Brennan Dunn is a developer at heart, but over the last few years has taken personalization and marketing automation further than pretty much anyone I know. Founder of many companies but most notably Double Your Freelancing and now RightMessage, we geeked out on personalization, the steps he’s taken to go from some side projects to a six figure a month info-product company, and what he’s trying to do now with RightMessage.


John: All right, everyone. Welcome back. Today I have with me Brennan Dunn, who is a serial entrepreneur. He’s actually based in my home state of Virginia. But he’s at home right now in between traveling the world. Brennan has run many different business, which we’re gonna get into today. And he’s also working on launching a new software business that he’s gonna be doing in a slightly different way than he’s done it before. So hopefully, we’re gonna get into all of that. Brennan, welcome to the show. If you would, tell us a little bit about yourself, about the businesses you run, and yeah, tell us why you’re here.

Brennan: Cool. So thank you, John. So I guess my two things I’m doing now are, I’m the founder of Double Your Freelancing, where we help freelancers get better at the business behind their business. And my other thing, that I’ve started this year is I’m the cofounder of RightMessage, which is a website personalization software company that helps make it easy for people to speak a little more directly to the people viewing their websites.

John: Gotcha. So you’ve done a bunch of different businesses. If you could start from like what was your first business and give us the quick recaps of all the different types of businesses that you’ve run.

Brennan: Sure. So the first business that I really had. So in college I did a lot of the usual like web designing for friends, parent’s company and stuff, right? So I started kinda freelancing without knowing it was freelancing. But my first one was so I had dropped out of school to start this. It was really a personalization tool kind of. What I was doing was one of my clients that I had when I was in college had me build a landing page thing for him for his mortgage business. So we would run ads and get people to go to this landing page, single-page landing page, with his like branding and his logo and all this stuff in a contact form, right? And what we did is we just did a web share on, you know, money that came or sales we made through this.

And it did really well. Like I had no idea that mortgage brokers would pay so much money for a name and a phone number.

John: Oh, so much money.

Brennan: Yeah. So actually I was at a liberal arts school and was doing okay. But it was expensive. And I was kinda itching to start my own thing. So I started this company called Agathon Solutions with a friend of mine. And what it did is we just had a single landing page that we ran ads to. We ran like basically AdWords back when it was kind of much cheaper than it is nowadays. But we also did like media buy tip stuff and paid newsletters and stuff like this. Very new to it all, but as a programmer, what I did is I made it so like if you went to that landing page and clicked through from like Virginia and we just looked at your IP to figure out like where you might live, we would just randomly take our template and put in one of our Virginia customer’s branding and everything else. And then if that lead converted, we would email directly the name and, you know, the whole, the data from that contact form to that person.

So a lot of mortgage brokers were doing like Lending Tree or these kind of services where they’re like the 80th person to call a lead. And it’s really hard like because they all sell the same thing, right? So we were doing these kind of personalized branded leads that did really well. And then I think the mortgage bubble burst in like 2006 or whenever this was. So that’s when I…You know, kind of, the business fell apart but it did really well. And I learned a lot about kind of, you know, getting traffic and all that kind of stuff. But I ended up getting into the agency world working at an agency.

And then I moved up to Virginia. I was in Florida at the time and I moved to Virginia. And then I started freelancing and did pretty well. So I grew a company from that or I’ve scaled beyond myself and got up to 11 employees. We did pretty decently. I mean, we had an office here in Norfolk, Virginia. And then I got out of that in 2011 to start a SaaS called Planscope, which, go figure, as an agency owner, it was the project management tool that I wish I had when I went into business. So I did that, couldn’t handle running an agency and a SaaS simultaneously. So I exited the agency to focus full-time on Planscope.

Planscope, being a product management tool and a sea of other PM tools, was very hard to grow. So I started doing kind of typical content marketing stuff where I would write articles targeting the kind of people who would use Planscope. And that became Double Your Freelancing because people asked me for more information about what I was writing about. That led to a book, and then courses and conferences and all of that other stuff. So that’s doing well now. That’s my…it does seven figures a year. It’s pretty much myself. And it pays all the bills and a lot more.

But one thing that came from that is because I’m targeting freelancers, there’s a lot of different types of freelancers. So you have marketers, you have writers, programmers, designers, and everything in between. We also have agencies, and we have, you know, several people who are freelancers. And we can help them all. And one thing that I started doing a few years back was making it so like let’s say a web design blog sends traffic to an article on my site. I would just assume that people coming from that were designers. And then I would speak to them, ask them to go to like my product page or see an opt-in form or whatever as the designer. And it started working really well. So I really focused on kind of behind the scenes. The developer in me was like, “Let’s try to see what I could do with this. Like how far can I go?” And then I started pulling data out of the…my email marketing app drip and making it so like if you’re on my list and I know this about you and you’re on this product page, I’m gonna change that product page to like testimonials from people just like you or, you know, whatever else.

And I started to see like overall conversion rates for opt-ins, to purchases to everything in between just start to really go up. And this kinda got me on the radar of a few companies who were doing considerably more in sales than mine. And they’re like, “We want this.” So last year, I just built a course on marketing automation. And I bundled in a lot of the code I used on my site as like one of the bonuses, right? But then people would…you know, we had 400-ish people I think buy the course so far. And the number one piece of feedback was, “What the hell do I do with this,” right?

John: Right, right. How do I implement it?

Brennan: Exactly. So that led me in early 2017 to start thinking about, well, do I maybe make a SaaS product out of this code that I’ve written and make it so it’s a little more almost like a simple like Optimizely where you can just click on what you wanna change, change it, because what I had built required you to actually write some code to say like, “Here is the headline. And here’s the CSS, lucky for that. Now change it to this when this is true.” And it’s kind of annoying because you need writing or making changes required you to modify your code base, than use the tool let’s say. So yeah.

So I built up interest in 2017 for this. And it’s doing really well. And I’ve been focused on that kind of passively at the beginning of the year. And then in late spring, I was like, “All right. Let’s see if we can…you know, what would happen if we opened the doors and said, ‘Who wants in?'” And before we knew it, we had just more customers than I could have ever expected in the window we had, along with more interest. So I’ve actually made it more or less my full-time gig over the last few months.

We opened the doors in June and yeah, we’re doing really well and just a lot of stuff. Like it’s interesting because it’s a new audience for me. There’s some overlap. But it’s not huge. And what’s interesting is how it’s kind of new in that. A lot of people conceptually get it but no one’s really doing this. Not many people are saying like, “Hey, if they bought Product A and they’re looking at Product B, maybe you describe Product B a bit differently to them than you would to other people,” right?

John: Right because they have more context.

Brennan: Exactly. And it’s what we do. Like if I was talking to you about my business like right now, I would change the way…like if the listenership of your podcast were my mom and people like that, I would be describing the stuff differently, right? Like I wouldn’t use the word SaaS. They wouldn’t know what that means. So we do this already in person. So my thought was, “Why can’t we do this online?” And that’s kind of what we’re doing now with RightMessage. So that’s my new thing. That’s my kind of like latest thing that I’ve been focused on.

John: Totally. And I like that. I like that approach because, I mean, having been in the digital world for a while building sites and companies for a while, you know, we try to do it in different ways, right? Like you’re doing it kind of passively behind the scenes where you’re saying, “Okay. They visited this page and this page. And they came from here. And they’re in this location. So therefore, we should show them this messaging.” You’ll come to an e-commerce site and you’ll click through and answer like five questions about yourself. And then they’ll personalize it from there.

And you’re just doing it on the fly and requiring no input from them. They’re just doing their own like navigating of the site.

Brennan: I mean, you can do both, yeah. So the quiz kinda model where you give them like a survey. That obviously, works well and then you can…it’s funny. I’ve seen people who do these quizzes. But they don’t do much with the data. But what I’m interested in is what can we behaviorally figure out about somebody? So like if they come…like in my case, let’s say that you…I mean, I use surveys and quizzes also to figure certain data out, especially if I don’t know the data.

But if somebody is linked to my site from my web designer site and they’re reading articles on my site in the most popular or the kind of articles they’re reading the most about are around proposal writing, I can probably safely assume that they’re a designer who cares about proposals. So when I show them, let’s say they go to my home page and they see the hero call to action, it’s gonna be about how this helps them close more work. It helps designers close more proposals. It’s kind of like the same effect that a content upgrade would have, but on more of a…instead of saying, “Here’s an article on X. Shall we make it about X?” instead of saying, “Based on what we know demographically, where do they come from?” Maybe if we’re running, we’re targeting ads on them on Facebook, let’s say, we could take the same ad and say, you know, have it run, you know, men are gonna see this variation, women are gonna see this variation. And then even that, I could pass that data into my site so that, you know, they see testimonials from…I mean, for my stuff, the male, female, age stuff doesn’t really apply as much. But I could say like, “If they like “Smashing Magazine,” there’s probably a good chance that they’re a developer.” And I can pass that info in and then use that to kind of help me make an assumption about who they might be.

John: Totally.

Brennan: But then, I also do things like when you join my list, I send emails every Sunday, depending on what data I don’t have about you, that will say things like, “Hey, click…which one of these most reflects like what you want from us?” For instance. Like so one thing I ask is, “Do you want community? Do you want business training? Do you want to augment your skills? Do you want to overcome imposter syndrome?” And these are basically trigger links within the automated emails I send out. When they click that, it applies data to their subscriber records. So when they’re back on my site, I know, “Okay. This is, you know, John. He’s a marketer. He runs an agency. And he wants help with, I don’t know, like skill augmentation, like learning new stuff that helps.” I can then tweak testimonials, headlines, images. It’s usually not like much. It’s just tweaking random bits. But I’ve had pretty good success just by doing that.

John: Totally. So when you say, I mean, you mentioned a little bit ago that you like conversion rates and opt-ins and all that started taking off, are we talking like 2x or are we taking 5x? Like how much better did you do?

Brennan: Yeah, so. All right. So I used to have kind of the typical universal call to action on my site, like so if you’re reading an article, you see a call to action at the end. or if you’re on the home page. What I’ve done is I’ve just looked at, you know, behaviorally what kind of content are they consuming?

What category of content, along with what do I know based off of like if they came from a certain site or something like that? I had a lift of 250% in opt-ins just from doing that, yes.

John: Wow. Big.

Brennan: So, I mean, considering my lead value, that’s good.

John: Yeah, enormous.

Brennan: In terms of sales, so the one course of mine that I’ve personalized pretty extensively is my main course, Double Your Freelancing. It’s had about 8,000 customers over the last few years. It does very well. But I’ve simply just changed the headline, changed any instance of the word “freelancer,” to like, you know, freelance marketer or design agency or, you know, whatever kind of phrase you should be based off of data. And that alone has had a 70% lift in sales.

So most people who get there go through an email course beforehand. And in that email course, I ask people point blank like, “What is the thing you…like when you joined this free email course, what do you need help with? Do you want help with just learning how to price to begin with? Are you clueless about what you’re worth? Do you want help with value pricing or are you losing a lot of proposals? So click the one that best represents you. So let’s say they click value pricing. So if I know at this point they’re a designer, they’re an agency, and now that they care about value pricing, by the time you get pitched at the end of the course and are sent to the landing page of the product, it’s all about how this helps, you know, design agencies value price their projects. Whereas, a split second later a freelance developer who wants help with proposal stuff is looking at the same sales page, the product is, the description of the offer is focused on how it’s gonna help that person as a freelance developer basically close more proposals by doing this, changing the way you sell.

So, you know, it’s what you would expect, right? Like if I had a booth at a design conference or something, like, I mean, if somebody comes up to my booth, I’m gonna talk to them differently than I would somebody like at a marketing conference. So that’s where we do our offline and it’s just making it a little more accessible online.

John: Totally. Totally. And so you’re basically wiring all this up with, I mean, you have your site, you have…and then using drip for your drip emails. And I assume everything in there is tagged. Everything on your site is tagged with drips, with drip codes. So you’re just passing everything back and forth.

Brennan: Yeah. Drip is like my…your subscriber record within drip is like your user record, right? And any time you either opt-in or click on a link in an email I send you, I’m basically authenticating your device against that record. So now, like if you click a link that I send you in an email, I know this is, you know, John. And this is what he does and all that stuff, all the data I keep about you. And then that gets synced over to the site. So then the site can say like, “Hey, if, you know, the first thing’s equal to John, you show this or something.” Right? Not that you have to do that but I could.

John: Yeah, totally.

Brennan: So yeah, that kind of stuff.

John: Well, and the beautiful thing is that works across a platform, right? Like it doesn’t matter if I’ve check email, you know, on my desktop, on my laptop, or on my phone, right, because like it’s all based off of that email record. Like you know who I am. So it’s not like cookie-based necessarily.

Brennan: Right. So but that being said, if you did come in like incognito, I’d have no idea who you were.

John: Right. I am gonna go and look around because I am on like your drip, like email course, like your seven-day like pricing course or whatever. I’m gonna go click around and see if I can find some of your responses. So like see what I can do and that’s super interesting.

Brennan: It’s pretty subtle. But it works.

John: Yeah. Can you do stuff like do you show different things based off of laptop or a mobile phone or anything or whatever?

Brennan: Yeah.

John: Because I know one thing, like, one challenge a lot of people have is, you know, their mobile conversions are just so much lower, you know, than their desktop conversions like especially in the B2B space, right? Like Double Your Freelancing is B2B. RightMessage is B2B. So like you’re not going for, you know, generally to scale, right? You’re not going for millions of like customers, right? But since so many people are on their phones these days and the consumer-ship happened faster, but the B2B-ship is definitely happening, what do you do there?

Brennan: Well, two things. So if you’re not on my list, I generally want you on my list before I wanna sell you on anything. So you’re right, on phones, people are less likely to buy. So if you are…let’s say you’re anonymous and I don’t know who you are. A call to action’s usually gonna be about…like I’m not gonna push products on you because you don’t know me yet. But if you’re on my list already and you haven’t bought product X, then you’re more likely to get a pitch for product X, right? So let’s say you’re reading an article of mine that I email you in my weekly newsletter. You click through. If you’re on my list, you’re not gonna see an opt-in form. You’re seeing like promotions for the next thing, which is usually some sort of lead magnet bullets. What’s nice is with this like one thing I’ve started doing that I’m about to roll out in a better way is let’s say I have a lead magnet that links to an article or it’s something that I want you to do that will eventually pitch you on a product you don’t have, one-click opt-ins. So I already know your email. You’re on mobile. You just tap okay or whatever the button says. And now you’re in that sequence, right?

John: Totally.

Brennan: So that’s really powerful because what I’ve done, what I’m about to roll out with that is the idea of like a content upgrade where you’re reading an article and here’s like a check list that relates to the article. It’s such a wasted opportunity when you’re sending your list to that article.

John: I mean, that’s clear enough.

Brennan: Like “What’s your email?” Right?

John: Yeah. It’s frustrating.

Brennan: And they might take into a different email of theirs. And now you’ve got two records for the same person. So what I’ve done…I ruthlessly try to eliminate email forms, if I know who you are. But on top of that, one thing we’re rolling out is if you’re on my list and you’re reading an article with a content upgrade, to unlock the content upgrade, you need to share it on Facebook or Twitter.

John: Ah, smart, yeah.

Brennan: And then if you’re anonymous, meaning you just came from somebody who shared it on Facebook or Twitter, you need to get a new opt-in with your email address. So depending on kind of…yeah, so there’s just so much you can do with that stuff. But yeah, I mean, in terms of just mobile like device checking or probably better resolution checking, I don’t do much with that outside of like if the call to actions I have, if you’re on desktop or bigger resolution, then you tend to see like a slide-up banner. But if it’s mobile, it’s in line baked within the article. I take that and I kinda repeat it kinda how the article is.

John: Yeah, gotcha, gotcha. You know, that’s super, super smart. I think mobile is one of those things that marketers are really starting to come to grips with. And, I mean, like I come from the SEO side. So all SEOs are like, “Oh, they’re moving to a mobile first index soon,” right, which like yeah, really does matter. But at the same time it’s like, yeah, you don’t wanna lose your traffic. But at the same time, it’s like what if we’re converting more of the traffic that we’re getting, right? And like A, get qualified traffic, B, seal that qualified traffic, C, convert more of that qualified traffic.

Brennan: Exactly. Yeah. And that’s the stuff that to me is when I can play around with or when I can increase sales or conversions by not getting to work on traffic gen or redoing my product line upward pricing or anything, but I can just optimize a little bit, to me that…it’s usually for the amount of effort that goes into it relative to the result. I mean, like with me, if I wanted to get 250% more opt-ins traditionally, I would need to get 250% more traffic, right? But this allows me to optimize the current traffic I already have and just do a few different things. I mean, the angle would be obviously to have content upgrades that are specific to each article because nothing will be beat those. Because if you have an article on like starting a freelancing business and then the call to action for that article is a check list that relates to that article, that’s gonna do really, really well.

But that’s time consuming. And so what I’ve done is I kind of have something in between where I’m saying like, “If you went on that article, I am putting you in the beginner’s segment.” So the call to action’s gonna be something around that. And then yeah, I mean, I can assume, again, if you Google and you’re now on that article, you’re probably not looking to like grow an agency, right? You’re like starting out, right? So by virtue of where you came from and what kind of content you’re reading, you’re telling me a bit about yourself.

John: Totally, totally.

Brennan: So yeah, it’s just using that to my advantage, the right words and phrases.

John: Absolutely. And I’ve done some of that on Credo, as well, just like basic, you know, if you’re on this page and then you click to this, you know, conversion form, like on my site if you’re on like the SEO consultant’s page and then you click the “Find a Marketer” button at the top, it’s automatically gonna fill in SEO as what you’re looking for.

Brennan: Oh, nice. Very cool, yeah.

John: But if you’re on like content marketing, it will be content marketing. On Facebook ads, it will be Facebook ads. And then if it’s on like…I have like seven. And then if it’s any of the others, then I have an “other” field which then drops down another form field to ask like, “What are you looking for?” And just that in and of itself, I saw a 30% lift.

Brennan: Yeah. I mean, it’s little dumb stuff like that, right, that just works so well.

John: Totally. Totally. And you have to do…and over time, you do a bunch of them, you fail on some of them. Some of them work, some of them don’t. But the ones that work, you know, like you get that 30% lift, it’s not like a 30% one-time lift. It’s like you keep that 30% lift. That’s your new baseline.

Brennan: Not only that, it stacks. I mean, you get a lot of these little things in motion they just kinda stack on top of each other.

John: Totally. Totally. Yeah. So let’s back up. So I wanna switch gears a little bit and talk about Double Your Freelancing because it does seem to be an awesome product. It’s something that the emails I’ve gotten from you are like, really, especially for beginners and people that haven’t, you know, been in the business for a long time, haven’t been selling work for a while, it’s like it’s paradigm shifting. So I guess I’m curious about like within Double Your Freelancing, like where did you start with that? Like how…because you’re an agency owner that then went to doing that. And there are a lot of agency owners and consultants out there that wanna do software, you know, or like launch courses instead of, you know, doing services necessarily. And I know you still do some services. And most consultants do, even if they have a product. But yeah, like where did you start? And kinda what did that journey look like because you didn’t go from zero to making, you know, six figures a month, you know, in six months?

Brennan: No. No, that’s right.

John: Definitely, that, yeah.

Brennan: A couple of years.

John: Yeah, totally, which is what a lot of people don’t understand.

Brennan: Yeah. I mean, so with me…okay. So I, you know, I had the SaaS, right, with Planscope. And I wanted people to sign up for it. And the amazing thing about websites is having a website doesn’t actually mean you’re gonna have anyone looking at it, right?

John: Totally, true.

Brennan: So I was looking at like what do people do to get people on their SaaS, like to sign up for the SaaS? And there’s a lot of tactics out there. But the thing that kept coming up was content marketing. So the idea was relatively few people are Googling around for like agency project management software. But a lot of people were searching for how do I price or how do I get clients or how do I do this? And on top of that, I realized the clients or the customers I did have, when many of them cancelled, it wouldn’t have to do with the product itself. Oftentimes it would be, “I don’t have work, right? I’m out of projects.” So that was one. Okay. So that got me thinking, “Well, what could I…” You know, I learned a bunch about running an agency…having run an agency. Well, what could I…Maybe I’ll just write articles about things I’ve learned. And I would largely just get involved with online forums like reddit. And there used to be one. I’ve forgotten the name of it, but Freelance Switch I think used to have a pretty good forum.

John: Yeah, something like that. Yeah.

Brennan: Yeah. And I would just…like I noticed the same threads kept coming up again and again. And I realized, well, they’re probably…like they’re asking Reddit that question. But they might also be asking Google that question. So I would just go and kind of not only get involved because writing content and then, I mean, you know about this a lot more than I would. But writing content and getting people to organically find it on Google, to me I didn’t really have a…it’s kind of demotivating to write a big long article, get published, and have no idea if anyone’s actually reading it.

John: Yup, totally.

Brennan: So what I would do, is I would just get involved in conversations online in these forums and say, “Hey, let me think about…you know, here’s like a few paragraph response. Give me a bit. I’m actually…I think I’m gonna write something a little more in-depth on this.” And then I’d do that. And then I would circle back and say, “Oh, here’s kind of my real, my actual answer, right?” And so it wasn’t very spammy because I’m actually participating in the discussions.

John: Yeah, totally.

Brennan: And that kicked things off. And then, you know, I did that for a while. And then slowly but surely, the organic stuff started to ramp up. And but that’s how it started. I mean, I realized people were not Googling for software. They were Googling for, you know, to ask questions to Google about something else. But demographically they were kinda of the right mold, right? So actually the mistake, I mean, was that people thought like somebody searching for how do I raise my rates and they’re reading an article about that, the worst possible call to action is, “Hey, here’s my, you know, project management, you know, software.” There’s a complete disconnect there, right?

So that’s when I started doing things like looking into these email courses. And back then, they were very linear and stupid. But they kinda worked.

John: They worked.

Brennan: But yeah, I would just get a lot of the same questions again and again about certain things that I brought up. And that led to a very simple and cheap e-book about four and a half years ago which was called “Double Your Freelancing Rate.” And then now this is the fourth version of it. But it’s become a full online course. And from that, people would then say, “Okay. Great. Now help me systematically get more leads.” So that led to another product. And then people who wanted a little more community. And that led to going out, you know, on a limb and basically saying, “I’m gonna start a conference.” I did five of them so far. And yeah, I mean, one thing always led to another it seems with what I was doing.

So at first, Double Your Freelancing was a content marketing initiative.

John: That’s so funny.

Brennan: And that’s all it was. And then I remember because I had all these different single-page domains for my products I upgraded because it didn’t feel right to put them on Planscope. But then the articles were on Planscope/blog. And then had my podcast. And what was it? Two years ago, maybe two and a half. I think it was two years ago actually is when I consolidated everything under the new domain with all the articles over, obviously, the ones about Planscope.

John: Interesting. About Planscope, yes.

Brennan: Yeah. Planscope updates I kept, but on everything else, I moved over…moved over the core stuff. And yeah, I mean, that’s when it became like a proper brand I would say.

John: Yeah, that became like the canonical place for like all the stuff you’ve shared over the years, whether it was for Planscope or on your personal site or wherever.

Brennan: Exactly.

John: That became the place. So it was just like epic, I mean, epic like backlog of content right there, content marketing, that, you know, it still generating traffic. So you could kinda take off like out of the gate.

Brennan: Yup, yup. Exactly. Exactly.

John: Interesting. So what about pricing? I mean, pricing is one of those things and not like how do I sell better like services? I think, you know, you cover that in, you know, in Double Your Freelancing. But when it comes to pricing for your product, right, like how is Double Your Freelancing structured as far as like payment is concerned? And have you been through like different iterations there?

Brennan: Oh, yeah. So I mentioned when I was in e-book, it started at 29.

John: Yup. Just 29 bucks you get a PDF to download?

Brennan: Yeah. Currently, it’s $297 for the full package of Double Your Freelancing Rate, which is my main product. It’s kinda like the first product most people buy.

John: Yeah, just a one-time fee.

Brennan: Yeah, a one-time fee, although I down-sell installment options, which I’m actually backing away from considering the card failures were…anyone who can’t put $300 on a credit card probably is gonna have some credit issues. So that’s my main thing. But then I have like a course I’m redoing called “Sell Your Cell Phone Line,” which is a course on lead gen from your site. I have “Mastering Project Roadmaps,” which is about doing paid consultations prior to a project. I used to have “The Academy,” which was a $9,000 program, which was seven months long, very intensive and…

John: Okay. Kinda like the foundation, but for service businesses?

Brennan: Pretty…that’s a good way of putting it, yeah. It was very…everything was live. But in terms of workflow, a lot of work.

John: More work.

Brennan: I mean, I had 14 people helping me with that one product alone.

John: Oh, my gosh.

Brennan: So it was kind of like a little agency. I didn’t wanna do that though. And it was a great product. It was just really hard to run and stuff.

John: Yeah, totally.

Brennan: But then I have a course on automation, which is kinda like the first…I was on the fence about, “Do I actually do this?” I wanted to but I thought it might have been a distraction from kinda the business training I was doing. But we were wanting to or my rationale or whatever, how I rationalized it was thinking, “Well, I can help freelancers who are good at like building sites or coding stuff to add a skill to their skill set that doesn’t take a lot of time. I mean, automation just requires learning the tool and some of the best practices on using it. And they can effectively upsell their client on, “I’ll help build your site. But I’ll also wire some stuff so when you generate leads from that site, it can, you know, do this, this, and this.”

So that was that. And that’s done really actually really well because people…I mean, it’s 10 hours of video content. It’s pretty in-depth, but people really, really like it. So yeah, I mean, that’s Double Your Freelancing. It just kind of, it’s fully automated in that people coming in. They go through this kinda like I call it a plinko board of different things, depending on what they do behaviorally, demographically who they are, and what they’ve bought and so on. So I optimize putting people top of funnel and everything down from there just works, putting first sell, upsells, cross-sells. All that other stuff is pretty automatic at this point.

John: Pretty dialed in at this point, yeah.

Brennan: Yeah. I mean, obviously, it’s stuff I have tweaked over time but for the most part, yeah. I mean, even the pitches, I don’t do like the typical internet marketer pitch every three months. I mean, instead, it’s based off of what you’re doing.

John: Totally. And you’re like one thing I like about it and I like about the way that you’ve built your business is like you’re looking to add value every single step of the way. And then you’re also…you know, it seems like you almost have a process for like okay, people have asked this. And so I built this course. And then after this course, people are asking this other thing. So let’s try this other thing, right? And then like you basically built out a full like pipeline of like, “Okay, if you’re just starting out, you start here,” and basically just take them all the way along. But you can upsell into different courses. But along the way, they’re making more money because they’ve taken your other courses, right?

Brennan: That’s what it is, is the financial risk of investing like let’s say, 300. For a lot of people it’s not that huge. But investing $9,000 in the Academy is. But everyone who joined the Academy effectively came from…you know, they bought this and got a lot of results from it. And then they bought the next year, got more results. And with each time they tack another digit to the end of their product’s price, it becomes a little more immerses. So there’s hand-holding there. There’s one-on-one, as the stuff at the top of the funnel is more, you buy this, you get something prepackaged and generalized. And you go with that but then you can kind of go down the ladder.

John: Totally. Totally. Yeah. And so like, I mean, having those different levels makes sense because it’s something I’m thinking about now. With Credo, is like, you know, what level, depending on like price point and all that, you know, what do you get for it? What level of support do you get? Like how much is that automated? How much do we actually do for you as opposed to like, you know, because you can’t give…I had one person that they signed up to Credo at the very bottom level. And they churned out after two months. And they were like, “Oh, I was hoping for like, you know, warm introductions that are, you know, ready to convert right now.” And I was like, “For $100 a month? Like you gotta be kidding me, right?” And then these bottom ones, you know, true like Tim Ferriss’s style, those bottom ones take…you know the bottom or the 90% that are paying you the least take up 90% of your time.

Brennan: It’s true.

John: And the ones that are paying you the most, like those are the ones that you can give more time to. And they take up like…but they’re not taking up like support time, right?

Brennan: That’s right.

John: And so then you’re figuring out how to optimize that, as well.

Brennan: And that’s especially true for anything recurring like Credos and that. For one-offs, to be honest, a lot of the one-off three-figure sales are pretty like supportive. $100 is not much but once you get recurring and people need to basically justify, “Why am I paying this?” Then that’s something you need to think about, essentially and so, yeah.

John: Totally. Yeah. Yeah. Interesting. Well, Brennan, any final words of advice for people that, you know, are watching this and they, you know, they’re either… So two different, I guess personas. One is the people that are doing services. They’re consulting or an agency and wanna do a product. What would you tell them? And then people like yourself, you know, or like myself that, you know, you’re an entrepreneur. You’re constantly building out products. You, obviously, like love to write, love to build things. But you’re also not willing to go and build like huge teams of people, right, of like full-time people. So like what advice would you give them? Like, you know, if they’re just starting to make the shift to like getting other people to do stuff?

Brennan: Yeah. So about the latter point, I historically have shied away from it but with RightMessage, it could look like it’s more of a business that would require more than just me and a handful of people. So I’ll put that out there now. But at the moment, yes. But let me first address though the question of like if you… So starting out, right? Mistakes I made and what I would recommend you go do, it’s very hard to start with software, especially if you don’t have an audience. It’s extremely difficult to…because it requires a lot of R&D. And then, you know, especially if you don’t have the history of doing low touch sales, it’s really…you know, it’s easy for us to think, you know, we’re fully invested in this product. We understand it. We understand why it’s obviously bought. But learning how to communicate that effectively online in low-touch way’s a very hard thing to do.

John: Yes.

Brennan: So the best thing you can do is probably just start out with things that, in the words of Paul Graham, don’t scale. So you know, for instance with RightMessage, if you look at the history of that, I somewhat validated it or the validation I did that most people would take as validation was, “Hey, this worked well on my own site. I might as well make it a product.” But what I did for years, well, not years, but about a year and a half, is I mentioned I do consulting. I occasionally consult and I only consulted for the purposes of seeing how else could I take those from working for this on my own stuff and do it on other people’s businesses? Mine went off or could this be a little more universal?

John: Right.

Brennan: So the consulting I did was effectively hand-coded implementation of what RightMessage is currently. So people were willing to part with a lot of money to get certain results. And that to me was great validation.

Then I kind of opened up a circle by making it a course where I taught people about personalization and included a lot of the do-it-yourself code that you could then tick, a lot of which was the IP that came from my client work. So then that now 400 plus more people were willing to part with their money to learn a bit, like they were interested in the outcome. They were interested in that.

So then now that I had people who I’d done a lot first manually, then more low-touch with like a proper sales page and everything, but at first just over email. I really figured out a lot about kind of what people were…wondering how they describe their problems, what really clicked with people when it came to the promise of a product like RightMessage. So that when I had IP and the semblance of a sales page for RightMessage, and at first you couldn’t…like with the RightMessage sales page, was really just a teaser page that led to opt-ins where I would then communicate over email back and forth, back and forth in a dialogue format with the people interested. And then only when I was confident of if I’m gonna switch from a dialogue conversation to a monologue, which is a sales pitch, only when I knew enough about who I was gonna be speaking this monologue to was I confident enough to do that. Because before that, it was all high-touch, conversational back and forth, which allowed me to really…

John: Like you are manually talking with like those 400 people that signed up for that course or whatever?

Brennan: Mostly for that course, it was mostly within the Facebook group. So I’d tease out different things about what I wanted to do to get conversations going. So at first with clients, it was one on one. And then it became a group session. And now it’s a Brennan to many discussion or monologue I should say.

So that process is something that with Double Your Freelancing, when I do products now, I don’t start with the sales page. I start with, “Hey, P.S. of my newsletter for the week. I’m thinking of doing X. If you’re interested, reply back and I’ll tell you a bit more.” And then people reply. And then I might have a template I’m working off of. But for the most part, I personalize it a bit. And then they reply. And I drop down further and try and sell them without having any web page. And by selling them without having a page put together at all with the “add to cart” button, I’m able to really figure them out in a way that I couldn’t do if I just said, “I’m gonna build the most amazing sales page ever, blast it out, and hope it works.”

John: All the best practices and yeah. Totally, yeah.

Brennan: Which is risky.

John: Very.

Brennan: I mean, you could follow all of the best practices but that doesn’t mean it’s gonna work. So by doing the stuff manually at first, I mean, that’s the one thing I would not change about the way I’m doing stuff is everything I do that’s new, I start with this like, “Let’s jump on a call, let’s email back and forth. Let’s do it that way first.” And then, “Hey, are you interested in buying?” John replies, yes. “Okay. Here is the link. And it’s like a link to some payment form.” That is the way that I’ve done it and it’s worked best.

John: So you will actually get them to pay you before you even like fully built it out.

Brennan: Yeah. Oh, yeah. I mean, that’s…I’ve pre-sold t RightMessage and the marketing automation course I did before that kinda led to it.

John: Mm-hmm, gotcha. Well, yeah, that sets…I mean, that’s super-smart. That’s the way…especially when you’re boot-strapping, right, like get that payment up front. They’re basically paying you to build out what they’re paying you for, which is awesome.

Brennan: Exactly.

John: Yeah. A lot of agencies will like, you know, take their consulting revenue and try to…you know, if they’re running a profitable agency, which a lot of them aren’t. But like if you’re running a good profitable agency, then you can take some of it and invest into other things that your clients are gonna be, you know, interested in, right. Or have said they’re interested in. But if you can actually get like new people to pay you for that thing, you know, that’s even better because then you can have all these like crazy upsells and cross-sells.

Brennan: Exactly. Exactly. And it’s…I mean, a lot of…I could talk a lot about agencies building their own products. But a lot of them don’t commit to it like an actual client project. It’s more of a, “We’ll do it when we have time.” And it’s one of these things that you need to actually… The benefit of doing this approach is you don’t need to pull people off of client work to build out this great marketing funnel or this great product or anything. You can just converse over email. It’s so much simpler. It doesn’t take much time.

John: Totally.

Brennan: And then once you get the validation of people actually saying, “Yeah, you sold me. How do I sign up,” then go and actually formally take people from your team and have them work on a certain thing.

John: Well, especially if the validation is like they’ve paid you, right? They’ve given you their credit card information. Then it’s like, you’re not taking them away from consulting. Like you’re not taking them away from revenue-generating things. Like you’ve already generated revenue. You can take them out of that and they can make you more revenue.

Brennan: Exactly. But it’s really…I mean, I’ve seen a lot of agencies who build SaaS, who have no idea what they’re doing with low touch sales because they’ve only done high-touch. You don’t wanna do high-touch with the SaaS because that’s why they’re doing the SaaS. And then they just stumble and fall.

John: Yeah. So totally. Awesome. Well, Brennan, you’ve been super generous with your time. So I don’t wanna take more of it. But thank you for joining me. I really, really, really appreciate it. I’ve learned a ton. I’m sure people watching have learned a ton, as well. Where can people find you online?

Brennan: Yeah. Thanks, John. So the best places would be I have a contact page that has like my social media stuff and how to…you know, me and everything else. But if you wanna jump right to Twitter, Brennan Dunn, B-R-E-N-N-A-N-D-U-N-N, is the best way to reach me there.

John: Awesome. Well, Brennan, thanks again. And I look forward to following your journey and seeing what you do next.

Brennan: Yeah. Thank you, sir.