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

Jason Swenk

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.

  1. 5H AGO

    Why Your Agency Can't Scale Until You Stop Being the Doer with Matt Kovacs | Ep #893

    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.

    31 min
  2. Why Doing More Is Holding Your Agency Back (And What to Do Instead) with Darby Copenhaver | Ep #892

    3D AGO

    Why Doing More Is Holding Your Agency Back (And What to Do Instead) with Darby Copenhaver | Ep #892

    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.

    32 min
  3. MAR 25

    AI Is Reshaping Agencies. Staying Average Will Kill Yours with Brian Hansen | Ep #891

    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.

    29 min
  4. Why Agencies Lose Clients: Confusing Reports and Outdated Operating Models with Nate Jenson | Ep #890

    MAR 22

    Why Agencies Lose Clients: Confusing Reports and Outdated Operating Models with Nate Jenson | Ep #890

    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.

    28 min
  5. MAR 18

    What Do Private Equity Firms Look for When Buying an Agency? With Ben Gaddis | Ep #889

    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.

    36 min
  6. Burned Out Agency Owner to AI Architect: The Real Shift Founders Must Make With Austin Armstrong | Ep #888

    MAR 15

    Burned Out Agency Owner to AI Architect: The Real Shift Founders Must Make With Austin Armstrong | Ep #888

    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.

    29 min
  7. MAR 11

    Why Project-Based Agencies Feel Profitable But Aren't Sustainable with Michael Boychuk | Ep #887

    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.

    34 min
  8. How Forward-Thinking Agencies Win with SEO, GEO, & LLMs with Terry Zelen | Ep #886

    MAR 8

    How Forward-Thinking Agencies Win with SEO, GEO, & LLMs with Terry Zelen | Ep #886

    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.

    28 min
4.8
out of 5
123 Ratings

About

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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