In this episode, I talk with Jack Redley about what he learned from making 100+ episodes of Webflail. We get into why he decided to stop the podcast, what freelancing really looks like after the hype, and how his thinking around niching, pricing, and clients has changed over time.
We also talk about trying to build a studio, why that path didn’t stick for him, and how community and side projects have shaped his work. Along the way, Jack shares recurring themes he kept hearing from Webflowers, his take on where Webflow is heading, and why doing the work matters more than talking about it.
Check out Jack
Timestamps
- 00:00 teaser
- 00:18 End of Webflail?
- 06:46 The Love-Hate Relationship with Freelancing
- 10:59 Finding Your Own Thing in Web Design
- 12:53 Niching
- 15:47 The Importance of Experimentation
- 21:30 Chasing Money
- 26:00 The Balance of Project Scope and Payment
- 34:49 Understanding Day Rates vs. Hourly Rates
- 37:05 Setting Boundaries with Clients
- 40:16 Saying No to Old Clients
- 42:55 The Importance of Communication
- 47:32 Talking About the Price
- 51:31 Key Themes from Webflail Interviews
- 58:57 On Doing Weird Sites and Videos About Those
- 01:02:54 Should Web Designers Have a Style?
- 01:06:00 The Evolution of Webflow
- 01:12:59 Navigating Changes in the Webflow Ecosystem
- 01:15:17 Meetups & Events
- 01:21:43 Lessons from Building a Studio
- 01:29:08 Reflections and Gratitude
- 01:31:30 Weird Finnish Thing
