Jack Ottaway spends as much time as possible walking the neighborhoods of San Francisco interacting with and photographing the people who live there. In part two of our interview, Jack shares the inspiration behind his work and provides insight into his powerful series featuring the homeless of San Francisco.
Q: Is there a photographer or type of photography that influenced your work or inspired you?
A: My late father really fueled my initial interest in photography. Also, Alfred Eisenstaedt, a Leica Man, was another photographer who inspired my work with people. For a number of years I vacationed on Martha’s Vineyard in late August, as did he. Each year on Labor Day Weekend, Eisenstaedt would give a slide presentation and detailed talk about his work at a local church on the island. I was lucky to attend this presentation twice to hear him describe his extensive body of work for LIFE magazine. Every time I go into San Francisco to continue my work, I hope that I’ll make a photograph as good as his famous photograph, “V-J Day in Times Square” taken in 1945, when I was six months old!
I have a fairly complete library of books by great photographers that I study to improve my ability to see – Cartier-Bresson, Atget, Magnum, Friedlander, and especially Garry Winogrand are names that come to mind. I also take a lot of inspiration from contemporary photojournalists, like Jan Grarup, who do amazing work under harrowing conditions in places like Afghanistan and Somalia. I just recently discovered the amazing work of the unheralded U.S. Army photographer Charlie Haughey, whose photographs of the Vietnam War really resonate for me because I too am a Vietnam Veteran.
Finally, I get inspiration every day from my network of Leica user friends here in the Bay Area, and  around the world via social media. I am amazed at the high quality photography that is being done by so many people whose work will most likely go unpublished and unnoticed. Being a member of the ‘Leica Family’ has been another key factor in expanding my network of quality photographers.
Q: Your father died at a young age and was therefore not able to guide you personally. How do you think seeing and appreciating your father’s images has influenced your work and do you feel that in some sense you are fulfilling your father’s mission?
A: Having my father’s old negatives and prints, all of which were in black-and-white, gave me a fundamental appreciation for seeing in black-and-white and for making photographs that are more than snapshots. His work was creative and technically well executed. I certainly do feel that I am completing his ambition to be a skilled and successful photographer. That said, I do photography because I love it. It is my only creative talent.

Q: As mentioned in part one of our interview, you said you retired from business and now do photography as your day job. Did you have any formal education in photography or were you self-taught?
A: I haven’t had any formal education in photography, but I have read extensively, and studied thoroughly, a long list of books on photography, especially those that include the work of the masters of the art form. I have also made it a point to associate myself with other good photographers and to learn from and with them. I have always sought out critical feedback on my work from the best photographers I could find. The Leica Akademie workshops are part of my continuing education.
Q: What have you gained by participating in the Leica Akademie Workshops?
A: I attended every relevant Leica Akademie workshop offered in the San Francisco area in 2012 and gained a wealth of knowledge and experience from my interactions with the instructors and other attendees. These classes offer a great combination of technical information, practical in-the-street shooting opportunities and good critiques and feedback about your work. The instructors are top-notch. Having a professional photographer as part of the staff is very valuable to the student. Perhaps the most valuable thing I’ve gotten out of these sessions is the ongoing working relationships that I have established with the instructors and the other participants. Leica owners and Leica company folks really are a family. I am very happy to be a member of that family and I would heartily recommend the Leica Akademie Workshops to anyone.
Q: Your powerful and sensitive portraits of homeless people in San Francisco certainly seem to capture the individual personalities and the implicit hardship in the lives of these people. How did you approach these folks and gain their trust? Did you have social purpose in documenting them or was it just art for art’s sake and revealing aspects of the human condition?
A: I approach each of these people as I would anyone I might meet on the street, with respect and dignity. I typically approach them and discreetly offer them a few dollars, which they need, and which always makes them more willing subjects. I explain that I am doing a project on the plight of the homeless in San Francisco and ask if they would let me make a few photographs of them. I talk to them, as much as they are able, in order to keep them engaged and to better get their individual stories. Unfortunately, many of these people are so physically and mentally debilitated that they are unable to speak clearly or carry on a real conversation. Regardless, I speak to them as I would anyone and treat them respectfully. Many seem very happy to have someone actually take the time talk to them, if only for a few minutes. So, for the time being, I am recording and revealing specific aspects of the human condition in the homeless community. If I ever publish this work I hope that by doing so it will bring more attention to this problem and more resources to help mitigate the situation.

Q: How did your “Homeless” project come about?
A: The Homeless project evolved out of my numerous forays into San Francisco to do street photography. As I encountered more and more of the homeless in my walks around the city, I noticed that most all the photographs being made of them by other photographers were just sniped shots made from long range, without regard to the feelings of the person being photographed.
For a long time I avoided making photographs of the homeless, not wanting to seem as if I was taking advantage of their already bad situation, or in some way embarrassing them. However, I came across a homeless man one day that I knew I needed to photograph. The photo I made that day is “The Look.” That person was among the most frightful looking people I have ever encountered on the street. The scene that I captured in that photograph, of a desperate man swaddled in a pile of blankets, kneeling on the sidewalk surrounded by his meager belongings, was the eye-opener for me with regard to how really awful the human condition can be in an otherwise prosperous city. After making that photograph I knew that I needed to do a series of the homeless that would tell their desperate story in a thoughtful, respectful way. In the case of the homeless, I am an empathetic observer for each individual photograph I make and a storyteller when the series is viewed together.

Q: “Vince” is an incisive and brilliant portrait. He seems refined and resigned yet there is something about him that seems, if not quite hopeful, yet seeking something better. Am I reading too much into it, and what does it mean for you?
A: I’m happy that you like Vince. He is one of my favorite portraits of a homeless person. You are right-on in your assessment of Vince. He was very talkative and animated. He told me that he “was looking for work in pictures.” I told him that he just might find work as a stunt double for Willem Dafoe, the actor from the film “Platoon.” He liked that. He was hopeful, which most homeless people are not. I’m happy that my photograph communicated that to you. I could have done an entire study on Vince but I have never seen him again. Maybe he got his big break.

Q: This image of “Pop” is simply amazing. Who is this person, where did you find him, and do you know his story?
A: I found Pop along Mission Street in San Francisco on Easter morning. He and Vince were together, in the rain, both in wheelchairs. I approached them, held out two dollars between them and asked if I could make a few photographs. Vince took the two dollars from me, gave one to Pop, and kept the other one. I made a couple of shots of Pop and asked him his name. He answered, but I could not understand him. Vince told me, “That’s Pop.” As you can see from the photo, Pop has very bad problems with his eyes. I doubt that he can see much at all. I have been back to the Mission many times since I made this photograph and Pop is always in the area around the 16th & Mission BART (train) station, an area recently reported on in local news as one of the most dangerous locations in the City.

Q: This image entitled “Sisters” is riveting, and it reminds me of a Diane Arbus because of the twins subject and its surreal and disturbing qualities. How do you feel about this picture and what do you think it communicates to the viewer?
A: Thank you for the comparison to Diane Arbus, a high compliment. It also reminds me of the twins work by Mary Ellen Mark who, coincidentally, I met in person at the opening of the Leica Gallery and Store Los Angeles recently.
It was a surreal scene when I first noticed these two women along Market Street. First, you do not encounter many homeless women, let alone sisters. When I approached them to ask to make a few photographs, the sister on the right indicated “No!” in a fairly strong way, while the one on the left seemed interested. So I offered them $5.00. The one sister convinced the other to pose and I made this photograph. As I started to make a second photo, the sister on the right turned away from me and would not look back. I could not really talk with them because they only spoke in Russian, or a similar language that I did not recognize. What I see here are two women who, in spite of their obvious dire straits, have been able to maintain a certain dignity, which is reflected in their warm smiles and demeanor. This is a quality I have found in other homeless people who have not given up on improving their lot. I suspect this photograph may communicate the contradictions in the life of homeless people, where, as in this case, they can be beautiful on the one hand and a picture of destitution on the other. I consider this one of my best efforts at street portraiture.
Q: Which lenses do you favor for street photography and which ones did you find yourself using most often on these projects?
A: I use the 35 mm and 50 mm Summilux ASPH. lenses exclusively for street work. I prefer the 50 mm for close-in portraits and the 35 mm for those photographs where I want to include more environment. In a pinch, either lens can do both jobs.
Q: How do you see your photography evolving over, say, the next three years and do you have any new projects in the works that you can talk about?
A: I spend a lot of time learning from others, but I doubt that I will change genres. Eventually, being published in LFI and LensWork is a goal. I have also started thinking about doing a project profiling long-term survivors of the HIV/AIDs epidemic in the Bay Area. I also have a growing body of work related to the numerous street fairs and similar events in San Francisco that I may boil down and try to get published.
Thank you for your time, Jack!
– Leica Internet Team
To see more of Jack’s work, visit his website and Flickr.