Dru Riley

Transcription:

Rob:

Yo, Dru! Welcome to the show, my man.

Dru:

Thanks for having me. Excited to be here.

Rob:

So most people don’t know that Dru and I actually went hiking in Cape Town only last year. And you are among the very few Yo podcasts I’ve actually met in person, along with John O’Nolan and Gilbert. Dude, it was cool just cruising up the mountain with you.

Dru:

Yeah. Yeah, you call it cruising. It was hard, but had a lot of fun. Had a lot of fun afterwards, too. Grabbing a bike to eat.

Rob:

There was a little bit of blood involved. It’s actually one of our most steep mountains in Cape Town. We just had to initiate you off the bat.

Dru:

Yeah. Jumped right in the deep end.

Rob:

So a little birdie whispered in my ear. You started the year off standing on a surfboard and riding on a wave in Peru.

Dru:

Yeah. I think I was inspired by one of our web based chats. You talked about looking forward to the (waves in lima), so I got out there.

Rob:

So you think surfing is going to stick for you, or is it one something?

Dru:

Yeah, so I went surfing in Mexico last year. This was the second time. It was a lot of paddling. I don’t know if it’s specific to lima (lima), but I have to get my stamina. I’m going to keep this habit.

Rob:

The learning curve is difficult. It actually separates a lot of people who think surfing is just kind of cool versus you got a breakthrough and then you earn it and then the reward really comes.

Dru:

Yeah. I had an amazing instructor, though, because it was a struggle in Mexico, but he had me up and going in no time.

Rob:

Nice. Okay, so let’s get right into a fun intermission called overrated underrated. I’m just going to give you a topic, a brand, a person, and you just need a quick fire back if you think it’s overrated, underrated, or properly rated,

Dru:

got it.

Dru:

All right, let’s go.

Rob:

The jiu-jitsu belt color ranking system.

Dru:

Overrated.

Rob:

Meditation

Dru:

Underrated.

Rob:

NFTs

Dru:

Underrated

Rob:

Avatar, the film

Dru:

Overrated. I haven’t seen it.

Rob:

Artificial Intelligence

Dru:

Underrated.

Rob:

Steve Jobs?

Dru:

Overrated. @ me!

Rob:

YouTube

Dru:

Underrated

Rob:

ChatGPT

Dru:

Properly rated.

Rob:

Influencer marketing

Dru:

Underrated

Rob:

Judo

Dru:

Properly rated.

Rob:

Twitter

Dru:

Properly rated.

Rob:

And lastly, Product Hunt,

Dru:

Properly rated.

Rob:

So if my research serves correct, you received over 20,000 newsletter subscribers of your various Product Hunt launches. Do you think Product Hunt is still a worthy hustle for newsletter publishers tuning into this episode?

Dru:

Yes, I think it still can be worthy over time. Like the effectiveness has gone down some, but it’s still a worthwhile effort. If you’re investing in a launch, you put a couple of days into it and it’s one of those things that can have asymmetric returns for you.

Rob:

We have Dale here from inbox authority asking ‘hey, Drew. Dale Dubowski from Inboxauthority.com. If you were starting the Trends.vc newsletter again from scratch, so from ground zero, what would be the single strategy or tactic you’d use to grow it? Thanks very much, guys.

Dru:

That’s so tough because it seems like a lot of things have changed. I’ll tell you the tactic that we use and if it was as effective as it was back then, I would just run that playbook back and it was around taking reports, breaking them into threads and mentioning the company and people that were featured in the report, tagging them on Twitter. I don’t know if that’s as effective now as it was back then. We also have to rewind three years ago and remember what was going on three years ago. A lot of people were stuck in the house, so that may have contributed to, like, the fast growth as well. But yeah, if that playbook would still work, I would rerun that.

Rob:

When I had the Yo! YouTube show, I used to release an episode every week, and it would be a hell edit, you know, like for a six minute video. And I remember I was so tired at the end and I had to think about distribution. I would just drop a tweet and it would fall flat. And then I’d be like, hey, cool, next, next video. Let’s go. And then I remember some weeks I would just tag the right person that would get it at the right time, and that retweet would just snowball the thing. And next thing you know, I had double the amount of views from one tag in one tweet.

Dru:

People love to be featured.

Rob:

So while we deep in hindsight, if you were to start again, the publication, you know, obviously hindsight is 2020, but if you were to start again today, how different would the tech step be to get started now that we have all in one solutions like Ghost to do the heavy lifting?

Dru:

Yeah, so my mind goes directly to the ESP site email service provider, where I want to use substack really, really badly. But what a lot of people did realize at that time was that you couldn’t set up custom domains. So that means that as you’re dropping all of these backlinks and breadcrumbs around the web, they’re going to the substance subdomain. And then, that was just a no go in terms of platform risk for us. So I don’t know how much extra work it was to not go with all in one solution like Substack, but bit the bullet and started out with Mailchimp. Now we’re more of like looking to switch again, but that added a lot of operational complexity to avoid that platform risk. So, yeah, we’re probably trying to go for a tool like beehive or even now Substack, you can have custom domain, so that could be an option. And then the other upside of that, is that we probably would need WordPress the way we use it now. So that was yet something else that was born out of the operational complexity of avoiding that platform risk.

Rob:

Where are you looking to go from MailerLite? I’m currently embedded in MailerLite with most of my lists.

Dru:

Yeah, yeah, I like that word embedded because we run a test tomorrow where we’re comparing the deliverability rates to make sure that we will transfer and hopefully even improve on beehive is what we’re testing. And if that doesn’t improve, we’re going to try something else. But we’ve tried working with MailerLite around deliverability, and support is very responsive, but not very fast. I hope that doesn’t cost us a sponsorship, but got real respect for that.

Rob:

We have Darshan here from Product Disrupt. “Hey, Dru. Darshan here from Product Disrupt. Long term admirer of your newsletter. So my question to you is, what are some of the practical tips that you would suggest to grow a newsletter from 5000 to 10,000 subscribers?””

Dru:

I would say it depends on the game that you’re playing. If you’re playing a paid newsletter type of game where Followers matters a lot and you need to justify that value at 5000, you’re sort of at the point where if you release a piece of remarkable content, it’s worth remarking about, that can do some of the legwork for you around distribution. So I would probably double down on quality if I’m intentionally playing, like, a distribution heavy type game think, warning group, for example, then I would just start putting the rails in place to make sure that you’re getting enough from sponsors to justify paid acquisition, partnerships, everything is on the table. But I would just optimize for growth. Right? And you’re probably not putting as much effort into quality at that point.

Rob:

Good take. So, continuing the path down growth, do you have a North Star for where you want to take trends pro?

Dru:

In terms of a number, I think about 3 million engaged email subscribers. And we don’t only define that as opens, but also clicks and interactions with an email on like rolling 30 day period. So that’s the newsletter side. But you mentioned Pro, and then my mind goes to the mastermind side. So on that side, it would be great to build up a network of, let’s say, at least 1000 active mastermind members just because I’ve seen the power of masterminds first hand even before Trends.vc existed. And yeah, that’s the most, I’d say, like, remarkable piece of what we do. Most people know about the newsletter, but I’d say we have the deepest impact per person from what we do on the mastermind side, The word that comes to mind is transformation, and you see it.

Rob:

My calculations are correct, we’re talking over 50,000 free subs, over a thousand on the pro. You’re talking about a 2 to 3% conversion from free subs to pro members.

Dru:

Yeah.

Rob:

You know, you have to have some funnels in place to grow this thing if you want to get to 3 million in 30 days. What funnels have you got penciled in? Do you have anything, like, really experimental?

Dru:

Yeah, I’ll say we’re inspired by a report that we did of site project marketing. So that’s this idea that you’re kind of building these, like, lead magnets. So let’s take a directory, for example, where that directory becomes, people are coming there, and then we’re also using that to push opt in for the newsletter. So we’re going after that strategy. And a few months ago, I took a serious look at paid acquisition, which that’s still on the table, but I like to treat even the amount, the money that we were spending paid, like, can I get a similar or better ROI by acquiring the tool, building our own tool, like, whatever that would cost us. So everything’s on the table.

Rob:

So MicroAcquire flip your browsing needs trying to find content sites to do with trends.

Dru:

I have in the back of my head because I know I have frizz that have sites or site projects that they sort of discarded or stopped tending to. So I’m thinking about that, but I’m actually focusing more on churn right now, which is kind of like lane-switch from talking about, like, top of the line free newsletter subscriber growth to get churn under control. So we’re not filling the leaky bucket, if that makes sense.

Rob:

It does, and it’s super important, I think Churn is the word on the tip of everyone’s tongue in January 2023. If you have a subscription business. Might as well turn out that TikTok which is just too much energy.

Dru:

Yeah. Yeah. This is sort of an adjacent point of the items last week for me was to think about getting back on the bandwagon in terms of, like, personal content production. My personal Twitter account isn’t very active. And the point there was thinking about out what type of system makes sense to start tweeting from my personal account again. And I arrived at this point of it feels like the type of content that’s had the longest lasting impact are, like, the longer essays, which can then be chopped up into tweets or Twitter threads or become a script or a YouTube video or a TikTok, where TikTok isn’t on a road map for us. But if it was, it would probably be something that’s derivative of, like, a longer essay or something in our robe.

Rob:

Yeah. Gary Vaynerchuk talks about his pillar of content and he creates one. And then he’s got his team to just make a 100 items. He’s just got such a good distribution. So I know you’re big on compounding. All the interviews I’ve heard from you is like, you love that effort. Why are you not interviewing big dogs like Seth Godin for pro members only, paying him, getting it there and then that content lives forever as a pro sign up incentive. And now you have a library of really exclusive, trend specific takes by the big guys.

Dru:

The funny thing is I’ve been in three masterminds today. Mastermind, right before this interview someone mentioned that, and I could add it to the roadmap and I talked about adding it to the roadmap then. But one thing that I also mentioned is this idea of like, focus. Like we could try to pour the ocean and do a million things where right now, yeah, we’re playing a lot of cards to approve the mastermind experience specifically around adding session ratings after each session, rating that session. I don’t know who said it, maybe a lot of people said it, but it’s like you can have anything, but you can’t have everything. So I’m just trying to choose the game that we’re playing and focusing on. Once we hit diminishing returns, then we can knock down the next domino.

Rob:

I think it’s super smart and that’s literally my next point. I said how do you divide up your day serving core community or trying to grow? You talk about the leaky bucket and you can throw all the staffed gardens in there. But if it’s a hole in the bottom it’s a bit of a bigger question, but what is the difference between a community and social media networks?

Dru:

When I think of a community, I think of a group of people having a very definite point of view on the world or like standing for something where when I think about a social media network there can be many communities within the social media network and some of them may even hate each other and actively fight. Also think that and this isn’t a definite thing, but I think that communities, it’s more common for them to suffer from negative network effects. Like more people that tend to join a community, the less valuable that can become sort of per member versus social networks. They figured out a way to like, sort the signal from the noise and the more people that join social networks, the more valuable they intend to become.

Rob:

I really enjoyed that answer dude. So this break into a second intermission, it’s called no context. Simply shoot back either of the two options I give you, no context given and no context needed at all. You got it?

Dru:

All right.

Rob:

Meditation or exercise?

Dru:

Meditation.

Rob:

Seth Godin or James Clear.

Dru:

Seth Godin.

Rob:

Atlanta or Florida?

Dru:

Atlanta.

Rob:

Bigfoot or Skunk Ape?

Dru:

Bigfoot.

Rob:

Do you know what a Skunk Ape is?

Dru:

No.

Rob:

Apparently it’s like take a Florida’s takeover, Bigfoot. Anyway, that was just some weird research.

Rob:

Surfing or hiking?

Dru:

Hiking.

Rob:

Open source or recurring revenue?

Dru:

Open source.

Rob:

Quentin Tarantino or Martin Scorsese?

Dru:

Quentin Tarantino.

Rob:

Sid Meier civilization or colonization?

Dru:

Civilization. They are ready before you even skim me the test notch.

Rob:

Teach or learn?

Dru:

Teach.

Rob:

Lead or follow?

Dru:

Lead.

Rob:

And lastly, masterminds or hackathons?

Dru:

Masterminds.

Rob:

Just swinging quick to remote work for a bit. Currently in Peru. You’re in Cape Town for a month. You’re a proper digital nomad. What’s in your work Backpack?

Dru:

Laptop. That’s a given. Keep three or four of these with me and I swap them out whenever I go back to the states for people listening, pointing to these journals. I don’t know how to pronounce the name, but they’re German. Yeah, that’s the same exact journal. Maybe you can add the names of the show notes. I swear by those. What else do I have? I’m trying to think about some like the usual kit. So I keep an extension cord, which, it comes in handy everywhere I go. Especially if you like places with patios. You can just run a long cord from the inside to the outside.

Rob:

What about a battery system? Like a little charging pack?

Dru:

Yeah, have a little charging pack. I don’t think I have anything that’s super unusual.

Rob:

A little laptop stand.

Dru:

Yeah, laptop stand. We’re using that now. Next stand. Sick is bad boy. Yeah.

Rob:

And that’s it. It’s pretty minimal standard

Dru:

Poor external mouse. Yeah, good stuff, dude.

Rob:

So with remote working, you’re trying to optimize your time so you can still explore the city. Obviously you work big hours. I’m last time I spoke to you, you spent a lot of the morning meditating and then you dedicate time and you’re only rarely going out on set windows of your trip. But there’s a quote that I read the other day by Alex Hormozi, okay. He talks about do not automate what you can systemize. And this one I can’t stop thinking and in the context that he had a whole bunch of gym owners (not clear) and there were a handful that had really low churn and he’s like they are definitely they have some sort of secret. So he got them all together, he had a big dinner and he just asked him like he just sat with every single one of them and said, what are you guys doing? What are you doing to keep the churn low? And then he collected all the feedback and he saw it as in common. And the one that really (not clear) stood out for him was that these owners were putting systems in place when people were not going to the gym and they were not sending this automated message going, ‘You have not gone to the gym, we would love you back’, you know, that’s automation. What he was doing, what they were doing is that they were putting in systems that would remind them, would ping them if someone wasn’t going to the gym. And then they would pick up their phones and message them and go, hey dude, haven’t seen you in a while, you know, maybe I’m heading there later. Just that personal touch. And he said that was just incredible for retention. So I want to know how automated are you right now?

Dru:

Yeah, maybe too automated.

Rob:

You’re the first guy I thought of.

Dru:

And I just started listening to Alex’s podcast. So I don’t know if that was like a poster or something that he wrote, but I love to listen to that episode. I’m working my way through the backlog now and that has me thinking. I don’t necessarily have any action items, but for every cart we created a Sprint, it has to be labeled as ‘hey it improves our brand, it improves the transfer experience, it boosts revenue, it saves us time.’ It’s the saving time thing that he just made me question, right, of maybe sometimes we don’t want to save time, right? You want to get that like high fidelity interaction and put that manual effort in. So yeah, now I’m thinking.

Rob:

What I love about your Trends.vc newsletter, the hot takes and the predictions. You know, since the newsletter is three years old now, it must be fun to look back and dig up those old predictions. Do you have some sort of prediction lug?

Dru:

No, I’ve had that because I have a lot of habits. I tried that as a habit. Maybe I need like a trick or something to maintain that. And I think I first got the idea from Farnam Street to basically have this prediction journal of, I think this is going to happen and then have a routine of revisiting those predictions. But I haven’t been able to make it stick yet as a habit. But I would love to.

Rob:

Okay, let’s dive back in. Looking at your landing page program like this, I’m already just picking it apart. I know no one asked me. There was no permission, but one of the things that I really thought of and just sidestepping, I’d love to actually critique your landing page, if you would allow me.

Dru:

Yes.

Rob:

Sometimes I’m planning to start a weekly landing page Masterclass newsletter, and I want to do critiques, deconstruction, share lessons, and I would love to do the Trends Pro landing page because it’s a one with a high conversion. It’s a serious landing page. But the biggest, so sidestepping back is that I just feel like the predictions are so fun and it is a feature. But what would be so great is if you could just date some predictions, some older predictions, and just have that, like, scattered on the page a little bit, like going, you know, from edition three and then you get to showcase what topic it was. But it’s like, we predicted this and then people like, whoa, dude, that was two years ago and this is fire right now. So just a couple of nuggets. I mean, just two or three predictions and obviously you can totally bury the ones you go wrong for your landing page.

Dru:

I like that especially because I was going to say especially because we’re running out of ideas for split test, so I will just add this to our split test log.

Rob:

Brilliant. So I want to do a weekly newsletter, but I’m terrified of announcing it and then publishing five and then I feel the burnout coming. Would you recommend biweekly to anyone who is just thinking about starting a weekly newsletter and you’re like, dude, you will eventually go biweekly, so you might as well just start there now.

Dru:

This might surprise people, but no. For whatever content type, like the fidelity of information, however deep that is, I would say go as often as you can. If you’re just starting out, your case is slightly different because you have these other projects that allow you to stay top of mind, right? Landing page, hot tips, one page, love, all of these other things. And you can simply like what comes on to your flywheel podcast. If someone sort of didn’t have this surface area and they were just starting out with the newsletter, they need to get that feedback loop spinning as fast as possible, right? So if it’s not super deep content every weekday or every day, if it’s deeper, weekly and then back out from there because you’re not only looking at, I have to stay at this cadence for three years or five years, it’s like, how do you get to that point of quality? And like it’s not going to be if you ever launched, it’s not going to be perfect. It’s never going to be perfect. But you know, how do you again, front load as much feedback as possible. So that would be the main reason that I’ll go for faster, faster iterations.

Rob:

Such a good take. I mean, it hurts when you say that because I know my podcast right now with my workload is, is basically monthly. That means I only get twelve out in a year. That means if I have two or three guests in a row that people aren’t that interested in, they don’t hear my voice for four months. And that’s not how you grow a podcast. I think maybe start off the newsletter for my landing page. Let’s go weekly for three months. They just get that feedback loop, just grow the subscribers like a big push and then maybe once you’ve got system we can go back to biweekly. But yeah, I just hate promising and not delivering.

Dru:

One comment something that may transfer to the podcast game that we did. We definitely felt a big hit when we went from weekly reports to biweekly reports. So we went with like a lighter content format to fill those gaps. And Founder Finds (not clear) is now weekly and for some people that’s their favorite content type after enough iterations, right? So it’s a much lighter lift for us than putting a report together, which often takes a lot, with Founder finds(not clear) we can pull that together in a couple of days. So mixing content types, right? Like, if you know, you really want quality guests and you have high entity standards for interviews, perhaps, and mixing that in with some other podcast content type. I like that idea a lot. And you got the crow cross promotion going so well.

Rob:

Back in 2020 you blogged 100 Rules of life and you’re clearly a person who loves habits and rituals, meditation, cold showers, training fast, I think journaling. Do you think these habits have made your life a lot more effective? And for people listening, they’re going, now this is some hippie talk. Is it the real deal?

Dru:

It’s the real deal. And if you don’t think it’s the real deal, I would say do it and then stop doing it and see what your life is like. I’ve been through periods where I stopped meditating and have almost gone crazy. I’ve become, like, dependent on these habits, in some ways. Cold showers are like an antidepressant for me. You might think your life is hard until you hop in a cold shower.

Rob:

That’s so good. Dru, a deeper question for a few people out there, and when I got hiking with you, it was amazing because I was like, hey, you want to have a beer after? And you were like, no, dude, I’m not drinking. And there we were sitting having a burger after, just keeping it tidy, and it was amazing and you don’t honestly need it. And for someone who’s kicked alcohol and is just focused on building, there’s definitely other people out there that are struggling. Do you have any sort of single advice or any little nugget just to help people into the next steps to kick it?

Dru:

Yeah, I’ve thought a lot about this recently, where it’s like I’ve taken that transformation or that move from drinking or not drinking. The principle that I learned from that is for me and for some people, elimination is easier than moderation, if that makes sense. So we could apply it to like, diet, for example, if you could say, like, hey, I have like a cheat day on Saturdays. I would have tried that in the past before I learned about myself, but it’s actually easier for me to not have cheat days than it is for me to have my cheat days on a Saturday. Because next thing I know is Wednesday. It’s like, man, I miss how cheesecake tastes and just get a little piece and then we just, it’s a snowball from there. That would be one thing to think about. It’s elimination easier than moderation for you. Right? It’s not the same for every person. Yes, a lot of people have great impulse control, but even that is like, sort of what do they say, willpower is a sort of limited resource where if you’re throwing willpower left and right, it’s going to eventually exhaust itself.

Rob:

That’s a great take.

Dru:

Just an extra point on the no drinking thing. It didn’t start out as like, hey, I’m not going to drink anymore. It’s just like an experiment. Let’s try to go one week and then one week turned into one month. And then I started seeing the benefits of more productivity, better sleep, less dehydration, better body composition, all of these things. Yeah.

Rob:

Brilliant. See ya Dru, I know we’re short on time. Thanks so much for chatting with us, dude. Here is a little Agro beat to end things off. Where can people follow your journey online?

Dru:

I would say just go to Trends.vc. I talked about Founder Finds (not clear) earlier, where I’m getting back to writing personal essays and a lot of them will be shared through Founder (not clear). So that would be the best place.

Rob:

Brilliant. Thanks, Dru. Take care, man.

Dru:

All right, you too.

Dru Riley

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