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#79: Dru Riley [Being Concise] – 45,000+ email subscribers in less than 2 years

November 09, 2021

#79: Dru Riley [Being Concise] – 45,000+ email subscribers in less than 2 years
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Dru Riley is the creator of Trends.vc, which has more than 45,000 subscribers and 1,000 Pro members.

Dru Riley is the creator of Trends.vc, which has more than 45,000 subscribers and 1,000 Pro members.

With each Trends report, Dru focuses on one core idea or movement. He dives into the history of that idea, why it matters, who the major players in that industry are, the relevant tools and platforms, predictions, opportunities, risks, key lessons, and even some of the opposing viewpoints as to why that idea is bogus.

Trends also has a Pro subscription that goes deeper into each of those areas and includes other forms of media, a community, and more.

In this episode, we talk about Dru’s mini-retirement, why he decided to build Trends, how he thinks about pricing and monetization, what makes a good online community, and why Being Concise has helped along the way.

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Dru Riley  00:00

Some people put more energy into distribution than they put into the content. I don't think that's a bad strategy. It just doesn't work for us. That's not like in our DNA. The DNA for us is to put time into the content, make it remarkable worth remarking about, and then word of mouth will take care of the rest.


Jay Clouse  00:21

Welcome to Creative Elements, a show where we talk to your favorite creators and learn what it takes to make a living from your art and creativity. I'm your host, Jay Clouse. Let's start the show. Hello, my friend, welcome back to another episode of Creative Elements. I appreciate everyone who reached out to me last week after I shared that I was feeling a little bit under the weather, I am back up to speed and feeling great again. But I appreciate you looking out for me. And I appreciate all the incredible feedback that I got on last week's episode with Marie as well. So many of you shared the episode on Twitter and Instagram, which is not only an amazing feeling for me and the guest, Marie, but it also really helps the show to keep growing. So thank you. And please do continue to share the show if you enjoy it. We're in this together and the more the show grows, the better I can make it. And finally, a thank you to Cory Ames, who shared a review on Apple podcast this week that says quote, Jay is producing an excellent podcast with creative elements. If you're looking for a podcast with production value to aspire to, listen to this show, Jay is clearly someone to learn from. Great guests clearly well prepared, planned and researched in the post production seems to do a great job of bringing the conversation to life. End quote, thank you, Cory, for that review. And if you haven't left a review on Apple podcasts yet, please consider taking a moment to do so it helps the show grow helps make the show better. Okay, I am really fired up about today's guest, because he's an excellent example of exactly the type of story that I want to find and highlight on this show. I launched Creative Elements in March of 2020. And right about the same time I started seeing a lot of the name Dru Riley. I hadn't come across his work before. But suddenly, he was all over the creator circles on Indie Hackers, Product Hunt andTwitter. And he was talking a lot about this early career mini retirement that he had taken.


Dru Riley  02:28

I was working as a big data engineer, great team, great pay, I just felt like I could use like a break to try to build something before I turned 30 I just wanted to give it a shot to try to make it work on my own. probably goes back to never enjoying school, not necessarily being a bad student, but always wanting freedom from like a schedule. Being in a classroom, like I'm willing to work hard, but prefer to work, sort of on my own terms. And that was probably it like from probably my first job even like non professionally always like saving for some time off for break, to try to make something work. I have some friends who they have a smooth transition where their side project or business is actually earning more than their full time job. And that wasn't the case for me. I had probably a three to five year buffer financially, where I could have lasted a run that long without working for someone. So yeah, I just linked on that and figured that I'll figure something out.


Jay Clouse  03:33

We'll talk more about Dru's mini retirement at the start of this interview. But he had saved a good amount of money from his job and decided to take the leap into entrepreneurship. You heard him say that he had saved a three to five year buffer that led him to creating a newsletter called Trends. You can subscribe to trends@trends.vc. And sometimes you'll even hear me call it Trends VC. I think I actually first came across Trends from a tweet from former podcast guest Myles Beckler, who was raving about the value of the newsletter. So what's the best way to describe Trends?


Dru Riley  04:05

I'm still working this out, because I know the explanation that makes sense to me and is most accurate, but I would say we we explore new markets and movements and I say movements because no code is in a market defy is in a market. These are more so movements that are happening. Yeah, we explore them we break them down and what are the strategies? What are the tactics? What are the ideas that are at like the core of these things? And this is the part that may not make sense to people that have never heard of Trends.vc. But what we're really trying to keen on is like we're studying change to figure out what doesn't change so what can you attach to and compound in? And that's also why like, as things are changing, like I may seem jaded, like I'm not hopping on this trend hopping on this trend, because I'm more interested in what's not changing what's the through line between these topics.


Jay Clouse  04:58

Within each issue of Trends or each Trends Report, as Dru calls them, he focuses on one core idea or movement. Recently, he focused on the creator economy. He dives into the history of that idea why it matters, who the major players in that industry are, the relevant tools and platforms, predictions, opportunities, risks, key lessons, and even some of the opposing viewpoints as to why that idea might be bogus. You get all of that for free, and more than 45,000 people subscribed to receive that report. But Trends also has a pro subscription that goes deeper into each of those areas, and includes other forms of media, like an audio episode, and a membership community as well.


Dru Riley  05:40

I can describe the typical Trends pro member as someone who values freedom over glory navall would probably say they play wealth games instead of status games. And that also goes back to the bootstrapper Indie Hacker persona of a lot of members that we we have.


Jay Clouse  06:00

And with all of this, Dru has found a lot of success. He launched Trends in February 2020, began earning revenue in May of 2020. And by October of 2020, was earning nearly $40,000 per month from Trends pro members. That is incredible momentum in such a short amount of time and the really inspiring thing is it happened just last year. So in this episode, we talked about Dru's mini retirement, why he decided to build Trends, how he thinks about pricing and monetization. And what makes a good online community. Dru also says a lot of the value in his work comes from how he's able to be concise in his explanations and analysis. And you'll notice right away just how concise Dru can be. I'd love to hear your thoughts on this episode, as you listen, tag me or send me a message on Twitter or Instagram @JayClouse, I would love to reshare it on my own story. And now, let's talk with Dru.


Dru Riley  07:00

I don't believe in like tight budgets or line item budgets. My budgeting approach has always been to throw like a material amount of money into a savings account that's hard to touch. There's enough friction for you to like, get there and play with whatever you have left. And that's been good enough for me, I sort of realized that by mistake by like investing early and having hard financial times as a 18 year old 19 year old and forgetting that the money was there via through those periods.


Jay Clouse  07:33

Where were you living at the time?


Dru Riley  07:35

At the time of mini retirement?


Jay Clouse  07:37



Dru Riley  07:37

Atlanta, Georgia.


Jay Clouse  07:38

So not the not the most expensive city necessarily, but also not the cheapest city to make a living? Did you? Did you consider location in in this experience?


Dru Riley  07:47

I did. It's interesting. You asked that because even as my financial runway was running low, I ended up selling my second house around 2020. And I had the choice of still making a decision within Atlanta of do I stay outside the city city center with things are relatively inexpensive, or do I go and get the place that I really want. And I made the decision to go with the ladder and lifestyle wise, it was a great choice. And it probably created more pressure to make something work.


Jay Clouse  08:19

Well, you say pressure there as if pressure was a good thing. So talk to me about your relationship to pressure and the role that played in getting Trends started.


Dru Riley  08:29

I forgot who I had this conversation with. But we talk about not really two types of entrepreneurs. But two approaches were to go back to the example where some people, they will replace their full time income with a business on the side. And then they'll smoothly transition to their business. And then there are people like me where the pressure, if you will, actually benefits me in terms of trying to figure something out, I think it was Courtland where he talked about this example of saving up enough money from being a contractor. And then was it Parkinson's Law, there's a rule around this of like the task expands to fit the amount of time that you have. So yeah.


Jay Clouse  09:07

Did you know about yourself from the beginning, when you were planning this? You're like, Alright, I've got enough money to last me three to five years. I'm going to jump I don't have a plan exactly as of yet and all the business as of yet. But I know the pressure is what will push me to create this. Does that the mindset you had at the time? Or did that develop as time was passing?


Dru Riley  09:25

Yeah, there were elements of that early on. Like I knew that in the back of my head like I felt it. But the primary thing that I was looking forward to was having the time to just read and explore. And yeah, some people have gap years. I've never had a gap year and it's like, I felt like I was buying myself. This time to explore.


Jay Clouse  09:44

Yeah, I get that. I mean, I've had some time off and time off is always nice, because you do have that like time and space to explore. But it can also be really stressful. Like I remember when I quit my job and I had a small plan at the time of freelancing, but there would be weeks where I would just randomly it seemed spin totally out of control, like, what am I doing? Am I doing the right things? Am I spending the right time on the right things. So as you are entering this time, and you kind of you kind of took the jump without a parachute approach. What's not really clear to me is when you start this mini retirement was the whole thing. Like, I'm gonna take three years and do nothing, and then I'll start doing something or was it I'm quitting my job, and I want to build something, and I'll build it soon. Like, how much fidelity did you have on timelines for when you were going to start creating an income for yourself?


Dru Riley  10:35

Replacing an income, building an income wasn't a high priority, it probably wasn't one, two or three, I had a lot of books I wanted to read had a lot of things I wanted to try. And like those were the top priorities more so than making money.


Jay Clouse  10:50

And did you have like a period of time where you were gonna let those things just stay the priority?


Dru Riley  10:55

Yeah, that's probably coming into like, just letting pressure do what it does, like as the runway started to run low, like, I think, at least in my case, you naturally react to these impending threat will have either figure something out, or you go back to work for someone.


Jay Clouse  11:14

 Yeah, well as as a finance student, you know, I'm sure. Given that you you had that background and you cared about finances, you cared about money you cared about saving, to just watch that account now go completely in the opposite direction, you know, week over week, month over month, when did you start to feel that pressure?


Dru Riley  11:32

Hmm, probably, I think 2019. So within like things, money ran out faster than I anticipated. So probably beginning to middle of 2019. And then for context, trans VC, started in February of 2020. Yeah, so I've journaled probably since 2012 2013. And I have a journaling style, where I keep like a table of contents. And one of those sort of categories, if you will, is around what do I need or want. And I had a list of things. And from that list, I chose based on the likelihood for this to like be a viable business, which, in retrospect, at least when it comes to me was the wrong filter for these things. The better filter was, what could I stick with, and after several failed projects that I chose the most unlikely thing to make money from my perspective, but the thing that felt like I felt like I could do the longest.


Jay Clouse  12:33

That's a really interesting box you just open they're talking about what is the thing I can stick with the longest is the thing that you can stick with the longest the filter, because you think really anything you stick with can be successful? Or do you think that's more just your personality? You needed to stick with something? In order for it to work?


Dru Riley  12:55

Yeah, I think it's both not saying that the first iteration that you come out with will work. But if there's like a seed or core of like inspiration or interest, I think that will see you through to like iterate, there's something there that you can iterate your way to success.


Jay Clouse  13:13

What are the first versions or pass? Or, you know, what are the beginnings of Trends.vc look like?


Dru Riley  13:20

It hasn't changed that much. If you go and look at the first report, you'll notice that like 80% of report 70, which is about to come out 80% of that looks like the first report of this framework based research. There have been slight changes, like there wasn't always a solution section, there wasn't always a key lesson section. But the core style of it was there. There wasn't always a community. But yeah, framework based research, we talk about topics such as micro private equity, no code, audience first products. And even though the topic changes, what's predictable is the format we're going to look at what's the core problem that's being solved? Why this this topic even matter? What's the solution in this space? Who are the players, a lot of people love the hater section, which is just intelligent disagreement, where we're stress testing ideas, and we're trying to steal Manny's ideas, as well as additional resources or links because a big characteristic of or quality of trans VC reports are that they are incredibly concise. So if you want more information there are there's a link section for that.


Jay Clouse  14:26

Which makes sense because you are also incredibly concise. And I've seen from experience like the way that people write is often reflected in the way that they learn to speak as well. When you made your first issue of trends, and it was in a similar framework to this were you making that because you wanted to share it with people and you wanted to get subscribers or is this something that you made because you just wanted to make it.


Dru Riley  14:51

More more of the ladder where it's there are a lot of connections like a lot of areas are connected they don't seem related. But they're very related to me. So I was interested in exposing those through lines. And that's why if someone says, Oh, I didn't check out that report, or I skip that report, because I work in this area, and this is about micro says, it sort of gives to me because they don't realize the through lines between these two areas. So you'll notice that like, especially in a key lesson section, we draw through lines between seemingly unrelated markets, movements, ideas, everything.


Jay Clouse  15:29

You mentioned that this didn't necessarily seem like the most obvious business from the beginning. Why does this not necessarily seem like a viable business?


Dru Riley  15:39

It's probably because of the alternatives that I was looking at, for example, on that, what do I need or want, there were data as a service companies, there were SAS companies, you throw up an idea, and it was very clear, like, okay, how can this be monetized? When this idea came up? That route or path of monetization wasn't clear at all.


Jay Clouse  16:01

After a quick break, Dru and I will talk about the beginning of Trends and the key role that a mastermind group played in its launch and continued success. And a little bit later, we'll talk about how he thinks about pricing, and how we turn this email newsletter into a profitable business. So stick around, and we'll be right back. Welcome back to my conversation with Dru Riley. Before the break, Dru was telling us about his decision making framework for picking an idea to run with, he mentioned that an email newsletter probably wasn't the most obvious choice for him as someone with a background in finance and development. So I asked Dru, when he first began thinking about the idea of the Trends newsletter, how the idea was received amongst his friends.


Dru Riley  16:40

I don't think they understood it. So when I think about this question, my mind goes back to a mastermind group that I'm a part of, or was a part of called Zero to One makers. And I remember throwing the idea up at the end of one of our sessions. And there was sort of like general indifference, if you will, Edmund came over, my friend Edmund came over the top with excitement about the idea. And that was enough to get the first report out. And then once people saw the report, they finally understood what it was hard to describe around what I was going for, and then they finally got it.


Jay Clouse  17:18

Do you remember how you initially described it to that group?


Dru Riley  17:21

Probably framework based research, which may not sound super, super exciting.


Jay Clouse  17:26

Yeah. Well, tell me why you choose those words.


Dru Riley  17:29

It may go back to like the exploring the through lines, or like the fractal nature of everything that we talk about, because even though the topic is changing, there are reasons why this thing matters. There are core problems that are being solved. Which is why, for example, if we talk about growth tools, which some people also call engineering, as marketing, when we really get to the root of like, what is the problem that growth tools solve solves is that you're trying to sort of outpace these pay channels like Google or Facebook, like it's like a Red Queen's race. And that's why we ended up talking about the Red Queen, even though we're talking about this space of growth tools, that when you really get to the core of these things, it may be a completely different topic, but at a text, same core problem.


Jay Clouse  18:15

I've never heard the term Red Queen. What is that?


Dru Riley  18:18

 I think it comes from Alice in Wonderland, where there's also some like ties to like evolution, where you're sort of like running faster to stay in the same place. But if you don't run faster, then you don't survive.


Jay Clouse  18:33

I want to learn a bit more about this mastermind group, because as far as we know, at this point, you are two to three years inside of you know, quitting your job. So how did you or when did you and why did you seek out a mastermind group?


Dru Riley  18:47

So I didn't really know what I was joining. At first, it came I found out about the mastermind group through a local Indie Hackers meetup, where KP a lot of people know KP from on deck, KP was hosting this local Indie Hackers group in Atlanta. And then I came to a few of those which was held on a monthly basis. And then I sort of heard like, not necessarily rumors, but whispers about this other group that met on a more frequent basis. So one night, I asked him about it, and then got an invite to that group. And then that was the mastermind group zero to one.


Jay Clouse  19:23

How many people were in that group?


Dru Riley  19:24

At the point that I joined? There may have been six or seven of us.


Jay Clouse  19:29

And was there like a clear commonality or some sort of like filter on who could be in that group?


Dru Riley  19:37

There was a filter, it's a funny story and a KP is gonna hit me because I'm bringing this up. But when I first asked about the group, he was like, someone has to invite you in with a lot of people know it from that unicorn wit was right next to him. He's like, Well, I invited him I'm not sure what the filter was. But there was there was a filter there and maybe I just didn't pass it. For KP at first.


Jay Clouse  20:01

What I'm hearing here is, there could have been a very real future where you didn't make that uncomfortable ask, again, that might have changed everything, you know, and that that's something I wanted to point out because people are often the difference between success and failure. And there's often like an ask involved, when there's somebody that can make some sort of difference for you.


Dru Riley  20:25

Yeah, that was consciously what I call a comfort challenge, were going to the Indie Hackers event that night was a comfort challenge, I may have presented at that same event that was a comfort challenge, and then asking to join this group was another comfort challenge. And I see this idea of comfort challenge as doing things that are new and or uncomfortable. And these are sort of like asymmetric bets. That seems scary, but could have a ton of upside, like you just said, and I think this was one of those that had a lot of upside.


Jay Clouse  20:55

How often do you try to push yourself to make a comfort challenge?


Dru Riley  20:59

Each day, at least, and I say each day, because it's on average, I have this weird habit around habits were like a habit bank, meaning that if I do 10 comfort challenge this day, another category I have in my journal is where I can keep track. And then I use a habit app called habit list. And for example, if I don't do one, tomorrow, I can draw from that bank.


Jay Clouse  21:21

Oh, I see. So yeah, it's an average thing. So if you you tell yourself, you want to have seven of these challenges per week, you don't have one today, you can do two tomorrow. Or if you did two today, you can not do one tomorrow, I'd be on track.


Dru Riley  21:32

Or if I have a bank of 22. As I do now, I can draw on it and not do any comfort challenge for the next 22 days and still keep my streak in the app.


Jay Clouse  21:41

Do you have any clear patterns in the types of comfort challenges you're taking on? Or do they look different? Oftentimes?


Dru Riley  21:47

Yeah, I forgot who I heard describing this. And comfort challenge go by many names, but I like the way they broke it into categories where there are like mental challenges, physical challenges and social challenges. The mental challenges I find easiest social challenges are somewhere in the middle for me, Well, no. mental challenges are the easy physical challenges are somewhere in the middle. And the social challenges are hardest as an introvert. But I think that's where a lot of opportunity to improve is around those social comfort challenge as a category.


Jay Clouse  22:20

So we heard about the comfort challenge with asking to be a part of this group, I would imagine that presenting at that meetup might have also been a social challenge. What other like, I'd love to hear some impactful comfort challenges that you repeat in any of those categories, or all those categories.


Dru Riley  22:37

Yeah, one in it's interesting, because there's so we can go so deep into this area of comfort challenge. I'm working on an essay around it right now. But uh, the one that came immediately to mind was around cold showers, which we could book it as a physical challenge. And it comes to mind because what's interesting, there's about a month ago, that stopped being a physical comfort challenge. It doesn't feel amazing jumping into a cold shower each morning. But I can no longer count it as a comfort challenge, because a big part of this is you have to be intellectually honest around, does does this still scare me? You can repeat them if it genuinely scares you. But I don't know. I've been doing cold showers for maybe three or four months now. And I can't honestly say that there's as much discomfort associated with it as it was at first.


Jay Clouse  23:26

What about a mental comfort challenge?


Dru Riley  23:29

I'm probably having a hard time coming up with those in the same way that an extrovert would look at the social comfort challenges I mentioned. And like, just laugh those away where the middle ones are. Maybe I started playing chess again recently, like maybe we can count that playing like a few games, my first few games back in as a mental comfort challenge.


Jay Clouse  23:52

I relate to all this. I was I was talking with a friend of mine, Jake Hanzo, who's been on the show, and he's doing a whole episode about probably mental is where most of these come into play. And the one that is really challenging for me lately, which actually, by your framework might be a social challenge. I know this show will continue to grow and continue to do better and better and better. If I reach out to like crazy guests that I have no, I have no business interviewing. And most of those people are gonna say no, or a lot of them will just ignore me. But that is so challenging for me. Sometimes I have to like psych myself up and do a batch of okay, here go 10 cold emails right now. Maybe I'll hear from one of them. But I gotta send 10 So I can fill the pipeline of guests and make sure that the people who are coming through are really great. So I'm drilling in on this because I feel it almost viscerally as to how important these things are.


Dru Riley  24:43

Yeah, I love to add to that were doing report reviews. I started these after report 30 where I talk to domain experts about whatever topic we'll cover. And a lot of the outreach for those report reviews have been social concrete challenges and I've met A lot of amazing people by doing that uncomfortable ask that you just talked about, like Linda from Scalar Capital comes to mind where we've collaborated on every crypto related report that's ever come out. And she's super open, super generous with their time. But maybe like you like we, I tell myself these stories of like, you know, she's up here and wouldn't want to collaborate. And she's been more than open in terms of collaborating. Sort of another inflection point that comes to mind is last year with a founder Summit, which was held by Ernest capital now, calm company fund, he went, Tyler Tungus went on the Indie Hackers podcast and mentioned to anyone that wanted to join, but maybe like, wasn't in the financial position to afford the conference ticket at that time. So I reached out to him via email, that was another social conference challenge that that was just a world changer. And I went out there after joining Zero to One makers, but sort of coming back and realizing that these people that you look up to, at the end of the day, they're just normal people after, you know, you shrink tequila with them at 2am. In the morning, eating tacos, like you just realized they're normal people.


Jay Clouse  26:11

And I'm sure the same as happening for people who talk to you, right? Because over the last year, you've grown trends to more than 45,000 subscribers. But that's in a span of a year. So there are 45,000 people who are looking at you as an authority on something. And they may be having the same thought about you. How has that impacted? How you think about yourself or your work? Like, has that elevated your own view of yourself? Is that a challenge?


Dru Riley  26:39

Yeah, I've never attributed because it has become easier to like, reach out to these people and interact with them. But I've never thought about it that way. I'm more so think about talking to people or meeting people like Tyler and Rob walling. And these are people that I look up to. So once you sort of build a critical mass, or once I built like a critical mass of these people that I can call friends, mentors, everyone else sort of falls in place from there, not in a bad way. But in terms of it's easier to have these conversations because I've like a lot of people that I put on this pedestal have become friends.


Jay Clouse  27:16

Totally. Similar experience running a podcast and being able to talk to a lot of these people and realizing people are people they want to be treated as people. It's weird when you almost other them by giving them so much respect. It's uncomfortable in a way. So I resonate with that as well. We're starting to get a little ahead of ourselves here. And so I want to go back to Dru's journey, Dru launch Trends in February of 2020. I found a tweet from him on May 10, 2020. That says, my first shot ad monetization failed. Last week 102 views, zero sales. He went on to say that while writing that tweet, he had his second sale ever on Gumroad. So I asked him several months into writing Trends, but not necessarily seeing a return yet. Did he think the newsletter was successful or on the path to being successful?


Dru Riley  28:04

Yes and no. So it felt successful, because there was a feedback loop forming of there were people reading open rates were incredibly high. The no comes in terms of the monetization strategy where I was still running like the runway was still running low. So knowing that sense, and looking back, I compare something we're working on now at trends to something that I was struggling with back then. And that's around how are we going to scale masterminds now. And it's a similar situation to what I dealt with them, because I had a lot of ideas around the way that trans VC could be monetized at this point that there was an audience built around it. And in a similar way, I have a lot of ideas around how masterminds could be scaled. And we literally just have to like, iterate through these different versions. And we'll probably keep pieces of each one. Until we have this model or this machine that's working. And it was a similar thing there were sponsorships could have worked, direct support, could have worked consulting could have worked, custom reports could have worked. One of those just had to work and when in my experience, when you have a lot of options, you only need one to work in one is going to work but you have a lot of options.


Jay Clouse  29:21

Did you test all those options? Or did you start with one and suddenly that was working?


Dru Riley  29:26

I guess we tested two. The first one was, well, technically three, the first model was around pre ordering the next report and that was sort of decide which report got made and like a Indiegogo or Kickstarter style that completely failed, and almost wrote off the whole like direct support model. And then the following week, I did the like split the report. So there was a free version of pro version and then that worked. And then the purchases came at such a rate that in the back of my head. I just had this feeling like there was nothing else to worry about like with this be a billion dollar company, maybe not. But in terms of a profitable company, it felt like we crossed, we've we crossed that threshold.


Jay Clouse  30:12

So the split report, were you saying that you could buy that ala carte, and you also had a paid membership as an option.


Dru Riley  30:20

So at first, there was only the free version, the pro version, so you could buy like a free pro version one off, I wasn't even thinking about subscriptions in terms of someone would want to subscribe. And then that same day, several people asked for subscriptions. And Patrick Campbell, from profit, well shout out to Patrick was the first one to subscribe as a trans pro member.


Jay Clouse  30:42

What a beautiful email to receive what it feels like for someone to email you and say, Hey, can I actually just pay you every month instead?


Dru Riley  30:49

It felt amazing. Yeah.


Jay Clouse  30:52

When we come back, Dru, and I talk about his process for producing a Trend Report, the way he monetizes the newsletter today, and how he thinks about the role of community in a membership right after this. Hey, welcome back. At this point, Dru had found a model that allowed him to begin making money through his newsletter, he would have a free version of each Trends report and a paid version that went a little bit deeper. So I asked him to explain a little bit more about his process for creating a report, and how he determines which pieces of it are made free and open, versus put behind a paywall.


Dru Riley  31:26

I recently made the decision to try to work with a few other writers and move to more of an editor role, I will still do some writing, but I will do much more editing. And this is something I would love to show the writers that I work with. But it's like this front loading process. And I got this habit from chess where if you have 10 possible moves, basically running like a linear search algorithm in your head to figure out the best move. But doing that for each opportunity or each prediction and opportunity section. It's a mix of how big of an opportunity is this? And how many people does it help in the prediction section, it's how important or impactful is this prediction, and then the confidence level of it. So some mixture of these sort of attributes of each category, and then front loading based on the top, and always putting the strongest candidates up front, and then usually take about 50% to 60% of that and then make that free. And then the latter half will go to a pro version of a report.


Jay Clouse  32:32

And has it always been that way? Or did you learn your way there.


Dru Riley  32:35

That's another thing that I think was in in the beginning in the first report this sort of habit of front loading. And now that I think about it, a lot of this stuff was worked out in terms of the format of the reports that habit, probably because I set on this idea for so long that there were a lot of things that I thought would work for it, I want it to go into it. And I probably pulled the trigger very late. So a lot of it came fully fleshed out by the time the world saw it.


Jay Clouse  33:02

How did you think about pricing for the pro version of a report? And then as you rolled out subscriptions, how did you think about pricing, then?


Dru Riley  33:10

Pricing? At first may have been like reference pricing? Or I'm not I'm not really sure like what was the pricing strategy at first, and I wouldn't want to make anything up in retrospect. And then pricing. Now it's very interesting, because if trends didn't have a community attached, it would be priced very differently. But the community did a lot of interesting things in terms of the light friction or barrier to entry. In a similar way. i In the past, I wouldn't hesitate if someone asked for a discount to give them a discount if this was just a zero marginal cost product and a form of reports. But now that we have a community, I've actually noticed that there's a very, like direct inverse correlation to people that ask for discounts and like the quality of community member, if you will. There are slight purchase parody built into it. But it's something about people that would ask for discounts in terms of the type of community member that they become. So it's actually complicated things like pricing.


Jay Clouse  34:11

And what is the pricing now just so I make sure I have it right.


Dru Riley  34:14

If you're only interested in reports, that's 240 a year US and you can also like discuss reports with others. If you're interested in the community, meaning that there are daily stand ups you can participate in a weekly trends tribe calls, which are just multiple rounds of one on one chats, as well as the option to join masterminds after a 100 day stand up street. That tier is 300 a year. And if you want direct access to masterminds, that option is 1200 a year. What's interesting about that tier is that when people opt in to that the opportunity cost of their time tends to be so high. So they use it to more to like express support it seems then to actually participate in the masterminds which is very interesting, because we would love to have them. But again, it goes back, it seems to the opportunity cost of their time.


Jay Clouse  35:06

When did you determine that a community component would be part of trans membership?


Dru Riley  35:12

That probably came shortly after report review started. So shortly after report 30, where I was meeting a lot of vend, just readers, and I thought it would be dope if they could meet each other. And I started to make these connections directly between people. And it just felt like it would be great if they could self initiate these, instead of me being in the middle and making these connections.


Jay Clouse  35:36

What do you guys use for your community back end? What platforms do you use?


Dru Riley  35:41

We use circle. And that's what people think about like Slack circle discourse, we use circle for that. And we have a ton of other tools that we use to sort of augment that.


Jay Clouse  35:52

You mentioned the pricing, you gave annual costs, is it annual only?


Dru Riley  35:57



Jay Clouse  35:58

I imagine that was an intentional decision. And I'd love to hear your reasoning behind why annual only versus monthly or even quarterly.


Dru Riley  36:05

So there was a monthly option at first. And one thing I'm not I haven't, like thought deeply about this around business models and sort of the pricing periods. But at least the way that we think about it at trends VC, is if there's a year plan, like there's a year for you to like, experience that value. And even if you look back over the last year, someone asks in the recent product launch, like what has changed since trends 2.0, 1.0 to 2.0. And it's basically like 60% to 70% of it has changed if you opt it in to Trends.vc Trends pro paying $9 a month, there was no community, there was no masterminds, nothing like that. And there are people paying $9 a month or that have become lifetime members that pay nothing and they're part of masterminds. So it's this increase in value. And we have this time to compound, iterate and improve the experience. And for you to realize that value in that year versus like month to month period.


Jay Clouse  37:07

I've spent a lot of time thinking about community and memberships over the past year. And more and more. Those are distinctly different things in my mind, for a lot of memberships, a digital community space is a core part of the value proposition. But I don't think it necessarily has to be some content memberships are all about additional content. And that's it. So I asked Dru whether he thinks cultivating community is a necessary part of a content membership?


Dru Riley  37:32

I don't think so. And I think it complicates things. And I've thought about this a lot where I wish that we didn't have to start the community, but it's almost looking at other like communities that tried to like serve a similar role and is like seeing bugs that needed to be like fixed or tweaked if you will, where I recently wrote in a Twitter thread that the community added much more work to the process and the operations of trans VC, but it felt like it was something that needed to happen in terms of again, hosting standups masterminds with certain certain constraints around them.


Jay Clouse  38:09

Yeah, because it is, it is a huge time commitment, right? It's not it's not a passive thing, it's a very active thing. It almost gets into like services in how you spend your time or hire other people to spend their time. It's it's something that I don't think people think about enough when they strap on a community component to a paid membership.


Dru Riley  38:28

And then there's that part that we talked about in one of your threads around negative network effects, which people seem to overlook, especially when they think about niche community. So you've almost added this, like, I don't want to call it negative compounding because that's not what it is. But this is like device or attribute to your business. And we're working on like turning that on its head right now. And we can go into that if you're interested in how do you flip these negative network effects on its head, but it's something that you would have to navigate especially if Yeah, especially if you don't have like sort of this this like personalization that would go into a Facebook or Twitter or social network, which is a nother beast, because those aren't all even communities in my mind. Those are like communities of community, some of which hate each other, if you will.


Jay Clouse  39:17

What do you mean by negative network effects for people who aren't familiar?


Dru Riley  39:20

So usually people use the term network effects they usually mean it as like a positive attribute or quality of a business meaning that the more people that let's just say apply to like different types of businesses, but let's just take Twitter as a as an example. The more people that join Twitter, the higher quality threads for example, if you use Twitter for threat, we'll get surfaced because you have more people sort of competing for this attention and the best will make it to the top the best will be surfaced. You will also see what you're most interested in what you see on Twitter, Jay is different from what I see on Twitter, in these niche communities where they haven't necessarily solved this before. personalization problem, everyone's seeing the same thing, which means that instead of, you know, Twitter, maybe 10% of threats have to be good. In a niche community experience, I would say 80% or 90% have to be good if we're all seeing the same thing.


Jay Clouse  40:16

And if you are paying for something because you want access to the community, you're paying for value that's created by other people that is out of you Dru Riley's control a lot of times, and if the quality of things begin to degrade, or somebody's friend leaves the community, now they want to leave it can trigger this downward spiral of other people following suit and leaving.


Dru Riley  40:38



Jay Clouse  40:40

Well, with the time that we have left, I want to kind of close out the Trends growth story a little bit, because, you know, we mentioned first sale happened in May of 2020. Today, you have 45,000 subscribers or more. A 1000 Pro members, I've heard you say, maybe more than that now. That's huge growth in the span of a year. So looking back, what were some of the inflection points that allowed you to get in front of so many people for them to have the choice to subscribe.


Dru Riley  41:10

My mind goes directly to our first Product Hunt launch, which happened August 2020. And around that time, we had maybe 6,000 to 7,000 free subscribers, which mostly came from Twitter and Indie Hackers sharing threads of reports there. And then that product launch within the course of that month took us from like six or 7,000 to 25,000. And then from August of last year to August of this year, we went from maybe that 25k to 40k. And then so far, since launching last week, we went from like 40k to maybe at 46,000 or 47,000 from the second Product Hunt launch. So those are just a couple inflection points.


Jay Clouse  41:57

Those are incredible numbers from Product Hunt, even specifically, what do you think attributed to such high conversion from page view to subscriber and those campaigns?


Dru Riley  42:10

Hmm. It may have been the social proof from like not launching too early. So there were people who experienced the value and could like attest to the value on a product launch page. So that goes into not only the conversion of people being on the page, but even making the page visible and people being aware that support came from those who experienced the value before.


Jay Clouse  42:34

Yeah, I think about your your homepage a lot. Because it's basically social proof and an email capture says join 45,000 plus entrepreneurs or something to that effect. And then it's just an email capture. And there's no real other thing that you can do when you hit that page, which I imagine converts really high. And I'm wondering if you've tested other versions of that, and how intentional that choice is to this day.


Dru Riley  43:02

Yeah, there was an intense period of testing, maybe it was six or seven months ago, until we got to a space where it felt like, Okay, this is a good enough conversion rate. And you're right, it converts very high, probably between like 40% to 60% of people who hit that page. And I didn't realize that was possible until reading I forgot who posted it, but someone posted on Indie Hackers about their conversion rates. And since then, we haven't done a ton of testing.


Jay Clouse  43:31

Crazy. And seems like once they're in, they kind of stay in. Talk to me then about how you approach social media or Indie Hackers or anywhere else, that you're sharing your work on a weekly basis that isn't directly to your existing subscribers.


Dru Riley  43:47

So Twitter has been like a great like engine for us in terms of growth. So there's going to be a Twitter thread, that's table stakes. We also still share reports on Indie Hackers, that's going to happen. But it's really optimizing just for like quality. And some people say don't do this, I think it comes down to like what type of strategy you want to run, we're put some people put more energy into distribution than they put into the content. I don't think that's a bad strategy. It just doesn't work for us. That's not like in our DNA. The DNA for us is to put time into the content, make it remarkable worth remarking about and then word of mouth will take care of the rest. And there's like a minimal viable dose of distribution. And that's exactly what we do.


Jay Clouse  44:33

On your first Product Hunt campaign. You mentioned that that I think that went to number one product of the day, right?


Dru Riley  44:39

Yep. The first time around. It was product of the day, week and month. Yep.


Jay Clouse  44:43

Day, week and month crazy. How much did you lean on your existing subscribers to push that campaign versus it was kind of like organic products on traffic?


Dru Riley  44:53

I tribute a lot of that success back to the zero to one group not only in terms of like sparking Trends.vc itself. But it reminds me of the fact that we're still sort of this clan, if you will, where like if one person launches something they have at their disposal all of the audience of everyone that's like in this crew. So if you're in this bootstrapper, Indie Hacker community, that's probably all you heard that day from that group of people. So, again, it goes back to like, sure, like the subscribers experienced the value of Trends.vc before that launch. But a lot of credit also goes to that zero to maker, Zero to One maker crew.


Jay Clouse  45:36

Well, for somebody who's considering creating a paid content membership, meaning that they want to offer extra or different or exclusive content for subscription fee, what do you really think they should consider or understand about that business model?


Dru Riley  45:54

This will be biased, because I mean, I see the world through my lens, it would be just a focus on quality, and not just to focus on quality to go back to distribution, there's a minimal viable dose of distribution that's needed. But it feels like there are a lot of people like yelling about things that may not have the substance to like back up the volume of their voice, where it feels like if you create something that's worth talking about, and then make people aware of it, the word of mouth can carry the rest of the message. I don't think enough people are focusing on quality.


Jay Clouse  46:32

Do you think that map's to reader expectation as well? Do you think people who are paying for premium content have really high expectations?


Dru Riley  46:40

Yeah, I think it's a prerequisite, especially if you're doing this direct support model of like people paying you for content. One of my favorite podcasts is the Founders podcast is also the only podcast that I pay for, and the like quality is extremely high. If we move to more of a like sponsorship model, you're almost rewarded for noisiness where you're trying to satisfy all of these different types of stakeholders, including the sponsor, but I also think the like quality bar is lower there, because no one's directly supporting you like the the, yeah, the incentive structure is just like way more diluted, where the readers aren't necessarily the people that are supporting the content. So you get all over the place, there's a place for that there's a place for everything. But when we talk about this paid membership model, quality matters a lot.


Jay Clouse  47:39

I find Dru's stories so inspiring. And not just in the hall. Oh, wow, that's so cool type of way. But truly the, if this guy can make this work in such a short amount of time, I could do that to sort of like, what really stands out to me is just how quickly Dru did build a revenue component to his business, from launch in February to earning some sales just a few months later, is actually really quick for an email newsletter. And what really helped Dru along the way, were some of his social comfort challenges. He was able to gain the support and advocacy of other people in the early days that really helped his product launches and more. That's such a big opportunity for all of us. But I know it's uncomfortable to ask for help. The big goal for me is to do a better job of that next year. And I bet you could do a better job of that too. If you want to learn more about Trends, you can subscribe for free@trends.vc and you can follow Dru on Twitter @DruRly. Concise even in his Twitter handle. Links to both are in the show notes. Do you want to be featured on a future episode of Creative Elements? I love hearing listener questions and I'll be embedding them into episodes of the show along with my answers. Just visit creative elements.fm to leave me a voicemail asked me a question and I'll put that into a future episode. The link is in the show notes. Thanks to Dru for being on the show. Thank you to Emily Clouse for making the artwork for this episode. incredible artwork this week. Thanks to Nathan Todhunter for mixing the show and Brian Skeel for creating our music. If you liked this episode, you can tweet @JayClouse and let me know or find me on Instagram @JayClouse. And if you really want to say thank you, please leave a review on Apple podcasts. Thanks for listening, and I'll talk to you next week.