's some hurdle, like the first referral is hard and so like to just get someone to be like, oh, like I can, I can send this to two friends, and then they have two referrals.

It's like, oh, I, I get how this link works. I get whatever. So that's a, a little bit paid, but the organic stuff, and then we do cross promotion and other stuff, but I really don't like those. Anymore. It's just in my mind, it is always a favor we're doing to someone else or for someone else because the quality.

So hit or miss. And so it's like, hey, if, if there's someone that's looking for help and, and trying to offer something in return, like we, we, we may do it. But yeah, I don't, I don't really consider that a, a source of growth.

Louis Nicholls: It's, it's interesting you mentioned that about the, the giveaways where you have like, The, the guaranteed what we call like the time limited referral reward, where you, you just, you know, make two referrals this week or this month and you'll get, get this specific [00:21:00] thing.

Because what, what we see is that as the newsletter grows, you'll find it easier and easier to, to find partners. Sponsors brands who will provide you with the provi prizes. Mm-hmm. But at the same time, the larger your audience gets, the less likely people think it is that they'll be the one that will win.

Everybody overestimates. How many people are taking part in these giveaways and they think, oh, I have a, a one in 10,000 chance of being the one who gets the iPad or whatever. It's,

Jason Woodruff: it's a lot better than that. If you're listening, I mean, I guess if you're listening, you're probably a newsletter operator.

Yeah, it's like we'd give away, we gave away a Peloton at Christmas one year and we got a whole bunch of people being like, ah, like this will never work, or whatever. And it like, it wasn't as big of a hit as we thought. It's like we had a few hundred entries. It's like you one referral and you could win a Peloton.

And everyone thinks they have like, oh, there's 75,000 people on this list. I have a one in 75,000 shot. It's like, No, so the, [00:22:00] the, the guaranteed it like triples the performance. Now it's more money that you pay out, but for all the reasons I said it, it's the cheapest form of paid that we do and I think has a long tail in terms of just organic referrals after that.

Louis Nicholls: For sure. Yeah, I mean, I, I love combining them, so I love thinking about the, the ways that people are, are, are interested in sort of like what their risk tolerance is almost and saying okay. The ideal giveaway for me is the one where you have the person who makes the most referrals, gets something for sure.

That way anyone who has a large audience is incentivized to take part. Hmm. Someone at random. Who makes a referral gets a big prize as well, because the people who don't want the small thing, but just really like the idea of, you know, I'm always gonna buy the lottery ticket because maybe today I'm the one who gets lucky kind of thing.

You get those people as well who, who are interested in a small chance of something big. And then for everybody else, you have the opposite. You have the big chance of something small, [00:23:00] right? Which is just make two referrals and getting that thing. So I like combining them, them all together. But it's, it's definitely interesting how.

You know, make a referral and like the more referrals you make, the, the more entries you get. It's very, very tricky to do once your audience gets past like 20,000 subscribers, unless you have a huge reward. Like it needs to be either, like for some reason Apple products always work, and other than that it needs to be something really big like a car or a huge holiday or something like that, which is interesting.

Cool. So awesome. And then on the, the revenue. Side of things. What's, what revenue streams do you have? Just advertising or do you have other stuff that you, you do as well.

Jason Woodruff: So advertising is like 90% of maybe a little over of our revenue. We sell few premium ad placements. There's one real ad that. Looks like an ad.

Well, it doesn't look like an ad. It looks like a story, but it's like gets the logo and then we, in every email we have our picks of the [00:24:00] week or whatever, and those are paid as well. And so combined, those are over 90% of our revenue. And then we have a, it's just called choose to pay and you can pay what you want.

It's a minimum of $2 a month. And then if you do $50 a year, we give you something. So we incentivize that annual and that's, it's great. It's recurring revenue, like I said, about 10%. We, we give it one ad placement a month and it always, Pays for itself. You know, like we continue to do it because we can bring in as much as we would've sold it for otherwise.

And I do think some of why that is successful for us is that there's a faith component. And so I don't know how. Well, that would work in in other settings. And we also like, because of that we have to be really clear, hey, this is not a donation. It's like you're paying, if pay is written everywhere, it's a subscription.

If you want to make a one-time payment, it has to be [00:25:00] $200 or more. Like you can't just like send us 50 bucks. And so there, there, there's some like nuance around all of that. And then I, the other way to break down our revenue is, again, like 90%, 95% of our revenue comes from the newsletter. We've never really tried to monetize podcast or Instagram very well.

And the podcast, we've gone back and forth. And what we're doing right now is, it's just a, it's like a sweetener. So if you run it in the newsletter, It'll be on the podcast as well. And, and that's just because comparatively the podcast audience, it gets 10,000 downloads when the newsletter gets 180,000 opens.

And so it's just hard. We have a small team. Mitch who sells our ads is only part-time for us cuz he's full-time with you guys. And so it, it's just hard to have him focus on selling a podcast ad for 200, 300 bucks when, when he could be selling a, a newsletter ad for many thousands.

Louis Nicholls: Yeah, of course. Well, let's talk a little bit about the podcast.

Cause I, [00:26:00] that's one of the, the trends that, that seems to be picking up at the moment. Launching podcasts and other types of media around the newsletter. Yeah, so we've seen Morning Brew do that recently, right? They've launched their podcast quite recently and they even bought the whole like, YouTube and TikTok studio they, that they bought recently to, to bring out a lot of that shorten and long form content.

How are you thinking about the podcast? So for

Jason Woodruff: us, I basically don't think about the podcast. So we use a company called Pod Letter and. Basically what we do is when we have finished creating the content for our newsletter, we send it, we like, I ping 'em on Slack and say, Hey, it's done, it's ready. And then they record it.

So it's the exact same content, just in a podcast version. And they record it, produce it, edit it, publish it, and so for months at a time, the only thing I do is. [00:27:00] Slack 'em saying that it's ready to record and then have discussions with Mitch over whether or not and how we're going to monetize it and, and I think that's what's different.

And when we first launched it, I was like, no one else does this. Like Morning Brew has a bunch of podcasts, but you can't listen to their flagship newsletter. I was like, I, I kind of like, I have this hunch that they've all tried it and it doesn't work and so they've killed it because like all the big ones just don't do it.

And yeah, it's been great. Like we, it's has like 4.9 stars and people who like the podcast, love the podcast and the way we think about it is obviously a podcast listener is less valuable than a newsletter subscriber to us. A number of reasons. I would say primarily because we focus on monetizing the newsletter and have figured out how to do that well.

But there are people that just don't like email, [00:28:00] don't read it or whatever, but will listen to every single edition when, when it's the, when it's the podcast. So for us, it's a little bit more of. Brand. We, we don't promote the podcast very much, but it's, it's linked at the top in the header of every email.

Like, Hey, you can listen to this as a podcast. And like I said, it's gets 10,000 downloads. Occasionally an episode will kind of pop off, and we were one day last year, like the, the 12th biggest news podcast in, in the United States. And so it is very minimal effort. And ha has been great for kind of brand loyalty and just kind of meeting, meeting readers and customers where they're at.

Louis Nicholls: Yeah. I, I love podcasts for that reason. I think if you ever meet someone who reads you a newsletter, they'll be excited to meet you, but, They feel like a stranger. Whereas you can always tell if someone listens to your podcast or watches your YouTube videos because they'll come and [00:29:00] talk to you like they know you and you dunno who they are, but they're talk, they're greeting you like you went to school together.

And it's like, I, I should, I know you. I dunno, you. And they're like, yeah, of course. We spend two or three hours together every week. Of course we, we know who we, who we are. Yeah. I think it's super useful, especially if you're trying to, to monetize via direct product or something like that at some point just the, the closeness can be,

Jason Woodruff: can be so valuable.

Yeah. And, and so shameless plug. Pod letter and which I guess the relationship is a little weird, but I would likely get paid somehow. If someone does sign up, it's so pod letter. I had friends in high school that started a production agency and so they do audio and video and make like. Documentaries and, and, and things, and this is just, they reached out, they're like, Hey, we could do this for you.

So we're their only client like pod letter and the pour over. There's a close relationship there, but because it's been working well, we're like, Hey, we should again. Nope, no more work for me if you guys find other [00:30:00] newsletters and so. Open, open for business and an interest if there are other newsletter operators that want to, to use pod letter.

Yeah,

Louis Nicholls: I mean, I'll put a link in the show notes. Cause I think it's, I mean, I've, I've listened to a couple of episodes. I, I think it's really well done and it's such a snappy like turnaround time and. I think it is really, really valuable to, to at least test out. Especially, I almost think like even more in other spaces outside of like the, the daily news space.

I think if you have like a more long form newsletter and you're doing something around marketing or tech or something like that, people are super busy and being able to listen to that I think is. I know I myself would like, prefer almost every newsletter in a podcast form to, to be perfectly honest, like, or at least the option.

Cuz I like, whenever I'm sitting down for like five minutes to read a newsletter, I'm like, I should read like, well, a, I read so many for work and B, like I should really be like walking around or like doing something active right now. Yeah,

Jason Woodruff: yeah, yeah. It's the, the [00:31:00] podcast. It's a, it's an interesting medium for all the reasons you said, like it's, it's more familiar.

It's, you can, it's mobile, all that stuff. Running the podcast, it reinforces to me how awesome a newsletter is when you, you like, have so much more information. The newsletter reader and the links and all the stuff, like, it's hard to drive action in a podcast. But also there are good, like Spotify has like a, a relatively good auto monetization.

Like you can just drop in. And so that's another thing that is a benefit is like it's a low CPM because they take a cut and, and it's kind of generic, but like you can monetize. Two listeners on, on a podcast where, like we were saying before, that's really hard to do in a newsletter format.

Louis Nicholls: Yeah, totally.

Totally. What do you think when you we're looking forward towards, like, let's say we, we sit back down again in a year from now or a year and a half mm-hmm. From now, [00:32:00] what do you think will have changed in the newsletter space, thinking about growth and, and revenue. In particular, like what do you think more people will be trying?

What are you excited to try out over the next year, year and a half that you think is gonna be important?

Jason Woodruff: I think specifically over the next year, year and a half, if there is some, well and already kind of like some re recession fears and other stuff, I think raising money will be harder and I think we might see a few well known.

Names just kind of fold, you know, that got out over their skis of like, they, they appear to be doing better than they are. And so I, I think there's this like part of what your, your question earlier, like why did the pour over succeed when others didn't or, or just still smaller and, and I think. It, it's, it's kind of twofold.

One, we reinvested everything, but we also didn't over lever ourself, you know? [00:33:00] And, and so I think, yeah, like, it, it, it's just a balance. Like you, you gotta invest in, in growth. And there are so many opportunities to do that, but like, be logical and also figure out the revenue side. And like, that's why I love the, the partner network is like, it's, it's also a good source.

Like we recommended. We recommended a newsletter, put in a magic link in our email on Monday, and it is our, our single day most valuable, most money we've ever made from a newsletter was Monday because that Magic Link and partner link just went off, you know, and we pitched this other newsletter and so it's like, man, what?

Awesome way for us to both grow and make money, you know, because this is a bigger newsletter that that has a good budget and all this stuff. So figure out how to monetize the podcast and don't get out over your skis. I don't know. For us specifically, what we want to figure out [00:34:00] over the next year is working with influencers.

It feels like that. And, and some of this is probably like, it, it depends on, on the content, but we've never, we've haven't done much with influencers, but it feels like that's the potential to really go off in you know, like specifically paid, you know, it's like, hey, we can take the guaranteed, get conversions for $2, but if we cough up, you know, 10 grand and get the right person to promote it, Could, could that 10 grand bring.

50,000 subscribers, you know, and then it's like, that's just a totally different math equation. So we want to figure that out. And I know other people have like, and, and seen success, but you know, it's what we're selling is free. So feels like we we're late to the game on that and, and need to invest in, in figuring that out.

Question

Louis Nicholls: I like to ask is, obviously [00:35:00] you've been in the trenches building this over the last couple of years. You've seen a lot of what's worked. A lot of what hasn't worked. What's a question sort of from the perspective of someone who is slightly earlier on with their newsletter? What's a question that I should have asked you but I didn't?

Jason Woodruff: Most of our conversation, understandably, was around the business side and like the content is the business. And that's one of the things that, like, as we're hiring the, the thought was always like, Hey, let's hire more writers and just have Jason not write, you know, and, and now we're saying like, no, actually.

Let's hire more business people and make sure that Jason can always devote half of his time to writing, because that's the way this all falls apart is like if the content suffers or, or whatever. So I think it's a balance because I also, like people will come and talk to me and be like, Hey, I wanna start a newsletter or [00:36:00] something and, and they think that.

Those people are always creators that only focus on the content and think that there's just like easy buttons to grow and monetize it. And it's like, hey, that's half the business. But also it's tempting to just get sucked into that and, and focus and then be like, oh, shoot. You know, and so like protect the time that is around the content.

That's the longevity of the product and, you know, and, and pay attention to feedback that you're getting on the content. It, the subscriber is a person that you actually want subscribed. There are. Tons of crazy, weird, wacko people. And it's like if your alarm goes off of like, Hey, I don't like this person.

Then take what they're saying with a grain of salt. Like there are a lot of people in the world and you don't want all of them subscribed, but if there are people that seem to be like, Hey, this is your target customer and they're leaving or doing something, it's like, man, figure out why that is. And, and protect [00:37:00] the, protect the.

Louis Nicholls: Awesome. Yeah. Well, I'm excited to hear you pitching to, to come back on very soon and talk about the, the content side of things. That's, that's a very generous offer of you and I'm sure we'll take you off on it. Awesome. Well, Jason, where can people go and find out more about you? Obviously they can go over to, to the pour over.

I'm gonna put the link in the show notes, but people can check out themselves and we'll put the link into to pod letter as well if people want to, to check that out for their newsletters, which I think would be, would be a great idea. Where else should. Go and find you if they have questions or thoughts

Jason Woodruff: or, yeah, you can email me at jason@thepourover.org, but I don't do much personal social media or anything.

So if you find the pour over on, on Instagram and message asking for me, it, it, it will eventually be filtered my way.

Louis Nicholls: Awesome stuff. Well, Jason, thank you so much for, for joining me today. Yeah, thank you. Thanks for having me on. Thanks for listening to this episode of the Send and Grow podcast. If you liked [00:38:00] what you heard, here are three quick ways that you can show your support.

Number one, Leave us a five star rating or review in the podcast app of your choice. Number two, email or DM me with some feedback with your questions forward 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.