Smart Agency Masterclass Podcast with Jason Swenk
Bi-weekly interviews, strategy, and advice for building your marketing agency the smart way.
The popular agency podcast has just turned 12 years old and covers everything from starting a successful agency to selling your agency.
#1 Agency Leadership Podcast. Check Out Our Past Guests.
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Seth Godin
Best selling Author of Purple Cow, This is Marketing, Linchpin, Permission Marketing
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Guy Kawasaki
Guy Kawasaki is the chief evangelist of Canva and former Apple chief evangelist
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Gino Wickman
The creator of the Entrepreneurial Operating System (EOS) and author of Traction.
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Neil Patel
Founder of CrazyEgg, Kissmetrics, and other multimillion dollar companies
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![Uri Levine]()
Uri Levine
Co-founder of Waze
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Joey Coleman
Recognized for his expertise in customer retention & enhancing client loyalty
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Mike Michaelowicz
Best-selling author of Profit First and Clock Work
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Amy Porterfield
Renowned online marketing expert and educator
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Pat Flynn
The leaders in the podcast space
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Jay Baer
Best Selling author of Talk Triggers, Hug Your Haters, and one of the best speakers
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Todd Herman
Coach to Elite pro athletes, leaders, and public figures
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Dan Martell
Author of Buy Back Your Time. Influential coach in SaaS startups.
Your Agency Can’t Scale Past the Role You’re Stuck In with Dave Benton | Ep #901
How can you build an agency that outlasts your involvement in it? And what happens to your identity when you finally make that shift?
Over the course of 22 years, today's featired guest grew a one-person freelance operation into a full-service digital agency doing eight figures and then sold it. In this conversation, he'll unpack the real lessons from that journey: the painful transitions between operator, manager, and architect, the hiring decision that finally unlocked his ability to step back from the work he loved, and why the question isn't just who you need on your team — it's who you need to become.
The CEO Trap: Why Founders Either Check Out or Can't Let Go with Matt Nelson | Ep #899
Does growth break agencies or does it expose underlying issues? It’s a common thing. Even with momentum, scrappy decisions, loose roles, and unspoken agreements eventually become the very thing that holds the business back. And by the time it’s visible, it’s no longer a small fix. It’s structural.
Today’s featured guest pulls back the curtain on that transition.
How to Build an Agency That Doesn’t Depend on You with Ted Harrison | Ep #897
Are you struggling to scale your agency or are you unknowingly the thing holding it back?
At what point does your growth stop being a systems problem and start becoming a leadership one?
Today’s guest shares what it to break through those ceilings.
After scaling quickly off the back of a strong network, he made the critical decision to systemize everything before growth turned him into the bottleneck. By leveraging documentation in a smart, intentional way, he built a foundation that allowed the agency to grow without everything running through him.
In this conversation, he unpacks the realities of working with enterprise clients, the often uncomfortable shift from operator to CEO, and why—despite all the noise, AI is actually increasing the need for human judgment, taste, and leadership, not replacing it.
Why Your Agency Can’t Scale Until You Stop Being the Doer with Matt Kovacs | Ep #893
Have you ever wondered how to strike that balance between managing your team and ensuring success for your clients? Today's featured guest is here is talk about what it actually takes to evolve from doing the work to building a team that can win without you.
The conversation cuts through common agency myths, like hiring better clients first or relying on RFPs, and instead exposes the real drivers of growth: team strength, leadership evolution, and structural leverage.
Why Doing More Is Holding Your Agency Back (And What to Do Instead) with Darby Copenhaver | Ep #892
In this rapidly evolving agency landscape, uncertainty has become the norm rather than the exception. From overwhelming decision paralysis caused by AI and doubts on how to move forward with clarity, owners need to adapt to constant change, identifying true bottlenecks, evolving their role, and simplifying systems to scale effectively.
Today’s featured guest is the first point of contact for agency founders experiencing these very struggles. As someone very in tune with the issues founders face, he’ll talk about the steps they need to take to prevent becoming a bottleneck that gets in the way of their own growth and share why growth isn’t about doing more; it’s about becoming something different.
Why Project-Based Agencies Feel Profitable But Aren’t Sustainable with Michael Boychuk | Ep #887
Are you winning exciting projects but still feeling exhausted at the end of every quarter? Does your agency look successful from the outside, yet feel fragile or chaotic behind the scenes?
For most agency owners, the real struggle isn’t creativity. It’s sustainability. Landing big projects isn’t usually the hardest part. The real challenge begins after the win, when you have to deliver consistently, protect your margins, manage your team, and somehow still have the energy to lead.
What It Takes to Scale a 700-Person Agency Without Losing Your Mind (or Margin) with Nital Shah | Ep #870
How big do you actually want your agency to become? Does the idea of running a massive team sound exciting or completely exhausting? For many agency owners, scaling feels less like growth and more like trading freedom for complexity.
Scaling an agency isn’t about hustle. It’s about surviving the moments that almost break you, building systems that actually work, and accepting that what got you here won’t get you there. Today’s featured guest understands that running a big agency is about structure and leadership. He’s grown a global agency to 700 people without losing profitability, sanity, or culture and now he’ll unpack the hard-earned lessons that most agency owners don’t think about until it’s too late.
How to Choose the Right Agency Niche and Stick With It Through Uncertainty with Filip Lugovic | Ep #868
Starting with a clearly defined niche can make all the difference when you’re landing your first clients and deeply understanding that niche can carry you through the toughest seasons of agency life. Today’s featured guest built his agency on exactly that foundation.
Before launching his firm, he spent years working as a consultant for governments, UN agencies, and the European Commission. Along the way, he identified a clear gap in the market.
That expertise proved invaluable during the pandemic. While uncertainty hit many agencies hard, he trusted his understanding of the space and chose to weather the slow months, confident the work would return. His patience paid off as demand surged later in the year.
He’ll share the lessons learned from more than 20 years of building and running a thriving niche agency in one of the most political and complex markets in the world—and why focus, patience, and deep domain knowledge remain his greatest competitive advantages.
Why the Most Profitable Clients Aren’t Always the Biggest: Selling Smarter with Charlie Clark | Ep #862
Have you ever felt like enterprise clients were running your agency instead of the other way around? Buried in endless proposals no one reads, forced into rushed timelines, or watching your margins shrink every time a project drags out? Today’s featured guest opens up about how he broke out of that exhausting cycle. Instead of over-delivering just to keep big clients happy, and seeing little return, he made the bold decision to focus on smaller, more committed clients who were ultimately more profitable and easier to build long-term relationships with.
Why a Fortune 500 Marketing Leader Left His Dream Job to Start an Agency with Eric Gray | Ep #860
Would you ever walk away from a “dream job” to start over from scratch? And if you’ve spent years building a career inside big brands, does it ever feel like it might be too late to launch your own agency? Most people talk about leaving their corporate job to chase something bigger. Very few actually do it, and even fewer jump without a parachute. Today’s featured guest is one of those rare ones. After nearly two decades leading social, content, and influencer teams for household brands, he walked away from his so called dream job to start his own shop without any safety net. Today, he calls himself a brand guy who happens to own an agency.
Eric Gray is the owner of Maverick Content Studio, a twelve person, social-first agency for Fortune 500 brands. After a long and successful career in corporate, where he spent eighteen years building high performing social and content teams for companies like Universal Parks & Resorts, Eric realized he did not want the future he saw in front of him. He left Universal with two months of savings and zero clients. His story is a blueprint for leaders wondering whether to leave corporate and build something of their own
Today his team works with brands like Advent Health, Winn-Dixie, and Travel + Leisure, helping them build audience, loyalty, and relevance through social-first content.
About the Show
The popular agency podcast has been around since 2014 and covers everything from starting a successful agency to selling your agency. What makes this podcast a must-listen is Swenk’s background as the founder and CEO of an agency for over a decade. Swenk brings his own experience to the table, besides the expertise of his guests. He mostly covers topics that help growing agencies scale to the next level.
YOUR HOST
JASON SWENK
Smart Agency Masterclass
Jason is a family man who also happens to have created a couple big marketing agencies, helped thousands of agency owners, and had a big agency exit too.
