Hard Lessons from Our Two Epic Marketing Failures

What happens when everything is perfect—except the product? Twice in our history at The Artesian Network, we found out the hard way.

Failure #1: When the Product Isn’t What It Seems

Several years ago, we were retained to revamp the messaging, positioning, and demand generation strategy for a five-year-old cyber-security-related company. Backed by over $130 million in funding from top-tier VCs, the company had only 12 customers—but with that level of investment, we assumed the fundamentals were solid. Sales just needed a tune-up.

Within two quarters, the data told a different story. Our campaigns were hitting the right buyers. Engagement was high. Qualified leads poured in. But deals stalled. Proof of Concepts (PoCs) didn’t convert. The sales pipeline became a graveyard.

We stepped outside our formal scope and dug deeper. What we found was alarming: – Of the company’s 12 customers, only two ever installed and used the product. – One didn’t even renew after the initial contract. – Worse, nearly all of these customers were tied to personal relationships with the CEO or investors—not arms-length, market-driven sales.

The core product had a critical flaw: it depended on a notoriously unstable third-party software component that required constant maintenance and specialized expertise. Most companies didn’t have the resources—or patience—to deal with it.

Despite presenting our findings, we faced heavy pushback. The CEO insisted the market was the problem, not the product. We resigned. Within a year, the company was sold off in an asset fire sale.

Lesson #1: Never Assume Product-Market Fit Has Been Validated—Even by Top VCs.

The startup world often points to the high-profile case of Elizabeth Holmes and Theranos, but there are countless smaller-scale versions of this story across Silicon Valley. Big funding doesn’t guarantee a product works—or that the market even wants it.

Failure #2: The AI Gold Rush That Had No Gold

Our second painful lesson came at the height of the early AI boom. We were introduced to a promising AI software startup by a well-known investor we had worked with many times. The assignment was clear: Build the brand, launch demand generation, and drive $3 million in ARR in year one.

We executed flawlessly—branding, messaging, sales and marketing tech stacks, content strategy. Then we hit a wall.

– No customers could be found for interviews. – The CEO provided “translated” customer quotes and refused to let us speak directly with any users. – With three weeks before the planned launch, we demanded hands-on time with the product.

The result? It didn’t work. None of the promised features functioned as advertised. It was a brilliant idea, but nothing more than a prototype wrapped in a sales pitch.

We raised our concerns directly with the CEO and were dismissed. We exercised our right of termination, contacted the introducing VC as a professional courtesy, and walked away. The company limped along for six more months before being quietly sold for parts. To top it off, we had to fight for nine months in arbitration just to recover unpaid invoices.

Lesson #2: If You’re Marketing a Product, Use It Yourself. And Speak Directly to Real Customers.

Everything begins and ends with the product. No marketing brilliance, demand generation strategy, or sales excellence can make up for a product that doesn’t deliver real value.

Final Thought:

Before you set out to “fix” sales and marketing, run due diligence on the product itself. Validate that the early customer base is real and that buyers aren’t simply friends of the CEO or investors doing favors.

In our Build, Test, Prove methodology, we emphasize this critical truth: “Great marketing accelerates momentum. It cannot create it where it doesn’t exist.” Read more about the Build, Test, Prove framework here: https://www.linkedin.com/pulse/build-test-prove-jonathan-w-buckley-3onqe/

In early-stage technology companies, the hardest lesson is also the simplest: There’s no substitute for a product that works.

#startups #marketing #productmanagement #cmo #growth