The Bootstrapped Founder

Arvid Kahl 0:00
Today, I'm talking to Asia Orangio, about early stage marketing, sending surveys and dealing with growth challenges for indie hackers. Asia is the CEO of DemandMaven and she helps founders go to market and grow their businesses. You'll hear strategies and tactics from someone who's done 1000s of customer interviews and can help you figure out what's really going to drive your growth. Today's episode is sponsored by acquire.com. More on that later. Now, here is Asia.

Hey, Asia and welcome to the show. Your expertise lies in helping companies go to market and a lot of founders are pretty convinced they know what that looks like what they should be doing. Can you share a memorable experience where finding this strategy, this approach dramatically changed a company's trajectory?

Asia Orangio 0:45
Oh, my gosh! Oh, man, how many stories can I tell in a short amount of time? Absolutely. Okay. So just for context, though, the work that I do, I work with early stage companies. I work with growth stage companies. And I've also worked with like, half a billion dollar companies like huge. And at this stage, absolutely. I've worked with founders where they had it in their minds that they were going to build this product. And they were like, these are all the features that's going to be in it. And this is going to be who it's for, we do a customer discovery project together and then their whole minds completely shift and completely change of like, oh, my God! The person I wanted to sell to is not going to buy what I was going to build. It actually needs to be this. I've been in those situations where I've worked with founders who didn't even have a product yet. They had a concept. And they needed to validate it, or at least get a certain level of confidence because you never can 100% validate anything, but get closer. And then I've also I've worked with founders who have had products. They've gone to market. Maybe they got 10 customers, but it was like pulling teeth to get those 10. And they're feeling like something's missing, something's wrong and I can't figure out what it is. Is it the market? Is it us? Is it our positioning? And we do like a qualitative research project or qualitative insights project or go to market project or whatever. And then they walk away with, oh, it was my messaging this whole time or oh, it was, I was targeting the wrong people. We actually, so I was working with a company just recently. They're in the Gantt chart space, which there's a bajillion tools in the Gantt chart space, productivity, in general, there's a ton. But Gantt charts, surprisingly, there's a lot also and worked with a founder on a couple of different projects, did a growth audit, and also looked at monetization. And one of the things that we discovered was he had all of these industries that were buying the product. And then what we found was actually, the construction industry loved Gantt charts, apparently. They paid more, they had better price sensitivity, like everything about them was just like, way better. And it was just so funny to hear the founder go like, I didn't realize one that that was the vertical that loved this the most and also that they would pay more and also that they did not care about half of the features on our roadmap. So now he's like going through like an existential crisis of like, do I build this roadmap? Or do I not?

Arvid Kahl 3:20
Yeah, who did they build it fo in the first place? Like, did they have a completely different industry in mind?

Asia Orangio 3:25
Well, it wasn't as much industry as much as it was, you know, a lot of early stage, especially bootstrap founders, they have the features that they're just really excited about. And they're really close and dear to their heart. And they're like, I want to build more widgets or I want to go and build more of this or I want to go build that integration because whatever we're like, I like Kubernetes. I'm gonna go do something with that. And so then what ends up happening is, you know, it becomes a passion project, but it doesn't always translate to revenue. And being a bootstrap founder, you've got to balance both. Being a maker, you've got to balance both like what scratches the itch, but then also like, what helps you make money and it'd be best if you know, if both were aligned. But really what it was, was the founder had a roadmap full of enhancements that he perceived as valuable. But when we did our monetization project, one of the things that came out of it was, we do what's called a value preference analysis. It's a survey. But when we did the survey and then we analyze the results, what he realized was, all the stuff that he was prioritizing people didn't actually care about. They actually cared about all these other things. And it was harder and it took more effort and it wasn't as fun to him to build but it was gonna make him more money. So he was like, oh, man, I have to like totally change my roadmap now and I was like, that's product management. But, you know, it's the trade, right?

Arvid Kahl 4:52
That's so interesting because, like from my own founder perspective, I think I would have trouble coming up even with the contents of a survey that was not bias by what I already think is important. Like how do you skip around that? Like, how do you get the outside perspective for a founder like that?

Asia Orangio 5:07
This is so so, so common and anyone who's listening out there and cringing, you are not alone. Everyone doesn't even me. And I'm not even the like the builder. Okay, so usually and this is gonna sound so high level, but I'll try to give you like real examples as much as I possibly can without divulging, you know, like, who this is about, but usually when it comes to surveys for the purpose of product management or surveys for the purpose of growth or marketing or what have you. The natural tendency is to think like, okay, like, what are all the questions that I want to ask? And like, what are all the answers that I want to get? And that is where you got to stop. Like, you're like, what am I want to hear? And that's like, the total not right way to approach it. And this is really hard to do. And if you don't do a whole lot of research, like my whole life is quantitative insight and quantity like, yeah, quantitative analysis. It's qual and quant all the time every day, that's where I live. And with qualitative, you really have to pause and you have to ask yourself, not what do I want to hear? And not even really, what do I want to ask customers? Because that comes after the very first question, which is, what progress am I hoping to make? If you can, before you even jump to the what questions am I gonna ask? If you just stop and say, what progress am I trying to make? Well, I really don't know what I should be charging. I would like to makea progress in knowing what I should charge or I'm not really confident in my product roadmap. I would really like to know what features I should build. Okay, that's great. But then the next step is, you're not then going to ask that question. You're not going to write what features should I build? In your survey, you are then going to use a few different tools, one of which I can actually tell folks about. I use it all the time. It's called maxDiff. MaxDiff is, it's a type of survey question that you can ask that's way better than the like, you know, rank feature one on a scale of one to five with most or least too interesting to you, rank feature number two on a scale of one to five, it's way better than that. Actually, what it is, is instead of asking people to rank things on a scale, what you do is you give them some list of attributes, categories. It could be features, it could be anything you can imagine, like, some category of things that you want people to prioritize and you say, out of this list, what's the most important to you and what's the least important to you? And then you calculate, tally all of that up. And what you end up with if feature number one, maybe 20 people said it was most important to them, but then two people said it was least important. So great, that has a score of 20. So you subtract the most important, least important, but you do that across all of your features. And this is exactly what happened to this founder. But he discovered all the stuff that he was like hoping to build, nobody really wanted. They all wanted all the harder stuff. But then when it gets really cool is if you ask in the same survey, qualifying questions around like, who are you? Or like, what's your role? Or what's your title, industry, whatever. You can actually segment that data. And then you can discover, oh, these people want these things. And these people want these things, or, you know, whatever. But that's the beginning of it. But most people, when they design surveys, they jump into what do I want to hear? And what questions do I want to ask? But we, I always recommend, like, you have to take a step back. And you have to ask yourself from a business perspective, what progress are you trying to make? Because that's what's going to determine how you approach a survey. If you launch in with well, what do I want to know, that's still very intuitive, don't get me wrong, like and you should totally do it if you know that you need information. I don't ever want to deter a founder from not sending a survey because we're not going to do it right. You should do it. Do it anyway, do it bad, get the information that you're going to need, you know, like, just do it. But you're gonna get to a place where you're gonna want to do it better, hopefully or you're going to hire someone like me to do it better. But ideally, like it's the okay, what do we actually want to accomplish with the survey? Because if we're going to send out a survey, max you're going to ask like 10 to 15 questions, you're gonna get so many responses. We need to maximize the potential of what this is going to do. Because, you know, depending on how many customers you have, you might be overwhelmed and flooded with answers, but you also might not and so you kind of want to maximize the opportunity that you have to conduct the survey.

Arvid Kahl 9:39
Right. You were just mentioning like, qualitative quantitative. So in a survey like this, that sounds very quantitative to me, people rank, you have the MaxDiff, you get like older rank numbers. Do you also ask for like qualitative questions like what else should I put in there? Or the main question is mostly like, does it deter people from actually like filling out the survey if you make them think or do you just want their intuitive response?

Asia Orangio 10:03
Sometimes. So we try to balance, we try to lean and err more on the side of asking more like quantitative style questions so things that people can select or click. But to be fair, though, if you have conducted a lot of qualitative research, then filling out answers, like kind of like pre selecting answers for a survey actually becomes a lot easier because you already know generally speaking, like, okay, like, if I asked this question, I should expect to hear like this range of answers. If you've never run a survey before ever in your life on your customer base and maybe you don't know your customers as well, then having predetermined answers might give you skews that you might not know, cuz you're not gonna know what you don't know. But then also, you might not be able to totally trust. So if you're running a survey for the very first time, you've never done one before. And maybe like, you haven't talked as much to customers like in this way, not just about features, but about like, you know, that you haven't had as many conversations, I'll say. Then having a few more open ended questions could actually be a really good way just to get a sense for like, what would people say as your first pass, but then usually moving forward like, the more surveys you do, the more that you want to kind of keep it like you keep the open ended stuff to a minimum, if you can. But to be honest, there's no hard and fast rule. I've seen it all. There's no hard and fast rule. But what I will say though, is again, it goes back to like, what are your goals? And also, what context do you have? Because if you don't have as much context, then doing more open ended stuff could totally work. It's not gonna be very rich, but it will give you like hearing from the customer in the limited time and space that they have to answer you. But then at the same exact time, though, we've run surveys for clients before and some people came back with, like essays, like and you're just like, whoa, it's like you did an interview almost, just depends. But I will say that the less context you have, maybe the more open ended questions can help. Otherwise, if you have a lot of context then you can kind of guess like maybe what the answers could be. And then, you know, you throw it out there and see how customers respond or users or whatever.

Arvid Kahl 12:18
This sounds like, it's nice in some situations when you have like a blue ocean kind of situation. But if you've know exactly where you want to go, like, if you've overcome your inhibition to know where you're gonna go and you want to know where you're gonna go, then maybe more quantitative methods work. That's interesting. You can probably tell that I'm asking all these detailed questions, probably mostly for my own sake at this point because I have a struggle sending surveys. I don't know what it is in me. I just don't want to bother people with a survey. I know it's a self imposed limitation. And maybe you can help me out of this because I know it's important for me. I just started a new business. I'm building a voice messaging tool for podcasts because I love podcasts. And I love podcasts where people send messages like Seth Godin's Akimbo, right? You have people sending in messages, that kind of stuff. I always love this. But the tooling looks like it's from the 90s. And function wise also isn't like in the year 2024. Yeah. So I'm, again, software engineer feature think, right? I'm building this, but I want to know more about my prospects and about my future customers. But I don't want to send emails, like how can I overcome this inhibition to bother people with something that could be quite useful to them?

Asia Orangio 13:30
Yeah, I love this. Okay, this is interesting. So I will say we really only do surveys when we have a larger volume of customers. So if you have 100 plus customers, surveys are going to be your jam. The same is true, actually, for website surveys. So you can do website surveys as well. And if you're getting, let's say, 510 k visits a month, like you probably have enough traffic to do like a website survey. But if you don't have 100 customers, I would say, interviews. Interviews are going to be your best friend. I have actually completely changed my perspective on interviews in the last I'll say six months to a year. I used to be very hardcore, don't pay people you know, 45 minutes to an hour. And because I've been testing this. And also I've been working a lot with Bob Molesta. He's like a co-architect of jobs to be done blah, blah. Incredible guy. But talking a lot and like working pub, I've learned the incentive doesn't actually matter as much. So all that to say what I mean by that is I think you can get over the hump by a couple of things. You're absolutely correct. It is totally a self imposed limitation. And a lot of founders have this. It's one of the most common ones actually, even I have this. I have this about myself and my own business. Like I really should be drinking my own champagne way more than I am and interviewing more founders, but even I have the self imposed like I don't want to bother them. But what I can say from running 1000s of customer interviews for the people who you want to create value for, it's never too much to ask. And also, most people are delighted. They would love to talk to the CEO of, you know, a new upcoming small business. And you know, help them shape exactly what they want because selfishly, they want you to build what they want. So I think that there's the mindset part of it. But then the outreach, the outreach is, you know, I think it's either an email or LinkedIn message depending on the context of you know, who you're talking to, maybe depending on your industry. It's actually a phone call or text. There are some industries that are like that. But the good news is that you don't need hundreds of interviews. You really just need about 10 to 15. And honestly, the first three to four are going to be eye opening. And once you, I actually worked with a founder, who he was at the 8 to 10k mark MRR. And he had never done research before. And he was in a similar space. He was like, I'm afraid. I'm terrified. I don't want to bother them. He had like 30,000 users and maybe like 500 paying customers. And it was interesting because after the first two, he was like, okay, this is less scary. And I ran them with him. So he actually ran the interview himself. I was with him. I was like coaching him to the process. But by the fourth one, he was like, this is awesome. I can't believe I waited too long to like to do this. Because he was like, I've had so many ideas. I got like, we should go build this, blah, blah, blah. And I was like, yeah, this is why we do this. It was great. So I will say the first two, three, they're gonna be weird especially if you're not used to it. But by the time you get to like the fourth and the fifth, you're gonna be like, oh, my gosh, this was awesome. Like, I can't believe I waited so long to do this. And if you're feeling really, really introverted, never forget that you can do this with someone else. Like there are other people who can maybe run the interview for you. And like you just like tag along. So there's also that as an option. But yeah, I think to make it also feel a little bit easier, you can offer an incentive. So some people offer like a $50 gift card or $100 gift card, something to sweeten the pot. So you don't feel like you're like really, you know, putting them out. But I guarantee you, the people that you're building for, they are going to like assuming that you are out to create value. Most people are going to be pretty open to chatting with you especially if you are building something that is in their best interest.

Arvid Kahl 17:35
Yeah, you would want that to be the case for most products being built, right? That's a win win. There's a business going coming out of it. But also, it's producing massive value for the people using it. That brings me to something that you just said, like you said, 30,000 people that have used the product, 500 paying customers, who do you listen to when you reach out to them? Because those 30,000 might become or 29,500? Right? They might become paying customers, but they're not yet. So do you ask them questions? Or do you ask questions of your already existing customer base?

Asia Orangio 18:08
So this is kind of where we get into the it depends territory. And the reason why it depends is because it depends on what is the progress we're trying to make? What is the outcome we're trying to achieve with whatever the research is? Traditionally speaking when it comes to go to market, we need to pay more attention to people who are paying because people who pay money have made a real trade off. If they never pay any money, they make no sacrifice. They make no trade off. And it's not that you can't trust people who have never made a sacrifice or a trade off. It's just if they've never made the trade off of paying money, then everything is a hypothetical. You don't actually know. And it's just like you said like they could become but they haven't. So what we try to do in those scenarios is, traditionally speaking, the paying customer usually takes priority. However, there are plenty of use cases to do what we call audience research people who aren't paying you money, but they fit the general profile or they could. So what we do in those scenarios is we try to find people who may not have made a trade off to buy your product. But maybe they've made similar trade offs. So maybe they might not have bought HubSpot, but they bought Salesforce. So like if you can find people who have made the trade off, even if it wasn't for your product, if it was for something similar, that's an excellent space to play in. Where you don't want to plan is you don't really want to play in the sandbox of they've never made a trade off even close to it. It's not on their radar, they're totally unaware. They might have tried the product but they can't like they don't have like a perspective like for where to fit you in. And that's kind of where you want to be careful because it's really easy to get lost in the sauce with that. But if you can talk to people who have made similar trade offs, so maybe they tried your product but they went to a competitor or they've used or bought stuff like what you're providing in the past. Those are great people to talk to because it'll give you a sense for like, what direction do you need to go in? Or do you want to go in? But I would say paying customers definitely take precedence. Those are like,paying customers are worth their weight in gold because they've actually made a real trade off. They've made an exchange and people who make exchanges and also people who make exchanges and in churn, those are the people that you really want to talk to for sure.

Arvid Kahl 20:28
Yeah, it's certainly the presence of a budget signal something that, you know, the absence of a budget doesn't. So that makes a lot of sense. Thank you for sharing this. So what's your position on freemium then as a business model itself?

Asia Orangio 20:42
Freemium I would say, so I've worked with plenty of early stage and bootstrapped companies. And I would say so I've been running DemandMaven now for almost for actually, for six years, February will be six years. I've been running DemandMaven, which is thank you!

Arvid Kahl 20:56
Wow!

Asia Orangio 20:57
The first three to four, I would say we've exclusively focused on early stage of bootstrap companies. And freemium, I've got to say, is one of the toughest models to make work for bootstrap companies. I'm not against it. But I do think that you have to have just an absolutely massive, total addressable market that has a willingness to pay. And also, you as the founder, you have to have an incredible onboarding and activation experience, let alone go to market, go to market, you know, people product channel. People product model channel. Yeah. And market itself. Like, yeah, that aside, great. But product itself, when people sign up, get the value moment become a customer, if that is not dialed in, freemium is so tough. And then on top of that, freemium is not a revenue model. It's an acquisition model. It does make acquisition easier, but I'm going to put that in finger quotes because while it makes it easier, it puts a lot more pressure on having an incredible product experience. And I've not seen as many scenarios where bootstrap founders are like, equipped enough to be able to manage that well. You're gonna need more product people, more developers. It creates and maybe that's you, maybe like, you just like working all the time. But from what I've seen, there's very specific scenarios where it works extremely well. But a lot of the times, they actually need to be a self serve free trial. And maybe it's opt out, you know, it could be an opt out credit card scenario. But that's really, I think, where most bootstrappers play and I don't think freemium is going to work for everyone, to be honest. I know Patrick Campbell. I don't know if he would disagree or agree, actually. But I know that in the past, he has been like freemium's great. Everyone should get freemium. But I think it requires a lot of energy, capital. Actually, I think it requires more effort.

Arvid Kahl 22:54
Yeah. And for Patrick in particular, right? You had ProfitWell, the free product and everything was wonderful, but the high ticket stuff was on the other side for price intelligently, right? They was compensated like it's not that ProfitWell needed to make money. It was compensated by massive consulting fees on the other side, so I wouldn't even call this a freemium. It's just like, an anchor product, like a lead magnet, really. So I think he's an outlier in that regard compared to all the other SaaS founders that I see because and I think I needed to hear this just now. And a lot of people needed to hear this too. Because freemium is easy. It's easy to look at the number of users going up and thinking you have a case for revenue, even though the conversion, the onboarding and the stickiness, right? The retention of them is the hard part. So thanks for sharing that. Makes me rethink my pricing strategy, right. But I guess that's what it is, right? It's all the experimentation. You all need to figure out, like, where to go, where to start how to, like, move on over time. We were just talking about niching into categories, particularly with the product category that you brought up, right? Do people in your product category have an alternative that they already use? It's already budget being spent in the category you're in. You gave a talk MicroConf about this whole niche versus like, well, niche versus what is not a niche kind of conversation. I would like to dive into this a little bit. Because in the indie hacker space, more and more, we're being told and we are telling as people in the space niching is where it's at. You niche down, you find that thing and you find that place, and you start there and maybe you grow out of it or you just stick with it and you build a presence in that field. Is that still a valid approach or is picking a niche the same thing as focusing on something? I'd like to ask you.

Asia Orangio 24:41
I'm so glad you mentioned this. Okay. Yes. Awesome. Good call back. That's one of my favorite talks actually. Okay, so yeah, you're gonna hear this all the time, niche down niche down. Okay, so there's focusing and then there's niching down. I'm gonna start with niching down and I give this example every time and it's based off of a company but I'm not gonna remember off the top of my head. But every time he's always like, I love that you keep using my company as an example. I think he likes it. Okay, so niching is like, let's say we're in the software category of CRM, customer relationship management, very popular, tons of software out there that's like this. Niching would be un-CRM for trucking companies. And niching is basically says, if you're a trucking company and you need CRM, you should use our product. You are centering around a particular industry or vertical. And if an agency came to you, you'd be like I mean, listen, like, we're not going to tell you not to use our software, but we're for trucking companies, go away. And like, okay, you know and if a SaaS company comes to you, listen, we're CRM for trucking companies, go away. And that works for some people and for some founders. I think I don't think it is. I'm not gonna say it's bad advice. I think it's incomplete advice. I think there's many ways to go to market. Niching is one of them. And I think part of why so context for why I think you hear this a lot is I think it makes a very complex problem very easy. Because go to market is complex. There's a lot of variables and a lot going on. Niching makes it feel very easy. And I also think, too, at the same exact time, though, like, if you don't plan on raising a bunch of funding, if you don't plan on like building like this whole big thing, you want to keep it lean, niching could make a lot of sense for you like, just like personally. There's this other approach, though, that I think is much more realistic and also gives founders much more freedom to explore business models that are more in alignment with them. Because niching like if you don't like, so is your CRM for trucking companies, but like, if you don't like trucking companies that like, you might run that business for two years and then be like, I'm out. So there's this other concept. And this is the concept that most businesses use. But it's one that I think a lot of bootstrap founders and early stage founders. It's not, I don't think it's as common to think about, but it's definitely common for more established companies. And it's called focusing and what focusing says is, okay, sure, CRM for trucking companies, maybe that's where we start. But maybe we build for trucking companies for one to two years. And then we expand later into construction. Because trucking is cool, but like construction is where it's at. I don't know, I'm making this up. And then maybe in another one to two years, maybe we expand again, into manufacturing and then maybe in another one. So focusing basically says, the features, the content, the marketing, the channels, all the go to market strategy, putting the finger quotes, it's all going to focus on either that one vertical or industry or it could also be software category because there are some that will focus like in various software categories over time. The best example of this in real life that I can give is ConvertKit. So when Nathan Barry first started the company, he was like, email marketing is our software category. And we're going to focus on I think it was specifically bloggers, food bloggers. Is it food bloggers? I should know the story of my heart because I've studied them so much. But when he first started, I want to do email marketing for food bloggers. And then he expanded over time. And then I think after like one to two years, he was like, okay,we are now going to expand into the audience of I don't remember what it was something else like small business, like websites that are like lifestyle blogs or whatever. And then every like one to two years, he would continue to expand. He didn't niche forever because you imagine if ConvertKit was like, what email marketing for bloggers forever. And then it would never become the what billion dollar company that is. They actually don't know if it's that big. But it would never if you could imagine like that. Now, here's the thing, though, because what's really cool about being a founder is like you get to decide, like you get to decide what your chaos is. And I could imagine a scenario where if Nathan were just a different person, he could be like, yeah, I'm gonna stop here. And that will be okay for him. You know, like, I'm not gonna shame anyone for not doing that. Or, you know, doing what they're doing. But I think you know, Nathan was like, I want to do more. So he expanded but he did it by what we call focusing and it's just okay, I understand this audience, go to market wise now. I am now going to expand and shift my focus on another audience still gonna cater to the old audience, but now I'm gonna expand it with new audience and that's how he built his business.

Arvid Kahl 29:49
So how do you prevent yourself from falling prey to the shiny object syndrome? There's another interesting audience out there. How do you prevent overextending at that point?

Asia Orangio 29:58
Yeah. This is tough because as entrepreneurs, we love a shiny object. I love a shiny object. I'm like, public defender number one on this. Okay, so I actually go back to the story of, you know, the trough of despair of like, we all go through the same cycle. There's the like, oh, we're so excited and we're super optimistic. It's gonna go great. And then it's like, there's like a little bit of like, oh, no, this sucks. And then you're in the trough of despair. You're like, this is terrible. I was reading this study, this report. And whenever we get attracted to the shiny object, what happens is whatever track we're currently on, we're hitting the trough of despair. And the shiny object gives us that optimism again because we start the curve all over again. Oh, there's a new thing. Oh, let me really excited about it. Oh, my gosh, is really cool. Oh, no, this is way harder than I thought. Oh, my gosh, this kind of sucks. And so what ends up happening is, we as entrepreneurs are wired for that. We're wired that's why we're innovators. That's why we're, you know, breaking ceilings left and right. But what ends up happening is sometimes we don't stay in the trough of despair long enough with the current track that we're on. And so a shiny object comes along and it's tempting, ooh, you can have that feeling of optimism again if you just switch gears. And I think of that, actually and right when whatever I'm working on gets challenging, that's how I know I probably need to stick with it. Now, I do think, however, are there scenarios where like if a thing isn't working, stop doing the thing. I think at the same token, while we jump off of tracks very quickly, sometimes we can stay on them for way too long. And we're like, okay, you're beating this dead horse. And it's like, it's not, the dog will hunt as we say in the south. But I think part of the game is knowing when you need to switch tracks and knowing when you need to stay on. It's tough. And I'm not going to say I have a perfect answer even on this. But when it comes to go to market, at least what I can say is, if you've done your research, if you've done your exploration for a particular audience, if you've like putting the single quotes validated as much as you possibly can about expanding into a new market, then you can probably trust doing that expansion and also weighing its pros and cons and its trade offs. Assuming that you've done your research, you probably know what the challenges are going to be to an extent. You can probably predict, like what some of that's going to be. And I think really smart business owners choose audiences that are the easiest for them to enter into, like easiest for them to segue into. And when they make very big strategic bets of, okay, this one's gonna be really tough for us to do. But I think that we can do it. Knowing that and having that context ahead of time before you double down on it, is going to make that process easier. But when that research is not conducted, when you don't do your due diligence, when you're kind of just like, let's do trucking companies, why not? And they were like, oh my gosh, just kind of sucks. And like, it's really hard or whatever, then that's kind of where I would say, if like that's just a lesson, right? It's just a life lesson. But I think the more information that we can get ahead of time, it's never gonna be perfect. It's never gonna be complete. But if we can get more context ahead of time and that should help us make better decisions. And also, it also helps you decide to, yeah, like I'm ready to jump tracks. I'm ready to like, jump into the new thing. And you'll hopefully feel much more confident about it. And then when it gets challenging because it will, it absolutely will. It won't be a surprise and you'll be a little bit more better prepared for it.

Arvid Kahl 32:16
Yeah, that kind of confidence is the problem that I see a lot in founders. I talked to several founders who are at that stage, who want to go into different verticals, let's just call them that. But they're afraid of several things. I think one of the biggest things is now I have to do everything twice. I need to cater to my own audience and speak to them in their voice, the lingo they have, right? The kind of jargon that they use and this new audience, which might be completely distinct, but equally interesting. Now, I don't need to write blog posts for them and talk about their topics. Is that a thing? That can be done easier than just doubling all your efforts? Like, is there a way to keep the tone of voice consistent while going into new fields? What do you think about that?

Asia Orangio 34:28
Well, I think this is what's so interesting is that I'm assuming that you have done your due diligence for one audience. The thing is, is when you expand your go to market focus, I mean, yes, in theory with like a fully developed team and like you've got like a whole squad of people helping you with this. Yeah, in theory, like you'd have enough resources to cater to both. But I think as opposed to our founder, like if you don't have that many resources, your old cause like your existing customers and like the people that you're already attracting from that content from that material, assuming it's evergreen. And you don't have to keep producing it if it's generating the value and if it's generating customers. Maybe you need to update it like every six months to a year, depending on Google's rules and search and blah, blah, blah, like maybe like, depending on how you're acquiring the customers, like maybe you've got to update the campaigns, like every once in a while. But in theory, like if you've created the system, the acquisition system to acquire an audience, you probably don't need to put as much effort into it to keep it going, maybe like a little bit here and there. And I find, depending on I'm gonna say this depends, like, there are certain markets and industries where this is not the case. And if you're off, you're off and like you need to, like, get it back together. But I think I find if you create the system and it's consistently generating things and it's continuous, then you don't have to, it doesn't require as much effort to keep the wheel going and you can stretch into something else and it won't feel like a stretch. It'll just feel like you're just shifting focus. You'll need to remember, of course, every six months to a year to like, go back to that old thing and like, okay, like is anything I missed? But for the most part, it should be relatively easy to build a new system. And I'm gonna say it's easy, it's straightforward, it's relatively a little bit more predictable, especially again, if you've done your research, if you've explored that audience enough.

Arvid Kahl 36:32
I like the idea of having a process that you can slightly adjust, and then use the exact same process for a different audience. I think that that is a mental model that I can work with, right? Where it's okay, this serves these people, let's just tweak a couple of screws here and there. And then it can also serve these others. What it immediately brings to mind to me as a, I guess, self imposed solopreneur is that this will probably require more people to help me with because I am only an expert in a couple of fields. But if I want to go into a different industry, I need somebody who can from the start speak the language of these people. Do you think this is a requirement of that shift to get help from outside? Or can you kind of get there yourself? And it might just take a bit longer? What would you choose there?

Asia Orangio 37:10
Interesting. So my first thought was, you technically don't need to hire someone who already speaks that language. I would actually wager that most. So if you get marketing help, for example, depending on the type of marketing help, most marketers aren't going to be well versed in your industry at all. But they're going to learn by voice of customer, by qualitative research, by like talking to people and talking to customers and blah, blah, do like conducting their own insights and conducting their own research. That's how marketers kind of learn the language. But so my first thought was, I mean, technically, you don't necessarily need someone who comes from that world. If you hire someone good, that's relatively trainable/discoverable, like you can figure that out. But what I do think is even more interesting is the concept of expanding like your team, even if it's like a contractor or freelancer and you have like, this is absolutely possible. Like I've seen this a bajillion times where there's like a solo founder and he's got like a part time engineer who helps some of the product and then he's got like, two to three writers and social folks and like and they're part time and they're full time. And they, you know, they found their resources, like using fiverr or Upwork. Sometimes even like LinkedIn and you can totally build that very nimble team and things are very cyclical. The hardest part is going to be of course, the hiring. Who do you hire? How do you know if they're good? That's kind of that's where it gets hard. And that's where it gets tricky. But what I will say though, is it's another skill, it's a muscle. Once you, there's all kinds of guides you can read, but nothing beats the experience. So once you gain this experience, you'll learn over time what does experience look like? What does great look like versus not? I know you didn't ask this question, but I feel compelled to say it anyway. Because I do think it's really interesting. But Nathan Latka actually mentioned this at a SaaS Talk once. And he mentioned a process where the way that he finds talent is he puts out a job like on Fiverr. He hires five or six people to do the same job. And then he just sees like, what's the quality level and that gives him a gauge of okay, I can see like, what the quality level is. And then he just picks his favorite one. And then he just rinses, washes and repeats and it's fiverr. So there's gonna be a range of prices and that's how he does it. And he does that for everything, literally every job.

Arvid Kahl 39:44
That is awesome. You know what? I've seen is coming from a completely different field. I'm a hobby miniature painter. So I paint tiny figurines because that's just a hobby of mine that I've had since childhood. Yeah, exactly.

Asia Orangio 41:19
Yeah

Arvid Kahl 39:57
You should see the backside of this office because it's full of paints and brushes and stuff. But yeah, that's really that's what I do to unwind and just, you know, get into a space that is not completely occupied with just coding all the time. And in that community of YouTubers around that hobby, there are a lot of people who hire like 10 people on Fiverr or whatever, to paint their figurines for them. And then they create content out of this just checking the different levels of skill and the different price sets. So there is something to be said about, like finding somebody who's good by just setting them up against a couple other people and comparing. I think that's an interesting way of hiring. It kind of does reinforce kind of the global north south thing with the pricing. You know, the problem that people in the countries that have really, really low wages and you know, their purchasing power parity is extremely low. They do a lot of work for very little money, but it does make sense to try this out. Like, would you outsource all of these things? Like, is that something? My question really is like, how much does the founder need to be involved in this? That's really what it is because you were talking so much about customer interviews and all that in the beginning. And it's like, yeah, that's something I need to do to see the vision of this. But when it comes to creating content or marketing strategies, how much involvement does a solopreneur/small team leader, small CEO, really need to put in there?

Asia Orangio 41:19
Yeah, that's a great question. It's a tough one. Okay. So what I will say is, if you think about your time horizon of a year, if you did 10 very high quality customer interviews a year, you would be beating literally all of your competitors, every single one of them. I know that because I probably work with them. But if you think about, can you do 10 interviews in a year, that doesn't feel too bad, right? Especially if it's like the first couple of weeks of the year. But I would say if you just did that, which will require a lot of involvement from you because you're gonna have to source them, you're gonna have to reach out to them, you're gonna have to actually talk to the customer. But I guarantee that if you were to do that process, it would energize you for the next six months, at least. And in terms of like, how you would be thinking about like, okay, well, what marketing do I need to put out? What should my messaging be? That you're gonna get so much clarity just from doing that. The book I'm gonna recommend to everyone listening is the Mom Test. Rob Fitzpatrick makes interviewing very, very straightforward. I cannot think of a better resource for bootstrappers or indie hackers or anything like that, like it like truly the one of the best. But I guarantee that if you do that, when we think about the year time horizon, seems pretty small. The level of involvement, however, on an ongoing basis, does ultimately depend on how experienced your resources are. If you have budget to spend, I would highly recommend investing more in your resources. If you don't have as much budget to spend, keep in mind that the quality of the marketing or whatever it is that you're putting out there might not be as good, therefore, we'll require more of you. But the thing is, is that if you don't know what great looks like, then it is what it is like you're not going to notice anyway. But what I can say, though, is if like so let's say you're at the 45 or 40k MMR mark and you're at the place where like you can hire resources. But you're like you're torn. Like, do you need someone experienced, need someone not experienced? This is where I would say it's gonna very much depend on what is your comfort level? What trade offs are you willing to make? Because you can hire someone who's maybe less experienced, but much cheaper. But the trade off will be, they're gonna look to you for all the answers. If you don't like marketing, you're probably gonna have to answer a lot of marketing questions and it's gonna feel very uncomfortable. And otherwise, you're gonna have to figure out how to level them up. So can you afford courses? Can you afford training? I recommend reforged everyone, like literally everyone because it's so affordable, like compared like, based off of what you get. But that's kind of one of the trade offs and knowing that you're never probably like this person, unless they're just gonna really knock your socks off. They're probably not going to be your CMO because you're not paying cmo money, right? That's one of the hardest decisions to make. And I've got a couple of clients in this boat now. You know, they have an incredible marketing team. They love their marketing team. But they really need a VP of marketing, but they're just not quite at the place yet where it makes sense to afford that. So the trade off is okay, well, that's okay. Yeah, love your team. That's great. Let's get them some training. Let's get them some like advising. Let's get them some coaching. Like let's like if we can't afford a VP of Marketing, that's fine. There's other ways to level up your skill and to level up your team. The downside is, it will require more of you, assuming that you care. You might not and that's okay. Like I want to make sure anyone who's listening is not like feeling guilty about like, oh man, I really don't care about that, like, that's okay. I believe in like running your business how you want to run it like and if you want to improve it and if you want to get better at certain things great, like, that's where you can hire other people. You can hire resources. You can, you know, get consultants, whatever. But if you're like, I'm never gonna do that, Asia like, that's totally fine. I'm cool with it. I applaud it actually.

Arvid Kahl 45:28
What do you think of hiring like fractional people for those kind of roles? Like because they're expensive in the full role but in a fractional a couple days a week, what do you think of that?

Asia Orangio 45:39
I am biased because I have been fractional. I actually I helped a company go from 13K MRR to 2 million ARR. And they just exited. They just exited for a lot of money for so much money. It was really cool. And but I was fractional. I wasn't that expensive, either. It was, to be fair, they did have some marketing resources, but they didn't have a single full time marketing person until this year. And I've worked with this company for a very long time. And I mean, it's impressive, like they were extremely lean, very, very lean. So I think that there are scenarios where it works. And it makes sense. I think it's very, very contingent on, the ultimately the founder or the CEO. Because I think if the expectation is that this person is just going to take marketing off of your hands forever and you're never going to think about it, that's never the case. I can't think of a single scenario where as the founder, you never think about marketing unless you have a co founder who's the marketer. And then maybe you never, you actually just never think about marketing. But I think if the expectation is that this fractional person is just going to take it all off of your hands and you're never going to have to think about it. I don't think that that's realistic. The other thing too, is that it depends on the nature of just how fractional this person is. Are they doing execution? Are they not doing execution? Do they have budgeted resources to get the execution? So in my case, I wasn't doing it all. But I was able to hire writers. I was able to hire like freelancers to just come in and do some of the executions if needed. And then also the CEO himself did a lot of stuff. So I think if there's a very clear expectation for how are we going to divvy up the work, then I think it could work extremely well. And I think like, I mean, this company, like really made out super well, doesn't work for everyone, though. I think that there are scenarios where if there is budget and they need a full time person and like it's really obvious that they do it, then they just need to hire full time, like let's but I do think that there are some scenarios where fractional makes a lot of sense for maybe more executive leadership. I'm essentially like, a chief growth officer or CMO coming in and like, okay, here's what you gotta do. You gotta go and do all these things. And like, I can help you do some of it. But like, we need other people to also do it, can't be all of Asia, right? Those are scenarios that work really well. I know Amanda Natividad has an opinion on this. I thought was really, really, really interesting. And I'm not gonna remember exactly what she said about it. I remember seeing this on Twitter. And I remember agreeing with a lot of what she said. But there are scenarios though or fractional can make sense. There are a lot of scenarios, though, where it doesn't and I think like, I think if you can afford full time help that's experienced get it. But that comes down to like, how good are you at hiring? Demand me then. So my own business, it took us years to get good at hiring researchers. It took us years, took a lot of trial and error. But now that we know like, oh, this is what the process is. It's like it's so easy. Hopefully you don't have to go through that with marketing. That would suck. But I know for me because we mostly work with a lot of contractors and freelancers. So we do a lot of hiring like a few times a year. But hopefully that's not the case for you for marketing because that would not be fun. But I will say though it's a muscle.

Arvid Kahl 49:05
Oh for sure. Like like all things business, right? You get to experiment and figure out they're just the right way to lift the weight and then lifting it becomes much easier, right? Let's use that weird analogy here. But what I get from you, what I heard you just say was that fractional hires shouldn't be your first hires. That's really what I'm getting out of this, you should get makers and people who like will get their hands dirty and in the weeds, even though they might not be the most experienced ones and not the most expensive ones. But the first hire should not be a person that needs other people to help them do the work. That's what I'm getting out of this.

Asia Orangio 49:43
Totally. And I also think too, there's a lot of models that I've seen where maybe the team is very junior but there's like a fractional executive leader. That can work really well depending on how much management the team needs, that could work extremely well a lot of the times, but sometimes. So a fractional person and when I say fractional, like I'm assuming that they're like 10 to 15 hours a week, sometimes though, having an advisor. So there's a lot of companies that I advise. And I'm maybe it's like a couple of hours a week if that. And that can be extremely helpful because a good adviser, depending on like, what they're advising in, for me it's usually growth or marketing or both. I'm able to like cut through the traffic really quickly, like don't prioritize that project. That's gonna be a waste of your time do this instead. And then they're like, okay, great, great, great. Can you review our work? Yes. Like, yep, that's all good. No, change these things. Okay, go off. And then they go on to do the thing. And then they come back and they're like, okay, we've got more stuff. So if you can't, yeah, executive level fractional stuff, I wouldn't recommend that for super early stage. But advising could be extremely beneficial because I kind of like working with someone who's either been through it or work with a bunch of companies who have been through it. That could be awesome, for sure.

Arvid Kahl 51:02
Yeah, I do it for a couple of people more in the technical space, but like it's a call a month or something. And just like keep people in the loop, keep reshuffling priorities that may have like gone out of proportion or something. I think that's effectively mentorship on a level, right? Like for many founders, there's this mentorship aspect to it as well, where it's not just like advising on the business, but also in the personal development of the founder. That's kind of where I come in, like a little bit like intersectional there. But yeah, that sounds like a much smarter move than just hiring somebody who may really not be the right hire. Wow, thank you so much for sharing all of your insights and your personal experience here, too. That is incredibly valuable. Like, it's really nice to hear the distilled knowledge from all these projects. And all these, you know, these surveys, these conversations, 1000s of interviews, like when do you get to talk to a person that actually has all this insights? So thank you so much for sharing this. I bet everybody listening right now will be very interested in following you and learning more about you. So where would you like them to go to stay in touch with you?

Asia Orangio 52:06
Yeah, okay, there's a few places. I hang out the most these days, I still call it Twitter.

Arvid Kahl 52:13
Me, too. Me, too.

Asia Orangio 52:14
Cool, cool. There's also LinkedIn and then, you know, feel free to connect with me on LinkedIn. If you do just leave a message just like, hey, I heard you on the podcast. Otherwise, content wise. So I have a newsletter called The Work. And it is where I publish all about how to do the work like this really hard, muddy growth work that's like really confusing, same thing for go to market. And my whole thing is, how can I give you practical examples of doing a MaxDiff survey? How to interview customers about like, you know, potentially buying a product, like how do you do that? So my whole thing is, how do I give practical advice about the work that is required. So that can be found on demandmaven.substack.com. And The Work newsletter, I try to publish every week, but I actually got sick last month. So it has not been every week. But this year, I'm going to try to do I'm going to say at least 40 posts this year. So not the whole year, but at least 40. That's my goal.

Arvid Kahl 53:19
That's a spectacular goal. And if anybody needed any evidence that you're good at marketing, I think the last 60 seconds will convince them that you're really good at this. You're spectacular. Thank you so much for talking to me today and sharing all of that. It was really, really insightful. Thank you.

Asia Orangio 53:34
Thank you. It was a pleasure. Had a blast.

Arvid Kahl 53:36
I appreciate it.

And that's it for today. I will now briefly thank my sponsor, acquire.com. Imagine this, you're a founder who's built a really solid SaaS product, you acquired all those customers, and everything is generating really consistent monthly recurring revenue. That's the dream of every SaaS founder, right? The problem is, you're not growing for whatever reason, maybe it's lack of skill or lack of focus or play in lack of interest. You don't know. You just feel stuck in your business with your business. What should you do? Well, the story that I would like to hear is that you buckled down, you reignited the fire, and you started working on the business not just in the business, and all those things you did, like audience building and marketing and sales and outreach. They really helped you to go down this road, six months down the road, making all that money. You tripled your revenue and you have this hyper successful business. That is to dream. The reality unfortunately, is not as simple as this. And the situation that you might find yourself in is looking different for every single founder who's facing this crossroad. This problem is common, but it looks different every time. But what doesn't look different every time is the story that here just ends up being one of inaction and stagnation because the business becomes less and less valuable over time and then eventually completely worthless if you don't do anything. So if you find yourself here already at this point or you think your story is likely headed down a similar road, I would consider a third option and that is selling your business on acquire.com. Because you capitalizing on the value of your time today is a pretty smart move. It's certainly better than not doing anything. And acquire.com is free to list. They've helped hundreds of founders already. Just go check it out at try.acquire.com/arvid, it's me and see for yourself if this is the right option for you, your business at this time. You might just want to wait a bit and see if it works out half a year from now or a year from now. Just check it out. It's always good to be in the know.

Thank you for listening to the Bootstrapped Founder today. I really appreciate that. You can find me on Twitter @arvidkahl. And you'll find my books and my Twitter course there too. If you want to support me and the show, please subscribe to my YouTube channel, get the podcast in your podcast player of choice, whatever that might be. Do let me know. It'd be interesting to see and leave a rating and a review by going to (http://ratethispodcast.com/founder). It really makes a big difference if you show up there because then this podcast shows up in other people's feeds. And that's, I think, where we all would like it to be just helping other people learn and see and understand new things. Any of this will help the show. I really appreciate it. Thank you so much for listening. Have a wonderful day and bye bye.