lessons on outbound lead generation from the homeless

Lessons on Outbound Lead Generation From the Homeless

Two months ago I moved from the land of the Oil (Edmonton, AB) to the land of hipsters and rain (Vancouver, BC). I’ve been told that Portland might actually win that contest but only on account of facial hair. The reason for my move had less to do with struggling oil prices and more with the promise of a tech hub without having to get sponsored for a work visa.

In such a short time the city has not disappointed, there is definitely a lot going on here. I’ve seen the inside of some of the most impressive offices in tech, witnessed excessive wealth that would put any rural suburban to shame, and even took part in a few of the countless outdoor activities the city has to offer. The wild thing is that even with all of this going on, the most impactful thing about this adventure so far has been the homeless in the city.

You might expect that their situation here has increased my gratitude or made me appreciate my health more, which it has, but more than that it has made it apparent that everyone is a salesperson the only difference is their levels of success. I might not have came to this realization but by chance I walk by different groups of people to and from my car everyday (good luck finding parking in the city). Typically I steal a technique from the hot girl walking through the mall by herself; headphones in, eyes at the ground. But this particular afternoon I couldn’t help but notice this lady hunched over next to a power box just off the sidewalk. Not to be rude but this was less of a grade 9 unit test hunch and more of a Dufner.


It wouldn’t have been all that out of the ordinary except I look on her lap and there’s 3 freshly scratched lottery tickets…


[WPGP gif_id=”1861″ width=”600″]

I’ve been guilty of playing them before too but man, that hit me hard. Someone so delusional or overwhelmed by their current situation that they feel the best way out is sheer luck. In fact, Peter Voogd says in this article that 1 in 3 Americans believe their best chance of becoming wealthy is winning the lottery. The thing that was so crazy to me was she wasn’t trying to get rich, at least I presume she wasn’t, she was just trying to get by.

It was a horrible scene but the biggest thing that I took from this lady and her utterly defeated body language was it’s relation to sales. I thought back to all of the different homeless people I’ve seen in the city and their different approaches to improving their situation. It quickly became clear that there were three very specific things they all did differently which determined their level of “success” on the streets. These things have a shockingly similar impact on the level of success of any given salesperson, especially in outbound lead generation roles.

    1. They Drove Demand.

These people test variants the same way that you and I look at landing page copy, except the stakes they’re dealing with are MUCH higher. I’ve explored the city enough to realize it’s no fluke when you see someone at a specific corner at a specific time. For example, waterfront mid afternoon might have a lot of foot traffic but wait a couple hours and people will be pouring out of their offices in Gastown. It’s for this reason as the day progresses you’ll see the same people migrating East with their collection cups.

Ironically, the people that are chasing the traffic, quite literally, aren’t the ones that seem to have the most success. It’s the people that are able to draw a crowd that I’d assume are making enough money to at least feed themselves. So who pulls the biggest crowds? Well we’re not talking Rihanna in Stade de France here but believe it or not I’ve seen 20-30 people huddled around some make shift drum kit in the rain. Obviously these people aren’t celebrities but they have gained some specific talent. For example maybe they know a simple magic trick or they’ve nailed how to play Wonderwall on a guitar but they also take the time to interact with people. Most effectively, they’ll stop, get the kids involved with singing, or touching the coin/pencil/rubber ball that they’re going to make disappear. And once your kid is having fun as a parent it’s over, you have to fork over some cash

The way that I apply this to a lead gen strategy is that if you’re using the spray and pray approach, sure you’ll get some quarters in your hat but can you really call that a success? The equivalent of that technique is the guy that’s got his head down and a cup out, maybe a cute dog beside him in a fairly high traffic area. Sure, if you get the same person to walk by you 25 times you might guilt him into a couple bucks but surely not enough to make a living off of. You need to give people a reason to interact with you, get them involved, make them feel good, teach them something, just don’t expect results with no effort.

    2. They Provide Some Type of Value.

Have you ever thought about what your “schtick” would be if you found yourself on the street? I have this debate with my friends all the time. I’m convinced that I’d be a freestyle rapper. That’s not even a joke lol. You target your “product” at each specific group of people, that way you broaden your appeal while also being novel and unique. With the price of housing out here I may have to watch 8 mile a few more times just incase.

The best examples I’ve seen to date of people offering value are the ones making bold claims. However menial the claim might be it’s bold and will work on a certain amount of people. “I will guess your age!” “I can read your mind!” “I can predict your future!” These are the exact same tactics Internet marketers are using to get their ads clicked on, and they work. The point is you don’t necessarily need to pay for the best real estate but you do have to show up to bat with your own bold claim. Whether or not you can follow through on that claim will determine your long term success. I’m not kidding about long term success, I’ve seen on multiple occasions people be “repeat givers” to certain homeless people where it seems rapport has been built. In one case I’ve witnessed two older ladies take a younger person under their wing to try and help her on a more long term basis all because she was able to build a relationship.

I don’t want to support the people that are self proclaimed “experts” without any tangible results but I definitely respect the guys claiming to be the best in their industry and backing it up with confidence. Why not? If you hear someone say they are the number one person in a specific market over and over again will you at least give them the benefit of the doubt and check out their stuff? I would. Be bold! Make big claims. Then follow through on them.

     3. They Capitalize on Timing.

Not only do people on the street think about where and when to look for their best customers but they craft their pitch based on context. Think about the last time you gave money to a homeless person. I’d be willing to bet that it had more to do with what was going on in your life than anything else. Everyone has had that feeling where everything seems like it’s finally lining up for you and your hard work is paying off. If someone propositioned you in that moment you would be 100x more likely to give some money.

I’ve heard people reference the time of year, the upcoming holiday, the weather, the election, whatever gives them the most context in that very moment. Then of course if they can’t come up with anything or are just feeling lazy they might drop the karma card on you. I don’t even blame them, I’m sure that works sometimes. The timing of any lead generation effort is likely the most important factor. I’ve had numerous circumstances where I haven’t replied to people not because I didn’t intend on it but just because other things came up before I had a chance to get back to them. Consider the person you are trying to contact and where they might be in their day when you’re trying to get ahold of them. I know that successful people are up early and if you can find your way into their inbox they are usually spending some window of time between 7am – 10am in their email at a desk. Those types of people also like to get things off their plate instantly so it wouldn’t be uncommon to get a quick response at that time. However if you try to email them at lunch or dinner they are likely out with friends or colleagues and under so much time pressure that they focus on being present as much as possible which means they have their phones off or on silent (eg. no response/instant archive).



In short drive demand by giving people a reason to come to you, after you have their attention deliver on your value promise and leverage timing for best results. I see it everyday used to varying degrees of success on the streets yet I know people are firing off hundreds or thousands of emails a day hoping for some action while offering nothing in return.

At some point it became OK for us to send those mass emails with the exact same copy hoping for someone to drop their change in our guitar case. If you think about that in this context you’re the guy on the street yelling “HEY! Blue shirt! spare change? spare change?” You’ve scoffed at that person before but change the context and it’s fine because we’re just “playing the numbers”.


Of course there are always different ways of doing business but personally I value impact and relationships over balancing churn rates with email deliveries.

Ultimately I hope this is a catalyst to do better, raise your standards and actually take interest in the people you’re prospecting. Do a little extra research before you get on that next demo. Learn about their business, find out what the person is interested in or what’s going on in their world. Take five seconds to make a personal connection and actually be authentic! You will be way more likely for that person to reciprocate your energy and at the very least give you their attention.