Brennan Dunn - RightMessage

RightMessage: From SaaS Founder Fatigue to Focused Growth – with Brennan Dunn [389]

RightMessage: From SaaS Founder Fatigue to Focused Growth

Brennan Dunn is the founder of RightMessage, a SaaS product that helps increase conversions by showing website visitors the right message at the right time.

In 2017, Brennan and his co-founder decided to turn a JavaScript library Brennan had built for his email marketing course into a full-fledged SaaS product.

They managed to raise $500K, thanks to Brennan's existing network and relationships from his previous successful ventures.

The product launched in early 2018 and quickly grew to $35K monthly recurring revenue (MRR) within the first year.

However, the founders soon started experiencing problems.

Firstly, customers were struggling to implement the product and didn't have the pre-existing data that the product needed.

Secondly, the founders hired quickly, leading to a high burn rate and eventually running out of money.

As a result, the business stopped growing and struggled to get new customers, forcing the founders to downsize the team.

The lack of progress also drove both of the founders to lose motivation and focus on other projects instead.

Eventually, Brennan bought out his co-founder using his personal savings and started to focus on rebuilding the business.

He narrowed his target market to online creators. By offering personalized onboarding to land influential customers and build credibility, Brennan has managed to start turning things around. After years of stagnation, the business is growing again.

In this episode, you'll learn:

  • How Brennan overcame a period of stagnant growth and demotivation by narrowing his focus to a specific niche and rebuilding his product.
  • Why doing things that don't scale, like personalized customer onboarding, can be a powerful strategy for reigniting growth in a struggling SaaS business.
  • How leveraging founder relationships and targeting influential customers can unlock growth opportunities for your startup.
  • What strategies Brennan used to lower friction for new customers and expand his top-of-funnel, leading to a resurgence in growth.
  • Why building a business that aligns with your desired lifestyle and making time for passions outside of work are essential for long-term founder success.

I hope you enjoy it.


Click to view transcript
[00:00:00] Omer: Brennan, welcome to the show.

[00:00:01] Brennan: Hey, thanks, Omer Omer. Thanks for having me.

[00:00:03] Omer: Do you have a favorite quote, something that inspires or motivates you that you can share with us?

[00:00:07] Brennan: It's not a quote, but it's something I  kind of learned the hard way early on, which has stuck with me ever since. So, and that is no one's ever paid me to code.

[00:00:15] I. This is something that has carried over to my product days where I think if you're like me and you're a technical kind of founder, you get obsessed with the features you get obsessed with, like the, the building of it, the architecture and all that stuff. And the thing I had to really, it's still one of these things I struggled with constantly is the realization that I learned way back when I used to do a lot of consulting was clients didn't hire me for code.

[00:00:38] They hired me for business benefit. Right. So that's kind of my, like, I'm not a quote person, but that's my like, grounding thing that I'm always like, if I could put that on a wall, I should, but that's, that's what should be there. 'cause I, I do get distracted by like rabbit holes of code and architecture and all that stuff that is important, but ultimately isn't what people buy.

[00:01:02] Omer: Yeah, no, I love it. And, and I think I, I'm very much like you. I, I find it coding is a great way to just disconnect. Do something. It's therapeutic. Yeah, therapeutic. Yeah. Many people would think we're insane, weird, insane. But yeah, there's something definitely there if you, if you're built like that.

[00:01:23] So tell us about Right Message. What does the product do? Who's it for, and what's the main problem you're helping to solve?

[00:01:30] Brennan: So we, we help companies that do a lot with email marketing better understand segment and personalized their email list. So we tend to work with, nowadays mostly creator type people, so we call them pro creators, which would be.

[00:01:44] Not pro creators, but pro space creators who who are doing seven, eight figures a year. Usually selling courses or coaching. But we also have a smattering of like software businesses, media brands, and even agencies who use us.

[00:01:57] Omer: Great. So maybe just explain a little bit how the product works because there's, there's different components to this.

[00:02:06] There's the experience that people get when they visit. The website, there's integration with whatever email service provider you may be using. There's some level of personalization that gets delivered on the website, so. Maybe just describe what that experience looks like and which parts of that is driven by Right Message and what, which parts are kind of supported?

[00:02:31] Like, you know, the email marketing piece?

[00:02:33] Brennan: Yeah, good question. So we're, we're easiest thought of as a bridge between your email platform and your website. So what that means tangibly is if somebody from your list goes to your website. You segment them as like a customer, so they're tagged with customer or whatever else.

[00:02:50] That data gets pulled to your site. And then you can make changes on your website depending on that. So, you know, for example, you could say like, if a returning email list subscriber's back on your website, don't show email opt-in popups, right? Like, don't show the popups, show a sign up for trial. You know, call to action if they haven't started a trial or they're not a customer.

[00:03:10] Likewise, you can also do things like, you know, changing out logos depending on. What industry they're in or showing a different case study or something like that. So we make it really easy to pull data down and also to collect data through behavior, like what pages they're visiting, what ad campaigns they came from what kind of content they're reading, the most of what affiliates sent them, along with what we call zero or not we call, but what the industry calls zero party data, which would be surveying.

[00:03:37] So, you know, we can collect this data and then send it right back up to the email platform, which you can then use for future interactions on the website or to then send better, more targeted email campaigns.

[00:03:49] Omer: Got it. Yeah. I was reading something about predictive intent the, the other day, and it, it sounds like that's basically what you are helping to achieve in terms of figuring out.

[00:04:03] When people are most likely to want to buy, to engage to what they need, and then getting that right offer or content in front of them, something that Netflix does very well in terms of helping us to binge watch.

[00:04:19] Brennan: Yeah, and that's, that's another thing too, like I, I always bring up the Netflix example 'cause they don't just do the recommendation engine thing, but they also go as far as to change the cover art for films to be like, oh, I like Robert De Niro. So if he's in a film and they show me that film, it's probably gonna be him on the cover. Whereas somebody else who likes, you know, some other act actor would see potentially somebody else.

[00:04:42] Omer: I did not know that.

[00:04:43] Brennan:Yeah, they do that. It's wild.

[00:04:45] We're not that behavioral Science, to be honest.

[00:04:48] A lot of the way that people use us is a lot more straightforward. Like we basically allow people to set up flow charts or automation campaigns. As a flow chart on your site. So you could say like, alright, if somebody's on my site and they are anonymous, I wanna show them my newsletter opted for 'em.

[00:05:06] But then if they're back and they're not tagged customer, I wanna show them my promo to be a customer. And if they are a customer, I want to get 'em to like a, you know, affiliate page or something that I have. So usually what people are doing with us is to kind of use us as a routing tool to show different content, you know, whether those be popups or call to action buttons in your nav or different hero areas or whatever else.

[00:05:30] Depending on who you're and what, what you should do next. And the benefit of us is we, we work as like a JavaScript to include, so it's not dependent on any content management system. You don't need to use us, you can keep using WordPress or Webflow or whatever else. And that, that's been kind of nice and compelling for a lot of people too.

[00:05:47] Omer: Great. Give us a sense of the size of the business where you, in terms of. Revenue, number of customers, size of team.

[00:05:52] Brennan: Yeah. So we're at about 20,000 in MRR which I'll get into more of that later as to why we're not higher. And we have about 250 paying customers. And our team right now is three and a half effectively.

[00:06:04] So three full-time, and then a part-time person helping with design right now.

[00:06:09] Omer: One of the reasons I I wanted to, to invite you onto the show was one, one I think is an interesting product, but I it is a, it's a very interesting story. Is well where there, there have been a lot of ups and downs on this journey and I think that for, you know, a lot of the times I'm talking to founders who are, you know, 10, 20 million in ARR and there there's useful lessons to learn there, but a lot of people listening to the show are at much earlier stage trying to get to.

[00:06:46] You know, the first a 100K in ARR or something like that. And I often hear from people, it's like, Hey, we wanna, we wanna hear more of the, the stories of, you know, people who are just a, you know, ahead of us rather than, you know, building sort of an eight or nine figure business. And with your story in particular, I think there's some really interesting lessons that hopefully we can distill down and help people listening to this kind of go away.

[00:07:12] And on the one hand, get some. Some maybe motivation or inspiration if they need it. And two, some ideas on, you know, when things aren't working, how do you turn things around, what do you do? And, and you know, some of the things that you've done over the last year to take the business that was effectively like, I think you said for a year, year and a half, almost two years, there was stagnation, there was decline, and then you turn things around and the businesses started growing again.

[00:07:39] So I think there's some really, really helpful, useful things to unpack there. So, I'm gonna try my best to make sure that we cover all those things. Let, let's start with where the business was founded. So I think it was 2017. Where did the idea come from?

[00:07:54] Brennan: Yeah, so I had, at the time I was kind of known for this course, you know, video course on email marketing.

[00:08:03] And one of the bonuses of this course was a zip file with a bunch of JavaScript in it that allowed people to put the JavaScript on your site. Tweak it a bit, and then you could use that to like change content in your website using jQuery you know, like change different headlines or whatever else, depending on data that you had in your email platform.

[00:08:23] So I was teaching people how to do things like, oh, email marketing done, done, right? One component of that is to segment your list. Oh, why don't we make it so if they're segmented by industry, maybe change up your sales page. Just have like testimonials for that industry, right? So I included. Some boilerplate code that they could use.

[00:08:41] The problem was that most people who bought my course were people doing email marketing and they look at a zip file full of JavaScript files and they're like, what is this? So one of the one of the customers of that course was a guy named Ankur Nagpal, who at the time owned a company called Teachable.

[00:08:58] And he's like, stop screwing around. Can you just make this a SaaS? And I was like, sure. Like that sounds great, but you know, money, time, all that kind of stuff. And he, he said, well, what, what, how about this? I will help organize some fundraising. You bring on somebody to work on it with you and yeah, let's make that happen.

[00:09:18] So that, that's exactly what ended up happening. Now we raised about half a million dollars in 2017 to convert a zip file of JavaScript into a, into a functional software as a service business.

[00:09:31] Omer: A great story. Yeah. I find a, I find a tweet from you where you said, like right before Right Message was Right Message.

[00:09:36] It was a bunch of custom JavaScript that managed to sync with drips API and, and I think it's, it's hilarious that Ankur was like. No, that's too hard. It's like, what wasn't he, if I remember, he, he was the guy who built the first version of Teachable, wasn't he?

[00:09:52] Brennan: Yeah. No, he, he was the owner and founder of Teachable.

[00:09:54] Yeah. Yeah. Well, so Mo, most of our customers were the ones saying the JavaScript thing was too hard. 'cause a lot of them were, again, people who were just. Using Drip to sense. They weren't web developers or anything like that, right? Ankur knew what it was, and he's like, what if you put a hosted front end to this thing that we like and set up Stripe behind it to charge people monthly?

[00:10:20] That sounds like a good plan, doesn't it? That's, so that's the origin story of the conversion, if you will, from a zip file to a software business.

[00:10:29] Omer: Did you have, when you raised that seed round, did you have any customers at that time?

[00:10:32] Brennan: Of the course? Yes. Of the, now we, we raised it before we had anything for the a sas.

[00:10:38] Omer: So why do you think you were able to. To raise that money. I mean, it, it wasn't huge, but it's not an insignificant amount of money to raise half a million

[00:10:47] Brennan: dollars. Yeah. You know, to be honest, we could have raised more potentially we, we had offers to do more, but we thought that's what we needed. And so why I think it helped, and again, this isn't a toot my own whatever thing, but I, I had a successful exit before.

[00:11:02] It wasn't a huge exit, but back in 2015, I sold my first business plan scope and. Since then and, and be before then I had, I, I've always been good at the whole like going to conferences and networking with the right people kind of thing. So the fundraising effort, honestly, like I didn't have a slide deck or I've never done any, anything like that.

[00:11:24] It was really just fired off at email to Nathan Barry, Hey, thinking of doing this un Rob Walling, hey, thinking of doing this un it's all people. I knew friends of mine, so it wasn't like, it was more of a friends and family kind of thing than me doing like I. You know, actual fundraising. So I, I, I did have an advantage there, I admit.

[00:11:44] But yeah, I mean, the fundraising part was relatively easy.

[00:11:48] Omer: Now I remember where the first time I came across you was, I think I heard a podcast more than 10 years ago talking about Planscope. It was like, yeah. It's like we're showing our age now. All right. So you, you raised this money and what, what did you do in terms of like, how did it, how long did it take to build the SaaS version of this, this JavaScript, you know, code that you had and, and you know, what was the journey to getting to those first 10 customers?

[00:12:19] Brennan: Yeah, so what we did was we raised the money and then I kind of went off and tried to use the money by building up a team. Right. So while that was happening, Shai was working on the initial kind of MVP, if you will, of the product. And we, it, I wanna say we, I think we incorporated in November of 2017. And I, we launched in about January, so it was about four months or whatever that is from like.

[00:12:47] Official incorporation with the money in the bank to selling something. So what we did was we I was kind of recruiting with the money, you know, using the money. And then also we put together a very simple kind of teaser page that was effectively a 500-word sales letter that had an opt-in forum at the bottom.

[00:13:06] And how we showed instead of told with this page is I wrote some custom JavaScript and with some like dropdown fields or dropdown forms where you could say like, dropdown of industry to whatever dropdown of email platform. You know, choose, convert it, choose drip, choose HubSpot, whatever. And it would change the text in real time as you did that.

[00:13:25] And that was kind of like our way of saying like, our tool will let you do that. Imagine if you knew this person is this, or this person says that they're looking at a sales page or a webpage or whatever, and this is what would happen. Obviously it wouldn't be as overt, but this is effectively what would happen.

[00:13:40] So we actually built up an email list of a few thousand people, I think it was about three or 4,000 people by the time we launched with that. And I, I kind of also while doing that, got invited to speak at a few different events and I couldn't point people to sign up for a product, so I just said, Hey, like, go over here and.

[00:13:58] Drop your email address and then I just kept emailing it once a week and kind of built a newsletter per, you know, around this kind of idea of personalized marketing. And it was nice 'cause by the time we launched in, I think it was January or February of 2018 we actually hit like 10,000 and MRR pretty much within a month I wanna say.

[00:14:18] And we did that by 'cause my background alongside Planscope was selling like courses. I used to have a company called W Freelancing where I sold a bunch of courses on freelancing and stuff. So I kind of treated the launch of the product, like I would launch a course, so there was urgency, there was like a, you know, a pricing scheme that if you bought launch week you'd get a good deal and stuff like that.

[00:14:39] So we actually had a nice, like burst of momentum. You know, we had this new team being developed and we, we actually were growing really nicely in like 20% month over month, and. I wanna say about a year into it, we were pretty much at about 35,000 in MRR, which I was really happy about, but then in reality, started setting it in and I realized I couldn't just keep doing like the whole like digital product launch strategy stuff for software business.

[00:15:06] And you know, the whole audience thing could only go too far. And a lot of what ended up happening was. We realized, okay, the tool, we built it, people were wanting it 'cause it's cool, it seemed interesting, but we didn't really have a lot of case study data to back it up with at the time. And on top of that the only way to personalize your website is if you have the segment data, like what industry someone in.

[00:15:29] And a lot of our customers were like, how do I get that information right? Like, you know, we're, we're kind of like, you know, if this than that, and word that than that. But they didn't have the api, so we were like, oh, you know, we, we kind of had this I don't know, this kind of issue where our, our, our rocket ship was, you know, starting to kind of falter.

[00:15:52] And yeah. From there we, you know, little after that we quickly had ran outta that money. Never got. That continuous 20% month over month that would've made it so we didn't, you know, run outta money. And we kind of reverted back to effectively being a operationally a bootstrap team with myself and my co-founder.

[00:16:11] And, you know, we were living off the money we had and we kind of pivoted the product to then also allow for a segmentation so we could satisfy the, if this part, but it, it really, it wasn't. It wasn't just growing the way we wanted it to and we were struggling. We were kind of lost in the wilderness for a bit and then we both kind of got de demotivated and we didn't go separate ways and we were still like tending to the product, at least the, you know, support system and stuff like that.

[00:16:39] But there wasn't no forward momentum. Momentum on the product. There wasn't momentum on the growth side or the development side or anything like that for years. And we just kind of like, you know, we'd, we'd shot up and then we kind of. You know, petered down over time. Okay, great.

[00:16:54] Omer: So let, I want to just, let's, let's kind of talk a little bit about that.

[00:16:56] So first of all, the getting to the first 10K in MRR and then getting to around 35K happened fairly quickly. But in many ways you had been working on this for much longer than that because you had been building credibility and authority in the email marketing space you had already been building an audience before you had been building this email list.

[00:17:25] So I think, you know, a, a lot of the times we, we discount that, but there's a lot of, you know, pre-work that went into laying the, the foundation, having this audience in, in place before you were able to get those types of results. So you raise the, the 500K seed round around 2017.

[00:17:46] Initially things are looking good. Revenue is growing. Your, your, you're inching your way towards, you know what, half a million in ARR. Then you start to run across some of these issues, you'd already hired a team, and so you have effectively a burn rate to, to worry about. And then is, is that basically like the thing that happened? Like you just got to the point where it was just like, okay, we've got this money coming in, but we're spending more than, than, you know, we are bringing in, we've gone through the money that we've raised, we can't afford to keep this team around anymore.

[00:18:22] Brennan: That's exactly what happened. Yeah. So we, you know, we, we were, we were making some money, but our burn was higher. Right? And we always thought, even like before, it's that quintessential kind of founder thing of like, before, before we run outta money, our revenue will grow as such, that it, it surpasses our burn.

[00:18:42] And that didn't happen. And I think the, the, you know, we, we hired fast 'cause we thought why have half a million dollars in the bank might as well use it. So yeah, I mean we were kind of a victim of our own success in a way, or at least early success. And yeah, we just realized, okay, so, you know, we kind of gradually paired back the team and then we just had to realize, okay, like, like both for shy and myself.

[00:19:09] We wanted to take out a livable salary. I mean, he was in North London. I was at the time of the us you know, we've got families and stuff like we can't do the ramen thing. So, you know, for that to happen, that meant once we dropped below about 20,000 in MRR, so we were, you know, gradually declining. 'cause a lot of that early growth was people getting a great deal.

[00:19:30] But then no one's gonna keep paying monthly if they don't act on that deal. Right? So. We didn't have the software at the time to really make it so a lot of people could really benefit from the product. 'cause they didn't have the segment data. So when we got under 20K, it's like, okay, that's when, like again, we're now just after product expenses, like the server and everything else and the, you know, all this stuff.

[00:19:55] Divide that by two and that's pretty much what HAI and I would need. So that's around when we were like, okay, we just need to go back to like just you and I live off this. Hopefully we can keep it stay, you know, steady and you know, even if we don't make any more anytime soon at least we're able to live off this.

[00:20:13] But yeah, then we both like, I think it was just the lack of like growth we were seeing and everything else and not really sure what we had to do next. It just, we both got very demo demotivated and. We just kind of like stagnated again for a while, and I pursued other things. He pursued other things.

[00:20:33] Product was still there. We had a core group of customers who were still benefiting from it and loved it, but we weren't doing much on the growth side.

[00:20:40] Omer: So you effectively keeping the lights on you, you're making sure that you can, you're providing support for the customers that you have. But you're not actively trying to go out and figure out, you know, investing in marketing or sales and growing the business or I guess evolving the product.

[00:20:58] And this was that period that went over for about, I think you said like a year and a half, two years. What changed then? Because that's a long time to go through feeling unexcited about a product and a business, and yet when. We talk about what you're doing now. I sense energy, enthusiasm. What made the shift?

[00:21:25] What got you excited again? What got you believing in this thing? Again, because man, I know if I'm like, if I personally like I'm down about something. I'm ruminating for like three days about it, it feels like forever just to turn myself around from that, right? Maybe it's just the way my brain works, but to kind of go through that for, for years and then, you know, turn, turn things around and get excited and find a reason to put your, your heart, your soul and energy back into this.

[00:21:57] Like, what, what was that process like?

[00:22:00] Brennan: Okay. So I think the way I'd describe it if you will, is that last year, so 2023, we kind of had this Hail Mary attempt to reinvigorate things, and that was to do the thing that is usually always a horrible idea, but we did it anyway, which is, let's start a new code base and dramatically simplify things and have it product, instead of it being a platform, which it is, just make it do one thing and do one thing really well and sell that. So we did this, and now we kind of ran this horrible issue where we had like two code bases to support all this stuff. It just, it didn't, again, that wa that didn't work, right?

[00:22:47] It didn't work the way we wanted it to, and at that point we were both like, okay, this, we need to either like. Just shut, shut things down and kind of effectively screw over the customers, you know? And at the time we had, what, 150, 200 customers who were using us and they kept paying. So presumably they liked using us and were getting benefit from the product.

[00:23:08] We shut it down. We sell it. Which selling a declining asset doesn't work usually that well or one of us buys out the other. I don't wanna, I don't wanna sell it. 'cause my last time I sold a business Planscope, the new owner drove it in the ground and it hurt me reputationally 'cause I was so tied to that product.

[00:23:28] I didn't wanna shut it down 'cause again, I knew a lot of these, you know, the customers I mentioned, these were like people I knew from my other 'cause I've got other income sources besides direct messages. I, I sell courses and I've got like a book and all this other stuff. These were kind of the, the, a lot of the fanboys, if you will of, of, of my stuff.

[00:23:45] And I don't wanna screw them over. So the only option was either he buys me out and tries to like, make it better or I buy him out. He didn't wanna buy me out. I was really wanting to buy him out. So that's the direction we went. And so yeah, I ended up basically cashing in a lot of my savings personally to buy out his equity, which again, as a declining asset, it meant just like if we were sold it on the open market.

[00:24:10] I got a, what I think was a good deal. And then, yeah, so I was like, okay, I bought this thing with my own cash, so what do I do with it? And the big change that happened I think was the realization and, and you and I talked about this kinda briefly earlier before we hit record, was that what if like we were getting rejected because people saw our, our thing as too confusing.

[00:24:33] And I knew we have an onboarding issue, we have like a product UX issue, we have all these issues. So I thought, okay, what if I just go to people who I would love to be a kind of a flagship Right Message customer and say, Hey, pay me to consult. You don't even need to use Right Messages, but you pay for Right Messages and you pay for my consulting fee, and I'll use this tool that for a lot of new people's, kind of confusing on your behalf.

[00:25:00] And make it work really well the way it's supposed to. So I did that and I did that again and again and again. And that's been brilliant because we've now, I have some of the biggest named creators on the internet using Right Messages and on their website, under our widgets it says, powered by Right Message.

[00:25:20] And we have all these people now we get people all the time 'cause they, they sign up and we ask a bit about like, you know, how do you know about us? And they're like, oh, Justin Welsh or, Matt Gray or Dango or Ben Meer or something. And it's these people with hundreds of thousands of people on their email list who make millions a year in sales.

[00:25:38] They're all now these great advocates of ours because they're, they're using us. So that to me has been the biggest, like I'm using that momentum to say, okay, now I can use this money and this momentum to make it so it is self-serve or really good, you know, good, good experience for self-serve customers. 'cause I don't want to be doing, I don't wanna do, like, if you remember bounce exchange, their model where they had like opt-in software that the only way to use their opt-in software was to hire the agency to do like the copywriting and the design work for their internal tool. I didn't want it to be this weird services company that happened to have an intellectual property under the hood.

[00:26:20] I wanted us always to be a proper, you go to the website, you sign up for a trial, you buy it, kind of thing. But I think this momentum over the summer that started and the case studies we're getting now like we just for Justin Welsh, we helped him increase. Overall conversions service course launch by 38%, which was hundreds of thousands of dollars now attributable to our software.

[00:26:42] And now we're like, we need to just shout this everywhere. And really, you know, so it's, that's been the big inflection point I think for us is I think my co-founder and I, when we started, we did the kind of quintessential, we don't wanna talk to people. Go to the website, if you wanna talk to us, we have a support email address.

[00:26:59] But I was much more willing now that I had my own money behind it to say like, I'm happy to sit on demos all day and just grind it out to sell people just so I don't look like an idiot in front of my wife and being like, Hey, I blew our, blew our retirement on, on buying this like, failing thing that I had started.

[00:27:16] Omer: So you went from a, a software as a service to software and a service.

[00:27:21] Brennan: But it's still not that. I mean, you can still buy it independently, but Yeah. Right, right.

[00:27:25] Omer: This, this was basically a way for you to it's basically a growth strategy and it, it helps you raise some additional money to, to, to fund the business.

[00:27:35] And, and you were, you were, you were telling me earlier that it's, it's basically the, the same playbook that Nathan Barry used with, Convertkit. And did he kind of, you know, him, did he kind of help you kind of with this or was, was that something that you had just seen?

[00:27:51] Brennan: I've known Nathan for years.

[00:27:52] I mean, he's an investor in Right Message and he and I used to do teach joint workshops and stuff before I, I remember getting a call one day from him saying, Hey, I'm thinking of starting an email platform. I was the first person to help him hire, I think one of his freelancers by betting their GitHub account.

[00:28:07] So like he and I go way back and, I remember seeing how he struggled a lot early on with, with ConvertKit. Like, I mean now it's doing what, like 2 million a month or whatever it is, or three. It's doing great now, but when you look at the, like, it was floundering at a few thousand a month for a while, and the, the big inflection point for him was he didn't partner up officially, but like he got in terms of like equity as far as I know, but Pat Flynn of smart passive income basically championed ConvertKit to his email list and got all the want to be Pat Flynn's to start using ConvertKit. So that's exactly kind of the playbook I'm using. 'cause what they did after that is then, you know, Nathan went to every peer of Pat Flynn and said, Hey, Pat's using ConvertKit, you should too.

[00:28:57] And then he did the same with like the fitness space and the food blogger space and all the stuff. And that's kind of what we're doing now is we're like a lot of the biggest players in the kind of pro space creator space are are now using us. And now I can confidently say like, you know, can name drop these people and say they all trust us and we're helping them make meaningful amounts of money.

[00:29:20] Here are some examples and case studies of it. And I, I think that's gonna be our ultimately our saving grace.

[00:29:25] Omer: So who was the first, lemme say that carefully ProSpace creator. One word that you signed on. Who, who was that and how did you go about getting that deal done? Because I've seen a lot of people try to do these things and fail miserably at it.

[00:29:41] So what did you do differently?

[00:29:43] Brennan: Funny enough, it was Pat Flynn and I knew him again. I mentioned conferences earlier because he and I played craps at a table in Vegas from at the after party of like a, or after, after conference we were both at. So I think like I'm, I've really tried hard to build up really good professional relationships friendships.

[00:30:07] I mean, friendships, I say professional, but these are all people I, you know, text and all that stuff. So, you know, these are people that I, I genuinely like as people. And yeah, I think like he, he was the first one. And the more recent ones, like I'm named Justin Welsh and Matt Gray and everyone else, those are all since the summer of 2023. So they're all kinda recent as, as of our recording. So Pat was the first one.

[00:30:30] Omer: I, I think I, I don't know Pat I've, you know, known about him for many, many years, but he's just, to me, he just seems like a genuinely nice guy. There was, there was a time back I remember like I went down to San Diego and I was thinking about, we were actually thinking about moving there at one point and I thought, who do I know in San Diego that could tell me about where, where to, you know, it's kind of good places for families to kind of move to and stuff.

[00:30:58] And I didn't know anybody and I thought, well, Pat Flynn's kind of knows about San Diego, right? So, so just randomly, I just sent this email to him 'cause I used to listen to his podcasts and stuff, and and I'll never forget, he actually replied and he listed out a bunch of communities and places to go and see and stuff.

[00:31:16] And it was like, he didn't know me from, from Adam and, and you know, he took the time to do that. So I think he's, he just kind of just, you know, showed me, he really is a, a very genuine guy. So I'm glad that he was also the…

[00:31:27] Brennan: well, their whole team, like, there's so many great people. SPI, I mean, obviously the face of it is, is Pat.

[00:31:33] But yeah, I mean, Matt Garland, who's, I think I the CEO now-ish. I wanna say like, I think Pat lately has been like more, he's not managing the team as much, and, and Matt's been doing that. Matt's a great friend too. I mean, they've got like, yeah, they've, they've got it all put together well. So good company, good brand.

[00:31:53] Omer: And then, so going to Justin, Justin Welsch was that just off the back of just saying, Hey, you know, we've, we've been working with Pat, or…

[00:32:01] Brennan: No.. So I think one of the things that really has helped a lot is I have a course, you know, that that earlier course used to be called Mastering Drip. I. I now have mastering ConvertKit.

[00:32:12] Right. And that's something I've had for years. And I got a DM from, from Justin once I wanna say like last spring or something where he was like, Hey I've heard good things about your course. I'm looking at the sales page. I don't have time to go through a course, can I just pay you? And it pretty much boiled down to that.

[00:32:28] And I think that's one of the, the things is like the course and the email marketing training for me, nicely and perfectly compliments like, it, it, it provides the, the why behind the how. Right? So I kind of look at it as like if, if this, if I'm, if the software's the pickax, the, the training is the map of where to go and swing the pickax, right?

[00:32:52] So I actually have found that that's something we haven't really talked about yet. But that's been a huge kind of component I think of all of this has been. Like I'm about to release a new course on segmentation, which I'm teaching How to Do It with Right Message or you could do it with Typeform or you could do it with Tally.

[00:33:09] But obviously with Right Message, I want you to use that. Oh, and by the way, if you buy the course, you get a credit equal to what you paid for the course for Right Message. So like there's a lot of I think there's a lot of room for not just going, like for me, if I'm just selling website personalization or segmentation software, you need somebody who already knows that they need that.

[00:33:29] Before they're willing to even, you know, commit to your product. Whereas if I do something that's more training where it's like, Hey, here's how to better think about better understanding your audience, what that means, what you could do with this, so on and so forth, and it's a video horse, then that's kind of the gateway drug in the Right Message for me.

[00:33:45] So my like whole grand plan for marketing is not gonna be doing like the traditional SaaS marketing stuff. It's gonna instead be, how do I build a lot of great training stuff and have these great. Big case studies that can push in the training as examples and teach it and all that kind of stuff, and have all roads lead to Right Message.

[00:34:03] And that's basically my plan for the year when it comes to growth.

[00:34:06] Omer: So you've got these, basically these pro creators that you're working with is helping you build a credibility. You're getting case studies. From those so people can now not just see the functionality of Right Message, they can actually see it in practice.

[00:34:23] Having powered by Right Message on these people's websites probably doesn't hurt either in, in terms of getting leads. Is there anything else that you're doing, or is, is it just that, that one thing that you are focusing on to. Just, just doubling down on that.

[00:34:39] Brennan: That's pretty much it. We're not doing any paid ads.

[00:34:42] We regrettably haven't touched our blog in like over a year, which I think is a big issue. 'cause I think a lot of people gauge is this thing still around by when the last blog post was. So I am planning on facing that. But it's really been a matter of bandwidth, honestly. And that's why a lot of, like, like you said earlier, the, the consulting revenue I'm using as a secondary fundraising tool to hire people who can help with that kind of stuff and make it so we can have fresh content and everything.

[00:35:07] Omer: It, it sort of reminds me of the way that you're positioning the course and then offering the subscription behind that. It reminded me of what Russell Bronson did with ClickFunnels.

[00:35:23] Brennan: I was just gonna say, I, I thought you might say that. Yeah. Was that an inspiration for you? Not really, 'cause I've, I've honestly never gone through Russell's stuff. I obviously know who he is, but I've never bought his book. I've never, I don't even know what, how ClickFunnels, I know it's, I know conceptually what it is, but I've never used it. But yeah, I mean there's probably a, a degree of that. I've always, weirdly enough, even though I, I'm in kind of the email marketing space, I've never tried to identify as an internet marketer.

[00:35:50] So I've kind of, you know, kind of shied away in a, in, in a weird way from the stuff Russell's doing. But yeah, I think there's probably a lot of overlap. 'cause that's, that was his playbook, his life. Teach secrets or whatever his book was called. And oh, and by the way, there's ClickFunnels. Yeah, yeah.

[00:36:09] Omer: No, I think that was, I think that was brilliant because, you know, everybody goes into SaaS and, and, and everybody thinks that there's one way. To, to sell software. And, you know, he came along and said, actually, I'm gonna sell an info product. And on the back of that, a SaaS product. And again, you know, what is it, you know, a hundred million whatever, plus business.

[00:36:30] It's, there's different ways to, you know.

[00:36:32] Brennan: I mean, even with ConvertKit, Nathan had written a book called Authority, which a lot of the early CU Convert customers came from that. So I think it can, it does make sense. I mean, it's not maybe for every SaaS, but if you've got, like, we do a, a sa, like the, the issue with the Right Message is we're one of the few software products that do what we do that are not in the enterprise space.

[00:36:56] So, you know, like our competitors are Optimizely and, and stuff, which. Again, we're not going after Optimizely type customers, so it's been a little of a weird thing for, we've had to really educate people in order to make a case for our product.

[00:37:13] Omer: When I first came across Right Message, it sort of seemed to be targeting like SaaS companies. So at least that's, that's the impression that I got. And that's not surprising where you get a lot of products and they say, well, we'll go after SaaS companies to start with because why not? Right? Just maybe help us understand why you didn't go down that path, why you chose these, these creators as your, your target market.

[00:37:42] What I'm trying to just understand is like how did you figure out what that, that niche was, what that target market was, and in, and, and where you could differentiate yourselves? And did you stay away from SaaS because the product didn't really work there, or because you realized it's gonna be much harder for, for us or for me now to, to clearly position this as, yeah. A differentiated or a unique enough offering that would get their attention.

[00:38:12] Brennan: Yeah. So early on, and even to agree to this day, we tried to cast a wide net. So we mistakenly thought, okay, anyone who does email marketing should use Right Message. So that meant SaaS, it meant e-commerce event.

[00:38:30] Plumbing companies, it meant creators or, or whatever. They weren't even called creators when we started, but that's the new name for them. And the, yeah, I, I think, I think the reason the creator thing has worked well for us has been with with SaaS typically, usually the extent of email marketing that they do is like product update emails, right?

[00:38:55] Like a lot of them aren't really doing a lot with thinking, okay, I need to have like nurturing sequences and I need to have like a weekly newsletter and, and I need to like think about audience building and like this kind of thing of like, you know, sending people from the email to the website back and forth and back and forth, whereas creators do think like that, especially the ones we're going after. You know, they're thinking, okay, I've got a portfolio of courses or high-end coaching offerings, and yeah, if I could just, you know, uncover a bit about somebody's psychographics, like why are they here? What are they struggling with? I can change the way I pitch my thing next time.

[00:39:33] To speak more directly to them and I think that makes a lot of sense to the kind of people we're going after now. And equally, I think that also works with e-commerce. I just don't know anything about that world. And I think that's actually a good thing. 'cause there have been some kind of right messaging kind of companies, but they're all targeting e-commerce now.

[00:39:50] So I'm like, okay, fine. Keep 'em there. Right. And so I think, and also to kind of close that out, I'm a, I'm a creator myself. I mentioned I, I've sold well over 5 million in, in. Digital courses since 2011 or however long I've been doing It started out as eBooks then shifted to video courses. I've run conferences before.

[00:40:11] I've, I've done the whole like, or used call info product business that has now shifted to kind of creator business. I've, I've done that and I, I still do that. So I kind of, I think, know that audience. Even though I'm a SaaS founder myself, I'm more. Aligned, I think with, with creators than, than other software businesses.

[00:40:34] Omer: And, and I, I think in many ways it's, that's a really important factor. Like when, when I talk to a lot of founders who are sort of early stages and they're trying to figure out, I. What their target market should be. And often the factors that they'll look at is, you know, the usual stuff in terms of do they have the problems, is the market growing?

[00:40:58] You know, all of these things. Can I retarget? Can I reach these people? I. But then the question I always ask is like, do you actually like working with these people? Like, do you wanna spend the next 10 years of your life working with these people? And, and sometimes really the answer is like, no, I don't.

[00:41:14] Right. And so it's like, okay, well find someone, find somewhere else.

[00:41:17] Brennan: And that's why I didn't go after an enterprise. I, I dabbled with enterprise accidentally. We had a. Big Fortune 500 who somehow found us. They reached out and I spent probably at least 20 hours on calls with like teams and this and that, like all these people.

[00:41:33] It never turned into anything, and they just wanted to do meetings all day. And I'm like, I, I just don't like, if that's granted yes. Maybe you hire that out. Sure. But I didn't want us, like at our, in our DNA always liked, I know this is kind of the often cited example, but I liked always what Basecamp, what they used to say about like, Microsoft can come and sign up for Basecamp.

[00:41:56] The max they're paying is 99 a month. They can't make us change our code base. They can't keep us, you know, up at, on Saturday building some custom feature that they need. Whereas when you have like a, you know, an enterprise company paying you a ton of money, I. That's kind of what they expect.

[00:42:12] Omer: Yeah. All right.

[00:42:14] We should wrap up. So let's get onto the, the lightning round. Got seven quick fire questions for you. Just try to answer 'em as quickly as you can. What's one of the best pieces of business advice you've received?

[00:42:24] Brennan: I think for, for me specifically right now, it's play up your, play up your strengths, because I think like, like a lot of founders, I always wanna up here bigger than I am.

[00:42:32] I've come to embrace, like hopping into my help scout inbox and sending a thing to a customer where in the signature, it's like Brennan Dunn founder, comma write message and people being like, wow, this is a, like from the guy who owns it. And it's actually not just a scripted like, you know, outsourced support thing.

[00:42:52] So I think like. Play up to the strengths that you are small and can do things that the bigger players can't do. It's a big good advice I'm trying to live by.

[00:43:01] Omer: What book would you recommend to our audience and why?

[00:43:03] Brennan: So, my favorite business book, it's a book called Badass. Badass, the subtitle is making users awesome. It's by Kathy Sierra, who is probably like, she hasn't really, she's kind of been hidden for the last few years, but it's the best book I've written on usability and UX. So highly recommended for everyone.

[00:43:25] Omer: What's one attribute or characteristic in your mind of a successful founder?

[00:43:29] Brennan: Focus.

[00:43:30] Omer: What's your favorite personal productivity tool or habit?

[00:43:32] Brennan: Having kids, they force me to work in a very constrained manner, which makes me very productive.

[00:43:41] Omer: What's in your crazy business idea you'd love to pursue if you had the extra time?

[00:43:44] Brennan: I'd love to build a really good email marketing platform. Because I, I have nitpicks with all the existing ones.

[00:43:50] Omer: What's an interesting or fun fact about you that most people don't know?

[00:43:53] Brennan: I have my pilot's license.

[00:43:54] Omer: You do? Wow.

[00:43:55] Brennan: I do. Yeah.

[00:43:57] Omer: And finally what's one of your most important passions outside of work?

[00:44:00] Brennan: Kind of boring now that I've got a 2-year-old, but I do when the summer, when the weather's nice as you, we were talking about earlier and the weather's nice here in England. I love cycling in the English countryside.

[00:44:11] I love just road biking and going through random villages and nice pub lunch at a 400-year-old pub or something like that.

[00:44:19] Omer: Yeah. We were just for, for people listening, like you and I were talking about how you are the, you are the American who's now in England and I'm the British guy who's now here in the US.

[00:44:31] Although I'm American now as well, so I have to, I have to play up both sides of the Atlantic now, so that's, that's great. So thank you so much for joining me, Brennan. It's been a pleasure to, to finally chat and, and share the story of Right Message. Looking forward to seeing what you continue to do over.

[00:44:50] The, the rest of 2024, as you're getting more and more momentum with this business and now basically kind of, you know, setting out on the new chapter as a solo founder effectively of the business this time. Also, we should talk about, you published a book last not that long ago. I think it was about five, six months ago, right. Which is called, This Is Personal: The Art of Delivering the Right Email at the Right Time. And I was thinking at some point like, you know, maybe we should get you back and just pick your brain and maybe just educate people about some of the things you teach in that book, because there are some really good best practices about email marketing.

[00:45:33] That everyone should be implementing and is not implementing today. And I won't mention any names but me and then also the, the course that you, you mentioned, so that's called Mastering ConvertKit and I think the website is what

[00:45:50] Brennan: Yeah, Create & Sell is like my digital products side of my world.

[00:45:54] It's a weekly newsletter and it's also courses.

[00:45:56] Omer: Yeah. Cool. So if people are interested in that, you can go and check it out over there. Great. Well, well thank you so much. It's been a pleasure and you know, enjoy your evening in, in England and I wish you the best of success with, with the Right Message.

[00:46:08] Brennan: Thanks so much for having me, Omer.

[00:46:09] Omer: My pleasure. Cheers.

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