Q&A with Josh Barrett of Matchstick Legal: Building a Legal Playbook for Creative Agencies
As the creative agency landscape becomes more complex, shaped by AI, shifting scopes, remote teams, and evolving client expectations, the legal foundation behind the work has never been more important. Ahead of his upcoming NextNW webinar, “A Legal Playbook for Creative Agencies,” we sat down with Josh Barrett, attorney and founder of Matchstick Legal, to discuss the biggest risks facing agencies today and how leaders can build strong legal habits that protect both their work and their business.
Here’s our conversation with Josh.
Q&A
Q1. You’ve built Matchstick Legal specifically around the needs of creative agencies. What inspired you to focus your practice on this niche, and what gaps did you see in the legal support available to agencies?
A:The inspiration largely comes from seeing the cool stuff our clients make. But from a legal perspective, most business lawyers don’t understand the uniqueness of how agencies operate or the work that they do. So while any business lawyer can edit a contract, we know the areas of particular concern for creative agencies and how they are different whether you are making a website, a brand identity, a video, a digital marketing campaign, or a project including all of these things.
Q2. For agency leaders attending the webinar, what are the most common legal blind spots you see—especially among small to mid-sized creative shops?
A: Most agencies are afraid of their clients. They are afraid to negotiate, afraid to ask for what they need, afraid to hold the client to its commitments, afraid to talk about difficult issues, etc. And when an agency is unwilling to do these things, they often end up getting pushed around by their client. Not only is this unpleasant, but it leads to lower profitability, higher risks, and unsatisfying client relationships.
Q3. Your webinar title references a “legal playbook.” If you could pick just one “must-have” play every agency should implement immediately, what would it be and why?
A:Two things come to mind. First, at the earliest stages of a conversation with a client about potential scope and fee, the agency should communicate that the proposed fee assumes that the clients terms will govern the relationship. And that if the client insists on its terms or major modifications to the clients terms, the fee may change accordingly. In other words, don’t just adjust fees for deliverables, adjust fees for risk allocation. But you need to set the stage for this early in the relationship to have success implemeting it later. Second, most agencies have confused free work with client service, and as a result, end up doing lots of free work because they think it is needed to keep the client happy. The reality is in fact the opposite. Doing free work just sets the stage for a client to take advantage of your agency in the future.
Q4. Contracts are a frequent pain point for agencies. What misconceptions do agency owners often have about their contracts, statements of work, or master service agreements?
A:Most agencies think a contract is only there for a lawsuit in case the relationship blows up. In fact, this is quite rare. The most valuable reason for a contrat is managing expectations during a relationship. A well-drafted contract gives a agency’s project managers a place to stand when pushing for late client deliverables, opening a change order, or terminating to get away from a toxic contract. We think of contracts as scaffolding and support points for the difficult conversations that come up during an engagement. With a solid place to stand, an agency is in a much better position to protect it’s margin and get paid for every ounce of work..
Q5. Scope creep, IP ownership, and payment issues are perennial challenges. Which of these tend to create the biggest legal risk for agencies, and how should leaders think about mitigating them proactively?
A:Scope creep! All scope creep is a self-inflicted wound. New scope that a client pays for is just a change order and not a problem. New scope is only a problem if the client does the work for free. Scope creep is the name agencies have come up with to blame clients for what the agency is doing to itself. The reality is, if a client asks for something outside of scope, then it is the agency’s job to turn that into a change order. But most agencies are afraid of giving that news to a client, so they do the work for free, to the detriment of their teams, their margins, and their satisfaction.
Q6. Many NextNW members are independent contractors or freelancers. What are the most important protections they should negotiate when working with agencies or clients?
A: A freelancer is just a small agency. Lots of the issues are the same. Scope creep is as real of an issue for freelancers as it is for an agency. But I think lots of freelancers have it in their power to get paid all or substantially in advance. Freelancers should push for that when they can. One way to do this is by offering the freelancer’s normal price for payment up front and 120% of that amount if fees are paid net 30. Honestly, all agencies should do this too.
Q7. You’ve worked with a wide range of creative businesses. Are there emerging legal trends—AI, data privacy, remote work structures—that agency professionals should be paying attention to right now?
A: AI is probably the most rapidly developing issue right now. In some areas, use of AI is industry standard (e.g., coding). In other areas, it is highly restricted or risky (e.g., using AI visual outputs in customer-facing campaigns). There is no one size fits all approach as the right response depends on the client and the deliverables.
Q8. For agencies that don’t yet have formal legal counsel, how do you recommend they prioritize what to build first: stronger contracts, risk management processes, compliance frameworks, or something else?
A:Most creative service providers (whether agency or freelancer) typically benefits most from having a good master services agreement and SOW plus understanding how to use it to navigage those difficult conversations.
Q9. Matchstick Legal emphasizes plain-language guidance. Why is clarity—in contracts, negotiations, and communication—so critical in reducing risk and aligning expectations?
A: For some reason, most people try to write contrats they way they think a lawyer would write. And AI is making it much, much worse. The obvious tell is when I see a home-spun contract write numbers like “thirty (30) days” (there is no reason to do this).This is a silly example but the problem with bad writing is that the form gets in the way of the substance. Good writing for contracts is the same for any other type of communication. We find that well written contracts get negotiated more quickly (meaning you can collect a deposit and start paying work more quickly), increase client satisfaction (because the language isn’t obscure and things move quickly), decrease risk (because everyone understands what is happening), and make for smoother projects (because likely trouble points are addressed in advance). Also, a well written contract says something about your shop. It says you communicate well, you care about details, you want people to understand, etc. Those are all positive attributes for any business.
Q10. Without giving too much of the webinar away, what is one practical takeaway attendees will walk away with that they can apply to their agency the same week?
A:Holistically, I hope attendees feel empowered and equipped about how to have difficult conversations during a project to avoid “scope creep (and free work). More concretely, attendees will understand how to use a Pricing Matrix to make more money in their proposals. Both of these are easily implemented and concrete steps to make your business run better and be more satisfying to you in 2026.
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