Sales 101 - What I Learned About Selling From Crackhead Bob

After quitting my job as an insurance underwriter I needed work. Anything was better than where I was working. I called a friend and began working for his asphalt sealing company right away.

My first day on the job I met the company’s salesman.“Hi, I’m Crackhead Bob, you’ve probably heard about me”. Before I had heard of Jordan Belfort, Grant Cardone or Joe Girard, Bob was a successful real estate agent pressing flesh and cashing cheques. In his heyday, after landing big commissions then later feeling invincible, Bob began to experiment with drugs which eventually led to him becoming addicted to crack. Despite what many of us have come to believe about crack users, Bob never had to lie or cheat to make a sale. He had ethics. I watched Bob knock on door after door, closing sales in situations that looked hopeless and Bob left smiling, with cash in hand. Bob was a weapon.

After watching Bob knock on countless doors and converting most prospects into sales, I needed to learn. I asked Bob how he did what he did.

Selling Yourself

Bob said the first sale you make is yourself. People buy from people they like.

Enthusiasm was key.  In the sales classic “How I Raised Myself From Failure To Success In Selling” the author Frank Bettger said “I firmly believe enthusiasm is, by far, the biggest single factor in successful selling”. Leave customers feeling better for having met you.

During the time I worked with Bob, I never heard him complain except to tell the boss that he isn’t lifting anything heavier than his clipboard because that’s work. Moods are contagious. If you’re feeling upbeat, despondent, angry or euphoric others will sense that and will change their mood accordingly. Lower the customer’s energy or mood and you lower the odds of closing the sale.

I never heard Bob use tentative words like “sort of, kind of or maybe”. These words tell the prospect that you are uncertain or lack confidence in what you’re selling. The words we use account for a small percentage of our communication, most of our communication is nonverbal, several experts have estimated words account for seven percent of our communication.

Bob didn’t look like a typical salesperson. No fancy dress shirt, slick shoes or Gucci belt. “Antifragile" author Nassim Taleb said “now there may be some correlation between looks and skills; but conditional on having had some success in spite of not looking the part is potent, even crucial, information.” Because Bob was successful at what he did and he didn’t look the part, his actions and insights were worth paying attention to if I wanted to improve my sales game.

Appeal to Emotions

“Bypass their logic” Bob told me. Don’t ask the customer what they think about something, appeal to their emotions and ask them how they feel about it". People buy on emotion, they buy things based on how they think these things will make them feel. Most people don’t truly need their driveways sealed or paved. Bob told prospects that their driveways looked terrible compared to their neighbours and asked them how that made them feel.

We don’t need that sports car with 400 horsepower, custom jewellery, a state of the art barbecue. A lot of our purchases aren’t sensible. We buy these items because we think it these will make us feel better for various reasons.

Complaints Are Often Opportunities In Disguise

Bob once said to me that he likes when customers complain to him because he gets more money from them. What? I was thinking drug use had gotten the better of Bob. Who in their right mind wants to deal with customer complaints? Within 20 minutes of Bob telling me how he always gets more money from the customers who complained Bob had a customer walk up to the truck we were sitting in and complained to Bob how he wasn’t happy with the job we had done on his driveway. Bob walked over to the customer’s driveway and upsold him on having a patch job done to level out the corner of the driveway. Bob walked back to the truck where I was and said “see, I told ya”.

Most business is transactional. A customer pays a price for a good or service and receives the good or service as expected, nothing exceptional transpires. When a job goes wrong or a customer becomes angry there is often a window of opportunity to flip the emotion. If a customer becomes angry and you go above and beyond to make the situation right you can often gain a loyal customer for life. A real measure of a business is how it responds to mistakes.


Bob used to say “God hates cowards"

Door to door sales can quickly become a demoralizing way to make a living. This style of selling isn’t for most people. One needs the ability to mentally let go of the previous interaction and not let any of the residue from that conversation poison the next.

I recall one occasion where Bob knocked on a customer’s door and a lady had answered. Bob tried to tell her that her driveway needed attention but he didn’t have a chance to get any words in. The lady had shouted at Bob that he wasn’t allowed on her property and that she doesn’t want to be bothered by any door to door salesmen then slammed the door. Bob’s audacity came in handy. Bob walked around to the side door of the house and the same lady had answered the door. Bob told her there was a Bitch who lived in the front of the house and explained how cold she was when all he wanted to do was tell her that her driveway needed to be repaired. Bob sold her a paving job worth $2000. I couldn’t believe it.

Bob was fearless. He had to make enough cash every day to support his habit and pay his living expenses but Bob knew when to back off. Pushy salespeople are amateurish, a pro listens more than they talk to understand what prospects value. Bob also believed everyone was closable. This was an empowering belief that gave him the mindset needed to stay the course when dealing with intense objections and rebuttals.


When we fail to make a sale or things don’t turn out as we had planned we need to ask ourselves why. We need to be honest with ourselves. No outcome is wasted if we take the time to learn from it. People don’t always tell you the real reason for their objection. Listen intently when you qualify the customer, what is their pain point?

Occasionally mentors or teachers will come into our lives in various forms. If we're curious, lucky and observant we can recognize them when they appear.