I just gave a homeless guy $8.50

Why?

Because I’m nice?

Because I’m tired?

Because I’m travelling alone and felt like a little conversational companionship?

A combination of the above maybe but they’re not the real reason.

It’s because he put the hard sell on me.

$8.50 is nothing in the grand scheme of things. I’m sitting in a flash restaurant writing this, the kind where people wear their nice shirts and say things like, ‘I’ve been so busy lately!’, then spend 6-hours sipping $15 drinks.

I’ve been here for 3-hours (4-hours now) ordering food to chew up time. I do not fit in. I’m wearing shorts and sneakers and have my bag of crap with me. My bill will be 5–6x what I gave the homeless guy.

The front of the restaurant was a little dirty and dark. It didn’t look open so I hesitated to walk in. That’s when he struck.

‘Excuse me sir, how are you doing today?’

I was already facing him.

‘I’m doing great thank you, how are you?’

‘You look it! And let me ask, did your parents raise you well?’ He spoke through his toothless front gums.

‘They did, I’m very lucky.’

‘I can tell because you stopped to say hello to someone below you.’

‘No one is below me.’

His skin was darker than mine.

‘And I can tell you’re not a racist because you’re talking to me.’

This I didn’t care about. I talk to anyone the same. But the first two lines are what you should pay attention to.

Within 15-seconds of meeting me, he complimented me, twice. Once directly and once indirectly.

Directly by saying I looked great and indirectly by asking if my parents raised me well. They did.

‘Sir, my name is Thomas James.’ (Changed name)

‘I’m Daniel.’

‘Nice to meet you, Daniel,’ he said ‘now I’m looking for someone like you to help me.’

I kept listening.

‘Are you hungry, Daniel?’

‘I am.’

‘Well me too, and I’m looking to fill my tummy with some hot wings down the street.’

I half thought about saying let's go and get them together. But I didn’t. He kept going.

‘I can get me a serving for $8.50, would you be able to help me out with that?’

‘$8.50 hey?’

Notice the very specific amount.

‘Yes sir, I’m going to get me some wings, fill my belly and go over under the bridge to sleep,’ he was smiling, ‘oh man, I can’t wait!’

‘Where are the wings?’

‘Down there on the corner.’

I walked closer to the street to get a better look.

‘Where you from, Daniel?’

Making the conversation about me.

‘Australia.’

‘Australia, how you liking Cleveland?’

‘I just got here today.’

‘Well I been here close to 49-years, it’s my birthday soon,’ he was enthusiastic, ‘I’ve got holes in my shoes but I’m hoping to get myself some warm socks soon.’

Letting me know a little bit more of his story.

‘Okay, let me see what cash I have.’

I had $8 in my pocket, a five and three ones. I’d been carrying it around for the past few days. I’m a card operator. Cash is rare in my world. I pulled it out and handed it to him.

‘Daniel, you’re the best. This is incredible. I’m nearly going to have a full tummy tonight, all I need to do is find $0.50 more.’

$0.50 sounds like not much more on top of $8 but it’s 6.25%.

I knew I had $0.50 in coins somewhere. I fumbled through my wallet and handed him the extra two quarters.

‘Oh wait, I think the chicken was $9.50.’

The only slip up he made.

‘No, no, you said $8.50, have a good night.’

‘Bless you Daniel.’

Who knows where he’s going to spend the money. Food, cigarettes, new socks. I hope he gets the wings but I don’t care, it’s his now.

What can we learn from Thomas James?


A) Make it about the other person

When he started the conversation he made it about me.

‘Were you raised well?’

‘Are you hungry, Daniel?’

As it turns out, I was raised well. And I was hungry. Walking into the restaurant probably gave it away.

He appealed to my interests first, not his own.

If you want to get someone on your side, make the conversation about them.

How does this help sales? It helps because you’re far more likely to buy something from someone you like than someone you don’t.

Thomas got me on his side.


B) Be specific

You’ve seen the signs homeless people hold before.

With writings like any loose change?’, and there’s a cup out front.

People don’t understand vague ranges very well.

Any loose change is vague.

It’s the same problem as when you go to an ice-cream store and can’t choose a flavour. You’d think so many options would be a good thing. But too many choices and you end up with none.

Thomas James didn’t ask for any loose change. He asked for a very specific amount. $8.50 for chicken wings.

This means instead of having to think through all the different amounts of money I possibly had on me, all I had to do was think about $8.50.

This is what Apple does very well. When Steve Jobs returned in 1997, his first mission was to reduce the number of product lines from 21 to 2. Less but better. You know what happened next.

If you want someone to help someone make a decision (like buying something from you), reduce their number of options.


C) The little bit extra

I could’ve handed him the $8 and left it. Close enough.

Then he hit me with the upsell.

‘Now I only need $0.50 more to fill my tummy.’

If he didn’t say this, I would’ve walked off.

An extra 6.25% doesn’t sound like much. And it isn’t on individual transactions. But over the long run it adds up.

A $100,000 investment with a compounding interest rate of 6.25% turns into $183,000 after 10-years.

The upsell philosophy happens a lot at car dealerships. When you’re buying a $20,000 car, dropping $1,000 more on some extras doesn’t sound too bad for you but it’s great for the car dealership. Why? Because they make 10% profit on the car but 80% on the extras.


Homeless people have to be good salespeople. They have to sell for survival. Or drugs. Have you ever seen an addict go without a hit? It’s not a good time.

I could be over analysing this. Maybe I needed a reason to justify giving $8.50 to Mr James. Maybe I’m too easy. I gave Ink Stain $5 in San Francisco he was writing his first book and wanted to get it published, I said he should try Medium.

But I like to think Thomas is warm under a bridge with a stomach full of wings. And after reading this you’re a little better at sales.

After Thomas walked off, I walked inside, sat down and ordered myself a plate of wings. They were $12.

I didn’t book accommodation tonight. I’m catching a train across the country at 2 am. Maybe I’ll be the one under a bridge with a stomach full of wings.

Or maybe I’ll use Thomas’s tricks to convince the bar to let me stay until they close. We’ll see.


This post originally appeared as an answer on Quora.