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

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

  1. Why Your Agency Grows Slower When You're the Best Person on the Team with Olivier Bridgeman | Ep #906

    2D AGO

    Why Your Agency Grows Slower When You're the Best Person on the Team with Olivier Bridgeman | Ep #906

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Have you ever hired someone to free up your time and found yourself working more hours than before? Have you hit a point where your reputation for quality is actually the thing keeping you stuck in every project? Today's featured guest and his wife have been building their agency for over 22 years. For most of that time, the business ran on referrals, no defined niche, and two founders doing most of the work. Six years ago, they got serious about building a real team. In this episode, he talks honestly about what that transition looked like, why his technical strengths became a liability as the agency grew, how a lack of sales infrastructure was quietly making their delivery problems worse, and what the shift to actually picking clients has done for their operations. Olivier Bridgeman is the co-founder of Bridge Media, a marketing and web agency serving businesses in residential construction, renovation, and maintenance—recognized as the builders of credibility. Although it has been operating for over two decades, Olivier and his wife made the decision to build a real team and install the infrastructure that would let the business grow beyond them just six years ago. The agency now has 11 people, and Olivier is in the process of evolving out of the operator role and into something closer to CEO, working through the mindset and structural challenges that come with that shift. In this episode, we'll discuss: The expected cost of adding more people When your biggest strength turns you into a bottleneck Fixing sales to fix the delivery problem 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 Adding People Made the Work Harder Before It Got Easier After years of being the sole force behind the business, the motivation to build a team was simple: bring on people, hand off work, and get time back. The reality was that the first hires created more work, not less. Olivier and his wife had to deliver their own work, review and redo the team's work before it went to clients, manage schedules, clarify responsibilities, and absorb the cost of onboarding, all at the same time. This is the Manager stage in full effect, and it is the stage where most founders assume something is broken when it is actually just the expected cost of the transition. What Olivier describes is exactly what makes this stage so difficult: you used to know what you were doing every afternoon. Now you have to manage your own calendar and everyone else's. The invisible work of managing people, training them, setting expectations, and maintaining quality does not show up on any timesheet. It just accumulates. The goal is to move through this stage quickly, not to stay in it and hire more people on top of it. When Your Biggest Strength Becomes the Bottleneck Olivier's programming ability, which was his edge at the start, became a trap as the team grew. When you are the best technical person in the room and there is a problem in front of you, the reflex is to fix it. It is faster. It is cleaner. And it quietly signals to the team that you do not trust them to solve it themselves. The pattern is common across founders who built their agencies around a specific skill. The capability that created the business eventually becomes the reason the founder cannot leave it. Every time Olivier jumped in to fix something, he was reinforcing the team's dependency on him rather than building their ability to handle it independently. The structural answer is not to stop caring about quality. It is to raise the standard through coaching and systems rather than through personal intervention. The goal is a team that can hit 80 percent of what you would have done, on their own, then coach them to 82, then 85. Perfection is not the benchmark. Capability without you is. What Fixing Sales Did to Their Delivery Problem For most of Bridge Media's existence, new business came through referrals and local relationships. That felt safe. Working some local events and being known within their market was enough for a while. In practice, it meant every client was different, every project required a different set of skills, and the team was constantly starting from scratch. The founders had to stay deeply involved because the work never became repeatable enough for anyone else to own it. Two years ago, Olivier and his wife made a deliberate shift toward building an actual sales function. The downstream effect was not just more leads. It was better client fit, more predictable project types, and a team that could finally develop real expertise in a consistent area of work. When you build a pipeline, you get the ability to be selective. When you are selective, you take on clients your team can actually serve without the founders embedded in every deliverable. Referral dependency does not just create revenue risk. It creates a structural trap that keeps founders in the operator seat far longer than necessary. The Mindset Shift That Has to Happen Before the Role Can Change Olivier knows he needs to step back, and it is still hard. Not because the systems are not there, but because the identity is hard to separate from the work. When you have spent years building a culture of teamwork and being present for the team, stepping into a more removed role can feel like abandonment, both to the team and to yourself. The reframe that matters here is not about working less. It is about what the business actually needs from you at each stage. You may think that your biggest contribution to the agency is your time, but at the CEO level your job is: Setting the vision Communicating it consistently Coaching the leadership layer Protecting the culture through behavior rather than through presence Steering direction That work is roughly 20 hours a week when done correctly. The challenge is that most founders do not believe that until they have experienced it, and the discomfort of having fewer hours filled pushes them back into the operator role they just worked hard to leave. Recognizing the rubber band effect for what it is, significance-seeking disguised as contribution, is what makes it possible to stop pulling yourself back in. 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

  2. 6D AGO

    How to Build an Account Management Team That Owns Client Outcomes

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are your account managers drowning because you never built the system around them? Are you still the one clients call when something goes sideways, even though you hired someone to handle that? In seven years, today's featured guest and her co-founder built a team of six and developed an account management structure that worked well enough to earn a speaking slot at Elevate. She'll break down the exact touchpoint cadence her agency uses to retain clients and grow accounts, what she looks for when hiring account managers, and what it took to actually get out of the way. She'll also share what makes a co-founder partnership work when so many of them fail. Michelle Keckler is the co-founder of KNC Marketing, a full-service digital marketing agency based in Nashville, Tennessee. She and her co-founder Danielle launched the agency after Danielle was laid off from a company they both worked at. Within two months they had enough clients for Michelle to leave her corporate job. Michelle spoke at Elevate and has been a member of the Agency Mastery Mastermind. Her focus inside the agency is on client relationships, account management structure, and building a team that can own outcomes without founder involvement. In this episode, we'll discuss: How to set your account managers for success What to look for in an account manager Why letting go is not a one-time decision 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 Account Management System That Actually Retains Clients For Michelle, the first step to setting her account manager for success is to hand off ownership of that account to them right away and make that clear to the client. After that, they rely on a structured cadence built around three consistent touchpoints: weekly status updates so clients always know where things stand, monthly meetings to review campaign metrics and look at the next 30, 60, and 90 days, and quarterly business reviews that step above the day-to-day to assess overall direction and impact. What makes the cadence work is not the frequency. It is what happens inside each touchpoint. Michelle is specific about this: the monthly meeting is more than just a metrics review. It is an opportunity to ask the client what has changed in their business, whether they made a key hire, lost a team member, or landed a new account that shifts priorities. Often agencies get so focused on delivering the work that they stop asking questions that would help them serve the client better. That gap is where accounts quietly go sideways before anyone notices. Who to Hire for Account Management (And What to Actually Look For) Account management is one of the hardest roles to hire for because it requires a combination of skills that rarely come packaged together. Michelle is direct about this: you are looking for someone who can sit in a room with a client, speak confidently about the work, handle a difficult pricing conversation, and bring enough business understanding back to the internal team to actually inform strategy. She calls it a unicorn role, and she means it. What she's learned through experience is that marketing background matters less than business acumen and leadership mindset. Several of their best account managers came from strong business backgrounds with no formal marketing experience. They hired for values alignment and problem-solving ability, then trained the rest. The interview process shifted from culture-fit questions toward situational ones: how would you handle a frustrated client, tell me about a hard conversation you navigated. Knowledge can be taught. The instinct to lead a client relationship under pressure cannot. Getting Out of the Way Is a Decision You Have to Make More Than Once Michelle is honest about the fact that letting go of account management was not a one-time decision. It was a pattern she had to interrupt repeatedly. Early on she stayed involved because she knew her first hire personally. As the team grew, the justification changed but the behavior did not. advice from Darby, Agency Mastery's Agency Scale Specialist, to take the floaties off and let her people swim, stuck with her because it named the real problem: the systems were in place, the people were qualified, and she was still hovering. The practical shift that made the difference was removing a bottleneck in the operations structure. Danielle had been handling project management as an additional layer between account managers and the internal team. Moving project management back to the account management team eliminated a handoff, sped up delivery, and forced the account managers to own the full outcome of each client relationship. That structural change did more than any mindset shift could on its own. The role became clearer, the accountability became cleaner, and the team stepped into it. What Makes a Co-Founder Partnership Actually Work Michelle and Danielle are cousins who have built a seven-year agency together, which puts them in a small category. Michelle is candid about why she believes many partnerships fail and why theirs has not. The foundation is shared values and a shared goal for the business. The operating reality is that they have very different personalities, and that difference is a feature, not a bug. Danielle is the fast implementer. Michelle is the one who wants to think it through. One is the gas, one is the brake, and the business has avoided several train wrecks as a result. What she is clear about is that a partnership is not a shortcut. It requires the same kind of honest communication and tolerance for imperfection that any long-term relationship does. There will be stretches where one partner is carrying more than the other. There will be disagreements about pace, direction, and priorities. What matters is that both people want what is best for the business and the team, and can say the hard thing to each other when it needs to be said. Michelle is not selling the partnership model to everyone. She is saying that if you find someone with complementary strengths and the same core values, do not let the fear of conflict talk you out of 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.

    28 min
  3. The Agency Incubator Model: How to Fund SaaS Products Through Clients Instead of Investors with David Carnes | Ep #904

    MAY 10

    The Agency Incubator Model: How to Fund SaaS Products Through Clients Instead of Investors with David Carnes | Ep #904

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you running multiple things at once and wondering why none of them are moving as fast as they should? Are you still the one every project, every client, and every decision routes through, no matter how many people you have on your team? Over nearly three decades, today's featured guest didn't just run an agency. He turned it into an incubator, spinning up multiple SaaS companies, a mobile app, and an accessibility tool, all funded and validated through a model most founders have never tried. In this episode, he'll get into how he built products without outside investors, why the bottleneck is always at the top of the bottle, and what it actually took to step out of the operator seat after 28 years in it. David Carnes is the co-founder of Arcstone, a digital agency based in Minneapolis that has been operating since 1997. Over the course of his career, he has launched multiple companies from inside the agency, including a SaaS platform for associations built as early as 2000, a document management system called Wonderfile that was acquired by Blue Tie in New York, and NC, an accessibility scanning tool built initially for Arcstone's own quality assurance needs. His wife now runs Arcstone as CEO. David currently sits in the CFO seat, operating across all three businesses as an advisor and strategic layer rather than a day-to-day operator. In this episode, we'll discuss: Creating the structure to run several businesses and not be in the middle of everything Why the founder bottleneck is a trap you can learn to avoid Understanding the importance of creating dedicated AI roles 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. Funding Products Without Giving Up Equity One of the most practical lessons owners can take from David is how he funded multiple software products without investors. The model is straightforward: go to existing clients or a relevant group, identify a shared problem, and ask them to collectively fund the build in exchange for lifetime access. For AMO, six or seven associations each kicked in eight thousand dollars. For a later mobile event app, fifteen associations each contributed five thousand. In both cases, David had enough capital to build, immediate users providing real feedback, and zero equity given away. The reason this works is the same reason the Foot in the Door methodology works inside agency sales. A small, committed financial investment creates accountability on both sides. The customers who fund it show up with feedback because they have skin in the game. The builder ships something real instead of overbuilding in isolation. David was explicit that his own tendency to overcomplicate a product shrinks significantly when real users are in the room from day one. Too Many Plates, Not Enough Structure Building multiple companies inside one agency creates a specific kind of chaos. David called it too many plants in one pot. The companies start competing for the same resources, the same attention, and the same management bandwidth. His early answer to this was to stay in the middle of everything, which meant every decision still ran through him. The shift did not come from a framework or a book. It came from maturity and, eventually, necessity. When his wife stepped into the CEO role at Arcstone and dedicated management teams formed at AMO and NC, David moved into the CFO seat and took on what he called a monster back role, someone who can move across the whole field without being anchored to any single function. That is not a role most founders reach quickly, and he is honest about the fact that he still gets pulled back in when a longtime client or friend asks for something. The trap is familiar: you step in, you mean well, and in doing so, you signal to your team that you do not trust them to handle it. Founder Bottleneck Is a Pattern, Not a Personality Flaw David does not pretend he solved the founder bottleneck problem cleanly. In reality, patterns of it showed up repeatedly. You build structure, you step back, something pulls you in, and you disrupt the system you built. David described it as spiral growth rather than linear progress. You see the same lesson again. You handle it a little better. You move on. What makes the pattern more manageable is having a framework that names it. When you can recognize "this is the trap I have fallen into before," you can course-correct faster. That is exactly the work the Founder Evolution Framework is built to do. Operator, Manager, Architect, CEO, Owner: each stage is a distinct role, not just a job title. Revenue does not move you up the ladder. Removing yourself from the critical path does. David is living proof that even experienced operators with 28 years in the seat have to be intentional about each stage of that progression. AI: Surf the Wave or Get Pummeled By It David does not treat AI as a theoretical topic. He attended a ten-thousand-dollar immersive course shortly after Claude introduced persistent context, specifically because he wanted to understand what was actually possible, not just what people were saying about it. His takeaway was concrete enough that he created two dedicated roles inside Arcstone: an AI Architect and an AI Operator. The distinction is worth understanding. The Architect builds the agents and workflows. The Operator runs them, keeps the human in the loop, and catches the errors. Because AI still makes mistakes, and the founder who knows that firsthand is the one who can train a team to work with it well, not just use it. The agencies that will benefit most are not the ones that hand AI to someone and walk away. They are the ones who build internal capability, document their models and prompts as assets, and treat the technology as a force multiplier on a team that already knows what it is doing. 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.

    32 min

  4. MAY 6

    How One Bad Hire Turns a Marketing Agency Owner Into the Bottleneck with Scott Leff | Ep #903

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What if hiring smart people and getting out of your way was not enough to build a self-managing agency? Today's featured guest will talk through the decisions most agency owners get wrong: when to stay involved, when to let go, and how the absence of rigor compounds into structural problems you won't even notice until you're stuck. He'll talk about how bad hiring decisions led him to become the bottleneck, how he's trying to fix that, as well as why your "number" for how much your agency is worth is probably based on nothing, and the one financial habit that gives you genuine optionality. Scott Leff is the founder of Leff, a B2B content marketing agency serving global professional services firms and nonprofits for over 16 years. His background spans business communications working as a managing director for a big brand, as well as a 22-month stint leading communications for Chicago's bid for the 2016 Olympic Games. When the bid failed in the first round, he found himself in a period of reinvention. With the gig economy just taking off, he decided it was time to hang up his shingle. He started to take freelance work, which eventually led to hiring and forming his own business. This agency grew steadily, exploded during COVID, and is now navigating the reassessment most established agencies are facing in a shifting market. In this episode, we'll discuss: Why becoming the bottleneck isn't always about control The hiring rigor every owner should have Which metrics are you tracking? Why declining revenue doesn't equal failure 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. Knowing What You Should Never Have Delegated For the first ten-plus years of his agency business, every meaningful decision flowed through Scott or his business partner. That wasn't always a problem, but as the agency grew and decision-making had to push down through a management layer, cracks formed. Not because the team was incapable, but because they were being handed authority without the context, direction, or support to use it well. Hiring is the clearest example Scott points to. He gave department managers the autonomy to bring in their own people, which was a reasonable call on paper. But in a culture-driven organization like an agency, where your people are both your product and 80% of your overhead, that's the one decision you can't outsource and expect to get right. The fix wasn't micromanaging the process. It was figuring out the specific places where the founder's perspective is irreplaceable, and staying in the conversation there, even when it's uncomfortable to be involved. Hiring Rigor Is Not Optional and Most Agencies Are Winging It Scott attended a conference session led by someone who'd overseen hiring at Amazon and other large organizations. The biggest takeaway was a story about Jeff Bezos showing up to a debrief with three to four pages of handwritten notes on candidates, while everyone else showed up with nothing. That level of intentionality is what most agencies are missing entirely. The real problem isn't that agency owners don't care about hiring. It's that they go in underprepared, unclear on exactly what they're looking for, leaning on gut instinct, and writing role descriptions that don't reflect the actual job. To ensure you're getting applications from candidates that truly align with your agency and the required role, every part of the hiring process should be a test. Attention to detail? Bury the real application instructions at the bottom of the job post and see who finds them. Hiring a senior exec? Don't tell them much, give them a week and ask them to come back with a 90-day success plan. If they dive into answers before they ask a single question, that tells you everything. The point isn't the process for its own sake. It's that rigor on the front end reduces the cost of being wrong, and in an agency, being wrong on a hire is expensive for a long time. Watch Who You're Hiring From: Big Agency Talent Doesn't Always Travel Well There's a version of agency hiring that looks like a smart move: pull experienced people from larger, more established shops and let them install what's already working somewhere else. Here's why that doesn't work: You end up with talented people who are skilled at operating inside infrastructure, not building it. When there's no large team to direct, no resource pool to draw from, no SOP baked in for the last decade, they stall. The answer when things aren't cut and dried can be "that's not my job." And then it's nobody's job. Scott saw a version of this play out during the Olympic bid. Big consulting firms had seconded teams into the organization, and the ones who thrived were the ones who could operate in ambiguity. The ones who couldn't were waiting for a structure that was never going to show up. The lesson isn't that experienced people from large agencies are bad hires. It's that the ability to figure things out without a system to lean on is the filter. And you have to test for it explicitly, because someone's resume will not tell you whether they have it. Declining Revenue Doesn't Equal Failure, but You Have to Know What You're Actually Measuring Your revenue may seem like the only metric that felt like it matters when it's going up every year. However, a modest drop of five or ten percent, can be a big psychological blow even though profit improves and client impact is strong. That's a vanity metric doing its job: making growth feel like identity. Scott hit a similar inflection point when a former client asked him a simple question, why are you growing? Scott didn't have a clean answer. He'd been operating on the assumption that growth was inherently the goal, not a means to something else. The conversation points to a structural reality: if revenue is the only number you track, you'll optimize for it even when it costs you margin, leverage, and time. The healthier question is whether the agency is building toward the outcome you actually want, more optionality, a sellable asset, or just more control over your calendar. Revenue is a lagging indicator of that. Not the scoreboard. The Decision to Sell Your Agency Has Nothing to Do With Your Number Most agency owners carry a number in their head of what they want to walk away with when they sell. The problem is that the number is usually arbitrary, the market timing is unpredictable, and nobody warned them about the identity crisis that hits the week after closing. The right time to sell isn't a target revenue year or a specific EBITDA multiple. It's when you know exactly what you're walking toward and when the thought of running the agency has stopped feeling like a challenge and started feeling like a weight you've been carrying for six months straight. On the valuation side, Scott's question about what agency owners get wrong surfaced a hard truth: if your EBITDA is under a million dollars, your multiple takes a significant hit, and the buyer math looks very different than what you've been calculating off top-line revenue. Build the foundation like you intend to sell it. Get rid of what you hate. Make it structurally independent. Then you have real options,  whether or not you ever actually sell. 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.

    40 min
  5. How AI Tools Helped a 24-Year SEO Agency Vet Scale 5x Faster Without Burnout with Navneet Kaushal | Ep #902

    MAY 3

    How AI Tools Helped a 24-Year SEO Agency Vet Scale 5x Faster Without Burnout with Navneet Kaushal | Ep #902

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What separates the agencies growing through the AI wave from the ones quietly shrinking? Do you think you are on the right side of that line? Today's featured guest claims his agency has grown faster than ever in these recent years of AI ubiquity. He'll break down how 24 years of process obsession set him up to capitalize on AI before his competitors even stopped panicking. We get into the real mechanics of building SOPs that survive scale, why founders keep sabotaging their own teams (and how to stop), and how personal branding turned his sales calls into qualification calls. If you're running a $1M+ agency and still feel like the bottleneck, this one is going to sting a little, in the right way. Navneet Kaushal is the founder and CEO of Page Traffic, a white label SEO agency he's been building since 2002. He's since navigated every major algorithm shift, scaled through multiple hiring cycles, and now uses AI to encode decades of institutional knowledge directly into his systems. He's also built a recognizable personal brand through conference speaking worldwide and a growing YouTube channel, a move he credits as one of the top three drivers of his agency's recent growth. In this episode, we'll discuss: Building systems early on When founders undermine their teams Life after leaving the operator role: focusing on personal brand 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. Building Systems That Outlast the Founder Navneet has been doing SEO since before Google Penguin existed, back when keyword stuffing and reciprocal link building were legitimate strategies. Back then, barely anyone knew what SEO was and training people took a long time, so Navneet started growing his team by investing in three-day training sessions and hiring only those who would, by the end, understand basic SEO concepts. This initial investment in training also led him to focus on building SOPs since 2002, with his first being a printed sheet for reciprocal link building. That early process obsession became the foundation everything else was built on. More recently, he develops new SOPs by explaining the process to someone sitting next to him while simultaneously recording a Loom video. That method forces clarity. If he can't explain it simply enough for someone else to follow in real time, the SOP isn't ready. His onboarding process reflects the same rigor as Navneet's agency has grown to a 120+ person team and is regarded as one of the largest dedicated SEO agencies in India. Every new hire goes through a minimum six-to-eight-week onboarding, and every training module ends with a 100/100 quiz requirement. No partial credit or exceptions. That standard has kept quality consistent as the team scaled. The system doesn't bend to accommodate shortcuts. The hire rises to meet the standard, or they don't make it through onboarding. The Rubber Band Effect: When Founders Undermine Their Own Teams Even after he had the systems, the team, and the leadership layer in place, Navneet still felt the pull to go back and do the work himself. Not because the team wasn't capable but because SEO has always been his hobby. He genuinely enjoys it. So he'd chime in, jump back into SOPs, insert himself where he no longer needed to be. That's the rubber band effect. Your identity is still attached to the version of you that built the thing. Even when your role has shifted to CEO, part of you still wants to be the architect. The problem isn't the instinct, it's the impact. When a founder steps back into a team member's lane, it creates confusion about ownership, slows the team down, and signals that their work isn't trusted. Navneet's saving grace is that his longest-tenured employees have been with him for 17 to 20 years. They know his temperament and don't rattle. But for any founder with a younger team, this behavior hits harder. The goal isn't to never feel the pull, but to recognize it before you act on it. How AI Became a Force Multiplier, Not a Threat When most agencies were panicking about AI killing SEO, Page Traffic was using it to scale five times faster than before. The reason comes down to what Navneet had already built: two decades of documented processes that could now be packaged thanks to AI. He was able to transfer his entire knowledge base into software, so the institutional knowledge that used to live in his head (and required him to train people personally) is now embedded in the tools his team uses every day. New hires don't need Navneet in the room. They follow the process, and the process has his judgment baked in. This is the distinction matters because agencies panicking about AI are usually the ones that never systematized their knowledge in the first place. They're realizing that if AI can do what they do, they never had a real moat, just execution. Navneet had the moat. AI just made it easier to deploy. He's also building AI agents and automation services for clients, which created an entirely new revenue line. All because his agency already had the structure to absorb AI and deploy it fast. Personal Branding as a Pre-Sales Mechanism Navneet made a deliberate decision a few years ago to build his personal brand in parallel with his agency's brand. He started speaking at conferences around the world, doubled down on YouTube, and made sure that when people in his market searched for SEO expertise, they found both his company and his name. The result: he's now one of the only SEO leaders in India known both by agency name and by personal name. The business impact is direct. When a prospect reaches out to Page Traffic having already watched Navneet's content, heard him speak, or followed him online, they're not a cold lead, they're pre-sold. The qualification call replaces the sales call. You're not convincing them; you're deciding if they're a fit. That shift changes the entire dynamic of how deals get closed and what kind of clients come through the door. Founders who skip personal branding because it feels uncomfortable or "not their thing" are leaving their best pipeline tool on the table. People buy from people they already trust. The question is whether you're showing up in the places where that trust gets built. 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.

    17 min

  6. APR 29

    Your Agency Can't Scale Past the Role You're Stuck In with Dave Benton | Ep #901

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training How can you build an agency that outlasts your involvement in it? And what happens to your identity when you finally make that shift? Over the course of 22 years, today's featured guest grew a one-person freelance operation into a full-service digital agency doing eight figures and then sold it. In this conversation, he'll unpack the real lessons from that journey: the painful transitions between operator, manager, and architect, the hiring decision that finally unlocked his ability to step back from the work he loved, and why the question isn't just who you need on your team — it's who you need to become. Dave Benton is the founder and former CEO of Metajive, a full-service digital agency specializing in complex digital products and platforms. With over two decades of experience, Dave built his agency from freelance beginnings into an eight-figure business, eventually leading to a successful exit. Today, Dave is focused on innovation, particularly in AI, and how agencies must evolve structurally to remain competitive in a rapidly shifting landscape. In this episode, we'll discuss: Operator to owner evolution Recurring revenue as a growth lever AI as an operational requirement, not a competitive advantage 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. When Freelancing Becomes a Business Building an agency wasn't a single decision for Dave. It was an evolution that happened only after making several key decisions. It took him nearly eight years before the business truly felt like a company, not just a collection of projects and contractors. This delay wasn't due to lack of opportunity, but rather the absence of structural clarity. Like many founders, he initially relied on freelancers and partnerships to extend capacity. It wasn't until he introduced stability, through a small team and operational support, that the business began to compound. His experience reinforces a critical principle: agencies don't become scalable when revenue increases, but when structure stabilizes. The key mistake many founders make at this stage is avoiding the discomfort of responsibility. Hiring a team introduces fixed obligations in a variable revenue model, which forces a shift in thinking. The Founder Evolution Problem (Operator → Architect) Dave candidly describes this transition as "slow and painful," largely because he attempted to skip stages, trying to build a leadership team before the business could support it. This misalignment is common. Founders hear advice like "hire great people" or "get the right people on the bus," but apply it prematurely. Without the revenue, clarity, or systems to support those hires, it leads to inefficiency and frustration. The business must earn the right to complexity. Dave also dealt with the challenge of redefining his identity within the agency. He deeply identified as a creative director, which made delegation difficult because of his personal attachment to the work. This is the hidden bottleneck in most agencies: the founder's self-concept. The breakthrough came when he hired an exceptional executive creative director, someone good enough to replace him at a level he respected. This evolution required letting go of control, redefining his role, and shifting focus from output to system design. That transition, from doing the work to building the machine, is where real scale begins. Recurring Revenue and Stability as a Growth Multiplier Another critical unlock Dave shares is the role of recurring revenue in accelerating growth. His agency's trajectory changed significantly when they secured a long-term relationship with a major enterprise client, embedding a dedicated team within that organization. This shift introduced predictability, which is often underestimated in agency growth. Project-based revenue creates constant volatility, forcing founders to stay involved in sales and delivery. Recurring revenue, on the other hand, creates operational breathing room, allowing leadership to focus on systems, talent, and long-term strategy. Stability reduces decision fatigue, smooths cash flow, and enables more strategic hiring. Without it, agencies remain reactive. With it, they can become intentional. AI Is the New Baseline Both Jason and Dave challenge the common narrative that AI is a competitive edge. Instead, they position it as a requirement, similar to the shift from traditional to digital agencies years ago. Dave shares several striking data points: a growing percentage of B2B buying journeys now begin with AI-driven platforms, and a majority of deals are effectively decided before human interaction even begins. This changes the game entirely. If your agency isn't visible or credible within these AI ecosystems, you're excluded before the sales process starts. Internally, AI adoption requires structural integration and must go beyond tools. Dave's agency is experimenting with agents across functions, from development to QA to leadership coaching. The goal isn't efficiency alone, but capability expansion: turning team members into orchestrators rather than executors. However, this transition introduces a leadership challenge. Founders must balance urgency with stability, pushing teams to adopt AI without creating fear around job security. The agencies that succeed will be those that reframe AI as an amplifier of talent, not a replacement for it. Building an AI-Enabled Organization (Not Just Using AI) Many founders are using AI to enhance their own performance, but failing to distribute that capability across the organization. This creates a bottleneck, where the founder becomes even more central, not less. Dave is actively working to avoid this by equipping every department with tailored AI tools and training. Developers, designers, and producers each have different use cases, and the goal is to elevate the entire system, not just individual output. This aligns with a broader shift in agency structure: from teams of executors to teams of orchestrators. The future agency isn't defined by how many people it employs, but by how effectively those people leverage systems and automation to produce outcomes. The long-term implication is that agencies that fail to operationalize AI will face margin compression and reduced competitiveness. Those that integrate it deeply will unlock new levels of scale without proportional increases in headcount. 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.

    37 min
  7. Staying Small Is a Strategy with Madison Carr | Ep #900

    APR 26

    Staying Small Is a Strategy with Madison Carr | Ep #900

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What if scaling your agency didn't mean hiring more people or building a bigger team? What if the path to more freedom was actually designing a business that needs less, not more? In this episode, today's guest challenges the default assumption that growth requires headcount. She breaks down how she's built a highly specialized, one-person agency and why, when positioned correctly, that model can outperform much larger teams. But this conversation goes deeper than staying small. It's about intentional design. We unpack how niching down becomes a forcing function for simplicity, the hidden cost of staying stuck in the operator role, and why your evolution as a founder, not your team size, is what ultimately determines whether your agency creates freedom or quietly becomes a trap. Madison Carr is the founder of Creative Chameleon, a one-person branding agency focused exclusively on private schools. After spending years grinding as a generalist designer, taking anything and everything, she eventually niched into the education sector and built a reputation as a specialist. Today, she operates as both strategist and executor, working directly with school leadership teams on brand positioning, identity, and rollout, without a traditional agency structure behind her. In this episode, we'll discuss: Finding a promising niche The ups and downs of running a one-person agency Why founder identity is the real constraint 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. Niching Isn't About Marketing After a short-lived stint as an in-house designer, Madison knew her next step was to become a freelancer. She went straight to Craigslist, got some opportunities, and spent the next five years taking as much work as she could, without giving much thought to specialization. That phase is necessary. But it comes with a cost: inconsistent revenue, constant prospecting, and zero predictability. When you're taking any project that shows up, you're not building a business; you're renting income. As the industry continued to change, Madison recognized having the necessary business and marketing skills would be the only way to stay ahead. And once she did start to learn, all the advice seemed to point toward niching down. The problem was that no niche seemed promising enough to start saying no to other work. That is, until she landed a school client and leaned into it. Not because of strategy, but because the timing was right. Most niches are found, not planned.. Once she committed to that niche, everything changed. Sales got easier. Positioning got clearer. And most importantly, the business stopped relying on hustle. Instead of chasing work, she started operating inside an ecosystem where she understood the budget cycles, buying seasons, and decision-makers. The One-Person Agency: Freedom or Bottleneck? Madison made a deliberate decision to stay small. Not because she couldn't grow, but because she values being in the creative process. She doesn't want to become a full-time manager. She wants to build, not just oversee. For her, staying small meant she could keep doing what she truly loves, instead of either climbing a corporate ladder or running a bigger agency where she'd pass the creative work to junior designers. That's a valid choice. But it comes with tradeoffs. The upside is clear: direct client relationships, no overhead, higher margins on certain projects, and strong positioning as a specialist. For her clients, schools, working directly with the expert is a major selling point. The downside is just as real. Capacity is limited. Pressure is high. And certain opportunities, large, multi-disciplinary projects, are simply out of reach. The Real Impact of Niching: Operational Simplicity For Madison, one of the most underrated benefits of niching down has been that it greatly reduces operational complexity. Before, every project was different. Every client required a new sales process, new education, new expectations. That creates friction everywhere: sales, delivery, pricing. After niching, patterns emerged. She now understands: When schools buy How they make decisions What they actually value That eliminates a huge amount of wasted energy. Instead of reinventing the wheel every time, she's operating within a known system. And that stability reduces the emotional volatility most agency owners deal with, the feast-or-famine cycle. Founder Identity Is the Real Constraint It's important to distinguish whether the business is designed intentionally or just a reflection of the founder's current identity. Madison enjoys the pressure. She thrives in the tension. Right now, the business fits her. But that won't always be true. Every agency hits a ceiling when the founder stops evolving. If your role doesn't change, your business can't scale beyond you. It will either stall or start breaking under the weight of your involvement. This is the core idea: Your agency doesn't outgrow you. It gets limited by you. Whether you stay solo or build a team, the question isn't "what's the best model?" It's: Who do you need to become for the next stage of the business? AI Is Not the Threat, But Your Positioning Is Madison's approach to AI is: understand it, but don't blindly adopt it. Some clients want it. Some don't. Some see it as efficiency. Others see it as risk. As a tool, you can either use it to enhance your work or to undermine your value. This is something Madison has thought about as she prepared a talk for college students who will, at some point, become creatives entering the industry. How could she help them build skills that AI can't replace? Her advice was to use their brains and critical thinking, but not ignore AI and integrate it into their workflow. In the end, her clients aren't hiring her to generate assets faster. They're hiring her for judgment, strategy, and industry-specific expertise. That's the protection. If your value is tied to execution, AI will pressure your margins. If your value is tied to thinking, positioning, and decision-making, AI becomes 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.

    31 min

  8. APR 22

    The CEO Trap: Why Founders Either Check Out or Can't Let Go with Matt Nelson | Ep #899

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Does growth break agencies or does it expose underlying issues? It happens more often that founders expect. Even with momentum, scrappy decisions, loose roles, and unspoken agreements eventually become the very thing that holds the business back. And by the time it's visible, it's no longer a small fix. It's structural. Today's featured guest pulls back the curtain on that transition. He dives into the messy reality of starting an agency, navigating partner exits, building leadership layers, and the constant internal battle founders face when trying to let go. This isn't about tactics, it's about identity, structure, and the discipline required to stop being the bottleneck. Matt Nelson is the owner of First Tracks Marketing, an agency specializing in e-commerce, web development, and digital marketing programs. Unlike many agencies that niche down aggressively, Matt has built his firm around a repeatable process that adapts across industries. Over the years, he transitioned from being an employee to the sole owner, buying out partners, rebuilding the company's structure, and installing a leadership team that allows him to step back from day-to-day operations. In this episode, we'll discuss: How he learned to create a proper framework for a partner exit The lack of vision in his agency's early days The most significant shift: A leadership layer Two CEO traps that mess with the agency's growth Subscribe Apple | Spotify | iHeart Radio Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service. Toggl: Most agencies are losing 15–30% of their profit every year: lack of time tracking, messy manual timesheets, scope creep, untracked revisions, and all those "quick" client requests that never get billed. Toggl has created a fast, interactive way to uncover exactly where your margins are leaking. Start your investigation now at toggl.com/smartagency and use the code SMARTAGENCY10 at checkout for a 10% off annual plans. A Reactive Start That Created Complexity Down the Line Matt didn't start his agency with a grand strategy. Like many founders, it began out of frustration, leaving a poorly run agency and deciding to "figure it out" on his own. In his case, he worked at an agency that resisted change. In 2008, they still regarded digital work as a fad they would outlast. This frustrated Matt, who sensed this technology was the future of agencies. He wasn't the only one who felt this way, so he joined a couple of co-workers who decided to leave, rented an office across the street, and started their own business. This group had the vision but lacked structure, and this was evident early on. There were no operating agreements, unclear roles, and partners bringing in uneven value. At the time, it worked because momentum masked the problems. But as the business grew, those gaps became liabilities. This is where most founders get caught. They assume early success equals a solid foundation. In reality, early-stage growth often hides structural weaknesses, until scale forces those issues to the surface. If you don't build structure early, you'll pay for it later, either in painful partner exits, stalled growth, or both. Partner Misalignment Is a Structural Risk, Not a Personal Issue As the current sole owner, Matt has had to navigate multiple partner exits in the years since joining the business as an employee. These mostly happened not because of conflict, but because of misalignment. Different timelines. Different expectations. Different levels of contribution. The first exit was messy because there was no framework. There was no agreement or predefined process. Just emotion and negotiation. The second exit was different. By then, they had implemented an operating agreement, defined terms, and created a clear path for transition. That structure turned what could have been chaos into a controlled process. Most founders avoid these conversations early because things feel "fine." But without clear agreements, you're building risk into the business from day one. Why Lack of Vision Breaks Agencies Before Matt became the sole owner, the agency lacked a clear direction. They were doing good work and clients were happy. But there was no defined trajectory. That's a dangerous place to be. When there's no vision, the business defaults to activity. Projects get done. Revenue comes in. But nothing compounds. Matt's turning point came when he pushed for a strategic shift, relocating the agency to access better talent and reduce costs. He was thinking beyond execution and into positioning, hiring, and scalability. This is where founders start to separate. Operators focus on output. Leaders focus on direction. You Don't Scale Until You Build Leaders Under You The biggest shift in Matt's agency came when he installed a leadership layer: Creative Director Director of Development Director of Marketing Each owns a function, manages their own team, and is accountable for outcomes. It's a shift many founders resist. They hire doers, but not leaders, and then wonder why everything still runs through them. But real scale happens when decisions are pushed down, not escalated up. That's the difference between having a team and having a business that runs. Letting Go Isn't a Skill, It's a Discipline Even with structure in place, Matt still feels the pull to jump back in. Checking tickets. Fixing issues. Responding to clients. That instinct doesn't go away. What changes is how you manage it. Instead of stepping in directly, he routes issues through his leadership team and tries to reinforce accountability. It's still difficult for him and it's a point where most founders regress. They install systems, but break them under pressure. Choosing not to step in, even when you could, is about restraint. Because every time you do, you train the business to depend on you again. The CEO Trap… Boredom or Interference? Once you reach the CEO level, there are two ways you can get in the way of your agency's success: You jump back in to feel needed. You disengage because you feel irrelevant. Both break the business. Matt's solution has been creating structured involvement, quarterly planning, defining "rocks," and aligning the leadership team around long-term direction. This keeps him engaged at the right level, without collapsing back into execution. The goal isn't to remove yourself completely. It's to operate at the level the business actually needs. Incentives Drive Behavior, Not Motivation Matt is very aware that the agency's success lies with the team and their involvement and motivation. That's why he implemented a profit-sharing model. Not as a perk, but as alignment. When the team benefits directly from performance, they think differently. They take ownership. They care about outcomes, not just tasks. Most agencies struggle with engagement because there's no connection between effort and reward. With this model, he's managed to flip that. If the business wins, the team wins first. Do You Want to Transform Your Agency from a Liability to an Asset? Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.

    30 min
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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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