Smart Agency Masterclass With Jason Swenk: Podcast For Digital Marketing Agencies

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Most agencies don’t make it 25 years but Bill Swanston’s has. From surviving 9/11 to leading a 30-person team through COVID, Bill shares how Bosun (formerly Frederick Swanston) adapted, learned to love KPIs, empowered their team, and even pulled off a successful rebrand. His story proves you can survive the toughest agency seasons and come out stronger—if you track the right numbers, avoid “superclient” risk, and learn to truly let go. What You’ll Learn Why resilience (not just growth hacks) is the real agency survival skill How ignoring KPIs almost cost the agency big—and how to avoid that mistake Why letting go of control is the only way to grow past founder-dependence What a rebrand really signals about an agency’s maturity and leadership shift The hidden dangers of relying on a “superclient” Key Takeaways Keep overhead light in uncertain times—it gives you room to maneuver when crises hit. Track

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

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, municipalit

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 mar

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 f

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 brand

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

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. B

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 edg

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Which growth drivers are fueling your agency right now? For today’s featured guest, the answer is clear: thought leadership. It’s the single biggest driver consistently bringing his agency the best opportunities. While it can be difficult to separate genuine impact from vanity metrics, the deliberate effort to position both himself and his agency as industry experts has proven invaluable for growth. But building that kind of authority doesn’t happen by accident. It requires intentional work—stepping onto stages at conferences, showing up in interviews and podcasts, and, just as importantly, encouraging your team to create and share content of their own. In this conversation, he breaks down the strategies that help expand thought leadership beyond the founder, and why agency leaders must remember: expertise is a long game, one that compounds over time to deliver lasting results. Chris Long is the VP of Mar

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you an agency owner chasing the $1 million mark, believing that milestone will finally transform your business? Today’s featured guest once felt the same way—until he got there and discovered it was all a myth. Hitting seven figures looked like success on paper, but behind the scenes he was burning himself out just to keep things afloat. In this episode, he reveals the processes that helped him escape no man’s land, the critical lessons he learned about hiring, and the one thing he would do differently if he had the chance to start over. Justin Rashidi is the CEO and co-founder of SeedX, where he leads data-driven marketing strategy and operations. Justin never planned to start an agency, but what started as a tutoring gig in New York soon turned into a full-blown business. After getting past some common agency growth hurdles, he’ll share what he’s learned on overcoming no man’s land, hiring, why he t

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Is your agency’s strategy diversified enough to withstand sudden algorithm changes? Today’s featured guest—an SEO veteran—learned this the hard way. While he focused on client work, his own website grew outdated. Then one Google update hit and overnight his agency lost 80% of its organic traffic, its main source of leads. The agency eventually recovered, but not without leaving him with a powerful lesson: always invest in the three pillars of growth. In this episode, he shares his chaotic first encounter with SEO, the biggest lessons from a long career in the industry, and the “superpower” that helps him better understand and adapt to algorithm shifts. Chris Raulf is the founder of Boulder SEO Marketing and Chris Raulf SEO & AI Consulting. With decades of experience in SEO, dating back to before Google was even called Google, Chris specializes in hyper-focused SEO and content marketing strategies. He’

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Would you ever run two agencies at once? What if splitting your brand was the smartest way to protect and grow both? Today’s featured guest spotted a booming opportunity in a regulated market—but knew that advertising those services alongside his work for conservative and tech clients could hurt his existing agency. His solution? Launch a separate brand. The move paid off as the regulated market surged during the pandemic. He shares what it’s like to manage rapid growth, why he built a true people-first culture from day one, and how he stays optimistic even when agency life gets messy. Greg Peters is the founder of 4B Marketing and Hybrid Marketing in Denver, Colorado. 4B focuses on tech, energy, and government sectors, while Hybrid serves regulated markets—most notably the cannabis industry. A former tech sales pro turned serial entrepreneur, Greg’s journey into agency ownership may have been accident

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Most agency owners don’t wake up dreaming about selling. You want freedom, better clients, and to stop living in Slack at 2 a.m. But here’s the truth: The same moves that make your agency attractive to a buyer are the ones that give you freedom as an owner. I built and sold an 8-figure agency and bought 10 more and now I’m sharing 8 elements of a sellable, scalable agency. Whether you ever sell or not, these are the foundations that make your shop stronger. Let’s break them down. 1. Stop Being the Accidental Owner Most of us stumbled into agency life. That’s fun—but long-term it’s not a strategy. You’ve got to shift from “operator” to agency CEO, and that means: Setting and communicating vision (over and over). Coaching your leadership team, not everyone. Knowing your numbers. Being the face of the agency. Building strategic relationships. When your team knows where you’re going, you stop bein

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What happens when the agency you’ve built is just… stuck? Or when you hit a revenue ceiling, lose a major client, and start wondering if you’ve been playing the wrong game entirely? Those moments either break you or become the pivot points that redefine everything. In this episode, you’ll hear from an agency owner who’s lived through the grind growing his agency from scratch, riding out recessions, choosing a niche that would help him get out of “no man’s land”. He’ll discuss the strategic bet that broke through plateaus, why he still refuses to hire a COO, and the million-dollar risk that could have sunk him but ended up being a worthwhile bet on his vision. Alex Membrillo is the founder and CEO of Cardinal Digital Marketing, a 100-person specialist agency in healthcare performance marketing. Based in Atlanta, Alex launched Cardinal 16 years ago fresh out of college driven by equal parts ambition and

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you growing your agency with the goal of selling it one day? More importantly, are you taking the right steps now to ensure it’s actually worth what you think it is? Today’s featured guest has built and sold multiple agencies over the years, gaining hard-earned insights into the process. He shares what you need to know to prepare your agency for sale, the potential pitfalls and opportunities with non-competes and earnouts, and whether hiring a broker is really worth it. If selling your agency is on your horizon, or even just a long-term possibility, this episode is packed with practical advice to help you maximize your valuation and avoid costly mistakes. Sean Hakes has been building and selling digital marketing agencies since the early 2000’s back when ‘SEO’ wasn’t a household term and websites were still coded in tables.. He’s grown agencies from small side hustles into multi-million-dollar oper

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What happens when you stop chasing $30K projects and start solving real problems for smaller clients in a way that actually works? Today’s featured guest had been building $32,000 websites for mid-market companies. On paper, it looked like success. But in reality, he felt stuck—unfulfilled and back in a corporate-style grind that didn’t align with the kind of work or life he truly wanted. When he took a step back, he realized something important: the clients he really wanted to serve were already reaching out. These were smaller, $300K businesses with many of the same challenges agencies see across the board—but without the bloated complexity. So he made a bold pivot. He simplified his offer, created a productized service, and returned to his roots—helping people in a way that felt meaningful, scalable, and sustainable. The result? Less stress, more impact, and a business model built around freedom, no

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you stuck chasing new clients while ignoring the goldmine in your past customer list? Does your agency feast on projects but starve for predictable revenue? Today’s featured guest knows what it’s like to hit a growth ceiling and being tired of the one-and-done client hamster wheel. He shares how he pivoted his agency after becoming a HubSpot partner, why he turned to project-based work after customer habits changed following the pandemic, and how he got out of the dreaded “no man’s land”. Eric Baum is the CEO and founder of Bluleadz, a HubSpot Onboarding and Implementation Agency dedicated to transforming the way companies market, sell, and service their customers through the power of the HubSpot platform. He’ll discuss his cash flow challenges, pricing mistakes that almost tanked the business, and how EOS helped him escape “no man’s land.” If you're stuck in the fulfillment hamster wheel or scalin

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you still running your agency like it’s 2010? You know the setup: rigid roles, top-down management, a “just get it done” culture. If that sounds like your agency, chances are you’re the bottleneck. You’re stuck in the weeds, making every single decision, dealing with high churn, and wondering why output is low despite how hard everyone’s working. This is the story for most agency owners at the 7-figure stage. But the agencies scaling fastest today have evolved—and we’re breaking down exactly how. Why Most Agencies Get Stuck Most agency owners didn’t plan to be CEOs. You were good at strategy, sales, design, or delivery. Then suddenly—boom—you’re the boss. Now the team looks to you for every decision, every review, every answer. The problem isn’t your team. It’s the lack of vision. When there’s no clear direction, your team can’t lead themselves—because they don’t know where the hell they’re going. Onc

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Are you a CEO still caught in the weeds of day-to-day operations? If so, you're not building a truly scalable business. Today’s episode is here to help you shift that mindset. Our featured guest is a CEO who has grown his agency by focusing on smart leadership—prioritizing culture, developing strong management structures, and intentionally making himself less essential to every meeting. Like many agency owners, he once believed he had to outwork everyone to prove his worth. But over time, he discovered that the agency performs better when he leads with vision instead of constant presence and that CEOs don’t need to be grinding to be effective. In this conversation, he shares how he came to that realization, what it’s meant for his agency’s growth and client success, how he built a trusted A-team, and more. Kevin Miller is the co-founder and CEO of Gr0, a performance marketing agency that’s exploded from s