Some client relationships start with red flags so bright you’d think they were impossible to miss. And yet—when you’re young, hungry, and genuinely excited about what you do—it’s easy to mistake chaos for ambition.
Twenty years ago, Chris Simental, Co-Founder of Ripe Media & Tech Strategist, was introduced to a client through a mutual acquaintance. The pitch sounded exciting on paper: build a dynamic ecommerce platform that would serve as a cultural hub for visual art, fashion, music, and film. A one-stop digital destination for creatives. The kind of project that makes a portfolio sing.
What they didn’t know yet was that the vision far outpaced the client’s understanding of what building that vision actually required.
The client—a family of four—came in with enormous expectations and very little grasp of how the digital world worked. From the very first meeting, the demands were overwhelming, and not always rooted in reality. One request stood out above the rest: they wanted their audience to be able to sell art without needing a computer or a camera. No digital footprint. No uploads. No friction.
It was a creative brief that defied the basic logic of ecommerce. How do you sell something that doesn’t exist online? Chris and his team did what good builders do—they pushed forward, tried to bridge the gap between expectation and execution, and delivered an initial website they were ready to stand behind.
Then came the soft launch.
In the world of web development, a soft launch is standard practice. You release, you gather real user data, bugs surface, you fix them. It’s not a failure—it’s the process. Chris knew this. His team knew this. What he didn’t anticipate was that the client did not.
Days after the launch, an angry email landed in their inbox. The client was furious. Momentum had been lost, they claimed. Users were disappointed. The bugs—normal, expected, fixable bugs—had apparently derailed everything. The tone was accusatory, the frustration outsized, and the response completely disproportionate to where they actually were in the development cycle.
It felt personal in a way that didn’t quite add up.
And then, eventually, it all made sense.
As the relationship unraveled, a startling detail emerged: the business wasn’t really about art, fashion, music, or film at all. The entire venture had been constructed as a vehicle—a means for the client to transfer business ownership to his son and secure a US citizenship in the process. The cultural platform was never the point. Chris and his team had spent months pouring their expertise into a project whose real purpose had never been disclosed to them.
In today’s episode, Chris Simental breaks down exactly what went wrong, what he wished he’d caught earlier, and what every creative professional needs to know about vetting clients before the contract is signed.
Because sometimes the nightmare isn’t in the code. It’s in the fine print nobody showed you.
Morgan Friedman
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