Trapped

Trapped

Author: Millo August 14, 2025 Duration: 48:14
On today’s show: do you ever feel trapped by the decisions you make in your business? Our guest Morgan loves to write. But, early on, she took on quite a few social media clients. Then, those clients referred more clients. And suddenly, most of her client work is focused on social media marketing — not writing. So what do you do when your former choices have boxed you into a future you don’t necessarily want? It’s all on today’s episode of Freelance to Founder. Here we go… This episode was originally aired on December 14, 2023. PS: Get featured in an upcoming Q&A! Just visit ⁠http://freelancetofounder.com/ask⁠ and submit a question.  Support our Sponsors Our generous sponsors make this show 100% free to you. Support them at the link below. ⁠https://freelancetofounder.com/sponsors⁠ Get your own on-air coaching call We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, ⁠click here⁠. Leave us a review on Apple Podcasts: If you enjoy the show, can you do us a favor and leave us an honest rating and review on Apple Podcasts? We'll love you forever. ⁠Click here to leave a review⁠. More Recommended Listening: This show is a part of the Podglomerate, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the ⁠website⁠ and sign up for our newsletter. We suggest you also try other Podglomerate shows about entrepreneurship, business, and creativity, such as ⁠Rocketship.fm⁠ and ⁠Creative Elements⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

There’s a common gap between working for yourself and truly building something that lasts, and Freelance to Founder lives in that space. This isn’t just theory; it’s a daily conversation for freelancers who are tired of the unpredictable income and ready to create a real business. Host Preston Lee draws from his own journey from freelancer to someone who has built and sold companies, and he brings that grounded perspective to every episode. Nearly every weekday, Preston is joined by other founders and entrepreneurs who’ve navigated the same path, breaking down the practical steps you can take to scale your solo operation. The call-in format means you’re hearing real questions from people in the trenches, facing the same client issues, pricing dilemmas, and growth plateaus you might be. Listening to this podcast feels like having a direct line to a supportive and experienced mastermind group, one that focuses on actionable strategies over vague inspiration. It’s for the designer, writer, developer, or consultant who’s ready to move beyond the feast-or-famine cycle and lay the foundation for something more substantial and sustainable. The discussions are candid, the advice is tested, and the goal is always clear: helping you transition from a solo practitioner to the founder of a thriving business.
Author: Language: English Episodes: 100

Freelance to Founder
Podcast Episodes
Who's Actually the Client Here? [not-audio_url] [/not-audio_url]

Duration: 11:45
Sarah delivered exactly what her client asked for—until the spouse entered the chat. Now the feedback is contradictory, the timeline is slipping, and the relationship feels like it's unraveling. This episode breaks down…
Is Your Proposal Tool Actually Costing You Clients? [not-audio_url] [/not-audio_url]

Duration: 15:56
Clay is buried in proposals and contracts—jumping between tools, second-guessing every software decision, and wondering why nothing ever feels quite right. Preston and Clay pull back the curtain on the client management…
The Invoice You're Too Scared to Send [not-audio_url] [/not-audio_url]

Duration: 14:27
Laura completed the work, sent the proposal, and then froze. The invoice is sitting there — unsent — because she's convinced this is the moment she loses a client she can't afford to lose. Clay and Preston dig into the f…
Pay Gap: Freelancers vs. Agencies [not-audio_url] [/not-audio_url]

Duration: 24:04
Amy Bridges posed a simple question in the Milo Mastermind community and it sparked a conversation Preston and Clay couldn’t let go: does presenting yourself as a freelancer or as an agency actually make a difference in…
Letting Go of Source Files = Good Idea? [not-audio_url] [/not-audio_url]

Duration: 14:40
Kevin did a brand redesign for an old colleague two years ago — got paid, and moved on. Now the client's new marketing manager is asking for the original InDesign source files to update the brand guidelines internally. K…
Love Your Craft, but Tired of Business? [not-audio_url] [/not-audio_url]

Duration: 14:27
Rachel Stone King still loves design and branding—but the business side of freelancing has started to feel like a weight she can't shake. The thought of networking, hunting for clients, and staying motivated has left her…
The Power of Saying "No" To Crazy Clients [not-audio_url] [/not-audio_url]

Duration: 20:10
Kirstie runs a design business and a client emails her at 5:22 p.m. on a Friday needing an ad designed that same night. Sound familiar? Preston and Clay break down the real question behind rush fees—not just what to char…
Don't Charge by Hour or Project. Do this... [not-audio_url] [/not-audio_url]

Duration: 17:04
Lanya has a freelance project in front of her, she’s estimated the hours, and her client is open to either hourly or project-based pricing—so now what? Preston and Clay make the case that the real question isn’t hourly v…
Remove Pain from Recurring Revenue [not-audio_url] [/not-audio_url]

Duration: 22:09
Erica is a web and graphic designer who invested in a coaching program built to turn designers into full-service marketers—complete with monthly retainers, ad campaigns, and recurring revenue. The strategy looked great o…
The Best Marketing Tactic to Get New Clients [not-audio_url] [/not-audio_url]

Duration: 22:03
Matt runs Barrow Studio, a brand identity and strategy agency in Bristol, UK—and he's drowning in advice. Every newsletter, YouTube channel, and podcast promises a different "marketing golden ticket": build an email list…