Kevin O’Leary is best known as the hard-nosed, unsentimental investor on Shark Tank — not for making movies, and certainly not for being warm. Which is why spending a full day photographing him at Miami’s Little River Studios was such a surprise. He was sharp, grounded, and genuinely fun to collaborate with — not exactly what you expect from someone with his reputation, résumé, or net worth, or from a first-time feature film actor.

When I asked Kevin why he decided to move into film, his answer was simple: it was always something he had wanted to do — but no one had ever asked before. That changed when Marty Supreme director Josh Safdie called him directly and said he needed a real a-hole for a role in the film. Someone sharp-edged. Someone real. Kevin tells the story with a laugh, clearly amused by the irony of being cast for the very qualities that made him famous. Off camera, he was candid, engaged, and collaborative — never once resembling the caricature people expect to meet.

I’d heard he was into guitars, which is also a passion of mine, and we quickly bonded over vintage instruments. He has an impressive collection and is a major investor in Fender. He brought his own wardrobe and did his own makeup — surprising and notable for someone who could easily arrive with an entourage, but instead chooses to be self-reliant and knows exactly what works for him. His collection of vintage Prada, Dolce & Gabbana, and Tom Ford jackets was a gift to pull from, along with his accessories — vintage watches being another deep passion and one he’s invested in significantly, even owning a watch insurance company. Together we assembled each outfit and accessory we would use in the shoot.

My assistants, Flip and Jacques, kept commenting on his look and overall vibe throughout the day. At one point I told Kevin he was giving off a “modern vampire” energy, which he got a huge kick out of. He leaned in, saying he didnt want to ruin it for me but told me a now-public spoiler from Marty Supreme, where his character reveals he’s a vampire from the 15th or 16th century. He clearly enjoys playing into the myth — because that’s what people think he is — while in reality he’s smart, a gentleman, yet someone who is not afraid or hesitant to tell it to you straight if he thinks you are in need of his proven sage advice.

O’Leary never plays pong in the film, but the ping-pong paddle itself plays a memorable role. In what has become one of the most talked-about scenes in cinema this year, he delivers a sharp, unexpected moment opposite Timothée Chalamet using a paddle — a scene that instantly entered pop-culture conversation. That moment was exactly why we wanted to incorporate the paddle subtly into our shoot. Along with a giant shark mounted on the wall and a small shark statuette, it added context without hopefully being to on the nose. Kevin needed no direction or prodding — once placed in a scene, he simply became the performer and thespian he is. My only role now was to frame it and light it and make it look cool. I initially leaned toward subtlety, but when personality fully shows up, sometimes you let it take over. In this case, that’s where the magic happened, and we captured a bit of everything.

I’ve since seen the film and was genuinely impressed by Kevin’s performance. He toned down elements of his Shark Tank persona while amplifying others, resulting in a confident, memorable debut in a film already sweeping major awards. At the Golden Globes, Timothée Chalamet even thanked “Mr. Wonderful” during his Best Actor acceptance speech — something few people would have predicted. But it made sense. Kevin gave generously in front of my camera, was a true collaborator throughout the shoot, and I imagine that same energy carries through every set he steps onto.

Case StudyKevin O’Leary — Celebrity Portrait Session

Role: Photographer & Director

Client: Toronto Life

Subject: Kevin O’Leary (Shark Tank, Marty Supreme)

Location: Little River Studios, Miami

Project Objective

The objective was to create a contemporary portrait series that could support both editorial and promotional use while aligning with Kevin O’Leary’s evolving public profile — from long-established television personality to feature film actor.

For celebrity and commercial portrait clients, the priorities are clear: efficiency, control, and images that feel intentional and versatile across platforms. This shoot was designed with those realities in mind.

Creative Strategy

Rather than attempting a dramatic reinvention, the approach focused on controlled evolution — acknowledging O’Leary’s recognizable persona while presenting him in a refined, cinematic context.

The visual strategy emphasized:

• Clean, graphic portraits suitable for press and promotion

• Subtle conceptual elements tied to the film without overt branding

• A range of moods that allowed flexibility for layout, crop, and usage

Restraint was key. The images needed to feel confident and current without overstatement.

Process & Execution

We built three distinct studio setups that could be executed efficiently while producing clearly differentiated results:

• A primary portrait setup focused on authority and presence

• A conceptual setup incorporating props connected to the film narrative

• A darker, cinematic setup using background flats and controlled lighting

Once the shoot began, direction remained minimal and responsive. O’Leary is highly comfortable on camera, so the focus shifted toward creating space for natural movement and expression rather than over-directing. This approach kept the pace relaxed, protected the schedule, and allowed strong moments to emerge organically.

Wardrobe & Styling

Wardrobe was integrated into the visual strategy from the outset. O’Leary arrived with a curated selection of vintage Dolce & Gabbana, Tom Ford, and Prada jackets, along with distinctive accessories including bolo ties, skull cufflinks, and vintage watches worn on both wrists.

Each look was selected intentionally to support the tone of each setup and maximize the versatility of the final image set.

Location Expansion

As timing allowed, we transitioned outdoors during magic hour. Little River Studios’ backlot — with its old-Hollywood textures and architectural elements — provided a cinematic extension of the studio work and added scale and movement to the final portraits without adding complexity to the production.

Results

The final deliverables provided a cohesive, flexible portrait set suitable for editorial, press, and promotional use. The shoot remained efficient, collaborative, and tightly controlled, producing a body of work that reflected both the subject and the goals of the project.

Credits

• Photography & Direction: Chris McEniry

• Art Direction: Colleen Nicholson (Toronto Life)

• Production: Kim McEniry

• Lighting & Grip: Felipe Patiño, Jacques Bruna

• Local Production Support: Felipe Patiño