Reflecting on the Journey from Startup Founder to Marketing Freelancer: Challenges and Insights
As entrepreneurs, many of us dream of transitioning seamlessly from building a startup to carving out a new professional path. I recently sold my company and decided to venture into marketing consulting—a decision fueled by curiosity, a desire to stay sharp, and a wish to support fellow founders. However, my experience has revealed that the road is far more challenging than I initially anticipated, offering valuable lessons along the way.
My Background and Motivation
Before diving into freelancing, I brought to the table extensive experience in growth marketing. I managed substantial advertising budgets—approximately $500,000 on platforms like Facebook and Google for a single product, and between $100,000 to $1 million across multiple funnels. Additionally, I built a YouTube channel that amassed over ten million views from scratch. With this background, I assumed transitioning to freelance marketing would be straightforward and manageable.
After selling my startup, I was eager to explore what else I could accomplish. Cash wasn’t a pressing concern, but I wanted to challenge myself, contribute to other founders’ growth, and remain engaged in dynamic marketing work. That led me to pursue marketing consulting as a new venture.
The Initial Challenges: Navigating Upwork
My first step was to seek clients through Upwork, focusing on US-based businesses. I crafted a professional profile and dedicated six months to landing my first gig. Despite numerous interviews and promising conversations, nothing materialized into a long-term contract. Eventually, I secured a $60-per-hour engagement for roughly two hours a week—helpful, but far from a sustainable income.
Building on Existing Networks
Parallel to my Upwork efforts, I tapped into my network of fellow founders. Some acquaintances offered me opportunities, which resulted in a $5,000-per-month retainer for approximately two days of work weekly. It was a promising start, providing stability compared to sporadic projects. I also took on a handful of short-term and one-off assignments, but my pipeline remained unpredictable—work would come in bursts, then dry up unexpectedly.
Surprising Realities of Freelance Marketing
My confidence that I could secure clients consistently proved to be misplaced. While I’ve successfully built and scaled businesses before, marketing freelancing involves a different set of challenges:
- Inconsistent Results: Achieving predictable outcomes across diverse clients is difficult. Even with expertise, I experienced strong results with around 60-70% of clients.
