Ep 118 – Jamie Brindle – From Freelancer to Entrelancer: Building a Business That Scales

Featuring: Jamie Brindle

In episode 118, I’m joined by Jamie Brindle—a freelancer, strategist, and creator who’s built a half-million-strong audience around helping creative solopreneurs build sustainable, scalable freelance businesses. In this conversation, Jamie breaks down what it means to be an “Entrelancer”—a hybrid of entrepreneur and freelancer—and why the traditional view of freelancing is overdue for a reboot.

We talk about why having an audience builds instant trust, how freelancers can evolve into business owners without employees, and the myths around websites and portfolios that keep too many creatives stuck in planning mode instead of taking action. Jamie also shares a powerful framework for moving strangers into long-term client relationships—and why every freelancer should be thinking like a strategist, not just a task-taker.

Whether you’re freelancing, running an agency, or somewhere in between, this one’s packed with fresh thinking.

Key Bytes

• Jamie shares the origin of the term “Entrelancer”—and how it reflects a more modern, business-minded freelancer. • He explains how their TikTok content (originally not for clients) unexpectedly opened doors to Fortune 100 opportunities. • We dig into the importance of digital products, productized services, and building systems to support time freedom. • Jamie outlines the four stages of the customer journey: Stranger → Lead → Client → Client for Life. • He gives a masterclass in how to manufacture delight, over-deliver, and secure repeat work. • We challenge the sacred cows of freelancer websites and portfolios—and why Jamie believes they’re massive time-wasters. • Sales anxiety? Jamie offers a grounded, simple mindset shift that removes pressure and focuses on being helpful. • He explains how positioning yourself as a solution—not a task-taker—is the unlock to charging more and building authority.

Chapters

00:00 Welcome and Intro to Jamie Brindle 01:00 The accidental power of TikTok and building trust 04:30 Redefining success as a freelancer 07:00 “Entrelancer” vs. freelancer: What’s the difference? 11:40 Scaling without employees: Productized and digital offers 13:00 Pivoting from video work to social media consulting 15:25 Lessons from shifting services and getting back in the field 19:30 Jamie’s four stages of the customer journey 24:00 Reframing sales: It’s just solving a problem 28:00 Positioning yourself as a strategic partner 34:00 Why portfolios and websites are the biggest time wasters 37:00 Final thoughts and closing

Jamie Brindle is a freelancer who gives advice to over half a million other creatives on social media about building a scalable and sustainable freelance business.

Contact Jamie on their website or @thejamiebrindle on all socials.