How I Built the Agency of My Dreams

Going Full-Time and the First Hard Lessons (2009 Onwards)

In 2009, with a master's degree behind him and no desire to spend more time in formal education, Jimmy went full-time as a freelancer and agency founder. His first act was building a solid technical boilerplate so that he could deliver projects efficiently and bill at a rate that made the business viable.

The timing was not ideal. 2008 and 2009 were recession years, and getting started in a contracting market required sustained effort. He describes working 12-hour days as simply the cost of entry. Eventually he made his first hire.

Almost immediately, managing people introduced new complexity. Jimmy learned early that time logging is non-negotiable when charging by the hour. His first employees did not share his dedication: one staff member took three hours of cigarette breaks per day. Making that person confront his logged time turned out to be a useful management moment, but it was also an early signal that people's relationship with work would vary enormously from his own.

Pioneering Care Packages and the Case for Recurring Revenue

One of Jimmy's most significant early innovations was the introduction of care packages and maintenance retainers. He claims to have been a pioneer of this model in Scandinavia, and notes that after he established it, many others in the region copied the approach.

The reasoning was simple and painful. Without recurring revenue, the business was at the mercy of project flow. When projects came in, money came in; when they dried up, so did cash. Jimmy came close to bankruptcy at one point as a direct result of insufficient recurring revenue. That near-miss crystallised what he considers the most important lesson of his career: recurring revenue is the difference between running an agency and remaining a freelancer indefinitely. He returned to this point several times throughout the talk, framing it as the number one takeaway for anyone in the audience.

Building a Team and the Four-Person Wall

As the business grew from solo to a small team, Jimmy identified what he calls a "stopgap"

that emerges at around four people. Below that number, a founder can hold everything in their head. Above it, that approach breaks down completely.

He describes waking up in the middle of the night, suddenly remembering something that had been missed. Staff would forget tasks. Things would fall through the gaps. His conclusion was that project management tooling — writing things down, tracking work formally — is not optional past roughly four people. It is the precondition for any further growth.

This moment of recognition led to a broader insight about role definition. Not everyone is suited to every type of work. Some people are energised by project delivery. Others are happiest with the rhythm of maintenance, updates, and bug fixes. Others still are temperamentally suited to support. Matching people to roles that fit their nature, even in a small team, made a meaningful difference to output and morale.

Standardisation and Niching on WooCommerce (2016)

By 2016, roughly ten years into the agency's life, Angry Creative was reaching a point where things were, in Jimmy's words, "starting to fall apart." The fix was standardisation on multiple fronts simultaneously.

The agency standardised its hosting environments and deployment workflows. It also made a decisive choice to niche on e-commerce, and specifically on WooCommerce. Jimmy is candid that the e-commerce landscape of 2016 looked very different from today — Shopify was not yet the force it would become — but the principle behind the decision remains sound: specialisation creates credibility, enables reusable assets, and allows a team to build genuine depth.

He used an analogy: when you hire a tradesperson to build a wardrobe or install a pool, you want someone who has done it before. You want someone with prefabricated components, prior experience of the problems, and tricks developed over time. That is what a niche agency can offer. Boilerplates give the agency those prefabricated components.

Jimmy noted that each major change to the business — including this one — resulted in some clients and some staff leaving. He was honest that this was emotionally difficult, particularly early in his career when he wanted everyone to like him. With experience, he came to see it differently: change produces churn, churn is the price of progress, and the people and clients who stay are those who actually fit the direction you are going in.

You want someone with prefabricated components, prior experience of the problems, and tricks developed over time.

Bringing Design In-House and Reviewing Partnerships (2018)

Up to around 2018, Angry Creative had worked with a range of external designers and freelancers rather than maintaining an in-house design capability. Jimmy made the decision to bring design in-house, driven by the reality that external partners always optimise for their own interests. Partnerships that looked mutually beneficial on paper had limits that only became visible over time.

He acknowledged being on the receiving end of this dynamic too — other businesses had taken his services in-house and left him without a client. It is never comfortable to be on that side of the equation, but he framed it as simply part of how businesses evolve. The question to ask periodically is whether a given partnership is still genuinely worth maintaining, viewed honestly from both sides.

Scaling to 30 People and the Move to Integrated Systems (2019)

By 2019, the agency had grown to approximately 30 people and the boilerplates that had begun as internal efficiency tools were evolving into full products. This was also the period when project management, time logging, and operational software became fully integrated rather than loosely connected.

Previously, the team had used tools in their default state and worked around their limitations. At this point, integrations were built between systems, reporting became professional and consistent, and the entire workflow was streamlined. Jimmy described this as everything "fitting together in a more beautiful way." It was also, predictably, a period of resistance: not everyone liked the new ways of working.

His observation for the AI era: new tools are obviously valuable, but adoption is never frictionless. Only teams and agencies that are genuinely open to change will end up on the right side of new technology.

The First Acquisition and Going Remote (2020)

2020 brought two simultaneous upheavals. Angry Creative moved from an office-based model to fully remote working — not by choice, but because of the pandemic. At the same time, Jimmy made his first acquisition: a UK-based agency that came with its own complications.

The combined effect was jarring. The company went from roughly 30 people to 60 almost overnight, while simultaneously losing the physical infrastructure of an office. Jimmy is direct about the difficulty: working in an office and working remotely are nothing alike. The office provides a support system — informal communication, spontaneous problem-solving, visibility of what everyone is doing — that remote work simply does not replicate.

Remote work, however, opened up the talent market in a way that office-based hiring never could. He made the point that in a smaller city, you can find decent people but you are unlikely to find exceptional ones. Remote removes that geographic ceiling. He was clear that accessing better talent remotely is not primarily about cost — genuinely skilled people are not cheap regardless of where they live. It is about reach.

The acquisition itself was turbulent because Jimmy did not yet have experience managing the HR and cultural complexity that comes with merging two companies. He reflected that he could have benefited from advice he only developed the capacity to give himself years later.

Managing 60 to 70 People: HR Drama and Bringing in an External CEO (2020 to 2021)

Running a 60-to-70-person agency turned out to be a genuinely miserable experience. Jimmy described it plainly: it was HR problems more or less every week, drama at scale, and a constant series of management fires to put out.

A recurring theme was that most people treat work as a distinct compartment of life, separate from their identity and interests. Jimmy does not experience it that way — work has been his life. This gap in orientation created friction. Workplace relationships formed, drama followed. People were not aligned around the same sense of purpose.

He also discovered that some staff who had come in through the acquisition were not, in any meaningful sense, working. They were performing the appearance of work. Finding this out and acting on it was "heartbreaking" in his words — not because he was surprised they were removed, but because he found it genuinely difficult to believe people would behave that way. Three people were eventually let go for this reason.

In response to all of this, Jimmy made a structural decision: he shifted his own focus away from day-to-day management and toward R&D, the work he actually finds meaningful and valuable. He hired an external CEO to run the business. His rationale was honest — he is not wired for management politics, and forcing himself into that role was making both him and the business worse.

His observation about team size carries real weight: 20 to 25 people is the practical maximum for any single manager to oversee effectively. Beyond that, you need a middle management layer, and building that layer is complex, political, and not suited to every founder.

The Contraction and the AI Pivot (2022 to 2023)

2022 brought the end of the pandemic-era boom. The combination of post-COVID economic normalisation, the war in Ukraine, and tightening budgets across the economy meant that the money that had been flowing freely into agencies dried up. The frothy conditions of 2021, when clients were "throwing money" at the business, gave way to something more austere.

Jimmy made a decision that he describes as deliberate and liberating: stop growing and start rebuilding. He had 70 people and was delivering worse output than when he had 30. He decided to use the recession and the emerging AI toolset as the conditions in which to redesign the business entirely.

The contraction happened for two reasons simultaneously. First, some business was lost in the downturn. Second, standardisation revealed that many people were no longer needed because the work they had been doing was now handled by prebuilt packages and systems.

Jimmy offered a memorable example: one staff member had spent his entire working day doing nothing but buttons — and was not particularly good at it. Once Angry Creative built a proper button component, that role disappeared. More poignantly, that person turned out to have no interest in doing anything other than buttons, and no appetite for reskilling. This was the pattern at smaller scale throughout the team.

In parallel, he launched an AI marketing vertical — something he had long wanted to do but had been held back from by the difficulty of finding writers who could produce consistent, quality content. AI tools changed that equation. A decent writer with the right tools could now produce great content. He built that into a service offering.

The deeper work was redesigning every internal process with AI in mind rather than retrofitting AI onto existing workflows. Jimmy was emphatic on this point: you cannot simply put AI on top of what you already do and expect transformation. You have to go back to first principles, understand every layer of your process, and rebuild from there. This is what Angry Creative did between 2022 and 2023. The result was the removal of most of the middle management layer — not because those people were fired wholesale, but because the tasks that had justified their roles no longer existed.

You have to go back to first principles, understand every layer of your process, and rebuild from there.

Further Acquisitions and the Architecture of a Leaner Business (2024)

Having made Angry Creative efficient enough to have genuine capacity, Jimmy returned to acquisitions in 2024 — acquiring three agencies in a single year. This time the process went significantly more smoothly. He attributed the difference entirely to experience: he knew what to look for, what problems to anticipate, and how to handle the integration process.

The acquisitions allowed him to add new verticals. One acquisition brought a team of designers he describes as "delivery designers" — people who handle both the design and the WordPress implementation, taking full responsibility for building what they design. This vertical has more work than it can comfortably handle.

The technical evolution of the business during this period also involved a shift in tooling philosophy. Angry Creative had built its core offering on ACF (Advanced Custom Fields), which worked well for several years and generated substantial ongoing support revenue because clients would regularly need developers to make changes. As standardisation took hold and page builders matured, the agency moved to Gutenberg as its primary framework.

Some of the acquired agencies were Elementor and Avada shops, which created a period of adjustment as different technical approaches were reconciled.

Jimmy observed that page builders effectively destroyed the junior developer role at agencies like his. The simplified tooling removed the entry-level work that had previously justified keeping junior staff. Then AI arrived and "finished off the rest." The outcome is a business with a clear two-tier technical structure: senior developers at Angry Creative doing complex, performance-critical WooCommerce work, and delivery designers handling design and implementation at another level.

Where the Business Stands Today (2025 and Beyond)

By 2025, Angry Creative was back to approximately 25 to 26 people. Turnover had decreased slightly from its peak — by around 15% — but the staff count had fallen by 55% relative to the revenue being generated. Jimmy framed this as one of the most significant achievements of his career, while adding a characteristically self-aware caveat: looking back in ten years, he might consider those "rookie numbers."

He is currently in the process of acquiring another agency and has just launched an AI automation and marketing offering that is gaining traction quickly. The business is growing again toward 30 people, but this time on entirely different terms.

The metric he now tracks most closely is break-even date within the month. At the time of the talk, the business reaches break-even within two to three days of the start of each month, meaning that everything earned after that is margin. His goal is to push that further.

One significant ongoing cost is a 1,000-square-metre office he signed a lease on just before the pandemic, which he described, with dry humour, as a decision he "only thinks about daily." With roughly six people using it and a cost of approximately 300,000 per year, it is a source of ongoing financial pressure. The lease expires in June of the following year (relative to when this talk was recorded), at which point he expects to be in a significantly better position.

On the Joy of Running a Smaller, Purposeful Business

One of the most personal threads in Jimmy's talk was his evolving relationship with the concept of a "lifestyle business." In the past, he considered it an embarrassing label — something lesser than running a "real" agency. He now sees it entirely differently.

He described what his host Andrew called JOMO — the Joy of Missing Out. Jimmy has opted out of the HR drama, the middle management politics, the chasing of headcount metrics. He has built a business that is aligned with the way he wants to live and work. He wakes up most mornings genuinely looking forward to the day.

He tied this to a core value: he loves helping clients and adding value to them. That is, in his words, what he optimises for. When the people around him share that orientation, the work environment becomes something he described as "beautiful." He said he loves everyone currently in the business, which is something he could not have said during the peak-headcount years.

He was clear that this did not happen quickly or easily. It took more than 20 years, one near-bankruptcy, a failed external CEO experiment, a 70-person catastrophe, and a deliberate dismantling of what he had built to arrive at something he actually wanted.

On Politics, Enterprise Sales, and the WooCommerce Ecosystem

In the Q&A portion of the session, Jimmy touched on a frustration that clearly runs deep: the political dimension of enterprise sales that he has largely avoided, to his business's detriment.

Angry Creative has invested what he estimates is around 100,000 hours building out its WooCommerce platform. It is capable of handling catalogues of 100,000 to 500,000 products and delivering performance that Jimmy describes as "second to none." He has taken clients from relatively modest scale to significant revenue on the back of this platform. And yet, the business repeatedly loses large enterprise deals not because of the quality of its work but because of relationship dynamics at the C-suite level.

His description of the problem is direct: the agencies that win enterprise deals are not necessarily better. They are the ones wining and dining the decision-makers, playing golf with them, building personal relationships. Technical excellence is not enough at that level of procurement. He acknowledged this is a gap he intends to close, describing plans to create dedicated time in his schedule for what he calls "political work" — building relationships with the people who actually make purchasing decisions.

He is self-aware about why this has not come naturally. He describes himself as a neurodivergent person with autism and ADHD — a profile he mentioned openly and without apology. He identifies as a nerd and an inventor. Playing relationship games at the C-suite level is not where he is most comfortable. But he recognises it as a business requirement at the level he is trying to operate.

The host Andrew offered a vivid illustration of how relationship-based enterprise sales has historically worked: 12-hour days with a client, breakfast through golf through dinner, all culminating in a contract signing that felt almost impossible to refuse. Andrew framed this as what Atarim does through "dropping deposits" — going to events, making friends, building long-term personal trust so that when it comes to signing, clients feel they know the people they are choosing.

On Gutenberg, Page Builders, and Technical Philosophy

The final substantive exchange of the session was a question about whether the Gutenberg full-site editor meets Angry Creative's needs as a page builder.

Jimmy was candid. When Gutenberg first launched, it was, in his words, "really bad." Even now, he said, if you download WordPress and try to use Gutenberg out of the box, it is not good enough for professional work.

What Angry Creative has done is extend Gutenberg extensively over many years. The agency maintains approximately 60 plugins and a significant library of custom blocks, as well as back-end software that handles much of the heavy lifting in their WooCommerce packaging.

All of these components have to be aligned with each other, which is a significant ongoing engineering commitment.

His advice to anyone starting fresh today is unambiguous: do not try to replicate what Angry Creative did with Gutenberg. It is the product of years of investment and a very specific set of circumstances. For a freelancer starting out, or even a small agency, a commercial page builder such as Beaver Builder or Elementor is the rational choice.

Where Gutenberg excels, in his view, is in larger, more complex builds where staying close to WordPress core matters and where performance optimisation needs to reach a level that third-party page builders cannot achieve. The trade-off is that only a small fraction of clients actually need that level of performance. Most clients' sites are not performance-constrained in a way that would justify the investment.

He also acknowledged that the acquisitions of Elementor and Avada agencies brought a different technical culture into the business, and managing the coexistence of those approaches has been part of the challenge of the past few years.

On Remote Work vs. Office Work

Jimmy's framework for thinking about office versus remote is one of the more practically useful ideas in the talk. Rather than treating it as a binary question, he distinguishes between two types of work.

For experienced staff doing well-defined, measurable work — such as his senior developers delivering complex WooCommerce builds — remote works extremely well. The tasks are understood, the standards are established, measurement is straightforward, and the quality of talent available globally far exceeds what any single city can offer.

For emergent work where the rules are still being written — he cited his AI team as the prime example — an office environment is meaningfully better. When no one knows exactly what tomorrow will bring, the ability to turn to a colleague, show them something on a screen, or have a spontaneous ten-minute conversation is genuinely valuable in a way that Slack huddles do not replicate. He noted that Automattic keeps its AI team in a physical New York office for this reason.

The broader loss from remote work, which host Andrew reflected on at length, is the informal support structure of a shared physical space: the ambient awareness of what others are working on, the low-friction interruption, the ability to read the room. These things are genuinely lost in a remote-first model, and no amount of good tooling fully replaces them.

About the speaker Jimmy Rosen Angry Creative

Jimmy Rosen leads Angry Creative, a digital agency, and speaks candidly about what it actually took to build the agency he set out to run.