Double Your Freelancing

Brennan Dunn spent years building a successful Ruby development agency in Norfolk, Virginia, growing it to 11 full-time employees and "a few million a year in revenue." But watching friends build SaaS businesses gave him the itch to create recurring, scalable revenue. In 2012, he exited the agency and launched Planscope, a project management tool built for small agencies and freelancers like himself.

"I really struggled to sell it. I really struggled to get it in front of people," Brennan recalls. He had a product but no distribution.

Desperate to find customers for Planscope, Brennan discovered content marketing. He started writing blog articles about freelancing—topics like pricing, getting clients, and pitching services—that had nothing to do with project management software but spoke directly to his target audience's actual pain points. The response was immediate. "I started getting testimonials and people writing in who I'd never even talked to saying you've literally changed my life."

This unexpected success led him to expand: first an ebook (which he was skeptical about as an engineer), then paid courses and workshops. By 2016, Double Your Freelancing had attracted over 10,000 customers and 40,000 engaged followers. The content business had become so dominant that maintaining both it and Planscope was impossible. Brennan made the call: he sold Planscope to focus entirely on Double Your Freelancing.

The core insight driving Double Your Freelancing's success was understanding that freelancers aren't searching for "pricing courses"—they're searching for solutions to frustrations like "How do I stop underpricing myself?" or "How do I get more clients?" Brennan weaponized keyword research and SEO to intercept these conversations.

But his real innovation came in personalization. Rather than static content or generic marketing, Brennan treated his WordPress blog like a SaaS application. He embedded JavaScript, CSS, and local storage tracking to personalize everything based on visitor behavior. If someone read multiple articles about proposals, they'd see a call-to-action about closing more proposals. The email course they received would be customized. The sales page for his paid course would adapt its copy based on whether they were a solo designer, a developer, or an agency owner.

"I've made the niche the funnel. I've made the niche the marketing, the copy, and everything else," Brennan explains. It's a best-of-both-worlds approach: keep the product broad, but make the marketing feel individually crafted.

Double Your Freelancing generated $900,000 in revenue with Brennan running it almost entirely solo (plus one full-time assistant and occasional freelance help). He's on track for $1.5M+ this year. The business is heavily automated—Brennan's stated mission is that "if I were to go into a coma this should still work."

Success with content marketing has led him back to software. He's launching WriteMessage, a website personalization SaaS that automates the manual work he's been doing on his own site. It's his third distinct business model—agency (high-touch, transactional), SaaS (recurring, habit-forming), and content + courses (high-volume, transactional). Each taught him something critical about scaling, which he's now synthesizing into his next venture.