I can’t believe what I walked into, but I’m even more shocked at what I walked out of.

According to the GPS, we were within a few hundred feet of our destination, but the bars on the blacked-out windows and the cracked glass obstructing old, faded signage told a different story. They definitely didn’t convey anything remotely customer-facing and welcoming (or even operational), but according to the GPS, this was the only vendor of its kind within a 60-mile radius, and we’d already come this far.

Stepping out of the car, I braced myself for what we’d encounter inside. Best-case scenario, the bars on the doors would be more than a cosmetic deterrent, and we’d find ourselves locked out, having to call off the mission altogether. Oh well. Worst-case scenario, we’d walk into a rodent-infested crime scene where we’d be taken hostage and instantly regret ever scoping out this business in the first place.

To my surprise, neither of those outcomes would be our reality; ours would be far stranger, and much less expected…

1. The perils of a generational business

Walking through the front door of this business was similar to the children’s experience of entering the hidden closet portal to Narnia. The transformation was stark, shocking, and impossible to reconcile without seeing it with your own eyes. Everything before this door — from the surrounding dilapidated structures, junk car lot, and rusted metal fences — was indicative of a dangerous, downtrodden, has-been establishment in deep decline. The interior — and the wizard behind the curtain — indicated just the opposite.

A cheerful man in a well-lit, expertly-maintained shop disarmed us with a charismatic smile that launched a surprising conversation. Within a few minutes, we’d struck common ground and quickly learned how he came to own and operate one of the only shops in his industry in this unusual location.

He hadn’t thrown a dart and chosen this business, nor was it the only one he owned. Instead, he was the third-generation heir to a much larger company that had pioneered this industry throughout our state. His siblings and extended family managed the other locations, but he’d been tasked with this strange expansion effort.

You see, his family had identified a gap in the market, and thus, using the same process they’d used to strike up successful shops in their other locales, he opted to repurpose that playbook here. The problem is that, while there may be a true gap in the market, filling it with the same playbook that worked in other markets isn’t necessarily a recipe for success, especially when you have to overcome the early-stage customer education hurdle.

In every other location where his family’s shops had thrived, those cities had been teeming with hundreds of thousands of members of the target market. In other words, each shop was a slam-dunk success, simply by existing in the places where hoards of customers were regularly seeking them out. Unfortunately, this kind of fast, smooth, or seemingly effortless success can promote unrealistic expectations around the required marketing, lead generation, and customer acquisition journeys when trying to replicate that success in a new geography.

Simply put, one of the gravest perils of a generational business is that it can lull an operator into keeping things status quo, yet assuming the same historical results will follow. Sometimes the greatest gift (being handed a plug-and-play business with resources and operations intact) can become the biggest entrepreneurial curse by failing to motivate the next-gen entrepreneur to change, improve, or evolve, thus pulling the trigger on an imminent decline they’ll never see coming because they didn’t think to look.

2. Some entrepreneurs actually don’t get this

One of the biggest shockers from this experience was just how oblivious some entrepreneurs can be to curb appeal and its impact on business. Walking into this shop felt like stepping through a portal — from an abandoned-looking exterior to an incredibly well-run operation. But here’s the catch: most customers wouldn’t make it inside to find out.

For this owner, the biggest competitive advantage — being the only vendor of his kind in a 60-mile radius — also created his biggest blind spot. He assumed that his monopoly insulated him from needing to attract customers. After all, if you’re the only option, they have no choice, right? Wrong.

A lack of competition breeds complacency. It creates a false sense of security — until a hungry, more strategic competitor sees the opportunity and moves in. This shop’s dismal exterior wouldn’t just fail to attract new customers; it could actually inspire an ambitious entrepreneur to take over the market by simply executing better.

The lesson? You’re never as untouchable as you think. You can’t assume that being the only option today means you’ll be the only option tomorrow. If your business looks like easy prey, sooner or later, someone hungrier and sharper will eat your lunch.

3. Inside-out businesses are the definition of slippage

In business, “slippage” refers to missed sales you never even had the chance to close. And that’s exactly what was happening here.

Customers are hardwired to judge a book by its cover, whether you like it or not. The contrast between the neglected exterior and the polished, inviting interior of this business was jaw-dropping. But guess what? Most potential customers would never know.

If a business looks unsafe, unclean, or just plain unprofessional, people don’t stop to investigate. They just drive right past it. In this case, a great customer experience was trapped behind an awful first impression.

The shocking part? The owner seemed totally unaware of this issue. He probably assumed that people in the know — his repeat customers, referrals, and loyal patrons — were enough to keep things running. But how many new customers never even stepped inside because they couldn’t get past the curb appeal disaster outside?

A business can’t grow to its maximum potential on word-of-mouth alone. If your physical presence actively repels first-time customers, you’re leaking sales. And even if you run an exceptional business, it won’t matter if customers never get through the front door.

4. The waiting game is a risky one

One of the most alarming things about this business owner’s approach? He was waiting.

His entire strategy was built on the hope that his location would eventually become more populated with his target market. In other words, he was betting on future foot traffic to fix his customer acquisition problem.

This is not a strategy — it’s a gamble.

The internet, competition, and shifting consumer behavior have made “just wait for people to find us” a dangerous mindset. Passive business owners assume that:

• Customers will eventually discover them
• The market will grow around them
• Being the only option is enough to stay in business

But hope is not a business model. What happens if a competitor moves in before the market grows? What if demand never materializes at the scale he expects?

The biggest red flag? He was doing nothing to accelerate his own success. No aggressive marketing. No strategic partnerships. No digital lead generation. He was simply sitting back and waiting, assuming success would come to him.

If you’re passively waiting for the market to come to you, you’re not building a business — you’re placing a bet you can’t afford to lose.

5. Nothing is better than something bad

There’s an old saying: “No presence is better than a bad presence.” And this business was the perfect example.

In today’s world, a strong digital presence can outperform a terrible physical one. If customers show up to a sketchy, run-down storefront, it’s actively harming the brand. At that point, it would be better to have no physical presence at all.