How Ryan Robinson & Justin Welsh Scaled Freelancing into a Six-Figure Business

Let’s face it: as a freelance content marketer, you’re up against stiff competition. The field is overflowing with talented individuals vying for the same opportunities. But don’t let that discourage you! Countless freelance content marketers are not just surviving, but thriving in this competitive landscape. Want to know how they did it? In this article, we’ll dive deep into the journeys of five successful freelance content marketers, uncovering the strategies and mindsets that propelled them to the top. Get ready to be inspired and learn how you can apply their lessons to your own freelance career. Table of Contents Ryan Robinson: From Failure to a $35K/Month Blog Empire Ryan Robinson wasn’t an overnight success—he built his empire from scratch. After multiple entrepreneurial failures, he took a different approach: documenting his journey. What started as a side project—RyRob.com—soon became a go-to resource for freelancers and entrepreneurs looking to grow online. With 500,000+ monthly readers and 250,000 email subscribers, Ryan has mastered the art of SEO, affiliate marketing, and content monetization. His blog now generates $25,000 to $35,000 per month, proving that strategic content creation is a powerful business model. But he didn’t stop there—he co-founded RightBlogger, a suite of 80+ tools for bloggers, filling the gap he wished existed when he started. Beyond his blog, Ryan has worked with LinkedIn, Zendesk, Adobe, Google, and other Fortune 500 brands, helping them grow through high-impact content marketing. His expertise has been featured in Forbes, Fast Company, Business Insider, and Entrepreneur. Here are some of his most impactful insights: “It takes time to make money blogging. In fact, it takes a good deal of time to make money blogging.” “You’ll Make Mistakes with a New Blog and That’s Okay (in Fact, it’s Vital)” “Quality is Much More Important than Quantity with a New Blog.” Justin Welsh: From Corporate Burnout to Million-Dollar Solopreneur Justin Welsh wasn’t just another corporate executive—he was a high-performing leader in the SaaS world. Over the last decade, he played a pivotal role in scaling two companies past a $1 billion valuation and helped raise over $300 million in venture capital. His expertise in growth, sales, and strategy made him a powerhouse in the startup ecosystem. But despite his impressive achievements, something was missing. By 2019, burnout had taken its toll. The relentless grind, high-pressure environment, and constant chase for the next milestone left him drained. He realized that while he was helping companies succeed, he wasn’t designing a life that fulfilled him. So, he made a bold move—he and his wife quit their high-paying jobs, packed up their lives, and moved to the Catskill Mountains in New York to start fresh. Rather than jumping into another corporate role, Justin decided to build something of his own. He turned his knowledge of business, marketing, and personal branding into a thriving one-person business. Starting with LinkedIn, he crafted a strategy of sharing actionable insights, industry wisdom, and personal reflections—consistently and authentically. Over time, he grew his audience to over 700,000 followers and became one of the most influential solopreneurs on the platform. But he didn’t stop at content creation. Justin monetized his expertise through digital products and coaching, focusing on simplicity and scalable systems. His courses, including The LinkedIn Operating System, have helped thousands of professionals build their brands and businesses. His model? One niche. One clear problem. One systematized solution. No unnecessary complexity. Justin’s Key Lessons for Solopreneur Success: “You should have a very “long game’ mentality.“ Start a side project. Build it to 60% of your salary. Then go all in.” “The solopreneur playbook is simple: One niche. 1,000 true fans. One solvable problem. One systematized solution. Everything else is just overcomplication.” “The most successful people I know don’t have better ideas. They have a higher tolerance for discomfort. They’re simply willing to sit in the mess longer than everyone else.” Miranda Marquit: From $5 Articles to Six-Figure Financial Writer Miranda Marquit’s journey as a freelance writer didn’t start with six-figure clients or prestigious bylines—it began with $5 keyword-stuffed articles for content mills. Like many freelancers, she started at the bottom, taking low-paying gigs just to gain experience. But she knew she couldn’t stay there. Instead of grinding away for pennies, she made a strategic decision to specialize in a lucrative niche: personal finance. At first, Miranda wrote for independent bloggers, gradually building her portfolio and credibility. As her expertise grew, she transitioned into corporate clients—banks, fintech firms, and investment companies that valued her deep knowledge of finance. With each step, she increased her rates, moving away from the content mills and into the world of high-paying clients. But it wasn’t just her financial expertise that set her apart—it was her commitment to quality, networking, and long-term relationships. Miranda actively engaged in finance writing communities, built strong professional connections, and positioned herself as a thought leader in her niche. Over time, she secured premium clients, established herself as a go-to financial writer, and turned her freelance work into a sustainable six-figure career. Miranda’s Takeaways for Aspiring Freelance Writers: “There are so many great opportunities, and I’d hate for people to be afraid to try just because they feel they don’t have the time.” “My favorite moments are when readers email to let me know that something I wrote taught them something new or encouraged them to think about money in a different way.” “Try to make those personal connections and, most of all, try to be useful. That personal connection really does make a difference.” Bani Kaur: The Fearless Freelancer Who Faked It Until She Made It “Can you write for our SaaS?” The voice on the other end asked. Without hesitation, Bani Kaur replied, “Yes, of course.” The truth was, she had never written about SaaS before. Up until that moment, her writing experience was rooted in architectural publications. But instead of letting inexperience hold her back, she hung up the phone and immediately Googled, “What is SaaS?”—and so began her crash course into the tech industry.