We hear a lot about wins in business, but failures are usually where the real lessons come from. To dig into that, I asked business leaders a simple question: What is something you tried for your business that completely failed?
Here’s what they shared and the key takeaways.
1. Building Without Customer Input Backfires
“I had… wasted months of my life constructing what I thought our customers needed… fewer than ten percent of users even once clicked on it… no success ever taught me so much as that silence.” – David Batchelor, Founder / President, DialMyCalls
One of the most common mistakes is assuming you know what customers want without actually asking them.
David Batchelor shared that he spent months building a feature based entirely on assumptions. There was no feedback loop, no testing, and just a belief that it would work. When it launched, adoption was almost nonexistent.
The lesson here is straightforward: skipping customer input is expensive. A few early conversations could have completely changed the outcome. Now, he focuses on validating ideas before investing time into building them.
2. Features Don’t Sell, Stories Do
“My open rate was great, but my clicks were next to nothing… I spent so much time perfecting my descriptions… rather than trying to create a ‘story’ about the experience.” – Silvia Lupone, Owner, Stingray Villa
It’s easy to assume that more detail equals better marketing, but that’s not always true.
Silvia Lupone ran an email campaign that looked promising at first glance. People opened it—but they didn’t take the next step. No clicks, no inquiries, no results.
The issue was the focus. The message highlighted features instead of creating an emotional connection. After shifting toward storytelling and real guest experiences, her campaigns started to perform much better.
3. Missed Calls Mean Missed Revenue
“The majority of people who went to voicemail either didn’t leave a message… and just went to the next business… we began to treat missed calls like revenue, not nuisance.” – Dennis Holmes, CEO, Answer Our Phone
Sometimes the biggest losses come from things that seem small in the moment.
Dennis Holmes explained that his team relied heavily on voicemail to handle overflow calls. The assumption was that people would leave a message or wait for a callback—but most didn’t.
Once they realized how much business they were losing, they made changes like improving live coverage, fixing call routing, and making sure urgent calls were handled faster.
That shift in mindset turned a passive system into a more proactive one.
Final Thoughts
The biggest takeaway is that failure often comes from small oversights of assuming instead of asking, describing instead of connecting, or underestimating everyday gaps. The fixes aren’t complicated, but they do require paying attention. Talking to customers, understanding behavior, and making small adjustments can prevent bigger problems down the line.
In most cases, the lesson isn’t just that something failed, it’s why it failed!