<img alt="" src="https://secure.data-insight365.com/265687.png" style="display:none;">
What are your SaaS company's current growth marketing challenges and wins?

February 13, 2024

Creating A Viral Product Growth Loop, Expanding Into Sales-Led From PLG, And Learning How To Not "Eat The Marshmallow" As A Remote Leader With Curtis Duggan of Lemon Squeezy And Remotely Serious

Curtis Duggan, who leads partnerships at Lemon Squeezy and hosts the Remotely Serious podcast, joins Jeanna on this episode of Remotely Cultured.

Curtis and Jeanna discuss how Lemon Squeezy nailed product-led growth, how they gained organic traction with users on X, and why they're moving into sales-led growth. Curtis also shares his thoughts on all things remote work, including how to delay the gratification of getting things done when working with a distributed team and why a flat hierarchy works for remote-first startups.
 
 
 
 
Resources Mentioned In This Episode:

Transcript:

Jeanna: Hey everyone, welcome to Remotely Cultured. I'm your host, Jeanna, calling in from Roatan, Honduras, where I run FPS and host this podcast. This episode is brought to you by First Page Strategy. At FPS, we use data and big ideas to produce exponential growth for product-led brands who need to nail their acquisition goals and want to work with a flexible non-traditional agency. For example, in one year we've grown a client's total revenue, 197%. Their organic revenue by 300% and their paid revenue by over a thousand percent. If you're a SaaS, fintech or startup and need to hit your high growth acquisition goals, check us out at firstpagestrategy.com. Today on the podcast, we have with us.Curtis Duggan. Curtis works on partnerships and growth at Lemon Squeezy, a SaaS company that is an all-in-one platform for software companies to handle payment, subscriptions, tax, etc. And he's also the host of Remotely Serious, a podcast focused on remote work. So we are brothers and sisters in the remote podcast world and welcome Curtis. Let's tell the listeners where you're calling in from. 

Curtis: I'm calling in from Victoria, Canada. First of all, thanks for having me on the podcast. And Victoria is the capital city of British Columbia, a province in Western Canada, and it's on an island. So the island is called Vancouver Island. So if you just look at the United States and it's kind of like the continental United States up in the top left, exactly, there's a little island that dips down from the Canadian border. And I'm up there in the, up here in the Pacific Northwest.

Jeanna: Awesome. We already have so much in common. We live in the island life. We're talking about remote work. I'm a big island girl. Can you tell us a little bit for those who have not been to Victoria, what is the culture like in Victoria? Like what's unique to the area? What would tourists want to experience? 

Curtis: Well, it is not just by my own bias, but by a lot of commentators. I think Conde Nast just rated it the top most beautiful small city or medium sized city in the world. So it has a beautiful natural setting and lots of nature where the mountains meet the ocean. And there's all kinds of outdoorsy type of activities to do in a temperate rainforest. So for anyone who likes that, it's really good. And Victoria is really, it's a meeting of a long running First Nations or indigenous culture, but also kind of the, remnants of being an outpost of the British Commonwealth or a British colony. So even more than a lot of places in Canada, it feels very British downtown. There's a parliament building that looks like a British, you know, castle from the 1800s or something like that, and hotels and castles that look like that. So it has that British colonial feel, a lot of beautiful trees and natural setting, and a lot of focus on the Indigenous culture of the local First Nations people all melding together in our island setting. 

Jeanna: Lovely. I once, when I was about in sixth grade, I believe, took a ferry up there for a school class trip and we went to the parliament building and all of that. So I have a very distant memory of the beauty that you have some of your beautiful government buildings. What's it like working remote from Victoria? What's your guys' remote, what's your personal remote routine or where do you do your work from?

Curtis: My personal remote routine has been inside my apartment in kind of a miniature office since I moved back to Victoria. It's not necessarily that I, that's my total preference. I'm very happy to work from coworking spaces. I would say there's definitely a pre-pandemic and post-pandemic. So pre-pandemic, it did feel like it was more lively downtown with lots of people coming in to work at coworking spaces, work at traditional offices, have lunch, go to coffee shops. It feels like there's a little bit of a chill on that bustling amount of activity. And nowadays, I think more people just retreat to their apartments. That having been said, there are three or four or more very nice co-working spaces and lots of coffee shops. So you can find people frequenting those coffee shops. I do that too. I can walk out of my building and go three blocks and be in a great setting. But to be totally honest, it feels a bit quiet. It doesn't feel like the old days of just startup, open plan startup offices and bustling activity. Something hasn't recovered from COVID yet. 

Jeanna: Yeah, there's, I mean, this is a big conversation right now. There's like a shift away from downtown, right? A downtown of cities, something that I like growing up, I really experienced in my career before I went remote, you know, younger in my twenties and early thirties. You had, we had, I had this downtown culture. I always went into an office, I bus downtown and with the remote work and people not going downtown so much to work anymore, there's kind of a question mark now of like, what is the purpose of downtowns or like city centers, right? Which I think is so fascinating because we're definitely like in an era where all of that is changing. 

Curtis: Yeah, definitely. And we're not immune to that here. The downtown is at 60% of what it used to be or something like that for sure.

Jeanna: Right, right. Cool. All right. Well, we're going to talk a lot about remote work. Later in this podcast, I spent a majority of my work of our time kind of chatting about some topics there. But first, I want to touch a little bit on what you're up to in your day job. We said in when in your introduction that you're working on partnerships and growth at Lemon Squeezy. I'd love for you to just tell our listeners a little bit about what that role is and what you do on a daily basis. 

Curtis: Yeah, so Lemon squeezy is really going after a really important problem, which is kind of rolling out a modern payment stack for SaaS companies and creators and solopreneurs. If we think about some famous payments companies like Stripe, PayPal, they've been around for a long time and they've helped all kinds of people, millions of people make money on the internet. But in modern times, there's more going on. There's global sales tax, which didn't used to be a problem. You could sell things online, say, hey, it's 99 bucks. And there it is 99 bucks. I sold you something nowadays, the EU, the Canadian provinces, American States, and various countries around the world are saying, hey, you sold a bunch of digital software or eBooks or whatever you're selling in Germany, in Canada, in Quebec or whatever. And you owe sales tax on that. So there's a kind of a slightly boring problem that not, I'm sure most entrepreneurs don't want to think too much about that is needed when you're selling things online. And then there's all kinds of things around rolling out affiliate programs and kind of putting the basic layer of payments into context of like all the tools that someone needs. And so Lemon Squeezy every few months for the last couple of years, every few months they've rolled out a new feature, a new kind of addition to the payment stack. And so it's really exciting to be working with Lemon Squeezy on partnerships and growth. Maybe I joined, I would say November, I guess almost a year ago from when we're doing this recording. And what actually happened to kind of kick off and catalyze an amazing year of growth for Lemon Squeezy was an incident with a very familiar to many people competitor of Lemon Squeezy's, which is Gumroad. Gumroad helps people sell things online as well. And they had a certain fee structure. December and January, December of 2022 and January 2023, Gumroad went and doubled or tripled or even quadrupled their fees. They just decided we're gonna be more like the app store or we're gonna be more like Amazon and we're just gonna quadruple our fees or triple our fees. And so a bunch of people were looking for somewhere else besides Gumroad to go to, and this is all happening, I don't know, maybe within 30 days or 60 days of when I started with Lemon Squeezy. And so for a long while in the beginning of the year, my day-to-day was just managing hundreds of thousands, the caravans, they came, the pioneers, the people, the exodus of people from Gumroad online, of course, but just coming into the inbox, setting up stores was just a daily flood of hundreds of people. Just think about product market fit. It's a good problem to have. Yeah. I can see what it looks like. If I've ever experienced it before, I really, not as a founder, but as someone joining the team early, I saw how it was happening at Lemon Squeezy. A lot of my job was the intake and kind of just managing the growth of that. Now, you know, at Lemon Squeezy, we're looking towards the future. Lemon Squeezy has built a lot of features that support larger SaaS companies coming on board. They, Lemon Squeezy kind of came from a background of helping solo creators, but they're much, much more than that now. And so there's a long product roadmap. And so onboarding and finding new customers and then connecting the sales and marketing strategy with the product strategy is a big part of what I do. But in short, it's sales. That's what drives a lot of growth. And yeah, so it's kind of doing sales-led growth at a company that's already totally nailed product-led growth to a certain extent. And so it's helping expand into more channels for growth after this absolutely hit a grand slam on PLG.

Jeanna: Awesome. I love that. We have lots of listeners, leaders, other guests on the podcast that work at SaaS companies. And so I thought some of what you guys fall for is really fascinating. And I went to the website and read a little bit about Lemon Squeezy. But I read that you guys help SaaS companies grow their revenue from subscriptions, which is obviously like very important to SaaS companies. So can you talk a little bit about how you guys do that? 

Curtis: Yeah, so I think there's a few layers there. And the most obvious one is just helping people with a payments technology that can roll out a subscription, which might seem kind of obvious, like, oh, I guess don't you just set the payment to charge every month? And I guess, yep, that is at the nucleus layer. That's what it is, is making sure that you can set up a payment that can charge every month. But on top of that, there's all kinds of things around fraud prevention, having, you know, so many SaaS companies are now finding people that want to, you know, dispute a subscription, do a charge back to the bank, provide a fake credit card. And so there's a bunch of proprietary technology as well as third party technology working under the hood. So that basically entrepreneurs don't have to think about a lot of the headaches of getting, Oh, I had 50 charge backs and someone just scanned me out of five grand. Now I need to go and deal with all of that. We deal with all of that. Similarly, of course, the sales tax, that's something that we're handling for everyone. And so we really just wanna make it so that if you wanna roll out any kind of subscription with any kind of logic, you wanna prorate it, you wanna do it annual, monthly, have a one-time payment upfront that rolls over into a subscription, that all of that logic is something where you never have to touch a line of code or even touch a line of no code because you can just turn on subscriptions. And so we focus on that a lot because I think there is a, there is a history with Lemon Squeezy of helping people sell one-off products, like download this course or this PDF or these theme files. And we do that, but we've really put a lot of work into automating and making very, very easy peasy Lemon Squeezy the subscription process for SaaS companies where they're focused on the recurring stuff just as much as creators are focused on maybe selling something one off. 

Jeanna: Love it. Another thing I saw you guys support is, um, SaaS companies that want to create an affiliate platform and run an affiliate marketing program. So what does that look like from your guys's like end? What are you doing to facilitate that?

Curtis: Yeah, I think a lot of the power is in the ease of implementation and just aggregating affiliates. So if you think about affiliate programs, that's where you're having someone who is a content creator, a blogger, someone who writes epic tweet threads, someone who has a YouTube channel. A lot of people are not necessarily delivering a product themselves. They're just building an audience and then promoting products that they believe in and want to. So, and that there, that it is the, the world of affiliate marketing that's been around for decades. And even now in the year 2023 or in soon to be 2024, it's still not easy to kind of connect up an affiliate program, set up the logic, make sure the contractor, like the, the tax forms are done properly and then kind of give out the payments. It's something you can connect up with a third party program. But what we have now, is kind of a combination of the mechanics of an affiliate program, but also the network effects of essentially where when someone signs up to be an affiliate, they're signing up to Lemon Squeezy as a whole. So, we have thousands of affiliates signing up to get approved and have KYC and due diligence done by Lemon Squeezy. Then they're kind of like, hey, I'm a Lemon Squeezy approved affiliate. The next step is they can go and choose from the thousands of merchants which products, which Lemon Squeezy products they want to promote and then just really just within a portal, just say, I'd like to promote this. Here's who I am. Lemon squeezy has already vetted me. Would you like to turn me on? You know, flip the switch as an affiliate and get, and I'll get my link and off I go. And literally onboarding new affiliates for the merchants is as easy as just quickly reading an application and flipping a switch. And then that affiliate can go and do everything they need to do. And the, you know, the, the logic of, okay, they get a 20% commission and they need to get paid out. It's all handled by Lemon Squeezy's payout system. So you can just flip a switch and turn on an affiliate system. TLDR, no, flip one switch, boom, you got affiliates. 

Jeanna: That's great, I love it. And you talked a little bit, you mentioned just a bit ago that Lemon Squeezy's PLG, focused on product-led growth, but now they're moving into sales-led growth. Can you talk a little bit about that transition or what Lemon Squeezy has focused on in the past with PLG and now where they're going forward with sales? 

Curtis: Yeah, I think if anybody's been a creator or a solopreneur or a SaaS company on Twitter or X in the last few years, you may have seen the kind of revenue screenshots or I made my first Lemon Squeezy sale. And so the viral loop of someone joining Lemon Squeezy, getting a screenshot, setting up their first product and then saying like, even if they're not necessarily trying to promote Lemon Squeezy, they're kind of thinking about themselves. They'll share a screenshot that says I made a sale and then there's the Lemon Squeezy logo and it's a really, you know, we have a great design, so it looks really nice. And so, uh, without really too much, um, uh, you know, needing to spend a lot of money, the Twitter community and now the X community has helped us, has helped Lemon Squeezy grow. Um, just by kind of putting, I wouldn't call it a viral product loop. It's not necessarily like you share a link to Lemon Squeezy, but there is, there is some aspect of that. And so it's just, it's a bit of PLG. It's a, it's a bit of really amazing branding and put those together. And you have a Twitter community. That's really just helped Lemon Squeezy grow really, really well. Um, but of course, you know, being popular on Twitter and being popular with people who tweet, you know, what payments stack should I use? And then someone else tweets I use Lemon Squeezy, you should go use it. That's great, but that isn't exactly a formal sales process. And so there are other things that can be done. Not every buyer is choosing a payment stack because it was popular on Twitter. The CFOs and the decision makers at larger SaaS companies might have a slightly different process and they're maybe used to being sold to and marketed to a different way. And so without revealing too much of the secrets of the strategy for the next year, I can say, you know, focusing on that is, is something that's a complimentary to the amazing, visible, very visible public product-led growth that's happening on Twitter and in other places. 

Jeanna: Love it. Um, and so I'm, I'm assuming, obviously, but tell me a little bit about what is like remote first culture at Lemon Squeezy. Are you guys 100% remote? Like are you, where are you distributed? Like, let's talk a little bit about that. 

Curtis: Yeah, it is a hundred percent remote. And it was after being a founder and CEO myself, almost exclusively for 10 years, this is one of the most recent times where I kind of came in and a lot of the culture was already there without me creating it as the founder. So I was joining something that the founders, JR, Gilbert and Orman had already created. And it was indeed a hundred percent remote to my knowledge from the day one and from the day I joined. And so we have a team of people, a growing team of people. I don't think it would be an exaggeration to say, you know, for every person, there might be a different country. There's maybe a bit of a focus on UK and the United States in terms of the team, but you know, I'm Canadian. I'm not from the UK or the US. There's some UK people. Some of them might be UK citizens, but they're located in other countries. So we have people in Bali and Hungary and Scotland. And there is no hybrid and it's all remote. And yeah, the water cooler is Slack. And so we use that as well as other tools as well. And yeah, I've seen some iterations and evolutions of the culture, but even the companies that I ran, we still had maybe a city we considered the head office, and I almost think at Lemon Squeezy it's pretty fully distributed. 

Jeanna: Nice. What is unique to your guys' remote first culture? How do you, operations or culture-wise, what do you think is something you haven't seen before? 

Curtis: I think that it's astonishing and amazing how much I've seen what you might think is a type of growth that requires VC money, requires a dictator like deep hierarchy that flows down from a dictatorial CEO and it's a competitive space. And yet what I've seen is an amazing somewhat flat hierarchy where many people can own certain things and many people can sort of very quickly metaphorically swivel their chair and jump over to own something without a lot of middle management and kind of getting approvals going up the chain and down the chain. So, you know, that can take the form of async communication. It can take the form of all hands meetings and sort of caucuses getting together to solve a problem, but not necessarily, you know, a lot of information that is siloed and at the top and kind of only marketing knows about this and only engineering knows about this. I would say that the flat hierarchy allows for a lot of information sharing and it allows for a lot of speed where hierarchy is not getting in the way. And so maybe that's obvious to people. Of course you don't want hierarchy get in the way, but that's not like even a lot of remote companies I find still implement that kind of hierarchy. And I see an asset of Lemon Squeezy's culture being how flat it is. And of course it's growing. It's doing really well. So it will grow, it will double, it will triple in size. And we'll have to see how the founders want to handle that. But for now it's really worked well and the, and kind of the growth path bears out that it's working well. 

Jeanna: Nice. Okay. So we recently have our client of ours is Expensify and they, I'm talking about the same thing on the podcast, cause they also follow a very interesting, unique kind of flat culture where there's a lot of autonomy and they do meetings and everybody's invited and stuff like that. So I'm curious, like what is, what are some specific, like if another company wanted to move away from hierarchy and move more to a flat culture, like what do you guys specifically do to change that way of working and make things flat? 

Curtis: Well, I think that it's impossible to, um, it's impossible to maintain a deeply synchronized culture, I'm using that word to mean kind of the opposite of async. But I think that if you're used to having meetings where, you know, the decisions are made and then they're kind of communicated in a memo, there's definitely some memo writing and there's definitely some documentation and we use tools like Heights and, and Slack and in Google Docs and various pieces of software. People on different time zones and kind of this cycle of being able to document something well, get feedback, post things for feedback. I think everyone who works at a company or works in a culture like this should get good. There's almost really nitty gritty stuff around getting good at threads and Slack and kind of understanding that you need to parse what's happened since you were sleeping. This is maybe something that is not totally normal in a same time zone sync company in an async multi-time zone company. You need to kind of keep track of if you're being accountable, like I have these six threads. I responded to this. Oh, no one, no one responded to me on this. That's okay. They're busy, but I'm going to bump it and kind of just internalized by osmosis, just how to work with that. So I know it sounds really basic, but internalizing and an explicit, like, here's how we handle threads in Slack or whatever communication you use. These are the norms is a really important thing. And then also just acknowledging that people are on different time zones. And so you need to be a bit flexible there and also not, um, not structure your day where if you're a, let's say you're a high, high ambition executor, you like to get things done. You're going to have to understand that if the person that needs to get it done is on a different time zone, you can't sort of structure your day around. Like if I need to get something done, I'll just huddle everyone into a room figure it out at the last minute as we need to. Because I think a lot of really good managers, people with decades of experience, they're kind of used to being a quarterback or a military leader on the battlefield where the soldiers are right in front of them and saying like, if I need to motivate people, I'll just like, we'll take a 15 minutes. We need to chat something out. We'll do it right now before the afternoon's over. And you need to have delayed gratification. I can't eat the marshmallow every hour of like a huddle. I need to, I can't eat the marshmallow. The marshmallow is not available until tomorrow, which is like syncing with your teammate. So you figure out how to delay gratification and say, okay, I've documented this. I've given it to the right person. I've added the right person. Now they're gonna find it when they get to it. And then I'll have to get the response tomorrow and go on, move on to something else without, which is very, sounds easy. It almost sounds a little bit like nicer, like there's less intensity, but it actually is hard. It is hard to get them out mentality. If you're like, if you're used to being like, I'm not leaving the office at five o'clock till this darn thing is solved. I'll stay till seven with my teammates and we'll order pizza. Like that doesn't work. You can't do that. You gotta wait for the other person. It might be tomorrow. And you gotta adjust accordingly and doc and write and document well, what you need and why you're asking for it. 

Jeanna: Yeah. This is a lot of the ways that we work at FPS too. And I just really see people struggle to learn how to work like this. And we're constantly talking as a leadership team about how do we figure out how to hire people? Like if people can understand the tech tools, if they can communicate effectively. So what do you think it takes to like figure out if people can work like this? Because this is a very unique way of working, right? And I feel like not every company is working like this and there are a ton of nuances in how you should be communicating back and when and what you should be doing. You can't just live in your own bubble and disappear and not tell anybody where you're up to kind of a thing. And so in terms of just remote like remote work best practices, like what does it take to find employees that can figure this out? Or do you teach people about this or how does it look like?

Curtis: I do think that at its core, you want to start upstream from the problem as much as possible or upstream from this opportunity as much as possible. So number one, the CEO has to embrace it. It'll never work if it's happening kind of against the CEO's wishes while they're skeptical. They don't really believe in it, but they're just trying it. You might as well just have that CEO say, we're in the office or we're hybrid and kind of just, you know amicably part from anybody that wants to be remote. And I don't think there's a lot of doing it in spite of the CEO. So number one is like getting the CEO to not rubber stamp it, but kind of just communicate their vision for it if it's what's to be done. And then, again, number two, maybe a cliche answer, but don't hire people that embrace it. And I think there are ways to test that. I think one is, you this was done in offices even before remote work, which was kind of like a test period or a probationary period or an experiment where it's like, yeah, like we'll pay you. You know, you work for two weeks on a trial period and it's remote and we're gonna see how you work. And we're gonna teach you a little bit of our remote work philosophy. You're gonna just see how it happens by working for two weeks or even for a full month. And then we'll learn about each other. So I think...If, if companies don't do probationary periods and they're kind of used to doing all the work, a lot of work free hire just through like grueling rounds and rounds and rounds of interviews, you may want to like cancel a couple of those interviews or like, you know, roll them back 50% and get someone to an on the, an actual remote probationary internship faster. Just because it's hard to interview for remote work endlessly.

Jeanna: Yeah, it is.

Curtis: And that used to be, you know, what in-office companies did is, you know, like, we'll, we'll interview them so much that we'll just know them inside out and if they fit our culture. I don't know if that works quite as well. And then third, I think that documenting some processes is good. And I think it's, it's really just about like, it's almost like a rhythm and timing thing like in any relationship, it's getting people used to, and I don't, so I don't think there's a right answer here. Some companies might say, we want a TikTok daily. Like we want you to kind of, we're not looking over your shoulder, but we want you to kind of like check in at the end of your day. Whenever that might be, it might be in Bali, Indonesia, it might be in Chicago, but like check in at the end of your day. You might have a TikTok rhythm that is a little bit more like we're checking in once a week. And then you might have a TikTok rhythm for some, someone who's probably not every month, but you know, maybe someone's deep coding something and, even with coding, I think you want to ship more often than once a month. Um, but I think it's establishing the rhythm. I can't say what the right rhythm is for every company. Um, but it's like, it's really being explicit about that. And the hard part is like talking about things you wouldn't normally talk about. Like if I, if someone says this on Slack, the expectation is responses come in 12 hours, or if it's a different company culture, like, hey, if it comes on Slack, we do want a response within an hour. Like this isn't know, we're running a business here. And I think just being really explicit about that and not having people assume that, oh, you'll just get it. You'll just like get it. Some of those things that are, it's almost annoyingly awkward to be so precise about what the culture is, but it's helpful to do because then people can learn the rules of the game. And then hopefully most hires will work, but some, whether it's the company, not working out, it's the company saying this doesn't work or the team member saying this doesn't work, they might part ways and say like, I don't like this. I, I don't want to be on my own so much. I don't let, you know, for whatever reason, but I think those are the three things like CEO, um, tweak the hiring and then over communicate almost annoyingly the tactics of how we do things remotely.

Jeanna: I think that's really important because these tools that a lot of the companies that are working remote stack, like Asana, ClickUp, Notion, whatever the tool set is, it's a little bit of the wild, wild west. If you don't like explicitly say how you need to be working within these things and how to use them. And so this goes, and you said this word earlier, and I'd love to just hear your opinion, but you said the word hybrid. And for me, I find this idea of hybrid to be really difficult, right? When there's so many things that go into doing a remote first company, right? Being very explicit about documentation and how you're using these tools and blah, blah. I feel like hybrid is kind of one foot in, one foot out and not really focused on building like a great remote first company. So love to hear your thoughts. Like what are your thoughts on this hybrid movement? Do you believe in this in-between middle ground can be good for companies or what are your thoughts?

Curtis: I think most of the time it doesn't work and it's bad. So I don't think that three days a week. So you're kind of on a leash, you know, you can get a little far. You can take a four day weekend, but you know, you're, you're basically an office worker, like hybrid where it's just like, but you have casual Monday and casual Friday. That's almost like still having an office job. It's just like a slightly more comfortable commute and it's only three days. So I don't think, I think companies that want people to be within a 40 miles of the office such that they could come in three days a week. I think maybe just give them Friday afternoon off and just lean into the fact that you're an in-office company. I don't think... I think if you're doing that, four and a half days is better than three. Bring everybody into the office if they're actually living in the same town and then maybe it's like you need to come in for half the day or whatever. I think that that's one way that people talk about hybrid. Another way that people talk about hybrid, because I don't know if what your definition is, but I've seen different definitions. And sometimes it's more like, well, we have some people that are remote and some people that are in the office. And I have some kind of maybe specific opinions on this, which is that I'd be a hypocrite if I said, I think everybody should come into the office because I wouldn't want to, I would want to have the ability to be remote internationally, fully remote. Um, but I do think there are situations where sustained in-person time does work. So I think co-founders starting a company, tt may be superior for the three of you to get together for three to six months and be coming in every day and just getting from no revenue to some revenue together. Doesn't mean that co-founders can't start things totally remote. And I'm sure there's thousands of examples where that's happened. That might be one idea where it's like, let's go hybrid. I think another thing where hybrid might work is sales teams. So I can see why engineers and designers and digital marketers might want to be fully remote all the time. I think there's something around like kicking off a sales team in a region for the first time ever where the work is very, it's almost like a different psychology. It's like getting a sports team ready to go out onto the field and, and conquer in the way that, you know, motivating an engineering team to fix bugs and push a new feature. There is some red blooded passion there, but it's a little different than sales. And I think that there are some undeniable, getting a sales leader into the room with their sales team, there's something undeniable about that. So hybrid there where it's like, you need to be in here on Monday, then go off and take sales calls and drive around the Northeast or drive around Texas or fly around to whatever your region is to sell or get on Zoom and be virtual at home in order to sell. I think there's like, a benefit to hybrid for sales. And then also finally, maybe the last example is like, if you're about to sell the company or do a deal, the deal team or like the executives getting together in person to go through something really, really hard, like a due diligence phase of entertaining and acquisition, there's probably a benefit to not just hybrid, but even in person. But to be clear, I think just general hybrid for everyone in all cases. I don't like it and I don't think it works to be like, we're gonna have the worst of both worlds. Like you can't really be remote, but you're also not really building the in-office culture. I don't think it's good in most cases.

Jeanna: Yeah. And what I find so frustrating about it is this idea that to be remote just means that you're gonna let someone go home. So those companies are like keeping the processes, the operations, the culture that they had 15 years ago in an office. And now they're saying, oh, we're hybrid. We're just gonna let you go home, which is so much more to working remote than just leaving the office and going home, right? And still working in email and like still sitting on Zoom for eight hours a day. Like, so that's my problem with it is that it's just like, they're like, okay, we work remote too. We let people go home. So it's like, no, if you're not working at the top to change your internal processes and how you guys are working and how you're communicating and how you're holding meetings or not holding meetings and you're not actually truly working in a remote first fashion, right? So that was my, that's my intent.

Curtis: Yeah, I totally agree. Yeah, it's not just a, it's not a day home from school. It's not a snow day. It's not a perpetual snow day. It's a totally different way of working. Just like someone who didn't use email in 1988 and then said, we're gonna switch typewriters and secretaries to email. It's not just like, you know, okay, we'll have the secretary type the email. It's like, no, there's no more secretary. You're not doing that anymore. You're writing the email. Like you have to actually change something fundamental.

Jeanna: Well, Curtis, you have been working remote for a really long time. You are a digital nomad sometimes traveling and working. Yes. You have your own podcast talking about remote work. Let's talk a little bit about that, like your background of your love for digital nomadism and traveling and working and starting your podcast. Tell us a little bit about that evolution.

Curtis: Yeah, I think that's actually that's a good segue almost. It fits chronologically right after the story I just told. So I work for Virgin Pulse until the summer of 2020. And then as often happens with entrepreneurs, you don't necessarily stay for years and years. After you sell your company, there might be a logical time to leave. And I found that it was, my work was done after about six months and there wasn't much more I could do that was about like connecting the old company to the new company. And so I had already begun, like even working at Virgin Pulse, I had already begun this kind of nomadic journey that I thought would be short, but ended up being long. So for example, in May, I, I was a Canadian with the U S visa. So I was trying to, first of all, just trying to figure out like, what am I now? Like, am I going back to Canada? It's a weird time. It was a weird time to be leaving a company with a visa, but also like the prime minister of Canada is saying like the border might be closed. And so like my first step was like, okay, if this thing's dangerous, I'm just going to go to Arizona by the pool and at least find a comfortable Airbnb to wait 30 days in isolation and maybe put on a mask to go to Walmart, but I'll just wait for this thing to pass. And the pandemic didn't pass in 30 days, but it gave me that feeling of like, hey, I just like went somewhere. This isn't where my teammates are. This isn't where the office is. I have no even family connection to this place. It was just somewhere that was like, somewhere to hide from what's going on. And it was okay. It was fine. So I had seen remote work through the CEO lens. Yeah, we have remote employees in all these countries. But as the CEO, I thought of myself as needing to be wherever the action was. And so that month was the first time where I'm like, you could also be a leader or sort of work on something without even traveling to where the action is. It does work to be remote. And that kicked off a year or two of living in different places. So I've been to Croatia and Costa Rica and Vancouver in my home province in Canada. I'm trying to think where else, you know, I spent some time in London, not all in 2020 when you couldn't travel as much, but moving into 2021 and then especially in 2022 as things opened up more. I spent probably 18 months with no apartment, no or house. I did not have a fixed address per se and I would from Airbnb to Airbnb. And it worked. Like it got me interested in this new phase of life, which is with the one I'm still in, which is that I work remote. I don't necessarily think of myself as having like, I need to stay somewhere for 10 years. I'm in my thirties, but I haven't bought a house and don't feel the need to, although I might do it at some point for other reasons. It's not a mark of success for me to purchase a house and say, look at me. I did that. So yeah, I learned a lot of things and it also kind of kicked off something I never thought I would do because I had spent so much time in the VC backed world or just I had internalized startups is something where you start an idea and then you need to grow it. So you go raise money and you, you know, you just focus on it. You dedicate your whole life to it. And then, you know, with the case of Blue Mesa, I had a little win where it actually worked out after a few, maybe that didn't. So I was thinking, well, I must just figure out the next thing to do on this front. And I tried a few different projects that were kind of focused on that. And maybe made a few detours and mistakes around, like, I just need to immediately find my next VC back business. But in the background, what I was doing is like one day, I think it was Christmas eve or Christmas day, I just started blogging about remote work and I started reading a little bit more about solopreneurs and people that start niche sites and all this kind of stuff that I never, I never cared about when I was doing VC back businesses, it was always like, it has to be a hundred million dollar company or bust. And then I was like, oh, someone runs this blog and makes 5k a month or someone has this podcast and got an advertiser. And I was like, I guess I could try that. Like that actually sounds kind of interesting and it's something I've never done. And so I started a site called wavyator.com where I just started blogging. It has since been folded into a brand for a website, a newsletter and a podcast, which is remotely serious. And I've just gone on this journey of like stuff I never did before because I had a different kind of company. And now I'm like looking up, you know, Google search console, learn, you know, have learned SEO, how to run ads, how to, what microphone to buy, the one I'm talking to you in right now, how to chop up audio and edit audio and all kinds of like creator stuff. And I, by no means am I create, like I don't, we're starting to do some video, but I'm not like a YouTuber that knows, that gets on the YouTube every day on the YouTube content treadmill. But I'm starting to learn some of that stuff. And it's been really, I do have like the main work that I do at Lemon Squeezy, but with the side hustle, both financially and, what's the other word? Both financially and for personal reasons, growing this kind of brand around remote work has been quite rewarding and something that I'll, I see it as something that I'll do for decades to come. I'll always be working on this and it may become the main thing, but it may not. And, but it does grow every month. It grows a little bit.

Jeanna: Beautiful. And what is then one of your favorite topics that you've covered on your podcast about remote work?

Curtis: Well, I think there's lots of great topics around travel and destinations, like hearing about different places like Costa Rica and Croatia and Lisbon and Madeira. But I think what's interesting, and maybe it's something you're familiar with based on where I heard you were calling in from, but I really do feel like the creation of these new charter cities or economic zones like Prospera in Honduras, like what Safety Wing is gonna build years from now, it's just kind of an idea now, with Plumia and with... I wish there were more examples, but those are actually probably the two big ones. I think that's going to be really interesting because right now, I think we talk about remote work and it's like, oh yeah, you know, Lisbon's nice and, oh, make sure to go to Costa Rica in the dry season, not the wet season, or it's kind of just like vacation tips a little bit. I mean, it's remote work, but what I think is really interesting and what will happen is when remote work allows for like possibly new forms of governance, new, new communities, new ways of people organizing each other. And it doesn't look like it right now to the average person walking down the street. Everything kind of, they wouldn't know about this, but it'll be interesting by 2030 if it's very normal to kind of jump in and kind of go to an economic zone or a city that's truly new. And maybe it's partnering with a host country, but some of these places that are rethinking how we interact economically from scratch. Um, that, that feels like scratching it's something that will be huge in 2030. And I like hearing about that, even if a lot of the talk about remote work is like, what software do you use and what places are nice to go that that's great. But there's, there's bigger societal trends, like kind of. Below the surface of the iceberg. 

Jeanna: Yep. Yeah. Um, man, I mean, we have no time to get into Prospera. Maybe we do a follow up at some point. It is a very interesting concept for those who haven't heard it. Google Prospera and it's doing exactly what Curtis is saying is like building its own kind of non-government place to form their own way of living and the Honduran government has agreed to let them move forward in their own the government control from Honduran government. So it's fascinating, right? It's not really like, alive right now. It's kind of just a little bit quiet and defunct. So we'll see if it goes somewhere in the future. It's down the road from my house about 20 minutes. So we'll see what happens. But cool. All right. Well, let's go through our final questions. Curtis, thanks for being on the podcast. You're just a wealth of information from being a founder to working in the SaaS industry, working on PLG to remote work and traveling and spend fun to have you a little bit longer than when we normally go. But I have three final questions. The one is what is your one work from hashtag work from anywhere item or tool that you can never live without?

Curtis: Well, this might be a cheat answer. I will say the 15 inch MacBook Air M2 that just came out, I feel like it's the greatest laptop that's ever made. And I'm not saying that because I love Apple or, I do love Apple, but I've had MacBooks that I don't like and the fan goes and there's lots of MacBooks I don't like. And this one I do and I think it feels like the ultimate laptop machine. So I'd recommend it to anyone that's like, I'm gonna...I'm used to my desktop, I'm used to my three monitors. What laptop should I bring? I would say that. Maybe that's a cheat answer. So the second thing I would say, if I can cheat and say two things, if I can only say one thing, the Logitech Brio 4K webcam and the Rode microphone that I have in front of me, I find that if I can set that up, I have like a big arm on my desktop that you wouldn't need to take with you. You could just put it on your desk. But if you do anything around, I wouldn't even say podcasts, if you just even have meetings with people, I think there's just something that like, upgrades your psychology if you do the webcam. And I'm saying this to someone that like, I was a CEO when I would just pull up my laptop and not think about like cinematography for a long time. But in the last year or two, I think the Logitech Brio 4K webcam and this Rota PodMic that I use, it just gets me into a different psychology when I'm on a zoom call and I felt like I got headaches from zoom calls to like for many years when I wasn't set up like this, I would just get staring at a laptop would be, it would just get me down. And I feel like I can go for a long time with this setup. So I, if you can fit it in your backpack or your briefcase bag or whatever, um, the right webcam and the right mic, uh, to throw on your laptop or on your monitor can go a long way if you are ever on calls throughout the day.

Jeanna: Love it. All right. Well, we have a Amazon list for our podcast because we have so many people talking about various books or various products. So we'll link those in there. What do you think is a great remote work productivity hack to tell people?

Curtis: Great remote work productivity hack. I would say that Making sure that your to do lists aren't just lists but time blocks so even if the time block is do 10 small things, by the end of this time block, I like to move things from lists. I used to have the system of like, there's 30 things on the list, that's my to-do list. And then, I'd get through 14 of them. And I guess the day is over. Should I just stay up till two in the morning and do the rest? And I found that just never having something that's a to-do without any kind of time block attached to it, it's better to have time blocks that and I've come around to this religion after resisting it for a very long time. And I'm like, I don't want no, I don't want time blocks. I don't want to be free to just yeah, play jazz all day. And it's like, no, I want time blocks now. But that's my team time block.

Jeanna: Yeah. Okay, cool. If someone wanted to learn more about you, where should they go online?

Curtis: Yeah, you can go on X slash Twitter, Curtis Duggan or Remotely Serious. That's probably a good place to start. We've got accounts on Instagram, but, uh, I would say the best place to start is Twitter or remotelyserious.com.

Jeanna: Cool. remotelyserious.com. Okay. Great. Thanks for coming on Remotely Cultured today. It was a pleasure having you.

Curtis: Yes. Yeah. Thank you for having me. And it's been a pleasure.

Latest Episodes

Creating A Viral Product Growth Loop, Expanding Into Sales-Led From PLG, And Learning How To Not

Creating A Viral Product Growth Loop, Expanding Into Sales-Led From PLG, And Learning How To Not "Eat The Marshmallow" As A Remote Leader With Curtis Duggan of Lemon Squeezy And Remotely Serious

Curtis Duggan, who leads partnerships at Lemon Squeezy and hosts the Remotely Serious podcast, joins Jeanna on this episode of Remotely Cul...

February 13, 2024

The Art of Creating Incredible In-Person Retreats for Your Remote Company With Matt Young of Nomadic6

The Art of Creating Incredible In-Person Retreats for Your Remote Company With Matt Young of Nomadic6

In this episode of Remotely Cultured, Jeanna chats with Matt Young, CEO of Nomadic6, about the art of creating in-person retreats for remot...

December 19, 2023

How SaaS Companies Can Effectively Create (And Document!) Processes, Fun Ways To Hold Your Leadership Team Accountable, and a Game-Changing Hiring Tips With Suzie Cyrenne of Buster Fetcher

How SaaS Companies Can Effectively Create (And Document!) Processes, Fun Ways To Hold Your Leadership Team Accountable, and a Game-Changing Hiring Tips With Suzie Cyrenne of Buster Fetcher

In this episode, Jeanna welcomes Suzie Cyrenne, Co-founder and COO of Buster Fetcher and Zumalka, to discuss remote work culture and proces...

December 05, 2023