The founder who rebuilt a personalization tool with no customer data: RightMessage

Brennan Dunn's freelance education business, Double Your Freelancing, had more than 50,000 email subscribers. Brand-new freelancers and business owners earning hundreds of thousands of dollars a year landed on the same course sales page. Their situations and reasons for buying were different, yet the pitch and testimonials they saw were identical. Dunn found the starting point for RightMessage in the work of reflecting those differences on the website.

He left his job in the mid-2000s to become an independent freelance developer, and as more developers joined him, he began running an agency. In 2011, he built Planscope, the project management tool he wanted for his own company. When running both businesses became too difficult, he left the agency to focus on software, but Planscope's revenue barely covered his personal living expenses.

To attract customers, Dunn started writing about freelance sales and business operations. He expected readers arriving through search to subscribe to Planscope, but they showed more interest in his business advice. He turned that attention into books and courses, and Double Your Freelancing grew from it. In early 2016, Dunn sold Planscope and focused on the education business.

Dunn recalled that selling a $300 course was easier than selling a $20-per-month software subscription. A project management tool only delivered value when customers changed their work habits and kept logging in. In his next business, he wanted to avoid that usage-habit barrier.

In the education business, he used what he knew about customers in the sales process. He tested changing email and webpage copy based on each reader's situation, then organized that method into a course. Companies such as Teachable and Gumroad hired Dunn to take on that work directly. In the course of being paid repeatedly to implement it, an opportunity emerged: turn personalization into a product marketers could configure themselves.

In 2017, Dunn teamed up with Shai Schechter, who had development and marketing experience. The two planned to keep their existing businesses while starting this as a small side project. They first decided to raise $10,000 through pre-orders, and met the goal within days. About six weeks later, they delivered a working product to early buyers.

Teachable, an early customer, also offered to invest. The two founders treated direct control over management and product direction as a key condition, and after discussions they raised slightly more than $500,000. They used the money to hire development and marketing staff. RightMessage started with both customer prepayments and outside investment.

RightMessage officially launched on January 23, 2018. On the pre-launch teaser page, the copy changed immediately when a visitor selected an industry or email tool. Customers experienced on the sales page the same capability they would be buying. In April 2019, the co-founder publicly reported monthly recurring revenue of about $30,000.

RightMessage connected to the websites and email marketing tools customers already ran. It changed headlines, testimonials, signup forms, and purchase offers using information about visitors. There was no need to rebuild a site or move an entire email system. Improving sales without disrupting an existing business was the product's practical appeal.

The behavior is easiest to understand through a concrete example. First-time visitors saw a newsletter signup, while existing subscribers were guided toward buying a course. Answers a visitor left behind, or prior behavior, could be reflected in the next screen and follow-up messages. The core idea was to keep using customer information, once captured, throughout the later sales process.

After launch, Dunn ran into problems he had not expected. Personalizing a webpage requires criteria and data for segmenting visitors, but many customers had neither. Even with a feature that swapped testimonials by industry, it could not work without knowing each visitor's industry. Customer information Dunn had taken for granted in his own business was not ready in other businesses.

The company expanded the product toward collecting visitor information directly. Marketers could learn customer interests or needs through surveys and quizzes, then vary the next questions and offers based on the answers. The collected information stayed connected to customer profiles and email tools for later use. RightMessage's scope grew to cover everything from customer data collection to segmentation and tailored offers.

The way the product was used was also an obstacle. Early customers wanted simple examples and settings they could apply immediately, rather than an editor that could change anything. For several months after launch, the company helped signups directly through demos, and its first hire was assigned to review customer setups and results. Even after delivering the tool, much work remained before customers actually used it.

Despite early growth, spending exceeded revenue. According to Dunn's retrospective, monthly recurring revenue rose at one point to about $35,000, then fell below $20,000. As investment money ran out, the team shrank, and the two founders kept the business alive while supporting existing customers. The period without new growth lasted about two years.

In 2023, they tried building a new codebase to simplify the product, but the burden of maintaining the existing product alongside it grew. In the end, the remaining choices were to close or sell the business, or have one founder buy out the other. Dunn did not want to wind down the business while customers still relied on the product. He put in personal funds to buy out his co-founder's stake.

The first thing Dunn changed for the recovery was how he sold. He focused on online education and content businesses with substantial revenue, and paired that with paid consulting where he personally handled personalization strategy and setup. As he won customers such as Pat Flynn and Justin Welsh, real usage examples accumulated. Dunn took on the setup burden customers had previously faced alone with complex configuration.

In an early-recovery SaaS Club interview, he disclosed about 250 paying customers and about $20,000 in monthly recurring revenue. At the time, operations ran with three full-time people and one part-time person. It was a business that had to cover payroll and product operating costs within subscription revenue from a few hundred customers.

Dunn then spent about a year rebuilding the entire product. Because he developed the new product while supporting paying customers on the old version, he could not ship new features to existing customers during that time, and his personal funds kept going in. He accepted the cost because he judged that old code was blocking product improvement. The rebuild proceeded while keeping the revenue-generating service running.

In an April 2026 interview, Dunn said monthly recurring revenue reached about $30,000 a little over a year after the relaunch. By then, he was running the business alone. He had reached the same revenue scale his early team once achieved, this time with a much smaller operation.

RightMessage's base revenue comes from project-based monthly and annual subscriptions. Starting from features that collect and segment customer information, the plans expand into website and email personalization, performance comparison, and automation. For customers, it is a tool for earning more revenue from visitors and subscribers they already have; for the operator, it is a business earning recurring revenue while that improvement work continues.

He also adjusted the market where he looked for customers. Dunn said the spread of AI search was pressuring course sellers' search traffic, and explained that he was broadening the target toward SaaS, direct-to-consumer businesses, and agencies. He had concluded he could no longer keep relying on the starting point his existing readership had provided.

Agency partnerships change sales and operations together. Agencies charge clients for personalization implementation and ongoing improvement, while RightMessage collects software subscription fees. Partners also earn a recurring 20% commission from the subscriptions of customers they bring in. The design spreads work once handled by a single founder, strategy and setup for every customer, across multiple specialist businesses. Dunn said that if he started over, he would build that sales channel first.

Dunn confirmed the effects of personalization directly, but underestimated the preparation other businesses needed to get the same results. What customers needed was information to segment visitors, offers to act on that information, and a way to actually finish the setup. Rebuilding RightMessage was the process of dividing that work across product features, implementation support, and partner services.