One of the aspects that I love most about what I do is getting to meet a diverse group of entrepreneurs and leaders of small to medium-sized businesses (SMBs) on a regular basis. Many of them are based near where I live and have that unique New York City mix of earthiness, wiliness, and sophistication. While there are a lot of stubborn and frustrating—and a few truly crazy—people in this city, there are also many born storytellers eagerly waiting for an audience like me.

In early 2016, I met the owners of two prominent companies in New York City’s taxi and limousine industry who fit that description to a tee. One was a woman who owns and runs one of the city’s premier limousine services which is based in south Brooklyn. The other is one of New York City’s largest taxi medallion holders and brokers.

They had no trouble telling me how Uber, Lyft, and other disruptive companies—seemingly without so much as a shrug from NYC regulators—were devastating their businesses. And yet, for all their accomplishments and business savvy, I was surprised that both these entrepreneurs had allowed themselves to be stopped dead in their tracks. Revenues had plunged and formerly healthy margins had all but disappeared, threatening everything they had worked hard to build over their entire adult lives.

It was also clear to me very early in our conversations that they weren’t about to take advice from someone outside their industry, preferring instead to stick to what they knew. They are interesting examples of what can happen when perilous and unproductive mindsets like the few listed below take over.

I’m Always the Smartest in the Room

The Brooklyn-based businesswoman explained to me how she had always been at the top of her class in school and college. Like a modern-day Cassandra, she was constantly warning her colleagues and competitors about the dangers of Uber and Lyft with little effect. “I knew what was happening, but it was like talking to a brick wall,” she said.

But instead of taking the opportunity to make changes to her business, she had done nothing beyond forecasting death, doom and destruction. Six years later, she was in danger of literally driving both herself and her company over the cliff.

Although not quite as prescient as our Cassandra of the taxi and limousine industry, the gentleman who owns the largest taxi medallion brokerage in New York City is in fact originally from Greece. He had started his professional life in the city twenty-five years earlier as a taxi driver before he started building his business. He is charismatic and can talk a very good game; he also spent a lot of time telling me how smart he was.

But the kicker came when he said he was making $78 million in revenue annually but had racked up $100 million in debt buying and selling the medallions taxi drivers need to own and drive New York City taxis. In the previous five years, the value of these medallions had dropped to about one-fifth of the price they had commanded in the years before Uber, Lyft, and others entered the scene.

He had also taken no preemptive action to rethink his business model and allowed the situation to go on endlessly, thinking at some point he would be able to fix the problem—until it was too late.

He then explained with a flourish that he was working with Goldman Sachs—the smartest of the smartest—to solve the problem by restructuring his company.

These two business owners might have been smarter than me, but at least I had a business that was thriving and growing.

I’ll Wait until the Storm Blows over

Owners of businesses subject to back-and-forth swings in politics and regulations find it hard to commit to significant change when they can’t figure out what’s brewing in the halls of power. They often make do with a wait-and-see strategy. While this can sometimes be a reasonable and productive choice, it also can be simply an excuse for inaction.

Both entrepreneurs above were part of various organizations tied to the NYC Taxi and Limousine Commission and were involved in efforts to convince regulators to make decisions that would help them. They hesitated to make too many drastic changes to their businesses, such as investing in mobile technology with similar functionality to that of Uber or hedging their exposure using more sophisticated financial instruments. They just hoped things would go back to the way they used to be once the regulators woke up and righted their wrongs.
Unfortunately, that never happened.

I’m Just Too Nice

After an hour of frustrating conversation, the owner of the limousine service in South Brooklyn walked over to a cat sunning itself in the window of her office. She petted it, looked through a hole that had once been the window that allowed her to watch the garage where her people worked, and wistfully said: “You know, I’m just too nice.” This, after she had yelled at her people to shut up so she and I could hear each other talk. Maybe she was too nice. The situation clearly was so bad for her that she was losing sight in one eye, had been in the hospital for several ailments, and was struggling with a son who was addicted to drugs.

Perhaps if she hadn’t been “so nice,” she might’ve been able to enjoy her life more than she was.

I’ve worked through many other unproductive mindsets and behaviors with my clients, The most common are I’m just an imposter and everybody knows it, I’m not worthy and one of the hardest to identify and resolve: The Magpie Syndrome. This is a vicious cycle of always running after the next shiny object, Falling prey to this frame of mind often ends up in unhappiness in your personal life and failure or bankruptcy for your business.

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