Street Portraiture - Beyond the Natural Light [Portrait]

Last week I watched a very inspirational video [Link is Here] not too long ago which featured Joey Lawrence, a fantastic photographer from Canada now living in Brooklyn.  Joey is a bit of a phenom, he's incredibly talented and very young.  His images boggle the mind with light quality and intrigue.

Like many photographers, I want to be like Joey.  I spent a bit of time learning how he sets up lighting for his portraits and found out that he will make use of artificial light even in the depths of a jungle somewhere, to make sure his subject looks amazing.  He also uses a medium format camera which helps to give his images incredible sharpness where focus is on and a bokeh that melts away where it isn't.
Leo

While I don't have profoto heads or battery packs, or a medium format beast camera I did my best to hit the streets of my own city and tried my hand at making portraits of people I just met.  I wanted to have the end result look like they were commissioned works; they should be compelling and well lit, but not so much that the layperson would suspect something wrong with the exposure.

Lighting? I used three flashes in a Westcott Apollo Orb softbox.  The big soft light will flatter most people, and it helps to emulate the deep octa box that is used by so many photographers nowadays.

Robyn and Eli
I want a shallow depth of field to emulate that medium format look, or at least to give my subject some extra isolation off a backdrop.  Three flashes, and a daylight exposure? Hmmm, I'm going to want to push the ISO down to 100 or even 50 when I can.  Manual flashes? that means my shutter tops out at 1/200 of a second, but really it tops out at 1/125 to be on the safe side.

Jamal
Secret weapon: 3 stop neutral density filter.  I bought it to make water look silky, but it might just come in handy here.  With it I am able to shoot with an aperture of about f/4.0 or wider while keeping my shutter below 1/200 of a second, which should provide the soft bokeh in the background when I shoot with my 50mm lens.

Ahmed
I learned a lot from this approach.  I found that people were very receptive to have someone take their photo if the photographer had an assistant toting around a massive softbox. Maybe it looked more professional or something.  I learned that it's possible to be out on the street and shooting a portrait while taking control of the light, and making it work for you.  I also found out that my ND filter is a great tool to manage exposure.

Best of all I learned something new about some people in my city.  Halifax is such a wonderful spot full of wonderful people.  It will be a sad day if I should have to leave, because by walking the street and talking to the people I've found myself quite welcomed, and it's an amazing feeling.