How an illustrator-run agency survived three decades by doing things differently

Heart’s 30th-anniversary book reveals what happens when working artists, not traditional businesspeople, take control of their representation.

When Darrel Rees founded Heart back in the 90s, he did something unusual: he remained a practising illustrator while running an artist agency. Three decades on, that decision still defines how Heart—which made our list of the best illustration agents in the UK—operates. It might also explain why it has outlasted so many contemporaries.

To mark its three decades, Heart has published What Happened, a 134-page hardback in which 34 represented artists illustrate significant events from each year of its existence.

Some chose historical moments (elections, cultural shifts, technological breakthroughs). Others depicted personal experiences that shaped their practice. Together, the images form a subjective timeline that reveals as much about the artists as about the past three decades.

But the book also tells another story, one that matters to anyone navigating the precarious business of creative representation. Interspersed with the artwork are photographs from agency parties, studio gatherings, and exhibitions; evidence of a culture that Heart has deliberately cultivated since its inception.

This isn’t simply nostalgia. It’s a documentation of a business model built on friendship, mutual respect, and the belief that artists should have control over how they’re presented to clients.

The Big Orange legacy

Heart emerged from Big Orange, a studio collective where Rees worked alongside nine other illustrators in the early 1990s. Big Orange threw warehouse parties, mounted exhibitions and maintained what the agency describes as “a generally irreverent attitude to the practice of illustration”. When Rees launched Heart, he brought seven of the 10 Big Orange members with him.

The motivation was straightforward: create an agency where artists could present themselves to clients on their own terms. At a time when many illustration agencies operated as traditional gatekeepers, this was a deliberate departure. Heart wanted to represent artists fairly and liaise with clients in an “even-handed manner”, treating both parties like adults capable of honest conversations.

Three decades on, that principle still holds. The agency is run by four people who all come from illustration or graphic design backgrounds: Rees, Amanda Mason (who manages the New York office), Jenny Bull (who runs the London operation), and Helen Osborne (who oversees both). They’re not career agents who learned the business by selling other people’s work. They’re creative practitioners who understand the work because they’ve done it themselves.

A different kind of timeline

What’s striking about What Happened is what it doesn’t do. This isn’t a corporate book designed to court clients. There’s no mission statement, no brand narrative. Instead, there’s work: 34 distinct artistic responses to the question of what mattered over the past three decades.

Some artists illustrated the fall of the Berlin Wall, the advent of the internet, and climate protests. Others chose the birth of a child, a move to a new city, or a personal loss. The book doesn’t try to reconcile these different scales of significance. It simply presents them side by side, suggesting that historical events and personal experiences carry equal weight in shaping creative practice.

Each year is accompanied by three historical facts, a device the agency uses to “accentuate the positive” rather than catalogue every tragedy of the past thirty years. It’s a choice that reveals Heart’s house style: optimistic without being naive, engaged without being heavy-handed.

Why this matters

In an industry where agencies fold regularly and representation can feel transactional, Heart’s three-decade run is worth examining. Some artists have been with them since 1994. Others joined recently. The retention rate suggests something is working.

Part of it is structural. An agency run by practising creatives understands the rhythms of creative work in ways traditional agencies often don’t. They know how to balance commissioned work with personal projects, why certain jobs aren’t worth taking even when the money is good, and that artistic development doesn’t follow a linear path.

But structure alone doesn’t explain longevity. Heart has clearly invested in relationships, not as a branding exercise, but as the foundation of how they operate. The agency describes the bond between its artists as one of “friendship and respect.” In an industry where competition often trumps collaboration, this is a radical proposition.

Level of trust

What Happened makes that proposition visible. It’s a book that could only emerge from an agency where artists trust each other enough to contribute work to a collective project without knowing exactly how it will be used. That level of trust takes decades to build. You can’t fake it with good marketing.

For creative professionals navigating their own careers, Heart’s anniversary offers a reminder: the most sustainable creative businesses aren’t built on aggressive growth or slick positioning. They’re built on mutual respect, honest dealing, and the belief that good work speaks for itself. Thirty years suggests they might be onto something.