From Freelancing To Running An Agency: Alexander's Story

From dealing cards under casino lights to crafting content for tech software brands, Alexander Boswell’s journey has been unconventional. But long gone are disheartening former clients who micromanage and underpay.

He’s built a thriving content business that’s gone from the gig economy grind of Fiverr and Upwork projects to working with brands like Shopify, Vimeo, and Descript. And he’s just getting started — he’s laid the foundations for his own agency, supported by solid Notion infrastructure and a Super site.

Scaling business model to match ambitions

Isn’t it fascinating to look back at where you started versus where you are now? A few personal articles on Medium, and suddenly, you’re building a Notion page for your agency’s standard operating procedures (SOPs). But it was those first blogs that gave Alexander a taste of a career in content.

With cautious optimism, he landed his first client on Fiverr, charging $150 for the project. This was a solid start, though Fiverr’s fees and taxes knocked his take-home pay down to around $100.

“The client was quite micromanaging, constantly requesting changes, leading to scope creep,” says Alexander. “Knowing that other freelancers had different experiences, I joined the freelance writer community Peak Freelance.”


During this time, his confidence and professional growth soared. The next step was building his first website. He used WordPress and the Elementor plugin, drawing from his experience with personal blogging in 2009.

However, despite optimizing it through Google Console and PageSpeed testing, the site was painfully slow. The bloated templates, large images, and unnecessary code were likely the culprits. The overly flashy design with interactive elements probably contributed to the sluggishness.

“As someone who despises slow websites, I knew I needed to find an alternative,” he says.

That’s when he stumbled upon Super. Already a Notion user, it was a perfect match. His Super site started ranking soon after launch, helping him land big-name clients like Vimeo. As his portfolio grew, Alexander found B2B software, MarTech, and AdTech to be the perfect niches for him.

“Looking back to when I first started writing on Medium, I didn’t imagine freelance writing would involve working with tech companies like this,” Alexander says. “I likely envisioned writing for lifestyle magazines and publishers that would appear in my feeds.”

But the idea of entrepreneurship and eagerness to build were always there. And, after two years of freelancing, he noticed other freelancers transitioning to an agency model, making Alexander question the trajectory of his writing business. “As fulfilling as it was, the routine started feeling monotonous,” he says.

“That’s when I became inspired by companies like Beam and the work they produce. I aspired to create and be part of that kind of environment, working with a team of people, collaborating, and succeeding together. While I still wanted the autonomy of working for myself, I missed the team dynamic from previous jobs.”

The solution was simple. It was time to build an agency of his own, SaaSociate.

“The idea of handing over control of the work to someone else is daunting for me. It’s not about authority but about building trust and a good working relationship with the person,” Alexander says.

“I’m torn between onboarding a freelancer first or gaining more clients initially. If I hire a freelancer too soon without enough work, they may be unsatisfied. But if I take on too many clients before having support, I’ll be overwhelmed and may rush into freelancer relationships without proper vetting.”

Still, he’s been building his agency’s Notion infrastructure, with spaces dedicated to content, operations, and resources. This groundwork brings Alexander a step closer to his vision of focusing on the roles he truly thrives in — people management and workflow organization.

But Alexander’s not giving up the pen entirely. Although he plans to assign more writing duties to his team, he still wants to stay hands-on with his favorite long-term clients.

“While part of me sometimes pines for the simplicity of being told what to do in a job, I crave the stimulation and challenge of running my own business,” Alexander says. “Having experienced good and bad management styles, I’ve gained valuable insights into what works and what doesn’t.”

Alexander is in this for the long haul. While his entrepreneurial path continues to evolve, the destination is clear: building a creative, team-driven environment where he can blend leadership with his passion for marketing and technology.


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