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

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Wendy Covey is the co-founder and CEO of TREW Marketing, a strategy and content agency exclusively serving engineering and manufacturing companies. She started the agency in 2008 — during the Great Recession — as a generalist, and within a year or two of niching down, won a Wall Street Journal Small Business Innovation Award.

Today, TREW Marketing is 19 years in, and Wendy has stepped fully into the owner role, with a president and leadership team running day-to-day operations. In this episode, Wendy and Jason dig into what it took to get there: the painful business partner buyout, the career path restructuring, and the niche positioning that now has clients convincing Wendy to take them on.

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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](http://e2msolutions.com/smartagency) and get 10% off for the first three months of service.

Key Takeaways:

• Niching down is the accelerant, not the limit. TREW Marketing chased anyone who'd pay in the early days — photo booths, nonprofits, product inventors. Once they committed to engineering and manufacturing companies, everything changed. Within a year or two they won a WSJ award, and today prospects come to them. Wendy's closing line: "It becomes them convincing me why they should be my next client."
• Your buy-sell agreement must include a valuation method. When Wendy's business partner left after 10 years, their agreement had no formula for valuing the business. Both sides got coaches, the negotiation was painful, and it strained a personal friendship. If you have a partner, get that language in writing before you need it.
• Build two documented career paths — individual contributor and manager — at the same salary band. TREW Marketing stopped the painful cycle of promoting great individual contributors into bad management seats by creating clear, documented tracks with defined behaviors for each. People can see where they fit before they take the wrong seat.
• Remove yourself from service delivery first, then tackle sales. Wendy's first move was getting fully out of client delivery. That freed her time to focus on sales and company growth. As sales grew, service delivery leaders naturally joined those conversations — and she found she was less effective in delivery minutiae anyway, making the transition feel inevitable rather than forced.

Wendy also shares how TREW Marketing's 19-year niche commitment is now paying off in the age of AI — their thought leadership content and deep expertise have made them highly visible in large language models, bringing in inbound leads without outbound effort.

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](https://flatworm-caterpillar-3mha.squarespace.com/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.

Would you like to learn how to accelerate your agency growth?

https://www.agencymastery360.com/training

Phil Davis is the founder and CEO of Tungsten Branding , one of the world's top-ranked naming and branding agencies, and the man behind hundreds of company names including PODS, RallyHouse, and TeamLogicIT.

Before Tungsten, Phil ran a full-service ad agency in Tampa Bay for 17 years before hitting an inflection point: he was succeeding by every external metric and miserable at the core of it. In this episode, Phil and Jason dig into the one question that cuts through all the noise of running an agency, why chasing revenue metrics is a trap, and what it actually means to build a business in alignment with what you want.

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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.

Key Takeaways:

• Ask "So I can what?" before you chase any goal. This is Phil's acid test: trace every goal back to what it actually gives you. Want a $20M agency? So I can what? Generational wealth? So I can what? Nearly every answer eventually bottoms out at peace of mind or freedom. If you know that upfront, you can stop building toward the wrong things.
• Chasing the wrong metric will hollow out your agency. Phil built a media-heavy agency that hit his revenue targets and left him wondering what the weather was like because he never stepped outside. The blur years, he calls them. The fix is not working harder; it is questioning which metric you are actually optimizing for, and whether it points toward a life you want.
• Marketing is a track team — sprinters and shot putters don't swap events. Trying to serve every client in every channel is the curse of early traction. Agencies that win pick their event. Phil pivoted from full-service to naming exclusively, and it became the thing that named PODS and landed Forbes Agency Council recognition.
• Right-sizing your team and mission is a relief, not a loss. When people get genuinely clear on what they want, the misaligned things fall away on their own. Phil shares the story of a Vistage member whose top salesperson quit after this exercise — and morale went up, not down. What looked like a disaster was the agency right-sizing around what it actually stood for.

Phil also shares why he named his agency Tungsten — the filament in the lightbulb — and how the concept of alignment, everything pointing the same direction to create flow, became the operating philosophy behind everything he does for clients.

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](https://flatworm-caterpillar-3mha.squarespace.com/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.

Would you like to learn how to accelerate your agency growth? https://www.agencymastery360.com/training

Arne Hurty is the founder and Chief Creative Officer of BayCreative, a San Francisco Bay Area B2B technology marketing agency he has been running for 30 years. What started as a $500 illustration job has grown into a full-service agency serving brands like Cisco and ServiceNow — with Arne's son and daughter now working alongside him.

In this episode, Arne and Jason dig into what actually sustains an agency owner over three decades: two business partner buyouts, a full pivot to remote work, and a philosophy of building the agency around life rather than the other way around.

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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.

Key Takeaways:

• The pursuit of quality is a bottomless pit — and that's why it works.** Arne says he has never seriously wanted to walk away from the business in 30 years. His reason: improving communication is an endless craft. If work feels boring, he says, "you're just not looking at it enough." The pursuit itself keeps going.
• Design your agency around your life from the beginning.** Arne made deliberate choices to keep BayCreative at a size that fit how he wanted to live. When COVID hit, going fully virtual wasn't a crisis — it was a natural next step that also opened the door to more diverse talent.
• Plan every business partner transition before you need to.** Arne has bought out two business partners over 30 years. In both cases, the transitions were manageable because expectations were clear. If you have a business partner, get the valuation method and exit terms in writing before either of you ever considers leaving.
• Let family earn their seat — don't create one for them. Both Arne's son and daughter joined BayCreative casually while in college and needing money. Their work quality is what made them permanent. Arne didn't build a role to justify hiring them; their capability justified itself.

Arne also shares how meeting someone in person at least once — even with a team that is otherwise fully remote — changes the texture of every Zoom call that follows. That first handshake, he says, carries more weight than any amount of video history.

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.

Would you like to learn how to accelerate your agency growth? https://www.agencymastery360.com/training

Leo Poitevin is the founder of Astrak, a fast-growing SEO agency based in Chiang Mai, Thailand, specializing in the French-speaking market. In just a year and a half, Leo grew his team from one to ten people — a journey that started not with a bold entrepreneurial vision, but with getting let go from a job during his probation period. In this episode, Leo and Jason get into what it really takes to go from freelancer to agency owner, how to reclaim your time as you scale, and the hard lessons of hiring your first salesperson.

Sponsors and ResourcesE2M 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.

Key Takeaways:

• Build for enterprise value, not freelance income.** The first year and a half of running an agency often means making less money than you would going solo. Leo reframed that trade-off by focusing on what he was actually building: a sellable company with real enterprise value, not just a higher hourly rate.
• Get your time back by compressing from the top down.** Leo's approach: start at maximum workload, then delegate piece by piece and block more time back into your schedule. If you start at 12 hours a day, there's only one direction to go. Every six months, something that used to live on his plate no longer does.
• Know what role you're actually hiring for before you post a job.** Leo discovered that "sales guy" isn't one job — it's a closer, an SDR, a full-cycle rep, and more. He and Jason break down why small agencies need someone who can do everything, and why matching your hire to your ICP matters more than industry experience.
• YouTube builds trust and leads even at small scale.** Without a large following or high-end production, Leo generates consistent inbound leads through long-form screen share videos. If you're struggling with lead generation, he says this is the most underused channel for agency owners.

Leo also shares how he built his sales process from scratch using a $7 online course, competitor proposal decks, and conversations with other agency owners — and why he believes you can't survive this industry long-term if you don't genuinely like people.

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.

Would you like to learn how to accelerate your agency growth? https://www.agencymastery360.com/training

John Jantsch is the founder of Duct Tape Marketing, a marketing agency he built over 30 years and the author of the bestselling book Duct Tape Marketing. He has since licensed his systematic marketing methodology to more than 400 agencies, consultants, and fractional CMOs around the world.

In this episode, John joins Jason to talk about the hard lessons of removing yourself from the center of your agency, why smaller agencies have a real competitive edge when they lean into being human, and why the fundamentals of marketing haven't changed; even as AI reshapes the tools we use.

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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.

Key Takeaways:

• The team is the result, not you. If clients believe you are the product, that's exactly what they'll demand. John shifted the dynamic by bringing team members into discovery calls early, showing clients they were getting a team — and a better outcome — not just one expert.

• Stop answering, start asking. John stopped giving his team the answers and started turning questions back on them. It felt uncomfortable at first, but over time it built a team that thinks independently and holds him accountable to staying in his lane.

• Scaling a methodology requires radical simplification. When John began licensing Duct Tape Marketing, he discovered that what lived in his head was 90% too complicated to transfer. It took 5 to 7 years of documentation, iteration, and simplification before the system was truly teachable by others.

• Marketing fundamentals don't change — delivery does. After 30 years, John's north star is the same: get someone who has a need to know, like, and trust you enough to buy. AI changes how you reach that outcome; it doesn't change what you're trying to accomplish.

John and Jason also dig into why trying to look bigger is often the wrong play for smaller agencies, how John grew key team members internally over 10 to 13 years rather than through traditional hiring, and why agency owners need to own a leadership seat with their clients — not just a tactical one.

Want a quick overview of John's system? Grab his free ebook at dtm.world/7steps.

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.

Would you like to learn how to accelerate your agency growth ? https://www.agencymastery360.com/training

What if your biggest growth bottleneck isn't your team—but how you're leading them?

Laura Lee Jones built Lion Share Marketing into a 45-person healthcare agency with an extraordinary retention record by focusing on people before processes. Rather than forcing employees into predefined roles, she learned to build roles around their natural strengths, creating an environment where team members stay for decades, leaders stay in their zone of genius, and the business continues to grow profitably.

In this episode, Laura shares how shifting from task management to strength-based leadership transformed her culture, why founder role clarity drives long-term growth, and why profit—not revenue—is the metric that ultimately matters.

What You'll Learn

• Why treating employees the way you want to be treated creates long-term retention.
• How managing people around their strengths outperforms assigning work based on organizational charts.
• The leadership shift from directing every task to building complementary teams.
• Why founders should protect the work only they can do—and delegate everything else.
• How staying focused on profit instead of revenue leads to healthier decisions.
• The connection between founder role clarity, team stability, and sustainable agency growth.

Key Takeaways

• Great retention isn't created through perks—it's built through consistent leadership and genuine care for your team.
• Stop trying to make people fit every role. Build roles around the strengths your people naturally bring.
• Founders become bottlenecks when they refuse to let go of work outside their highest-value contribution.
• Revenue growth means very little if profit, team health, and founder fulfillment are declining.
• Long-term agency success comes from designing a business where the right people are doing the right work—and the founder stays focused on the responsibilities only they can own.

Have you been losing good people and telling yourself it is the market, the economy, or bad luck? Maybe you've been watching revenue numbers so closely that you forgot to ask whether the profit and the life underneath them were actually working.

Today's featured guest runs a 45-person data-driven healthcare marketing agency she starting building just four days after being fired from an agency job. She'll get into why she intentionally built her agency thinking about employee happiness and fulfillment, how she evolved from drill sergeant to leader who plays to people's strengths, and what she has learned about staying profitable and mentally steady across three decades of business cycles.

Laura Lee Jones is the CEO of Lion Share Marketing, a Kansas City-based agency specializing in data-driven marketing for the healthcare industry. They build large patient and prospect databases, layers proprietary software on top of them, and uses front-end analytics and back-end ROI measurement to drive healthcare marketing decisions.

Laura Lee started the agency in 1995 after being let go from a firm she had run for ten years. She has grown Lion Share to 45 people with a retention rate that is genuinely unusual: some team members have been with her for close to 30 years, and several who could not join immediately due to non-compete agreements came over as soon as they could.

In this episode, we'll discuss:

• The standard that makes people want to stay 30 years

• Pairing people with the work they want to do

• Why revenue is not the number that matters the most

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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.

Why People Stay for 30 Years

Laura Lee does not have a complicated theory about retention. She built her agency around a standard she had for herself: treat people the way you want to be treated, and then actually do it rather than just saying it. When she wanted flexibility because she was going to be a mother, she built it into the culture for everyone. When she wanted to leave early on summer Fridays, she made two o'clock the standard. When she needed childcare, she added a daycare to the building so anyone on the team who needed it had access.

The outcome of that consistency over 30 years is a team that has watched each other's children grow from birth to college graduation. That kind of tenure is not built through perks or compensation alone, but through a founder who did not treat the team differently than she wanted to be treated herself, and who kept that standard even when the business hit years that were harder than expected. People can tell when a policy is real and when it is marketing.

Learning to Lead Instead of Just Direct

As Laura Lee herself admits, her early leadership style looked like a drill sergeant with a checklist, trying to fit square people into round holes. The evolution away from that happened as she paid more attention to what people were actually good at rather than what she needed done. Her agency's standard now is pairing people with the work their natural strengths fit, not assigning tasks based on organizational convenience and hoping it works out.

The specific example she gives is herself: she does not take detailed notes and never will. So she pairs herself with someone who does it well, gets the net summary she needs, and stays at the altitude where she is most useful.

That same principle applies across the team. The grumpy programmer who is brilliant at the work does not need to be socially engineered into a different personality. They need to be left in the seat where the grumpiness does not matter and the brilliance does. That is a structural decision that keeps the right people doing the right work and reduces the friction that makes good people leave.

Revenue Is Not the Number That Matters

Laura Lee has grown her agency every year but one in thirty years and she believes this is because she stays in the relationship and business development role that only she can fill, and she does not let herself get pulled into operations. The moment she drifts from that job, the numbers move. That clarity of role is the structural discipline behind the growth consistency.

For most founders, a revenue dip triggers alarm regardless of what is happening to margin. The more honest measure is whether the business is generating real profit, whether the team has what it needs, and whether the founder is actually enjoying the work. Laura Lee frames it the same way: you are the one who picks what your life looks like, whether you are an owner or not, and you can always pick again. Thirty years in, she is still picking.

Do You Want to Transform Your Agency from a Liability to an Asset?

Looking to dig deeper into your agency's potential? Check out ourAgency 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.

Would you like to learn how to accelerate your agency growth ? https://www.agencymastery360.com/training What happens when two founders build a successful marketing agency without ever clearly defining who owns what?

In this episode, John Scheer shares how eight years of overlapping responsibilities created hidden friction inside Herman-Scheer, and how a simple role clarification transformed the business. He explains why moving upmarket after the 2022 downturn required a completely different level of strategy, why bringing in a third partner accelerated growth instead of creating complexity, and how his agency is approaching AI as an amplifier of expertise rather than a replacement for it.

If you're leading an agency that's outgrown founder improvisation, this conversation is a masterclass in evolving your leadership before it becomes your biggest bottleneck.

What You'll Learn

• Why undefined founder roles create invisible bottlenecks, even when there's no conflict.
• How a 360° leadership review helped two co-founders finally divide ownership and improve decision-making.
• What it really takes to move a digital marketing agency from startup clients into Series A and enterprise engagements.
• Why adding a third partner succeeded after previous senior hires failed.
• How to evaluate executive talent beyond impressive resumes.
• Why AI should accelerate strategic thinking, not replace it.
• The 10-80-10 framework for using AI without sacrificing creativity or expertise.

Key Takeaways

• Clear ownership creates leverage. When founders stop sharing every responsibility, the team gains clarity, decisions move faster, and each leader can operate at a higher level.
• Market changes often demand business model changes. Herman-Scheer's shift upmarket after 2022 wasn't just about larger clients; it required stronger strategy, operational discipline, and deeper industry expertise.
• The right partner fills capability gaps, not title gaps. Their third partner succeeded because she wanted to build alongside the digital agency team instead of managing from above.
• Great branding is driven by judgment, not just creativity. AI can accelerate execution, but differentiation still comes from human insight and strategic thinking.
• Founder evolution is less about doing more and more about creating the structure that allows others to lead with confidence.

Have you and your co-founder been stepping on each other's toes for years, not because of conflict, but because nobody ever drew the line between your roles?

Today's featured guest moved across the country to Santa Monica after his current partner called him and asked him to take a chance on building something of their own instead of "working for the man". It took eight years of figuring out what not to do, a 360 review that finally split their roles, a niche into healthcare and wellness, and eventually a third partner to unlock what the agency is today. He'll walk through how the role division changed everything, why going upmarket after 2022 forced a more rigorous kind of work, and what he actually thinks AI is doing to branding.

John Scheer is the co-founder and chief creative officer of Herman-Scheer, a branding agency based in Los Angeles focused on healthcare, self-care, and well-being. They work with clients at three inflection points: zero to one startups, high-growth companies around Series A and beyond, and enterprise legacy businesses looking to regain relevance. Two and a half years ago they brought on a third partner with 20 years of operational and insights experience, which shifted the agency's growth trajectory significantly.

In this episode, we'll discuss:

• Two founders. No defined roles.

• The decision to move upmarket as a response to a shifting market

• Why the third partner hire worked

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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.

The Two-Headed Monster Problem

For eight years, John and Chapin ran Herman-Scheer without defined roles. Neither of them was trying to undermine the other. They just both did everything: sales, creative direction, project leadership, client management. Clients did not always know who to call. The internal team did not always know who to go to. And both founders kept stepping into the same spaces without realizing it was costing the agency something real.

The shift came from an outside advisor who ran a 360 review and surfaced the pattern clearly. Chapin got voted in as chief executive and John got voted in as chief creative. The way John sees it, they both got promoted at their own agency.

This way, clients knew who handled creative direction and who set operational direction. The internal team had a clear routing system. And for the first time, each founder could fully commit to a lane without the other one also running it. That kind of clarity is not just organizational tidiness. It is what makes both roles more effective and makes the agency feel less like two people doing the same job.

Why Going Upmarket After 2022 Required a Different Kind of Agency

John's agency spent several years focused primarily on zero-to-one startups, building deep roots in the Los Angeles venture capital and entrepreneurial community. It worked well until 2022, when the economic environment shifted and early-stage funding dried up. Founders who had been raising millions to launch consumer products suddenly could not. The client base Herman-Scheer had depended on was no longer buying at the same rate.

The response was a deliberate move upmarket toward Series A and beyond, and eventually toward enterprise legacy brands looking to regain relevance. That shift required closing the gap between brand strategy and execution, getting closer to conversion rather than staying in the lofty world of brand identity alone, and integrating more rigorous insights work into the process.

The outcome is that Herman-Scheer no longer competes on portfolio or personal chemistry alone. The decision to work with them is a decision to work with people who understand the healthcare and wellness consumer, the mechanics of those businesses, and what brand actually has to do at each stage of growth.

The Third Partner Hire and What Made It Work

John and Chapin hit another plateau several years after the reset. Revenue was solid. Growth had stalled and they both knew they did not have what it took internally to push through it. At this point, their advisor introduced them to Allison Servey, who had been head of strategy and insights at a major agency and had reached the point where her job was managing people and traveling rather than doing the work she was good at.

They'd already tried with big-company hires and failed, but hiring a senior person who wanted to roll up her sleeves again was the filter. People who come from large organizations where 10 people supported a single role often struggle in lean agency environments. Allison came in wanting to be close to the work, not above it. Within two and a half years she had helped manage out the people who were not a fit, brought in strong people from her network, and shifted the agency's operational foundation in ways that made the growth trajectory possible.

What AI Is Actually Doing to Branding

John is confident enough in his work to know that AI is not a replacement for creative thinking. What it has done is allow people to get ideas out more efficiently, which is genuinely valuable when used correctly. The problem is what happens when junior people or clients start treating the output as the finished work rather than as a starting point.

Herman-Scheer now includes language in their contracts preventing clients from submitting AI-generated onboarding forms. This means clients were doing it, submitting AI-filled questionnaires without reading them, and expecting the agency to build a strategy from questions answered by a chatbot with no real context about the business.

He makes sure AI usage at his agency complies with the 10-80-10 framework: 10% great thinking and prompting going in, 80% of the lifting done by AI, and 10% refinement and judgment coming out. That ratio requires real expertise at both ends. Without it, the middle 80% produces the average of everything the model has seen, which is not a brand strategy. It is a synthesis of other people's brand strategies.

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.

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training

Have you been hiring people and growing your team without a real plan, only to find yourself with a bigger payroll and a business that still runs through you?

Today's featured guest and his partner started out as graphic designers doing packaging work and then pivoted to web when the real estate crash wiped out their client base overnight. After years of taking on everything, they're still figuring out how to build the right team underneath them.

He walks through what it looked like to grow to 25 people without a plan, how the co-founder dynamic actually works after two decades, and why he's found that, in a partnership, the disagreements are actually the thing keeping the business alive.

Victor Huynh is the co-founder of Ready Artwork, a website-first industrial B2B digital marketing agency. He and his business partner Emily met in graphic design school and started freelancing together, with Victor handling sales and Emily anchoring production. Over 22 years, they pivoted from packaging design to web, grew to 25 people at peak, scaled back down, and have since committed fully to the industrial B2B niche.

In this episode, we'll discuss:

• Learning that clarity outperforms craft in sales

• The cost of growing without a plan

• Still dealing with imposter syndrome? Most owners are

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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.

The Black and White Sign That Rewrote Their Positioning

Victor describes the Asian expo as a pivotal moment in his agency's story and one where he and his partner learned what clarity actually does in a sales situation.

Day one at the trade show was a day of fancy brochures, a computer with carousels running, and exactly zero sales. Nobody knew what the agency did, and Victor grew frustrated as he listened to people walk past saying they thought the booth was selling colored pencils. On day two, Emily did not come back. Victor taped a black and white letter-sized sheet of paper in the corner of the table that said "website design" in Chinese and sold five websites.

The lesson is that clarity outperforms craft in every sales environment. The brochures were beautiful. The carousels were impressive. Neither of those things told a prospective client what the agency did or why they should stop walking. A simple, specific statement of what you offer is not a failure of presentation. It is the presentation.

Growing to 25 People Without a Plan and What It Cost

After the trade show success, Victor's agency grew fast. The strategy, if it can be called that, was reactive: someone needed something, they hired for it. E-commerce, lead gen, social media: they said yes to all of it because the projects were coming in and the team needed to grow to fulfill them. At 25 people, Victor describes feeling like they were selling a specific number of projects every month just to make payroll, and the agency had become something neither of them had designed.

The peak headcount created a structure where Victor never fully stepped out of sales. He had a sales team, but it functioned more like a support team. The direction that would have made the department self-sustaining was not there, and without it the team defaulted to managing up.

When the direction is not clear and the founder is always available to fill the gap, the team learns to route everything upward rather than developing the capability to own outcomes independently.

What a 22-Year Co-Founder Partnership Actually Requires

In their agency partner dynamic, Victor's partner Emily is the efficient executor. She makes sure things get done quickly, decisions get made, and production hums. He is the visionary and the sales front, in charge of new ideas, new opportunities, and new directions. The gas and the brake.

Those complementary traits are also the source of real friction. Victor gets impatient when things do not move fast enough. Emily resists new directions until someone answers who is going to do the work. What keeps the partnership functional is the willingness to have the hard conversation rather than let resentment build. Partnerships where disagreement goes unspoken long enough become toxic. Two decades in, he and Emily still go at it. The difference is that they work through it instead of around it. For solo founders, that sounding board does not exist inside the business, which is one of the clearest arguments for finding a peer room where the same kind of honest conversation can happen without the stakes of a co-founder relationship.

Imposter Syndrome Does Not Disappear With Experience

Victor names imposter syndrome as one of the things he still works on 22 years in. Most agency owners do. You might feel it as you walk up on stage for a talk and wonder for a second if you should really be there. What we should all learn is that the feeling is not evidence of being unqualified. It is evidence of caring about doing the thing well.

What imposter syndrome and delegation have in common is that both require the same underlying move: trusting that the outcome will be acceptable even when you are not the one controlling every detail.

The practical principle that runs through this entire conversation is that agency owners should remove the things they should not be doing, one at a time, and do it before it feels urgent to. Victor's efficiency instinct is the same instinct that eventually produces real structural freedom. It does not come from working harder inside the current setup, but from spending the hour building the system that removes the five-minute task permanently.

Do You Want to Transform Your Agency from a Liability to an Asset?

Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.

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Do your clients show up to calls with AI-generated strategies that are mostly wrong, and you then spend half the engagement correcting their assumptions instead of doing the work? Have you had clients who used to trust your expertise now question everything, armed with a chatbot and a YouTube video?

Today's featured guest is an agency owner who came up through programming, crossed into digital strategy, ran creative and media operations inside major holding company networks, and eventually went independent in search of the entrepreneurial freedom that corporate agency life could not offer. He goes into what AI is actually doing to the client relationship and what it means to train a team that can think rather than one that just produces faster.

Devon MacDonald is the president of Cairns Oneil, a Canadian media agency serving clients across North America. His career began in computer programming in the 1990s, working in HTML and SQL for clients in sales and marketing before moving into digital strategy and eventually running a creative agency and then a media agency network inside major holding company structures.

Five years ago, he went independent. He built a cross-functional AI team at his agency that includes both technical and non-technical members, operating from the belief that consumer insight and cultural understanding matter as much as data fluency in how AI gets applied.

In this episode, we'll discuss:

• Clients who have decided AI makes them the expert

• Is the funnel dead because of AI?

• Will this skill disappear once we've completely stopped using it?

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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.

The Problem With Clients Who Have Decided AI Makes Them the Expert

Devon knows there was already an education deficit in marketing before AI arrived. A generation of performance marketers came into positions of influence having skipped foundational thinking around brand, audience, and strategy. AI compounded that gap by giving them the ability to produce high volumes of output that look credible but are built on faulty premises. As a result, clients now show up with hundred-question emails generated by a chatbot, convinced they have done the strategic work when they have not done any of it.

The agency response to this cannot be frustration alone. It requires teaching. Devon's approach is to build client literacy around an abductive strategy: start with the vision, align everything to it, and use that alignment as the filter for which AI-generated inputs are worth pursuing and which are distractions.

That kind of structured thinking is precisely what a client who watched one YouTube video about replacing their agency does not have. And it is exactly what keeps the agency relationship valuable even when the client has access to the same tools.

Why the Funnel Is Not Dead, It Has Just Accelerated

Devon once heard at a conference that the funnel is dead because of AI. He pushes back on this claim saying that the path to purchase has changed. The speed of it has changed. The surfaces where awareness, attraction, and acquisition happen have shifted. But the underlying logic, that a buyer needs to become aware of something before they can want it, and want it before they can buy it, has not changed and will not.

The practical implication for agencies is that LLM optimization and branded search strategy are now front-line service offerings, not future considerations. Devon describes seeing this in RFPs already: clients are asking explicitly about model optimization and how agencies will help them show up in AI-generated answers. The agencies that can answer that question with a coherent framework are in a different conversation than the ones still positioning around traditional search rankings alone.

The Skill That Disappears When You Stop Using It

Devon shows genuine concern about what happens when a team stops doing the critical thinking and starts outsourcing it to AI. For instance, nobody knows how to navigate without Google Maps anymore. The skill atrophied because the tool made it unnecessary. The same thing happens to strategic thinking inside an agency when AI handles every first-order question without the team being required to form their own answer first.

Devon's response to this is to build the AI team cross-functionally, including people whose value is not technical. The consumer insight person, the culture reader, the account lead who understands what a client actually means when they say something: those perspectives shape how AI gets applied. Removing them from the process in favor of pure technical fluency produces faster output that misses the point. Let's not forget that human judgment is embedded in the workflow, not bypassed by 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.

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training

Are you willing to give up the work you built the agency around in order to build the agency itself? Today's featured guest recounts how he and his partner built their agency after a decade working together at the Oprah Winfrey Show. Fifteen years in, they are still figuring out what the founder job actually is versus what they have always been good at.

He talks through how the transition from doing to leading actually happened, what it cost him creatively and personally to step out of directing, and what he means when he says that making the video was always the easy part.

Brett Singer is a co-founder and principal at Bottle Rocket Media, a digital agency based in Chicago specializing in video production, motion graphics, SEO, paid media, and AI search optimization.

He and his business partner Dan Fisher both worked at Harpo Studios on the Oprah Winfrey Show for over a decade before launching Bottle Rocket in 2011. The agency built its initial client base entirely from the network that came out of Harpo when the show ended, then invested heavily in their own SEO to shift from outbound to inbound. Brett is now focused on business development, vision, and team culture.

In this episode, we'll discuss:

• Letting go of the work you love for the future of the agency

• When the business no longer needs you

• The hardest part of running an agency

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.

The Work You Love Is Not the Work the Business Needs From You

Brett spent years at Harpo perfecting motion design and later started Bottle Rocket partly because he wanted to keep doing it. It was work he greatly enjoyed. Unfortunately, he realized that was the wrong job for him, not from a strategic decision but from simple math: when he was in the edit suite, no one was finding the next client. The business did not care how good he was with a camera. It needed someone holding the relationship and the vision.

Letting go of the work he was trained for and genuinely good at did not happen cleanly. He describes it as kicking and screaming and slowly, and that is probably the most honest description of how most founders navigate this. In this case, the difference for him was having his partner, which meant there was always someone to hold the other accountable to the right job. Solo founders have to engineer that accountability differently. But the outcome is the same: the work you loved getting you here is eventually the work that stops the business from going further.

The Identity Gap When the Business No Longer Needs You

Stepping into the CEO role can feel like loss before it feels like freedom. When the business no longer needs you for the thing you spent a decade mastering, there is a real identity gap. The hours that used to be filled with something you were visibly good at are now filled with work that is harder to measure and slower to produce visible results.

Brett went through his own version of this as he transitioned away from directing. He still goes to set occasionally and feels the pull. He made peace with it not by letting go of the creative part of himself, but by redirecting it: into the sales process, into how the agency presents itself, into the culture he is building.

The creative instinct did not go away. It found a different channel. That reframe, from "I gave up my craft" to "I applied my craft differently," is what makes the CEO stage sustainable instead of a sustained identity crisis.

Making the Widget Was Always the Easy Part

Brett is clear about something that sounds counterintuitive until you have run an agency for a few years: the actual service delivery, producing the video, building the campaign, running the edit, is the easiest part of running an agency. The hard part is everything surrounding it. Hiring. Culture. Vision. Business development. Managing the people who manage the work. None of that was taught. All of it had to be built from scratch by people whose entire prior training was in making the thing.

This is the reason most agency founders stay stuck in the work longer than they should. It is the thing they know. Every hour in the edit bay is an hour that feels productive and measurable. Every hour in a hiring conversation or a strategy session feels less certain and harder to justify. The founders who scale are the ones who learn to value the less comfortable work, not because it becomes easier, but because they understand what it makes possible.

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.