Smart Agency Masterclass with Jason Swenk: Podcast for Digital Marketing Agencies

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942 episodes
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Date created
2014/04/27
Latest episode
2026/04/22
Average duration
32 min.
Release period
4 days

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Growing an agency is very difficult, and you might feel unclear what to do next in order to grow and scale your agency. The Smart Agency Masterclass is a weekly podcast for agencies that are wanting to grow faster. We interview amazing guests from all over the world that have the experience of running successful businesses, and will provide you the insights you need. Our podcast is just over 3 years old, and have reached more than a half million listeners in 42 countries.

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The CEO Trap: Why Founders Either Check Out or Can't Let Go with Matt Nelson | Ep #899
2026/04/22
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Does growth break agencies or does it expose underlying issues? It happens more often that founders expect. Even with momentum, scrappy decisions, loose roles, and unspoken agreements eventually become the very thing that holds the business back. And by the time it's visible, it's no longer a small fix. It's structural. Today's featured guest pulls back the curtain on that transition. He dives into the messy reality of starting an agency, navigating partner exits, building leadership layers, and the constant internal battle founders face when trying to let go. This isn't about tactics, it's about identity, structure, and the discipline required to stop being the bottleneck. Matt Nelson is the owner of First Tracks Marketing, an agency specializing in e-commerce, web development, and digital marketing programs. Unlike many agencies that niche down aggressively, Matt has built his firm around a repeatable process that adapts across industries. Over the years, he transitioned from being an employee to the sole owner, buying out partners, rebuilding the company's structure, and installing a leadership team that allows him to step back from day-to-day operations. In this episode, we'll discuss: How he learned to create a proper framework for a partner exit The lack of vision in his agency's early days The most significant shift: A leadership layer Two CEO traps that mess with the agency's growth Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. A Reactive Start That Created Complexity Down the Line Matt didn't start his agency with a grand strategy. Like many founders, it began out of frustration, leaving a poorly run agency and deciding to "figure it out" on his own. In his case, he worked at an agency that resisted change. In 2008, they still regarded digital work as a fad they would outlast. This frustrated Matt, who sensed this technology was the future of agencies. He wasn't the only one who felt this way, so he joined a couple of co-workers who decided to leave, rented an office across the street, and started their own business. This group had the vision but lacked structure, and this was evident early on. There were no operating agreements, unclear roles, and partners bringing in uneven value. At the time, it worked because momentum masked the problems. But as the business grew, those gaps became liabilities. This is where most founders get caught. They assume early success equals a solid foundation. In reality, early-stage growth often hides structural weaknesses, until scale forces those issues to the surface. If you don't build structure early, you'll pay for it later, either in painful partner exits, stalled growth, or both. Partner Misalignment Is a Structural Risk, Not a Personal Issue As the current sole owner, Matt has had to navigate multiple partner exits in the years since joining the business as an employee. These mostly happened not because of conflict, but because of misalignment. Different timelines. Different expectations. Different levels of contribution. The first exit was messy because there was no framework. There was no agreement or predefined process. Just emotion and negotiation. The second exit was different. By then, they had implemented an operating agreement, defined terms, and created a clear path for transition. That structure turned what could have been chaos into a controlled process. Most founders avoid these conversations early because things feel "fine." But without clear agreements, you're building risk into the business from day one. Why Lack of Vision Breaks Agencies Before Matt became the sole owner, the agency lacked a clear direction. They were doing good work and clients were happy. But there was no defined trajectory. That's a dangerous place to be. When there's no vision, the business defaults to activity. Projects get done. Revenue comes in. But nothing compounds. Matt's turning point came when he pushed for a strategic shift, relocating the agency to access better talent and reduce costs. He was thinking beyond execution and into positioning, hiring, and scalability. This is where founders start to separate. Operators focus on output. Leaders focus on direction. You Don't Scale Until You Build Leaders Under You The biggest shift in Matt's agency came when he installed a leadership layer: Creative Director Director of Development Director of Marketing Each owns a function, manages their own team, and is accountable for outcomes. It's a shift many founders resist. They hire doers, but not leaders, and then wonder why everything still runs through them. But real scale happens when decisions are pushed down, not escalated up. That's the difference between having a team and having a business that runs. Letting Go Isn't a Skill, It's a Discipline Even with structure in place, Matt still feels the pull to jump back in. Checking tickets. Fixing issues. Responding to clients. That instinct doesn't go away. What changes is how you manage it. Instead of stepping in directly, he routes issues through his leadership team and tries to reinforce accountability. It's still difficult for him and it's a point where most founders regress. They install systems, but break them under pressure. Choosing not to step in, even when you could, is about restraint. Because every time you do, you train the business to depend on you again. The CEO Trap… Boredom or Interference? Once you reach the CEO level, there are two ways you can get in the way of your agency's success: You jump back in to feel needed. You disengage because you feel irrelevant. Both break the business. Matt's solution has been creating structured involvement, quarterly planning, defining "rocks," and aligning the leadership team around long-term direction. This keeps him engaged at the right level, without collapsing back into execution. The goal isn't to remove yourself completely. It's to operate at the level the business actually needs. Incentives Drive Behavior, Not Motivation Matt is very aware that the agency's success lies with the team and their involvement and motivation. That's why he implemented a profit-sharing model. Not as a perk, but as alignment. When the team benefits directly from performance, they think differently. They take ownership. They care about outcomes, not just tasks. Most agencies struggle with engagement because there's no connection between effort and reward. With this model, he's managed to flip that. If the business wins, the team wins first. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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The Invisible Ceiling Most Agency Owners Never See Coming with Brandon Harrar | Ep #898
2026/04/19
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What if growth isn't actually about more clients, more hires, or even more revenue? What if the very thing driving your success right now is also the reason you'll eventually stall? Agency owners tend to chase the usual milestones: bigger deals, a growing team, rising top-line numbers. And for a while, that works. But there's a breaking point most founders don't see coming when the business can't grow any further because everything still runs through them. Today's featured guest will unpack what actually happens as you move from freelancer to agency, and then hit the ceiling most founders never see coming. We dig into why layering account management changes everything, how referral-driven growth can both sustain and trap you, and the real reason many founders resist scaling past a certain size. This is a conversation about control, identity, and the uncomfortable truth: the thing that got you here is exactly what's holding you back. Brandon Harrar is the founder and creative director of HRVST, a boutique agency he started 14 years ago from a $500 project he had no formal experience delivering. Since then, he's built a steady, referral-driven agency focused on design and development, intentionally keeping the team lean (around 12–15 people). His journey is a case study in sustainable growth without outbound sales, and the tradeoffs that come with it. Brandon brings a grounded, operator-level perspective on hiring, leadership, pricing models, and why not every agency should scale the same way. In this episode, we'll discuss: Making an early role shift Learning to set the right expectations for clients Managing vs leading Why referral growth is structurally fragile Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. Herringbone Digital: If you're thinking about exiting now, planning a few years ahead, or just want to understand your options, you should know about Herringbone Digital. They're not a typical financial buyer. They're operators who actually understand what it takes to build and scale an agency because they've done it themselves. Their approach is simple: invest in great founders, protect what's already working, and help agencies scale faster. Go to https://www.herringbonedigital.com/swenkand start the conversation. The First Real Shift: From Freelancer to Agency The first constraint most founders hit while growing their agencies is capability, and for Brandon, it happened almost immediately. He realized he wasn't good enough at design to deliver the level of work required. That forced the first identity shift: from doing the work to building a team that could. This is where most freelancers accidentally become agency owners. Not because they planned it, but because the work demands it. And once you make that shift, everything changes. You're no longer optimizing for output, you're optimizing for people. The second shift came from something most founders don't expect: emotional friction with clients. Brandon realized he didn't want to be the one receiving raw feedback, which often implied having to go along with changes he didn't necessarily feel were correct. So he inserted account management as a buffer. That's a structural decision most founders delay too long. Without that layer, you stay emotionally entangled in delivery. With it, you start building a system. Learning to Set the Right Expectations Another lesson Brandon learned fast was that one of the fastest ways to destroy a project is misaligned expectations. Presenting work as "the best we've ever done" may feel like confidence. In reality, it sets an impossible bar. When the client doesn't love it, the gap between expectation and reality becomes unfixable. That's the mistake most founders make early on. They try to sell certainty instead of framing a process. Because the truth is clients don't actually know what they want. They think they do. But what they're really buying is your ability to interpret, challenge, and guide. If you position your work as "perfect," you remove space for that collaboration. As Jason explains, the real shift happens before the project even starts. Reframe the sales conversation to: "We're going to use your data, apply our expertise, and challenge you." That single expectation changes the entire dynamic. Now the client understands that this isn't order-taking. This is a partnership. And more importantly, it gives you permission to push back when needed. Managing vs. Leading. Where Most Founders Get Stuck There's a subtle but critical difference between managing tasks and leading outcomes. Early on, most founders default to control: "Do it this way." "Follow this process." But Brandon describes a shift that changes everything: Giving direction, not instructions. Instead of prescribing how work gets done, he provides context, lets the team execute their way, and asks that they document their process. That does two things: It builds ownership It evolves the system organically This is how you move from being the bottleneck to building a machine. It won't be easy. Mistakes will be made and founders many times fall into the trap of stepping in too early with the solution. You see the mistake coming. You know how to fix it in 10 seconds. So you jump in. But that 10-second save creates long-term dependency. The team learns: "Wait for the founder." The real discipline is letting small mistakes happen so the team builds confidence. You're not preventing failure, you're designing learning cycles. Why Referral Growth is Sustainable, But Structurally Fragile Brandon's agency has grown for 14 years without outbound sales. That's rare, and on the surface, ideal. In his case, the engine has been consistently delivering work that leaves clients satisfied enough to refer. This creates a steady flow of opportunities without the pressure of building a sales machine. But there's a hidden constraint: lack of predictability. Every January feels like starting over. That's the tradeoff with referral-based growth. It's stable over time, but volatile in the short term. You don't control demand, you inherit it. The other key lever is clarity in positioning. Brandon's agency doesn't do everything. They focus on design and development. That specificity makes referrals easier: "You need X? Talk to Brandon." Without that clarity, referrals become vague, and vague referrals don't convert. Why Founders Resist Scaling Brandon openly says he doesn't want a 50–100 person agency. That's not what success and growth look like for him. In fact, he sees having a bigger team as adding risk, complexity, and responsibility. But is that necessarily the case? That fear usually comes from operating at the wrong role. At 15 people, if everything still comes to you, scaling feels impossible. You imagine 100 people all needing your input. That's overwhelming. But that's not what scaling actually looks like. At scale, problems don't come to you, they get solved without you. Leadership layers handle execution so you can focus on direction. If you're still the manager at 15 people, 50 feels terrifying. If you become the architect, 50 becomes easier than 15. The Real Conversation Isn't Hourly vs. Value Brandon believes the debate between hourly and value-based pricing misses the point. It's up to every agency owner to decide which works best for their business. For his part, he's currently running a hybrid model, since there are advantages to both. When done right, the hourly pricing agency model can work very well. And, with the right client base and infrastructure, so can the value-based model. However, both Jason and Brandon agree on one non-negotiable: You must track time. Without data, you can't understand efficiency, capacity, or profitability. From there, the model depends on context: Unknown scope → hourly Repeatable work → fixed or value-based How you price determines how clients see you. Hourly pricing positions you as a task executor. Value-based pricing positions you as a problem solver. And that distinction shapes everything, from client expectations to margins. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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How to Build an Agency That Doesn't Depend on You with Ted Harrison | Ep #897
2026/04/15
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you struggling to scale your agency or are you unknowingly the thing holding it back? At what point does your growth stop being a systems problem and start becoming a leadership one? Today's guest shares what it to break through those ceilings. After scaling quickly off the back of a strong network, he made the critical decision to systemize everything before growth turned him into the bottleneck. By leveraging documentation in a smart, intentional way, he built a foundation that allowed the agency to grow without everything running through him. In this conversation, he unpacks the realities of working with enterprise clients, the often uncomfortable shift from operator to CEO, and why—despite all the noise, AI is actually increasing the need for human judgment, taste, and leadership, not replacing it. Ted Harrison is the CEO and founder of Neuemotion, a fast-growing B2B creative agency working with enterprise brands. Before launching his agency, he spent seven years at Twitter (later X), where he led advertiser production, helping global brands create better-performing content at scale. After navigating the chaos of a major corporate transition, Ted left to build an agency where he could control decisions, scale creative impact, and architect a business on his own terms. In this episode, we'll discuss: Avoiding the trap of confusing early traction with a scalable model Leveraging documentation early Enterprise clients as a double-edged sword Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. The Hidden Trap of Scaling Expertise Leaving Twitter a year after the acquisition ultimately created opportunities for Ted's newly founded agency. Many had left long before him, had already found new jobs, and proved to be valuable contacts for potential clients. Ted tapped into this powerful network, and the access to enterprise clients helped him build momentum and fast growth. However, that same advantage creates a structural risk: those clients don't initially trust the agency, they trust you. This is where most founders get stuck. They confuse early traction with a scalable model. In reality, they've just extended their personal brand into a slightly larger container. The real challenge is transferring trust. If you don't systemize your thinking, your decision-making, and your taste, every new client reinforces dependency. The agency grows, but so does the founder's involvement. And eventually, growth slows, not because of demand, but because of capacity. Documentation as a Scaling Weapon (Not a Nice-to-Have) Luckily for Ted, by the time he started the agency, he already understood the importance of documenting processes, which has helped him greatly as he initiates his transition out of operations. Instead of relying on shadowing, tribal knowledge, or ad hoc training, Ted documented his thinking through a book, internal frameworks, and structured onboarding. Every new team member consumes that context upfront. This does two things most agencies miss: First, it compresses onboarding time. Instead of months of "figuring it out," team members immediately understand how decisions get made. Second, it creates consistency without rigidity. The team isn't copying Ted, but they're operating from the same mental model. This is the difference between delegation and true scale. Without documentation, you're forced to stay involved because no one else "thinks like you." With it, you create a system where people can make aligned decisions independently, while still bringing their own perspective. The Operator → CEO Shift Is Uncomfortable (But Necessary) Ted is currently in the most dangerous phase for any founder: the transition from doing to leading. At ~20–30 employees, the cracks start to show. You can't be in every decision. You can't touch every client. And you can't be the quality control layer anymore. This is where many founders regress. They step back in when things break. They reinsert themselves into delivery. They become the "fixer" again. But that behavior reinforces the very bottleneck they're trying to escape. The real shift is identity, not activity. As an operator, your value comes from execution. As a CEO, your value comes from clarity, structure, and direction. If you don't make that shift intentionally, the agency will stall right at the point where it should scale. AI Is Not Replacing Agencies, It's Exposing Them At his agency, Ted's team is using AI in two ways. At the client level, they're mostly building agents, using it to clean up audio and video, and using its output as a starting point. Internally, they have their own "TedGPT", which has proven to be a great tool to scale knowledge. When it comes to how his enterprise clients are using it, Ted has seen that rather than replacing agencies with AI, they're hiring agencies to fix what AI broke. Why is this? Because AI lacks taste, context, and lived experience. It can generate and optimize. But it can't decide what matters. That's where agencies still win, if they position correctly. The real risk for agencies is doing work that AI can replace. Low-level execution, undifferentiated production, and generic output are already commoditized. Enterprise Clients Are a Double-Edged Sword Something Ted wishes he'd known before working with enterprise clients is that it introduces a level of complexity most founders underestimate. Long payment terms. Free pitch work. Endless stakeholder input. Constant shifting priorities. It's both harder and structurally different. Like most founders who have worked with enterprise clients, Ted eventually realized that the bigger the client, the more operational friction you inherit. That doesn't mean you shouldn't work with them, but it does meanyou need to build systems that protect your agency from them. Without strong positioning, pricing discipline, and process control, enterprise clients will consume your team, and your margins. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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Why Most Agency Acquisitions Fall Apart (And What Buyers Actually Want) with Azim Nagree | Ep #896
2026/04/12
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Why are more agencies selling right now? If this trend has made you think about selling, is it because the market is hot… or because you've outgrown your role? If you're seriously thinking about selling your business, you should know that it'll ultimately come down to whether it can survive without you, and whether you want it to. Today's featured guest breaks down what's really driving the surge in agency acquisitions right now. He goes beyond surface-level multiples and unpacks what buyers actually look for, why most founders sabotage deals during diligence, and how AI is quietly separating premium agencies from the rest. This conversation will challenge how you think about growth, ownership, and your role in the business. Azim Nagree leads M&A Origination at Herringbone Digital, a private equity-backed platform acquiring and scaling digital marketing agencies. Originally trained as an M&A lawyer in Australia, Azim quickly realized he didn't enjoy the legal side of deals, but loved the strategy and deal-making behind them. Over the past 5–6 years, he's focused exclusively on agency acquisitions, working with founders navigating exits, partnerships, and scale. He brings an operator-meets-investor perspective, understanding both what founders want and what buyers actually value. In this episode, we'll discuss: Why are PE firms interested in agencies? 3 filters most agencies won't pass. The silent deal killer Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. Herringbone Digital: If you're thinking about exiting now, planning a few years ahead, or just want to understand your options, you should know about Herringbone Digital. They're not a typical financial buyer. They're operators who actually understand what it takes to build and scale an agency because they've done it themselves. Their approach is simple: invest in great founders, protect what's already working, and help agencies scale faster. Go to https://www.herringbonedigital.com/swenk and start the conversation. The Real Reason Agencies Are Getting Acquired Right Now There's a massive misconception in the market that agency acquisitions are happening because agencies suddenly became more attractive. That's not the full picture. What's actually happening is a capital problem, not an agency problem. Private equity is sitting on over $1 trillion dollars of unallocated capital. That money has to be deployed. And agencies, when structured correctly, check a lot of boxes: recurring revenue, strong margins, and fragmented markets ripe for consolidation. That's why you're seeing more deals. Not because every agency is valuable, but because capital is aggressively looking for places to go. However, you can't assume that just because deals are happening, your agency is ready to be bought. It's likely not. Buyers aren't just looking for revenue. They're looking for structure, predictability, and independence from the founder. If your business still relies on you for sales, delivery decisions, or client retention, it's not an asset. It's a job with revenue attached. And buyers know the difference immediately. 3 Filters Every Serious Buyer Uses Most founders think deals come down to valuation. In reality, every serious buyer is evaluating three things before they even care about price: 1. Strategic Fit Why does this deal exist? If there's no clear reason, new market, new capability, better economics, it's dead on arrival. Buying (or selling) just because it "feels like the right time" is how bad deals happen. 2. Cultural Fit This is the one founders underestimate the most. You're not just selling a business. You're entering a relationship that could last years. If there's friction early, it doesn't get better later. And forcing alignment for the sake of a deal almost always ends badly. 3. Financial Reality This is where the truth shows up. You can't "position" your way past bad numbers. Buyers will find churn issues, margin leaks, and unstable revenue during diligence. Trying to hide it just wastes months, and kills trust. The strongest sellers aren't perfect. They're transparent. The Silent Deal Killer: Founder Behavior During Diligence Here's something most people won't tell you: Deals don't usually fall apart because of numbers. They fall apart because of founder behavior during the process. Diligence takes 3–6 months. And during that time, many founders mentally check out. They assume the deal is done and take their foot off the gas. They start thinking in terms of "their problem soon, not mine." That's where things break, clients churn, and revenue dips. Key employees sense uncertainty and start looking elsewhere. And suddenly, the business the buyer evaluated is not the business that exists anymore. From the buyer's perspective, that's a red flag. The rule is simple: Run the business like you're never selling it, even when you are. Ironically, that's what makes it sellable in the first place. The Real Question: Should You Sell? Selling isn't just a financial decision. It's also a personal one. The best founders who sell have clarity on two things: What they want to do next Whether they've truly outgrown their current role  Regarding the first one, there's no wrong answer. Some buyers are looking to transition the founder out of the business in just 3-6 months. Some are looking for founders who want to stick around for a few years. The important thing is to be honest about your plans. Without that clarity, selling often creates more problems than it solves. Because removing yourself from the business doesn't automatically create purpose. AI Isn't Increasing Valuations. Bad Thinking Is Lowering Them A lot of PE firms are buying agencies based on their use of AI. Now, what these firms are looking for is AI as strategy, and using ChatGPT for content is not a strategy. That's a tool. Buyers don't care if you use AI tools. They care if AI shows up in your business fundamentals. This means that effective use of AI would show up in: Higher margins  Lower cost of delivery  Increased retention  Better client outcomes  Faster execution  If AI isn't impacting those metrics, it's irrelevant. The agencies commanding higher multiples right now aren't "AI agencies." They're system-driven agencies using AI to enhance leverage. They've embedded AI into workflows, decision-making, and delivery, not just content creation. A powerful example shared in the episode: One agency built a custom AI model for every client using all available data, sales conversations, onboarding insights, business goals. That model informs everything: Campaign strategy Reporting Communication style Execution  The result is that every client feels like the only client, without increasing workload. That's leverage. And that's what buyers pay for. Ultimately, most founders understand they need to wrap their heads around the use of AI as a strategic advantage. Whether they're really doing it or not is another issue. So ask yourself if, other than requiring your team to use AI, you're actually investing in it, whether through training, creating roles centered on AI experimentation, or providing resources to support that learning curve. If not, you won't actually affect the metrics that matter. The Bottom Line on Agency Acquisitions The agencies that sell well aren't lucky. They're structured. They've built: Predictable revenue  Strong margins  Low founder dependency  Systems that scale  Selling is just a byproduct of that. Want to Know If Your Agency Is Actually Sellable? If you're thinking about selling, or just want to build a more valuable, less dependent agency, you need to understand where your bottlenecks actually are at a structural level. If you want to map that out with real numbers, real operators, and a proven sequence, the next step is simple: Join a room where this is the standard, not the exception. Check out Herringbone Digital to start a conversation. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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The Identity Crisis Killing Agencies (And How to Rebuild Before It's Too Late) With Jonathan Lewis | Ep #895
2026/04/08
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are agencies becoming obsolete? We don't think so. However, the traditional agency model isn't just evolving, it's breaking. Today's featured guest believes the core of every business is dying and that agencies that want to adapt and win need to adopt the mindset of rebuilders. He shares why agencies have been in decline for over two decades and what it actually takes to rebuild a business that survives AI, commoditization, and shifting client expectations. Tactics alone won't help because, at its core, this shift is about identity, positioning, and stepping into a new role as someone who doesn't cling to the old model but actively creates the next one. Jonathan Lewis is the President of McKee Wallwork, a brand strategy and implementation firm. Starting as an unpaid intern, Jonathan worked his way up to eventually acquiring the agency from its founders. Over the past decade, he's led the firm through a major repositioning, moving away from traditional agency work toward upstream strategic advisory. His perspective is shaped by firsthand experience navigating succession, industry decline, and the current AI-driven disruption. In this episode, we'll discuss: The declining agency model Why identity is the real problem Moving upstream The rebuilder mindset Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. The Agency Model Has Been in Decline for Years Most agency owners think the pressure they're feeling is recent, but it's not. Jonathan makes a strong case that the traditional agency model has been declining since the early 2000s, starting with the collapse of mass media dominance and accelerating through the rise of the internet, social media, and now AI. The old model was simple: control distribution, create decent creative, and scale results through reach. That model is gone. Today, agencies are fighting for perceived value in a world where clients question everything: speed, cost, necessity, and even whether they need an agency at all. This shows up in commoditized RFPs, price pressure, and constant comparison to cheaper or faster alternatives. The frustration many founders feel isn't personal failure; it's structural misalignment. They're trying to win using a model that no longer works the way it used to. The Real Problem Isn't AI, It's Identity A lot of agency owners are blaming AI for the disruption. That's not the real issue. The deeper problem is identity. Most agencies are built by craftspeople, designers, developers, media buyers who tie their value to the tools they use. When those tools become automated or commoditized, it creates an identity crisis. If your value is "I build websites" or "I run ads," you're in trouble. Because now those things can be done faster, cheaper, and in some cases better, without you. Your value is not the tool. Your value is the thinking before and after the tool, the judgment, the strategy, the ability to define what should be built and why. Moving Upstream: From Execution to Worldview In 2018, Jonathan and his team made a critical shift. They stopped trying to compete on execution and moved upstream into strategy, specifically, helping clients define their worldview. This is where things get interesting. AI can generate outputs. It can execute tasks. But it still depends on inputs, the prompt, the context, the perspective. That's where agencies have leverage. Instead of being the ones producing deliverables, they became the ones shaping direction. Helping clients answer: Who are we? What do we stand for? Who are we actually trying to reach? What matters most? From there, everything downstream becomes easier, whether it's done by internal teams, AI, or external vendors. This shift moves the agency from vendor to strategic partner. And more importantly, it removes them from the commodity trap. AI Is a Multiplier, Not a Replacement Jonathan takes a grounded view of AI. AI increases productivity dramatically. But historically, when something becomes more accessible, demand increases. Lower cost per unit doesn't eliminate demand; it expands it. The opportunity isn't in resisting AI. It's in integrating it while strengthening the human layer around it. You can use AI to analyze markets, generate insights, and accelerate content creation, not to replace thinking, but to enhance it. The real advantage comes from combining: Pattern recognition (AI) Judgment (human) Perspective (worldview) Agencies that only use AI for execution will get commoditized. Agencies that use AI to amplify strategic thinking will gain leverage. The "Rebuilder" Mindset Jonathan wrote a book around the idea of becoming a "rebuilder" because that's how he sees people getting through these times of reckoning in the business. Every major shift, from the internet, social media, COVID, and AI, breaks existing models. Most people respond by resisting, waiting, or reacting. Rebuilders do something different. They accept that the old model is broken and take responsibility for creating the next one. That means: Rethinking how you create value Redefining your role in the business Rebuilding your offer, positioning, and delivery model Leading your team through uncertainty instead of avoiding it It's ownership at a different level. And it's the difference between agencies that survive disruption and those that disappear with it. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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Why Hiring Without Systems Multiplies the Chaos with Chris Seminatore | Ep #894
2026/04/05
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What actually breaks an agency first, growth or the founder's inability to evolve with it? And at what point does hiring more people stop creating leverage… and start creating chaos? Today's featured guest dives into why he decided to close his first business, which he had grown to 22 employees, and start again solo. He needed to get away from the chaos of managing a large team, but what is the crucial mistake he can avoid if he ever wants to scale an agency team again? Beneath the tactics, it becomes clear that the role of a founder must grow if they want to build a business that doesn't collapse without them. Chris Seminatori is the founder of Get Geofencing, an advanced digital marketing technique that helps small and large-scale enterprises meet their sales target effectively and efficiently. Chris shared his journey from scaling a 20+ person operation in Beverly Hills to intentionally stepping away from team-heavy growth after experiencing the hidden cost: constant management chaos. He talks about the evolution of advertising, from geofencing to connected TV, and how emerging technologies like AI are reshaping both service delivery and agency efficiency. In this episode, we'll discuss: The trap of hiring to grow What was the crucial mistake? Control vs. dependency What the Navy got right Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. Herringbone Digital: If you're thinking about exiting now, planning a few years ahead, or just want to understand your options, you should know about Herringbone Digital. They're not a typical financial buyer. They're operators who actually understand what it takes to build and scale an agency because they've done it themselves. Their approach is simple: invest in great founders, protect what's already working, and help agencies scale faster. Go to https://www.herringbonedigital.com/swenk and start the conversation. The Trap: Hiring Only to Manage Chaos Chris's first business followed a familiar trajectory: start small, gain traction, hire quickly, and scale to over 20 employees. On paper, it looked like success, but it quickly became unsustainable. Each hire introduced new variables—different expectations, skill levels, and problems—until Chris found himself spending his days putting out fires instead of building the business. This is the inflection point many founders hit but don't anticipate. Growth creates complexity, and without structure, that complexity compounds. Instead of gaining leverage, Chris became the central node for every decision, issue, and escalation. The deeper issue wasn't the team itself. It was the absence of systems, clarity, and leadership infrastructure. Without those, hiring just amplifies chaos. Chris ultimately shut the business down, not because it lacked demand, but because it lacked structure. Why Most Founders Break When They Try to "Scale" Like many founders, Chris operated intuitively and ended up hiring before systemization. The "system" lived in his head, from how to deliver, solve problems, and serve clients. When he brought others in, they lacked the context and frameworks to operate independently. This created a loop: the team needed constant input, which pulled Chris deeper into operations, which prevented him from building the very systems that would free him. As a result, more hires led to more dependency, not less. Founders often misdiagnose the problem as "needing better people," when the real constraint is a lack of documented processes and clear direction. Without those, even great hires require heavy management. Scaling isn't about adding people. It's about reducing decision-making friction through structure. Without that, every new hire increases the founder's workload. The Alternative Model: Control vs. Dependency After shutting down his first agency, Chris rebuilt with a completely different model. This time it was lean, contractor-based, and highly controlled. This allowed him to maintain quality and ensure clients received the level of service he expected. The upside is clear: consistency, control, and alignment with his vision. There's no dilution of standards, no miscommunication layers, and no dependency on internal managers. For a founder who values craftsmanship and direct client impact, this model works. But the trade-off is equally clear. The business is entirely dependent on him. If Chris steps away, everything stops. Growth is capped by his capacity, and the business cannot function independently. This is the other side of the spectrum: instead of chaos from too many people, it's constraint from too much centralization. Both models reveal the same underlying truth: the founder's role has not evolved. The System Gap: What the Navy Got Right Looking back, Chris wishes he had implemented some of his Navy experience into his management. For instance, the military operates on clear objectives, defined processes, and structured decision-making. In that environment, the objective is explicit. Everyone understands the goal, the constraints, and their role in achieving it. Teams are encouraged to think and propose solutions, but within a defined framework. That balance creates both autonomy and alignment. Chris recognizes that he failed to bring this structure into his agency. Without clear objectives and documented processes, his team couldn't operate independently. Every deviation required his intervention. This highlights a critical shift: leadership is not about doing the work or even managing people, it's about designing systems that enable others to execute without constant oversight. The Future of Advertising: Precision, Data, and AI Chris also shares how his current agency is evolving alongside major shifts in advertising. Geofencing allows businesses to target users based on physical location, creating highly specific audience segments. Combined with connected TV (CTV), this enables precise ad delivery across devices, including household televisions. Traditional mass advertising is being replaced by targeted, data-driven distribution. Agencies that understand how to leverage this can deliver stronger results with lower spend, increasing their value to clients. Also layered on top of this is AI, which Chris used across the entire workflow, from creative development to campaign strategy. What once took hours or days can now be executed in minutes, often with better output. But while these tools increase efficiency, they don't solve the core structural problem. AI can enhance execution, but it doesn't replace the need for systems, positioning, or leadership evolution. The Real Constraint: Founder Dependency Across both versions of Chris's business, the 22-person team and the lean solo model, the same constraint appears: the business relies entirely on the founder. Whether that dependency comes from poor structure or intentional control, the outcome is the same: the business cannot grow or operate without the founder. This is the core challenge most agency owners face. It's not hiring, lead generation, or even service delivery. It's the inability to transition from operator to architect. Until that shift happens, every model, large team or solo, remains limited. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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Why Your Agency Can't Scale Until You Stop Being the Doer with Matt Kovacs | Ep #893
2026/04/01
  Have you ever wondered how to strike that balance between managing your team and ensuring success for your clients? Today's featured guest is here to talk about what it actually takes to evolve from doing the work to building a team that can win without you. The conversation cuts through common agency myths, like hiring better clients first or relying on RFPs, and instead exposes the real drivers of growth: team strength, leadership evolution, and structural leverage. Matt Kovacs is the president of Blaze PR, a boutique agency for lifestyle brands hungry for a piece of the market share. Kovacs brings a grounded, operator-to-leader perspective shaped by years of building and scaling a lifestyle PR agency across industries like CPG, restaurants, and real estate. His focus is on people, systems, and the subtle shifts that move an agency from founder-reliant to team-driven. In this episode, we'll discuss: Which comes first, better clients or a better team? The founder evolution from doer to developer of people How Matt's team is integrating AI Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. The Real Constraint: Founder-Centric Teams Most founders believe their growth problem is external, more leads, bigger clients, better positioning. But the real constraint is internal: everything still runs through them. Matt describes the shift from doing everything to stepping back into leadership. In the early years, he was deeply embedded in delivery, client work, and execution. That's normal. But the shift could only happen once he changed his willingness to let go. The turning point came when the agency had enough team strength and client quality to create space. That space allowed him to focus on mentoring, business development, and strategic oversight instead of execution. This is where most founders stall. They try to grow while staying embedded in delivery. The result is bottlenecks everywhere. Sales slows down. Team development stagnates. Clients remain dependent on the founder. When this happens, growth doesn't break the bottleneck. It amplifies it. The Misdiagnosis: "We Need Better Clients" What should come first, better clients or a better team? A common belief among agency owners is that landing bigger clients will solve their problems. Kovacs challenges that directly: better clients come after a better team, not before. Without a strong team, bigger clients actually make things worse. They increase pressure, expose gaps, and force the founder to stay involved at an even deeper level. Instead of elevating the agency, they trap it. This is why agencies experience the "rollercoaster": win a big client, scramble to deliver, neglect everything else, then lose momentum. The sequence is wrong. It should be Stronger team → better client experience → higher-quality clients. Not the other way around. And that shift requires a founder to stop thinking like an operator and start building like an architect. The Hidden Cost of Not Evolving If you stay stuck in delivery, your team never fully develops, clients remain tied to you, and eventually, growth slows. This is where many agencies plateau between $1M–$3M. They have revenue, but no real structure. They're busy, but not scalable. And the founder becomes the most expensive, and least scalable, resource in the business. The Structural Shift: From Doer to Developer of People Kovacs' approach to leadership is focused on understanding people. For him, managing a team isn't one-size-fits-all. Some team members need daily interaction. Others need autonomy. Some respond to recognition. Others to responsibility. This level of awareness is what separates managers from leaders. But the deeper shift is this: the founder's job becomes developing people, not producing work. For instance, he recently stepped back during a major pitch and allowed a junior team member to lead a critical part of it. She had developed deep expertise through personal interest, and instead of controlling the outcome, he created space for her to step up. They won the account, but more importantly, this gesture strengthened the entire organization. When founders hold onto control, they limit the ceiling of their team. When they create opportunities for others to lead, they expand capacity, without adding headcount. The New Environment: AI Won't Save You Matt explains how his team is integrating AI carefully, with guardrails, reviews, and intentional usage. It's a tool to enhance output, not replace thinking. He understands that AI amplifies whatever system already exists. If your agency is chaotic, AI makes it faster chaos. If your agency is structured, AI becomes a force multiplier. This is why some agencies will compress timelines, increase margins, and outpace competitors, while others fall further behind. The difference isn't the tool. It's the operating model behind it. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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Why Doing More Is Holding Your Agency Back (And What to Do Instead) with Darby Copenhaver | Ep #892
2026/03/29
In today's rapidly evolving agency landscape, uncertainty has become the norm rather than the exception. From the overwhelming rise of AI to the paralysis that comes with too many decisions, agency owners are struggling to determine how to move forward with clarity. To stay competitive, founders must learn to adapt to constant change, identify true bottlenecks, evolve their roles, and simplify their systems to scale effectively. What You'll Learn ----------------- - Getting by in the age of uncertainty   - Why revenue isn't the only metric that matters   - How growth requires transforming your role—not just scaling your business  Key Takeaways ------------- The agency world isn't slowing down—and neither should you. Moving forward means doing the right things, at the right time, in the right role. Progress, not perfection, is what drives real growth. In this rapidly evolving agency landscape, uncertainty has become the norm rather than the exception. From overwhelming decision paralysis caused by AI and doubts on how to move forward with clarity, owners need to adapt to constant change, identifying true bottlenecks, evolving their role, and simplifying systems to scale effectively. Today's featured guest is the first point of contact for agency founders experiencing these very struggles. As someone very in tune with the issues founders face, he'll talk about the steps they need to take to prevent becoming a bottleneck that gets in the way of their own growth and share why growth isn't about doing more; it's about becoming something different. Darby Copenhaver serves as our Agency Scale Specialist, working closely with agency founders to help them identify where they are in their growth journey and which steps they need to take next. As the first point of contact for many agencies entering Jason Swenk's ecosystem, Darby plays a critical role in diagnosing challenges, building scaling strategies, and guiding founders through the complexities of growth. His day-to-day conversations with agency owners give Darby a unique vantage point into the current state of the industry, what's working, what's not, and where most founders get stuck. In this episode, we'll discuss: Getting by in the age of uncertainty Stop chasing revenue as the only metric that matters Growth isn't just about scaling, it requires transforming your role Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. Herringbone Digital: If you're thinking about exiting now, planning a few years ahead, or just want to understand your options, you should know about Herringbone Digital. They're not a typical financial buyer—they're operators who actually understand what it takes to build and herringbonedigital.com/swenk scale an agency because they've done it themselves. Their approach is simple: invest in great founders, protect what's already working, and help agencies scale faster. Go to herringbonedigital.com/swenk and start the conversation. The Age of Uncertainty (and Why It's Not All Bad) Agency owners today are operating in an environment that's changing faster than ever. From shifting client expectations to the explosion of AI tools, the pace of change is creating a unique kind of pressure: not fear of failure, but fear of making the wrong move. As Darby points out, most founders aren't worried about losing their business; they're worried about falling behind or investing in something that becomes obsolete in months. This uncertainty often leads to indecision. Founders remain frozen, like a deer in headlights, and in business, standing still is often the riskiest move of all. Agencies that hesitate too long risk getting overtaken by competitors who are willing to experiment, adapt, and move forward despite imperfect information. The lesson for founders is that you don't need perfect clarity. You need momentum. Making decisions, testing, and iterating will always outperform waiting for certainty that never comes. The Hidden Weight of Growth As agencies grow, so does the burden of responsibility. What starts as excitement and curiosity can quickly turn into fear and pressure. Founders begin to worry about losing clients, disappointing teams, or making decisions that could jeopardize everything they've built. It's possible to scale without losing that sense of curiosity and excitement. The difference lies in mindset. Founders who continue to operate with a "startup mentality" remain agile, open, and willing to experiment, even at scale. On the flip side, those who become overly cautious often stall their own growth. They begin to overanalyze decisions, leading to slower execution and missed opportunities. Growth shouldn't feel like carrying a heavier burden, it should feel like gaining leverage. Stop Chasing Revenue, Fix the Foundation One of the biggest misconceptions in the agency world is the obsession with hitting revenue milestones, especially the coveted "seven figures." While reaching $1M is often celebrated, Jason and Darby agree revenue alone is a poor indicator of success. If an agency hits $1M but the founder is still doing everything (sales, delivery, operations) it's not a win. It's a trap. Growth without the right foundation only amplifies existing problems, leading to burnout and instability. Instead, founders should focus on metrics that actually matter: profitability, time freedom, and operational efficiency. When those are in place, revenue growth becomes a natural byproduct. Building a scalable agency isn't about stacking more clients but about building systems that support sustainable growth. Founder Evolution From Operator to Owner It's been a prevalent idea this year but agency owners should understand that growth isn't just about scaling the business. It's about transforming yourself as a leader. Darby explains that this is less about "growth" and more about "evolution," where each stage requires you to become something fundamentally different. This progression can be outlined as follows: Operator – You do everything. Manager – You delegate tasks but still make all decisions. Architect – You build systems and empower others to decide. CEO – You set vision, coach leaders, and represent the brand. Owner – The business runs without you. Many founders get stuck in the operator or manager stage because they don't know what the next level looks like. Without that clarity, they default to guesswork, making changes that don't move the needle. The breakthrough comes from understanding your current role and intentionally evolving into the next. This requires letting go of old responsibilities and stepping into new ones, even when it feels uncomfortable. AI Is a Tool, Not a Strategy AI is one of the biggest sources of both excitement and overwhelm for agencies right now. While many teams are experimenting with tools like custom GPTs, most are only scratching the surface, using AI for basic tasks like brainstorming or content generation. The real opportunity lies in going deeper. AI should enhance your capabilities, not replace them. Agencies that use AI strategically can create "superpowers" for their teams by automating repetitive tasks, improving efficiency, and freeing up time for high-impact work. However, there's also a growing issue of AI fatigue. With new tools emerging constantly, it's easy to feel overwhelmed and unsure where to focus. The solution isn't to chase every new tool but to build a solid foundation for how AI fits into your workflows and operations. Stop Hiring for Problems You Don't Understand A common mistake agency founders make is trying to "solve everything" by hiring a senior leader—like a Director of Operations or COO—too early. While it might seem like the logical next step, it often leads to frustration and wasted resources. The problem is simple: you can't hire someone to solve problems you don't fully understand. Without clear systems, processes, and direction, even the most experienced hire will struggle to make an impact. Instead, start smaller. Audit your time, identify low-value tasks, and begin delegating those first. Freeing up your time allows you to focus on higher-level thinking, eventually leading to the clarity needed to make smarter hires.
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AI Is Reshaping Agencies. Staying Average Will Kill Yours with Brian Hansen | Ep #891
2026/03/25
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Artificial intelligence is rapidly changing how agencies operate. But the real shift isn't just about tools. It's about structure, mindset, and leadership. Today's featured guest has taken the time to explore how agencies are adapting to AI, why many agencies will struggle to survive the shift, and how founders must evolve alongside the technology. From building AI-native workflows to maintaining authentic brand connections in an automated world, the conversation highlights a central theme: agencies that stay curious and adaptable will win. Those that cling to "the way we've always done it" won't. Brian Hansen is the founder of Rocket Pilots, a marketing agency focused exclusively on helping law firms grow their revenue through targeted marketing strategies. Unlike generalist agencies, Rocket Pilots operates within a single vertical, allowing the team to develop deep industry expertise and deliver highly specialized services. In this episode, we'll discuss: Why it's a good idea to be fully AI-native. The cultural shift your agency should be making. Why average agencies will struggle the most with the rise of AI. Why the future belongs to curious founders. Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. Starting Out Without a Niche in Mind Brian didn't start his agency with a legal niche in mind. In fact, he openly admits he ended up finding his current niche by doing it 'the hard way'. Early on, his agency worked with multiple industries and offered a wide range of services. But over time, he realized that focusing on what the agency did best, and who they served best, produced better results for both clients and the agency itself. That insight led to a clear decision: narrow the offering, specialize in the legal space, and deliver exceptional outcomes. Today, he is focused on the next evolution of agency operations: building an AI-native agency environment that allows teams to work faster, smarter, and more efficiently. Why Agencies Must Become "AI Native" Right now, Brian is focused on his agency becoming fully AI native, which goes far beyond occasionally using ChatGPT or experimenting with AI tools. Instead, becoming AI native means designing your agency's internal systems and workflows so that AI can effectively operate within them. This includes something as foundational as how documents are stored and organized. If agencies want to use custom AI models or assistants to help with strategy, writing, research, and execution, those systems need structured data and clear documentation. Without that foundation, AI cannot function as a true multiplier. Because of this, Brian's team is currently restructuring their internal systems from file organization to documentation so AI tools can access the context needed to support their work. When done properly, AI doesn't just speed up tasks; it becomes an operational layer that enhances every role in the company. In other words, agencies shouldn't simply "use AI." They should build their operations around it. The Cultural Shift Agencies Need to Make Technology alone won't determine which agencies succeed in the AI era. Culture will. Founders are often the first people inside an agency to explore new technologies. They test tools, build systems, and experiment with new capabilities long before the rest of the team adopts them. But that dynamic can create a dangerous knowledge gap if the rest of the organization doesn't follow. Brian believes agencies must actively create a culture where employees are encouraged and even required to experiment with AI tools and share what they learn. Teams should be discussing new workflows, sharing AI "wins," and constantly asking how the technology can improve their work. Employees who treat AI as a partner, rather than a threat, will become dramatically more valuable inside modern agencies. Instead of replacing talent, AI often amplifies it by allowing team members to operate like high-level project managers directing intelligent systems. Agencies that embrace this cultural shift will gain a major competitive advantage. Why Average Agencies Will Struggle At the start of the internet era, traditional agencies that dismissed how this new development would change agencies forever were the ones to set themselves up for failure and many of them disappeared within a few years. Likewise, the agencies most at risk in the coming years are the ones stuck in the middle. They aren't exceptional specialists. They aren't deeply innovative. And they rely on the same processes they've used for years. History has shown what happens to businesses that ignore major technological shifts and Jason believes AI represents a similar moment. Agencies that remain average, offering undifferentiated services without leveraging new technology, will find themselves squeezed by faster, more efficient competitors. At the same time, the agencies that thrive will be those that use AI to enhance strategy, creativity, and efficiency rather than simply automate low-level tasks. The future won't belong to agencies that resist change. It will belong to those that adapt faster than the market expects. Authentic Branding Still Matters in an AI World Despite the rise of automation, and maybe even because of it, authentic human connection remains essential and is becoming even more valuable. As AI-generated content becomes more common, audiences are becoming increasingly skilled at recognizing it. Automated comments, generic posts, and AI-generated personas rarely create real engagement or trust. That's why personal branding and authentic communication will continue to matter. Agencies that build real relationships with their audience through thoughtful content, real insights, and genuine expertise will stand out in a crowded digital environment. While AI can accelerate content production, it cannot replace credibility, experience, or trust. Those elements must still come from real people. The Role Evolution Every Agency Founder Must Make Beyond technology, Jason has seen that agency growth ultimately depends on the evolution of the founder's role. Most agency founders begin by doing everything themselves. They sell, deliver work, manage clients, and handle operations. Over time, they may become managers overseeing teams. But long-term agency growth requires another transition from manager to architect and CEO. At that level, the founder is no longer executing daily work. Instead, they design the systems, structure, and strategy that allow the organization to scale independently. Eventually, the ultimate goal is reaching the role of true owner, where the agency can operate successfully without constant founder involvement. AI tools can accelerate this evolution by automating operational complexity, but the mindset shift still has to come from the founder. Technology alone doesn't create scale. Leadership does. The Future Belongs to Curious Founders If there's one trait that will define successful agency leaders in the coming decade, it's curiosity. The AI landscape changes almost weekly. New tools, new capabilities, and new opportunities appear constantly. Founders who stay curious, experimenting, testing, and learning, will continue to find ways to adapt. Those who assume they already know enough will fall behind. For agency owners, the challenge isn't simply adopting AI tools. It's building organizations that evolve alongside the technology. The agencies that do that won't just survive the AI era. They'll lead it. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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Why Agencies Lose Clients: Confusing Reports and Outdated Operating Models with Nate Jenson | Ep #890
2026/03/22
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Do you assume a very complicated report will guarantee clients appreciate all the work you're putting into generating leads for their business? It may end up having the opposite effect. Many agency founders assume their biggest challenge is generating leads or improving campaign performance. However, a deeper issue becomes clear in today's conversation: most agencies end up losing clients due to unclear values and outdated operating models. Our featured guest will unpack how agencies and financial service firms face strikingly similar structural problems. From vague service promises to bloated processes and inefficient teams, both industries are being forced to evolve, especially as automation and AI raise expectations around speed, clarity, and decision-making. Nathan Jenson is a former agency owner, current CFO of Badass Bookkeeping, and CEO of askQuick.ai, a service that connects with QuickBooks to show you what's really going on in your business. He's made it his mission to connect business owners to their numbers so they can make smarter decisions. Nathan has appeared on the podcast before, and since his last visit, he rebuilt his business model using a very different philosophy, one centered around automation, operational simplicity, and minimizing dependency on large teams. Having sold a previous company that relied heavily on people and manual processes, he focused on building a scalable financial services business that runs on systems, not headcount. His experience working closely with agency owners gives him a unique perspective on where agencies get stuck and why many founders unknowingly create the very bottlenecks holding their companies back. In this episode, we'll discuss: Are you earning clients' trust? How complex reports just confuse clients How automation is reshaping expectations Why headcount is not a measure of success Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. Herringbone Digital: If you're thinking about exiting now, planning a few years ahead, or just want to understand your options, you should know about Herringbone Digital. They're not a typical financial buyer. They're operators who actually understand what it takes to build and scale an agency because they've done it themselves. Their approach is simple: invest in great founders, protect what's already working, and help agencies scale faster. Go to https://www.herringbonedigital.com/swenk and start the conversation. Why Clients Lose Trust in Agencies Many agencies assume clients judge them primarily on campaign performance, but the reality is more nuanced. Often, clients cannot tell whether the agency is succeeding or failing because it fails to clearly communicate what success should look like in the first place. In his experience as a client, despite spending significant money on paid advertising, social campaigns, and LinkedIn outreach over several years, Nate found he was getting almost no meaningful leads. As a client, the experience felt like throwing money into a black box. When this is the case, the disconnect typically originates from one of two traps: Agencies fail to deliver meaningful results Or they fail to communicate the results they did deliver In both cases, the outcome is identical: clients feel uncertain about the value they are receiving. This communication gap becomes even more dangerous in an era where AI tools can produce reports, insights, and dashboards instantly. If agencies continue delivering confusing reports full of jargon or technical metrics, clients will increasingly turn to tools that can interpret their data more clearly. Simply put: clarity is now a competitive advantage. Are You Proving Your Expertise or Just Confusing Clients? Nate has stories from practicing in accounting agencies that perfectly mirror what happens in marketing agencies. A business owner once hired him to replace a fractional CFO who had been sending him financial reports packed with complicated spreadsheets, amortization schedules, and technical accounting data. The problem wasn't that the reports were wrong. The client just had no idea what any of it meant. From the client's perspective, the reports were useless. This behavior exists across many professional services industries. Experts often overcomplicate reporting to demonstrate expertise, but this usually has the opposite effect. When a client receives pages of technical information they cannot interpret, they assume one of two things: Either the service provider is hiding something. Or the service provider doesn't understand the client's real priorities. What clients actually want is simple: Are we improving? Are we losing money somewhere? What should we do next? If agencies cannot answer those questions clearly, they risk looking indistinguishable from competitors who truly underperform. Automation Is Reshaping Operational Expectations Nate rebuilt his current company around one principle: automate everything that doesn't require human judgment. In accounting, that means allowing software to categorize transactions, generate reports, and monitor financial performance automatically. Tools like QuickBooks already provide rule-based automation that eliminates much of the manual work bookkeepers traditionally perform. By implementing these systems, Nate reduced massive amounts of operational labor. For example, many of his financial analyses once required one to two hours of preparation per client each month. Now, automated systems can generate those reports instantly, allowing him to spend his time interpreting insights rather than compiling data. This shift mirrors what is happening inside agencies. Marketing platforms, analytics tools, and AI assistants increasingly handle tasks that once required teams of specialists. Campaign reporting, performance insights, and forecasting can now be generated in seconds. This means that the agencies with the biggest advantage will be the ones with the best systems, not with the biggest team, as it used to be. In fact, automation allows firms to grow without proportional increases in staffing, which dramatically improves profitability and scalability. Why Headcount Is a Dangerous Measure of Success Like many founders, Nate used to think that growth meant hiring more people and building a larger organization. Eventually, his company reached around ten employees, and the reality of management set in. Instead of freedom, he experienced something different: constant oversight, quality control issues, and the stress of managing people who struggled to perform consistently. Some employees were exceptional and could operate independently. Others required constant supervision. The experience revealed a harsh truth about scaling service businesses: more employees do not automatically mean more leverage. In fact, hiring the wrong people often creates new bottlenecks for the founder. When founders must constantly review work, answer questions, and correct mistakes, they become even more central to the business than before. That realization pushed Nate to design his new company focusing first on systems and automation before expanding the team. The Evolution of the Founder's Role When it comes to owners who end up reviewing everyone's work and involved in every decision, we all know this happens too much in the industry. This is basically a failure in evolving the founder's role as the agencies grow: Operator – Doing everything yourself Manager – Hiring and supervising people Architect – Designing systems, processes, and structure CEO – Leading strategy and company direction Owner – The business runs independently True scalability begins when founders transition into the architect role, designing systems that allow the company to operate consistently without their constant involvement. The Structural Next Step for Agency Founders The agencies that struggle over the next few years won't fail because of marketing tactics. They'll fail because their operating models never evolved. Clients expect clearer outcomes. AI is compressing timelines for analysis and reporting. Automation is reducing the need for manual work. The founders who win will be the ones who stop trying to scale effort and start designing leverage. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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What Do Private Equity Firms Look for When Buying an Agency? With Ben Gaddis | Ep #889
2026/03/18
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Most agency owners say they want to sell someday… but they're building something completely unsellable. The mistake? Not only a lack of a clear vision for the future of their agency, but also a lack of understanding of what they'll need to build a sellable agency. If you're an agency owner planning to sell one day, do you understand what buyers are usually looking for? Do you know which type of buyer you're hoping to attract? Today's featured guest understands that most agencies are acquired by private equity and built the private equity partner he felt was missing in the space. He'll talk about what actually drives valuation, what kills deals, and how to build an agency that buyers want to compete for. Ben Gaddis is the former founder of T3, a digital agency he sold to private equity in 2019. After going through multiple acquisitions himself, he now runs an operator-led private equity firm focused exclusively on tech-enabled service and agency businesses. As a former owner who's been on both sides of the table, he knows exactly what buyers are thinking. In this episode, we'll discuss: What are private equity companies looking for in agencies? Recurring revenue vs. retention What would actually increase your agency's valuation? If the goal is talent, should you consider an acquisition? Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. What Private Equity Actually Looks For (It's Not What You Think) The reality is that most private equity companies are looking to buy a couple of agencies to slam them together and eventually sell them for more. Based on this, agency owners have an idea of what these buyers want and mostly focus on revenue or EBITDA. According to Ben, however, buyers are looking at a few core things first: Client concentration Recurring or predictable revenue Net revenue retention Founder dependency (aka key-person risk) Clear vision and differentiation Let's start with client concentration. A lot of owners panic if one client makes up 20% of revenue. Some PE firms get nervous at 10%. But Ben brings nuance here. If you've landed and retained a $2–3M client for years, that's proof you can serve at a high level. That's powerful. The issue isn't just one big client. It's when your top 3–5 clients make up 50–60% of revenue. That's where it gets risky. If you're in that position, you already feel it. One bad email. One procurement shift. One budget freeze. And your stomach drops. That's not a valuation problem. That's a freedom problem. Recurring Revenue vs. Retention (The Smarter Metric) Everyone argues about contracts. "Should I lock clients into 12 months?" "Should we go month-to-month?" Ben argues that the real metric is net revenue retention. If you're at 90–100%+ retention, buyers don't care as much about contract length. He shared a case where they bought a company with almost zero recurring revenue but 115% net revenue retention. Clients kept buying more. The business was healthy. The packaging just needed to change. This is huge for agencies stuck in custom project hell. Sometimes it's not your service. It's how you position and sell it. Are you framing projects as standalone deliverables or as phases in a longer journey? If you're stuck working in the business and scrambling for the next sale, this is where to look first. Integration > Financial Engineering There are two types of buyers: Financial engineers smashing agencies together to increase multiples Operator-led firms building real integrated offerings Ben sees a lot of "fake integration." Agencies get acquired, but nothing truly connects. No shared systems. No real cross-sell. No operational synergy. Sophisticated buyers see through that immediately. What actually increases valuation? Additive capability. Does one service naturally lead to another? Does it solve a deeper problem for the same buyer? Does it expand wallet share within the same account? If you're thinking about acquisitions, don't buy revenue. Buy strategic fit. Otherwise, you're just running two companies under one logo. Growing Through Acquisition (And When Not To) A lot of 7-figure agency owners hit a wall where they can't hire fast enough and start to feel overwhelmed. The team depends on them. Growth feels capped. So they think: "Maybe I should acquire" and figure they should start small, as it seems easier than going through a big acquisition. Buying a bigger company or doing a merger of equals is certainly complicated in terms of defining who's in charge and which brand should remain. So, it should be a very complementary offer with a clear leader for it to make sense. This would be much clearer when buying a smaller business. However, here's the thing: Small acquisitions are just as hard as big ones. The legal, the integration, the emotional complexity, it's all real. If you've never done one before, the odds of it going smoothly are low. If the goal is talent… why not build offshore first? With AI and real-time translation tools, the global talent pool is radically more accessible than it was even five years ago. A lot of agency owners avoid offshore because it failed before. But the game has changed. If your bottleneck is hiring, you might not need to buy an agency. You might need to rethink your talent strategy. How to Prepare for a Sale (Even If You're Not Selling) This is where most deals fall apart, and Ben believes it's important for owners to try to cover any gaps in knowledge. Try to learn as much as you can about the process and the buyer to better understand their expectations. And if you still have questions, then don't hesitate to ask! Some aspects that owners may not understand and that you should start learning about: Working capital expectations Accrual vs. cash accounting Quality of Earnings (QofE) reviews Data cleanliness Revenue tagging Furthermore, Ben recommends something most owners never do: Run your own QofE before going to market. Know your skeletons. Track secured revenue. At the start of each year, how much revenue is already locked in? If that number consistently grows year over year, that's powerful. Buyers will ask about revenue by capability, revenue by sales rep, revenue by region, and client concentration by top 3/5/10. If your data is messy, you lose leverage. And if you're thinking, "I'll figure that out when I'm ready to sell," you're already behind. Vision Is the Real Multiplier Right now, Ben is seeing a lack of vision + execution alignment. AI is reshaping agency models in real time. Entire categories of services didn't exist a few months ago. The agencies that win won't just be efficient. They'll have a tight, clear, communicated vision. Agencies won't scale just because of a tactic. They'll scale because the vision was clear enough that the team could make decisions without the owner. If your team can't make decisions without you, that's not a people problem. That's a vision problem. And that's also why you're still stuck in fulfillment. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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Burned Out Agency Owner to AI Architect: The Real Shift Founders Must Make With Austin Armstrong | Ep #888
2026/03/15
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training How are you protecting yourself from the real risk of owner burnout? Agency owners often burn out because they built a business that depends entirely on them. Today's featured guest is a former agency owner turned AI SaaS founder. He'll unpack what really caused his agency collapse, what he learned from it, and how he rebuilt from a completely different role. Austin Armstrong is the owner of Syllaby, a tool for social media marketing that helps users create their very own realistic digital clone to personalize their marketing efforts, allowing them to forge a deeper connection with their audience. Austin spent over a decade in the agency world, working his way up from intern to running an agency before launching his own. For a while, it worked, until the cracks appeared. His agency was built around organic marketing and heavily centered on his personal brand. High months meant hiring fast. Low months meant wondering if payroll would clear. When a few large clients (that accounted for about 60% of monthly revenue) churned, the instability became unbearable. So Austin made his tech pivot and moved to starting Syllaby, which also came with a role pivot. More recently, he just released his first book Virality and is the co-founder of the upcoming AI marketing World conference. In this episode, we'll discuss: From agency failure to early AI adopter Why the founder bottleneck is emotional The founder evolution model AI exposes weaknesses Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. Making the Decision to Be an Early Adopter When he started Syllaby, Austin could already see the writing on the wall with AI. He was already not happy navigating the agency world, so the question was, "Do I want to place a bet as an early adopter of this technology? Potentially cannibalizing my own agency?" He spoke with several clients and business owners and came to the conclusion that most people hire an agency because they know they need to create content to be relevant, but didn't know how to pick the right topics, and in many cases didn't want to be on camera. They needed help staying consistent and accountable. Some of them don't even have the money to hire an agency, but still have a message and an expertise to share. So Austin started to look for ways to automate those processes using AI. The Founder Bottleneck Is Emotional Before It's Operational The emotional weight of the unraveling of Austin's agency was real. Nightmares about client complaints. Constant vigilance. Inability to disconnect. Eventually, he decided to make a bet on AI and launched Syllaby, an AI-powered content platform designed to automate much of what agencies manually execute, from topic discovery to scripting to publishing. Now, looking back, he sees his agency's failure came from several mistakes. It wasn't bad marketing or lack of demand. It was structural dependency. The agency relied on: His personal brand His client relationships His decision-making His emotional capacity When large clients churned, revenue collapsed because concentration risk hadn't been designed out of the model. When delivery required nuance, he couldn't step away because "he stirred the pot." This is the Operator trap. The Founder Evolution Model Most founders believe they own an agency. In reality, the agency owns them. What is supposed to happen as your agency evolves is that your role in it evolves as follows: Operator → Manager → Architect → CEO → Owner At the Operator level: Sales depends on you. Delivery depends on you. Escalations go to you. Pricing goes through you. And when you focus on one area, another suffers. Systems Create Freedom But They Also Create Identity Shifts As the owner, being needed feels good and letting go feels disorienting. Austin acknowledged this tension. In his agency, clients wanted him. Even with SOPs, some work required nuance. Some of it was ego. Some of it was positioning. Some of it was hiring the wrong people in the wrong seats. Having learned his lesson, things look very different in his SaaS company, where he can rely on strong partners, defined ownership, AI-supported workflows, and clear decision rights. Now he can disappear for two weeks, go skiing with family, speak at events, and the business doesn't break. AI Exposes Weakness All over the industry owners agree that AI isn't replacing strong agencies. It's exposing weak ones. At Syllaby, Austin has integrated AI so much is hard to think where he DOESN'T use it. He automates what many agencies sell manually: SEO-based topic discovery Script generation Video creation Scheduling and publishing For smaller businesses, this lowers the barrier to entry. For agencies, it creates leverage. Which tool are owners using? This varies from time to time. What you should be doing is testing them all out to see which ones work better for you, as well as creating a brief with all the information you'll need in case you decide to migrate to a different tool. Jason calls this his "AI Operating Brief", a master document loaded with: Company positioning Customer data Success stories CRM insights Transcripts Strategic principles Once embedded into AI tools, it eliminates repetitive context-setting and removes founder bottlenecks. Austin does something similar with what he calls his "Austin Codex", years of content, frameworks, and intellectual property housed inside AI models. The result is institutional memory without constant founder involvement. Time Audits Reveal the Hidden Ceiling Austin is a big fan of the full-time audit exercise: For one to two weeks, document: Every task Start and end times Whether it's mandatory or optional Your enjoyment level The dollar value of your time The outcome is uncomfortable. Once you're done, you'll see which $10 tasks eating $1,000/hour time, the emotional drain disguised as "important work", and the distractions masquerading as urgency. He outsourced email management, calendar coordination, travel booking — all consolidated into a daily executive summary delivered where he actually spends time. Not because he can't do it, but because he shouldn't. The bigger lesson: you don't scale an agency… you outgrow your role. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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Why Project-Based Agencies Feel Profitable But Aren't Sustainable with Michael Boychuk | Ep #887
2026/03/11
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you winning exciting projects but still feeling exhausted at the end of every quarter? Does your agency look successful from the outside, yet feel fragile or chaotic behind the scenes? For most agency owners, the real struggle isn't creativity. It's sustainability. The real challenge begins after the win, when you have to deliver consistently, protect your margins, manage your team, and somehow still have the energy to lead. Michael Boychuk is the founder and creative director of DNA&Stone, a creative agency that deals in real emotion and embrace the hard truth, understanding that brands that connect emotionally see 50% higher revenue growth. He'll talk about scaling creatively led agencies, navigating mergers, embracing productive conflict, and integrating AI without sacrificing emotional storytelling. In this episode, we'll discuss: Why creative isn't enough The merger process Embracing tension & clear swim lanes in partnerships Set audacious goals or stay average Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. Leaving Amazon to Start a Creative Agency Michael's career began in small, strategy-led creative shops before moving to Leo Burnett in Chicago. Eventually, he crossed to the client side as Global Executive Creative Director at Amazon, working closely on major brand initiatives. While many creatives were moving in-house at the time, Michael saw the gap in how external agencies worked with internal creative teams. Even the most respected agencies struggled to collaborate effectively with in-house counterparts. So he made the decision to leave Amazon to start his own agency. He co-founded Little Hands of Stone (later merging to become DNA&Stone), building a nimble, creatively driven agency with operational discipline at its core. The goal wasn't to be another agency in a crowded market. It was to build one that worked differently. The Project Roller Coaster: Why Great Creative Isn't Enough In the early years, Michael and his partner excelled at landing high-impact project work. The agency would scale up quickly, execute powerful campaigns, and then scale back down. The upside: Strong margins. The downside: Revenue volatility. Some months were record-breaking. Others were terrifying. This feast-or-famine model made it difficult to invest in long-term infrastructure, particularly account management and relationship-building functions that sustain retainer revenue. As Michael put it, scaling into projects and rapidly reducing afterward may be profitable, but it's not easily sustainable. That realization set the stage for a major shift. The Merger: Combining Creative Firepower with Account Stability After years of competing against DNA, Michael's firm began merger conversations. His six-year-old, creatively led shop was volatile but high-impact. DNA, a 26-year-old agency, had stable retainer revenue and strong account leadership. They were opposites and that made them perfect. The nine-month merger process was far more complex than expected. Michael describes it as "drawing up a marriage certificate." But strategically, it functioned like a time machine, instantly solving growth limitations both firms faced independently. However, merging on paper is easy. Operationalizing it while "building the plane during barrel rolls" is the real challenge. One year later, they're still refining the model and balancing creative ambition with financial discipline. Account Management vs. Creative Leadership One of the biggest lessons Michael learned post-merger is the value of strong account leadership. Creative leaders tend to chase the next exciting idea. Account leaders think in terms of long-term relationships, financial discipline, and sustainable growth. You need both. Rather than avoid tension, the four partners embrace it. Michael believes healthy conflict is essential. If there's no disagreement, you're probably not addressing the real issues. But the key is respectful conflict rooted in trust. They operate with: Clear swim lanes (each partner has decision authority in their domain) Open debate before decisions 100% alignment after decisions are made No back-channel dissent or lingering resentment. Only unified execution. Embrace the AI Wave But Protect the Emotion Michael doesn't sugarcoat his views on AI. If agencies aren't actively integrating AI into workflows and developing proprietary approaches, they risk irrelevance. But he also warns against overcorrection. Yes, AI improves efficiency and enhances pre-visualization and brainstorming. Yes, it can increase margins. But creative agencies aren't data-processing factories. They're emotional engines. In his view, the industry is currently drowning in data while starving for emotional resonance. AI can create competent output but it often carries a detectable "stink," a subtle lack of human nuance. He chooses to use AI to: enable better creative. improve efficiency. remove bottlenecks. However, it should not be used to replace emotional storytelling. Because humans still crave human connection and no algorithm can replicate lived experience. Set Audacious Goals or Stay Average The biggest lesson Michael took from his time at Amazon working directly with Jeff Bezos was to set ambitious goals. After campaigning to have an Amazon ad during the Super Bowl, he got Jeff's attention and set out to create a top-five Super Bowl ad. But during development, director Wayne McClammy challenged him: "Why aim for top five? Why not number one?" That shift in ambition changed everything. Every decision became filtered through one question: Is this the move that gets us to #1? The resulting product was the "Alexa Loses Her Voice" Super Bowl spot featuring Cardi B and Anthony Hopkins. And, yes, it was ranked the number one Super Bowl ad that year. The lesson for him was about standards. If your goals don't make you nervous, they're not big enough. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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How Forward-Thinking Agencies Win with SEO, GEO, & LLMs with Terry Zelen | Ep #886
2026/03/08
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training AI is either the end of agencies… or the biggest opportunity we've had since the internet. Most agree it's the second one. Agencies that are winning right now are combining SEO, GEO, AEO, and LLM optimization so they show up everywhere decisions are being made. They're using AI to increase leverage, not replace thinking. And they're restructuring their teams around strategy, insight, and proprietary data instead of repetitive task work. Today's featured guest will discuss why SEO isn't dead (it just grew up), the biggest mistake agencies are making with AI, how to 10x output without adding headcount, and why your unique data is the unfair advantage that separates you from every other agency prompting ChatGPT and hoping for magic. Terry Zelen is the founder of Zelen Communications, a 35-year-old agency that pivoted aggressively into AI over the last three years. He's helping clients win visibility across both search engines and large language models (LLMs) and even building AI tools internally to reduce hallucinations and improve accuracy. Terry has a degree in marine biology, so marketing wasn't the master plan. After college, he tried breaking into the creative world with zero portfolio and got laughed out of the room; until one person gave him a shot. He worked for free, proved himself, connected with a freelance rep, and slowly worked his way up through the agency ranks. He eventually transitioned from freelancer to agency owner by acquiring his own accounts and building relationships locally in Tampa. Fast forward three decades and now he's helping clients navigate AI, LLM visibility, and what modern SEO really looks like. In this episode, we'll discuss: Why SEO is more complicated now, but agencies willing to adapt can still win How LLM visibility will win you business AI: The greatest leverage small businesses have ever had Building an AI consensus engine Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. SEO Is Not Dead. It's Just Way More Complicated There's a lot of noise right now around "SEO is dead" or "zero-click internet." But that's an oversimplification. SEO isn't going away. It's evolving. Today, it's not just SEO. It's: GEO (Generative Engine Optimization) AEO (Answer Engine Optimization) Local SEO EEAT (Experience, Expertise, Authority, Trust) Search intent In other words, visibility is the game. Not just ranking in Google, but showing up in LLMs like ChatGPT, Gemini, and Perplexity. Terry points out that while snippets and AI-generated summaries are increasing, people still want to verify sources. They're not buying a couch because an LLM told them it's the best. They'll still visit sites, compare options, and validate credibility. Backlinks, structured content, schema, quality. It all still matters. What's different is that now you're playing the game with Google and the LLMs. How LLM Visibility Actually Wins Business This isn't theoretical. Terry shared a story of a client who builds modular classroom buildings. A school district searched for "best mobile building producer in Florida" and the client showed up in a snippet. That visibility led directly to a new contract. So you're no longer optimizing just for rankings. You're optimizing to be the referenced authority when AI generates an answer. That means you better have structured content, clear positioning, backlinks, authority signals, and presence on surfaces LLMs scrape (including platforms like Reddit, though that's evolving). The agencies that understand this shift can bolt on new services like AI SEO or GEO and, in some cases, significantly increase revenue. But there's a catch. This space is evolving fast. What works today might not work next quarter. That's why Terry avoids gray-hat tactics and focuses on fundamentals. AI Is the Greatest Leverage Small Agencies Have Ever Had Terry believes this might be the most exciting time ever for small agencies because AI has eliminated barriers that used to require massive budgets. When a small restaurant client wanted a red snapper on a black background for their website, stock photography didn't cut it and real shoot would've required a diver, photographer, cooperative fish and a significant budget. Instead, they used Midjourney to create the image. Then they animated it so the fins and gills subtly moved. The client was blown away. For a small restaurant, this level of visual production used to be impossible. Now it's affordable and scalable. That's the opportunity. Agencies can deliver higher-quality creative, faster, and at lower cost if they know how to use the tools. A Very Real Fear for Future Marketers Terry regularly speaks to marketing students who are worried AI will take their jobs. What he tells them is that AI won't take your job, but someone who knows how to use AI will. The key is not blind reliance. It's intelligent leverage. AI is excellent at: Research Proposal drafting Competitive analysis First drafts of content Summarizing data What used to take weeks can now take hours. That frees your team from repetitive, dreaded tasks and allows them to focus on strategy, creativity, and client impact. But there's a danger in over-reliance. Too many agencies are slapping "AI" on everything without adding original thinking or proprietary data. Your edge isn't that you use AI. Your edge is your data. Every agency has unique client data, performance metrics, positioning, and experience. When you combine that with AI, that's where real leverage happens. Building a Consensus Engine to Reduce AI Hallucinations One of the more advanced things Terry is experimenting with is what he calls a "consensus engine." The problem with LLMs is that they're probabilistic, not deterministic. Ask the same question twice and you'll get two slightly different answers. They also hallucinate. To combat this, Terry built a workflow using N8N (a Zapier-like automation tool) that runs content through multiple LLMs. One writes it. Another critiques it. The final output must pass both systems before it's considered valid. If they disagree, it's sent back through with adjusted parameters. He's also exploring how different LLMs perform best in different roles: Perplexity for real-time research ChatGPT for writing Claude for programming Instead of treating AI as one tool, he's assembling a stack of specialized tools. That mindset shift, thinking like a systems architect instead of a prompt typist, is what separates surface-level AI use from strategic advantage. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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How to Raise Your Agency Prices From $2,500 to $45,000/Month (Without Changing Deliverables) With Eli Rubel | Ep #885
2026/03/04
Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Most agency owners don't fail because they're bad at delivery. They fail because they underprice, overcomplicate, and build businesses that trap them instead of freeing them. Today's featured guest unpacks the type of life he envisioned when he set out to start an agency, it took to scale from charging $2,500 a month to closing $45,000/month retainers, surviving a market collapse, and making the counterintuitive decision to split one agency into two. Eli Rubel is the founder of Matter Made, a B2B SaaS marketing agency, and No Boring Design, a premium design studio serving high-growth tech companies. He entered the agency world in 2019 after burning out on the venture-backed SaaS model, despite a previous exit. What drew him to agencies wasn't prestige or scale; it was a desire to take control over his time, lifestyle, income, and location. Agencies, when built correctly, offered the fastest path to freedom without sacrificing ambition. Over the next few years, Eli scaled MatterMade aggressively, navigated a brutal tech downturn, and rebuilt his business with sharper positioning, stronger pricing, and clearer operational boundaries. In this episode, we discussed: Why hiking prices was the right choice early one How and why he decided to create his second agency The reason that shared services failed fast Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Agencies could be losing 15–30% of their profit every year without seeing it. The usual suspects are time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. That's why Toggl created the Agency Profit Heist, a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. Why Agencies Beat Venture-Backed SaaS (If You Want Freedom) After years in venture-backed SaaS, chasing growth at all costs, Eli was done with a model he realized was grinding him down. The pressure, the lack of control, and the delayed payoff didn't align with what he actually wanted: family, flexibility, and financial independence. Agencies offered speed to cash and autonomy, which SaaS didn't. Instead of swinging for a hypothetical future exit, Eli chose a business model that paid well now and let him design his life intentionally. It was a shift he made with eyes wide open and clear expectations. The "best" business model depends on what you want your life to look like. For Eli, agencies weren't a step down. They were a strategic upgrade. Hiking His Prices Relying on Capacity and Confidence Eli's agency launched at $2,500 a month, not because that was the "right" price, but because he backed into a simple income goal. Sixteen clients at $2,500 got him to $40,000 a month. On paper, it worked. In reality, it broke fast. As soon as clients started saying "yes" too quickly, Eli knew something was off. The work was heavy, margins were thin, and building a team at that price point wasn't sustainable. Instead of obsessing over competitive pricing, he leaned into price sensitivity testing. Every time the team hit capacity, prices went up. If prospects said no, it didn't matter, they couldn't take on more work anyway. If prospects said yes, it justified hiring and scaling. Over three years, pricing climbed from $2,500 to $45,000 per month. What he learned was that underpricing doesn't just hurt margins. It traps you in constant hiring, delivery stress, and low-leverage work. Raising prices isn't greedy, it's operational discipline. What Actually Changes When You Raise Prices Eli didn't wake up one day and charge $45,000 for the same work he was doing at $2,500. Early on, the offering was vague: "We'll help with demand gen." Strategy was loose, scope was unclear, and the team was tiny. As pricing increased, the delivery model matured into a defined pod structure with paid media, design, strategy, and leadership baked in. However, once his agency hit around $15,000 per month, the services didn't change much after that. What changed was credibility. Case studies stacked up. Results became undeniable. Sales conversations shifted from "this is a great deal" to "this is what it costs to remove risk." Eli was upfront with prospects: MatterMade would be $10,000–$15,000 more per month than competitors, and nothing about the deliverables would look different. The difference was the track record. For buyers who weren't cash-sensitive, that pitch landed hard. They weren't paying for tasks. They were paying for certainty. Why Splitting One Agency into Two Was the Right Move At its peak in 2021, MatterMade was flying high, with $4.2M in EBITDA, tech clients everywhere, and acquisition talks underway. Then the tech market collapsed. Almost overnight, VC-backed clients cut agencies, froze spending, and hunkered down. They went from crushing it to losing nearly $200,000 a month. Eli held on too long, assuming it was temporary, and paid dearly for it. During the restructuring, Eli noticed something interesting: design had become a bottleneck across tech companies. Designers were laid off, but the need for creative work didn't disappear. So he spun up No Boring Design as a separate entity, fast. New brand, new site, launched in a weekend. Within months, it was profitable. Separating the businesses allowed each to have crystal-clear positioning. MatterMade stayed focused on growth marketing. No Boring Design became a premium creative solution for companies stuck in hiring freezes. Trying to keep design tucked inside the marketing agency would have slowed everything down. Separation created speed, clarity, and growth. Why Shared Services Across Agencies Sound Smart and Fail Fast One of Eli's biggest mistakes came after the split. He tried to create a shared management company to handle leadership, recruiting, and operations across multiple agencies. On paper, it looked efficient. In practice, it was chaos. Each agency had subtle but important differences in how it worked. SOPs drifted. Leaders got stretched thin. The "squeaky wheel" agency got attention while others suffered. Eventually, Eli unwound the entire structure. The hard truth: unless your companies operate almost identically, shared services create more friction than savings. Clarity beats efficiency. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
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4.8 out of 5
123 reviews
Inneraction Media 2024/12/10
Great podcast!
Jason Swenk is a powerhouse of insights for digital agency owners. With actionable tips and inspiring guest stories, it’s perfect for those looking to...
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Adarcus 2022/06/03
Must listen
Jason brings so many thought provoking insight on growing a business! He and his guests offer so much to all listeners!
Real Jedi 2011 2022/05/17
Awesome content
Tactical content with a purpose. I enjoy every show. Thanks for sharing your industry expertise 🤩
Bryan SD B 2022/04/02
Thanks Jason!
As an agency owner I have received such amazing and useful advice 🙏
malfoxley 2021/07/08
Great show!
Jason highlights all aspects of growing a business and more in this can’t miss podcast! The host and expert guests offer insightful advice and inform...
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Aidan Sowa 2021/07/07
Awesome Podcast
Loved being on the show!
Buddhaa22 2019/07/20
Valuable For Agency Owners
Jason brings great topics and value to owners. Definitely worth your time to grow your agency.
Tony Pec 2019/01/19
BEST podcast for agency owners
This is by far the most detailed & value packed podcast for an agency owner just wow ! Constantly mind blown by the information he delivers every sing...
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Autumn Shultz 2018/08/22
A must listen for Digital Marketing Agencies
If you haven't yet listened to this podcast, do it now. You won't be disappointed. Instead, you'll be delighted by the incredible tips and insights Ja...
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Luke Avedon 2018/06/16
FORCES You to Think BIG
It is impossible to listen to one episode and not start to think bigger. Finally, a podcast that ACTUALLY takes you from zero to hero. Each episod...
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