Brennan Dunn has earned $20k/week as a freelancer, grown an agency to millions in revenue, started and sold a SaaS product, and makes over $100k/mo from his online courses. Learn how he thinks about business.
What's up, everyone. This is Courtland from indiehackers.com. Today I'm sitting down with Brennan Dunn, the founder of Double Your Freelancing. How's it going, Brennan?
I'm good, how are you, Courtland?
I'm doing excellent. Super excited to have you on the show. We got a chance to talk briefly at MicroConf a few weeks ago. Can you tell people who are listening a little bit about yourself and what it is that you do?
Yeah, so my main business in DoubleYourFreelancing.com, and it kind of happened by accident, which I guess we'll get into. But what I'm doing nowadays is I'm helping creative freelancers understand the business behind their business. So I'm helping them with pricing, with of getting clients, with pitching, and kind of all the stuff that people wish we didn't have to do but is kind of part of what comes with running your own independent freelancing business.
It's really interesting, because I think there's a ton of parallels between the types of things that freelancers maybe avoid doing naturally but that they need to do and that the founders of internet businesses also avoid doing that they maybe need to do. So you know, just a couple of examples, this comes from my history as a freelancer too, like I never wanted to reach out and find clients. You know, and then as an entrepreneur, I never wanted to reach out and find customers. Or just pricing, like as a freelancer I never really wanted to raise my rates, and I was scared people weren't gonna pay me the rates that I probably deserved. And as an entrepreneur, I always cut my prices way too low, and I could have easily doubled or tripled those things. I think a lot of the things that you're teaching people are super, just broad business skills that are useful for everybody. And I'm really excited to get into it.
I was just gonna say, most of the people in my audience actually, it's funny, like the majority of them are self-identified freelancers, but most do wanna end up selling products. And the interesting thing is that a lot of them, what they end up doing in their own consulting business, like setting up a sales pipeline and automating a lot of that, along with getting pricing right and everything else, directly translates into their product business. So it's kind of like, you know, all they're really going from is high-touch sales to low-touch sales, but for the most part all the other stuff maintains. So yeah, I mean, it's really, the parallels, it's not as different, I think, as a lot of people think. You know, it's just a different, you know, it's a different type of fulfillment, not software, it's manual, and otherwise it's high-touch sales, typically, versus you know, show up at the website, plug in the credit card, and go.
Exactly, there's just a lot of overlap between the two. Can you talk about your career as a freelancer? How did you get into freelancing? And do you still do freelancing right now?
Yeah, so I started back in 2006. I guess you could say I'd done freelancing without really knowing it. Earlier than that I was just kind of had day jobs, or when I was in college and always kind of did building websites and stuff on the side. But in 2006 it became a little more official. I went out on my own. And I started actually working with Bay area startups who needed help with their Ruby apps. So I was doing that remotely, and I had no idea what I was doing. I just became kind of like an augmented member of their team.
So I priced according to what the equivalent hourly rate of their in-house personnel were charging, or were getting paid I should say. And I did that for a while, and then in 2008, it got to the point where I had enough referral work that I could either turn away work or grow a team. I decided to grow a team, again, not knowing anything about managing a team or managing people or anything like that. And a few years later, we had gotten to 11 full-time employees. We were doing a few million a year in revenue. We had a brick-and-mortar office here in downtown Norfolk, Virginia. And it was by all accounts successful.
But the issue was, I had a lot of friends who were running these, you know, SaaS businesses. And I was building, effectively, web apps for my own clients, cause we were doing a lot of work for startups who needed us to build like their MVP and whatnot. And I wanted to do it myself. I wanted to have a lot of people paying me a little bit of money instead of a few clients paying me a lot of money. So I started an app called Planscope, and I realized it was really difficult to run an agency and a software company simultaneously. So I exited the agency to focus full time on Planscope. And so Planscope's the project venture now. It's a project management that I built for small agencies and freelancers, so people like me. And I, like a lot of new-time SaaS founders, I really struggled to sell it. I really struggled to get it in front of people.
So I had read about content marketing and I was reading up on that, and I started creating articles about freelancing that had nothing to do with project management but that helped the kind of target demographic. And that ended up doing really well. And I got people who showed up, read a lot of my content, but didn't care at all about the software. They just wanted the content. And eventually that led to me writing an ebook, which as an engineer, was really hard for me to do because I thought the ebooks were all BS. So I did that. It ended up working really well, and I wasn't getting slammed with refund requests. Instead people were saying, like, this is really good. And then I started getting testimonials, and people writing in who I'd never even talked to saying, you've literally changed my life. I don't know you, but here's what happened. And one thing led to another. I created additional courses and workshops.
Now that's my main business. And you know, we run two conferences a year, one in the US, one in Europe. We just crossed over 10,000 customers. And we've got an audience now of about 40,000 people. So it's doing really well. And last year, beginning of 2016, I once again realized it was really hard to run two companies. So I sold Planscope so I could focus on Double Your Freelancing. So Double Your Freelancing at first was a content marketing initiative for my SaaS. It ended up like exploding in success. So I then realized I wasn't able to build and support the SaaS the way I needed to, considering all that was needed of me on Double Your Freelancing side.
So are you full-time on Double Your Freelancing or do you do any consulting on the side of that?
No, I mean, I occasionally do just because I'm a big automation geek, so most of the business is now fully automated, so I do occasionally consult, but not much. And I've actually just started a new SaaS called RightMessage, which is my official entry back into the world of software. I'm trying to do a lot of what I've done manually on my own website, so I've done a lot with automatically changing the copy and the content of my website, depending on kind of like what you do or what state your business is in and what you want from me. I've been doing a lot of that but more manually. And a lot of people have written in saying, can you make this easy for me to do. So I'm basically, we're almost ready to ship the first version of this new SaaS that I've been working on for the last few months.
Cool, and just for some context, I know you're pretty transparent with revenue numbers. Can you talk about how successful Double Your Freelancing has been in terms of revenue and also Planscope?
Yeah, so DYF, I just ran the revenue report. Over the last year it did about 900,000. So it's pretty nice in the sense-
Yeah, I mean, it doesn't, it's cool because, you know, it just, it works, right? I mean, I'm able to, there's very minimal support. I've got a full-time assistant who handles a lot of the frontline support. But for the most part, I'm able to focus on kind of creating new content, upgrading my courses, and making them better, and everything else, but also getting to play with a lot of the fun things that I've been really geeking out on, like you know, automation and personalization and just really focused on how can I make it, again, my mission for the last year has been if I were to go into a coma, this should still work. So I've been doing a lot with doing things like observing behavior on my site, and then when they hit certain things or when they reach certain thresholds, to automatically pitch them on certain products of mine. And it's been steadily climbing over the last few months. And yeah, it looks like we're on track for probably at last one and a half million this year.
Yeah, that's huge, especially considering how small your team is. I mean, you're basically a team of just one person.
It's just me and then I've got, yeah, I've got a full-time assistant on retainer. And then I've got a few people who help me, but it's pretty much just me. Although we do have kind of like a daily coaching offering called The Expert Roundtable, which is where I've got consulting slash coaching friends of mine who are pretty authoritative in whatever niche they work in who make themselves available for a coaching call daily. And that's kind of our only other expense outside of my admin assistant and a few random freelancers who I hire on project basis.
It strikes me that you've done a lot of oscillating between freelancing and then a product business and then a product business and freelancing at the same time and then freelancing into teaching a course and then now back into a product business. Are there are any similarities and parallels that you've carried between all those disciplines that you've found are helpful across every one of them?
Yeah, I mean, I think, so a mistake I made with my agency was all of our business was transactional. So we didn't have any recurring revenue. With Planscope I got my first taste of kind of subscription revenue, and it was really nice. But it was really hard to grow. And the issue that I had and the thing I learned about growing Planscope was it was a habit-based app, meaning I had to get people to change their habits for it to work for them. So with project management software, especially mine, which is very, very opinionated about how you should work, it was really hard to get people to convert. And when we did get them to convert, because they're freelancers, there wasn't a direct correlation between signing up and getting some sort of ROI.
So you know, I learned a lot then, and I learned a lot about kind of the business of running a higher-scale software business. With consulting with an agency, you're very intimate with your clients, and you've got a lot of overhead, very little margins though typically. With software it was the opposite. So virtually no overhead but a lot of support. I had to get okay with the idea of like not bending over backwards for literally everyone who joined or who was a customer. Now with Double Your Freelancing, it's largely a transactional revenue business, so like the agency, it's typically one-off sales, but it's at very high volume, comparatively.
So again, I've learned from Planscope about high-volume, I learned from the agency about kind of how to do a lot of these one-off sales and how to build a proper business. I mean, really that was my first business. And now with DYF I'm learning how to predictably generate a lot of one-off sales. And now with the new SaaS, I'm taking all that collected knowledge and I'm working on how can I have a highly scalable business, finally, that has predictable monthly subscription revenue. So it's kind of like each business, even though they're very distinct, both in model and even audience, I've learned from each some core concept that I've applied to the subsequent business. And that's been, I mean, I'm very big on just experiment. Does it work? Yes, if yes, great, keep doing it. Otherwise, figure out why it didn't work and try something new. So yeah, I don't know if that answers your question, but that's been kind of like my, that's how they've all tied together in terms of how I've gotten to where I am now. But yeah, it's been quite the interesting ride.
Yeah, one of the things that I found interesting listening to several of the talks that you've given and going to Double Your Freelancing is how similar some of the lessons that you teach to aspiring freelancers and existing freelancers are to the lessons that people want to learn when they come to Indie Hackers. So a good example is just the importance of basic business knowledge, like sales and marketing, understanding why customers buy the thing that you're selling, and especially why businesses buy things, is almost exactly the same between freelancers and entrepreneurs. And it's funny because I think that we all go through life as consumers, without exception, right, we all buy things. And then the second we become creators, right, the second we are freelancers and we are selling ourselves and our skills, or are selling a business solution or the second we become entrepreneurs, and we're trying to sell a SaaS product or service to customers, it's like there's a switch where we're just suddenly unable to understand why consumers or businesses buy things.
So it's interesting to see, you know, the advice you give to freelancers about okay, here's how you should actually structure your marketing copy, right, here's how you pitch your skills and your offerings to businesses in order to get them to pay you the rate that you deserve rather than you know, doing the default thing that most people do that's just listing, you know, in the case of an entrepreneur, just listing their product's features, or in the case of a new freelancer, just listing, okay, here's the languages that I'm going to use, et cetera, and doing what you said you did earlier on, which is pricing yourself relative to that company's existing employees and just saying okay, you're paying for my time, and my time as a developer is worth X amount that you're paying your other developers. So I think it's just been really interesting to see some of those similarities.
I mean, I think one of the best things I learned when running the agency was when I finally realized that no one was paying us for code or design or you know, whatever it is we were doing. They were paying because they thought that by commissioning somebody to write this code that their business would be better, right? Like, that it would ultimately get some sort of return on investment. And I think a lot of us, myself included when I started, just thought that my job was to kind of swing the hammer for them. So they needed a Ruby developer, so I am here to write Ruby at this much an hour. And you know, a lot of the advice I give on pricing, it isn't about like just, you know, here are some like psychological tricks on how to convince people to pay you more. It's more than that. It's beyond that.
What I'm really trying to do is I'm trying to help people ultimately deliver a better product because the product is more aligned with the actual need that somebody has, right? So in the case of consulting, instead of just saying, oh, you need a website redesigned, I can reskin your website, try to actually figure out like why do they want their site redesigned, like why are they firing their current website, like what is it about the way things are that sucks so bad that they've seeked out somebody like you? And figure out exactly what is it they really need. Do they need to generate more leads? Are they look to get more sales? Like what is the objective they have, and then ultimately the purpose of the work you do, say the redesign, is with that end in mind. So the redesign will be better because you know exactly why they're wanting a redesign versus kind of the default thing that a lot of us do, which is, well let's talk about what it'll look like, let's talk about you know, how many pages we'll have, all these different kind of things that ultimately don't matter.
But what I've come to realize is for people like you know, us, we're engineers, it's more comfortable for us to talk tech, it's more comfortable for us to talk about the thing that we know best, the thing that we've studied for years and gotten really good at. It's a little harder to switch gears and talk about how what it is we do can benefit a business. But once we're able to do that, whether it's through like selling software or selling consulting, everything changes at that point cause you're able to then focus on, so for you know, the kind of consulting I do now, I mean, what it includes is me writing copy, setting up automation stuff for them, and doing some light front-end development. But in talking with my clients, none of that ever hits the surface. Like, I don't sell that. And you know, I'm not advertising myself as a copywriter slash developer slash can use Drip on your behalf kind of consultant.
Yeah, it took me a long time to really internalize the lesson that you're saying right now, which is that you need to actually understand what your customer is hiring you for. You need to understand what problems they want solved and how valuable those problems are and then end up pricing yourself relative to like the value that you're delivering versus other things. And I think to your point that we're developers, we're very comfortable around the skill set that we've developed and not comfortable around other things, I think that's true across almost every profession.
So my girlfriend for example does sex and relationship coaching. And she teaches other people how to do it, too. And they'll gain all these skills by taking her course, but at the end of the day, they still have to learn how to market and sell their skillset, right? It's not just about having that particular skillset. And it's the same with developers, it's the same with designers, et cetera.
So I think there's something to be said for teaching people how to market themselves, teaching people how to look at things from a customer's perspective and understand the value that they're delivering. And it's not, despite, you know, us buying and understanding why we buy things to a degree, it's not easy to be on the other side of the equation and actually figure out how to price ourselves.
Yeah, I was gonna say, I mean, not to go too much on a tangent, but if you really think about it, if somebody ends up hiring somebody like you or I, a few things have already happened. First off they've realized they have some issue that needs to be fixed. Second, they've realized that it can be fixed. And third, they've realized that it can be fixed by working with somebody like us. And you're putting a lot of like weight on that buyer to go through that entire process and eventually come to the realization that oh, I need to hire Brennan to do X, Y, and Z for me. And for everyone who could benefit from me, there are a few people who actually make it through that gauntlet. So you know, it's in our interest, I think, to, if they do get to the end of that gauntlet, if they do realize, okay, what we need is a web developer, you're already at that point commoditizing what it is you're selling.
And the same is true of like, when I was doing project management software. If I'm waiting for people to realize that they have a project management problem, I've already lost, in a way, right? Like I've already, you know, I'm missing out on so much. And at that point, they're looking and they're comparing feature set and they're comparing what it is it does, the technicals of the product in this case. And you know, the example I gave, like so for my new startup RightMessage, it's website personalization software. Well, how many people actually know that's possible relative to how many people could benefit from it? Very few. And that's why what we're doing from the beginning with our messaging and our marketing is to look at people who demographically fit with the kind of people who could benefit from our software and meeting them there and then preparing them to become customers of ours over time and systematically and automatically, and then by that time, now they're the ideal client of ours. They're an ideal customer of ours.
And you know, the same is true of consulting, its the same with products. I mean, the thing that we should be fighting against is backing ourselves into a commoditized corner. And the way to do that is to, again, the best way to do that that I've seen is to meet somebody where they are now and lead them and condition them, for lack of a better way of putting it, to be that perfect customer, that ideal customer who fully understands now, you're basically helping them. You know, I went to school for the classics, and we read a lot of Plato. And one of the things that Socrates got named as was a philosophical mid-wife. So his goal, like what he did was he helped people get to the philosophic awareness that he wanted them to get to through the right conversation, through the right teaching, through the right education. And you know, with products or services or whatever it is you're selling, the same can be true. The same should be true in that you're kind of that mid-wife bridging that gap from where they're right now to where they need to be in order to be a customer of yours.
It's interesting that you talk about avoiding commoditization by meeting the customer where they are. It's kind of like you're going higher up the funnel, right? So you're not targeting customers who already know exactly what solution they want and they're just picking from, you know, a handful of competitors. You're trying to get them before they've made that decision and then essentially educate them as to why what you're providing solves their problem. Is that accurate?
That's exactly it, yeah. Cause again, if you're being comparison shopped, at that point I think in a lot of times, you've pretty much already lost. I mean, that's when you need to then compete on pricing or on something like that. And again, you don't want to be in that position where the client has realized what it is they need and they just need a quote unquote vendor to give it to them.
So let's say, cause there's a bit of a trade off here. Let's say you're starting a company and you're in a very well-known segment and people already know exactly what solution that they're looking for. The thing that you have going for you in that situation is that people are already searching for you.
o in terms of getting in front of customers, there's probably already online forums that exist where people are gathered around that particular challenge and you can talk to them there. And there's probably popular keywords you can put in that actually have volume around them, blogs that are based around these topics versus the other end of the spectrum if you're going for something that people might not be searching for or that there isn't a clearly defined existing set of solutions for, then you have to be a little bit more creative, I think, in finding customers and educating them and letting them known exactly what it is that you're doing. How do you think about that problem? How do you think about finding people who have this, identifying customers, really in the first place, and then letting them know why what you're providing them helps them?
Yeah, so when I started scaling my agency, we quickly ran into the issue of having, now, a lot of overhead. Cause now we had employees, and these employees were pricey, and so on. So I had to find a way to systematically bring in the revenue we needed monthly to pay our bills.
The first thing I thought of, the thing that I really wanted to make work was the idea of kind of finding that perfect unicorn marketplace, which you see this again, if you look at like Hacker News. I mean, monthly there's somebody with their new freelancer marketplace they're coming out with cause we want this kind of perfect world where there's an exact alignment between need and offering, right? Where these ideal clients are just thinking like, I need somebody who does this, this, this, and this, and I'm willing to pay exactly what they're worth, and then they go to this mythical marketplace, and they find us, and the transaction just happens, and everyone's happy, right?
That would be great.
Yeah, that doesn't happen though. I mean, just look at people, all you need to do is go into like the subreddit for freelancing and type in Upwork and look at what comes up to see why that's not a good model. So to go back to my agency, in order to do this, we had to figure out a way, how can we get off kind of the luck bandwagon, cause you know, I mean most freelancers get clients through referrals, and these referrals come from past clients, so the issue with that though was we could only create so many clients in a certain window, right? Like we could only, we can't work with hundreds or thousands of clients a year. We can only handle a few. So if referrals come from past clients, we're limiting our referral pool, and what happens if I've got a $30,000 salary next month, but we don't get $30,000 in projects coming in? I mean, that's a big problem, right?
So one thing that we did, and again I just surrounded myself with people who were a lot smarter than I was to make this happen, we tried thinking about like why do these referrals happen? Why do people refer stuff? And ultimately it's because they got something of value from us. They've benefited from us in some way. So clients, you know, they benefited from us by getting, ideally, a solution to their problems, and now they're willing to refer us when the opportunity arises.
So we thought, well, what if we did something like, what if we just did, you know, they have all these groups, like Chamber of Commerces or you know, all these different kind of like meet-up groups, right, that meet up, I mean, out by you, you've got a ton of these, right? Like these monthly groups that meet up that are focused on some technology or entrepreneurs or something like that. So we basically did offline guest posts, where we would go to like the Chamber of Commerce and we'd say, hey, I see you have an education series that you're doing. We'd love to come in and talk about, really kind of like what do you do when you outgrow Excel? Because a lot of companies, they just use Excel to basically power everything. But they don't actually know that custom software is within reach and could really benefit them. So we were going after people who, by virtue of them being a member of this, they may or may not be a potential client of ours, but the fact that they were in this business community was all we needed.
So we went, we did these, you know we did our first presentation, we got like 80 people from that who ended up effectively opting in. And again, we didn't have the terminology, we had a stupid free MailChimp account. We didn't know what we were doing. But we got like 80 people from that first Chamber presentation we did, we were terrified to do, who wanted to hear more. And this ultimately set us off on doing a lot of these kinda like business seminars, which again were just offline webinars, if you think about it, right? I mean, that's what a seminar is, right? And we would do these, and there wouldn't be like a call to action of like buy now or anything like that, but what we would do is we would hook people up who went to these onto this really basic, stupid MailChimp drip that would ultimately lead to a hey, we'd love to hear what your next steps are. Here's Zach, who's the sales guy that worked for me, contact him, right? And we ended up getting a lot of inbound requests.
But the interesting thing was it wasn't the people who attended who would usually become clients of ours. Instead it would be, people who attended would get something of benefit, of value from us, and then refer us within their own network. So we ended up getting a lot of Fortune 500s as clients. We had no direct relationship to these companies, but there were people in our network who had benefited from us who then got us inside, you know, in the doors of these companies. We ended up working in 2012 with, Mitt Romney hired us. We had no direct connection at all to that guy. But somebody in our audience, and again, we didn't even know to call it an audience at that point, but we were able to kind of, the best way I've heard to put it is, we increased our luck surface area by encouraging more referrals, by having more volume of potential referral sources. And that was really a big eye opener that is still something I do to this day with my online businesses.
It's the same formula, you know? But it's online, it's more scalable, instead of the offline, more of the in-person events that we do at our office kind of thing. But what that did is that allowed us to get away from the sort of, wanting this marketplace where people realized, oh, I need a web development company. Because again, one of the things, the big eye-opener for me was the first time I started going to the local networking events, I remember when somebody would ask me what I did, I remember saying I ran a Ruby shop. And these are like Southeastern Virginia, good ol' boy kind of business owners, right? And they're like, I mean, they must think I'm some jeweler or something, right? Like they had no idea what I was talking about. But that was really a big eye opener because you know, a lot of these people could benefit from us, but there was a disconnect because we're selling, you know, you go to so many agency sites or consulting sites, and it's like, we make ideas real, or we're building a better web, or something like that. But if people don't know that they need, you know, is that resonating with the right kind of people? I mean it's gonna resonate with like the MVP crowd, the crowd that already like listens to startups, to the rest of us, and they get the stuff, and you know, it's gonna appeal to a certain segment, but is it appealing to everyone? Is it appealing to the kind of people who could best benefit from you?
You know, I work best, not with startups, but I work best with established businesses that I can go in and multiply, whereas with a lot of startups, you don't have any revenue or don't have any traction. You know, multiplying by zero is kind of risky.
So you know, it was a really interesting eye opener for me, that there's, you know, describing myself as a developer is only gonna appeal to people who have realized they have a problem that can be solved with development. And if we could go further back in time and help people along in that process, you know, ideally at scale, that's ultimately what got us to the point where we had, you know, a multi-month backlog of work for our team of 11, really at any given time. And that directly translated into what I did with Planscope, what I'm doing now, and so on.
Yeah, I like how you talk about not relying entirely on luck, just waiting around for people to, you know, find your business. In fact, you said you're increasing your luck surface area, right? So you're actually going out and talking to people about what it is that you do and about the problems that they have and how they can solve them efficiently. And you're really just being proactive in going after clients.
I know that when I was a freelancer, that's the exact opposite of what I did. I just sat around, and if people reached out to me, then that's great, I would have a job. And if they didn't, then I would just go weeks without having a job. And it turns out that all the best jobs that I got as a freelancer were a direct result of some sort of thing that I put out into the world for free, some project that I worked on that was popular, and somebody said hey, I want that to solve a similar problem for my business. And I never really caught onto like, maybe I should, you know, find a way to do that as a matter of course, you know? As an actual routine part of my strategy. I just let it continue to be luck.
I think a lot of people can do that with their businesses, right? If you have a product business, you can end up falling into the same exact trap, where especially as a developer, you put your head down and you write code for months and months and months, and you never actually think about, okay, well, who are my customers and what are their problems and what is an effective way for me to get in front of them and describe how they can solve their problems, ideally using a tool like mine? Or to get in front of their friends, who will then recommend them to me. So again, I think this is a great example of a parallel between, you know, a way that freelancers or agencies operate that also applies to entrepreneurs, you know.
Another thing that you said at the end was how much your business really, not relied upon, but was structured to help existing businesses grow, which is very parallel to the fact that if you're starting a business, probably you're going to make more money if you sell to other businesses who actually have more money because then you're not multiplying by zero, right? Like if you're targeting consumers, it's very difficult to find a problem that consumers are willing to pay you a lot of money for because there's not that many consumer-oriented solutions that are going to make individual people a lot of money, versus if you're targeting a business and you have a product or a service, even just as a developer, right, as a single developer, the service that you're offering can help any business probably double or triple or even 10X their revenue, right? Because they need your development skills. If you can price yourself according to the revenue that you're going to help them generate, then you can end up charging a lot more.
And that goes for product businesses and for just individual freelancing services. So I think that's a lesson that a lot of people could stand to benefit from. Even though it's very attractive to target consumers with their products business, you're probably not going to make as much money.
I mean, I've got a funny story about that. So before, I use Drip now for email marketing, but I used to use Infusionsoft. And I remember the day I signed up for Infusionsoft, they actually have a $2,000 setup fee. So just to get set up, you had to pay $2,000. So I paid that gladly, I knew what the software could help me do. I was moving off MailChimp and you know, I was really optimistic and motivated to transition to what, something that I thought would be much better for sales. So I paid this, paid $2,000 for this software. Later that night, I was laying in bed, flipping through the app store. And I remember balking at a 99 cent game, thinking like, I'm not gonna, you know, here I just paid two grand for business software, wearing my business owner hat, and now at night, in bed, wearing my consumer hat, and I'm like, who's gonna pay a dollar for this, right?
But you see this a lot. You see, you know, people who find the quote unquote sexy business that's like the next social network or the next this or the next that, and they really do struggle. I mean, some of them do well. You know, you see the unicorns that just take off, and even if they don't ever make any money, they get aqui-hired and they're happy.
But yeah, you're right. It's so much easier to go after and say, like businesses pay for things if they can either make more money or lose less money. Ultimately, becoming more profitable. So if you can help them generate more sales, generate more leads, generate something like that, that businesses want, that's great. And likewise, if you can help streamline internal operations, make it so they don't need to be passing the, emailing the Excel file back and forth around the office all day, which is what a lot of companies still do, yeah, I mean there's a ton of opportunity in the B2B space, but yeah, you're right. It's not as sexy. But it's one of those things where you can multiply by existing revenue or something existing and demonstrate, you know, an increase.
Yeah, I think you just have to redefine the meaning of sexy from appealing to people in a way that's fun and interesting to having a business that succeeds and makes you lots of money.
If you find that sexy, then the targeting businesses is very sexy.
I think, going back to your point about how you were able to actually reach out to customers and find clients by doing these kind of real-life webinars, across all of your businesses really, you've had amazing customer acquisition strategies. For Double Your Freelancing, for example, you put out a staggering amount of content that's really high-quality.
You also have this whole personalization piece where pretty much anybody from any walk of life can go to your website, and whether they're a designer or a developer or some other sort of freelancer, they get funneled to just the right advice for them, right? Whether they're an individual or running an agency, they get funneled to the perfect content for them. Which is something I'm jealous of because Indie Hackers, I do a terrible job at this. I just put it all on the front page and say, alright go for it, hope you find what you're looking for.
Can you talk a little bit about how you think about content and what you've learned about content marketing and actually being able to you know, attract customers and readers, write things that people find appealing and distribute it online?
Yeah, big can of worms.
Yeah, it's a lot.
So with, yeah I mean, so there's a few things, right? There's the, let's talk about free content. So let's talk about just blog articles or you know, stuff that's on your site, freely available, there's no email opt in or anything like that. My basic strategy is a series of upsells. So if somebody is reading an article of mine on my site, I'm asking for their attention, right? Like so it's, the purchase price is however many minutes of their time. And I have a lot of that, partly to appeal to Google, because I get a lot of organic traffic these days, where I've really put a lot of effort into thinking like, what conversations are people having currently with Google, and how can I intercept them?
So like very few people are going into Google, typing in like, pricing course or something like that, but they are typing in like, frustrations about working with clients or about getting underpaid or about like never having enough money or something like that. And what that's allowed me to do is realize that what they really need is, they're thinking that if they charge more, their cash flow issues will go away. I mean, that's really the, it's not about, for everyone it's not about having a better standard of life or about buying an amazing car or boat or something like that. For a lot of people, it's just about getting away from the ups and downs of running a freelancing business. So I did a lot of work, keyword research and stuff, into coming up with content that is evergreen, meaning it's not, the benefit of working and helping people with consulting is sales marketing tactics, pricing tactics, I mean, they don't really change day to day. They're pretty perennial.
So I you know, created a lot of this acquisition content, this content where I'm asking for attention. And then what I've been doing a lot of recently is personalized call to actions, depending on a lot of different factors, so where have you come from, what articles are you reading, and so on, so forth. Someone who's reading a lot on proposals, it's pretty safe to say, like that's what they're struggling with right now, is closing proposals. So the call to action that they see will be focused on closing more proposals. Then I get people into an email course that helps address that specifically.
Now, in a way I'm upselling, you know, they just read a bunch of content, or one piece of content. And I'm now upselling a free email course, where I'm asking now for both more attention and in this case an email address, so contact information. And that's, now they've been upsold, effectively, the email course. So they go through that. I do a lot of personalization again, where at the point of opting in, I ask them what kind of work they do. So now I know that they care about closing more proposals, they're a web designer, and I also ask throughout the course, I have these worksheets where I ask them other questions like, how long have you been freelancing, what is your goal, like what do you need to get from this course?
And I take all these factors and I start to slowly change the downstream content to be based off of that. So by the time they get to, basically what I do is I look at, I wait for them to hit a certain threshold of engagement, where once I know that they are hitting all the right factors that show like, they're really serious about what the free email course is helping with, which is pricing theory, now it's time to present to them my premium course on pricing that gives them all the, it's more turnkey, gives them all the templates and stuff that they need to get started with this.
Then they get a personalized automated pitch that compounds everything I know about them so far, tweaks all the pitch copy and the sales page copy, so if you go to the sales page, you know, and I know you're a designer who wants help with the proposals, you know, you're solo, let's say, or you run an agency, let's say, all the copy will be about design agencies and it will be about how the product will help you close more proposals.
Because ultimately, at the end of the day, people want products built just for them. That's why people talk about niching, and you gotta go deep and find a niche or something like that. And all I've done is I've made the niche the funnel, I've made the niche the marketing, the copy, and everything else. And I've kept a pretty much general product, right? So the product can help writers, it can help designers, it can help developers, it can help all these different types of people who have different reasons for wanting the product, but I've niched down the funnel, and it's worked brilliantly in terms of ROI. It's just been, like in terms of lines of code written for payoff, it's probably like the most valuable code I've ever written.
It's funny, because what you're talking about, like niching is one of the perennial challenges that I see people going through, where on one hand, it's really good advice to pick a niche. If you pick a niche then you understand your customers a lot better, because they're more similar to each other and they have specific problems that you can then identify and solve, versus going super broad, then okay, it's like how do you even write your marketing copy, right? How do you make it appealing when you're trying to appeal to all these different people who don't necessarily have the exact same problems.
And you know, a good example would be somebody creating a task management app and saying this is a task manager for everyone, which really means it's for no one, right? Because it doesn't, who's gonna use that, right? That doesn't solve any specific problem, versus saying okay, you know, this is a task manager for developers that's gonna help you keep your code base clean or something, where okay, now you're solving this very valuable problem for a specific group of people, you know where they hang out, et cetera. And your solution is, I mean I guess it's the same for freelancers too, right?
You could say, hey I'm a developer, which sounds great, cause then you can solve anyone's problem, which is very different than saying like hey, I'm like a user interface, a user experience expert who's gonna help your company improve your user experience and convert more, you know, leads. Or convert more visitors into paying customers, where what you do is a lot more limited, but now it's so much more specific that companies can actually understand how you're gonna help them grow their bottom line.
And then what you've done with Double Your Freelancing is kind of the best of both worlds, where rather than just going super deep, you've kept it broad, but then inside your website, you've just attacked all these small niches by personalization and allowing your website itself to kind of like evolve and flow and change based on the individual profile of the visitor.
Yeah, I mean, you know, to be honest, it came from when I was running Planscope and I had onboarding. I asked the same questions like, are you solo or agency, or I knew this based on the plan they chose. And then I also asked them what kind of work they did.
You'd go into the app, you'd sign up for a trial of the app, and then you would get, you know, the onboarding would be tailored to you. You'd get like demo projects about design if you were a designer. You'd get demo projects about, you know, development projects if you were a developer. But that makes sense, because that's a web app, right? Like you log in, you sign in, and then this is your data. Likewise, you go on Facebook, I'm not gonna see your friends, I'm gonna see my friends cause it's scoped to me, it's scoped to my user account.
So I thought, what if I took this same concept of like, what if I treated an opt in or an email click, you know, a click from an automation email back to my site, as an authentication event? Cause you can include in that payload like, basically the subscriber id of the new opt in, or if it's pre-funnel, if they haven't opted in yet, what if I just used the local storage or cookies even to track a lot of this stuff? And then what if I could also treat like my email marketing app as a data store, and record like, what they're reading and what kind of content they're engaging with and so on, what they bought. And then finally, what if I could just do the stuff I did in my Rails app but on my WordPress blog? Why not? Like it's just if-then statements, right?
So you know, I mean, it's just, it's that realization that I can do that kind of stuff on what has historically been seen as a static thing, a thing that needs to appeal to everyone and speak to everyone. Well, why can't we just do what we do in our software, in our web app stuff, and do that on our sites, on our marketing sites or our blogs or whatever else.
We've just gotten used to content being this static thing. I wonder in the future, like five, 10 years from now, if everybody's gonna be doing this, you know? Every single piece of content will be personalized based on kind of the profile that people have. And I would love to talk more about that, but some people from Twitter have asked some very interesting questions. And I would be remiss not to actually ask you those questions before we run out of time here.
One of the biggest things that Indie Hackers readers want to know and that people who really want to get into starting businesses want to know is how they can get started as a contractor. And the reason I think that's important to people is because if you want to start your own online business, you need time to do that.
And it's very difficult to find that time when you're working a full-time job, nine to five, 40 hours a week every week, versus if you can be a freelancer, which is what I was doing before I started Indie Hackers, you're a little bit more flexible with your schedule, and you can maybe work two or three days a week, you know, or you can work on weekends and spend the week building you project.
So let's say I'm an entrepreneur, in this position, I want to quit my full-time job, and I want to do some contracting to support myself as I start a product business, and I'm a developer. What route would you recommend for me to get into that?
Yeah, I mean the first thing I would do if you don't have a lot of availability during the day, cause you're full-time salaried, is I would really, the best thing you can do early on is to just build your network. I mean, it sounds trite and overused, but it's true.
Just going out and letting people know what you do and how you can help, I mean, cause again, like what you, if you don't have a client base, you don't have any potential referrals sources yet, so if you can do things like, one thing I really love the concept of is like going to existing events, like networking events or any of these kind of things that happen in any decently-sized city, virtually almost every night, going to one of these events, getting to know people, doing a lot of listening, and really getting to hear people out, what are they, ask them questions about their business and ideally how it intersects with the kind of what you do, so if you're a developer, I'd ask people about like what kind of, so tell me about like, technically what kind of technology do you have in place at your company, get them to talk, get them to tell you a bit about kind of behind the scenes stuff and ask them questions about like, so what kind of sucks about the way things are? I mean, this is a lot of the stuff I did early on, locally, where I realized like, a lot of people were really struggling with Excel.
I didn't even know people really used it on a, like people can go crazy with the spreadsheets. And I didn't know that cause I never really have used spreadsheets. So you know, I learned that, I listened to what they were saying, I built up this network, and I was able to do a lot of follow-ups and just say hey, you know, I was thinking about what you said, have you thought about doing this, this, or this?
So spend the time to build up your network, find ways of delivering value. I mean, this is gonna be value you're delivering individually, through a conversation, but it's a start. I mean, ideally, you want to eventually get to more scalable ways, like if you do a seminar or an online thing, or you have more evergreen things, like content you push on your site, your new consulting site, stuff that is always kind of there working on your behalf. But I mean, that's one way.
The other big thing is, you're time-limited probably, cause you probably don't want to be working all day and then drumming up work all night. Honestly, for a lot of new people, I would say like look for people who probably already have existing projects, right? Who have already gone down that funnel and have realized they have a problem that can be solved, and it can be solved by hiring a developer, go after that. You're not gonna get the kind of value pricing that you want early on, but it could be enough to initially support you so you can make the jump and quit that you know, your job and do this full time.
I'd also ask you know, your current employer, when you decide to quit, I mean, you've got a lot of domain knowledge most likely, and you know their setup, you know their infrastructure. There's probably a good chance, especially if they're gonna need to go and find somebody like you and go through the whole recruiting process and onboarding, if you can just stick around for a few months and you know, now they're effectively your first client. I mean that's the kind of stuff I would do if I was full time salaried at the moment and wanted to start my own business. Start there and then progressively kind of do more of a focus on building up your audience and stuff.
What I would also do is if you do plan on building a product, like you know, a software company. If the audience of that business can be similar to what you're doing on a consulting basis, that's even better. So if you want to eventually start like an A/B testing company, do A/B testing consulting. Do some sort of optimization stuff like that, so that, you're gonna learn a ton, you're gonna learn a lot about this audience, their needs, how they describe stuff, and everything else. But you can eventually set up like productized offerings that you sell to this audience and then slowly swap them out with software, you can slowly build.
So I have a friend who does metrics analytics, so he looks at companies and looks at kind of metrics deficiencies and so on and helps them improve like, organic traffic, I mean it's a broad thing he does. But he built this SaaS called Metrics Watch that is now, he's getting consulting clients through that because people come to that SaaS wanting you know, it's just metrics analytics, so you know, it'll basically look at your metrics and contact you when like, hey you're getting a spike in referral traffic. So people come in through the app. But then within the app, he's able to actually upsell his consulting by saying, hey, you're getting a lot more, this is your current organic traffic over the last week, would you like to look into figuring out how you can get even more organic traffic? So click here, and then he goes through this whole contact process. And for those who come to him directly for consulting, if they don't qualify, then he can downsell them on the SaaS.
So it's much better than going after audience one and then building a SaaS that you're starting over from scratch with a new audience. Ideally, if you can have the two be overlapping, that's a good thing.
I might not know how to do the value-based selling yet, where I could tell you, or I could identify a specific set of problems that are shared between different people and then pitch myself as the person who can help you get off of using Excel spreadsheets, et cetera, where I can sell for more and you know, develop my own personal brand. So how do people learn what they're good at and what value they can provide and the market actually needs?
I mean, I would look at, first off, do have any sort of unfair advantages? Have you worked in a business, for instance, that gave you a lot of insights into the oil and natural gas industry? Have you done a lot with maybe, to go back to A/B testing, maybe you're a developer who knows a lot about A/B testing because you've had to do that in your day job or it's a hobby of yours. I mean, these are the kinda things that can make you pretty unique in the market.
But ultimately, my big thing is I'm very reticent about encouraging people to go and say, like plant their flag as a web developer for hire because at that point again, you're only gonna appeal to people who know they need a web developer, which is a limited subset of people. And on top of that, the people you do get will generally be price-shopping you against other web developers. And what's gonna happen when you're wanting to charge 100 an hour cause that's what you need to stay afloat in the Bay area, and they come back to you and say well, there's this guy I found on Upwork in Pakistan who's $8 an hour, why should I pay you? And that's a really hard argument to, that's a really hard question to answer, right?
So you know, that's why I'm big on like, just get away from just stuff that happens inside the factory altogether. Just focus on like, what problems can I solve? I mean, it doesn't take, as long as you are pointed in the direction of knowing that people are not wanting to pay you gobs of money for code, but instead there's something else at play, just doing the due diligence to figure out what exactly it is that they really need and then using code to solve that. I mean if you do that, you're gonna be better off than like 90% of the competitors out there, right? Because everyone else is so focused on the tech, and if you can say, how can I leverage this tech to achieve a certain business end, and what is that business end and what does it mean?
Forget about the whole like, value pricing, everything else. You can and you should do that, but for starting out I would just say like, you can increase your levels of success by just focusing on, like basically removing the risk of hiring you. So if I hire a web developer, they can technically succeed, but they can still fail in terms of delivering what I need. And that's something a lot of us don't internalize that well, is that we can technically build a functioning web app that is by all means, by all indications complete and well-built and everything else, but it could completely fail to achieve the business ends that they need.
And the more we can do to focus on what is it they really need, and where are they now, and how can we help them get from here to there, and what does that mean scope-wise, what does that mean in terms of what we're gonna be building? That's what we should be focusing on. Cause you do that, and you're gonna be much lower risk, and you're gonna honestly have an easier time selling people. You're gonna come in as a partner, as an ally, from day one instead of just a hired gun. And it's just gonna be a better project overall cause you're gonna be delivering, ultimately, a better product if you stay focused on that outcome.
Yeah, I like the way that you put that. That you can be a web developer, and if they're hiring you as a web developer, you can succeed at being a developer and yet fail at accomplishing their actual business objectives. And so if you pitch yourself as someone who comes in to you know, directly target those business objectives, then it's a lot easier to, you de-risk yourself, right? You're someone who they can look and say, okay, this person's actually here to solve the actual problem that I want, which is getting more customers or converting more leads, et cetera, rather than just writing code and hoping that that code eventually, you know, achieves these objectives.
The last thing that I want to ask you about is what is the next step after that? Is it important for someone who wants to be a freelancer or consultant to develop a personal brand and create a website and a blog and start producing content? Or is it more important for them to continue just going to events and talking to people? How do they move to the next level?
I mean, events don't really scale that well. If you tend to have a very, I mean what I would do is, I would optimize to have recurring revenue that is you know, these kind of retainers that are more value-based, where they're not retainers of time.
You know, it's like, for instance my friend Nick, who runs Draft Revise, he does monthly A/B testing as a service. There's no indication of how many hours he puts in each month, just he gets like 15 people paying him a few thousand a month, and that's his revenue, and if one drops, great, it's not that big of a deal. He just has to find a replacement. But it's not, the likelihood that all 15 will cancel in one month is relatively low, and he's not on that hamster wheel of needing to go and find, you know, customers or anything else. He just, he has his MRR at like, multi-thousand dollar chunks at a time, right? So I would optimize for that.
I would also, over time I would look at ways to, a lot of the sales process is overcoming objections and educating people about like, you know, why it is they might really need to hire somebody like you. So if you can delegate a lot of that educational stuff to automation, that's all the better. So maybe go on podcasts, do guest posts, create your own content, and then lead people into a funnel that ultimately ends with a sales call. That's good too.
And the last thing that I would focus on would be, I call it roadmapping, but it's paid discovery, which is before trying to get somebody on like a you know, tens of thousands of dollars engagement, have something that's less pricey that's, you know, fixed scope, fixed price that you can sell first, that can be kind of like what I do and so you know, for instance I do a lot of big automation stuff when I do consulting work. But before doing that, somebody needs to pay me $6,000 to put together a roadmap, where I'm digging into their business, their existing, you know, customer valuations, how they get clients now, and so on, and I put together a personalized plan of action for them as a report and I do all this for them up front.
It's a way of kind of qualifying people who can then pay 10X for more of that to hire me outright for a consulting gig. So it allows them to go from, in my case, zero to 6,000 before needing to go from zero to 100,000, which is a much safer jump. It's kind of like you know, I'm basically just selling them something cheaper first before the trust is really established.
And I've seen that in my own business. I have a $9,000 course that I can drive all the paid, anonymous traffic that I want to, and it would get no sales, but people who buy that have gone through the $300 course, derived a ton of value from that, and then are now moving on this more immersive or high-touch course as a result of having experienced that win as a result of working with me.
So it's the same kind of thing, how can you give something, I mean, I've seen people do two, $300 roadmapping sessions where it's an hour Skype call, where they dig into their business, they look at what's possible and so on, and they treat that as a separate, preliminary engagement that needs to happen first, and then from there the deliverable is really the proposal. So the client gets this deliverable, which is really a proposal, and they're looking at it as a report instead of a pitch, and then they're basically upsold the implementation engagement from that initial roadmapping engagement. So that's the third thing that I would do.
So yeah, I mean, there's just a lot, and there's a lot of parallels with that in products, right? You know, obviously optimize for subscription revenue, find ways to systematically generate, qualify, and convert leads, and finally, if you're got some sort of product business especially, find ways of having a kind of like a stepladder approach, where people start off maybe small, in the internet marketing world they might call it like tripwire product, and then deliver value from that, and then basically upsell them on the bigger, more immersive, more expensive products.
I wish I could say this is a good place to end, but man, there's so much I want to talk about. And unfortunately, we're out of time I think, you know, you've got such an incredible breadth of experience across, you know, running your agency and doing product businesses and basically being an educator online. And I would love to have you back on the show at some point in time because I feel like you could talk for just like an hour about automation, an hour about content marketing, and an hour about you know, engaging customers, doing sales, and all of these different topics. So if you're up for it, sometime in the future we'll have to have you back on the show.
I'd love to, yeah.
Anyway, can you tell people where they can go to find you and find more about what you've written online?
Yeah, so my main website is DoubleYourFreelancing.com. That's where you can go and see a lot about what I talked about, if you want to dive deeper into, or you just want to see an example of a personalized automation sequence, you can go to FreePricingCourse.com, and that just redirects to a landing page on Double Your Freelancing. But that's kind of like my main entry point for a lot of people. And if you're interested on the personalization side of things, I encourage you to check out RightMessage, RightMessage.io, or you can also go to BrennanDunn.com, which is my personal consulting site, if you're into that kind of stuff.
Alright, thanks so much for coming on the show, Brennan, I'll see you later.
Yeah, thanks Courtland.
If you enjoyed listening to this conversation, you should join me and a whole bunch of other Indie Hackers and entrepreneurs on the indiehackers.com forum, where we talk about things like how to come up with a good idea and how to find your first paying customers. Also, if you're working on a business or a product of your own, it's a great place to come and get feedback from the community on what you're working on. Again, that's www.indiehackers.com/forum. Thanks, and I'll see you guys next time.
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