How To Grow And Scale Your Newsletter with Dru Riley

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How can you build and monetize a newsletter that attracts the right audience?

Dru Riley, the founder and CEO of, joins the podcast this week to break down proven methods for growth online.

Dru Riley has built his newsletters to over 60,000 subscribers - with an audience of founders, investors, and thought leaders in companies like Apple.

In this episode of Creators on Air, he joins us to discuss how to grow your newsletter, convert readers to paid members, and work with sponsors.

Follow Dru:

🐦 Twitter

📰 Newsletter

💻 Trends Pro

🤝 Passionfroot Storefront

Episode Transcript

Akta [00:00:00]: How can you build and monetize a newsletter that attracts the right kind of audience?

Dru [00:00:04]: Being consistent in terms of the topics that we cover, the voice that we have, or the angle that we come from, and then the other side is probably around small decisions that we make. So each email that goes out is being split tested.

And when we're looking at different variants in terms of which version of the split test wins, we almost never optimize for unsubscribe. So we're sort of not afraid to put something out there that's spiky content in terms of making people make a choice in terms of “this isn't for me, I'm going to unsubscribe”.

Akta [00:00:34]: Dru Riley is the founder and CEO of His newsletter has over 58,000 readers, including founders, investors, and people from companies like Apple. In this episode of Grace on Air, Dru shares how he grew his newsletter, how he converts readers to his membership, and how he works with sponsors.

Dru [00:00:53]: So explores markets and ideas. It's mainly for founders, also executives, investors, people that are in the area of business. And the big idea is that we use framework based research to explore different areas. So although one week we may look at micro private equity and next week we may look at no code, we're using the same framework of: what problem does this market solve? What's the solution, who are the major players?

We do some evidence based predictions, explore some opportunities in the space and so on. Everything sort of follows this framework that we developed and has evolved over time, but that's applied to different markets and ideas.

Coming on the tail of the mini retirement, I wanted to maintain flexibility that I got used to while on that mini retirement. So if I could help it, I didn't want to go back into software development working for someone else, I would have done it for myself. And I was inspired by the twelve start ups in twelve months movement.

So a lot of things that I did explore were around mobile apps that I built, or SaaS apps or data as a service. And all of those projects and businesses and ideas were based around this idea of what seemed like it was a good business or what could make money. And after I ran out of steam chasing all of those different ideas in a short amount of time, I started to ask a different question, which was, what can I stick with?

What could I see myself doing for the longest? And that answer was clear. It turned out to be It didn't have a name at that point. It was more so this idea of framework based research and yeah, everything didn't work out immediately. But that's why that question was helpful. Because if you can stick with something for long enough, what I found is that you can stick with it through the struggles and through the uncertainty and the doubt and the dips and the lack of feedback.

Yeah, there can be a lot of struggles, but that's why that question is helpful.

Akta [00:02:56]: Definitely. And I'm really intrigued by the framework based research that you're talking about and the actual content of your newsletter, because on your landing page it says that you save 2000 hours of market research with free five minute reports on AI, crypto and more.

That sounds like a lot of content. What is your process for researching and writing each issue?

Dru [00:03:20]: Yeah, so I just shared this on Twitter a few weeks ago, but we use software called Process Street and we break down the process of researching, drafting, revising, staging, distributing the report into over 100 steps.

So it's very, maybe you can say organized at this point, but those are the high level steps that I just laid out. But yeah, each step has a due date. One thing that maybe other newsletter creators can take away, especially if you're working with a small team, is that we have a three round revision system and that may have had the biggest effect on quality, where again, everything has a due date attached to it.

But we go into the drafting not expecting for the report to be perfect and also understanding that there are going to be at least three stages of feedback to bring quality up to par. So maybe that took us five or six months after we laid out this process to introduce that revision system, but it was a night and day difference in terms of quality afterwards.

Akta [00:04:24]: You’ve managed to attract over 58,000 readers, which is insane. What have you found to be the most effective newsletter growth strategies?

Dru [00:04:33]: Yeah, so it's twofold for us, and then we have a newer one. The two that have worked best historically have been product hunt. So I think numbers wise, that's still the biggest source of subscribers for us. And then also Twitter. So taking newsletter content and adapting that to a social platform, in this case, Twitter or now X. Recently, SparkLoop has also been working really well for us.

Akta [00:05:00]: So how do you use, I don't know what it's called, Twitter or X? How do you take your content and make it relevant on Twitter or X so that it doesn't seem like promo?

Dru [00:05:13]: It’s harder than it sounds, or maybe you realize how hard it is and that's why you asked the question.

Akta [00:05:18]: Exactly.

Dru [00:05:18]: Yeah. It requires you to think about first principles as overused, but it requires you to think about the content from first principles. There was a time when I was the only person writing reports, when I would wait to publish a report until after I had the tweets that would be derived from that report drafted. And what would happen about 80% to 90% of the time is the idea that I'm trying to adapt to Twitter.

I need to rewrite that idea because I simplified it so much and clarified it so much for Twitter, I'm realizing it can just be communicated this way for the newsletter audience as well. So there's that much massaging. I don't know if I have the secret to it other than just invest the work and don't underestimate the effort that it takes.

Akta [00:06:05]: And do you find things like threads are most helpful, or is it single? Like, how are you structuring the content from the newsletter into Twitter or X?

Dru [00:06:15]: Yeah, based on my experience, and I've heard other people say something similar, that if you're optimizing for followers, followers almost never come from individual tweets, they come from threads. I also like this framework I've heard Justin Welsh talk about, which is sort of CTA call to action content and non CTA non call to action content.

So threads, there's usually a plug tweet at the end where you're trying to drive traffic back to the newsletter to get subscribers, but a lot of sort of individual tweets, it's not CTA content, so there's no call to action in there. And it's more so of sort of investing in this trust jar or depositing in this trust jar over time.

Akta [00:07:01]: And have you noticed any style of threads or tweets that have really brought in a good amount of subscribers?

Dru [00:07:10]:

The algorithm is always evolving, and it's like if we talk about this, this month or three months is going to be completely different. One thing that we've been thinking a lot about recently, and if someone pays attention to my account over the next two weeks, you'll notice that a lot of the threads include media.

So images, videos, gifs, because that's something that was an effect of like a recent algorithm change where they're really optimizing for non text or like multimedia style tweets. There's the given, I don't like to play this game, but sort of optimizing for controversial content, so engagement at any cost. But you also have to think about your long term company brand, personal brand, if you play that game as well, because it can get dicey.

Akta [00:07:57]: Yeah. And it seems like you've attracted quite a high quality audience. What I mean by that is that you've attracted the people that you kind of want to attract, like founders, the investors, people from companies like Apple.

How do you think you go about attracting the right types of readers, not just going viral, you're actually bringing in the people that you want to bring in.

Dru [00:08:18]: Yeah. I think the table stakes of that is being consistent in terms of the topics that we cover, the voice that we have or the angle that we come from. And then the other side is probably around small decisions that we make. So each email that goes out is being split tested. And when we're looking at different variants in terms of which version of the split test wins, we almost never optimize for unsubscribe.

So we're sort of not afraid to sort of put something out there that's spiky or spiky content in terms of making people make a choice in terms of this isn't for me, I'm going to unsubscribe. So it's a mix of being consistent and also sort of designing systems or the way that we do things in a sort of non fearful way. Right.

We're not afraid of unsubscribes or optimizing for engagement. And for example, if one variant has higher engagement and higher subscribes, we'll take that variant.

Akta [00:09:12]: That's interesting because it's like you're not trying to appeal to everyone, you're just trying to appeal to the people who actually want to read this content. How did you actually find out who your subscriber list is made up of?

Because I find it really interesting that, you know, I've got these people from these companies. How do you go about finding out that information?

Dru [00:09:31]: Yeah, so there are a lot of data enrichment tools out there, and I wasn't aware of this industry when we first used one. It came across, there's a creator friend of mine, Jacob Greenfield, and he started offering data enrichment on email lists as a productized service.

I don't know if that service is available anymore because he started a different company sort of reusing that skill set but for sales as a service. But we used a data enrichment tool which sort of will take an email address or just sort of stems a data and then expand it for you and give you all of this additional information.

Akta [00:10:05]: And how do you use that information once you know that? Does that affect the way that you go about your newsletter in terms of creating it or distributing it?

Dru [00:10:15]: Yeah, so we haven't used it as much as we could. The main way that we use it is to help sponsors make a buying choice. Right. So who are they advertising to? And to be fair, that was also the motivation or the spark to use a service like that in the first place because, okay, we announced sponsorships, and then a common question that we're getting from maybe 50 or 60% of inbound sponsors, who's on the list? Right. What's the average company size? That type of question.

Akta [00:10:47]: Yeah. And then let's talk about monetization. Since you have brought up sponsorships, is sponsorships the only way that you've monetized or what else is going on in the business?

Dru [00:10:57]: Yeah. So it's a major way, but the main source of monetization comes from subscriptions, which is in the form of Trends Pro memberships. So there's the free newsletter, there's the premium newsletter in the community. So that's what I mean by subscriptions.

Sponsorships is probably number two. We also have an e-book which is like a tertiary revenue source. We've experimented with NFTs as lifetime memberships. We've dabbled with affiliates as well. But all of those are like tertiary. The main two sources are subscriptions as TrendsPro memberships and then sponsorships.

Akta [00:11:37]: And how do you decide what sort of content is going in that free newsletter versus the premium?

Dru [00:11:43]: Yeah, it's the cliche. What people talk about is like, give the best stuff away for free. Yeah. So I have this tick that's turned out to be useful. I picked it up from chess, this idea of front loading. So if you're given like a linear list, it takes a bit of time and it takes effort, but okay, what's the best item in this list?

Move that to the top and then you sort of keep asking that question until the whole list is sorted. And the good thing about the fact that this is framework based research, as opposed to sort of like prose or a traditional essay, it's easy to move bullets around. So I front load like the best, by my perception, the best stuff up front, and then that becomes the free content and then the sort of tertiary bullets, that's the pro content.

Akta [00:12:31]: And how do you bring people from the free version to the subscription? What have you found to be effective?

Dru [00:12:39]: So going back to split test, it's been a while ago since I had this insight, but we write copy for each report. Right. So what will you get with the pro report? There's like custom copy that's written for each report. That's sent out so that we can get upgrades and that takes so much effort and time. I was just curious, is this actually making a difference in terms of if someone gets a version without this customized upgrade prompt versus people that do, does it make a difference?

And it makes a big difference. So that's one thing that we do, is we write custom copy for each report that goes out. Maybe something else. And I'm not sure, I know it helps, I'm not sure how much it helps, so I can't really quantify it.

Dru [00:13:26]: But a while ago, maybe about a year and a half ago, we introduced more of a curated content type called Founder finds and it focuses more on the community and highlighting members in the community. So each week, what are some trends? Pro member wins and we aggregate those, they're usually like seven to ten wins, whether someone launched a newsletter or they hit 300,000 views on YouTube, or these types of things that we collect in the community and highlight, there are also editorial pieces in there.

So how do you do pricing different AI email marketing tools you could use? How do you set goals in a scientific way? Things like that. And I think that highlighting the community and sort of the okay, if someone didn't upgrade because they just aren't interested in pro content, but they want community support, we also talk about different things that are unlocked in the community.

So if someone posts their first stand up and they unlocked one on one intros, we count that as a win. If someone hit a 30 day stand up streak and they join masterminds, we count that as a win. So it sort of subtly highlights these other features that are in the membership that don't necessarily come out from us sending you a report and having an upgrade prompt in the report itself.

Akta [00:14:43]: I love that because one of the questions I was going to ask you was how you keep your readers engaged. And I feel like that seems like a really nice way to keep the community engaged and to showcase them as part of the newsletter.

How do you price your subscription and how did you come up with what the price would be versus the value?

Dru [00:15:03]: A lot of testing. So this is something I shared with Cortland from indie hackers a while ago, but we've experimented with lower pricing a lot, and what tends to happen with lower prices for us is that we run into members that need a lot of support. We have this thing when we're writing reports, we have a hater section in the reports and we talk about this idea of steel manning or like smart haters.

So you can't make an absolute statement and then try to defend that point because you've weakened your opponent's argument on purpose. So your job is easier. And bringing this back to the type of people that we attracted when prices were a lot lower. When I say support, I mean it would just be things like issues that we don't deal with now of what happens if I don't post my stand up on the weekend. If they read the onboarding documentation, then that wouldn't be a problem.

Dru [00:16:02]: But those are the types of issues that pop up at like a $99 a year or $150 a year that we don't have at our current pricing. More recently, we've also experimented a lot with lifetime deals and they seem to work for other people, but they just don't work for us. There were six tiers of lifetime deals that we split tested, and none of them outperformed our yearly pricing of 299 a year. So yeah, split testing again is a big part of my answer there.

Akta [00:16:33]: And how do you go about changing prices? So you've already got people who are already paying for the subscription and then you've increased your fees. How do you go about that without, I don't want to say upsetting people, but making sure your audience understands what's going on?

Dru [00:16:50]: Yeah, we take the easy route of always sort of rewarding people for being early. So whatever price you signed up at, we honor that price. For example, we still have some people on A-9-A month plan from gum road days.

So the easy decision usually leads to more loyalty. Member front. Yeah, so that's the path we've taken and there haven't had to be any crazy discussions around. We're going to upgrade everyone to this new pricing.

Akta [00:17:22]: Nice. And then let's talk about sponsorships, since that's your second main income stream, how do you go about pricing your sponsorships?

Dru [00:17:31]: Yeah, so we've experimented with pricing sponsorships a lot as well, and I've sort of recently settled on this idea that looking at the types of sponsors that we have, if we can get them like one to two conversions and that's their break even point for a single campaign, that's the pricing that we've gone with there because we have a lot of productized agencies that advertise with us as well as they don't technically qualify as a bank.

But like financial service companies like Mercury that have low churn and a high lifetime value. And then ironically, those have been like the repeat sponsors that we've seen, those types of larger companies with high lifetime values.

Akta [00:18:13]: Yeah, I had a look at your Passionfroot page and you offer a flat fee for a sponsored ad and then a package of three for a slightly reduced rate. Why did you go for flat fees versus keeping open to negotiation, talking to the brands and coming up with a price together?

Dru [00:18:32]: Yeah, so we had that at one point there was even a form of signing up where someone couldn't sign up like you had to go through that process. And we take a look at your brand and we talk about some ideas and there was so much friction and we just realized that this is a separate issue, but people will still try to negotiate even though we have pricing listed.

And I think those are the worst situations for us because we've went down that path several times. And there's a perfect correlation between a brand being harder to work with and a brand trying to negotiate down what we consider to be reasonable pricing. And what do, I mean, what types of issues are popping up? So things like if we have a deadline of Thursday at 10:00 p.m. Eastern to get copy back, it may come on that Monday.

So everything has the shift again in using process street where these aren't arbitrary deadlines. So everything has the shift on our part because we got the copy late or they're contesting click data that we sent on the back end because you still have to work with them in terms of, okay, how did this campaign perform? Yeah, there's a perfect correlation between those issues and someone being hard to close and someone being hard to satisfy on the back end.

So we're not only optimizing for revenue, it's also like peace of mind.

Akta [00:19:54]: Yeah. And have you found any effective ways to work with sponsors so that you can try and avoid some of these issues?

Dru [00:20:01]: This is an answer, which is that sometimes, like I said, people will still try to negotiate. It's not always about price, what they're trying to negotiate, but depending on how much back and forth, if we're eight or nine emails in, sometimes I may just say, okay, we're going to sort of opt out of this deal on our end because even closing the deal seems difficult and oftentimes that's sort of a preface for more issues later. So it's again making those sort of small early decisions in hopes of avoiding a bigger headache later.

Akta [00:20:32]: And once you've kind of finished that collaboration, how do you continue those long term relationships if that's something that you're striving for?

Dru [00:20:41]: Yeah. So we have a call to action in what we call click reports that we send. But these are basically performance reports of how did the campaign or campaigns, if they signed up for a package, perform. So we ask for qualitative feedback in that email. But there's also a call to action if you want to book another sponsorship. We haven't gone beyond that much. Yeah, we haven't gone further beyond those two things.

Akta [00:21:07]: No, but that sounds really good. I actually haven't heard of many creators who firstly send reports and secondly include a call to action within their report. So that sounds really good. How do you actually integrate those ads and those sponsors in your newsletter? What have you found to be quite effective in terms of making the sponsors happy but also delivering value to your readers?

Dru [00:21:30]: Yeah, the main thing that we've done, so we've had a very varied approach to how we get sponsors, but one approach that we also tried was doing outbound ourselves. And since we know which report topics are coming up, what we would do is we would align those topics with, okay, the audience that would be interested in this report would also be prospective customers of this business.

And that's worked out really well because you have that alignment between the topic and also the sponsor that we're going to reach out to. That's also been interesting because we've worked with an agency to do outbound for us and they are reaching out to ten or 20 times as many prospects as we would reach out to, but their close rate is much, much lower than ours. So we would reach out to like ten or twelve companies and have a very good close rate with those companies versus.

Yeah, we're working with the agency now that hasn't closed the sponsor and they've reached out to probably 3000 different leads. So that type of personalized approach of not only personalizing the email, but being thoughtful about, okay, what comes out on this date and then who would be interested in reaching the audience that would open this email?

Akta [00:22:49]: That's so interesting because you have such a large audience. I didn't even think that outbound would be something that you would consider. But I love how you've been very intentional about the sponsors that you're bringing on. How do you go about your pitch then? What are the sort of things that you include in those emails to these brands?

Dru [00:23:07]: Yeah, so we talk about the topics that are the topic that we're going to cover and why we reach out to them. Thinking about that and then there are just different sort of persuasive tactics. I think the latest form of this email we found that this doesn't help. But one thing that we thought would help at first is sort of mentioning not only them, but the other people that are going to be featured in the email.

It's pretty standardized where there's an image, about 150 words of copy, and a CTA with a lot of contextual links. So not only are you being featured in a report, you would be featured in a report anyways, but there would be that large ad at the top of the report as well. So yeah, it's mainly been talking about, okay, why are we reaching out to you? Why does this make sense?

Akta [00:24:12]: And do you include the price in that pitch and previous issues, or do you kind of wait until they maybe say, yeah, I'm interested?

Dru [00:24:21]: I'm not sure how we would do this in show notes, but our editor took over and is leading right now the outbound. So I have to look at the latest form because we're even split testing those emails.

I have to look at the latest form of that email to see if pricing is included or not. I'm 70% sure that it's not. If that person doesn't indicate interest, then that doesn't start, but I'm not 100% sure on that.

Akta [00:24:45]: I love that you're like split testing that as well. It seems like you're really into analyzing the data and actually getting something factual before you make decisions. So what other kind of key performance indicators do you look at or metrics to see the success of your newsletter and the impact that it's having?

Dru [00:25:04]: Yeah, it's mainly clicks. I noticed that a lot of newsletter operators, they talk about opens and I think opens matter, but it doesn't carry a lot of information. Once you sort of have a good enough pattern that you settled on for like a subject, and once you have that, it's really about the content. Are people taking action on the content? And that's why we pay so much attention to click rates. Click information.

Akta [00:25:29]: And have you found anything that optimizes that click rate? Trying to think of sort of maybe principles or some surprising things that I've learned about the key rate. Which words do you choose to have the link on or do you have a button? What works well?

Dru [00:25:49]: Okay, I have something, something that works well because we have a review stage of reports as well, which I didn't talk about that process where we look at how did this perform, and we record that for prosperity so we can look back and see what did we think went well and didn't go well. Something that always helps is when referencing sort of specific numbers. So for example, saying, okay, this SaaS company, okay, we're talking about an opportunity in a no code space.

This team built a no code app that makes over ten k a month that will not perform as well as if you say, okay, this SaaS app earns $14,652 a month or something like that. And then to bring it back to click information linking to that specific number. Right. Because you've already drawn more attention to that space and now people are interested in double clicking on that information. So specificity helps in this way.

Akta [00:26:50]: And what else do you look at during that review stage? I'm interested now that you've mentioned that.

Dru [00:26:55]: A lot of it is just the analyst experience. So I haven't written a report myself, like a full report myself in maybe 40 or 50 weeks. It's been a while. So it's asking the analysts what was the most painful part of this? And oftentimes we get feedback to improve our workflow based on their experience there. So it's not only about sort of external feedback in terms of how did the audience receive this, but health wise, organizational, health wise, what was it like putting this together?

We also recently, in the past, maybe three or four weeks, revamped our whole process to make it AI, assisted in terms of sort of getting the first draft of ideas back or doing cursory research for us, using AI in that way. And that was, I think, the most recent major overhaul of the process. And that was largely informed by us using these tools for other things and realizing, okay, this could also help us out. And that was mentioned a few weeks before we kicked off that effort.

Dru [00:27:57]: That was mentioned in this feedback stage of, okay, I think perplexity AI can help out here. I think we have being accessed back in GPT four. Maybe we can start using it at this stage or for this section of the report.

Akta [00:28:11]: So what does your current team look like, and how do you decide if you need a person or if you're going to be using AI or a tool to help with things?

Dru [00:28:22]: Yeah, that second question is really hard because all of this feels so new. But right now the bulk of the team consists of an editor, analyst, and then we have an operations person as well. And the team has fluctuated in terms of size, where we've had multiple analysts at once. We've had a developer at one time. We do work with a design agency as well.

Akta [00:28:47]: And when did you know that you were ready to hire?

Dru [00:28:49]: It usually comes from pain. At first it was pain of staging emails. So, okay, I put 40 to 60 hours into this report, and now I have to go through this is when I was the only analyst. I'm going through the familiar cadence of staging this report, and all I want to do is sleep. And there's no reason why I have to be the person to stage this report. I could record a loom video and just have someone else do it. So that came from pain. And then there was a period where it sounds silly to say now.

That's not the exact word I'm looking for. But there was a time when I'm like, am I the only person that can put reports together? Like I have a big ego? There was a time when I wondered that, and then I was like, let's just see if other people can do it. And I feel like now our editor analyst does a better job than I did in the past. But it took a year, year and a half to sort of refine our hiring process and then also find that person. It's very hard to sort of find people who will do the work that it takes for good writing and good thinking, if you will.

Akta [00:30:04]: Yeah, I feel like that's an issue that so many creators struggle with. What is your hiring process like now? What have you found to be effective to get the right people on board?

Dru [00:30:15]: A lot. So I think about this a lot. Maybe a long answer. The two books that were the most helpful, the manager's handbook, which is from Alex McCaw, and then a book that he co authored called the great CEO within or the CEO within. So some principles that we follow, we use test tasks up front. So there's like a test task that you use to apply. On the back of that, there's a paid test task, which you get paid to complete. The principle in that is at the point that we're interviewing, we're only interviewing for a vibe check because we've completely made sure that you could do the job.

And the paid test task phase may be more stressful than the job is because we're sort of trying to overprove that you can do the job. Absolutely. Make sure. And again, the interview at that point is just a vibe check. I think that was the biggest change. If you look at the, and I'm not sure how long this post will be up, we're looking for analysts right now. If you look at the application, you'll notice that we optimize for clarity. So there's a loom video on that page.

There's a style guide. We link to references for internal language that we use, like intellectual honesty and still manning. Yeah, we just try to be absolutely clear because that's one thing we've noticed in terms of, okay, we asked for this, but we got this on the application that you submitted. And we always try to be generous of like, how was this unclear? How could this be misinterpreted? So over time, we've gone out of our way to optimize for absolute clarity.

Akta [00:31:53]: That's so interesting because I feel like most people would share that information after someone's been hired versus before. So that's a really interesting perspective. I've not heard that one before.

Dru [00:32:03]: I have a point to add about that, if you will.

Akta [00:32:05]: Yeah.

Dru [00:32:09]: It pained me to provide all of that information up front because part of it was I want to see sort of how intuitive are you or how well can you pattern match? Because all of this information is out there, especially around analysts. If you can look at our recent reports and you can see the style of a problem statement or a solution statement, or the fact that all of our predictions have early examples and they're evidence backed.

And when I would sort of lean on that 95, 96% of the time, I sort of wouldn't get what we were expecting. So, yeah, again, it would be great to sort of test can this person pattern match? But that just did not work in our favor. The answer would be no. And we have to optimize for clarity.

Akta [00:32:56]: Yeah, no, I like that. I think it's an interesting perspective and for anyone who is struggling with the same problem, that might be something that they should try as well for their hiring process. What advice would you give to new set of creators who are trying to grow and scale?

Dru [00:33:10]: Yeah, I would go back to the thing that sparked Trends vc, which is around asking, what can you stick with? Because again, there are going to be periods where feedback is slow or non-existent or depending on if you have a full time job or if you're relying on this as a sole source of income, where deadlines that you have to meet and you may have not slept in the last 24 hours. So there has to be some type of inherent interest in that thing so you could stick all of this through. And I think that's very hard to do if you're just not passionate about what you're working on.

Akta [00:33:48]: Yeah, very true. I'm going to end now with a quick fire round. So I'm going to ask you five questions I ask every creator that comes on air, starting with, what's your favorite thing about being a creator?

Dru [00:33:57]: Flexibility.

Akta [00:33:59]: And what's something that gives you the most inspiration for what you create?

Dru [00:34:03]: Mastermind. So we have weekly masterminds with other founders and, yeah, I just always leave those calls sort of charged up. And it's just the ambient inspiration of understanding what this person and these people wanted in the past week, what they got done. And that's sort of this constant. There's this push in doing that. So you're just witnessing what other people, what goals they had, what they got done, and that pushes you to do more as well.

Akta [00:34:28]: Oh, I love that you do that. What's one tool that helps you as a creator?

Dru [00:34:33]: I have a love hate relationship with it, but Process Street.

Akta [00:34:36]: Okay, what's something that helps with your creator work-life balance?

Dru [00:34:43]: I go back and forth on this. I go between two major tools as like, my operating systems for life. One is Google calendar, so time blocking. The other is a habit app called every day. And it's weird because these two things can't coexist. Right now I'm using Google Calendar on Mondays where I have all of my calls and I have to be on time. And then when I have a little more flexibility, the rest of the week I use my everyday app.

Akta [00:35:10]: Nice. Yeah, nice. That sounds good. And what's one piece of advice that you'd give to other creators? So not necessarily just newsletter creators, but anyone who's in the creator economy.

Dru [00:35:21]: I’ll try to switch it up. But I keep coming back to that critical question because I think especially when a creator, especially when this sort of describes, like, the average pro member, it's a very highly skilled person. So it may be a doctor or a developer or marketer or a consultant. So they have relatively high income, but they don't have the flexibility that they want. And in that predicament, they often think about, okay, like, what will make money?

And then they may get what they want, but they're still not passionate about that thing. It feels sort of like an uphill battle. Right. So I keep coming back to this idea of what can you do for a while? And just to add or double click on that idea, that doesn't mean that the form factor that you have in mind or this exact idea that you have in mind is a thing that will work out, but the fact that you have that interest, it means that you're willing to stick it through and iterate until you sort of find that fit, that product market fit that you need, assuming that that kernel of what drew you to that thing is still there by the time that you find that fit.

Akta [00:36:33]: Yeah, no, I think that's a great question for creators to ask themselves, even those that have already started on their creative journey, because like you said, it's a process of reiteration. And then if you've got that question at the back of your mind, that can really help you kind of figure out what direction to go in.

Dru [00:36:47]: And it also matters a lot for compounding, right? Even if you, let's say, okay, you get to ten k a month, depending on your goal. If you're interested in compounding, can you do this for the next three, seven, or ten years? Because a lot of the biggest rewards are going to come from month, I don't know, 150 to month 160. You're not going to be able to compare those returns month one or month two, but you won't reach that if the flame burns out or if your interest dies out or if you just don't have the endurance or consistency to stick with it.

Akta [00:37:23]: No, that's a really good point as well, because a lot of our audience are creators who do want to scale and who do want to be in this for the long term. So thank you so much, Dru. This has been an amazing conversation. It's been really nice to hear how you've grown your newsletter and how you've monetized, and we really appreciate having you on.

Dru [00:37:38]: Thanks for having me.

Akta [00:37:39]: You can find Dru on Twitter, his newsletter, or his membership Trends Pro. And if you are a creator and you want to set up a sponsorship page like Dru, check out Passionfroot. We help you to streamline your entire workflow. I'll see you in the next one.