Jason Swenk
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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.
Based on 6 episodes we listened to · September 2026
Jason Swenk turns agency growth problems into concrete conversations about ownership, operations, positioning, automation, and the limits of founder-led management.
Jason Swenk keeps the conversation close to the operating decisions behind a digital agency. His guest interviews move quickly from personal history into questions about acquisitions, project-based revenue, client reporting, automation, delegation, brand differentiation, and the…
Jason Swenk draws a fist-sized circle around the work he wants; your calendar gets nervous.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A hiring story built around a simple boat-and-road-trip test for fit.
Melanie Robinson frames hiring as a test of character after an agency has already paid for the wrong choices. Her boat-and-road-trip example gives the advice its clearest shape: look for people who share core beliefs, show up for others, and are not only looking out for…
A practical look at selling an agency to someone already inside the business.
The episode takes up a familiar turning point for agency owners: when an employee-led exit starts to look like the right move. Natalie Henley and Jason Swenk keep the focus on timing, showing why a team-member buyout can work best before the business is already under strain, and…
A grounded reminder that agency owners need boundaries, not more hustle.
This episode follows Ingrid Schneider, founder and CEO of Staying Your Lane and founder of Train In Your Lane, as she talks about building an agency without letting it swallow the person running it.
Differentiation here is treated as a practical discipline, not just a slogan.
The episode treats branding and differentiation as a working sales tool, not a slogan. David Brier comes across as the kind of person CEOs call after too much money has already been burned, and the conversation keeps coming back to the same useful point: be direct, qualify…
A blunt reminder that agency collapse and self-belief can sit in the same room.
Cliff Skelliter's story is at its best when it lingers on what follows after an agency partnership falls apart: trust takes a hit, money is still owed, and a creative founder has to reckon with his own ability to sell, connect, and handle the business side.
A practical look at agency acquisitions, valuation, and the risk of overpaying.
Kimberly Eberle keeps the discussion practical, moving through five acquisitions and spelling out why one deal did not close. It stays close to the real work of pricing a purchase, from stripping out salaries and other non-recurring costs to testing how certain the forecast…
A human-first agency conversation that keeps returning to relationships, networking, and what actually drives the business.
This episode follows Marissa Rosen and Climate Social, the micro-agency she founded in 2015 around climate action, sustainable business, and social media.
A founder-led agency works best when the business is built around the owner and the way they work.
Brian Franks makes a simple, convincing case for building an agency around the owner instead of forcing the owner into a generic mold. Wear Eagles Dare comes through as a creative collective built on branding and storytelling, with a small core team and a business that still…
Rob Walling on bootstrapped SaaS growth, plateaus, and exits — with founders who lived them.
Abbey Ashley's playbook for turning your job skills into a virtual assistant business.
Naval Ravikant on epistemology, startups, and crypto, from David Deutsch to Vitalik Buterin.
Alex Theuma interviews SaaS founders and investors on scaling to $10M-plus ARR.
Guy Raz traces founders' origin stories and fields live advice-line calls from entrepreneurs.
Alex Blumberg interviews guests like Megan Phelps-Roper and Shane McAnally about failure and reinvention.
Jason talks with Marissa Rosen, founder of Climate Social.
Jason Swenk talks with Gilad Bechar, CEO and founder of Moburst, about how a digital agency with five acquisitions and clients like Microsoft, Google, Uber, and Samsung is reorganizing around AI.
Dave Arato of Lexicon Legal Content says AI changed legal SEO in December 2022, when ChatGPT could generate in 30 seconds what once took his team an hour or two.
Austin Armstrong says he spent 21 years in social media marketing, including 12 years in agency work, before burnout pushed him toward AI SaaS and his tool Syllabi.
Taylor McMaster says she built Dot & Company for a full exit after the first year, not as a lifestyle business, and deliberately removed herself from sales, operations, fulfillment, admin, and finance.
Jason Swenk and Eli Rubel dig into the messy, practical side of agency pricing.
Brian Hanson says Rocket Pilots is going “AI native,” and he ties that shift to folder structure, custom GPTs, Google Gems, and required Claude use inside the agency.
The host brings back Ben Gaddis to talk through agency buying from the buyer’s side, including what it looks like when a business has already been sold to private equity.
Brian Franks introduces himself as the founder of Wear Eagles Dare, a creative collective built around branding and storytelling.
Jason Swank brings Nathan Jensen back to talk about how agencies and service businesses can keep from getting stuck in old habits.
Jason talks with Michael Boychuk, founder and creative director at DNA in Stone in Seattle, Washington.
Terry Zelen talks through how his Tampa agency is thinking about SEO and LLMs as client-facing opportunities.
An agency growth pitch opens the clip.
Natalie Henley joins Jason Swank to talk through an easy-to-miss agency exit: selling to a team member.
Alicia Disantis shares her journey from charging $200 for design work to running a 15-year-old agency, focusing on strategies to educate clients on the true value of creative services.
Ingrid Schneider shares her journey from burnout to building two successful agencies, discussing how personal healing, empathetic leadership, and strategic AI integration transformed her business.
Scott Desgrosseilliers discusses the challenges of using AI for marketing data analysis, revealing that AI often gives confident but wrong answers due to issues like lacking time awareness and misinterpreting campaign intentions.
Host Jason Swenk interviews branding expert David about why most agencies sound the same and how to differentiate.
Cliff, a creative agency owner from Canada, shares his journey from accidental entrepreneurship to navigating broken business partnerships.
Jason Swenk interviews Larissa Wurstiek about how she pivoted her jewelry-focused marketing agency to email/SMS marketing for women-owned e-commerce brands when her niche stopped working.
Eric Weidner discusses how AI is transforming web development and agency work, comparing tools to 'drunk interns' and emphasizing that clients want AI expertise for better results, not just cost savings.
Nital Shah, co-founder of a 700-person digital agency, discusses scaling challenges, including COVID revenue drops, profitability strategies, and using frameworks like Scaling Up for team alignment.
Joy Hawkins, owner of Sterling Sky, discusses surviving Google updates and AI disruption while scaling her remote local SEO agency.
Host Jason Swenk interviews Filip Ludović, founder of a digital communications agency in Brussels that specializes in helping organizations influence EU policy.
This episode compiles insights from top agency owners interviewed in 2025, focusing on adapting to AI, improving efficiency, and building strong client relationships.
Kimberly Eberle, founder of The Motion Agency, discusses her journey from being fired to building a multi-office agency, including insights on acquiring agencies larger than her own, the importance of culture in mergers, and valuation challenges.
Andy Crestodina shares lessons from 25 years running Orbit Media, including a toxic partnership that required mortgaging his house to resolve, and how hiring a CEO freed him to scale content marketing.
Tom Snyder shares his 30-year agency journey, including a failed merger during the dot-com crash and 9/11, leading to reinvention as Tourvera.
Kasim Aslam explains how Answer Engine Optimization (AEO) differs from traditional SEO, emphasizing schema markup and social mentions over link building.
Charlie Clark, an SEO agency owner, discusses why mid-sized retainers ($3-6K) are more profitable than large enterprise clients, sharing insights on pricing, productization, and trust-building.