Homeless Entrepreneurs

Ken West
3 min readDec 2, 2019

A better way to solve the homeless problem

The Boston Common… It was raining. I cursed when I discovered that the entrance to the underground garage was locked. I turned, ready to run over to the main entrance about three-hundred yards away.

All of a sudden the locked door swung open and a voice said, “Good evening sir.” A homeless woman who had taken up her post inside the locked glass door, held it open for me.

I hesitated for a moment — then entered. I thanked her and hurried down to my car. The garage has four pedestrian entrances. Three of them are locked after 6 p.m., forcing patrons to use the main entrance. But I was one of the lucky ones this cold, rainy evening.

For about a year my “doorman” was always on duty after 6 o’clock. Her simple act of opening the locked door and greeting me was a useful service for which I sometimes gave her a dollar or pocket change.

Six months after her tenure as unofficial doorman and greeter, she expanded her business. During the early afternoon hours she worked outside on an adjacent park bench, offering quick “portraits” and drawings to wandering tourists. She had bought some inexpensive sketchbooks and colored pencils for this new venture.

I never found out where she slept at night. Garage security guards would send her away after eleven o’clock. This quiet, resourceful woman is one of thousands of homeless people who would never think of shaking an empty cup in your face.

They know that offering value, not pleas for pity, is the right way to go. They are homeless entrepreneurs.

What distinguishes these individuals from beggars, hustlers, and con-artists is their honest attempt to offer uncoerced goods and services to make money. In other words, they’re business people. They find a need and fill it. They may be temporarily homeless, but they’re not down and out.

Homeless entrepreneurs come in every size and shape. Some are street musicians, leaflet distributors, newspaper sellers, door openers, and jack-of-all-trades. Others do whatever odd jobs they can find. What they lack in capital, they make up with ingenuity and spunk. They are proud of their ability to survive.

And like us, they come face to face with the bad fruits of big government.

For instance, some try their hand at shining shoes, only to be told by the police that they need a license, vendor’s permit, and sales tax log to do so. Even when trying to find a cheap room, they discover that paternalistic and “progressive” government has shut down the tenement houses which once served the needs of the poor.

Those of us who get exasperated by constant pleas from beggars, should demonstrate our value system by rewarding homeless entrepreneurs instead. They do not resort to pity or threats; they offer their best efforts. They understand the crucial difference between taking money and making money.

With few exceptions, homeless entrepreneurs have been ignored by the media. Instead, we are offered distorted caricatures of the homeless. This does a disservice to them and to us.

Rather than wasting millions of dollars on handouts, we should be teaching the homeless how to make money. Some of the instructors could come from the ranks of our present homeless entrepreneurs.

They could even help teach graduate students on the critical need of focusing on the customer and delivering value.

As I approach a city convenience store to buy a magazine, a tall homeless man snaps to attention, opens the door with a flourish, and greets me as if I’m a big-shot. He doesn’t ask for money. As I leave he wishes me a good evening.

There is no intimidation — only a man providing a service usually reserved for hotel guests and the rich. Next time I resolve to put him on the payroll.

Ken West is the author of Achieve Your Purpose! (Formerly titled, Get What You Want; both editions are on Amazon.).