Does Email Marketing Still Work?

Email marketing has been the bedrock of online marketing. But with so many options available, can it still perform? Listen in and find out.

Ask any online marketer about email marketing, and they will tell you it is the foundation, and driver, of their online sales.

But with so many other communication channels available – like messaging apps – can email marketing still bring in the same types of results?

This is the question that we tackle on this show, with our special guest Darrell Vesterfelt from ConvertKit.

Darrell provides an in-depth insight into how his company has drastically grown over the past two years – including the tactics that have helped them excel in a crowded market space.

And you will want to hear how he did it; especially since his company – ConvertKit – is the email marketing platform for professional bloggers.

In this 41-minute episode, Sean Jackson and Jessica Frick engage in a lively conversation about email marketing, including …

  • Is email marketing still relevant in a mobile first world?
  • The trends in email marketing you need to consider
  • How ConvertKit grew its recurring revenue to more than $6 million in just two years
  • The one “secret” tactic that Darrell uses to exponentially grow their customer base
  • Why focusing on just a small group of people can potentially create a $100 million company
  • And of course, our question for the week – Is affiliate marketing worth your time?

The Show Notes

  • If you’re ready to see for yourself why over 201,344 website owners trust StudioPress — the industry standard for premium WordPress themes and plugins — swing by for all the details
  • Check out ConvertKit at
  • Look at ConvertKit’s amazing revenue growth at Baremetrics
  • Jessica’s recommendation for the week (including referral code), theSkimm
  • Sean’s recommendation for the week (with no referral code :),
  • Follow Sean on Twitter
  • Follow Jessica on Twitter

Does Email Marketing Still Work?

Voiceover: Rainmaker FM.

You’re listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs. For more information, go to Rainmaker.FM/DigitalCommerce.

Sean Jackson: Welcome, everyone, to The Digital Entrepreneur. I’m Sean Jackson. I’m joined, as always, by the lovely Jessica Frick. Jessica, how the Frick are you?

Jessica Frick: I’m great. How the Jackson are you?

Sean Jackson: Always well, always well. Jessica, where did we leave off from our last episode? What was the question of the week that we were wanting everyone to ponder?

Is Email Marketing Still Relevant in a Mobile-First World?

Jessica Frick: We were wondering why you were so snarky when it comes to email, Sean. Maybe that was just my question. Okay, the official question is whether email is still relevant.

Sean Jackson: Email marketing, you mean?

Jessica Frick: Yeah, email marketing.

Sean Jackson: Of course not, but I want to hear why you think you’re right. What say you?

Jessica Frick: It’s not what I think I’m right, Sean. It’s why I am right. Email marketing is still very relevant because by definition, marketing not only helps you increase your sales but enhance your relationships with prospects and existing customers, and email can accomplish that.

Sean Jackson: But don’t you think that with every martech product out there centered on email, that with so many people finally cluing in after decades that email marketing is the number one most effective tool online for marketing, that with so many people doing it, don’t you think it’s going to lose its pizzazz, just because there’s so much more going to be flooding in?

It used to be bad with spam, right? We used to have to worry about spam. Now, we don’t worry about spam. We just worry about every single thing that asks for our email address that sends us a weekly or daily email of something. Don’t you think it’s going to lose its relevance just because of the volume?

Jessica Frick: Oh yeah, I think that there are some tricks that are played out. You can’t turn around without trying to access something someone online promised you with a post without having to put your email in. Then you know you’re going to get like 25 emails after this. You just unsubscribe with the first one. There’s so much static right now in the marketplace, which is why I think it’s important that email marketing be done correctly.

I think that you need to be invited. I think that spam obviously is still done even with people who know better. We see it all the time in the space, especially with digital entrepreneurs. That doesn’t mean that it’s okay. When done correctly, I think that it has a tremendous amount of value for a digital business.

Sean Jackson: Yeah, I think it obviously has value. This is something that we’ve grown a whole business from, the strength of our email list. The way that we had people wanting to give us that information. The way that we interact. The way that we put it together. But certainly, everyone else is clued-in on it. Every martech solution out there now has some form of intelligent-based email sending.

I think as more and more people adopt it, then the inbox is going to be cluttered up with a lot of things that are going to pull your attention away to such an extent that you’ll be like, “Crap, whatever you’re sending me, I don’t want to read it because I’m just getting overloaded.” But we’ve always had that.

The Trends in Email Marketing You Need to Consider

Sean Jackson: Let me tell you why I push back on the relevancy. I will say this, I think you used to be able to send an email to an opt-in list — someone who opts-in — and in doing so, because there wasn’t a deluge of quality emails, then it was easier to stand out. I think now for your emails to be relevant, you really have to put a lot more time into them.

It used to be very easy, I think, but now to maintain the relevancy, you’re going to have to spend time. I think it’s going to also have to be a function not only of design because of how many people read email on their mobile device, but I also think you’re going to have to be looking to the future, specifically HTML5 video. Now iOS 10 supports HTML5 video in the email program. Now, maybe your email is a video embedded in the email that you send to somebody. Think about that for a second.

Jessica Frick: That’s definitely an interesting thought, Sean.

Sean Jackson: Yeah, because then they’re talking about carousel design, when you can swipe back and forth. I think with so many people reading email now in a mobile device that you’re going to start to see people trying to stand out. That means that you’re going to have to be even more on the forefront. Or you’re going to have to have a very deep personal relationship with the person that you are giving your email address to.

I’ll give a case in point. A lot of people know we are big fans of Dave Pell and his NextDraft daily email letter that comes out. If you don’t go to NextDraft and sign up right now, you’re missing out. He recaps the day stories. I always learn something new, interesting, thought-provoking — whether you agree with his politics or not. It’s not a political thing, but he is going to cause you to think.

Jessica Frick: And if you think Sean is snarky …

Sean Jackson: Yeah, Dave is snarky. But at the end of the day, he has a very intimate personal connection with people because he is writing a curated email newsletter with a personal tone of things that really stand out.

Now, I will say this. There’s days I don’t read him, but I will never unsubscribe. I will always peruse it, whether I go in depth or not. I think it’s going to end up, to be relevant, you’re going to have to be a lot more clever, or you’re going to have to be a lot deeper in meaning. What say you?

Jessica Frick: I completely agree. I love theSkimm, which is daily news roundup, but the way that they market via email is also different. That actually makes me want to ask you a question, which kind of sidesteps our question, but it’s still relevant. You mentioned having video or a carousel design. Do you think that it would make email more irrelevant if your email was more interactive, or is the point still to send them back to your web property?

Sean Jackson: I think if your audience is mobile first — which almost all audiences are … not every one of them, but a majority of them are — then I think the more interactive the email, the better. We’re coming to expect that in our mobile experience. I certainly think video, which is still the predominant media content outside of text, that on a mobile device the people consume, I would say that you’re going to have to really figure out a way to stay above and beyond and do it in a meaningful way.

But if your audience is still very old-fashioned, text-based, then I think a more rich email, something much more meaningful, not so long actually. That’s another big trend that’s come around because so much people, at least interacting with email on a mobile device, then they’re going to have to be a lot shorter.

I really think you have to look to your audience, realizing that they, in my opinion, are now not going to have to worry about traditional spam, Viagra and credit scores aside, but really thinking about, “Wow, I’m competing for attention, so maybe I have to really stand out to get their initial attention.” And video, in my opinion, would be one way to really stand out in someone’s inbox on their phone.

If you don’t think I’m right, that’s okay, but I will say this. All the trends that I’ve looked at are pointing to the fact that email is still and is predominantly used in online marketing. With everyone cluing in on it, your messaging is going to have to be strong, which means you’re going to have to work harder at it to stay relevant. How’s that?

Jessica Frick: I think you make some very strong points, and I disagree with you less this week than I have in previous weeks.

Sean Jackson: Ooh, well, then we’re going to have to work on a new topic where we could really battle it out. Because we start agreeing on things? Oh my word, that’s going to be a problem.

Jessica Frick: Yeah, I think that it’s important that the message be heard. So long as it’s done right, email marketing is still relevant, but that ability to do it right, that’s where the secret sauce comes in.

Sean Jackson: I think you’re right, and I think it’s just going to get a little harder to stay that relevant. It’s nice that we’re talking about this because, this week, we actually have Darrell Vesterfelt from ConvertKit as our special guest. They’ve really built their whole company on creating a product that helps with email marketing for bloggers. We’re going to talk a little bit about how they grew their company and the tactics and techniques they did as being an email marketing provider. We’ll have Darrell back after this short break.

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How ConvertKit Grew Its Recurring Revenue to More Than $6 Million in Just Two Years

Sean Jackson: Welcome back from the break, everyone. Jessica, please introduce our special guest for today’s show.

Jessica Frick: Today’s guest is someone I’m very excited to introduce and to hear more from. We have Darrell Vesterfelt, who’s head of sales, growth, and business development for ConvertKit. Darrell has worked to help bloggers and authors establish and grow their platforms for more than 10 years. He lives in Nashville with his golden doodle Cooper.

Darrell Vesterfelt: The important stuff.

Jessica Frick: Exactly. Well, I skipped over a whole bunch of other stuff because, if there’s a golden doodle involved, I feel like that’s important.

Darrell Vesterfelt: Very important. Very, very important.

Sean Jackson: Hey, Darrell, welcome to the show. I want to start off with you explaining what the heck ConvertKit is because you guys really came out of nowhere. In 2015, you got started. Then you got some little success, and then all of a sudden, you guys are everywhere. Give our audience a quick high-level view of what the hell ConvertKit is.

Darrell Vesterfelt: Yeah, ConvertKit is an email marketing software built specifically for professional bloggers. What we mean when we say ‘professional bloggers’ is anybody who’s trying to earn money from creating content online. This tool is built from the brain of our CEO, Nathan Barry, who was using other tools like MailChimp and AWeber to sell his ebooks, courses, and all he digital products online.

He wanted a tool that would just take his business to the next level, so he created ConvertKit for himself and then started inviting his friends to use it. It had a slow growth over the first couple of years, and then just in the last few years, we’ve just really exploded. We’re an email marketing tool specifically for content creators — so bloggers, authors, speakers, content creators, freelancers, coaches, consultants, shop owners. Anybody who’s creating online content trying to earn money, we’ve created the email marketing tool for those kind of folks.

Jessica Frick: Now, I’ve seen you guys grow exponentially over the last couple of years. Specifically, you went from a $100,000 to $500,000 paying users in a year. How did you do it?

Darrell Vesterfelt: Yeah, when I joined up in January of 2016, we are at a $100,000 a month in revenue, which was awesome. Just a really great time to come in to the company. I think I was the eighth employee to join. The biggest change that happened when I’ve joined is that we just put a focus on growth.

When there’s a small company — I think you guys know this because you’ve been there before — everybody focuses on everything. Everybody’s doing customer support. Everybody’s focusing on growth and partnerships, and I was one of the first hires that had a single focus when I joined the company. My focus was, “Hey, let’s increase the number of customers we have. Let’s increase the revenue number.” Like you said, we went from $100,000 to $500,000 a month in revenue in just 12 months. I think it was because we took a very specific focus, so that was the first thing.

But I walked into a very lucky situation for a lot of reasons. The biggest one is that ConvertKit had a very, very specific niche focus. That was huge. I don’t even think that we realized how big of a deal that was at the beginning, but I would attribute all of our success and growth in marketing to that very, very specific niche. If you go to all of our competitors, they’re going to say, “We’re an email marketing tool for small businesses,” or, “We’re a tool for any kind of business,” or whatever it might be.

We’ve always had the phrase, “We are email marketing for professional bloggers.” We’ve gotten pushback after pushback after pushback on that because people will say, “Well, I’m not a professional blogger, so it’s not for me.” We’ve stood our ground in that a little bit because we know that the reason that we’re winning is because we’re creating a tool for very specific person. Because we’re creating a tool and a product for a very specific person, we might not have all the features that a competitor has — but we still win.

Jessica Frick: You’re not trying to be all things to all people.

Darrell Vesterfelt: We’re trying to be one thing for one person, and so we win. That, to me, was the thing that I walked into, that I had no part of creating whatsoever, that made my job really easy when I did join the first part. I would attribute that single thing as the bedrock, the foundation of all other growth activities that have happened, have happened from that place of being so focused on creating a tool for a person rather than a tool for all people — and that makes it.

Sean Jackson: I do want to go through the specific tactics and some of the things that you introduced in there. But I want to play devil’s advocate, which is pretty much my role on the show.

Darrell Vesterfelt: Love it.

Sean Jackson: I’m going to be Mr. Investor guy. You come to me with this pitch on December 31st. I’m going to be like, “Look, dude, first off, you got Drip out there, which is backed by Leadpages. You’ve got all these email marketing programs, from the SurveyMonkey over to AWeber to Constant Contact, you name it. Really, given how much competition is out there, is there really any hope for you whatsoever? Sure, you’re going to find this little niche as you call it, but how big could that really be?”

That would be my pushback to you on December 31st. What would you say?

Darrell Vesterfelt: You know what, Sean? On December 31st, I might have agreed with you — if I’m being completely honest. I was like, “Yeah, this seems like we’re really limited here. This seems like a really small niche,” and I think this is why people resist this approach. Because it’s like, “Oh my gosh, it’s so small.” The market for email marketing tools is billions of dollars a year. It is a massive industry.

For us to pick a very small sliver of that seemed crazy, and people thought we are crazy. Our customers even sometimes thought we were crazy. We thought we were crazy, but I think the reason that it won is because email marketing is a red ocean. It’s not a blue ocean anymore. There are more competitors out there than ever. How do we stand apart from a competitor?

Well, one of the ways that we can stand apart is playing this feature war battle where we’re always releasing the next new thing, the next cool feature, the next thing that will set us apart, as a feature, from our competitors. Well, the problem is, that’s really, really expensive to do. I’m going to have to pay all these developer hours to release these new features. Then what happens is you have a tool like Infusionsoft that has just added feature after feature after feature after feature, and it’s confusing. Like, “We have affiliate marketing, email marketing. We have e-commerce. We have check out pages.” It’s confusing.

Jessica Frick: I feel like there’s a nickname in there.

Darrell Vesterfelt: Confusionsoft, I think. Yeah. You just bloat the product, so we came into the market, Sean, saying, “What do people who are like us need?” Well, they need a powerful tool that’s easy to understand. We’re not going to release a ton of features for everybody. If we release features for everybody, then we run into the ONTRAPORT and the Infusionsoft problem where, sure, very, very powerful tool, but it’s confusing as hell for our users.

Because we knew our users and because we were our users … I was using ConvertKit before I ever started working at ConvertKit. Nathan built ConvertKit for his own info-product business. We knew exactly what we needed. We knew exactly what our friends needed, so we decided, instead of playing the feature war, we’re going to play the niche war. We’re going to put this stake in the ground, and we’re going to say, “We are for bloggers, period.”

Now people who aren’t bloggers use that. So now we’re creating the tool specific to a person, and we’re winning. We’re winning not because we have the most features, but we have the right features. We’re winning because we’re creating the tool for this person specifically rather than creating a tool that hopefully ‘everybody can use.’

The One ‘Secret’ Tactic That Darrell Uses to Exponentially Grow Their Customer Base

Sean Jackson: Let me jump in. I want to go through some actual tactics here because literally in front of me is a screen from Baremetrics that shows your actual growth rate. I’m comparing between 2015 and 2016, and the lines are so drastically different. 2015 looked flat with a little curving up in October, and then all of 2016 looks like a straight line going to the moon.

Talk to our audience about the tactics you did. You started January 1st. You guys had your niche identified. Everyone thought you were crazy, which is great. You get in there. Let’s talk about those months and what you started to do by focusing solely on growth because you’re the only guy there focusing on growth. What did you start to do? What were some of the challenges, and what were some of the things that worked for you?

Darrell Vesterfelt: Yeah, the biggest focus that I had right out the gate was doing partner webinars. The reason I did that is because, in the niche that we had picked, the blogging niche, webinars were a language that people could understand.

We came in, we honestly started trying doing webinars with a pitch for an annual plan, which I think was $300, so for $300, you get a year of ConvertKit. You get all these bonuses, which is kind of the general plan for webinars that people have had. “We’re going to come. We’ll teach you for 30 or 45 minutes. Then we’re going to pitch you a couple hundred dollar product, and then you buy.” We would convert, on those webinars, maybe five or 10 people into customers.

When I came in, I said, “Let’s rethink the game a little bit,” because yes, webinars are the language that people speak in this industry, but also, people kind of hate webinars. Why do people hate webinars? People hate webinars because they feel this pressure to buy. Or the thing that they are asked to spend money on isn’t relevant to them. Or the teaching is self-serving to the person presenting, and it’s not serving to the audience.

The first thing I did is said, “We’re going to do partner webinars because it’s a proven method. It works, but we’re going to change it up a little bit. We’re going to do it different than anybody else in our space whatsoever.” So we did what I call the ‘no-pitch webinar.’

We would get on, and I would teach the highest value content I could that was relevant to our product, which in this case was how to grow your email list. I spent a lot of time — I think there’s a 115 slides in my presentation — helping people with a proven method to grow their email list. Then, at the end of the webinar, instead of saying, “Hey, thank you so much for learning, spend $300,” I actually just gave away everything for free. I gave away the software for free. I gave away ebooks, courses, all these bonuses. I think it was $300 in value worth of stuff. We gave it away absolutely free.

Sean Jackson: So then you’re looking for a job on January 2nd with that approach?

Darrell Vesterfelt: Yeah.

Sean Jackson: Did you face any resistance to that? Did you face any resistance internally to giving away the product and all this information for free?

Darrell Vesterfelt: I did at first, but we have a culture at ConvertKit that I really love — that is always be testing. We tested this out with a few webinars, and what we found, Sean, is that people were so much more apt to try out our software when there was no money exchange at all.

So, “Hey, we’re going to give you 30 days of this product for free. We’re going to give you this $200 course for free. We’re going to give you this $50 ebook for free. We’re going to give all this stuff away, absolutely free. All you have to do is try it out.” Because we had built this goodwill with people, it was very easy for people to say, “Oh, I’ll try it out. I’m using MailChimp, AWeber, Mad Mimi, FeedBlitz, or anything else. I’ll just try it out. There’s no risk whatsoever for me, so I’m going to try it out.”

People would try it out, and they would either decide that it was a tool that was good for them or it wasn’t. So it was a lot easier for us to push. I think I taught something like 115 webinars with 60,000 registrants total in the last year. We went all in on this. The way that we did it, too, is we knew that we were brand new, so we didn’t have an audience yet. We would partner with people who had audience of our core users.

Jessica Frick: Like StudioPress?

Darrell Vesterfelt: Like StudioPress. That was a great webinar, actually.

Jessica Frick: We got a lot of really good feedback.

Darrell Vesterfelt: Yeah, what we do is we say, “Hey, we’ll compensate you.” This is the traditional partner webinar style. The thing that we would do differently, Sean — because there was no pitch and no money being gathered on that webinar — is one, partners felt a lot more confident in promoting it. So we’d get higher registration totals than I think normally would happen because they could say to their audience, “Hey, they’re not going to ask you to spend any money. They’re not going to make a pitch for you to buy a product afterwards. There’s a bunch of free bonuses.”

So we’d get registration numbers at a higher level. Then we have an affiliate program that would pay 30 percent month over month for the accounts that decided to stick with ConvertKit, for the lifetime of those accounts. That was another win because now these people could build recurring revenue instead of maybe just this one-time payout from an affiliate webinar. They would then get the opportunity to build recurring revenue that every month they would get the same revenue by building up through our affiliate program.

Sean Jackson: How did that work, by the way? We here have experimented with both measures. We’ve experimented where they give you tons of money or give you a little piece every single month. I would say that, for some people in the affiliate space, the big check is what gets their attention. Getting a $30 check or $20 check month over month, even though it could be for years, they don’t see the same value.

How did you go through that? I think affiliate programs are hugely important in our space. Not everyone does it right. So how did you keep those people interested knowing that you’re not giving them a huge amount on every single check?

Darrell Vesterfelt: That was a key. To me, it was just a numbers game. Most people there’s a very sexy flashy thing when I can send somebody a check for $5,000 right out of the gate, but the reality is, if our average customer is around for 11 months, 13 months, 18 months, then that number gets really dwarfed the longer that this happens.

I would just lay out the numbers side by side, “Hey, we’re more than happy to pay you out at a one-time fee, but I think you’d rather have this building out month over month because, six months in, you’re going to dwarf what this one-time pay out would be.”

The other thing that happened is we went after a key promoter right out of the gate named Pat Flynn. Pat from Smart Passive Income, has awesome blog and podcast, he started using ConvertKit and then became a keystone affiliate. Anything that Pat would do it made it a lot easier for everybody else to follow suit.

Pat was really pumped about this idea. He felt like it really fit his brand to do the no-pitch webinar. He was okay getting the month-to-month referral. The fact that then Pat publishes his income report really helped us out as well. But having that keystone affiliate and partner, doing it first and being very excited about it, really made it easier for all these other partners to follow a suit. If somebody at the top of the industry does it, it just opens the door for everybody else to follow suit.

Sean Jackson: I want to go through that for a second. When I was reading about your story, I was like, “How did they get to all of these people to do these no-pitch webinars?” One of the things that I read, and correct me if I’m wrong, that because you did have people who were professional bloggers, back to your niche, you could look at those existing customers and go and say, “You have a pretty big site. Can I reach out to these people who are already using the product?”

So for you, correct me if I’m wrong, but I think part of your initial work was just going to your existing customer base, who were bloggers, and say, “We’d like to do this no-pitch webinar.” Is that correct?

Darrell Vesterfelt: Yeah, that’s one of the first things I did. The first two things I did is, I tapped my existing network because I’ve been in the space for more than 10 years. So I tapped my existing network, one. Two, I just looked at our customers, and it was really awesome.

At the point I joined, I think we had 1,800 or 2,000 customers, and I just would say, “Who are our top customers, and which one of them would be a good fit for our webinar? Oh, by the way, we have the most generous affiliate program for email marketing service out there. Would you be interested in joining? Oh, by the way, we’ll also do all the work. All you have to do is send an email.”

I think we built up a reputation over time of, “Hey, they teach really high-quality content,” number one. Number two, people are getting good-size monthly payouts from it. Number three, we had the relationship, either as a customer or as a network that had been built up over about a decade.

Sean Jackson: These were your primary tactics that you used in 2016. Am I correct?

Darrell Vesterfelt: Yeah, but the webinar is definitely the biggest one.

Why Focusing On Just a Small Group of People Can Potentially Create a $100 Million Company

Sean Jackson: Let’s go through this. I was reading a great article this morning. Dennis Mortensen, who owns … it’s the automated intelligence for planning, meeting with somebody via email. He made a very interesting observation. He said, “Once you get to a million in annual recurring revenue, you’ve proven that there’s a market for it. Once you get to $10 million in annual recurring revenue, you’ve proven that you can scale it.”

Right now, where you guys sit, and I think you’re at a very interesting point. Obviously, a lot of people listening to this are like, “Oh my gosh, they were at $5,000 a month, and now they are $500,000 a month or almost $600,000.” That, in and of itself, in my opinion, sounds like just blocking and tackling. Hiring somebody who’s focused on this, finding the right value proposition for the audience, and just showing up every day and focusing on growth.

But is it a challenge for you guys going forward to get to that $10 million mark? You’re at $6 million plus now. Where is the next big infliction point for you? What are some of the ideas that you guys are thinking about? Or is it just going to be blocking and tackling like you’ve been doing?

Darrell Vesterfelt: We’ll continue to do the blocking and tackling. I think where we’re at … we just passed $7 million in annual revenue. What we’re doing is we’re getting smarter with the blocking and tackling. This is now we’re thinking how we can automate these processes, how we can do more with a small team.

The other thing, Sean, is now I’m not the only one focused on it, but we only have three people. We’ve gone from one to three. Most companies who have our kind of annual revenue have two or three times the amount of people focused on growth.

For us, it’s now automation. How can we continue the same baseline that we had last year, which I think on average was about $35,000 a month in net new revenue growth. How can we continue that with less time, with less energy, and then what strategies can we then layer on top of that?

Last year, we were very focused on webinars, so we’re going to have that same focus in 2017. But on top of that, we’re going to add in a new layer or promotions that we didn’t do last year. Then we’re going to do a new layer of inbound marketing that we didn’t do last year. Right now, our big focus is we’ve created two inbound lead-generating channels for direct sales of high-tier customers. That’s actually beginning to earn as much or more than our webinar channel last year.

It’s a matter of then creating this channel with webinars. I feel like we mastered it last year. So then how do we automate it, and then what’s the next layer that we stack on top of that? We’re not going to give up on this strategy. The strategy is going to continue to perform for us. What’s the next layer, what’s the layer after that, and what’s the layer after that to begin scaling it?

Sean Jackson: I think that it’s fairly true with most SaaS businesses. You kind of start out small, and then as you continue to find that growth and things that work, then you’re starting to look more up market. Because as you were saying, you’re looking at these channels, these inbound channels, for people who tend to spend more. That is now another layer you’re adding on top.

But I think this is the important part of what you said. “Okay, we did the webinar a bit. Okay, we’re done with that. Now let’s go over and do this thing, and let’s go do that thing.” In other words, everything, it sounds like, you guys are stacking one on top of the other as you become proficient in it to continue that systematic process of continuing the growth cycle based on expertise on these different stack layers. Would that be a good way to sum it up?

Darrell Vesterfelt: Yeah, absolutely, and the other thing I’m learning, Sean, too, is stacking is huge. The other thing I’ve learned is this niche is way bigger than we could’ve ever guessed to begin with. I just had a meeting last week with a guy who would be one of our biggest customers to date, and I realized after talking to him there are layers in our niche that we don’t even know exist yet.

Every day, the more that we explore, the deeper that we go into this niche, the more we realize that we’ve been very shallow. We’ve been very shallow in our understanding of who we can serve as a blogger because there are layers of bloggers that we didn’t even ever knew existed that doors are opening up to, and we’re like, “Oh gosh.” We thought this was like $10 million a year kind of space. We think it might be $100 million a year space now.

The more that we’re stacking, the more that we’re kind of diving into discovering the different layers. It’s like an onion — layer after layer after layer after layer of people who would consider themselves bloggers in some ways. It’s just a bigger market than we could’ve ever, ever guessed. The stacking has allowed us to dive into that.

People who are interested in doing affiliate marketing is just one layer, it’s just one layer of potential customers or potential leads that we could gather. As we start stacking these strategies up, we’re finding, “Oh my gosh, there’s 10,000 new people here that we could chase down who are doing different kinds of content creation online.”

Sean Jackson: Darrell, I can’t thank you enough for being on our show today with us and sharing this great insight. It is truly fascinating watching the growth of ConvertKit, to see the things that you guys have put together. I love the fact that you guys said, “We are going to be one thing, and we’re going to be really good at one thing for one group of people.”

As you just ended our conversation, you will be surprised that, that one of group of people is much bigger than you ever thought. Darrell Vesterfelt with ConvertKit, thank you so much for being on our show.

Darrell Vesterfelt: Thanks, guys.

Sean Jackson: Hey, everyone. This is Sean Jackson, the host of The Digital Entrepreneur, and I want to ask you a simple question. What is your business framework for selling digital goods online? Now, if the question perplexes you, don’t worry — you’re not alone. Most people don’t realize that the most successful digital entrepreneurs have a framework or general process for creating and selling their digital goods in the online space.

One of the best free resources is Digital Commerce Academy. Digital Commerce Academy combines online learning with case studies and webinars created by people who make a living selling digital goods online. The best part is that this material is free when you register. Are you interested in joining? Well, I’ll make it easy for you. If you are listening to the show on your phone and are in the continental United States, I want you to send a text message to 313131 with the keyword ‘DIGITS.’ When you send that text message, we will send you a link to the registration form right to your phone.

Are you outside the United States? Don’t worry. Just send us an email to Digits@Rainmaker.FM. Either way, we’ll send you a link to the registration form so that you can sign up for free for Digital Commerce Academy, and as a special bonus, we will also subscribe you to our newsletter when you text or email us so that you can stay informed with the latest insights from the show.

And don’t worry — we respect your privacy, and we will not share your email or phone number, and you can easily unsubscribe at any time. If you want to start building or improving your framework for selling digital goods online, then please send a text to 313131 with the keyword ‘DIGITS,’ or send us an email at Digits@Rainmaker.FM. You won’t be disappointed.

Two Sites You Should Be Looking At This Week

Sean Jackson: Welcome back from the break, everyone, and as usual, Jessica and I, we’re going to share sites and tools that we think you should be looking at. Jessica, what is a site or tool you think our audience should be taking a looking at this week?

Jessica Frick: The one that I want to recommend as a case study is theSkimm — is a daily email that I mentioned earlier in the show that basically summarizes the days and news. They offer cool tips and things of that nature.

The interesting thing that I love about this is, number one, they write it like a friend. Every day I get the email — and it’s just the highlights with links to more information — and it’s written in that familiar, casual tone. But it’s about important stuff.

Number two, I love that they have experienced most of their growth through referrals. As a matter of fact, in the show notes, I’m going to be including my referral link. I don’t get paid for it, but they make it fun. They gamify it, and I totally want to get more points.

Number three, I love that they have a freemium and a premium model. I actually do pay the $3 a month to have app access, so I don’t always have to stick to just my email. And I get their cool calendar.

Sean Jackson: Really? Wait, wait, wait — they charge you extra for the app?

Jessica Frick: They do.

Sean Jackson: Wow, that’s cool.

Jessica Frick: They do. It’s just a few bucks, but what’s interesting is they don’t just make their money off of the monthly iTunes subscription. They do have advertisers, and the way that they handle the advertisers does not detract from the content, which I think a lot of people don’t do as masterfully as they do.

Sean Jackson: Very cool. That sounds something good to look at both as a case study, as well as something to entertain you for the day.

My recommendation is a site I just ran into, and I am totally blown away. If you are someone who writes online and you’re getting writer’s block or you are someone who really cares about the SEO copywriting space, there is a site called It’s done by a company in the UK, I believe. It’s called

What you do is, you put in your idea — let’s say you want to write about jewelry — and what it does in a very graphical and intense way is give you meaningful queries from the search engines people are using based on that term. But it’s different in so far as they upend information to it — like who, what, when, and where. What kind of questions are people asking? What type of prepositions are people using? I highly recommend it.

If you are really wanting to write SEO content or maybe a headline or a subject line for an email newsletter, then looking at how people are asking search engines questions may be something that you could use in your subject line or in the beginning of your email copy and then answer it therein., we’ll definitely put a link in the show notes. Again, I don’t have a fancy referral link like Jessica does. I just like it.

Jessica Frick: I love the idea because, finally, there’s a way to do this without the spammy side of Quora.

Sean Jackson: Yeah, yeah, exactly. Now, there’s a guy on their site, he’s a scary looking guy, so don’t be freaked out by the video they have. Just put in a term, pick your country — default’s the UK, you can do US — hit “GET QUESTIONS,” and you will see a beautiful graph as well as the raw data. It’s upended by questions and prepositions so that you can really zero in on some headlines.

All right, that’s our two sites — and Take a look at them this week.

Question for the Week: Is Affiliate Marketing Worth Your Time?

Sean Jackson: Jessica, to end the show, what is the question of the week we’d like people to ponder until our next episode?

Jessica Frick: Well, talking about my Skimm’bassador link — again, I don’t get paid for it, I just get cool points — it made me think about affiliate marketing. Sean, you and I have talked about this, but I would like to know your current position. Do you think affiliate marketing is worth it for digital entrepreneurs?

Sean Jackson: Too hard, too hard. Forget about it. It’s too hard. Can’t do it.

Jessica Frick: You think that affiliate marketing is too hard?

Sean Jackson: Yep. Too hard, too little return. What do you say?

Jessica Frick: Oh my gosh, of course I disagree with you, big time. You wanted a controversial one. This one, I will die on this hill, Sean.

Sean Jackson: I will say this that this is a question that will take more than the few seconds we have left, and we will absolutely cover it in the next episode of The Digital Entrepreneur. Everyone, have a great week.

Jessica Frick: Thanks for listening.