Up On the Roof


Real Estate marketing tends to be, well, conservative. To put it mildly. In fact, when I look at the marketing collateral (in which my images are often featured prominently), they tend to look as if they were designed in the mid-80’s.

So I was stoked when one of my long-term clients, Michael Thompson, asked me to shoot a series of photos for his new self-promotional brochure. Michael wanted to avoid all the clichés that dominate his industry. He also wanted a very photo-centric brochure, with a minimum of text. Finally, he wanted the images to be evocative, even startling, and he didn’t necessarily want to be featured prominently in any of them.

Very, very cool. (rubs hands together)

A series of creative meetings ensued, with Michael, myself, Quentin Bacon (who would be doing graphic design and video), Donna Hanson (who does freelance marketing consulting), and Adele Wong (who did the writing). Michael was open to pretty much any idea that was pitched, and over the course of many hours and lots of coffee, we considered dozens of ideas, including some truly wild ones.


Left to right: Michael, Adele, Quentin

One of the most common photos in real estate is the portrait of the agent standing in the half-open door of a fabulous house, like the butler welcoming the Viscount home from the opera. That was the last thing we wanted to do, but still, we needed an opening shot that placed Michael in the context of real estate, and grabbed people’s attention.

My idea was to turn the “doorway” shot upside down, and place Michael, in suit and tie, on the roof. The message is that he’s different from the crowd (“Whoa. Is that guy on the roof?”), and also places him in a superior place, ‘on top of things’.

Michael and I spent an afternoon driving the neighborhood he specializes in, and between Michael’s endless anecdotes about the history of the neighborhood (this is the area that burned in 1991), we looked for good rooftops. This involved repeatedly knocking on the doors of total strangers and asking if we could conduct a dawn photoshoot on the roof of their house. We got a few blank stares, but no one, NO ONE, turned us down outright! In my experience, the wackier the proposal, the more likely it is to be accepted. If we had asked if we could shoot a simple headshot on their front lawn, they probably would have called the police. But put a guy on the roof, wearing a suit and doing email? No problem.

In the end, the winning location was a former client of Michael’s. I made some scouting photos, and we talked with the homeowners at length. I was surprised at how open they were to the idea, until I learned that their kitchen has been the location for several Pottery Barn photoshoots, productions that made our little project seem quaint by comparison.

We scheduled the shoot for a Wednesday morning. I arrived at about 5:30 a.m., and the rest of the crew trickled in soon after. I wanted the dawn light because the shot would feature (depending on the angle I chose) either trees/rooftops or the classic SF Bay view as the backdrop, and that’s a west-facing view either way. Had we shot this in the evening, I’d have been shooting directly into the sun. I wanted to utilize the sweet, warm light of twilight, which meant an early alarm clock and the “other” twilight! Quentin set up his video equipment, and Michael and I went up to the second-floor balcony that we were using for access to the roof.


The tiles were pretty slippery, and we didn’t really want to test out the $2 million insurance policy I had taken on the property, so Michael went across the roof barefoot (to protect the ceramic tiles), using a towel to keep the moss and dirt off his suit. Once in position, he put on his shoes, opened up the laptop (my old one), and we waited for the light to get “right”.


I made some shots from the balcony, but the real prize was going to be the photos made with the San Francisco Bay as a backdrop – in this area, that view is immediately recognizable and would really anchor Michael in the neighborhood.


Shooting from the roof of my car, I was able to shout instructions to Michael (no doubt the neighbors were amused) and over the course of the next hour or so we made a series of photos:

The straight-up portraits are interesting, but to my eye, it’s the ones with the laptop that really make the statement. Why is he on the roof with a laptop? That little element gives the photo much more depth, and engages the viewer in a way that the others don’t.
By the way, while the drop off the near side of the roof was only one story, the drop off the back was two stories, onto a very steep canyon rim. It was scary up there!

Here’s a few outtakes:





This is the second of a four-part series about shooting an ad campaign for a Real Estate broker. Also in the series:
A Clear and Present Kitchen

3 responses to “Up On the Roof

  1. WOW! I really enjoyed reading this. Really makes me think outside the box when agents ask for if I do headshots!!

  2. This is 100% pure awesomeness!

  3. Awesome! I’d love such a cool client myself too! Love the whole thing!

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