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

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

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 gr

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 inte

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

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 the

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