Entrepreneurial Lessons from the Street

When I’m asked about my first job, I usually reply with the story of beginning my career in advertising as a copywriter at a prestigious Madison Avenue advertising agency. But my first REAL encounter with the world of work was as an entrepreneur. I was a “human jukebox” on the street of Manhattan every summer during college starting at age 16.

I stood in a refrigerator box I’d decorated — usually on the corner of 5th Avenue and 53rd Street. When a passerby put a quarter in the slot, I popped out of shutter windows and played the song of their choice on my sopranino recorder. This little stunt got me in the papers and on TV a few times (see photo), a spot in the Lincoln Center Festival of Street Performers, and made me a couple of thousand dollars a summer, mostly in quarters.

I invented this gig because I needed a summer job. I was too young to waitress anywhere that served alcohol, and I couldn’t type very well. But honestly, I didn’t want a summer job like anyone else’s…I wanted one where I could use my talents, and get paid for it. Now, 30 years and a whole corporate career later, that’s still my goal.

But today, thinking back to those hot days on the NYC pavement, there were things I learned on the street that it would be good to remember in my current entrepreneurial life. You might want to keep in mind too. Here are the top ones:

1. Not everyone will love you. Deal with it.

Most of the people who saw me laughed or smiled, and some stopped to watch me for a while. But every day, there was usually at least one senselessly hostile passerby who would yell out something like, “Why don’t you go get a real job?!”  This would wound me terribly, and usually the incident would be what I remembered most from the day, no matter how many other people had enjoyed my act. I knew even at the time this did not make any sense. It still doesn’t. And it still hurts when someone criticizes me, even if I know it’s more about them than me.  But instead of trying to talk myself out of these stings, I just figure it’s the cost of being in business for myself.

2. One person’s quarter is another person’s hundred-dollar bill.

Sometimes, one or another harried-looking businessmen in wingtip shoes and an expensive suit would stop and watch me for a while. Later when I investigated my “haul”, I would often find a hundred-dollar bill among the quarters. I didn’t do anything differently when one of these guys was there. But the value of a few minutes of humor and playfulness was worth that much to them at that moment in their lives. The value of what you do as an entrepreneur can go up — in my case as much as 4000% — depending on who needs what you’ve got, and how much it’s worth to them.  If I’d been smarter back then, I’d have set up my box on Wall Street.

3. Go where the business is.

I started off doing the act inside Central Park, since that was where I grew up seeing street performers. I soon discovered that the park was pretty quiet most weekdays, and on weekend was full of families who would watch for long periods of time and not pay me very much. I moved my base of operations to 5th Avenue and saw my income skyrocket. There was a steady flow of new faces, and I didn’t have to work so hard to get people to stop. The social proof of a few people always watching made it easier for others to join in.

4. Plan your time off for the off times.

As entrepreneurs we often work 7 days a week, and it’s not healthy. In my Human Jukebox days, I was on my feet in the heat for hours at a time, and I knew a day off a week at least was a necessity. The trick was decide when to take it. I noticed that even at my prime spot on 5th Avenue, Mondays were usually a bad day. People were grumpy, hurried and not in the mood to stop for a smile.  I decided instead of beating a dead horse to take Mondays as my day off. This was especially welcome since I would sometimes work in Central Park on Sundays — a long, grueling but satisfying day since I entertained a lot of children. Today, I still love taking time off when other people are working — one of the joys of working for yourself. And I still take Mondays for myself, usually to do visioning and planning for the week, preferably poolside.

5. Know what you are REALLY selling, and keep improving.

My first year as the Human Jukebox, I just played songs. I realized that people were not really buying a song, but the surprise of seeing a person pop out of the box and play. So I decided to add a visual element — a different “costume” (usually homemade headgear) to accompany each song. This had the effect of keeping the act fresh, and often led to  more sales from the same person as they wanted to see what I would wear to play a Bach Brandenburg Concerto (see photo again!) as opposed to the theme from the musical “Annie!” (a showercap covered in cotton balls spray-painted orange). Bottom line — I added more value, so I made more money.

What’s the craziest job you ever had, and what did you learn from it? Share your thoughts in the comments below!

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