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.

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.

Jason Swenk Jason Swenk

Why Being a Category of One Is Your Best Defense Against AI Commoditization with Leslie Silverman | Ep #935

Leslie Silverman is the co-founder of Hive 180, a strategic marketing agency based in Colorado that serves expert service businesses including architects, contractors, attorneys, medical professionals, spas, and high-end consultants. She started her career in print media at Condé Nast and Hearst in New York City before eventually co-founding Hive 180 almost by accident. In this episode, Leslie and Jason dig into what it actually takes to stop being a generalist, why individuality is your most durable competitive advantage in the age of AI, and how she rebuilt her agency model around project-based strategic work instead of retainers.

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How to Stop Being the Bottleneck in Your Own Agency with David Khim | Ep #933

David Khim is the co-founder and CEO of Omniscient Digital, a B2B SaaS SEO and content strategy agency based in Austin, Texas. Before starting Omniscient, David was head of growth at People.ai and Fishtown Analytics, and a growth product manager at HubSpot, where he met his co-founders Allie Decker and Alex Birkett. What started as a side consulting project between colleagues turned into a full-time agency — and then required a different kind of founder entirely. In this episode, David and Jason dig into the identity shift that agency owners have to make to actually scale: from operator to architect, from doing to leading, and from proving your value through involvement to trusting your team to execute without you.

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How 19 Years of Niche Focus Built an Agency Where Clients Compete to Work With You with Wendy Covey | Ep #932

Wendy Covey is the co-founder and CEO of TREW Marketing, a strategy and content agency exclusively serving engineering and manufacturing companies. She started the agency in 2008 — during the Great Recession — as a generalist, and within a year or two of niching down, won a Wall Street Journal Small Business Innovation Award. Today, TREW Marketing is 19 years in, and Wendy has stepped fully into the owner role, with a president and leadership team running day-to-day operations. In this episode, Wendy and Jason dig into what it took to get there: the painful business partner buyout, the career path restructuring, and the niche positioning that now has clients convincing Wendy to take them on.

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Stop Setting Goals Until You Ask This One Question with Phil Davis | Ep #931

Phil Davis is the founder and CEO of Tungsten Branding, one of the world's top-ranked naming and branding agencies, and the man behind hundreds of company names including PODS, RallyHouse, and TeamLogicIT. Before Tungsten, Phil ran a full-service ad agency in Tampa Bay for 17 years before hitting an inflection point: he was succeeding by every external metric and miserable at the core of it. In this episode, Phil and Jason dig into the one question that cuts through all the noise of running an agency, why chasing revenue metrics is a trap, and what it actually means to build a business in alignment with what you want.

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From Getting Fired to Running a Thriving SEO Agency with Leo Poitevin | Ep #929

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

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Is Your Best Skill Actually Squashing Your Agency's Growth? with Brett Singer | Ep #923

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

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

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Does Your Agency Sell Work That AI Does for Free? with Tom Lee | Ep #909

Are you still optimizing your agency's content for Google while your clients are getting their answers from AI? Are you charging for the execution that AI is about to make obsolete, while giving away the strategy that commands real fees? Today’s featured guest works with agencies navigating the shift from traditional search to generative engine optimization. He’ll talk about what the Anthropic research actually says about how much of the work agencies do today can be automated, how AI reads content differently than Google does, and the practical steps any agency can take right now to show up in AI-generated answers before competitors figure it out.

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When Growth Isn’t the Goal: Rebuilding for Freedom, Not Burnout with Blake Denman | Ep #806

Have you ever found yourself grinding endlessly, only to pause and think, “Is this really what I signed up for?” Maybe you started your business chasing freedom—only to end up feeling trapped by the very thing you built. It’s a common trap: the belief that working harder and enduring more pressure will eventually earn you the right to enjoy life after a big exit.

But as today’s guest discovered, you don’t need to wait 10 more years to start living. What you really need is a clearer why, a stronger structure, and the right people around you—people who understand your vision and support your growth.

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Boosting Agency Efficiency with the Help of AI Integration with Manish Dudharejia | Ep #768

Are you integrating AI in your agency processes in the most effective ways? What sort of opportunities are you missing by not integrating AI into your agency’s systems and processes? There’s no going back from AI, so you might as well embrace it as it continues to evolve the ever changing agency landscape.

While many agencies have begun incorporating AI tools, numerous opportunities remain unexplored, and the technology's full potential is still emerging. Today's featured guest brings unique insights as an agency owner who has fully embraced AI's transformative power. Through his continuous study and practical implementation of AI solutions, he has gained valuable perspectives on how this technology is fundamentally altering agency operations—from team structures to client expectations. Tune in for practical insights for agency leaders looking to harness AI's potential while adapting to the evolving demands of the digital marketplace.

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From Startup to Sale: Free Yourself from Your Agency with Robert Royer | Ep #750

Are you caught in the challenging "no-man's land" of agency ownership—where growth meets gridlock? Despite years of management experience, today's guest discovered that running a digital agency demanded more than strategic acumen alone. His journey reveals the often-overlooked complexities of agency leadership that can transform an owner's dream into an operational maze.

Although he felt comfortable making the strategic decisions as a manager, as an owner he found himself pulled in countless directions. From juggling legal complications, financial decisions, and HR responsibilities—areas far removed from his core strengths and passion for marketing strategy. In the end, he recognized the only way through was setting up the right processes for the agency to grow without him and ultimate decided to sell. Tune in to learn about building a successful marketing agency and the principles that guide his approach to client service.

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