November 30


The Perils of Relying on AI: A Cautionary Tale

This guy’s gonna RUIN his business with AI…

Let me explain what happened and what you can do to avoid it.

I really enjoy meeting new folks, getting to know their business’ better, and leveraging my 17 years in FinPub to add value, often with a mere “thank you” as payback.

This ‘give more, expect less’ mindset has brought me loads of opportunities and great friendships through the years- but I digress.

In my LinkedIn travels, I stumbled upon a recently launched site (backed by some serious players).

Their products, although intriguing, lacked robust marketing. The two Canadian founders, while young, were gaining attention.

So I did my thing and connected!

Initially, we engaged in social media chat—always a bit unpredictable. Conversations start and pause, distractions abound, but getting on a call required a more organized approach.

Enter the email conversation, where things took a peculiar turn.

Upon receiving the first response to my ‘thanks for continuing the convo here’ email, I noticed something odd—his replies resembled ChatGPT-generated responses.

Curious, I asked a friend to run his messages through an AI filter…

**This should have been a warning sign.**

Although not entirely unheard of, considering busy schedules and the occasional reliance on AI, I pressed on to coordinate a call.

Spoiler Alert: The call did not go well.

It became apparent instantly that this ‘co-founder’ was inexperienced. Approaching the situation with caution, my intention was to learn and offer insights, not to criticize.

Unfortunately, he struggled to answer fundamental questions about product sales and conversions—critical knowledge for someone in charge of marketing. Despite his company’s investment in ads, he had zero answers to basic queries, raising concerns.

After posing another straightforward question, he abruptly hung up, offering no explanation—behaving much like a nervous kid evading a conversation with a friendly inquiry.

This situation is disconcerting on multiple levels.

First, it reflects poorly on the company to have a marketing lead exhibit such ineptitude.

Second, it’s evident that this young entrepreneur is in over his head and genuinely needs assistance. However, the help he requires doesn’t come from AI.

I don’t know how his business will unfold, but I hope good people come around these young guys and get them on track. After all, there’s only so much VC money can do when one of the owners relies on AI for general communication and then crumbles to pieces during a real world conversation.

Be careful with HOW you’re using AI as it can add a TON of value…or ruin it.

And if you’re using it for communications…


P.S. I won’t pretend to be an AI expert (unlike most of LinkedIn nowadays lol)…however I do know how to use it to make my life and marketing tasks MUCH easier. So lean on the tool and use it as a tool.


AI, Founder Advice, Marketing Warning

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