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Episode 164

Press One for Frustration: The Decline of Customer Service

August 11, 2026 · 31 min

Delroy gets personal about a frustration he knows plenty of listeners share: trying to get basic — or even complex — customer service, and finding actual human connection nearly impossible now that AI seems to be the default. Whatever happened to a real person helping you sort out a problem with an order, a refund, or anything else that needs an actual answer?

He’s hung up the phone more times than he can count out of sheer frustration, because — as he puts it — we shouldn’t be holding conversations with machines. It’s gotten to the point where he’s stopped payments on several accounts entirely, simply because he couldn’t get through to a real human being to resolve his issue.

Shopify gets called out by name as a prime example: instead of a straightforward answer, you’re stuck digging through what feels like an entire encyclopedia of self-help articles — and even then, the “answer” often isn’t really an answer at all. Delroy’s take: these systems don’t feel like they’re designed to help customers. They feel designed to frustrate them.

His advice to anyone dealing with the same thing: if it’s not a matter of life or death, cancel those accounts and stop putting yourself through the frustration. These companies clearly don’t value your business — so keep your money in your wallet.

“We should not be holding conversations with machines. I think these systems were designed to frustrate customers instead of helping us.”
Key Takeaways
  • Real human help is disappearing behind AI and automated systems, even for basic issues.
  • Frustration with automated support has real consequences — including customers walking away from accounts entirely.
  • Companies like Shopify often bury answers in self-service articles instead of offering direct help.
  • An “answer” that doesn’t actually solve your problem isn’t an answer.
  • If it’s not life or death, don’t keep putting yourself through it — cancel and take your money elsewhere.
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