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Client Horror Stories

That time your client-win-of-the-year sues you for most of the contract’s value (with Jason Pittock)

In our fourth episode of Client Horror Stories, we have Jason Pittock, CMO of ClickGuard, telling Our Beloved Host, Morgan Friedman, and us a passionate and gripping story about making huge deals with big fishes while you are still a reckless (and naive) 21-year-old.

Filled up both with a British accent and Argentinian slang, this story takes us to 6 years ago in the streets of Palermo, Buenos Aires. Back then, Jason, who was a very ambitious and smart young man, happened to land this millionaire deal for the company that he was working for and didn’t hesitate for a second before he agreed.

From the beginning, we have a feeling that bad luck was chasing him down: A surprisingly pregnant project manager, broken elevators on delivery day, and a fully flooded storage basement were only the first signs the universe sent Jason to tell him to back off. However, being a persevering and responsible person, Jason continued to do everything he could to accomplish this deal until the very end, when a lawsuit for 50% of the job value arrived.

This story includes everything from lawyers with food stains in their shirts, clients stalking you at the beach, and even calling your dad for some advice. Reaching the end, Jason leaves us with some very valuable lessons on boundaries, mental health, and the importance of telling someone to back off when needed.


Jason Pittock


Morgan Friedman