Optimize Episode 010: Jimmy Daly on Founding Superpath, the Largest Community for Content Marketers, and How to Create Fantastic Content

Learn More About Jimmy Daly

LinkedIn: https://www.linkedin.com/in/jimmydaly/ 

Twitter: https://twitter.com/jimmy_daly 

Website: https://www.superpath.co/ 

What to Listen For:

02:14 Jimmy’s background 

03:27 What is Superpath?

06:38 What goes into creating valuable content?

08:09 How to find talent to execute your content strategy

12:38 Should experts be writing our content?

14:06 Superpath’s freelance writer marketplace

15:40 Jimmy’s thoughts on AI content

17:11 How much should a piece of content cost in 2023?

21:32 How to plan a content strategy for the first two years

25:14 Content strategy KPIs and goal setting

28:15 Creating content for each stage of the funnel

30:31 How often should we revisit and optimize content?

32:13 Best practices for content marketers in cross-functional teams

34:32 Jimmy’s lessons learned from starting a Slack community

39:27 Lightning question round

Episode Transcript

Jimmy Daly (Speaking)

00:00

There's a good way and a bad way to do it. The bad way is to turn your content team into an internal agency that just serves other teams' needs. And that's actually really common. The good way to do it is to treat content as a growth function and to lean on other teams as sources of inspiration and subject matter expertise for the content you're doing. The most important teams I think you should be working with are sales and then either support or success — just because those are the folks that are on the front lines with customers and have oftentimes the best understanding of the very acute needs of people who pay you money. Leaning on other folks to create better content is fantastic. Just working for other teams is not a great setup, and oftentimes leads to a lot of frustration because then somebody, some exec, is going to be like, “How come the traffic's not growing? Like, how come we're not getting MQLs?” And then when they dig in, it's like the content team isn't even working on that stuff anymore. 

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Nate Matherson (Speaking)

Hi and welcome to the Optimize Podcast. My name is Nate Matherson, and I'm your host. On this weekly podcast, we sit down with some of the smartest minds in content marketing and SEO. Our goal is to give you perspective and insights on what's moving the needle in organic search. Today I'm thrilled to sit down with Jimmy Daly. Jimmy is the co-founder and the CEO of Superpath, one of the largest professional communities for content marketers. He's a longtime B2B content marketer himself, and he's previously worked on some amazing teams including at Vero, QuickBooks, and Animalz. Jimmy is also a fellow Blue Hen, and in our episode today I'm excited to learn more about the work he and his team are doing at Superpath, his perspectives on creating fantastic content, measuring the success of a content channel, and to get an inside look at what it takes to manage a very large Slack community. 

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Ad Spot

This episode of the Optimize podcast is brought to you by Positional. At Positional, we're building tools for content marketing and SEO teams. We've got a great selection of tools for everything from content optimization to keyword research and technical SEO, and you can visit our website at positional.com. 

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Nate Matherson (Speaking)

Thanks so much, Jimmy, for coming on.

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Jimmy Daly (Speaking)

Yeah, absolutely. Looking forward to chatting. 

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Nate Matherson (Speaking)

Yeah, so the first question I always ask our guests is, how did you get into the world of content marketing and SEO? Like, what led you to ultimately starting Superpath? 

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Jimmy Daly (Speaking)

02:14

Man, I wish it was a really exciting story. I was an English major at University of Delaware. I left school with no clue what I wanted to do, and a family friend at a barbecue — I got to talking with him, and he was running an SEO agency. He said he needed some writers, and would I be interested in doing some freelance work. And I thought that was pretty cool to be able to get paid to write. I really had never considered that outside of, like, maybe journalism. So I started doing some freelance writing work for his company, and it was SEO for lawyers. So the stuff I was writing was, like, you know, like, how to find a DUI lawyer in Topeka, Kansas — like, stuff like that. And I think I got paid — I think the articles were probably about 300 words each; I think I got paid about 30 bucks for each of them. Could crank them out in, you know, 10 or 20 minutes each. So it wasn't really that exciting. Actually later went and worked for that company full-time. And that's when I kind of really got into SEO and content marketing and just kind of opened my eyes to this world, which started as, like, hey, I'm an English major, I can write a little bit. I could — maybe I could get paid to write. And then very slowly and over a long period of time turned into this, you know, kind of, like, what we know of as content marketing today. For me, it was pretty much all B2B SaaS, but it was slow — it was slow, slow start, inauspicious for sure.

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Nate Matherson (Speaking)

03:24

And tell us about Superpath. What have you built? What are you building from here?

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Jimmy Daly (Speaking)

03:27

I started Superpath actually as a side project about four years ago, and a just Slack community because I just wanted a place to chat with peers. And I kind of noticed this trend of people forming professional groups on Slack. And so I spun one up and invited a few folks to join. This is, like — I guess it's 2019. And it was like, at the time, not everybody was using Slack to chat with people outside of their own coworkers, you know? So this sort of, like, cross-organizational chat thing was fairly new for Slack. And I was really excited because I was — so I was working at this agency, Animalz, and, like, I invited a bunch of our customers, and I invited a bunch of other peers in the content marketing world, and, you know, maybe it was 20 people to start, and we were just talking and sharing, you know, kind of sharing notes, asking each other for ideas and stuff. And it was really cool. It was really powerful. That, about a year later, turned into me leaving my job to pursue it full-time. So I've been running it for — I've been running it full-time for three years. We run the Slack group, we run a job board, we run a paid membership, we run a partner program, and we run a marketplace where you can, where companies can find freelance writers. A lot has happened over the past couple of years, but really all of it has just kind of started with the community. It's still in many ways built around the community. Like, it all works and functions because we have all these really smart content marketing people in one place. 

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Nate Matherson (Speaking)

Yeah, it's a fantastic group. Highly recommend all of our listeners check it out after this episode. And I've learned a lot being part of it. There's a lot of great conversations happening there. And another question I have is, I was looking at your background, and you've spent some time on, like, in-house teams and then ultimately went to, like, the agency side of things, at Animalz. Looking back, like, did you prefer, like, working on an in-house team, or did you prefer, you know, that transition into the agency side of things before Superpath? 

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Jimmy Daly (Speaking)

You know, honestly, I liked both. I actually wrote a blog post about this idea, which I call expansion and contraction. And I found that, in my career, I would go through phases where I really wanted to go deep. That was my in-house time: like, I wanted to focus on one business, one blog, really go deep on that one thing. And then after a couple years, I'd find myself wanting to go broad. And that was when I would make a switch to an agency. I did this six times, going back and forth. I did two stints at Animalz, I worked at a different agency, and then I worked at two SaaS companies. So I guess five times total, actually. And I just found that kind of like zooming in, zooming out, zooming in, zooming out was a cool way. I mean, I don't wanna make it seem like this is really well thought out. I sort of realized this in retrospect, but it was like I find myself wanting to go deep and then wanting, like, exposure to lots of different companies. Then go deep, then wanting exposure. And interestingly, I find that people do that in different ways in their own careers. I feel like it's a pattern. It's not always in-house, agency. For some people, it's, like, small company, big company, you know, or it's like one-person marketing team, 50-person marketing team, or whatever. And they sort of go back and forth because, you know, there might be things you like about each, but you can't get all of it in one place. 

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Nate Matherson (Speaking)

And at our company, we work with a lot of startups, and they always ask me how to get started with building, like, a content marketing channel. And oftentimes it's, like, the founder, like, going out and starting to build this channel. Sometimes they have a single-person marketing team. They ask me to get started. And I always tell them, like, the first two things are to, you know, pick the right topics and the right keywords. And then the second thing is to create fantastic content. And then they always ask me, like, “What is a fantastic piece of content?” I often have, like, a hard time defining it, and so I'm going to ask you: In your career, like, what makes, like, a fantastic piece of content, and how do you know that it's actually, like, truly helpful for that reader?

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Jimmy Daly (Speaking)

06:38

Yeah, that's a good question. I think that during my time at Animalz, which is a content marketing agency, which I joined pretty early. I think I was probably, like, the seventh or eighth employee there. We thought about this question a lot because we were trying to do exactly this for a lot of our clients. And I felt like I had done it at in-house jobs I'd had, but I'd never really verbalized exactly what it was that I was trying to do. We kind of boiled it down to what we called alpha. So a great piece of content has alpha, meaning it has information or data in there that you can't get anywhere else. That always was the most important thing. Sometimes that literally was a data point, which you might've gotten from doing some kind of analysis or running a survey or whatever. Sometimes it was an idea or a concept that you kind of took and made your own, made it proprietary. Sometimes it was the format of the piece that was novel and folks hadn't seen before. Whichever of those things it was, and there's probably a couple other things that might fit the criteria there, it had to be — it had to contain something that was exclusive to that single piece of content. That's the biggest thing. Not every single piece of content that every SaaS company puts out is gonna be able to have that, because there's a limited amount of alpha. But that is, to me, the thing, the single thing that would separate, like, a truly great piece from just an OK piece. 

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Nate Matherson (Speaking)

And as far as creating content goes, I know you've got the marketplace as part of Superpath. But a question I'm always asked is, like, “How do I find people to write content for me?” Either, like, a full-time person or a freelancer or an agency — like, if I'm a startup founder or, like, an early-stage team, like, how do I go about finding, like, talent to actually help me build out this portfolio of content?

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Jimmy Daly (Speaking)

08:09

Yeah, Superpath, that's right, you should just come to Superpath; we can help you. I mean, actually, what I'm finding is that one of the things that's happened over the past couple of years is that as the business has grown, I kind of describe these different lines of business that we've spun up, and while they are all loosely tied together by the community, I'm trying to narrow in on a vision that is much more cohesive. And I think that that cohesive vision is all about brokering the relationships between the demand and the supply, the people who want content and the folks that can provide it, regardless of whether they're 1099, W2, agency, or consultant, or whatever, fractional or whatever. We do a ton of that through our job board. It's happening organically in the Slack group. We do it manually through the marketplace. And I'm actually — we're in the early stages of building out a simple web app where anyone will be able to log in and browse freelancers. I aspire one day for Superpath to look a lot like what Dribbble looks like for designers — where, in that case, a designer can make an account, host a portfolio; on the backend, there's a bunch of data that allows people who want to hire designers to filter and sort and reach out and message and that kind of thing. So that's what I'm working on right now. I'm not a developer. So the first version of it is going to be pretty simple. Without that, all you have is Upwork, which is not good unless you want really cheap content. There's social media, where you can just go and ask people for recommendations or kind of your own network. You can ask peers. There's other Slack groups, but all these — the market for this type of thing is very, very fragmented. And I really would like to bring all of it together so that the demand and supply have one obvious place to meet and transact. 

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Nate Matherson (Speaking)

Yeah. At our first company, we started, I think, like, the first three or four years by managing, like, a freelance writing team. We eventually, like, brought it all in-house. We had, like, full-time writers and editors as part of our team. When does it make sense for a company to, like, freelance out this job or the content creation process, versus, like, making a full-time hire and bringing someone in internally? 

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Jimmy Daly (Speaking)

Yeah, that's a really interesting and difficult question to answer. There's actually been quite a bit of upheaval in the space recently. Content marketers have gone through a pretty tough time over the last four to six months. And a lot of that has been companies moving away from having in-house content marketers to a model where they rely primarily on freelancers. There's some obvious benefits to that, which is that it's cheaper. It's a lot cheaper to hire freelancers to create content than it is in-house employees. It's also frees you up of the fixed costs, right? So it's a variable model rather than fixed. There's pros and cons here. I think that if I was going to offer broad advice, what I would probably say is, you need to have at least one person on your team who really understands content, so that if you're going to work with freelancers or agencies or consultants, that that person can run the show, keep all those people moving in the right direction, make sure it's all working like it's supposed to, be the kind of quality control to make sure the stuff is actually really good. If you don't have at least that one person, the results are gonna be basically like a lottery. Like, maybe it'll work, but, you know, probably not unless you have someone really tightly managing all that. And then for some companies, it does make sense to bring on a big team. Like, I was actually just recently talking with the folks at Zapier. Like, they have 20 people on their content team. That's crazy. That's a lot of people. You know, I can think of a hundred SaaS companies that have one, you know, and then, but they have a huge output because they rely on team of vendors. So I think it's really dependent on the company, you know, how important content is to them, kind of the life cycle of the company, too. Like, your early stage, like, you know, before series A, like, one person plus some freelancers is great. By the time you get to series B, like, you probably need to have five, if not more, full-time people on your team doing content. 

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Nate Matherson (Speaking)

Yeah. And Upwork can definitely be hit or miss. I actually do like Upwork, but with my experience on Upwork, you typically have to hire, like, four people for every job and then ultimately, like, pick the one that you want to, like, keep working with. So yeah, it does take, like, some time to get up and running on Upwork. But the one thing that I've liked about Upwork is that you can surprisingly find some, like, really smart and, you know, people with actual expertise in the topics you want them to write about. Like, so for example, at, like, our first company, we had a lot of content about pet insurance, and we actually were able to find, like, veterinarians on Upwork who would write content for us. Or for example, like, a financial advisor to find — you know, to go and review a piece of content. And so I have had some success. I guess where I'm going with this question is, if I am going to hire a freelancer to help me write content, like, how important is it that that person actually is an expert in that space or the category? Do they need to be an expert or is that just, like, a nice to have?

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Jimmy Daly (Speaking)

12:38

I think it depends on the type of content that you're doing and how technical the subject matter is. So, like, an example would be — I'm trying to think of some of the customers that we work with. Like, we work with one company who does commercial lending. They really needed someone with some existing financial expertise to do this. It was just gonna take way too long to ramp someone who's a good writer with no background in this up to speed so that they could do the work. You know, on the flip side, one thing we do with all of the content that we create through the marketplace, too, is that 20-minute Zoom call for every piece. So we pair up the writer and a subject matter expert internally at the company to talk about the article. And that gives the writer so much to work with. It's kind of — it's a, I would say it's a necessary step if you're working with a writer who does not have, like, hands-on experience with the thing that you're writing about. So I feel like there's just, like, a spectrum of it. You know, like, some content is just way too technical. Like, if you haven't done it, and I'm thinking of, like, content for developers — like, you can't fake it. You, like, if you can't cite the code snippet and test that it works, you can't do it. And then on the other end there's, like, sales and marketing-type content, which like anyone could do; it doesn't mean it's gonna be good, but anybody could do it and make it look like content should look. 

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Nate Matherson (Speaking)

Yeah, finding freelancers who can write in, like, the developer's whole space is very challenging. I spent, like, two years in, like, the observability software space, and it was very challenging to build that team of freelance writers and then also to edit that content to make sure that it was accurate from, like, a technical point of view. With your marketplace, which categories or, like, which verticals can you support or what verticals do you typically focus on with your marketplace business?

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Jimmy Daly (Speaking)

14:06

You know, that's interesting because part of what we do is fill subject matter expertise gaps for companies that typically have trouble finding freelancers. So because we have — the Slack group has 16,000-ish people in there, and that's essentially our pool of writers that we're working with. So unless the content is just extremely technical, we can probably do it. You know, so, like, I put out a call to see if we had anyone who had written about commercial lending. Sure enough, we had five or six people. Two of them were fantastic, you know? And any time we work with a new customer, I do that as part of our sales process. I just kind of do a gut check and see, like, do we have someone who can do this? Almost always the answer is yes, because there's a lot of people in there. And we sort of do that to, like, vet that, OK, everybody feels excited about this deal before it actually goes through. We don't do content for developers. I tried briefly; it did not work. I have a friend actually that I worked very closely with at Animalz who left and started his own agency, and that's all they do. So I just refer people that way. Interestingly, this is a total side note, but I was with him in New York last week. He was showing me some ChatGPT hacks for writing content for developers, which I was super impressed by because ChatGPT can essentially write all the code. If you're anything that any content that requires you to cite code, it can write it for you. You just test it, and then you can include it. And he said that’s saving him about 50% of the content creation time because he doesn't have to write code out line by line any longer. So total side note, but I thought that was kind of interesting.

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Nate Matherson (Speaking)

15:28

Well, I wasn't going to ask you, but now I have to, like, what should we make of, like, AI-generated content? Should we be using it? Like, is that a good strategy for, like, either a startup or a later stage company even? 

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Jimmy Daly (Speaking)

I think you just have to be testing it, and you have to be looking for ways to get yourself an edge. You know, 10 years ago, or probably more, probably more like 15 years ago, SaaS companies were like, “Should we really bother with content?” Like, you know, it's sort of like a thing that a lot of companies were testing out, sort of unsure of whether or not it was worth investing money in, I guess, what then was called inbound marketing. Nowadays, it's like, of course you do content, it's just a matter of, like, what type or how much or, you know, what does it cost, or whatever. And I feel like down the road, it's going to be the same thing with generative AI. It's like, at the moment, we're in this sort of discovery phase of, like, what do we do with it? You know, it won't take 10 to 15 years, that's for sure. It'll probably take, like, one or two years before it's become just so commonplace. There's just, like, a playbook for it, like there is for B2B content marketing now, you know, just be much more established. But I feel like now is the time where, like, I don't really know exactly what you should do with it, but there's almost certainly some things that could at the very least save you time, if not give you an edge when it comes to creating better content. Yeah, I don't see — I'm super excited about it though, to be honest. Like, I went from, like, afraid to skeptical to, like, lukewarm to now really excited. 

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Nate Matherson (Speaking)

Yeah. Well, I think, like, if you're using AI, my opinion at least is to make your content more helpful and, like, more actionable and more valuable for the reader, then I think, like, Google would say that that's a better piece of content. I think that what you shouldn't be doing is probably copying and pasting, like, a 1,500-word article from ChatGPT onto your site without putting it through an editorial process first. But I'm gonna ask you two, like, broad questions, and they're intentionally broad. What does it cost to create, like, an awesome piece of content in 2023?

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Nate Matherson (Speaking)

17:12

I can tell you exactly what it costs if you use a freelancer. I think that if you are going to be creating it in-house, it costs more than you think it does. You know what I mean? Like, I think through the marketplace, we charge for a 1,200-word piece of content about $1,200. We're getting some really good stuff back. You could pay 500 bucks and get something not bad. You could pay $2,500 and get something really, really amazing. I feel like one thing that's happened is that there's so many good writers out there now. You know, like, within our Slack group, for example, like, anytime I put out a call for writers, I get tons and tons of people, and most of them are really good. The challenge there for the freelancers is, like, the market is full of good talent, you know, so content is actually relatively inexpensive right now. Just because of where we are and, like, what we, what we in the Slack group are calling, like, the content recession, which I think is actually almost over, but you know, so many folks got laid off in the content space. A lot of people ended up becoming freelancers, you know, not by choice. And so, like, there's just tons and tons of good people out there; that's actually pushed prices down on content, on good stuff. That will change. Like, I do expect that to shift. But I also think that 1,000 bucks, you're going to get a really great piece of content for, like, 2,000 to 3,000 bucks for a piece, like it should be like really, really top-notch. You know, then if you're doing it in-house, that's a whole different thing. It's very difficult to kind of, like, analyze what is the cost of a piece if it's done by an in-house employee. It's probably a few thousand bucks minimum. 

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Nate Matherson (Speaking)

Yeah. And I saw you post about the content recession on LinkedIn. And if you're not already following Jimmy on LinkedIn, you should be. I want to take a step back to, like, 2021. Were things just gangbusters? Was demand, like, you just couldn't keep up with it? 

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Jimmy Daly (Speaking)

Gangbusters. It was awesome. It was great for everybody. Like, 2021 was fun. We had — I mean, 2021 is when I spun up our marketplace because I was like, “There's just demand everywhere. There's all these great writers; like, let's do something here.” It was really, like, a nice mix. Like, I never had trouble finding good writers to do the work. And I didn't have trouble finding SaaS companies who wanted content. Just like, everything was just working so nicely. And then that, you know, like, 2022, that started to change. Like, 2023, it changed big time. 

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Nate Matherson (Speaking)
But things are getting better. You're seeing more companies want to invest in content now than you were maybe six months ago?

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Jimmy Daly (Speaking)

Yeah, I think things are opening up a little bit. You know, like, anecdotally, just I talk to a lot of content marketers. So, like, I don't have, like, good — I don’t have data. I can't tell you, like, X percent of this or Y percent of that has happened. But one thing we saw was that content agencies got hit really, really hard spring 2023. I can't exactly explain why. I think it's, like, some mix of economic uncertainty; ChatGPT is definitely a factor. And it just sort of, like, culminated in this, like, “do more with less” trend that everybody was, like, super hot on. And agencies seem to be hit hardest — I think because companies are looking around at ways to cut costs, and agencies are just, like, an obvious one because they're expensive and replaceable. In-house teams felt it, too, though. But what was happening is that, like, a lot of these companies were just producing way, way less content than they typically were. Part of the strategic thinking there, I think, is that content has a half-life. So if you turn it off, you don't feel the impact right away, you know, and so they could kind of give themselves a little bit of breathing room, and then decide, like, do we pick it back up later? And we are seeing the “pick it back up later” starting to happen now. So, like, it's kind of like April, May, things are going really badly, you know. Now it's, like, late July, things are starting to open back up. Again, just anecdotally, July's been a good month for Superpath, whereas, like, May and — April was OK, or May was a disaster. June was a disaster, and now July's sort of starting to get back on track. So to me, that's, like, the most important indicator, but I'm seeing and hearing a lot of the kind of similar things as I talk to other people.

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Nate Matherson (Speaking)

Yeah, well, the half-life you mentioned is, I don't even know that it's a half-life, if done correctly, or it's at least a really long half-life. And that's one of the reasons I love content marketing and SEO is, like, you do a lot of upfront work and building, but if done correctly, like, it's gonna exist for 10 years. Like, of course you wanna come back and update the content and make sure that it's accurate. But that's how I always sell content and SEO to, like, our prospective customers who are thinking about it but maybe lukewarm, and, like, we're not an agency. But I like to say, like, you're building kind of an asset to your business that's gonna be valuable forever onward if you do it right. You mentioned cadence. So I wanna come back to that. Question I'm always asked is how much content should we be creating? So I know that's also a very broad question, but say for example we're, like, a Series A company, we just raised 15 million bucks, we wanna build a content marketing channel and we're serious about it. Like, how much content should I plan on creating in the next year or two years?

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Jimmy Daly (Speaking)

21:32

Yeah, that's a great question. I think that all content strategy should be a subset of go-to-market strategy. So it depends quite a bit on the business model. And I can give you a few different examples. I ran our marketing at Animalz content agency. We did one blog post a week, if that. I mean, maybe it was twice a month sometimes. All very thought leadership-y type stuff. It did not get a ton of traffic, but it drove awesome, awesome deals for us. And I sort of say —  that's not the Series A example you cited, but I say it just to sort of illustrate the point that, like, it's a low-volume business. Like, we only need to close one, two, three deals a month and we're growing faster than we can keep up with. And so, like, that content strategy worked really well for that business. To use an example of one of our customers right now, their pre-seed SMS for business, one of the challenges that they have is that they have at least 15 different core personas that they need to reach, all sort of SMB personas, and then they have a bunch of different use cases. And when you multiply those two things together, you get thousands and thousands of potential topics to write about. So that's what they're doing. Like, they're working through a really massive list of search-optimized content to try to match up persona-use case, persona-use case. And like that list is — it's not exactly infinite, but it's gonna take a while to work through. If you were to compare that against, like, an enterprise SaaS company, where, like, annual contract values are fifty or a hundred thousand dollars a year, or in some cases quite a bit more, cadence doesn't really matter that much. Like, you should be working on sales enablement and social proof and, you know, like, feeding your reps stuff that's gonna help close deals. And then Zapier is an interesting example, too, where, like, I spoke with their content team last week and they create 85 articles a month. I think that's a lot. I think if I had to offer something a little more general, I would say, like, if you can get two articles a week out the door, that's pretty good. I think most teams can probably handle getting two articles a week out the door. I would say basically every team probably already knows, like, what topics are absolutely essential to cover and could probably build out a three- or six-month content calendar pretty quickly. And if you stay on that two-article-a-week cadence, you know, you're moving quickly enough that you're sort of taking some chances. You know, you're, like, seeing what works, you're iterating quickly, you know, you're updating stuff if it's not working, you're swapping out ideas if you're not, like, getting the sense that readers are excited about it. But I feel like twice a month is, like, a reasonable cadence for most companies who are willing to make a, you know, like, a somewhat significant investment in content. 

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Nate Matherson (Speaking)

Yeah. I mean, in a year from now, you're going to have 104 awesome pieces of content. And so I think that's a great cadence. I always recommend to our customers, like, once a week and just commit to it. Like, of course you can do more than that. Like, at our first company, we were creating, like, 75 articles a month. We had, like, a full-time team of, like, seven or eight people. But we ran into that kind of multiplier effect, which you were describing, because we were in very different verticals, like car insurance and investing products and home equity loans. And when you multiply those categories by, like, all of the different states and all of the different cities and all of the different reviews you could write, like next thing you know, you can write 2,500 articles, no problem. 

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Jimmy Daly (Speaking)

Yeah.

Nate Matherson (Speaking)
But at, like, the last company that I worked at, you know, we were in an observability software space. And there was just, like, clearly 200 articles that needed to be made. But, like, beyond that, like, we just couldn't find them.

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Jimmy Daly (Speaking)

Interesting. 

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Nate Matherson (Speaking)

24:43

And so, like, you know, if we were to spend two years creating two posts a week, like, we would have covered that entire spectrum of topics that I thought we needed to cover. You know, speaking of, like, KPIs, so now that we've, like, created the content, we've gotten the cadence set up, we've got the editorial calendar kind of mapped out, and we've spent maybe, like, let's call it $120,000 this year on content if we've done it through the Superpath Marketplace. How do we then, like, show, like, our boss or, like, our team that, like, it's working and, like, that this is actually a worthwhile investment to do again next year?

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Jimmy Daly (Speaking)

Yeah, yeah. Very important question. I think there's sort of two things that come to mind. One is that there's a couple different data points that I think could tell the story, but I think the most important thing is that everyone agrees on what those data points are. One thing I see a lot and that you really don't want is for the content team to be looking at page views and for the exec team to be looking at SQLs. And the content team being like, “We're crushing it.” And the execs being like, “No, you're not.” You know, that happens quite a bit. So I feel like it's important that a content team is communicating well with leadership, you know, whether it's a VP or a CMO, or in some cases even a founder, to — probably it's MQLs, is like the business metric that they should be looking at. An MQL is, you know, loosely defined as, like, an email address, you know, through a content upgrade, a newsletter subscriber, and a few other things. You know, then you have your SQLs, which are more like demos, trial signups, stuff like that. The MQLs are, like, a pretty good indicator generally of how much content is assisting in getting people closer to the product. And then obviously there's all your content metrics. So, like, if your strategy is primarily focused on SEO, like, you wanna be looking at organic traffic, but you really wanna be looking at it month over month as opposed to an absolute number. So, like, you get 10,000 organic visits a month, you're thinking about, like, OK, can we generate five to 10% month-over-month growth? And if you model that out for a year or two, that's starting to look really nice, you know? But I'm a big fan of relative APIs rather than absolutes. And then the other thing that I think of is anecdotal reporting. A friend of mine, Sean Blanda, who runs content at this company called Crossbeam, calls this “building an art museum.” Basically, it's just like taking screenshots anytime someone says something nice about your content. You know, whether that's a sales rep saying, like, “Hey, this helped me close a deal in a Slack channel,” or whether it's someone who, like, really nicely fits your target persona posting about it on Twitter or LinkedIn or whatever else, but it's very important to have a name and a face attached to it. Take all those screenshots and build that into your reporting, too, because one thing I have definitely noticed is that, like, using Animalz as an example, like, we're writing — say we write two blog posts in a month, and they generate 500 total page views. You could look at that and be like, “Well, that sucks. Why are we wasting our time?” But, you know, if I could get a screenshot of a VP of content at a company saying like, “You know, this article articulated something that I've never thought of, and it's, like, totally changed the way I think about content marketing,” like, that's incredibly, incredibly valuable. So, like, the numbers don't really tell the full story, and small numbers don't necessarily mean that the content isn't resonating with the people that you want it to resonate with. So I'm a big fan of names and faces in addition to the data. 

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Nate Matherson (Speaking)

Yeah, I always say page views don't equal dollars. At my first company, they did. So, like, the more page views we had, the more dollars we had. At my second company, it did not. Page views definitely did not equal dollars. And we found that, like, certain pages would generate, like, a lot of page views, but no dollars. And then other pages would generate very few page views and a lot more dollars. Speaking of, like, the funnel, like, how do you go about, like, creating content across, like, the different stages of the funnel? Should we only focus on, like, that down-the-funnel-content, or is it still, like, worthwhile to cover even, like, an evergreen piece of content? Like, what is XYZ? How do you think about that?

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Jimmy Daly (Speaking)

28:15

I also would start with the business model. You know, like, say your product costs $20 a month per user and you're using a product-led growth approach, meaning, like, you're primarily driving people to a free trial or a freemium version; you need a lot of volume in order to make that work. So you're going to need to do probably quite a bit of top-of-funnel content in order to get enough people on the website to make the math work, right? Like, if you're going to drive, like, one- or two-percent conversions, you're going to need a ton of people on the site to make it all work. So in that case, it's like the approach would be, like, if you look at — if you've made, like, a pie chart of, like, top-, middle-, and bottom-of-funnel content, you know, maybe half of it is top of funnel, a quarter is middle, a quarter is bottom. You know, and, like, that pie chart starts to look different based on the type of business. So, like, if you look at enterprise SaaS, you know, maybe top of funnel is 10%, you know, and then middle of funnel is 40%, and bottom of funnel is 50%, or something like that. One of the things we did for some customers at Animalz is we would do these things called funnel depth audits, where we would export all their content into a spreadsheet and then tag it as top, middle, and bottom of funnel, like, based on some criteria that we came up with. The reason that we did that is because we were just sort of noticing that a lot of companies were kind of over-indexing on top-of-funnel content, and then getting frustrated that their content investment wasn't turning into customers. And it was a really easy way to illustrate to them, like, OK, your pie chart is, like, 75% top of funnel. You know, that's why you got a lot of people on the website and not a lot of people converting. So let's kind of balance this pie chart back out. And, like, that's sort of an easy way to help — especially if you're trying to pitch this to, like, a VP or CMO. It's, like, an easy way to help to, like, illustrate how this could work. And we came up with some templates for, like, PLG template, like an enterprise template, and a few others just so that we could kind of walk through the different scenarios with customers. So that's how I think about it. It's kind of a pain in the butt to do, honestly, to, like, really go deep to figure out, like, what your pie chart looks like. But in my experience, it's generally a worthwhile exercise. 

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Nate Matherson (Speaking)

And how often should we come back to the content that we've already published? Should that be, like, once a year, once a quarter, once every two years? Like, how often should we be going back and reviewing or updating previously published content?

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Jimmy Daly (Speaking)

I think probably every six months or so. I think that, like, a good mental model for content books to think about is your content is probably going to be about 75% net new, 25% refresh. I think that's, like, a healthy mix because there's always new stuff to write about, but you really want to take care of, like, the hygiene, you know — like, all the things that, like, keep the old stuff doing well. So it's refreshing, it's building internal links to stuff that didn't exist when you published the old piece and that kind of thing. But it's really important to get that stuff back on a content calendar. And I think that's where most companies miss on this, is that every now and then they're like, “Oh crap, we have all this old content that needs to be updated.” Say you use — like a lot of folks — use Airtable for content calendars these days. You could just create a simple automation that, like, takes every SEO piece, sets a delay for six months and then puts it back at the beginning. You know, just, like, make sure it's always — you're always kind of, like, remembering that stuff and you can kind of automatically, like, get it back on your radar rather than, like, being — you know, not having a great process around it and being like, “Traffic's going down, what should we do? Oh, let's refresh old stuff.”

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Nate Matherson (Speaking)

Yeah, at our first company, we actually, like, built a software tool that looked — internally — that looked at user experience metrics like bounce rate and scroll depth and engagement rate, and it would compare, like, the performance of pages alongside, like, keyword data to get a sense for, like, OK, is this page a problem? And it would create, like, a ticket system for our editor to go and, like, take another look at it.

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Jimmy Daly (Speaking)

That's cool.

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Nate Matherson (Speaking)

31:49

Everybody has all this data, but it's hard to, like, actually know which pages to go back and focus on in my experience.

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Jimmy Daly (Speaking)

31:56

Yeah.

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Nate Matherson (Speaking)

31:57

As far as, like, working across an org, because I know content can touch, like, multiple parts of a team, whether it's, like, sales or engineering, if you're in, like, developer tools. Do you have any, like, tips or best practices for, like, the content marketers listening on, like, how they can best work across, like, multiple parts of the org? 

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Jimmy Daly (Speaking)

Yeah, yeah, that's really interesting. I feel like there's, like, a good way and a bad way to do it. The bad way is to turn your content team into an internal agency that just serves other teams’ needs. And that's actually really common. The good way to do it is to treat content as a growth function and to lean on other teams as sources of inspiration and subject matter expertise for the content you're doing. So, like, the most important teams I think you should be working with are sales and the other, support or success. Just because those are the folks that are on the front lines with customers and have oftentimes the best understanding of the very acute needs of people who pay you money. So, like, those are the important ones. Where it starts to get a little messier is when a company only trusts the content team to write anything. So, like, they serve as, like, the writing function for the product team. You know. They serve as the writing function for PR, things like that, where, like, it's not exactly the content team's job and it sort of feels like collaboration, but really it probably means that the team is spending time supporting other teams when their own work is getting pushed aside, you know. So I feel like leaning on other folks to create better content is fantastic. You know, just working for other teams is not a great setup and oftentimes leads to a lot of frustration because then somebody, some exec, is gonna be like, “How come the traffic's not growing? Like, how come we're not getting MQLs?” And then when they dig in, it's like the content team isn't even working on that stuff anymore. 

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Nate Matherson (Speaking)

Yeah, I love what you said there. I think in my experience, like, content and AdWords: they can have a great relationship, but I actually think content and customer support is the most important relationship because that's where so many great ideas come from for, like, which pieces of content we should create. You can uncover, like, maybe keywords that actually do get a lot of search volume, but you don't see it in, like, a keyword research tool. And also, just it gives the support team, like, a piece of content to then send to a customer to, like, go and actually learn a lot more. And then, the next question I want to ask you is on the Slack community. Because, like, you're the first guest we've had on that has a massive Slack community. And it sounds like before you started Superpath you hadn't done something like that before. What are some of those two or three big things that you've learned having started and now scaled the Slack community? Maybe they're challenges, maybe they're things that you could have done differently. Looking back, are there two to three kind of big learnings you've had so far?

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Jimmy Daly (Speaking)

34:33

Yeah, wow —  I'm laughing because the learnings have been so humbling. The — so this might be interesting, so, like, at the moment — today's Thursday. Two days ago, we gated the Slack community for the first time. It's been free for four years, since I started it. And we now charge people for access. And that decision was the result of a lot of learning. Like, one of the things that happened as the group started growing was that it was originally created to serve in-house content marketers, and then it started attracting a lot of people. Some of them were in-house content marketers, but it attracted freelancers, it attracted people who weren't content marketers but were interested in becoming content marketers, it attracted some founders — like, it sort of attracted a couple of different personas, and then it started growing really fast. On an average month, we would add 500 people, and we did that for, like, two and a half straight years. And this is like, it kind of, like, accumulated, like, all these people, and the group started getting really noisy. We started having spam problems. Moderation started becoming really difficult, and I started to realize that we weren't able to serve all these different personas. Like, it just wasn't possible for all, and, like — unless we had a larger team. Like, it's just me, so unless we had a larger team to kind of run some of this stuff, it wasn't gonna be possible for us to do that. And I also was starting to get some interesting feedback from members of the group that were saying, like, you know, “This group, I used to like it, you know, but now I don't really use it anymore because it's kind of noisy, and it's a lot going on. And, you know, I just don’t — I have some things I would post, but I don't really wanna post them in front of 15,000 people.” And then alongside that, our analytics were showing that even as we were growing, engagement was actually dropping, which was a huge red flag to me. Like, how could we be adding 500 people a month, but there's fewer active users and fewer posts happening on a monthly basis. So anyways, this sort of all came to a head, like, a month ago, and I was like, “I think that we need to make a drastic change to this group in order for it to have longevity and for it to be a sustainable thing for me to run, especially as just a one-person team.” So we gated it. That's been really hard, to be honest. You know, a lot of people were frustrated about that because they joined the group with the expectation it would be free; now it's not. You know, I'm in some ways starting from scratch. Like, the group has 10 or so paid channels, and we left four or five free as well. So it's not like there's — now there's kind of two groups, but with the paid members, they have higher expectations now because they're paying, and it's a smaller group, so, like, there's not as much natural activity that happens. You know, when you have a few hundred people versus thousands and thousands, like, there's less natural activity. So now I'm having, I’m finding myself having to redo some of the things that I did in the very, very early days to spark engagement and keep people, like, involved and asking questions and things like that. So there's a lot of lessons in there, I guess. One thing that I've kind of committed to is that I try to set reasonable expectations for myself and for Superpath because I am just one person. And so for a long time, I felt bad that I couldn't cater to the larger group. And I've kind of come to the realization that, like, I have to make it so that it's sustainable, so that I can enjoy doing it, so that I can do it for a really long time, rather than, like, drive myself crazy trying to, you know, make it something that, like, I just realistically can't make it be. 

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Nate Matherson (Speaking)

Yeah, I mean, from the outside looking in, it must have been exhausting before you gated it. I'm sure it still is exhausting, but was it just, like, totally exhausting to manage at times, more recently, before you gated it?

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Jimmy Daly (Speaking)

For sure, so actually at one point I hired — summer 2022, I hired a full-time community manager, and she was fantastic. Like, she just did so many things that I never really had time to do. She was a total pro, and she ran the group. It was awesome; like, she was fantastic. And then this is sort of like getting into some of the more business-y stuff, but, like, we got into May of this past year, May 2023, and, like, business was tough, and I unfortunately had to let her go, and it was not a performance issue, which was kind of the worst part about the whole thing. I was, like, you know, looking at our cash flow — we're a small business — and I'm like, “I have to, you know, I have to do something here to keep this business going,” and I had to lay her off. Without her, it could no longer exist as a free community also, because she was managing so much of this stuff manually, which in a community, you just kind of have to do; there's only so many, like, features within Slack and automations you can set up to do good moderation. Like, so much of it is just, like, a person in there doing it. That was a factor for sure that I didn't have her around anymore to help. And so anyways, at the moment, we're only a couple days into the Superpath 2.0, if you wanna call it that. And it's already a lot easier to manage because it's a couple hundred people instead of 16,000. 

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Nate Matherson (Speaking)

Yeah, the barrier of just $20 a month, like, everyone can afford $20 a month, I think, if it's a valuable tool for them professionally. I mean, it's just even that small barrier must weed out, like, 90% of, like, the problem actors too, I would think. But yeah, that's so interesting. And this has been like such a great episode. I’ve really enjoyed doing this. And if it's OK with you, I've got, like, five rapid fire questions that I'm gonna hit you with. Does that sound good?

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Jimmy Daly (Speaking)

39:27

For sure, yeah. Yeah, let's do it. 

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Nate Matherson (Speaking)

My first question is on video. Should we be thinking about video in the content we're creating? Is that worth doing?

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Jimmy Daly (Speaking)

39:34

That's interesting, yeah. I feel like the answer is yes. And I feel like some of the things I see of, like, SaaS companies doing video is not super high-end video. Like, a couple do. 360Learning comes to mind, is a company that does really cool, like, documentary-style video. Like, Wistia, which is a video company, does some of that stuff. That doesn't have to be your bar. You know, like, I do a lot of screenshare video. And hey, you know what I mean? That's, like, an important part of our own content strategy, and I think that's fine. Particularly if it's platform-native type stuff. Like, if it's built for LinkedIn or if it's built for Twitter or TikTok or whatever channel you're going to distribute it on, videos, yeah, it can be a great tool. But I feel like, you know, don't stress yourself out about making it too professional. 

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Nate Matherson (Speaking)

My next question is on May. You mentioned May was like a really hard month. Like, you're a founder. Being a founder is like a really hard job. It sounds like you've kind of turned the corner and now things are going much better in July. I guess my question is, like, how do you stay positive during, like, those very difficult months? Is there anything, like, you can do as a founder to kind of keep moving forward? Do you have any tips for our listeners? Because I know we have a lot of startup founders who listen to this podcast.

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Jimmy Daly (Speaking)

40:37

Yeah, I think that, wow, I don't know. May was horrible. It was horrible. It really was just so stressful. I just felt like the world was ending basically. I was also on vacation for 10 days and ended up working, like, the entire time because I was, like, realizing, like, “Oh my gosh, like, this business is, like, we're not in a good spot.” Like, I have, I can't just, like, relax on a beach. I need to work. So, like, while I'm on vacation, I'm, like, laying someone off. I'm cutting every expense I can cut. I'm, like, hustling to close a couple deals, you know? And I think that in a stressful time like that, I don't know if there's anything else you can do except lean into it and just do it, you know? In general, I have, like, a small group of peers that I talk to about this stuff regularly, which just I feel like is absolutely necessary. Like, if you don’t — you start to feel like you're going crazy unless you're talking to other people who are also, you know, being like, “Oh yeah, this is really hard. It's, like, that for all of us.” You know, you're not in a unique situation necessarily. That's really important. And then I run a ton. I feel like running is like my, it’s where I get my, like, peace of mind; it's how I blow off steam. So I've been running a ton, just to, like, try to keep my mind clear. You know, it's something I can do away from the computer, away from email, away from Slack, where I can just kind of reset myself. 

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Nate Matherson (Speaking)

Yeah, I love that. The idea of just having that community of other people who are in, like, a similar situation, maybe a very different business, but just having that group of even two people who you can just talk to that are other founders or other entrepreneurs, I think, just helps give you perspective. In my career, a lot of the times when I thought everything was falling apart or, like, going really poorly, looking back, like, a year or two later, it often, like, didn't seem maybe as bad as it felt at that time. And so nowadays, like, I've been a startup founder for 10 years. And so whenever we're going through a rough patch, I just try to think, like, “OK, in a year from now, if we just keep working hard, maybe it's not going to be as bad as it seems right now.” My next question is on content agencies. Are there too many content agencies or too few content agencies in 2023?

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Jimmy Daly (Speaking)

42:34

The world of content agencies has been, has faced a reckoning recently. Like, a lot of agencies were hit really, really hard by this quote-unquote content recession. So, you know, we might be back to where it should be. I don't really know. Like, I think that there's a ton of demand for content, and that demand has been growing very steadily for 10-plus years. So a lot of businesses have cropped up to serve that demand. You know, every now and then you get a stretch of a few months like we've had recently. And I don't know this for a fact, but I imagine not every agency will make it through or some will shrink quite a bit. So, yeah, I don't know. No, I don't think there's too many though. I mean, I feel like, hey, if there's demand to be served, like, someone's got to do it, you know? 

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Nate Matherson (Speaking)

What do the next 12 to 24 months look like for you and Superpath? 

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Jimmy Daly (Speaking)

There's two very important things I'm thinking about. One is the paid Slack group, like I mentioned. You know, we're not starting from scratch, but we're starting from not too far from it. And, you know, building that back up is really important for us. The other thing is kind of what I alluded to earlier, which is like building technology to create an actual marketplace so that content creators will have an incentive to sign up for this platform, and that businesses will have an incentive to sign up for this platform, and that we can bring supply and demand together. That, I think, is mostly a technology issue, and that's the piece — we haven't really built actual technology so that'll be new for us and I expect for it to take a while. Hopefully not 24 months but it may. I believe pretty strongly that that's the thing that ties all the other things we do together, and it's the most valuable thing we can be doing so that's where a lot of my time's gonna be. 

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Nate Matherson (Speaking)

Jimmy, I've really enjoyed doing this episode today. How do our listeners get in touch with you or how do they work with Superpath? 

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Jimmy Daly (Speaking)

Yeah, for sure. Superpath.co is the best place to go. You'll be able to find everything there, Slack group, job board, courses, blog posts, templates, all the stuff is there. So Superpath.co, you'll find whatever you need there. 

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Nate Matherson (Speaking)

Awesome, and you'll get a backlink from us in the show notes. Thank you so much for coming on. 

Jimmy Daly (Speaking)

44:25

Cool. Thank you so much. That was fun.

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44:26

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