Offices on two continents, 120 represented artists, a residency-and-rental property, an art gallery, a thriving wholesale puzzle business, frequent events, and a podcast.

These are just a few of the ventures that The Jacky Winter Group, a creative production and artist representation studio, tackles with its team of about a dozen employees.

How—and why—do they do it all? In an interview with Adobe Create earlier this month, agency founder Jeremy Wortsman shared his story about starting, growing, and evolving Jacky Winter into an adaptable and agile international powerhouse in the field of illustration.

Jacky Winter is headquartered in Melbourne, Australia (Wortsman’s home), with a satellite office in New York (his hometown). After an upbringing steeped in art and visual culture, Wortsman decamped for Australia in late 2001; there, he continued his career as an art director and eventually cofounded Is Not Magazine. It was while pursuing this venture that he discovered that the types of artists he wanted to work with weren’t visible in the commercial illustration scene. Wortsman created Jacky Winter in 2007 to fill the stylistic gap in the existing market.

Jacky Winter’s artist roster has been shaped by Wortsman’s curatorial eye, honed over a lifetime of conscious and subconscious influences: a youthful passion for ice hockey, illustrated logos, and industrial music; internships that touched on illustration; and a family peppered with comic artists. “There’s all this stuff that’s in my DNA,” says Wortsman. “And that kind of filtered down to a singular vision.”

Currently, the company’s roster of illustrators spans from traditional artists and muralists to GIF artists, filmmakers, and storyboard artists in a range of techniques and aesthetics. From among two dozen categories on the Jacky Winter site, clients can choose “weird and abstract,” “flora and fauna,” “on-site and live illustration,” or “editorial and conceptual.”

There’s all this stuff that’s in my DNA,” says Wortsman. “And that kind of filtered down to a singular vision.

The agency has steadily grown over the past thirteen years, gaining traction with its unique point of view. Reinvesting in the business to fund experimentation and passion projects is a core element of Jacky Winter’s ethos. “It’s a way to always get two things done, in a way. With the fun things and the community things we do at Jacky Winter, I’m always trying to figure out how I can do the things I want to do, and then how to subsidize it with something else.”

Wortsman points to Lamington Drive as an example of his strategic diversification. The gallery, which was established in 2010, isn’t very profitable, but it brings joy to the Jacky Winter team and is financially offset by the agency’s commissioned work. “As a social hub for people to gather and for us to interface with our community directly, it does have flow-off effects with what our reputation is and who we are and our identity,” says Wortsman. “Everything we do has those dual components. Eventually we were able to buy property and do Jacky Winter Gardens [a residency studio and rental property], we were able to expand into New York, we were able to get into tech development, we were able to get into VR—just a million different things.”

Since Jacky Winter’s start in the mid-aughts, two profound digital changes have dramatically shifted the landscape for agencies that represent commercial artists, according to Wortsman. Online courses and access to self-teaching tools have dramatically expanded the number of working artists, and social media has increased access to those artists. In the recent past, most clients had to work with agencies to gain access to editorial illustrators, photographers, and animators; now they can discover artists themselves and book them directly. And with increased competition, more artists are diversifying their income streams instead of relying on an agency to facilitate and mediate their entire career.

“It’s important that we help our artists and augment the skills that they have and let them do what they’re best at—the artwork—while we do what we’re best at.
Jeremy Worstman

Jacky Winter has maintained its vitality by consistently being a true partner with their artists, and by introducing new ways of working that respond to the evolving market. “It’s important that we help our artists and augment the skills that they have and let them do what they’re best at—the artwork—while we do what we’re best at: maximizing their fees by educating the industry, educating our clients, and developing tools and processes that are unique to us,” says Wortsman.

Their team of producers also provides in-depth support for clients. As the financial resources for creative agencies have dwindled, art departments have become more strapped and less specialized. “The demands for creativity and performing and doing great work are so high for everyone right now, so we’re acting as a partner for agencies as well. When partners are coming to us, we’re not just reps but also hands-on producers and art buyers and all these other things. We’re really multidisciplinary in this way,” Wortsman explains.

In the past year, Jacky Winter has introduced Corvid, a tool that gives artists as-needed access to Jacky Winter expertise without requiring a formal, on-going representation commitment, and the agency has shifted to a seasonal model that reflects longstanding ways of working in both fashion and professional sports: along with a core line of artists that Jacky Winter works with year after year, they introduce new artists that sign on for the season, every six months.

That’s a catch-22 of any growing business: the bigger you are, the less risk that you can take, but the paradox is that you need to take big risks to have big success. So we’re always trying to figure out where that line is. The seasonal model meets the needs of clients who are looking for work that is in line with of-the-moment aesthetic trends, and offers more flexibility and opportunity for artists, who are encouraged to refresh their portfolios and update their long-form interviews on the Jacky Winter website.

“Previously with representation, when you bring someone on, you’re making this pact. It’s like going right into a long-term relationship with somebody,” says Wortsman. By introducing Corvid and the seasonal model, “we’re trying to loosen that up a bit more and be a bit more agile in trying to find people.” As Jacky Winter continues to evolve, its founder continually tests the balance of risk and reward. “That’s a catch-22 of any growing business: the bigger you are, the less risk that you can take, but the paradox is that you need to take big risks to have big success. So we’re always trying to figure out where that line is.”

Heading into 2020, Wortsman sees great potential in the ethical quandaries and social struggles that are motivating so many creative minds. “There’s a huge growth in wanting to tackle the big issues that are going on in the world right now, and the artistic community is really stepping up in terms of problem-solving here with bigger thinkers in tech,” he observes. “I think design is what made a lot of this technology really bad, and I think design and art will hopefully get us out of it in some way as well.”

The Jacky Winter team is excited to be a part of that momentum. “We want to make sure we’re actually helping people. For me, it’s on a much deeper spiritual and religious level, where I want to be of service to fellow people. That gives me a lot of motivation,” says Wortsman. “We’re doing some really big things this year, and if you talk to me a year from now, we’ll be having a very different conversation.”

The Jacky Winter Group’s website to learn more and see more of their work.

Interview originally published on Adobe Create. Words: Laura Staugaitis.