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John DeMato Blog

Welcome to the Deliver Magic blog, where experts who speak, coach, train, consult, and write books will find actionable insights to elevate their personal brands through visual storytelling. From strategy tips and branding photography to live event coverage and storytelling techniques, discover step-by-step guides designed to help you align what you say with how you show up in photos. Get ready to unlock the magic behind creating a cohesive visual identity that drives engagement, builds credibility, and inspires your audience. #DeliverMagic

Portrait Session Tailor-Made For A NY'er

 

Portrait session tailor-made for a NY’er…

 
 

…it’s the least I can do for him!

 

When you work for yourself, it can, oftentimes, be a lonely place.

It’s not that you are on an isolated island with no one available for help, but, it’s a mindset that you have to channel in order to maintain productivity and focus.

As a way to catch a break from everything, I seek relaxation and downtime in podcasts - specifically, comedy podcasts.

One of the podcasts that I listen to religiously is the I Am Rapaport podcast because, quite frankly, it’s a couple of New York guys talking shit the same way I do - so, you know, I appreciate that, :)

It’s just a great way to shut my brain off for a few hours and just enjoy the conversation.

It’s become a staple in my day-to-day life.

And this is why I reached out to the I Am Rapaport show co-host, Gerald Moody.

I saw a post of his on Instagram one day, and decided to reach out randomly through direct message, thank him for all the wonderful work he does, and offered my services as a way to help promote the show.

To my surprise, Gerald responded and not only thanked me for tuning in, but, took me up on my offer to create an image content portfolio that he could not only leverage for his work on I Am Rapaport, but also to promote his solo podcast, This, That and a Third With G Moody.

Awesome!

Then, we got to work with a pre-session strategy call that went over the specifics, including locations, outfits, and types of portraits he wanted to capture

After consulting with him for over 2 hours, we came up with a plan revolved around showcasing his love of his hometown by shooting all over NYC.

Boy, did we have a lot of work to do, but, it sure as hell was going to be a lot of fun…

...and it was!

Let me show you what we created, :)

A VIEW FROM THE BROOKLYN BRIDGE

Originally from Brownsville, Brooklyn, Gerald was adamant about capturing portraits on the Brooklyn Bridge, and, how could I argue with that?

The only challenge for me was to figure out how to capture portraits in a location that has so much constant foot traffic that I had to get creative with framing people out so they didn’t distract from the main subject of the photos.

After toying with how I wanted to position Gerald on the bridge, I started snapping away, forgot about the 90 million tourists breezing past us every 20 seconds:

As we looked at the photos, Gerald mentioned that he has always wanted to get photos of himself on the bridge, and now he was excited to actually have done it.

Yes, these photos are wonderful to leverage as promotional shots, but, the personal component means a lot to me, and I was psyched that I was able to provide him with these memories that will long outlast his work on the podcasts, :)

NEXT STOP - THE NYC TRANSIT MUSEUM

One of the other “must haves” for Gerald’s image content portfolio was to incorporate images of him on the train.

As a fellow NYC kid, I completely understand his line of thinking because the transit system is iconic and it’s a huge part of getting around the city without a car.

It’s deeply ingrained in our DNA - even though we spend most of our time being pissed at it for being late, :)

Gerald mentioned to me in the days leading up to the session that he wanted us to go to the Transit Museum because they had old train cars, and since these were out of service, we didn’t have to worry about shooting around pedestrians sitting and standing in our way.

Awesome - I like uncomplicated, :)

So, we spent about an hour working our way through a variety of old train cars that spanned over 100+ years, and I have to say, I see myself making my way back there to just enjoy the place.

ALL I WANTED WAS A COFFEE BREAK!

Once we finished up at the Transit Museum, we jumped in the car and headed to his home in the Bronx to capture some candid portraits of him podcasting, but, before we made it there, I was dying for my afternoon coffee.

On the way, we stopped at a local spot in West Harlem, and, as I was sipping on my gigantic, iced coffee, Gerald and I took a walk down the block, and something immediately caught my eye - a stoop that has his name written all over it!

Another NYC staple is the stoop - it’s where our parents allowed us to hang out when they weren’t directly hovering over us. I love photographing clients on stoops when they want to capture some NYC flavor in their portraits, and with Gerald, it was certainly on our list of “must haves.”

Once we saw the stoop, and how it perfectly complemented what he was wearing, we were ready to go to work…

...that is, once we bribed the guy who was sitting on it already to move - thanks again, Carlito, for being so flexible, :)

Another attractive element of this location was the fire escapes that hung over our heads - another NYC visual staple that was on our list of stuff to include in the session.

So, I had Gerald stand up, and I laid on the concrete and we experimented with that visual element for a couple minutes:

Once I dusted myself off, we walked down the block, and voila - another amazing opportunity presented itself!

There was a storefront gate with musical equipment spray painted on it, and, since part of Gerald’s brand is his love of making beats, this was an ideal spot to grab some portraits, as well.

Now, up to this point, this block that we just so happened to stumble upon was providing us with ideal locations that was on our list of locations to identify and shoot.

It allowed us to accomplish a lot in a short amount of time, so, Gerald seized the opportunity to piggyback on our newfound momentum by going off our shoot schedule to capture something off-the-cuff.

Next door to where we were shooting is a hair salon. Gerald suggested that we go in there and snap a couple fun shots of him sitting under a hair dryer. Although he’s bald, he’s a comedy podcaster, so, of course I want to capture shit like that for him!

It was about 900 degrees in there, and I barely had any room for my light or me, for that matter, but, I wedged myself in between a couple sinks and made it happen.

The photos were funny so it was worth the effort, :)

As we made our way out of the salon, I thought we were done with this block, but, sure enough, I was wrong.

Just when I thought we couldn’t squeeze any more magic out of this street, Gerald and his girlfriend noticed a bar up the block that had a really cool mural painted on the back wall.

It caught both their eyes, and since I had a camera and a light in my hand, why not go in and snap a few, right?

So, within the span of 30 minutes - and one cup of coffee - we managed to check off 5 distinct locations and activities in one city block.

Although it was a stroke of luck to get this amount done in one fell swoop, had we not discussed the types of portraits we needed to get beforehand, these opportunities would never have presented themselves in the way they did.

...funnily enough, I would’ve been happy with just the coffee, :)

GOING BACK TO WHERE IT BEGAN

I was introduced to Gerald through his work behind the microphone, so, I was really excited to capture images of him doing his thing.

It’s one thing to hear someone’s voice - it’s another to see them perform...

…and he sure didn’t disappoint.

12 hours and 4 boros later, the session was a wrap.

Although a ridiculously long day, you couldn’t wipe the smile off my face even if you tried, :)

Collaborating with someone who provides me with such an enjoyable escape on a daily basis was just about as awesome as it gets. It was so fun that we were already talking about Round 2!

Of course, there is the matter of leveraging the hundreds of photos that we captured during Round 1 first, of course, :)

Either way, days like this remind me why I do what I do, and why I serve who I serve, :)


PS - For those of you who aren’t in the know, I mail out these blogs 3x a week, and lemme tell you, they’re a real party, so, if you’d like to get in on this, sign up for it here and I’ll throw in a free gift for you, because I care, :)