Paolo Ciccone: A Journey to Reviving 1930s Hollywood Glamour in Modern Photography

Success story summary Building an art-focused business comes with unique challenges, as Paolo discovered in his journey as a portrait photographer specializing in 1930s Hollywood glamour. Overcoming language barriers and introversion, he focused on personal branding and transformative experiences for his clients, which set him apart. His dedication and unique style have led to a successful business that brings timeless elegance to modern photography.

Can you please share a brief history about your photography business? What motivated you to start this venture?

I learned photography from my father in the late 1970s. We developed black-and-white film in our improvised darkroom, just like so many others.

I always loved the visual arts and went to the Art Institute in Trieste, Italy, but I did not pursue that field professionally until a few decades later, in the early 2000s. It was a time of change, and I felt the call of photography and cinematography. It started as an “I wonder if…” situation, and then the idea struck me as wonderful and exciting. So, I spent about three years working in Los Angeles in the industry, met many great people, and learned a ton about making movies.

That experience gave me the foundation for using cinematic lighting and employing many techniques that are less common in the traditional field of photography. From using continuous lighting to manual focusing, cinematography taught me how to approach a session beyond the boundaries often placed by traditional photography.

Working with actors has been a tremendous experience, helping me form my comfort with portrait photography. I’ve always loved portrait photography, so I decided to pursue that path. It’s been one of the most rewarding experiences of my life.

A portrait image by Paolo Ciccone

What kind of challenges did you face when building up your portfolio or setting up your studio? How did you overcome these challenges?

When it comes to building a business around art, the challenges are enormous. With a standard business, like a plumber, lawyer, or realtor, you have a very specific problem to solve, and you can advertise your services based on the great ways you solve that problem.

With photography, even just confining it to portrait photography, you have a wide array of options. I knew that I didn’t want to do weddings or newborn portraits, for example. I like working with business people to help them with their personal brand, and I like to give a great transformation experience to women who are looking to reaffirm themselves or who want to see how beautiful and elegant they are in their 40s, 50s, 60s, and beyond.

Finding the right direction and understanding how people see these kinds of portraits was a long and arduous journey. It still is! 🙂

On top of that, I tend to be a rather shy person, and English is my second language. I always feel that the moment I open my mouth and people hear my Italian accent, it makes me sound ‘funny.’ There’s a lot to overcome there.

Learning how to build your portfolio as an introverted person is a struggle by itself. Discovering what you want to create is another challenge as well. I wanted to have an identifiable style, but I didn’t know what that style would be for years!

It’s the nature of this business that you can be incredibly busy, and a week later have no one to photograph. In those slower times, I like to invite models and other people to do personal projects, enrich the portfolio, and keep experimenting with lighting and film.

Could you describe the early days of your business? What were the initial reactions and feedback you received?

Most new businesses have slow starts, and mine has been very gradual. This is not my first company, but the photography business is definitely different from most others, and it took a long time to figure out the basics. You would think that having great photography is the foundation of a healthy business, but that’s not true. You can be the most talented photographer out there and still not make any money. You really need to be very proactive in your marketing and have a very clear idea of who your clients are.

I went into portraiture because I like working with people, and I love seeing how I can make people shine in front of the camera. My clients feel that enthusiasm, and they have told me repeatedly that their time at the studio was fun and even exciting. One client called me “the motivational photographer.” That is one of my biggest successes.

When they see their portraits, the reactions range from gasps of delight to tears of joy. Making a difference in their lives is what gives me the greatest joy.

A portrait image by Paolo Ciccone

How did you manage to grow and expand your business? What strategies did you use to attract more clients?

Defining my clientele was the single most important step I took to steer my business in the right direction.

When starting a new business, we want to have as many clients as possible, so the logical response is to have a broad appeal. The surprising reality is that it works exactly the opposite way. If you advertise to everybody, you advertise to nobody. That’s because, at any given moment, people are sensitive to certain messages, and if your message is broad and general, it has no appeal.

You need to define who your best audience is, understand their motivations, and then tailor a message that makes them stop and take notice. Once you have mastered that, you can move on to another segment of the public.

Inevitably, there are many aspects of running a business like this that are unknown. Coaching is a crucial part of fast-tracking your success. I learned things from coaching that made perfect sense but also left me completely baffled. I have spent thousands of dollars on coaching over the years, and I still do, and it has been invaluable. I would have probably given up without coaching because figuring out some of the human-based factors is simply mind-boggling.

The technical stuff is easy—buy a piece of gear, read the manual or watch a couple of YouTube videos, and you get it. The human part is hard. Why people hire a photographer and how they get motivated is very, very different from what I thought. So, if you want to fast-track your business, stop buying gear. You can get by with a very modest camera, a couple of lenses, and a tripod (this one is very important). Instead, find a good coach and dedicate time to learning what they say.

A portrait image by Paulo Ciccone

How has your business performed financially over the years? Can you share some milestones or achievements in terms of revenue?

Selling wall art or prints, in general, is a key factor in bringing in the type of revenue that you deserve as a portrait artist. When I started, I had no idea what IPS (In-Person Selling) was because I could not fathom trying to sell remotely. For me, selling has always been done in person. Why would you detach yourself from your client after you have done something as personal as creating their portrait? I actually enjoy the process; I love seeing how people react and how they look at their portraits.

It’s my job to guide my clients. I could never abandon them with an online gallery. That experience is dreadful. There isn’t anything positive about online galleries, and they are overwhelming for the client. Many times my clients have expressed their gratitude to me for sparing them the nightmare of having to decide by themselves.

I don’t think that we, as a society, have fully realized that the combination of online galleries and digital photography—what I call algoimagery—has created this monster, this false “benefit” of shooting thousands of nearly identical photos and then dumping the whole thing on the lap of the client. How is that a great experience? Give them a smaller set of absolutely stunning images and do your best to amaze them!

So, selling tangible goods is key to running a profitable business in photography. There are alternatives, but you have to be very careful about them. I make good sales with professional headshots, which are, by definition, in digital format. An absolutely key factor in that is that I work with the client in person immediately after the session, and I help them make the selection. The session is custom-tailored to each client so that they get the type of portraits that are aligned with their brand.

In any case, we are talking about a limited set of images sold at a profitable price point and that are of great value to the client. I am not aware of any other field of portrait photography where the ratio of time versus money is so favorable.

What are some key lessons you've learned along your entrepreneurial journey? Is there anything you would do differently if given a chance?

I would start immediately building my portfolio with a series of free sessions. I would not hesitate to create a recognizable style that separates me from others, and I would focus all my initial energy on marketing.

The truth is, many of us start in photography because we love making photos. But when it comes to turning that fun into a profitable activity, we are not so sure about what’s best, so many people look at the established artists. People like Joel Grimes or Sue Bryce are great, but the world doesn’t need 1,000 more Joel Grimes or 10,000 Sue Bryce clones.

A lot of people don’t feel very confident about making a statement with a unique style because it’s risky. What if people don’t like it?

When I decided that I needed to have a unique style, I looked at what fascinated me, what got me excited. Since I can remember, I have loved the Hollywood portrait style, but I had no idea who the key players were or how that style really worked.

I knew that I was looking at a physical impossibility, as those portraits feature absolutely flawless, alabaster-like skin, while simultaneously being made with sharp lights, a detail evident by the razor-sharp edges of the shadows. People often argue that that was obtained with cakey makeup, but that is absolutely false.

It took me about two years of research to understand the exact mechanics of that style, from the lighting to the makeup (or lack thereof), to the retouching, and the film photography. I read books and scoured the internet for documentaries and interviews that could shed some light.

The film stocks of the 1930s and 1940s are gone, and the developer used by George Hurrell and others is not known today, so we cannot draw parallels to the products of today.

But through trial and error and hours in the darkroom, I have come to a faithful recreation of the Hollywood portrait while making it connected with modern tastes. Regaining familiarity with film has been a very exciting part of that journey.

The whole point is, it took a long time and it was a gamble, but today I’m part of a very restricted group of photographers in the world who create authentic black-and-white portraits in the style of 1930s Hollywood, down to shooting in medium and large format film. People are noticing it, and if you want to have a real Hollywood portrait, recognizable by that undefinable quality of light and glow, there aren’t many choices in the market, and that gives me a position of advantage.

When you are a brand of one, you decide how to sell it. It’s not a guarantee, but it helps in standing out from the competition.

Are there any tools or software that have been particularly useful in managing and growing your business? Give us a list of what you use in your kit.

The Hollywood portrait relies on extensive editing. What many people don’t know is that in the 1930s, 1940s, and beyond, portraits were edited extensively. It was part of the look. Hard lights were used, which made skin texture more pronounced, and then the negative was edited to make the skin flawless. Of course, this is a gross simplification.

The point is that I use similar techniques but in a more modern workflow. I scan the negatives using a flatbed Epson scanner together with SilverFast and VueScan.

The images are then tagged and selected using Adobe Bridge. I used Lightroom for a period, but it is a pain to deal with catalogs and having to synchronize all file changes via LR. It’s just not my modus operandi, and so Bridge works just fine. It does most of what LR does without the hindrance of the catalog.

Every portrait is then edited in Photoshop. Basically, there isn’t a single pixel that is left alone. In one way or another, every part of the image is repainted by hand. I use a Wacom tablet to help with that.

For business management, I use a CRM that allows me to keep track of all the requirements of my clients, plus notifying them of the appointments and so on. A good CRM is absolutely necessary to run this business.

A portrait image by Paolo Ciccone

Could you recommend any books, resources, or mentors that have significantly influenced your business journey?

Yes, I would suggest that every photographer learn to use film, even if it’s just on the side as a hobby. There’s a discipline in learning to shoot a proper frame on film that will benefit digital photographers as well. Learning to accurately expose a frame without guesswork and without relying on the reflective light meter built inside a camera is a skill that will pay off for your entire life.

On the business side of things, I suggest reading ‘The War of Art’ for incredible insight into the artist’s mind, ‘You Are a Badass at Making Money’ for fantastic help in shaping your business mindset, and, of course, ‘Building a StoryBrand’ to help you understand how to speak to the client instead of glorifying what you do as a photographer.

At the cost of sounding like a broken record (that’s an analogy that went away and has come back), nobody will hire you solely for your great photography. Instead, it is our ability to understand how we can use photography to help people that will make the biggest difference.

What advice would you give to budding entrepreneurs who wish to start their own photography business?

Don’t listen to the ‘if you build it, they will come’ nonsense. You need to find every client by directly putting yourself out into the world and talking to people. Portfolios don’t bring clients. Websites don’t bring clients. Going out there, being in front of people, shaking hands, and creating strategic alliances with other businesses will bring clients.

And for the love of everything sacred, don’t try to sell via email. The only way to make a sale is face-to-face with a client.

Above everything, marketing is the most important thing that a photographer can do for their business. Make sure that you spend time marketing your business every day. Yes, every day.

A portrait image by Paolo Ciccone

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Paolo is a passionate portrait photographer specializing in 1930s Hollywood glamour. Paolo’s unique style, focusing on personal branding for business professionals and empowering women, is what sets him apart. His clients appreciate his ability to make them shine, often calling their sessions fun and transformative. Through dedication and creativity, Paolo has carved a niche that brings timeless elegance to modern photography.

About Paolo

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There is a richness to using film that cannot be found anywhere else. Film is much simpler to access than many people think, and it will open up a whole new set of possibilities.

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📸 Interested in headshot photography? Check out this podcast episode with Joe Jenkins!


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