For all of the talk I do about social, marketing, and legacy, what gets passed over is the fact that I’m a salesman at heart. Before WLTV, before VaynerMedia, before

VaynerRSE, I developed my chops and my fortune by selling stuff.

With that in mind, I’m putting out a series of pieces about sales. From my personal experiences, to “what it means to be a salesperson.” It’s something that’s really important to me, and I want to speak more about it.

Read more:

Pt2: The Dark Side

Pt3: Disrespect for Customers

—

Pt. 1: Selling Wine

By the time I started working at my family liquor store at the age of 15 I already had a (crazy) 10 years of sales experience under my belt. A lot of people have asked me who I learned from, or where I picked up my technique, but the truth is that I was very independent about it.

I spent very little time studying what other people on the floor were doing or patterning any of my behaviors off of them. At that point I had over 50 baseball card shows under my belt, and I already thought I was a better salesman than anybody in the store.

That said, I did my homework. I’d read the back of the wine bottles and the display signs. Maybe I’d ask Dick (our head wine guy) some questions. I also spent a lot of time educating myself with industry publications like Wine Spectator. For me it was no different than reading the Beckett baseball card price guide.

I’d pay a lot of attention to how customers would sell the wine to each other. They were really good at it, too. People are more attracted to advice from someone who doesn’t have a vested interest in selling something to them, and I realized that authenticity had a lot of value. I can even remember imagining ways to come up with fake customers and take advantage of it (for the record, I never pulled that one off).

I think I’m a great salesman because I listen.

It’s behavioral. I’m hunting. I pay attention to what people do and look for patterns. I think of conversion in an emotional more than an analytical way. My style was always to ask questions:

“Hey can I help you?”

“Yeah I’m looking for some wine for a party”

I’d never just respond with a recommendation, I’d keep asking questions. I think it’s the same reason I do well on Twitter. “What kind of party are you having? Is it your boss, or someone you’re trying to impress? Because then maybe we should go in the direction of a name brand. Oh it’s just your buddies coming over for the NFL draft who only drink beer and don’t know the difference? Here’s an $8 wine that acts like a $15 wine.”

And, of course, I was hyper, so I’d speak quickly and throw out four different scenarios in a two second period. “For a party? For a boss? For Friends? For a date?”

I wasn’t asking questions in order to get permission to talk. If I wanted to talk, I would just steamroll you. The questions were there to reverse-engineer your needs and provide the insight that I could deliver on.

Here is what’s fascinating about selling wine:

1. People are intimidated by it.

2. It’s all based on stories.

3. It’s a commodity.

Sure some Pinot Noirs are better than others, but in all honesty there are very few people who can taste the difference. So now you’re in full storytelling mode. Now you’re playing on the emotions, and the stories of the vineyards and the winemakers.

As an artist — and that’s what I consider myself as a salesman — it offered me a wide canvas to paint on. The only things I really had to navigate were the ratings by the the big reviewers, but outside of that, I had free reign, so I painted a lot of pictures.