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

Jason Swenk

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

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    Why the Middle Layer of Your Agency Org Chart May Not Survive AI with Jennifer Bagley | Ep #841

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you still thinking of AI as just “ChatGPT with a better prompt”? Or maybe you’ve played around with Zapier automations and thought, yeah, that’s good enough. Today's featured guest knows that the agencies pulling ahead right now are building full-on AI agent networks that replace routine tasks, streamline data pipelines, and give their teams superpowers. She’s re-engineering her agency around AI and will talk about where she finds top-tier talent and why you don’t need to code to lead your agency into the future. Jennifer Bagley is the CEO and founder of CI Web Group, a fully virtual digital marketing agency registered in 22 U.S. states with clients across the United States and Canada. A former corporate operator turned entrepreneur, Jennifer started in real estate and mortgage brokerage before leaning into the marketing work she built to support those businesses. Today she runs a modern, tech-forward agency that’s rebuilt its stack around AI, centralized data, and agentic networks, all while carrying the scars and lessons of scaling, pivoting, and re-founding a business from the ground up. In this episode, we’ll discuss: Feeling trapped by the business. Hiring, firing, and the people reset AI, reskilling, and the end of “middle” roles What does this talent cost? 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. From Corporate Ladder to Accidental Agency Founder Jennifer came from an operations background, a self-proclaimed black belt in Six Sigma and certified project manager. Having built that corporate background, she had made a promise to herself (“by 30 I’ll be an entrepreneur”), and started to build the side hustle that became the main event. She started in real estate and mortgage brokering where she had to learn marketing the hard way; not because she wanted to be a marketer, but because the survival of her businesses depended on it. Initially, Jennifer didn’t set out to build a scalable agency; she built a team to support her broker network. When the market collapsed in 2008, the same team that did marketing for agents suddenly had a market outside real estate. That “we’ll just help this painter or HVAC company” phase is where the web group was born: small, service-focused, and useful to people in her network. That accidental turn became a business by solving real, pressing problems for paying clients, then leaned into that. Trading Time for Freedom: The Hard Pivot For the first five years, Jennifer describes the business as a “lifestyle” operation, profitable maybe, but trapping her time. She was trading billable hours for income and was reaching her limit when she hired a coach that forced a reckoning: if entrepreneurship isn’t buying you time, money, and freedom, what’s the point? So she made the brutal choice of cutting consulting contracts and burning the bridge to the “safety” of hourly work, and effectively gave herself a mulligan. This is the classic founder pivot: you have to choose between growth that keeps you doing the work and growth that scales the business without you. Jennifer’s reset wasn’t pretty, for a while she lost everything and she and her son lived in an office for a while, but it bought her the permission to build something salable, not just sustainable. Agency owners who feel trapped in delivery need to remember that sometimes you have to give up short-term revenue to create long-term value. Feeling Trapped by the Agency and Becoming a CEO Those first five years, Jennifer continued to run a business that started as a supply chain consulting and eventually turned into a sales supply chain consulting. This change meant the business was now a good lead generator for the agency but it also meant Jennifer was essentially selling her image and her time. Until she ran out of time. Once she felt trapped by the business, Jennifer actually hired a business coach that helped her change the model from “selling Jennifer with marketing on the side” to an actual sustainable business. She had to go back to the basics and remember she, like every entrepreneur, started the business with the idea of having more time, money, and freedom. It took losing everything, but Jennifer knew she didn’t want a lifestyle business, she wanted a sellable business. The antidote was delegation plus systems. If you want growth and a future exit, you need to own those CEO responsibilities and be comfortable with letting go of the day-to-day. Hiring, Firing, and Resetting the Team Jennifer’s talent strategy has evolved with each stage of growth. Her early hires were the classic “friends, family, fools” bootstrap crew; later she invested in developers, content teams, project managers, and over time, more strategic hires like CFOs, chief of staff, BI teams, and AI engineers. Each five-year arc brought a new set of needs and a new level of sophistication in hiring. Now, she divides her time between promoting her agency’s work in podcasts and content and thinking of ways to navigate her business in these volatile and exciting times. Her most recent addition to the team was a technology and transformation team that is revisiting all of the agency’s processes, investments, and infrastructure. As a result, she has downsized her team from over 300 W2 employees and refocus the team. The takeaway for agency owners: be honest about whether your people are builders or maintainers, and hire accordingly. The workforce you need for growth is not the same as the workforce you need for stable operations. Building AI Agent Networks with Centralized Data Jennifer’s agency shifted from WordPress to Webflow and built agentic networks: hundreds of AI agents that crawl competitors, do strategy homework, and automate tasks that humans used to do. More importantly, they rebuilt infrastructure into a hub-and-spoke model with a centralized min.io data layer and ETL pipelines feeding analytics and BI. Two big lessons here. One: invest in your tech stack deliberately so you’re not a Frankenstein of five different platforms that don’t talk to each other. Two: design your data architecture so your people (and your AI agents) have a single source of truth. That’s how you get from fire-fighting in six dashboards to proactive, predictive signals that tell you when a client engagement needs attention. AI, Reskilling, and Shrinking Middle Roles Jennifer draws a hard line: the agency now tends to hire either very seasoned client-facing leaders or AI engineers; the middle is shrinking. With agentic networks giving junior staff “superpowers,” the agency can afford fewer mid-level “lever pullers.” At this level there’s no room for slow execution or elementary work. That’s a cultural and ethical challenge, both for hiring and for workforce development. For agency owners, this raises practical HR questions: do you reskill your people, or replace them? Jennifer suggests building agent-driven systems that augment humans, and being brutally honest about who can grow into that future. It’s also a call to action for how we prepare the next generation: schools won’t teach this; companies will need to. Playing with AI Platforms: Why Leaders Need to Just Know Enough to Be Dangerous Jennifer started like a lot of agency owners dipping into AI, playing around on tools like n8n, Make.com, Relevance, and Longchain. Her dev team laughed, calling her an “elementary school kid on a tricycle,” but here’s the point: she didn’t need to master the tech. She needed to know enough to point her team in the right direction. Instead of obsessing over code, she framed the problem differently: “Here’s what I don’t want a human doing anymore. Can you make that happen?” That mindset shift is key for agency owners. You don’t need to be a full-stack AI engineer to lead an agency into the future; you just need to clearly define outcomes and invest in people who can deliver them. Find Real AI Talent in Unlikely Places This is where most agencies get stuck. You’re not going to find your next AI architect on Upwork. Jennifer leaned on her network, starting with her cousin Chris, a hardcore developer who initially thought AI platforms were “rookie business.” Once Chris realized the power of agentic networks to scale his expertise, he became the backbone of CI Web Group’s transformation. Now, she hunts talent in unconventional places: hackathons, LinkedIn, and especially YouTube. Forget the flashy “10x growth hack” videos — she looks for nerds with four views, geeking out about orchestrators and ETL pipelines. Those are the builders who care about solving real problems, not just building hype. Her tip: if you find one, reach out immediately. They don’t want sales, they just want to build. Designing AI Agents Like an Agency Org Chart Jennifer compares AI agents to a company org chart. You don’t hire one person to do everything, that’s a recipe for burnout. Same thing with AI. Each agent should tightly focus on a single task, with checks, auditors, and orchestrators overseeing the system. The payoff was massive efficiency gains. Instead of six different platforms that don’t talk, her agency built a centralized hub with min.io, ClickHouse, and AI layers on top. That’s how you go from patchwork automation to true predictive intelligence. The Real Cost of AI Talent If you’re wondering how much this all costs, the answer is… a lot. On the high end, seasoned AI engineers can run y

    29 min
  2. How Do You Sell (or Buy) an Agency Without Killing Culture? With Alyssa Ash | Ep #840

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    How Do You Sell (or Buy) an Agency Without Killing Culture? With Alyssa Ash | Ep #840

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What does it really look like when employees step up to buy the agency they’ve helped run for years? Today's featured guest will share how she and her partners carried forward the 30-year legacy of an agency founded in the days of print and stamp, a business that has not only survived but thrived through three different ownership handoffs. You’ll hear how they transitioned from licking envelopes to leading digital campaigns, navigated buying the business during COVID, and tackled the imposter syndrome that comes with suddenly being “the boss.” If you’ve ever thought about selling your agency, or buying one, this conversation is packed with lessons on culture, succession, and keeping an agency alive for the long haul. Alyssa Ash is one of the principals and co-owners of AOR, a creative and digital agency focused on branding, marketing, and web, with a strong focus on real estate development, municipalities, and economic development projects. Think housing solutions, community connections, and projects that shape cities—that’s their sweet spot. Alyssa and her two business partners are the third generation of owners keeping AOR alive since its founding in 1992. A rare kind of legacy in agency land. In this episode, we’ll discuss: How employees can be groomed into ownership. Lessons from buying an agency during COVID. Why imposter syndrome is normal (and even healthy). 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. A Legacy of Print and Culture Back in ’92, AOR wasn’t cranking out websites or SEO strategies. It was the time of print design, direct mail, licking stamps, and die-cut lounge chair mailers that made people long-time clients. It’s not common that an agency that gets acquired lives on like this, but the founders had built something special. Each generation of owners didn’t just grow the client list—they protected the culture. When the founders sold 13 years after starting the business, keeping that culture intact was non-negotiable. Fast forward again, and Alyssa’s crew inherited not just an agency, but a philosophy: honor the people and the community as much as the work. Transitioning from Employee to Owner Unlike an outside buyer swooping in with an SBA loan, Alyssa and her partners were homegrown leaders. They’d each put in 10–15 years, running departments in strategy, sales, and operations. By the time the second set of owners started floating the idea of selling, the trio was already running day-to-day operations. At first, the conversation was casual, “Would you even want to own the agency someday?”, but over time it got real. The financial side was initially not even part of the conversation, although they did give a reasonable runway of five to ten years for the acquisition to happen. The fact that three of them shared the load made the acquisition possible. While the thought was intimidating at first, the gradual handoff built their confidence. By the time the deal closed, ownership felt less like a leap and more like the next natural step. Navigating an Agency Acquisition During COVID If you’ve ever thought about buying or selling an agency, you know the financing part can get tricky. For Alyssa and her partners, COVID hit right in the middle of negotiations. On one hand, this made it somehow easier for her and her partners to step even more into their roles as heads of the agency. While the owners stepped back from daily operations, Alyssa and her partners made the transition to their new roles. On the other hand, the pandemic did complicate things as SBA loans looked risky with interest rates climbing. Thankfully, the old owners worked out a five-year owner-financed note instead. That decision didn’t just save them financially, it cemented trust. The outgoing owners wanted the next generation to succeed and structured the deal so everyone won. As Alyssa put it, “It didn’t feel like a big shift… because we’d already been doing it.” Fighting Imposter Syndrome (and Why That’s Healthy) Even with 15 years in the trenches, Alyssa admits stepping into ownership brought its fair share of imposter syndrome. She was still quite young, even though she felt comfortable leading day-to-day operations. This is where the former owner’s trust really helped. They put her in a position to succeed and trusted she could make it. Ultimately, every agency owner feels that, no matter the stage of their career they’re at when becoming an owner. In fact, it’s the ones who don’t who usually get tripped up by ego. Preparing the Next Generation So, is Alyssa grooming her team for eventual ownership? Not yet, it’s too soon. But she is watching for the traits that made her and her partners natural fits: entrepreneurial thinking, leadership instincts, and a bias for taking responsibility. Her advice to other agency owners thinking about succession: Don’t overlook your employees as potential buyers. Give them time and a runway to grow into the role. Protect your culture by keeping it in the hands of people who already live 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.

    19 min
  3. 24 SEPT.

    Agency M&A: Client Retention, Financing, and AI’s Role. The Inside Scoop with Zander Barth | Ep #839

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Most agency owners stumble into their first business almost by accident, learning as they go. But have you ever considered buying your first agency as a way to enter the industry with a head start? The right acquisition can give you an established team eager to keep growing, a base of engaged clients, and strong positioning in the market. Today’s featured guest took this path and is now the proud owner of a thriving agency. He always knew he wanted to run his own business, and when it came time to choose an industry, the agency model was the perfect fit for his love of project management and tech. He shares how he chose and purchased his agency, why he was fortunate to instantly click with the previous owner, the kind of deal structure he recommends for these situations, and the lessons he’s learned along the way. Zander Barth is the Director of Colophon New Media, a website development and digital marketing agency in Charleston, South Carolina. He isn’t your typical agency owner since he didn’t start his agency from scratch. Before that, he was managing boiler houses and wastewater plants as a chemical engineer. His path went from factory floors and Tesla consulting gigs to agency owner. In this episode, we’ll discuss: Why buy instead of build an agency from scratch? Retaining clients and culture in an ownership transition. Acquisition deal structure: earnouts, financings, and gotchas. 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. Buy vs Build: Why Acquistion Wins Most agency stories start the same way: someone freelances, gets referrals, and suddenly they’re running an agency. Not Zander. Having always wanted to work for himself, he was set on finding a business to acquire after realizing he didn’t want to stay in the corporate grind. Instead of an MBA, he gave himself what he calls a “redneck MBA”—a crash course in QuickBooks, masterclasses, and every free course he could get his hands on. His search started broad. He looked at electrical contractors, engineering firms, and everything in between. But when a broker introduced him to Colophon New Media, something clicked. The agency world lined up with his love for project management, customer communication, and tech. He hit it off with the founder, who was ready to retire, and within four months, Zander was under a Letter of Intent (LOI). The Transition: Keeping Clients and Culture Intact One of the biggest risks in buying an agency is losing clients or losing the team. But Zander got lucky. The founder stayed on for six months to ease the transition, the team had incredible tenure (average of 8–10 years), and clients stuck around. Instead of turnover chaos, he stepped into a culture that was already strong. What he focused on was core values. He knew the agency’s success was built on the team’s shared beliefs and long-term commitment. His goal: protect that culture while adding new faces who align with it. Processes and systems matter, but at the end of the day, it’s the people and values that keep clients around. The Deal: No Earnout, Straightforward SBA Financing Zander’s purchase deal was simple: 10% equity down 10% seller note 80% SBA loan (7A) No earnout. Was it risky? Maybe. But for him, it worked because he and the seller had great rapport. They respected each other, and shared the goal of keeping clients happy and the agency thriving. However, Zander is very aware of how lucky he was and that is not always the case. So his advice for agency owners is to structure the deal in a way that people are incentivized to help the business grow after they’re gone. Pro tip: Before buying, always ask the seller why they’re really selling. Burnout, boredom, or just wanting to hit the road in an RV with their spouse - it all matters. If their motivations align with your vision, you’ve got a shot at a smooth handoff. Surprises, Gotchas, and the Role of Luck in Acquisition Every acquisition has surprises. For Zander, it wasn’t massive skeletons in the closet but rather small bits of “tribal knowledge” that came up months later. Old client quirks, history buried deep, the stuff you don’t see in due diligence. His mindset was just to roll with it. “I just try to get good at riding the wave,” he said. And he’s honest about it: luck played a big role. You can prep all you want, but signing a deal that puts you on the hook for big debt is scary. You’ve got to trust your gut on the seller and back yourself to figure out the rest. Zander’s advice is to make sure you vibe with the seller. As odd as it sounds, there’s nothing more important in his experience than feeling he was able to truly understand the seller. He wanted someone who was really proud of their legacy and willing to grow and protect it. How AI is Shaping M&A and Agency Operations Back when he bought the agency, Zander was still not using AI in both due diligence and agency work. Now, however, he’s building “co-pilot bots” to analyze data, troubleshoot, and even stress-test M&A opportunities. His advice for other agency owners: if you’re not using AI daily, you’re leaving efficiency—and insights—on the table. AI won’t always 100% right, but it gets you thinking differently. For M&A especially, tools like ChatGPT can surface blind spots you didn’t even know existed. 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.

    18 min
  4. How To Find and Keep the Right People to Scale Your Agency with Dan Salganik | Ep #838

    21 SEPT.

    How To Find and Keep the Right People to Scale Your Agency with Dan Salganik | Ep #838

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Is hiring one of the biggest challenges you’ve faced when it comes to running your agency? How do you sift through hundreds of applications when most don’t even read the job description? Today’s featured guest opens up about the realities of building a team, the role that gave him his time back, and why finding the right people, not unicorns, but the right fits can make or break an agency’s growth. Dan Salganik is the managing partner and CEO of VisualFizz, a Chicago-based digital full-service marketing agency. He spent years working at agencies of every size and learning of the many flaws in their operations: bloated overhead, work designed more to win awards than to serve clients, and inefficiencies everywhere. Instead of sticking it out, he decided to try something different. With the help of a co-founder he met online, he turned his freelance gig into an actual business. Within nine days of their first conversation, they had their first paying client. Once they were at three clients, they decided it was time to make it official and started VisualFizz. In this episode, we’ll discuss: The digital nomad myth. Hiring as the biggest challenge for agency success. The unicorn problem. Why the big guys should be worried. 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. Inspired to Create Something Better After Working With The Big Guys Dan’s path into agency life started straight out of college, working at agencies as a project manager. He saw how the big guys worked and was frustrated by the waste. Expensive office space downtown, teams focused on portfolio-building instead of client results, and layers of inefficiency that didn’t make sense to him. After a layoff, he started contracting and freelancing. After a while, he figured if he was already selling his time, why not build a team and sell more than just his own hours? Partnering with a co-founder who brought SEO and paid search chops, he launched VisualFizz for just $50 and a “crappy logo.” The Digital Nomad Myth At first, Dan thought the digital nomad lifestyle was going to be the dream. He traveled through Asia, working out of hostels, hopping on 2 a.m. client calls from rooftop hotels, and running projects with a global team scattered across South Africa, Kuwait, and the U.S. It sounded cool on paper—but the reality was brutal. Trying to serve U.S. clients while living 12 hours ahead was a recipe for burnout. As he put it, “If you’re traveling to Southeast Asia and trying to hit U.S. hours, you’re in for a rude awakening.” Over time, he realized international travel had to shift into more realistic time zones if he wanted to scale the agency. From Scrappy Start to Scaling Smart VisualFizz didn’t take off by accident. From the beginning, Dan and his co-founder knew they wanted more than just a freelancing partnership. She had the technical expertise, he had the business and sales skills, and together they leaned into that divide. Their first clients came on at around $2,500/month retainers, which felt big at the time. But what really set them apart was their willingness to sell the agency model—not just themselves as individual contractors. Dan admits the early days were DIY to the extreme. He designed the first website, created the brand, and hustled every step of the way. But over time, they shifted from being “just two freelancers” into a legit business with structure, processes, and a growing client roster. Why Hiring is Always the Hardest Part Dan didn’t hesitate when asked about the hardest part of running an agency: hiring. In a business where you’re selling knowledge and time, having the right people is everything. And finding those people can be tough, especially for smaller agencies. Posting a single job ad often results in 700 to 1,500 applications—most of which are noise. Dan prefers entrepreneurial-minded hires over candidates with perfect credentials. He values people who can adapt, who want to learn, and who bring a cultural fit to the table. That’s how he’s built a team that can handle change in an industry that shifts constantly. Like most founders, Dan has had terrible interview experiences with candidates who applied mindlessly as soon as they saw an opening and didn’t bother to read anything about the profile required. People were showing up to interviews while in their card eating, not even knowing the company’s name, and clearly not having the skills required. If you’ve ever found yourself in this position, overwhelmed by resumes and constantly interviewing the wrong people, bury a hidden instruction in your job post, like requiring a candidate to send a video with a specific subject line to a private email. The people who follow directions prove they’re serious. The rest self-select out, saving you hours of wasted interviews Tired of the fancy resumes and disastrous interviews, Dan has turned to his contractors. He’s hired people who had contracted with the agency for years, which of course had the advantage of already understanding their capabilities and knowing they were up to the task. Furthermore, Dan considers himself to be very fiscally conservative when it comes to hiring, so he prefers working with the person until he feels he can comfortably hire them to be a full-time team member. The Hire That Changed Everything For Dan, the biggest game-changer was bringing in a project manager who grew into a project lead. Having someone who could take ownership of processes, build out SOPs, and even tell him to log off at 6 p.m. gave him the space to focus on the bigger picture, strategy, branding, and biz dev. The right project manager isn’t just checking boxes. They protect your time. They let you walk into client conversations clear-headed instead of stressed about whether a deliverable is behind. When they can run the team and operations, you can finally do the job of a CEO: winning new business and setting the direction of the agency. Stop Chasing Unicorn Hires What’s the next hire on Dan’s list? A hybrid between a campaign strategist and a creative marketing manager. Someone who can think strategically, get hands-on with campaigns, and still spot when an SEO report doesn’t make sense to a client. Sounds great but also sounds like a unicorn. As most agency owners eventually learn: unicorn hires exist, but you can’t build a hiring strategy around finding them. Instead, hire clearly defined roles—project managers who love execution, account managers who thrive on client leadership. When you stumble across someone who can flex across lanes, great. But don’t make that the expectation. How to Train Your Team to Sell Naturally Dan’s agency doesn’t run with a traditional account manager structure. Their PMs double as client leads, which means Dan had to find a way to make sales training part of the culture without turning his team into pushy salespeople. The secret to this training is storytelling. Instead of saying, “Hey, we can upsell you,” his team learns to connect client comments with relevant success stories. If a client mentions running a content audit, a PM can naturally suggest looping in the SEO lead, not because they’re chasing revenue but because they know it will help the client. Over time, this approach builds trust and positions the agency as a partner, not just a vendor. Positioning in a Shifting Market Dan has seen client expectations are moving “down a notch” lately. Big brands that once chased Ogilvy or Leo Burnett are now hunting for mid-sized partners. Those mid-sized companies are shifting to smaller shops. And boutique agencies like VisualFizz are landing $100–500 million clients who want to be a top priority instead of client number 142 on a massive roster. It’s the boutique hotel effect. Clients don’t always want the 3,000-room resort. Sometimes they want the place where the staff knows their name, treats them like the biggest deal in the building, and still delivers world-class service. For smaller agencies, that’s a huge opportunity to win the types of clients that used to feel out of reach. Why Lean Agencies Have the Edge The future isn’t kind to bloated agencies. What used to take 100 people a few years ago could now be done with 40, or even 15. Large firms with huge overhead and outdated models will struggle unless they pivot, merge, or find a vertical niche. Meanwhile, smaller and mid-sized agencies that can move fast, price smart, and deliver with a lean team are better positioned than ever. As Dan put it, even Fortune 500 companies are asking, “Why should I pay $50k a month for SEO when I can get the same expertise at $8k?” 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.

    27 min
  5. 17 SEPT.

    Why Do Agency Owners Feel Trapped in Their Own Business? And How To Break Free with Dan Fisher | Ep #837

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Ever feel like running your agency is just one long grind of “good enough” projects, endless deadlines, and late-night work sessions? Most agency owners start out chasing freedom, only to find themselves trapped by clients, culture challenges, and their own workaholic habits. Today’s featured guest is certainly familiar with this cycle, so how was he able to build a business that works for him instead of the other way around? By focusing on clarity, culture, and constant evolution. Dan Fisher is the founder of Bottle Rocket Media, a Chicago-based video production and digital marketing firm. Before running his agency, Dan spent a decade in television, including a long stretch as an editor at The Oprah Winfrey Show. What started as “making a few videos for people” turned into a full-fledged agency after his partner joined. Today, Bottle Rocket Media blends storytelling with digital strategy to help brands communicate with impact. In this episode, we’ll discuss: Data meets creativity. The agency he “thought he should build” Culture as a compass. Redefining work and energy. 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. Leaving TV for Agency Life Dan wasn’t setting out to build an agency. He was a New York kid, worked on TV production in LA, and then got tapped on the shoulder for a gig at Oprah. When he landed in Chicago, he figured he’d be there a couple of years. Ten years later, he had a family, a house, and roots that weren’t going anywhere. After leaving TV (not a moment too soon, according to him), he just started making videos for people. Then his partner came on board, and suddenly it was more than a side hustle. It was a real business. That’s when Dan realized he was no longer just a TV guy—he was running an agency. What TV Taught Him About Storytelling TV wasn’t all glitz. Dan loved the storytelling, the cameras, the lights. However, running a daily show can crush even the strongest souls. Deadlines piled on top of deadlines. Three to four episodes a week meant three to four immovable deadlines every week. Still, it gave him his 10,000 hours. He learned how to tell stories fast, direct, edit, and manage creative teams. Most importantly, TV taught Dan the importance of knowing your audience. At Oprah, there was always an “audience of one”—Oprah herself. He’d have the version he wanted to tell, and then the version she’d actually approve. That lesson carried into agency life: storytelling isn’t about you, it’s about your client. You’re not making an indie film; you’re telling their story in a way that serves their brand. The Continual Evolvement of Creativity Bottle Rocket Media isn’t trying to be Hollywood. They focus on nonfiction storytelling, documentary-style content, education-driven pieces, spokespeople, and commercial spots. What makes their approach stand out is how they marry creative instincts with marketing data. Working in the creative field never ceases to surprise Dan who, even now, expects something to land well with audiences and sees the complete opposite happen. This is why he and his team lean into A/B testing. Sometimes it’s the tiniest tweak: a subject line in an email, a color shift in a graphic, or moving the ending to the front of a video. It’s a reminder agency owners need: you can be confident in your craft, but the market has the final say. From Filmmaker to CEO When he started, Dan assumed he’d be miserable doing the “operations” side. But mentoring, managing, and building a team turned out to be just as rewarding as calling “action” and “cut.” He’s learned the balance between doing and teaching. Having 10,000 hours of experience doesn’t mean you always tell the story better than a fresh intern. It means you know how to refine, manipulate, and see perspectives others might miss. At Bottle Rocket Media, they encourage collaboration. Editors critique each other’s work. Ideas bounce around. And Dan stays focused on a critical question every creative leader should ask: Am I making it better, or just making it different? From “Good Enough” to Defining Excellence It took Dan years to reach what he calls his maturity, after trying to be “the agency he thought he should be”. Eventually, after banging his head against the wall for a long time, he realized the power of clarity—both personally and professionally. He started the business as a way to make ends meet after leaving TV, but it was time to define his goals with the agency and make it his own. Once he stopped chasing someone else’s model and leaned into his own strengths, everything changed. The real turning point wasn’t in working harder, but in defining what success actually looked like for him and his team. Culture as a Compass Clarity doesn’t just guide you, it’s also something you can instill in your team. Once Dan started defining his agency’s beliefs, he could attract people who truly fit. To him, if your team is not going in the same direction, then what’s the point? But culture hasn’t been easy, especially post-pandemic. Bottle Rocket Media runs on a hybrid model: three mandatory in-office days, with Mondays and Fridays remote. For Dan, it was about letting go of his old Gen X “first one in, last one out” mentality and adapting to a younger workforce. The result is a stronger, more unified team—even if they’re not physically together every day. Redefining Work and Energy Coming from TV, where it’s not rare to work up to 70 hours a week, Dan initially started his agency using the volume model, which is what he knew. Once the business was up and running, his hours were still pretty similar to what he was used in TV. Eventually, however, it got to a point where a trusted employee expressed he was at his breaking point, and Dan knew it was time to dial down. Working beyond a certain limit didn’t make him better, it was just making him an ineffective leader. That shift changed how he managed his team, starting by cutting off the bottom 20% and elevating the types of projects they do. This way, with clear goals and clear deadlines, he’s building the kind of leadership that creates loyalty and sustainability. Always Be Evolving The agency game changes daily. Right now, AI is shaking up video and digital marketing. What worked yesterday won’t always work tomorrow. If you want your agency to survive, curiosity is the ultimate skill. Test, adapt, and don’t get too comfortable. That philosophy is why Dan’s agency has evolved from purely video into a full digital offering. On the video side, he had to learn how to let go and empower others. On the digital side, he leans entirely on his team’s expertise. In both cases, growth depends on staying open to new approaches and trusting the right people to execute them. 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.

    27 min
  6. Will AI Really Change Agencies? Why the Human Element Still Wins with Josh Payne | Ep #836

    14 SEPT.

    Will AI Really Change Agencies? Why the Human Element Still Wins with Josh Payne | Ep #836

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you wondering how AI will really change the way agencies work? Will it replace your team, or make them better than ever? Artificial intelligence continues to be at the forefront of most tech conversations, and that’s exactly why agency owners can’t afford to ignore it. Today’s guest believes the real future of AI in agencies isn’t about replacement—it’s about augmentation. Humans bring the high-leverage ideas, AI scales the execution, and the magic happens in the collaboration between the two. That’s why he challenges his team to master a skill first—understanding every step—before delegating pieces of it to AI. By doing so, they not only achieve stronger results but also gain the ability to explain, teach, and refine the process. For agencies, this thoughtful integration turns AI from a threat into a powerful accelerator. Josh Payne is a serial entrepreneur and the founder of Coframe, which helps businesses continuously optimize their digital experiences. Before that, he co-founded Autograph, scaling it to unicorn status within just over a year, and previously sold his first company, AccessBell, to India’s Tata Group. A Stanford AI researcher and occasional lecturer, Josh has blended tech, entrepreneurship, and big-name partnerships into a career full of lessons that agency owners can apply to their own journey. In this episode, we’ll discuss: The power of just asking. Should we be worried about AI? Why the human element still wins. When AI shows empathy. 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. Building Big, Fast (and What Comes After) Josh’s first exit was AccessBell, acquired by Tatai Group. Then came Autograph, the NFT platform co-founded with connections in the entertainment industry that quickly attracted celebrities and athletes like Tom Brady. The company went unicorn in about a year, proof that timing, partnerships, and execution can fuel explosive growth. But Josh is quick to admit that pace sets a dangerous bar. When he launched Coframe, progress felt slower. The natural question arises: why am I not going as fast as I did last time? For any agency owner who’s had one “big win,” the fear of never matching that level again is real. For Josh, it comes down to stop chasing vanity metrics and focusing on the real value you’re creating. The long burn, when tied to a larger vision, often builds a stronger foundation. The Power of Just Asking One of the best stories from Josh’s Autograph journey was how Tom Brady got involved. It was a simple conversation, made possible because a co-founder’s family knew Brady. They took a shot, asked for a call, and suddenly, an NFL legend wasn’t just an investor—he was a co-founder. They were, of course, very lucky, but the lesson for Josh was that you’ll never land your dream client (or partner) if you don’t step up to bat. Too many agencies convince themselves certain clients are “out of reach,” when in reality, decision-makers are more approachable than you think. Even the busiest people have time for the right conversation if you show up as a person, not a pitch machine. Separating Yourself from Your Business Identity With all these exits, Josh is still struggling with the identity crisis that comes with selling or stepping away from a company. Like Jason back when he sold his agency, Josh felt like he’d sold his soul and is still wrestling with how to separate being a tech founder from just being Josh. Your business is not your identity, as performance coach Todd Herman (the guy behind Kobe Bryant’s “Black Mamba” alter ego) helped Jason understand. You’re not an “agency owner” by identity. You’re a creator, innovator, and strategist. Those traits travel with you into whatever you do next. Lose the label, keep the essence. Fighting the Metrics Spiral Every agency owner knows the feeling: dashboards screaming that you’re 30% down from last month, the creeping panic that you’re “slipping.” Josh admits he’s guilty of chasing these vanity metrics too, and it’s exhausting. The problem is that short-term sprints cloud the long-term vision. But focusing only on the long-term isn’t right either. You can’t sit back dreaming and stop executing. Josh calls it a balance game. Some days require in-the-weeds execution. Other days call for pulling up to 30,000 feet and resetting the vision. And finding ways to get into that higher-level thinking state is crucial. Finding Flow and Big Picture Clarity One of Josh’s surprising hacks for perspective is the float tank, a sensory deprivation chamber where you float weightless in silence. He describes it as being suspended between sleep and wakefulness, giving him the clarity to see the forest instead of the trees. For him, a float every couple of months resets his ability to think deeply. This lucid dreaming state allows him to consciously control his thought process, which is hard to do on a day-to-day basis. There are different ways to achieve this “flow state” like flying planes or running, where focus on the task at hand frees the brain to process ideas in the background. The lesson for agency owners is that you need intentional “out of the weeds” time. Whether it’s floating, running, or flying, find your version of the float tank. Should We Be Worried About AI? Where is AI really going, and should agencies be worried? Josh approaches the subject with cautious optimism. He admits there are possible negative outcomes—whole essays have been written about the risks—but he believes society still has control of its destiny. Governance, adaptation, and human ingenuity will help us navigate the “intelligence explosion” ahead. For agency owners, that perspective matters. The fear-driven narrative (“AI will replace us all”) misses the more useful question: how do we adapt to stay ahead? Josh’s view is that AI will become a force multiplier, but only for those who deeply understand their craft first. At Coframe, he leads his team with the mantra: “first we are artisans, then we are automators.” Josh encourages his team to master processes as humans before trying to automate them. An artisan, he says, is someone who not only performs a task with taste and skill but can also teach it to an apprentice. If you can teach it, you can usually train AI to do it too. This is a powerful framework for agencies. Too many people treat AI as a magic shortcut, asking it to “do the thing” without knowing what “the thing” really requires. But if you’ve built the human expertise first, AI becomes like a hyper-capable apprentice, great at code generation, design variations, or crunching vast amounts of data, but still lacking the higher-level strategy and creative ideation that only humans can bring. Why the Human Element Still Wins Lots of people are already trying to launch “AI-only agencies.” This is a mistake. Clients don’t just want data or deliverables; they want connection, guidance, and trust. Even as AI accelerates execution, the human side, like the ability to understand a client, guide their decisions, and translate insights into strategy, remains irreplaceable. This is especially true when clients don’t know what to ask. Tools may say, “Ask me anything,” but most business owners don’t even know where to start. That’s where the agency earns its keep: by framing the right questions and then leveraging AI to deliver smarter, faster answers. AI Limitations on Emotion and Empathy Empathy remains the most valuable and, so far, irreplaceable element that AI cannot afford clients, and where human intervention continues to be necessary. However, as these models get more and more aligned, clients are starting to see cases where the AI is able to show empathy for your situation. For instance, Jason recently tested AI with his own medical challenges. After foot surgery complications, he uploaded photos of his wound to an AI tool and was surprised at how sympathetic the responses felt. It wasn’t just giving data—it was offering encouragement, warnings, and even emergency advice when he tested it with old images. Josh had his own example: experimenting with fasting while using AI to predict weight loss. The model gave estimates but also warned him about the risks and refused to encourage unsafe behavior. Modern models are being trained not just for accuracy but to reflect human values, to ensure they’re aligned with human interests. Balancing AI Alignment With Performance This fine-tuning process with newer AI models makes them more positive and empathetic. But there’s a trade-off: aligned models can lose some raw performance on benchmarks. For agencies, this means two things: AI tools will continue evolving in personality and usefulness. The best results will still come from humans who know how to wield them—pairing empathy, strategy, and creativity with AI’s speed and scale. 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
  7. 10 SEPT.

    Why Agencies Must Lead With Strategy (Not Just Execution) With Pete Caputa | Ep #835

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you stuck acting like an order taker instead of leading your clients with strategy? If you want to grow an agency that survives the competition, you need to do more than deliver pretty websites or manage ad budgets. You need to lead with strategy, prove it with data, and guide your clients through the journey—not the other way around. Too many agencies are still making decisions based on “gut feelings” instead of data, which is why today’s featured guest is tackling exactly that problem—making it easier for everyone in a company to use data daily, so decisions are grounded in reality, not instinct. Pete Caputa is the CEO of Databox, a business intelligence platform built for small to mid-market companies that makes data adoption simple across teams. Before that, Pete spent nine years at HubSpot, where he famously launched and scaled the agency partner program—now responsible for billions in revenue. But Pete’s journey didn’t start in SaaS boardrooms. He began as an engineer, dabbled in early 2000s web apps after learning to code, and struggled through the grind of bootstrapping. his own ventures. A key pivot came when he connected with sales coach Rick Rober, who helped him sharpen his sales chops. That path eventually led him to HubSpot as the fourth sales rep and later, the architect behind the company’s groundbreaking agency channel. In this episode, we’ll discuss: Creating the HubSpot Agency Partner Program. Why agencies need to lead with strategy. AI as the new strategic edge. Selling strategy as a service. 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 Birth of the HubSpot Agency Partner Program Early HubSpot sales conversations looked familiar to many agency owners: lots of free education, lots of excitement… and lots of ghosting. Agencies wanted to roll HubSpot out to their clients, but deals rarely closed. Pete recognized the deeper problem —agencies were stuck in project-based work and living on the cash flow rollercoaster. So he set out to teach agencies to package ongoing retainers instead of chasing one-off projects. That simple but powerful shift unlocked stability and scale. Agencies suddenly had recurring revenue, longer-term client relationships, and the ability to deliver compounding value. HubSpot, of course, became the backbone of that service delivery. What started as a scrappy idea became a multi-billion-dollar channel—and one of the most successful agency programs in SaaS history. Leaving HubSpot As HubSpot scaled, so did its internal politics. Pete found himself in the middle of a growing conflict between the direct sales team and the partner channel. Instead of collaborating, the two operated like competing businesses, often clashing at the deal level. Pete saw a solution, but realized implementing it would be painful in company scaling that fast. He eventually stepped away, even though he was responsible for nearly 40% of HubSpot’s revenue at the time. “It got harder to get things done,” he admitted—proof that what works in a startup culture doesn’t always survive as companies mature. The Evolving Challenges for Agencies Back in the early 2000s, agencies had to convince clients digital marketing was worth investing in. SEO, social, and funnels were foreign concepts for most businesses. Agencies had to sell belief before they could sell retainers. Today, the problem isn’t buy-in—it’s competition. Businesses now see digital as essential, but agencies are often commoditized into executing tactics. Instead of being trusted advisors, many find themselves replaceable—either by freelancers, in-house hires, or other agencies that “do the same thing cheaper.” The risk is clear: if you’re not leading clients strategically, you’re just a vendor waiting to be swapped out. Agencies Need to Lead With Strategy Most agencies claim to do strategy, but really, they only use it to justify selling a tactic. Redesigning a website? They’ll run some quick competitor research. Launching content marketing? They’ll whip up a persona doc. But that’s not strategy—it’s sales collateral. Pete is now working on a framework he calls Predictable Scale. It starts with true strategy: competitive research, customer research, defining vision and mission, and setting clear objectives. Only then do tactics come into play. Most agencies don’t put these together in the right sequence and, as a result, get pushed in to executing tactics. For agencies, this is the key to breaking out of the execution box and earning a permanent seat at the table. AI as the New Strategic Edge These days, agencies can leverage AI to accelerate strategy and client service. It can be as simple as using AI to run a SWOT analysis, refine your brand voice, mission and vision, and then taking all the data and use it to create a custom GPT you can run to generate client-facing plans. One mastermind member, Chris Dwyer, took this to the extreme by building a board of AI advisors (finance, marketing, sales, and acquisitions) and saw incredible growth as a result. Pete’s team has also dabbled in this use of AI and created a custom GPT called Pete GPT. They feed in customer interviews, surveys, and Pete’s own writing so the tool can generate content in his voice. Beyond content, AI is speeding up product feedback loops. By connecting call transcripts, chat logs, and support tickets, his product team can instantly spot customer needs and prioritize features—a process that used to take weeks of interviews. Pete also has an AI agent that handles about 50% of his agency’s conversations with prospects and clients, with a customer satisfaction score of 70% so far. For agencies, the message is clear: if you’re not already embedding AI into your workflows, you’re falling behind. Onboarding and Client Retention Still Matter Most Not everything should be automated, however, especially when it comes to onboarding. Onboarding can make or break a client relationship in the first 60 days. Too many agencies rely entirely on Zoom and automation, missing the opportunity to build true connection. “No one meets with clients in person anymore,” he said, and it’s costing them. Some of the most successful agencies in Jason’s mastermind make it a priority to visit new clients in person during the first quarter. That small gesture builds trust, creates deeper bonds, and makes it much harder for clients to churn later. With competition as fierce as it is, going the extra mile in onboarding may be the simplest competitive advantage agencies can claim. Selling Strategy as a Service Pete wrapped up the conversation by introducing Databox’s new program for agencies: business intelligence as a service. Until now, most agencies used Databox to report on campaign performance. But Pete sees a bigger opportunity—helping agencies package BI consulting as a strategic service. Instead of being the vendor that just improves ad ROAS or runs SEO reports, agencies can step up as partners who improve an entire company’s performance. That means quarterly reviews looking not just at marketing metrics, but at sales, ops, finance, and customer success data too. For agencies tired of being “order takers,” this is the chance to finally sell strategy over tactics—and get paid for 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.

    23 min
  8. 9 SEPT.

    Order-Taker Agencies Are Dead. Here’s How to Survive AI

    Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training If your agency is still saying, “Sure, we can do that” to every client request, you’re already in trouble. AI isn’t coming—it’s here. And it’s gunning for the order takers. The agencies that survive won’t be the button pushers. They’ll be the problem solvers. The strategists. Let’s break down why the old “yes to everything” model is dead—and what to do instead. The Old Way: Execution = Value Back in the day, clients would come in with half-baked ideas, you’d build what they asked for, send an invoice, and move on. That worked when execution was hard and specialized. But now? AI can crank out ad copy, designs, blog posts—even full websites—in under 30 seconds. If your agency’s value is tied to deliverables, you’re already replaceable. The New Way: Sell Outcomes, Not Tasks Here’s what AI can’t do: Diagnose the real problem. Challenge assumptions. Build trust and sell a bigger vision. That’s your edge. Strategic agencies don’t sell websites or ads anymore. They sell clarity. They sell outcomes. They lead the client to where they actually need to go. Think about surgeons or lawyers. They don’t ask, “So what do you want me to do today?” They diagnose. They prescribe. They lead. Great agencies do the same. Real Proof: Owners Who Made the Shift Derek was stuck running a 7-figure agency that was plateauing. He and his team were working themselves into the ground for less and less money. Once he niched down and repositioned as a leader in his space, everything changed. Within a year, he scaled to eight figures. Jack almost shut down his agency before using the Agency Playbook to get clarity, reposition, and dominate his niche. Today, he runs a multi-million-dollar business. Carl stopped “doing” and started leading. Using our Foot in the Door approach, he landed a $100K cash deal plus a 20% royalty stream. These aren’t outliers. They’re agency owners who stopped being order takers and started being authorities. How to Make the Shift Without Burning It All Down You don’t need to fire all your clients and start from scratch. You just need to change how you show up. Stop reacting. Start leading. Don’t ask, “What do you want?” Instead, say, “Here’s what you need, and here’s the proven process to get it.” Get paid for clarity. The Foot in the Door (FITD) system shows you how to charge $2,500+ just for the initial strategy session. Because clarity is valuable—and it positions you as the authority from day one. Audit your model. If you’re stuck or unclear on what to fix next, the Agency Blueprint gives you a custom diagnostic so you know exactly where to focus. Ready to stop being a doer and start being an advisor? Grab the Foot in the Door System here and start getting paid just to pitch. Or if you’re not sure where the gap is, grab your Agency Blueprint here.

    5 min
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À propos

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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