The Second Website Problem: Why DIY Sites Eventually Need Experts with Kelsey Gilbert-Kreiling
Many business owners build their first website themselves. However, there often comes a point when a website stops being a simple online presence and starts becoming a critical business tool. In this episode of the Rebellious Times Podcast, I sat down with Kelsey Gilbert-Kreiling, Founder and CEO of Week of the Website, to discuss Squarespace website design, agency innovation, AI, entrepreneurship, and the challenges of balancing business growth with family life.
From Fashion Design to Agency Founder
Kelsey’s journey began far away from digital marketing. Originally studying fashion design, she discovered a passion for the intersection of creativity and technology. After working with hospitality brands in Chicago, she found herself building websites and helping businesses establish their online presence. Eventually, that work evolved into launching her own agency.
How Week of the Website Was Born
Most agencies build websites over several months. Kelsey took a different approach. Inspired by conversations with the Squarespace team, she developed a process that allows clients to complete an entire website project in a focused one-week sprint. As a result, clients avoid lengthy delays while receiving a website built around strategy rather than endless revisions.
Why DIY Websites Eventually Reach a Limit
Although website builders have made it easier than ever to launch a site, Kelsey believes the real value comes from the process behind the website. A DIY site may look good. However, a strategic website functions as a business tool that aligns stakeholders, communicates value, and supports growth. Therefore, her team focuses as much on discovery and consultation as they do on design.
Why Squarespace Remains the Platform of Choice
Week of the Website specializes in Squarespace website design because of its balance between usability and flexibility. Furthermore, Kelsey appreciates that clients can manage and update their own sites without relying on developers for every small change. For service businesses, hospitality brands, and event-driven organizations, that simplicity can be a major advantage.
Using AI to Remove Friction
Rather than replacing people, Kelsey views AI as a way to remove administrative bottlenecks. Her team uses tools such as Claude to streamline onboarding, improve communication, and eliminate repetitive tasks. Consequently, designers and strategists can spend more time focusing on the work that clients truly value.
Chapters
00:00 Introduction to Kelsey Gilbert-Kreiling
02:53 The Journey to Agency Founder
05:56 The Birth of Week of the Website
08:48 The Evolution of Website Design Process
11:50 Navigating DIY Websites vs. Professional Help
15:03 Choosing Squarespace: A Strategic Decision
17:45 Leveraging AI in Agency Operations
21:00 Launching Eventually Ticketing
24:00 Balancing Family Life and Entrepreneurship
Building a Business Around Family
One of the most inspiring parts of our conversation centered on family and entrepreneurship. While on maternity leave with her second child, Kelsey developed the concept for Eventually Ticketing, a new event ticketing platform built for Squarespace users. Her story is a reminder that entrepreneurship does not always require choosing between family and ambition. Sometimes the best ideas emerge when the two intersect.
Kelsey Links:
weekofthewebsite.com
LinkedIn
Podcast: Play in new window | Download
