Say Goodbye to Anxiety with This Deadline Trick

Dana runs her freelance business hoping to stay organized without sacrificing the freedom she went into business for in the first place. Preston and Austin Church share the exact project brief template, planning ritual, and weekly status report habit that keep clients happy and deadlines met, then dig into the bigger question underneath it all: what freedom actually looks like when you're the one responsible for every deadline. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Amy has been posting consistently on LinkedIn, but the algorithm keeps shifting and her feed leaves her frozen, unsure where to spend her limited time. Austin Church breaks down three practical habits—targeted commenting, building a dream client list, and messaging profile visitors—that turn a few minutes on LinkedIn into real client relationships. Preston and Austin share the exact bookmarking system, comment frameworks, and DM approach that keep the algorithm working in your favor instead of against you. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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: consistent, personalized follow-up that turns hesitation into a decision. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 when to introduce a strategy engagement, how to phrase the offer without sounding like a bait-and-switch, and the four pricing containers — from a quick clarity call to a full strategy sprint — that let you charge for expertise you've been giving away. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 pushes the conversation further, asking what systemizing looks like when your service is literally yourself. It's a practical, no-fluff roadmap for anyone ready to stop being their business's single point of failure. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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—plus why getting selective about clients is what actually lets an agency grow. This episode is a wake-up call for any founder who's traded one kind of burnout for another. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Gilmore break down the exact framework for figuring out what to eliminate, automate, and delegate—and why the shift from self-employed to business owner starts with knowing your unique ability. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Lena is staring down her first tax season as a freelancer and wants to know whether she should hire an accountant right away or figure it out herself. Preston and Austin Church share the expensive lessons they each learned the hard way — including a mistake that cost Preston tens of thousands of dollars — and lay out exactly when it makes sense to bring in a CPA versus when you can DIY. They dig into S-corp elections, bookkeeping systems, and the book that finally made cash flow click for both of them. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Rashid is ready to take on international clients, but he keeps hesitating over how to protect himself if a contract dispute crosses borders. Preston and Austin argue that a contract isn't really about winning in court — it's about setting expectations before the work even begins. They walk through the deposit rules, red flags, and reference checks that keep freelancers from getting burned, whether their next client is down the street or halfway around the world. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Aisha wants to charge what she's worth, but like most beginner freelancers, she isn't sure where to start. Preston Lee and Austin Church tackle the age-old pricing question head-on, walking through the pitfalls of using your old salary as a benchmark and the trap of pricing based on what your freelance friends charge. They introduce two numbers every freelancer needs — a survival rate and a dream rate — and explain how packaging your work, not just your hourly rate, can be the difference between charging $1 or $3 for the same lettuce. It's a practical, no-fluff guide to setting prices that keep you in business and paid what you deserve. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices