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Some founders build once and win. Most build, break things, and rebuild before they get anywhere worth going. Brennan Dunn belongs to the second group, and his story is the more useful one.
Brennan is the founder of RightMessage, a website personalization and segmentation platform that helps businesses stop treating every visitor the same. After a brutal stretch that nearly ended the company, he bought out his co-founder, rewrote the entire product from scratch, and relaunched. A little over a year later, RightMessage crossed $30k MRR and is still climbing.
Here is what he did, why it worked, and what you can take from it.
The Core Idea
Why Personalization Changed Everything for Brennan
Brennan's first company was Double Your Freelancing, a course and event business serving freelancers and agencies. He had a 50,000-person email list. He also had a problem that most founders never think to solve: every single visitor, regardless of who they were or what they earned, saw the exact same landing page.
A newcomer earning $40k a year and an agency doing $2M a year were looking at the same headline, the same testimonials, the same recommended package. Brennan, who came from a consulting background, knew this was leaving serious conversion potential untouched. The message matters more than the medium. Different people have different problems, and generic copy speaks to no one precisely.
So he did what most founders do before they have a product: he duct-taped something together. Custom code, Liquid templates in emails, and a lot of manual configuration. It worked. Conversions climbed noticeably. Companies like Gumroad and Teachable took notice and hired him to implement it for them.
That's when Ankur Nagpal, then CEO of Teachable, called with an offer to invest so Brennan could turn the solution into a proper SaaS. RightMessage was born out of a real problem Brennan had already solved for himself, which is exactly why it had early signal.
The takeaway: Brennan did not find a market and then build a product. He lived the problem, built a clunky fix, saw it work, and then productized it. That order matters more than most people realize.
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The year that almost broke him
The original RightMessage launched in 2018 with a co-founder, funding, and a team. The pitch was straightforward: swap website content dynamically based on data from your email platform.
The flaw revealed itself quickly. Outside of enterprise companies, very few businesses had meaningful segmentation data in their email lists. The tool assumed rich data that most customers simply did not have. Brennan and his team pivoted into the survey and quiz funnel space to solve that problem too, giving businesses a way to collect the audience data they needed before personalization could even kick in.
Then things got worse before they got better. The old codebase had accumulated enough technical debt that rebuilding was the only honest option. Brennan bought out his co-founder and spent a full year rewriting everything from scratch. During that year, paying customers received no new features. Brennan burned through savings. The emotional weight of running a business solo while supporting a family, with nothing visibly shipping, is the part that rarely makes it into founder stories.
He describes it plainly: financially and emotionally brutal. But it was the right call.
Growth Channels That Actually Worked
Existing Audience
Brennan's newsletter list pre-dated RightMessage. When the product launched, there was already a group of people who trusted his thinking. They presold before the product was finished. If you are not building an audience before you build a product, you are starting from zero every time.
Content That Compounds
Years of writing about email segmentation and personalization built trust slowly but reliably. YouTube videos showing specific use cases drove trial signups. This kind of content does not produce results in 30 days, but it does not stop working either.
Agency Partners
Agencies offer RightMessage as a service to their own clients. Brennan gets the MRR; the agency handles onboarding and support. Each activated partner brings in multiple clients without Brennan being involved directly. He wishes he had built this channel from day one.
Affiliate Program
Over 1,000 affiliates earn 20% lifetime recurring commission. Brennan admits he let this channel go quiet by not equipping affiliates with proper materials. He is actively reactivating it now with better case studies and creative assets.
The ICP shift nobody warned him about
RightMessage launched in 2018 targeting course creators and info-product businesses. That market has changed significantly since then. Traffic that used to flow toward educational content sites is being absorbed elsewhere. Brennan has had to reposition toward SaaS companies, direct-to-consumer ecommerce brands, and agencies. That transition is ongoing.
Repositioning an existing product toward a new customer type is harder than most founders expect. Your messaging, your case studies, your onboarding flow, your sales conversation, and your feature priorities all shift at once. It requires patience and discipline at the same time.
What he would tell himself at the start: focus on the agency and partner channel earlier. Not because it is the most exciting channel, but because it is the highest-leverage one for a solo founder. Partners handle implementation. They charge their own clients for setup. Brennan collects recurring revenue without being involved in every customer relationship.
Lessons for Solo Founders
- Build for a market you already understand. Brennan was the customer before he was the founder. He knew the problem because he lived it. When you are guessing what customers want, you are starting at a disadvantage.
- Start building your audience before your product. Even if you are a year away from launching, start writing and teaching now. The people you help today become the customers who trust you on day one.
- Validate demand before building features. Brennan has built things nobody asked for and delayed things customers were begging for. The second type of mistake is more common and more costly than it looks.
- Being a solo founder has real advantages. You can ship fast, make decisions without consensus, and change direction quickly. The constraint of working alone forces you to prioritize only what matters.
- Low-leverage work is the real threat. With a young family and limited hours, Brennan has had to become deliberate about compressing productive output into a few focused hours. The discipline around what not to do matters as much as what you build.
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What comes next for RightMessage
The near-term target is $40k MRR. Brennan notes, with some amusement, that the business is "unfortunately" more than profitable right now since it is just him and monthly expenses sit around $1,000. The plan is to scale the team as revenue grows to support it.
The agency partner program will be formalized further, with structured outbound recruitment replacing the current word-of-mouth approach.
On the product side, the focus is on giving RightMessage the ability to look at a site, understand the audience, and suggest personalizations automatically. The vision is a product that makes intelligent recommendations without requiring the customer to already know what to ask for.
The longer arc is straightforward: Brennan wants RightMessage to be the default answer whenever a business asks how to stop treating every lead the same. Whether that business is a SaaS, an ecommerce brand, or a service company, the answer should be personalization. He wants to make it easy enough that there is no reason not to do it.
Follow Brennan's Work
If this story was useful, Brennan shares his thinking on building and growing RightMessage regularly across a couple of places.
That is it for this issue. If you found this useful, forward it to one person building something. It costs nothing and might be exactly what they needed today.
Until next time.
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