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. 2D AGO

    The Identity Crisis Killing Agencies (And How to Rebuild Before It's Too Late) With Jonathan Lewis | Ep #895

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are agencies becoming obsolete? We don't think so. However, the traditional agency model isn't just evolving, it's breaking. Today's featured guest believes the core of every business is dying and that agencies that want to adapt and win need to adopt the mindset of rebuilders. He shares why agencies have been in decline for over two decades and what it actually takes to rebuild a business that survives AI, commoditization, and shifting client expectations. Tactics alone won't help because, at its core, this shift is about identity, positioning, and stepping into a new role as someone who doesn't cling to the old model but actively creates the next one. Jonathan Lewis is the President of McKee Wallwork, a brand strategy and implementation firm. Starting as an unpaid intern, Jonathan worked his way up to eventually acquiring the agency from its founders. Over the past decade, he's led the firm through a major repositioning, moving away from traditional agency work toward upstream strategic advisory. His perspective is shaped by firsthand experience navigating succession, industry decline, and the current AI-driven disruption. In this episode, we'll discuss: The declining agency model Why identity is the real problem Moving upstream The rebuilder mindset Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. The Agency Model Has Been in Decline for Years Most agency owners think the pressure they're feeling is recent, but it's not. Jonathan makes a strong case that the traditional agency model has been declining since the early 2000s, starting with the collapse of mass media dominance and accelerating through the rise of the internet, social media, and now AI. The old model was simple: control distribution, create decent creative, and scale results through reach. That model is gone. Today, agencies are fighting for perceived value in a world where clients question everything: speed, cost, necessity, and even whether they need an agency at all. This shows up in commoditized RFPs, price pressure, and constant comparison to cheaper or faster alternatives. The frustration many founders feel isn't personal failure; it's structural misalignment. They're trying to win using a model that no longer works the way it used to. The Real Problem Isn't AI, It's Identity A lot of agency owners are blaming AI for the disruption. That's not the real issue. The deeper problem is identity. Most agencies are built by craftspeople, designers, developers, media buyers who tie their value to the tools they use. When those tools become automated or commoditized, it creates an identity crisis. If your value is "I build websites" or "I run ads," you're in trouble. Because now those things can be done faster, cheaper, and in some cases better, without you. Your value is not the tool. Your value is the thinking before and after the tool, the judgment, the strategy, the ability to define what should be built and why. Moving Upstream: From Execution to Worldview In 2018, Jonathan and his team made a critical shift. They stopped trying to compete on execution and moved upstream into strategy, specifically, helping clients define their worldview. This is where things get interesting. AI can generate outputs. It can execute tasks. But it still depends on inputs, the prompt, the context, the perspective. That's where agencies have leverage. Instead of being the ones producing deliverables, they became the ones shaping direction. Helping clients answer: Who are we? What do we stand for? Who are we actually trying to reach? What matters most? From there, everything downstream becomes easier, whether it's done by internal teams, AI, or external vendors. This shift moves the agency from vendor to strategic partner. And more importantly, it removes them from the commodity trap. AI Is a Multiplier, Not a Replacement Jonathan takes a grounded view of AI. AI increases productivity dramatically. But historically, when something becomes more accessible, demand increases. Lower cost per unit doesn't eliminate demand; it expands it. The opportunity isn't in resisting AI. It's in integrating it while strengthening the human layer around it. You can use AI to analyze markets, generate insights, and accelerate content creation, not to replace thinking, but to enhance it. The real advantage comes from combining: Pattern recognition (AI) Judgment (human) Perspective (worldview) Agencies that only use AI for execution will get commoditized. Agencies that use AI to amplify strategic thinking will gain leverage. The "Rebuilder" Mindset Jonathan wrote a book around the idea of becoming a "rebuilder" because that's how he sees people getting through these times of reckoning in the business. Every major shift, from the internet, social media, COVID, and AI, breaks existing models. Most people respond by resisting, waiting, or reacting. Rebuilders do something different. They accept that the old model is broken and take responsibility for creating the next one. That means: Rethinking how you create value Redefining your role in the business Rebuilding your offer, positioning, and delivery model Leading your team through uncertainty instead of avoiding it It's ownership at a different level. And it's the difference between agencies that survive disruption and those that disappear with it. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.

    33 min
  2. Why Hiring Without Systems Multiplies the Chaos with Chris Seminatore | Ep #894

    5D AGO

    Why Hiring Without Systems Multiplies the Chaos with Chris Seminatore | Ep #894

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What actually breaks an agency first, growth or the founder's inability to evolve with it? And at what point does hiring more people stop creating leverage… and start creating chaos? Today's featured guest dives into why he decided to close his first business, which he had grown to 22 employees, and start again solo. He needed to get away from the chaos of managing a large team, but what is the crucial mistake he can avoid if he ever wants to scale an agency team again? Beneath the tactics, it becomes clear that the role of a founder must grow if they want to build a business that doesn't collapse without them. Chris Seminatori is the founder of Get Geofencing, an advanced digital marketing technique that helps small and large-scale enterprises meet their sales target effectively and efficiently. Chris shared his journey from scaling a 20+ person operation in Beverly Hills to intentionally stepping away from team-heavy growth after experiencing the hidden cost: constant management chaos. He talks about the evolution of advertising, from geofencing to connected TV, and how emerging technologies like AI are reshaping both service delivery and agency efficiency. In this episode, we'll discuss: The trap of hiring to grow What was the crucial mistake? Control vs. dependency What the Navy got right Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started. Herringbone Digital: If you're thinking about exiting now, planning a few years ahead, or just want to understand your options, you should know about Herringbone Digital. They're not a typical financial buyer. They're operators who actually understand what it takes to build and scale an agency because they've done it themselves. Their approach is simple: invest in great founders, protect what's already working, and help agencies scale faster. Go to https://www.herringbonedigital.com/swenk and start the conversation. The Trap: Hiring Only to Manage Chaos Chris's first business followed a familiar trajectory: start small, gain traction, hire quickly, and scale to over 20 employees. On paper, it looked like success, but it quickly became unsustainable. Each hire introduced new variables—different expectations, skill levels, and problems—until Chris found himself spending his days putting out fires instead of building the business. This is the inflection point many founders hit but don't anticipate. Growth creates complexity, and without structure, that complexity compounds. Instead of gaining leverage, Chris became the central node for every decision, issue, and escalation. The deeper issue wasn't the team itself. It was the absence of systems, clarity, and leadership infrastructure. Without those, hiring just amplifies chaos. Chris ultimately shut the business down, not because it lacked demand, but because it lacked structure. Why Most Founders Break When They Try to "Scale" Like many founders, Chris operated intuitively and ended up hiring before systemization. The "system" lived in his head, from how to deliver, solve problems, and serve clients. When he brought others in, they lacked the context and frameworks to operate independently. This created a loop: the team needed constant input, which pulled Chris deeper into operations, which prevented him from building the very systems that would free him. As a result, more hires led to more dependency, not less. Founders often misdiagnose the problem as "needing better people," when the real constraint is a lack of documented processes and clear direction. Without those, even great hires require heavy management. Scaling isn't about adding people. It's about reducing decision-making friction through structure. Without that, every new hire increases the founder's workload. The Alternative Model: Control vs. Dependency After shutting down his first agency, Chris rebuilt with a completely different model. This time it was lean, contractor-based, and highly controlled. This allowed him to maintain quality and ensure clients received the level of service he expected. The upside is clear: consistency, control, and alignment with his vision. There's no dilution of standards, no miscommunication layers, and no dependency on internal managers. For a founder who values craftsmanship and direct client impact, this model works. But the trade-off is equally clear. The business is entirely dependent on him. If Chris steps away, everything stops. Growth is capped by his capacity, and the business cannot function independently. This is the other side of the spectrum: instead of chaos from too many people, it's constraint from too much centralization. Both models reveal the same underlying truth: the founder's role has not evolved. The System Gap: What the Navy Got Right Looking back, Chris wishes he had implemented some of his Navy experience into his management. For instance, the military operates on clear objectives, defined processes, and structured decision-making. In that environment, the objective is explicit. Everyone understands the goal, the constraints, and their role in achieving it. Teams are encouraged to think and propose solutions, but within a defined framework. That balance creates both autonomy and alignment. Chris recognizes that he failed to bring this structure into his agency. Without clear objectives and documented processes, his team couldn't operate independently. Every deviation required his intervention. This highlights a critical shift: leadership is not about doing the work or even managing people, it's about designing systems that enable others to execute without constant oversight. The Future of Advertising: Precision, Data, and AI Chris also shares how his current agency is evolving alongside major shifts in advertising. Geofencing allows businesses to target users based on physical location, creating highly specific audience segments. Combined with connected TV (CTV), this enables precise ad delivery across devices, including household televisions. Traditional mass advertising is being replaced by targeted, data-driven distribution. Agencies that understand how to leverage this can deliver stronger results with lower spend, increasing their value to clients. Also layered on top of this is AI, which Chris used across the entire workflow, from creative development to campaign strategy. What once took hours or days can now be executed in minutes, often with better output. But while these tools increase efficiency, they don't solve the core structural problem. AI can enhance execution, but it doesn't replace the need for systems, positioning, or leadership evolution. The Real Constraint: Founder Dependency Across both versions of Chris's business, the 22-person team and the lean solo model, the same constraint appears: the business relies entirely on the founder. Whether that dependency comes from poor structure or intentional control, the outcome is the same: the business cannot grow or operate without the founder. This is the core challenge most agency owners face. It's not hiring, lead generation, or even service delivery. It's the inability to transition from operator to architect. Until that shift happens, every model, large team or solo, remains limited. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.

    26 min
  3. APR 1

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

    MAR 29

    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
  5. 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
  6. 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
  7. 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
  8. 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
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.

You Might Also Like