Scaling a Freelancer Platform: Solving the Double-Sided Marketplace Problem

Marketplaces are notoriously hard businesses to run and build. We would know. Running a marketplace means constantly balancing two sides—the buyers and the sellers. If one side struggles, the whole thing falls apart. Chris M. Walker has cracked the code of this delicate dance. As the founder of Legiit, a thriving freelance marketplace for businesses, agencies, and SEOs, he’s learned how to make both sides of the equation work in harmony. In this episode, we sit down with Chris to unpack the operational challenges of running a double-sided marketplace. He shares the lessons he's learned, the mistakes he’s made, and the strategies that helped Legiit become a trusted platform for freelancers. One of the biggest takeaways? The power of company culture. Scaling a business means founders can’t do everything themselves. Chris believes a strong, well-aligned remote team is the key to keeping things running smoothly—even when you’re not in the room. He prioritizes culture to make sure his team is not just working but thriving. If you're growing a business, managing a remote team, or thinking about starting your own marketplace, you won’t want to miss this conversation. Tune in to the full episode to learn more! Topics Discussed in this episode: Chris’s origins story and how he ended up creating Legiit (02:38) Dealing with the double-sided marketplace problem (07:09) How Chris attracts customers to Legiit (09:39) Using courses as a loss-leader product (13:58) Chris breaks down Legiit’s marketing funnel (16:03) Chris’s experience at the India SEO conference and the power of conferences (21:03) How Chris structures and manages his team (27:52) Chris’s advice for managing remote teams (32:09) How freelancers can get clients and how to adjust to a larger client base (36:35) Chris’s thoughts on the impact of AI and the future of SEO (44:06) Mentions:  Empire Flippers Podcasts Empire Flippers Marketplace Create an Empire Flippers account Subscribe to our weekly newsletter Legiit Chris’s Facebook Chris’s YouTube Sit back, grab a coffee, and learn how to grow a marketplace and build an efficient remote team!