Freelance to Founder

preston@millo.co

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This Changes Everything About Going Solo

June 15, 2026

Aisha Raman wants to know the single biggest lesson you learn when you first go out on your own. Preston and Meredith Cooley—copywriter, educator-turned-entrepreneur, and founder of Page and Purpose—have a lot of ground to cover. From the sneaky pull of shiny object syndrome to the surprising difficulty of managing your own time when no one else is watching, this conversation gets honest about the real growing pains of building a freelance business. If you're in the early days of figuring thi...

No Time to Freelance? You're Wrong. Here's Proof.

June 12, 2026

A Reddit question sparks a conversation that hits close to home for thousands of side-hustling professionals: a full-time teacher wants to know how to balance a demanding classroom career with landing and serving their first freelance clients. Preston sits down with Meredith Cooley—former 17-year educator turned full-time copywriter and teacher-to-freelancer mentor—to dig into the real, unglamorous work of building something on the side when your day job leaves almost nothing in the tank. Fro...

No Portfolio, No Problem… Here's Where to Start

June 11, 2026

Tharun is ready to take the leap into freelancing—but one question is standing between him and his first paycheck: how do you actually land that very first client? Preston and AJ Cassata from Revenue Boost share their own origin stories (a bagel shop, a school yearbook, a wave of cold calls) and break down the two simplest moves any new freelancer can make to get that first client through the door. No complicated funnels, no elaborate lead gen systems—just smart, human approaches that actuall...