Freelance to Founder

Omar's business is growing, and so is his workload. His longtime clients love working with him, which is the problem. As he builds Vision Craft Studios into an agency, every project still runs through him, because handing it off feels like breaking a promise. Preston sits down with Christine Olivas, founder and CEO of No Single Individual, to talk about trusting subcontractor...

Layla built Bright Horizon Media from the ground up, and now her social media agency has a team and real momentum. Her next challenge is splitting the revenue: what's fair to her subcontractors, what's fair to her clients, and what's fair to her as the owner? Preston and Christine Olivas take on the "is this cheating?" guilt many agency owners feel. They cover pricing strateg...

Christine Olivas has a calendar that won't quit and a pile of projects she keeps saying no to. The obvious move is to hire, but she knows the wrong hire at the wrong time just creates a bigger, more expensive mess. Preston and Christine walk through how she went from solo freelancer to a 24-person team: the signs that show it's time, the first role worth filling, and the trap...

CodeCrafter's skills are solid and his work speaks for itself, but he keeps holding back. Charging more feels presumptuous, and calling himself an expert feels like a lie. Preston unpacks why so many talented freelancers stay stuck waiting for a confidence that never shows up on its own. This episode redefines expertise from the client's point of view and gives you a practica...

Garrett is a 30-year-old nonprofit consultant doing great work for a seasoned consultant. The problem is that almost nobody knows it's his work. The more he delivers, the more his name fades into someone else's brand, and the line between partnership and being swallowed up gets blurrier every month. In this solo episode, Preston helps Garrett weigh three paths: merge, stay, o...