After a few weeks of home business lessons from the sex shop and home business lessons from the tattoo parlour, it’s time for another one. (I had a request to do a brothel next, but even I don’t know how to track down one of those. Southwestern Ontario is not known for its liberalism.) Therefore, without further ado, here are 5 home business marketing lessons from the homeless dude:

1. Ask for the sale.

You know when you walk by a homeless dude on the street and he’s sitting there with a sign that says “Spare some change?” You know how he never has any money in his cup? You know how you see him there every damn day? He’s there every day because NOBODY’S GIVING HIM ANY MONEY.

Takeaway: Don’t be the dude with the sign and the empty cup. Don’t just post a classified ad or hand out your business card and assume your marketing job is done. It ain’t.

2. Be specific.

I don’t know about you, but I am much more inclined to give money to complete strangers when they have a good reason for wanting it. Like, “My mother just died and I have to get on the next bus to Tulsa or I’ll miss the funeral” or “I’d really love to get a sandwich because I haven’t eaten since Sunday”. Much more likely to make the sale than vague begging.

Takeaway: Tell me what you want me to buy from you and I am much more likely to buy. You do not provide “business solutions” or “quality technology” or “positive results”. You provide dog walking or web hosting or cheese graters.

3. Bark up the right tree.

If you’ve been homeless for a while, you know who is likely to give you money and who isn’t. Certain demographics don’t carry cash. Other demographics don’t have cash to carry. Still more demographics won’t talk to strangers at night no matter how compelling your argument.

The other night I was walking home from the IttyBiz Branch Office — otherwise known as Coffee Culture on Dundas Street — and a guy asked for money. It was dark and he was standing in a not very well lit area and I wasn’t carrying my wallet. I wasn’t carrying a purse, either. Just me, my laptop, and my debit card.

He practically jumps out at me and asks for money. I am a young woman walking alone at night… is that really the best way to start? There is no visual sign that I have money on me and now I’m afraid of you. Um, no. Bad prospect.

Takeaway: Qualify your prospects. Certain people don’t buy. Certain people act cheap. Certain people adore you but can’t afford you. Pay close attention and view the trends.

4. Don’t be a prick.

Speaking of the jump-out-of-the-night dude, I tried to be nice. I said, “I’m really sorry. I don’t have any money on me. Good luck, though.” (I’m much nicer in person than I am on my blog.)

Dude totally lays into me! As in, “Look, lady, I work hard and I’m not out here every night and I just need some fucking money for some dinner, OK? You don’t have to be a bitch about it. A buck woulda been fine.”

That’s when I stopped being nicer than I am on my blog. My mother reads this so I won’t tell you what I said but to the outside observer it looked a lot like me ripping my debit card out of my pocket and waving it in his face yelling, “Are you calling me a liar? Look, fucker! This is what I have! Will this help you?”

Takeaway: I think the takeaway here is obvious.

5. Never doubt the power of the USP.

When my first husband and I moved to Toronto, we were shocked by the amount of people asking money on the street. Not shocked like morally opposed — there were just so many more people there than we were used to. More people than any one person could possibly help. (This is called market saturation and it’s very similar to the web design industry these days.)

People think that you can’t succeed in a saturated market and that’s total bullshit. Many succeed. But they’re the best, and they’re usually the unique ones.

Example One: My ex and I are walking down Queen West and a young man asked if he could make us a bet. He held up a loonie — that’s a dollar for those of you south of the 49th parallel — and said, “I’d like to bet you a dollar that I know where you got your boots.”

Since my ex had owned the boots for seven years and had bought them in a different city, he felt confident about the bet. “You’re on.”

The young man makes a huge show of thinking and posturing and generally being hilarious. (Picture someone who looks like they fell out of a Sex Pistols show with two fingers to each temple looking like he’s thinking so hard he’s trying to conjure up the dead.) Finally, after about a minute, he has the answer.

“You got your boots… ON YOUR FEET!”

Example Two: I used to go to a downtown college and as I was walking to the subway one day, a girl looked up at me from her sidewalk spot and said, “Excuse me, miss? Can you please spare $2.29 for kitten food?” Sure enough, right beside her is a kitten on a leash.

In both of those cases I don’t care if they used the cash to buy cocaine solely for the purpose of doing lines off a Tijuana hooker’s abdomen — they got the cash. And I’m pretty sure they weren’t the only ones.

Takeaway: Don’t be like every other loser. USP, people. USP.