What Entrepreneurs Can Learn From A Homeless Man

Last week we had a cold and rainy day here in Chicago.

I was downtown on Madison Street waiting for the #20 bus when a homeless man walked up to me and asked for a dollar.

Now, I have this belief that regardless of circumstance, people shouldn't be robbed of general decency from fellow humans, so I typically always will listen and provide a response when people ask me for money. Depending on my day, how I feel, if I have actual cash on hand, and most importantly if I feel they make a compelling argument, I make my decision.

So, more or less, I listened to his pitch. It went like this:

Guy: "Excuse me sir, I'm so sorry to bother, can I ask you something?"

Me: "Sure."

Guy: "I'm homeless, and I wasn't anticipating it raining today so my plan was to walk to ____ (I forget now where he said). If I walk the whole way I'll be totally soaked when I get there, so I'm looking for just enough to purchase bus fare. Do you have a dollar to get me started?"

Assuming he was telling the truth (I give people benefit of the doubt -- sometimes to my own detriment) I found it a legitimate reason to ask for money. I had cash on hand so I gave him a dollar. He was grateful, he thanked me and wished me well on my day.

The bus was another minute away. I watched as he went up to other people to ask them for a dollar. They all either acted like he didn't exist, said no, or said "I don't have any money."

I turned to him and said,

"Hey -- tell the next person what you told me then point to me and say, 'that guy was able to give me a dollar, do you think you could do the same to help me get on the bus?'"

My #20 bus pulled up, and as I waited in line to board, I saw him talk to someone then point to me. They gave him a dollar.

The lesson here?

When you pitch your customers or investors, leverage social proof. When we see others like us doing things, it makes that next person more likely to act. The better you're able to say 'Another person/company just like you is doing this', the better opportunity you have to win them.

Just trying to book meetings with potential customers? What works almost every time is when you get a meeting with one person, call up someone in their geography to say, "I'm going to be in the neighborhood already..."

If it can get a homeless man a second dollar, what could it get you?

Did this make you think? support your ecosystem and pass it on to another entrepreneur.

Stay Hyped!


Rajiv Nathan