Sales Lessons 101 From a Homeless Guy

I just gave a homeless guy $8.50.

Daniel Bourke
The Startup
Published in
5 min readMay 17, 2019

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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.

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