Ryan Gilbert - How to master the art of building and scaling curation newsletters!

as long as you're like authentic in your personal branding, whether it's a founder, you know, whoever, authenticity is what's going to like kind of do the job right now. So that's why you're seeing a lot of these agencies and things pop up that is doing LinkedIn content for founders versus the brand account. So that's where the authenticity comes in. Speaking from a person instead of a brand, I think goes a long way. People wanna hear from people. They don't wanna hear from a random logo on the internet. Right. So I think that's the biggest thing is just, you know, whether it's actually being written by you or not, or, you know, a team of people, agency, whatever. Having it come from the founder's voice is super, super important.

Welcome to the Undefeated Underdogs Podcast, where I unpack and narrate stories of ambitious people who turn obstacles into opportunities. My goal for this podcast is to create a platform to narrate underdog stories and maybe play a small, teeny tiny role in inspiring you. I intend to highlight the underdog mentality And make authentic conversations with people who play the long game, take action with a chip on their shoulder, and convert obstacles into opportunities. Buckle up as I'll be bringing some authentic founders, VCs, community builders, and content creators who got underestimated their whole lives, and yet they beat all the odds to become insanely successful. Now today I want to tell you a little bit about our awesome sponsor acquire.com. Selling a business is as tough as building a business. As someone who went through this process once selling my own startup, I know the pain it takes to get to the end zone. This is where our sponsor shines. Imagine this. You're a founder who's built a solid SaaS product, acquired customers, and generating consistent monthly revenue. The problem is you're not growing forever for whatever reason, lack of focus, lack of skill, or just plain lack of interest, and you feel stuck. What should you do? The story I'd like to hear is, you buckle down, somehow reignited the fire, get past yourself and the clichés, and start working on your business rather than just in the business. You start building an audience, move out of your comfort zone to do sales and marketing, and in 6 months you triple your revenue. The reality isn't as simple. Situations may be different for every founder facing this crossroads, but too many times the story ends up being one of inaction and stagnation until the business becomes less valuable or worse, worthless. If you find yourself here or your story is likely headed down a similar road, I offer you a third option. Consider selling your business on acquire.com. Capitalizing on the value of your time is a smart move. Acquire.com is free to list and they've helped hundreds of founders already. Go to try.acquire.com/sharath and see for yourself if this is the right option for you. Now let's get into today's episode. My next guest is a master of scaling newsletters through content and trends. I'm really excited to dive into a lot about picking trends and niches, but Ryan is the founder of Workspaces. I'm a big fan of Workspaces. a newsletter with close to 14K subs and 45K Twitter followers, which publishes desk pictures. You heard that right. Over 400 people, I was one of them, shared their workspaces and people go bonkers about it, including myself. I always go refer whenever I want to revamp my workspace just for inspiration. So it's so cool to see people's workspaces, to be honest. He recently also launched another newsletter called H1 Gallery, a collection of some of the best headlines ever written on the internet. Ryan and I, a quick fun tidbit, Ryan and I worked closely during our Product Hunt days. We had so much fun helping makers create content and do like a bunch of, you know, shit. He was also head of content at Loops, a YC-backed startup, and he did like so many things. So I'm super excited to dive into the conversation. Ryan, welcome to the show. How are you, man?

Awesome. Thank you. I'm great.

Yeah, I'm so excited to talk a lot of things, but fundamentally let's start like newsletter is such a hot topic even till today, right? Everybody starts a newsletter. You know, I run this thing called Founder Gigs. It's one of those mediums that get not popular, but it keeps on growing and growing on people's mind. So with you, you picked curation over creation. So I'm curious, like, what's your thoughts on directories, like curation, and when it comes to like launching a newsletter? Yeah, we'd love to know that.

Definitely. And I mean, yeah, like you said, literally everyone has a newsletter these days. When I started Workspaces, it was just before that trend kind of hit, I think, but right at the beginning of it. And I do think curation is a form of creation, just, you know, a little bit different. And I think that there's something kind of special about curation because if you do it right, you're basically picking and cherry picking like the best content from whatever your niche is and just like bringing that out to the masses. So not everyone follows the same people on Twitter, not everyone follows the same blogs, not everyone follows the same content, period. So if you're able to be the tastemaker for a certain topic and surface all that great stuff, I think that's a form of creation and I do think that it's super important. So With Workspaces, when I started it, that was really just looking for people that probably had a great desk just based on their title and where they worked and their creative kind of output and bringing that to the masses. Some of them were already sharing pictures of their desks on Twitter, some of them weren't, but really kind of going out there and just bringing them into the mix and telling them that I think people are going to be interested in where you work and how you work. And that proved to be true. And so yeah, in a way that one is a lot— it's still curation, but that one's a little bit less curation than my new project, H1 Gallery. But they're still adding, you know, a little bit of mix and your own personal kind of voice and taste to these things that makes it, you know, truly unique. It's not just like a handful of links or something, but I do still think that curating in that way is important and powerful too.

So there are like a couple of things you mentioned which I'm very excited to dive in deeper, but talk to me about tastemakers. Like, how do you think people should develop taste? Because I'm a big believer in having an opinion and expressing that opinion in a way that other people can be attracted to. And that's all about like having this, you know, developing this taste on either design, you know, startups, products, or whatever it is that you're into. So yeah, talk to me about like How one should develop or can develop having a taste?

Yeah, I think taste is like a very kind of unique thing. Everyone has different tastes, obviously. I think my unique approach to it comes from the fact that I don't live in a tech bubble. I don't have a ton of tech friends, honestly. I live in Wisconsin, born and raised in Wisconsin. My friends don't use Twitter, they don't use anything like that. So I'm able to kind of come in with a unique perspective and viewpoint on things. Maybe call that more of like the real world than some people on Twitter, honestly. And, you know, I'm able to kind of bring in what I actually think matters in, you know, real life things and bring that into the curation. So I think that plays a little bit into my taste. And I think some people enjoy that touch of it because it isn't the same people that you're seeing all the time on Twitter and things like that. You know, I kind of do move outside of that bubble a little bit. So I think that's important. And yeah, like I said, I think everyone has their own taste and you kind of do change and adapt it over time. So I don't know if you are able to kind of package up what you're thinking and liking at any given time. There's a good chance that there's another section of the world that also enjoys what you enjoy and thinks that what you think is cool or interesting is also cool and interesting.

I think I can relate to what you're saying, which is you have to hone in to your inner personality. You have to live in your own bubble to develop certain tastes. And I think one

of the

things I personally did when it comes to having a knack for, for example,

products is to basically try different products, like try thousands of products, just log in, see, observe, observe, observe, consume, consume, consume. And I think you kind of develop that by consuming a lot of content, good and bad. Like, it's not like you have to cherry-pick only the good stuff.

Yep.

have to go through some of the terrible stuff to see the value in the good stuff. Right. So I think that's my take is to just go bonkers on whatever the thing that's really interesting to you particularly.

So. Yeah, no, that's, that's 100% true. I mean, there's been some people that have like for workspaces, for example, submitted desks all the way back in, you know, 2021, 2022, haven't been shared for one reason or the other. I mean, maybe half of it's that I don't have like a perfect science to it. It's literally just. What I'm feeling when I go to publish, I'll go into my Gmail, type in Workspaces newsletter, go to unread and whatever I'm feeling that day. So it truly is like, what desk do I personally think is interesting that day? Or who's telling like the best story behind it? Or, you know, what is their role? Are they interesting as like a person? Right. Whereas other people might see a desk in there from 2 years ago and they're like, that is amazing. But it just like, it just for whatever reason didn't, you know, match what I was looking for at that given time. Not to say that it'll never be published or anything like that, but that's part of it. And then like for H1 Gallery, people are like, asking, how are you selecting these headlines? And so far it's just been, I spend too much time on the internet and it's just, it's just vibes. What do I like that given day is what I'm surfacing. It's just vibes. So it's, that's how I'm kind of surfacing the taste in that way. And it's truly just what does my brain gravitate towards on that given day or that given week? And some people might like it, some might not. It is kind of what it is. That's kind of the, you know, the cool thing about being a creator or, you know, curator or whatever you kind of want to call what I'm doing. Is not everyone's going to like it and that's fine. You will find your own little group and your own little tribe and just keep making the content for them.

I think the very important thing is to put your taste out. I feel that is the first fundamental step every creator curator should do. And I think, yeah, you're absolutely true. Like you're not going to please everyone. There'll be a lot of haters. There'll be a lot of people who like what you do and so you just have to ignore the first group and just focus on the second and just move on. So I love— and in your previous answer, you just mentioned about packaging taste. Do you have an insight that you want to share? Like, how should one package it, or at least from your experience, or build a narrative around, like, you know, a particular— in your case, it's workspaces, right? So talk to me about it.

Yeah, just in terms of like how I package everything up. In everything that I do, I want it to be super easy to digest and get into kind of how I was thinking about it. So when I do, you know, the newsletters or the tweets or anything like that, it typically isn't long form. It is like, can you consume this super quickly? And I'll add a sentence or two about why I was, you know, jamming with that in some way, but that's truly it. I want it to be as easy to consume and basically like, that's how I'm seeing it for the first time. On my end is it caught my eye super quickly. And how can I now push that out in the same way that I kind of discovered it as well?

It's about picking up trends, right? Is that what you're saying? In a way, I'm curious, like, what's in your opinion is the current trend that's like untapped or it's super small now?

Yeah, so it is all about trends. So going back a little bit before current trends, Workspaces started because of trends. Everyone was working from home or starting to work from home due to COVID. They were then, you know, posting pictures of their new work-from-home setup online, whether that was them working from a kitchen counter, kitchen table, a couch, or some people had crazy setups already at home. So that was definitely hopping on a trend, you know, a little bit earlier than other people did. And it was, okay, this is happening. How can I, as a non-technical kind of, you know, creative person, take advantage of this? So I could set up a Substack in 5 minutes. I could DM a couple friends and we could go on from there. And that's really what that was. That was hopping on a trend that I saw happening pretty quickly from my very, very small Twitter kind of bubble and, and growing from there. Current trends, how H1 Gallery, for example, started. I keep seeing all of these gallery sites everywhere, whatever it's about. It could be, you know, navbars. Yeah. It could be just really good design. And they all seem pretty popular, but a lot of them are showcasing, highlighting the exact same websites because, you know,

they

don't all even have the same taste, but a good website or a nicely designed website typically is, you know, consistent across the board. And so what I realized is, yes, people love nice looking websites. They like nice looking desks. They like nice looking things. It just, that just happens. But there's a giant marketing community out there as well that, you know, they care about design. But that's not all they care about. I mean, they care about copy, they care about email, they care about headlines, they care about all that sort of thing. And I mean, this really kind of hit home when I was at Product Hunt with you. A big part of a Product Hunt launch is the tagline. You see that before you even see the website design. If you're going to click into the launch, the tagline, the headline is what needs to draw you in. And so I kind of flipped these other gallery sites on their head with like Okay. People love these designs. They love these gallery sites. They're having a moment. They're everywhere. But how can I put a different spin on it from a marketing perspective? And that was just really how I did that. So the trend was gallery sites are everywhere. I mean, every day there's a new gallery site. There's even people making Framer templates for these gallery sites. So how can I make a gallery site curate as easily, as easy as possible and, you know, put a spin on it? Because I didn't want to just be another, this is a great design. That was not going to go anywhere. I mean, I'm not a designer, so,

sure.

You know, it would seem a little weird.

No, I love that. I think you're absolutely true. I feel the one-liners for some reason are so attractive, right? Even on Twitter before this was like, before the 280 characters days, everybody used to crave to express their their thoughts in that 180 characters, 140 characters, whatever it is. And it's so fascinating to hear from you that, yeah, it's already existing, the directories and the galleries. You just have to like pick a specific niche that is like, okay, people who are into headlines. And I think everybody's into headlines. We just don't talk about it much, especially people on Product Hunt. I've helped so many founders. Same. And the first thing, yeah, you and I think we kind of do this on a day-to-day basis. And the first thing we say, Dude, you just have to craft your tagline. Repeat, write 100 of them, right? So that is, I think that's itself is a framework.

You

have to go in a broad trend or approach the trend in a broad way, but your entering into the market strategy is picking that one simple thing, like that's really like popping out. I really love, now that we're talking about H1 Gallery, unlike workspaces, You took a good chunk of time to design the website. And by the way, it's fucking phenomenal. I absolutely love it. The hover and the small tile design, the about section, everything is so well thought out. So talk to me about the inception. When did you get the idea? How long you took, you know, to craft the website? Who helped you to like build it? And I'm just curious about the whole process.

Yeah, definitely. So I had the idea originally. you know, maybe like 6 months ago, did nothing with it. Actually ended up curating one of those designy type websites for someone that runs a very popular one, which you can find a tweet that says which one it was probably somewhere, but was doing that for them. And I was like, okay, like, this isn't hard to do from, you know, managing the website side of things. So why can't I do that? So that kind of like was the seed of the idea. But obviously again, it was like, I don't wanna just do another design one because that's just not me. Yeah. Um, curating it was super easy because I'm already on the internet all day. They've seen what I did with workspaces, things like that. Um, so that was the idea. And then I DM'd someone else that was also in the design space, just with this random idea, wondering if they could, you know, make like a design for it. They didn't have time, but they were like, this idea's awesome. You need to like commit to it. So that night bought the domains, um, have h1gallery.com and h1.gallery. And from there sat on them for probably another 2 months. So this probably all started back in like January and then basically started thinking like, okay, these side projects, like workspaces is exactly what got me into tech in the first place. So in 2023, I did zero new side projects. That seems, that seems wrong. It seems backwards. So I need to get back into that and I need to like force myself to do it now because if I just keep saying like, okay, next week, next week. Yeah. You know, life happens, things always come up. Like it's just easy to say like, I don't have time.

Yep.

So yeah, basically decided, okay, I'm for sure doing this. And actually the person, his name's Priyank, he designed the first version of Workspaces for me in Webflow, reached out to him and yeah, he designed what is now H1 Gallery. We kind of worked on it together. And one of the main things that I said from the start was that the Tagline has to show first and then on hover has to show the design. That was very intentional from the start. And then the rest of it, I mean, he kind of ran with the design side of things on his own. So he's great and yeah, helped kind of bring that idea to reality and that's built in Framer. So now, I'm not technical, but once like the V1 of a site's up, I'm able to kind of work within Webflow and within Framer to just make small tweaks based on feedback. But For anything major. Yeah, I just go to him honestly at this point.

Yeah, it's so— I think Rob Love tweeted about it.

Yeah,

you know, I think it got featured in One Page Love, if I'm not wrong. Yeah, there's so much love. It's so much love. And I personally loved it. Of course I subscribed immediately.

And you shared— some of the people that have shared it, subscribed to it, followed me because of it are truly insane. Like CMOs of, you know, multi-billion dollar companies. Someone that I personally really, really look up to in the marketing world followed me because of it, which now it's kind of like scary. I mean, I haven't even published the newsletter yet and I am kind of like, yeah, getting imposter syndrome with how is this even going to turn out? Because the reception's been great so far and I definitely didn't anticipate that when I did the first tweet, you know, 6 days ago or whatever it was. I planned on 50 subscribers before I send the newsletter was the goal. And that happens right away.

And I think 2 things I just want to highlight. One is side projects are so underrated even till today. Everybody underestimated because it's like, you know, throwaway projects. It won't get you much traction. It's not a business, real business. So many bullshit answers you get, but I think there is, there are so many upsides of just launching a project. Also, there are like so many downsides too. Like I'm not saying Everything is not going to be like super success, but I feel that's one thing.

I think people should start building more, more, more, putting themselves out. And like you said, I think, yeah, if you weren't shipped H1 Gallery, those follows won't happen.

Those shares won't happen and those people won't recognize or at least identify you. Right. So I think there's always an upside for a side project. And in number 2, I really loved what you said about having the expectation of 50 people. Yeah.

Very small.

Even though you have like, yeah, very small. Like even though you have like 14K subs for Workspace and like 40,000+ for Twitter followers and all that, that's the way to go. Launch a side project, keep low expectations and really have fun. Like once you have that 3 elements as a formula, I feel everything's super possible.

Yeah.

I love that. I'm waiting for the first edition to drop. I'm excited. And I saw a couple of examples. Voice Notes is one of them, one of my favorite products. Love it. Love the vibe. The vibes are different. And I'm sure you're planning some merch or some sort as well.

Yeah, I mean, same for Workspaces. Kind of want to get more into that sort of thing outside of sponsorship, just for, like, honestly, just the creative outlet more than anything. For both of them, I think there's you know, kind of fun opportunities that go along with just the traditional newsletter sponsorships, that sort of thing, which will be cool. And then, yeah, like you said, side projects are, you know, awesome. They literally changed my life. And I've written about it, you know, a few times for different places at this point. But side project marketing, even for big companies, is a massive, massive opportunity. And if it's a side project, I mean, like Even if you do fail with it, it doesn't truly matter, but it's a super kind of cheap, organic and fun way to, you know, drive potentially real, you know, business to your core kind of offering. So I think, you know, even outside of me, I think all businesses should do side projects as a marketing channel. I mean, that's literally how Airbnb started. They did a cereal box. So I mean, now look at them.

Love that. Love that. Now, yeah, let's talk about newsletters. I am curious, you know, we've launched to Successful ones. And talk to me about the tactics behind how to really go from scratch, from 0 to 1 when it comes to newsletters. What are the things that you did that really worked well you want to share with us?

Yeah, I think everyone should do this. I think there's an angle that you can do it regardless of what the newsletter is. So when I started Workspaces, I had zero following on the internet. Zero. I mean, and so my hunch was, you know, I can't grow this on my own. There's no way. I can't rely on a product launch. to make this work. But what I can do is these are other people's desks, they're other people's personal spaces. If they're willing to take the time to give me this content, they're also going to be willing to share it for me. So from the start, my hunch was I can curate this newsletter in a thoughtful enough way that I will be able to piggyback off of all of their audiences. And I mean, that worked. So then from there, I was slowly just getting guests with bigger and bigger followings. And every time I share it, I think literally over the last 450 editions, only 5 people haven't shared it after I have. So, you know, that's how I've grown 100% is through my guest audiences. So with H1 Gallery, also planning a very similar strategy, obviously, you know, I'm working with brands. I don't think the brand themselves will be as keen to share it, But there are marketers and people behind those headlines that had, you know, a hand in crafting it. Yeah. And I think them being able to tell the story about how that worked and the process behind it, I think that's the angle to take to get them to share again. So yeah, I think no matter what your newsletter is, whatever your kind of angle is, finding a way to tap into an outside audience that's probably bigger than yours and having them share basically on behalf of you. Is the way to do it.

Yeah, I think it creates that ripple effect, right? Because once you put it out and once they put it out, then the more people will, you know, see, and then you get like that snowball effect. Exactly. I'm curious, anything that you tried that didn't work, like any experiments that you kind of tried while you're launching the newsletter, growing the newsletter, like, hey, you should avoid this?

Yeah, no, tons. I mean, and then for Workspaces, it's almost 14,000 now, and that's all been organic word of mouth, zero paid acquisition or anything like that. So there's definitely a lot I can still do. But one thing that has failed, I think, pretty spectacularly is Instagram for it. So it's grown massively on Twitter. It's got, like you said, 45,000-ish followers. You know, it's followed by, you know, some crazy big name designers. Instagram, it has not grown at all. It's 2,000 followers, which is weird to me because it's such a visual platform, you'd think. That just swiping through pictures like that, it would've grown crazy. Maybe I just don't know how to use Instagram. Definitely a possibility. But yeah, it hasn't grown like I thought it would. I thought the Instagram would easily be the entire time 2x the Twitter account and it hasn't. So that's a failure. Sponsorships has been hard. It was very, very easy 2 years ago, 3 years ago before it was acquired. Since I've spun it back out, different landscape for newsletter sponsorships, I think as a whole. Yeah. So that's been harder. Doing the waiting for inbound interest is not a strategy anymore. I don't think for a newsletter like mine, I think I do need to do more cold outreach to get the right brands in front of it. Right. So that's more of a failure on my side of things, I guess, instead of just relying on what worked before. It's just not working right now. So there are still sponsors. It just isn't as easy as it used to be. And then, yeah, in terms of growth, I think waiting 4 years to do any sort of paid acquisition when a newsletter's already this big, I think is probably a miss. I mean, growing to 14,000 completely word of mouth organic is amazing, but it could probably be much bigger at this point if I would do paid acquisition. There's tons of people doing paid acquisition in the newsletter space. It clearly works. It's just something I haven't done.

Yeah. And what are the things that you're kind of It's not a vision per se, but you're kind of improving on top of what you did with Workspaces. I'm curious on the newsletter side, any experiments that you're in your mind like, okay, I want to do this in the next few weeks apart from H1 Gallery, which is, you know, which is a different topic.

Yeah. So I kind of hinted at this. I definitely want to do things more in the physical space a little bit with these projects, like kind of in tandem. So It should be probably no secret that this just makes sense for workspaces. I love workspaces. I love desk pictures. I also love coffee table books. Those go hand in hand. Mm-hmm. So projects like that, I think will be super cool to work on, another creative outlet. And that's just taking the learnings that I, you know, got from the digital sense and how can I bring this to a physical sense that actually like, you know, has staying power and lasts a little bit longer. So kind of taking the digital learnings, taking them to like a real-world product, which is— that's more of just like a passion thing. I just— when Workspaces is finally over for me, whenever that is, whatever that looks like, I want there to be like a book right there that just is a reminder of like what it did for me.

Wow, I love that. Yes, you're manifesting a physical coffee book which has all the tests.

Yes. Yeah.

I love that. I love that, man. I think that is so cool. And I feel there is something there, like maybe, you know, convert some of the work desks into merch, maybe something like that. You can wear it.

Yeah. And honestly, that won't even be to make money. I don't even— I don't care what that goes for. That is just like a personal, I want this to exist. So that's how that'll go.

Nice. I love that. I love that you're going from virtual to physical. You said briefly about sponsorships being hard. I can empathize with you and I'm kind of in the same boat. You and I exchanged notes and you shared some tips. Yeah. What changed that happened? Do you think that there was like sponsorships were a no-brainer a few years ago and now it's like super hard?

Yeah, I think everyone has a newsletter now, so that changed a little bit. There are newsletter platforms that allow you to have, you know, a built-in ad network that it's easy for brands to just say, I'm going to dump X amount of dollars in here and it can be distributed to all these newsletters without me actually like truly managing things. So for the individual creator that's not leveraging those right now, it's a lot harder to get those one-to-one connections and, you know, do that when a lot of brands right now are just like set it and forget it. And then also 2 or 3 years ago, every company had way too much VC money just pouring out of everywhere. And it was, what can I do with this? Oh, I can sponsor newsletters. That doesn't exist right now. So kind of the perfect storm of, yeah, money dried up a little bit. Everyone has a newsletter. There are easier ways for brands to just dump money into all of them on like kind of a scattered approach where it's just more work. You have to do a lot more handholding if you're not using those things to get the sponsor dollars. And then, yeah, but I think there's other creative ways you can earn revenue outside of sponsorships as well. But I think that's the biggest change. And then also as the newsletter gets bigger, it's been around for— Workspace has been around for 4 and a half years now. People don't look at it and I mean, it's been acquired. I spun it back out. Some people missed that whole spinning it back out thing. Right. So at one point it was owned and operated by a YC-backed venture-funded company. So people that think that that's still the case, or people that just are like, okay, this newsletter has been around for 4 and a half years, it's no longer like this small little publication where people want to help really and be like, hey, like, I just like what Ryan's doing, so let's just like support him and doing that. There's still some of that, but that was—

Yeah.

Very, very popular in the early days of me sponsoring. People were just like, hey, We love what you're doing. Don't care what the ROI is on this. Just, you know, let's have fun with it. And I think once it gets to a certain age or a certain size, or people have a belief that it might be associated with a bigger company that it actually isn't, I think that changes things.

Right. Yeah, I think right now. Yeah, absolutely true. That's a great insight right there, which is earlier, generally people used to support. I supported so many creators on Gumroad. just buying their products just for fun. Like, you know, $10, $20, that's fine. You know, you just buy it even though I didn't use— I didn't— I would never consume some of the things, but it's so much kind of putting the positivity out, right? And I think nowadays everybody's trying to optimize it. Like, what is the, you know, dollar to buck? Yeah, for sure.

I mean, I've done the same thing. Like, I've bought Framer templates from people that I'll never use just because like, hey, people supported me when I was starting out. I do like your template. I just don't have like an actual use for it right now, but like I'll buy it because I see it.

Right.

And I think as even those creators go further and further, that'll happen less and less because people are going to be like, okay, you aren't just starting, you have 30,000 followers, you don't need my help right now. And I think that kind of changes things a little bit.

Yeah. And any, any experiments are you right now doing that brings you sponsors inbound or what, you know, even outbound? Like, are you trying to do any or any tactics that you can share with us?

Yeah, so I've done these a handful of times, and I think I need to do a lot more of them. But for workspaces, giveaways are a huge thing. And to this point, I've made $0 off of them. They're just, you know, a company supplies a desk or something like it. We do a giveaway that's typically like retweet and subscribe to win. And then I select a winner, they get the desk, one person ends up happy. Hmm. I think there's, and I don't, I don't like charge for that. It's just like, hey, a brand supplying this $1,000, $1,500 desk. I'm happy, brand's happy, one person ends up happy. I think there's a world where the next giveaway or next couple giveaways, instead of it just being retweet and subscribe, it'll have like an actual sort of like a lead magnet type page. Those subscribers will be, you know, in their own little bucket, their own little world that they live in. And then from there, I won't exactly like give the emails to the brand just because I don't know how I feel about that. Yeah. I don't know, even like when it happens to me when I sign up for something, but I think there's a world where congrats, you know, there was a giveaway. One person won, 500 of you signed up. Typically the other 499 get nothing. But now this brand, we can send a second email to them that might cost them something. We'll figure that out. But you didn't win. but here's 25% off, or here's like a $25, $50 gift card or something. So like, you didn't win, but you clearly like the desk, the product, the brand. Here's something to kind of keep you in their orbit. Yeah, there's something there. I don't know.

Yeah, I think you're talking more on the likes of gathering these believers in a brand, right? And I feel, yeah, there is something there. I feel you should experiment for sure. I would love to hear your thoughts post the experiment because It's really hard to find believers these days. Like we discussed, it's all optimization. Like how many people— I don't care really about the waitlist I'm building. I care about the conversions. Don't care about the whole list. So potential target leads and whatnot. But I think that's a great idea. I'd love to see you implement that. There's something there for sure.

It would be less of just like selling the leads back to them. more of like, hey, you have an opportunity to like connect with these people who cared about you in a way that, you know, is probably unique because a lot of those brands, when they are doing giveaways on their own, I don't think they're getting the same amount of reach as, you know, a dedicated workspace newsletter, blog, Twitter account that kind of pushes them. So that's, that's fun. I do like the giveaways. They always, they always go well. Don't know if there's an angle for that for H1 Gallery to tap into, but right now, They are the biggest growth lever for workspaces since I'm only doing like organic word of mouth. I mean, you can imagine people like free things and when it's a $1,500 desk, they really like it.

Yeah, for sure. Yeah, I love these ideas. I think there is, if we get into more details, I think there is a chance if it works as a, you can turn it into a product where It's not about a brand, but about a niche. Like if you're into founders, sign up to this and people who are building for founders, you can say, hey, I have this 10,000 massive list of, you know, founder people, founder fans, and you're building for founders. You get an opportunity to like, you know, share some of the things with this 10K. I think there is like something there.

There's a newsletter called Today in Design, which I love, and it's written by Cole, and I don't wanna butcher his last name, but he is, you know, writing a daily design newsletter. So very dedicated, you know, niche newsletter. And he's now doing giveaways with brands that, you know, are very close to the design community. So it's win-win for everyone involved. People are getting yearly subscriptions to design-related things. He's growing his newsletter from referrals because of it. And people, you know, the brands are getting in front of a very targeted group of people. So I think, like you said, that's just, it makes sense for people when, you know, whether it's founders, designers, you know, engineers, whatever it could be, finding that angle and finding the right brands to get in front of them. So for me, desk companies makes a ton of sense. And for a lot of those things, those items are very high ticket, which, you know, is beneficial to those brands specifically.

Yeah, yeah. Nice, nice. And yeah, let's talk about like before, yeah, I wanna ask about a couple things before we dive into, you know, your expertise on content. Yeah. Talk to me about the whole experience at Loops. You know, you were the head of community there, head of content there. I'm curious what kind of content experiments you did that really worked well for early-stage founders who are listening. They have to either replicate or they can like, you know, take inspiration from something that you did at Loops.

Yeah. I mean, I think you could argue that none of it worked because I'm not there anymore, but yeah. But one thing that I think, I personally think was starting to work, Mailchimp does a really good job with their marketing glossary. It drives them tons and tons of traffic per month, something to the like 500,000 organic viewers. And at Loops, we started doing a similar one for email marketing terms, and we were ranking number 1 for terms like email body, body of an email, things like that. Was that traffic truly converting to customers? Probably not. I mean, Probably not, but you know, we were ranking highly for email marketing terms, which, you know, in some ways important. So the glossary was starting to work. Also wrote a 16,000-word guide on how to send emails as a SaaS company. That's—

wow.

Yeah, that was basically like a book. And, you know, while that like did, you know, okay in Google, that was more so like, hey, we are the experts in sending emails as a SaaS company. So people that came across it, typically enjoyed it, found it useful, things like that. So that was the hardest thing I think I've ever written from either school, business, whatever. And that was just, that was the hardest thing I've ever written. So proud of that. That worked in one way, you know, and then the glossary was another cool thing. And then another thing that, you know, is ranking well on Google, still see them when I look up email examples. There's a directory of email examples over there that we started that is basically When a cool email came across my inbox, screenshotted it, dumped it in there, said why it worked, what the subject line was, kind of an H1 gallery type approach to emails. So that was another cool thing and that was a fun little spin on content that was outside of the typical, you know, here's a blog post. It's doing well SEO-wise last I saw, and it was fun. So

yeah. Nice. That's cool. Any, Yeah. Do you have any tips for people who can't afford to hire someone who can own content, but founders especially, but they have to do content? Like, any other ways that you suggest them to go forward, take the first few steps?

Yeah, I don't think I'm the greatest at doing content for other people typically. Now that I've had time to kind of reflect on that, at least from a brand perspective maybe. But I think as long as you're like authentic in your personal branding, whether it's a founder, you know, whoever, authenticity is what's going to like kind of do the job right now. So that's why you're seeing a lot of these agencies and things pop up that is doing LinkedIn content for founders versus the brand account. So that's where the authenticity comes in. Speaking from a person instead of a brand, I think goes a long way. People wanna hear from people. They don't want to hear from a random logo on the internet. So I think that's the biggest thing is just, you know, whether it's actually being written by you or not, or, you know, a team of people, agency, whatever, having it come from the founder's voice is super, super important. Just goes a long way.

I love that. Yeah. Let's talk about content. And I'm curious to hear your thoughts and your experience. You know, you've done a ton with Looms. You are doing, you know, a lot now and you did so much as well during Product Hunt days. I'm curious on, yeah, these trends that pop up right now from a content standpoint. If you go on Twitter, I only see screenshots. It's like written in a very nice screenshot-y way. Take that, either they write it or they take it from somewhere else. Yeah. That is like The viral trend right now. So

yeah,

talk to me about like content strategy. If you want to build a content strategy in 2024, where should they start? Again, what are the things that they should avoid?

Yeah, I think that you should, if you're a B2B company, you should avoid memes. I think that's, you should avoid that because you're really— yeah, I'm in that boat. Yes, your account's going to grow. It's going to grow fast. Those people aren't buying your product. So turning your B2B Twitter account into a shitposting account, stupid.

Yeah.

Yeah. Cool. Your account's going to grow. It's not going to convert. And I know there's specific people who are going to come at me for that.

You should tweet after this.

Yeah. So that's just my personal belief. And yeah, I think just seeing trends before they fully take hold. So like you said, there's a lot of screenshots. People are doing things like recapping longer form guides like PG essays into a one-pager on Google Docs, screenshotting it, sharing it. They're going crazy viral. So seeing that before everyone else does it is important because if you're the last one to that trend, you just look silly. You don't want to be the last person on any sort of trend because you're now the brand that's Late to the party, you look funny and it looks like you're just desperate for attention versus actually being authentic with it. So I think that's the biggest thing, spotting the trend early. If you're going to do it, do it quick. And if you're not, that's fine. Hold off. There's nothing wrong with a B2B company not hopping on a trend. Sometimes for a B2B company, it's better just to be quiet, honestly. So that's the biggest thing.

Okay.

And then from like a personal standpoint of like side projects, which is I think where I really thrive on like the kind of smaller scale sort of marketing, it's just making it super digestible. Even though you might pay for Twitter Blue or whatever it's called, where you can do a super long-form tweet, having it where it can just be read and seen in 5 seconds without reading paragraphs is the way to do it. People have limited time in the day. Our attention spans I think are shrinking probably by the second because of the internet. So just Making it as easy for people to consume what you're trying to say and do is super important. That's probably done through visuals. Honestly, Workspaces works because it's visual. H1 Gallery will work because it's visual. Um, and I think that that is the biggest way to kind of market a side project is making it visually appealing, super quick and to the point. People aren't going to read your stuff if it's, you know, if you have to hit show more on Twitter, you kind of just lost.

We love that. You talked a lot about like trends. Yeah. What's the current trend, content trend that, you know, people should pay attention to? And also I want to ask about personal branding, right? Like, you know, what is your take on, you know, founders building a personal brand and what is their content strategy should look like? 2 questions right there.

Yeah. Current trends. I don't know. What is the current trend?

What's, what's What's tickling you when you go on Twitter? Like, oh man, this is actually—

Honestly, my Twitter is broken right now. So maybe this will just kind of be a trend. Maybe not. My Twitter account is completely broken, especially the For You tab. I'm writing a design newsletter, which is ironic. Like I kind of mentioned before, I'm not a designer, but I do write that for a different brand. And all I do now on Twitter is basically act like a designer, interact with designers, bookmark design type tweets. And my For You tab is just all design stuff. So I guess the current trend in my world is just probably not even like real, is just, you know, I don't even know, like design stuff. Like, yeah, I don't

know.

I don't know. In terms of like personal branding. Yeah, I'm sorry I'm not more helpful with the trend thing. I just broke my— No, no, no,

no. All good.

Personal brand, I think, is just like being consistent across everything. I mean, if you look at like the logo of all my projects, even my Twitter like profile picture, it's all very, very similar. If you come across the logo or, you know, like the little picture of one of my accounts, you can probably tell that it's related to another one without even knowing that it's me. And that's by design. They're using very similar backgrounds. They're using very similar pictures. They're following very similar formats. So I think the consistency there is super important. I don't want something to be just wildly different from the other. I mean, the projects are all similar in their own, in their own right. So I think that plays into it a little bit as well. But I do think it's important for a person, founder, creator, maker to build their own personal brand outside of a brand account. When I started Workspaces, it didn't have a Workspaces Twitter account. It was my own. It just got so big that I had to create its own, which was probably for the better to kind of separate it from myself. But I am, for better or worse, like the Workspaces guy on Twitter now. So people just send me pictures of their desks in my DMs. On email, all this sort of stuff. And it's like, hey, I have this much room to work with. What should I do from like a setup perspective? And I'll get these DMs at like 10 o'clock on a Sunday night and I feel like I have to answer right away. So I think just consistency over time, you just essentially end up building a brand that if you're being authentic and consistent, it just becomes kind of what you are. People consume your content, you become that person. And so yeah, from From a personal standpoint though, you just need to build your own list. You need to build your own brand because at the end of the day, people aren't going to interact with a branded account like they used to. And I think that's going to get more and more extreme over time.

Yeah, I love those personal branding tips. Last thing, I know we're on time. You're going to be a dad. How are you feeling? How are you feeling about it? It's a big change. I was there before, so Yeah. What's going on in your mind? How are you taking in— does it sink in yet?

Yeah, no, I'm super excited. Yeah, we're having a baby girl in basically 2 months.

Nice. Congrats.

Yeah, so very excited for that. Yeah, I don't know. It's super exciting. I probably won't work much when that happens, right? I don't know.

You will lose a lot of sleep for sure.

I've heard the sleep thing is going to be crazy. I used to operate really well with no sleep, um, back in, you know, college days, or I at least said I did. I probably— my wife would say that I actually didn't, and I was just like, you know, cranky all the time. Um, but I have to get used to that, I guess.

This is a different ball game, my man. It's, it's, it's different. I think college days I used to like pull long nights off as well. Yeah, this game is different.

Yeah, so I'm We'll see how that goes. I'm very excited. Probably going to be very sleep deprived. Hopefully I don't get cranky. Yeah, I think we have like this little baby book about like month to month what's happening. This might even exist. Yeah, this might exist already out in this world, but I think it would be super cool and someone could probably make a killing on this, probably already are. If there was like an email newsletter that was basically like you're selecting, are you expecting you know, in what month are you? Because like everything kind of is different, you know, what are you in? Like just like a weekly email drip of like, here's what's happening this week. This is what you can expect. Here are some products that you can buy to make this easier. Boom. There. Million-dollar idea that someone probably already did.

Yeah. Yeah. Yeah. So there is this thing called What to Expect.

Oh, there you go.

I don't know if you— yeah, that's kind of like a— it's a book. It has its own app, and when we had our first one, we downloaded that. And every week baby grows in a certain shape, and, you know, it grows its legs, body, everything, eyes and all that.

Yeah.

And they compare it to like a fruit or a vegetable, or like, you know, visually say that it's this big, it's this big. And, you know, and they have this video which is like probably 30 seconds or so visual of your— and we get an email, of course, with saying that, hey, you know, these are the things that you need to look after. There's the tips for mom. Yeah, you know, avoid this and all that. So I think—

My genius idea wasn't that genius because it's been done already. Okay,

back to the drawing

board.

Uh, back to the drawing board. Uh, Ryan, this has been a blast. Appreciate you for joining, sharing the tips, and, uh, Yeah, rooting for you. You know that we're a big fan of Workspaces. You know, I think I have to do like a version 2 because I just revamped the whole thing, added lights and all that, as you can see. Uh, but yeah, any closing thoughts before we wrap up?

No, I really appreciate the time. Um, huge fan of, of everything you've done. Like you said, I mean, we both worked at Product Hunt together. I think it's kind of cool how our kind of like career arcs have been very similar, honestly. Um,

Yeah.

In the last couple years. And I think it's just a lot of fun. I think everyone, like you said, should do some sort of side project. I don't care what your role is. That, you know, changed my life, got me outta supply chain, got me into working in tech. It got me, you know, just a creative outlet too that, you

know,

I needed. So yeah, do a side project. It could turn into something like Workspaces. And yeah, I think everyone should do that.

Awesome. Yeah. All right. You've gotten the memo, so just go ship it and then, you know, come back and say what you've done. Appreciate you guys for listening. Appreciate you, Ryan, for joining. That's a wrap, folks. Stay tuned for some more awesome conversations. Cheers. Cheers.