Freelance to Founder

Melissa wants to sell more consistently, so she asks Austin Church and Preston to walk through their actual sales process, step by step. They break down the handoff from marketing to sales, the deck that builds trust before a call even happens, and the recap email that turns a good conversation into a clear next step. The conversation lands on the habit most freelancers skip:...

Mark and a few others in Austin Church's Freelance Cake community keep running into the same wall: a client asks for a website or a logo, but the deeper conversation reveals they actually need a strategy first. Do you upsell them on the spot and risk scaring them off, or just deliver what they asked for and eat the extra work for free? Preston and Austin break down exactly wh...

Dave's agency works, for now. Pricing, delivery, client issues—it's all running through his head, and he's starting to feel it crack under the weight. Jesse P. Gilmore, founder of Niche In Control, joins Preston and Sabrina to map out exactly which systems to build first, from client onboarding to capturing the tribal knowledge that only exists in a founder's brain. Sabrina p...

Priya built her agency to escape the nine-to-five, but somewhere along the way, the business started running her instead. She's taking on every client that comes her way, terrified that saying no will kill her momentum. Preston, Sabrina, and Jesse P. Gilmore unpack the five-step framework for reclaiming time, documenting your work, and pricing based on value instead of hours—...

Marcus built his agency by doing everything himself, and it worked—until it didn't. Now he's got steady clients, recurring revenue, and a small team, but he's still making every decision, reviewing every deliverable, and jumping in the moment something goes wrong. Is that scrappy founder energy, or is it holding the business back? Preston, Sabrina, and agency coach Jesse P. G...