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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. 

Bani dove headfirst into research, mastering industry jargon, studying competitor content, and adapting her writing style to match the demands of the field. Her ability to learn quickly and deliver high-quality work turned that single opportunity into a full-fledged freelance career. Over time, she went from being an outsider to a sought-after SaaS content writer, working with over 20 globally recognized brands. 

 Bani’s story is proof that success isn’t always about what you already know—it’s about your ability to learn, adapt, and confidently take on challenges. 

Beyond technical skills, Bani understands that thriving as a freelancer isn’t just about writing—it’s about collaboration, relationships, and community. She believes that surrounding yourself with the right people—whether clients, fellow freelancers, or mentors—has a direct impact on creative success. 

Bani’s Words to Live By: 

“I’ve wanted to be a writer since I was 5. When I got paid for my first piece, I was over the moon (and oh-so-determined to make a career out of it). And I did. And it’s no longer enough.” 

“What I’m getting at: being a team player is as important to my professional identity as being a good writer.”  

“One thing that’s crucial for my creativity and job satisfaction is people. I produce my best work whenever I’m surrounded by empathetic, diverse, and motivated people. And writing alone can be lonely.” 

Vlada Korzun: The AI-Driven Content Strategist

With over four years in B2B content marketing, Vlada Korzun has worked on international projects in both freelance and full-time roles. Currently, she creates content for a SaaS company serving sales professionals while mentoring aspiring writers and refining her expertise in data-driven content strategy. 

Unlike many writers who see AI as a threat, Vlada embraces it as a tool to enhance creativity. She doesn’t let AI take over the writing but uses it for research, structuring, and trend analysis, blending AI-driven insights with human expertise to create content that is both SEO-friendly and engaging. 

A key part of her strategy involves tapping into real audience conversations. By actively exploring Reddit, she uncovers valuable insights straight from users discussing their pain points, needs, and industry trends. Instead of relying solely on traditional research, she analyzes online discussions and engagement patterns, using platforms like Reddit to validate content ideas and craft highly relevant, audience-driven pieces. Her ability to stay ahead of trends and understand audience needs is what truly sets her apart. 

Vlada’s Thoughts on Writing & Growth: 

My observation: Low-priced writers have little motivation to research and think deeply. They need to churn out “OK” articles to make ends meet.” 

“You don’t need to have big brands in your CV or 100,000 followers to be invited to a podcast.” 

“You aren’t perfect for everyone. But that doesn’t mean you are a poor performer. Getting negative feedback – learn and soak up, but also protect your inner child. It will save your confidence while learning.” 

Cultivating Success

Thriving as a freelance content marketer requires more than just strong writing skills—you need a strategic mindset, adaptability, and a deep understanding of the digital landscape. The most successful freelancers continuously refine their craft, stay ahead of industry trends, and position themselves as valuable assets in a competitive market. 

Search Engine Optimization (SEO) 
A solid understanding of SEO is essential in today’s content landscape. Gone are the days when keyword stuffing could game the system. Search engines now prioritize content that engages, informs, and provides real value to readers. To stay competitive, content must be formatted for readability, optimized for mobile devices, and strategically structured with relevant keywords while still maintaining a natural flow. Successful content marketers understand that SEO isn’t just about rankings—it’s about delivering content that people actually want to read. 

Content Strategy  
Beyond SEO, a strong content strategy is the backbone of a successful freelance career. Posting consistently, engaging with audiences, and planning content with clear objectives in mind ensures that your work stands out. More importantly, personal storytelling and authenticity help create deeper connections with readers. People engage with content that feels genuine and relatable, so sharing experiences, challenges, and behind-the-scenes insights makes your writing more memorable. Quality always beats quantity—each piece of content should serve a purpose, whether it’s to educate, entertain, or inspire. 

Work in a Niche 
Another key to long-term success is specialization. While generalists can cover a variety of topics, freelancers who become authorities in a specific niche are far more likely to attract high-paying clients and build lasting relationships. Businesses prefer writers who understand the nuances of their industry, whether it’s finance, tech, health, or lifestyle. Establishing expertise doesn’t happen overnight, but consistent learning, networking, and contributing to industry discussions can help position you as a go-to expert. Freelancers who immerse themselves in their niche by blogging, engaging in LinkedIn discussions, or joining industry groups build credibility faster and attract better opportunities. 

Stay Curious
Lastly, adapting to trends and staying ahead of industry shifts is crucial for sustaining success. Content marketing is an ever-evolving field, and those who stay informed gain a competitive edge. Reading widely, analyzing high-performing content, and experimenting with new formats helps freelancers refine their approach. Incorporating trending topics, viral discussions, or cultural moments into content can also make it more engaging and shareable. By continuously learning and evolving, freelance writers position themselves as indispensable assets in an increasingly crowded market. 

 
Your Freelance Success Starts Now 

We’ve explored the stories of five successful freelance content marketers and uncovered the key factors behind their success. Now, it’s your turn to apply these lessons. Use AI as a tool, stay adaptable in a fast-changing industry, and develop the business acumen to position yourself as a high-value freelancer. 

Starting a freelance career isn’t easy, but you don’t have to do it alone. Let us handle the financial and operational details so you can focus on what you do best. Schedule a call with us today to see how we can support your freelance journey.

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