An Interview with Brennan Dunn from RightMessage

Recently, I got a chance to interview Brennan Dunn who has been my mentor when it comes to email marketing, marketing automation and using data properly for marketing.

He also runs RightMessage – a tool to segment and personalize websites and landing pages. A huge thanks to Brennan for doing this interview and a special thanks for the long and insightful answers.

1. Tell us a bit about yourself, Brennan.

Hey! My name is Brennan Dunn, and currently I run two companies: RightMessage and Double Your Freelancing.

In the mid-2000s, I quit my day job to go full-time as a freelance developer. This ended up evolving into a loose collective of other developers, and then eventually matured into a proper brick & mortar agency.

In 2011, I started a side project called Planscope, which was the project management tool I always wanted for my agency. I found it hard to run both an agency and this new startup, so I quit the agency to go full-time on Planscope… which was a mistake!

Planscope, as a company, was never super successful. It did well enough, but it barely supported my own personal expenses. And getting customers was hard, especially to someone like me who was relatively new to low-touch sales and marketing.

So I did what any SaaS owner who was paying attention to online marketing best-practices did: I started creating content.

I was pretty decent at consulting (thanks to the experience that came with scaling an agency), so I started writing as much as I could about how to freelance. The hope was Google would send traffic to this content and that traffic would convert into Planscope customers.

It didn’t work as well as I thought, but I did end up with a pretty healthy list of people who wanted advice on consulting and freelancing.

A few books and courses later, and Double Your Freelancing – what was the content marketing arm of Planscope – was now doing really well, and in early 2016 I sold Planscope to go all-in on DYF.

Part of what helped me grow the business was how I was using personalization to increase opt-ins and sales. This would ultimately lead to RightMessage, but for the last few years I used DYF as a sort of petri dish for trying to figure out how I could make as much money as possible without needing to buy traffic or hire a team.

While running DYF, I shared a lot about what I was doing to grow the business. I was pretty vocal on Twitter with how I used automation, personalization, and essentially translated my skills as a developer to improving how I marketed and sold my products.

And in 2017, I partnered with Shai Schecter to start RightMessage, a software company that would help marketers better personalize both their content and their calls-to-action.

2. What’s the biggest mistake you see that freelancers make and what’s your advice/recommendation to them?

They think clients hire them for their abilities as a coder, designer, etc. Clients hire you because they need a business problem solved, and they’ve determined that someone like you could help them solve it. That’s it.

The best freelancers know that their job is to solve business problems, and they focus all their attention (in how they promote and pitch themselves) toward that end – rather than touting their technical abilities.

3. For someone who wants to start freelancing what’s your advice?

Build your network, get a handful of clients on a monthly retainer or subscription offering, get your current employer to turn into your first client, and have a 6-month emergency fund in place.

4. Tell us about your journey from DYF to Mastering Drip to RightMessage. How does it feel to run a SaaS company with $25k+ MRR?

OK, so this is a lot of fun to talk about…

Rather than jumping head-first into another software company, I did a few things right in retrospect:

Personalization had worked well enough for me, and I was getting good results. And what I was tweeting was getting me on the radar of companies who wanted something like what I’d done for my own business. This led to almost a dozen small consulting projects where I’d basically pitch clients on why they needed personalization and what it would do for them. These clients paid a lot of money for a bespoke solution, and it helped me get comfortable at selling personalization.

Then I created Mastering Drip, a course on automation and personalization. I took what I learned selling automation/personalization consulting and applied it to a standalone sales page that didn’t involve me needing to individually pitch anyone. This worked well, and over 400 people have bought the course. This helped me get familiar with selling personalization-as-a-concept at scale.

Then, and only then, did I reach out to Shai and ask him to work with me on building RightMessage.

And the work I’d done – selling personalization consulting and a course – gave us a huge head start out of the gate.

5. Why RightMessage? How much you think it’s going to change the game?

If anything, it’ll make marketers more intentional when it comes to using their website and their content to pitch products or services. Every company seems to tout “the right message to the right person at the right time!” but almost all of these companies are merely giving lip service to personalization (it’s as bad as AI!)

I think for companies that have a portfolio of products, and who want to be able to reposition how a product is described on-the-fly, RightMessage is going to change the game for them.

Funny enough, none of this is new. Any salesperson worth their salt personalizes the way they pitch people, and essentially make small adjustments to how they sell based on who they’re speaking to and what they’re looking for.

6. You have always put more efforts on automation than many marketers out there. You even created the Mastering Drip course. Did it lead to the RightMessage?

It did! Kinda…

Like I mentioned earlier, what really led to RightMessage was getting so many complaints from Mastering Drip customers. “I’m a marketer! How am I supposed to do this personalization stuff? What am I supposed to do with all this JavaScript stuff you keep talking about?”

This feedback led me to partnering with Shai, which ultimately led to RightMessage becoming a standalone company.

7. You have created RightMessage. Joanna has created Airstory. Neil purchased and retooled UberSuggest. Do you think this is going to be trend across [course] creators? Do you see more course creators making tools?

I’m cautiously optimistic. I think it’s good that the people who create software have experience teaching the problem domain that their software addresses. I’ve used plenty of software, like webinar apps, that leave me thinking: “Has the founding team ever actually run a webinar?”

I think having experience in teaching, and packaging that into implementation, is a good thing.

That being said, there are a lot of course-creators-turned-SaaS-owners who obviously skimped on the technical implementation. It seems they were attracted to the recurring revenue aspect of software, but haven’t internalized that they’re running a software company, and that software requires a degree of engineering oversight that so many of these apps just don’t have. (Not going to name names here.)

8. Your emails are something I don’t miss reading, and I love them. How do you write such good emails?

I try to make most of my broadcast emails a reply to someone who replied to some other email of mine. It’s easier to write something good when you know who you’re writing for and what they’re asking.

Writing, like anything, is a learned skill. In high school, I spent every summer at a creative writing summer camp at the University of Virginia. College was spent writing essay after essay at a liberal arts college in Maryland. And a few years after college, I was writing weekly articles on freelancing. That continuity and cadence has helped tremendously, especially with writer’s block.

9. Moving forward, what do you think is going to be the essential skill for the marketers?

I think every marketer should learn how to do some basic coding. Having an analytic, “if-this-than-that” mindset is the ultimate marketing superweapon.

I also think there are way too many marketers that are too focused on quantitative metrics, and think getting qualitative data, feedback, and voice-of-customer language is the responsibility of the stakeholder or somebody who isn’t them.

10. Will RightMessage have its own in-built email marketing platform in the future?

I can’t see that happening, no. We don’t even house our customers’ data. Our job is to be a bridge between our customer’s websites and their email marketing databases / CRMs.

Deepak: Thanks a lot Brennan for your answers. I’m sure the readers of my blog would have enjoyed the answers. All the best for your business and looking forward to learn more from you!

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