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

Daniel Moscovitch, the founder of Flooring Pros Marketing, emphasizes the power of niche specialization in digital marketing. He shares his journey from being a generalist to focusing solely on the flooring industry, highlighting the initial challenges and the rewards that came with it. Moscovitch also discusses the importance of clarity in business partnerships and how leveraging AI tools has enhanced his agency's decision-making and efficiency. His story illustrates the value of persistence and understanding client needs in achieving success.

Agencies relying on cheap AI tools may be in for a shock as costs are predicted to soar. The comparison to Uber's pricing trajectory highlights the temporary nature of today's affordability. A successful strategy involves auditing current systems, creating proprietary processes, and enhancing skills for future resilience. While automation can save time and money, documenting workflows is crucial to avoid chaos when change strikes. Smart operators leverage AI effectively, preparing for a market where loyalty and stability could soon come at a premium.

Chris Dreyer, CEO of Rankings.io, shares insights on transforming his legal marketing agency from a humble seven figures to an impressive $30 million in revenue. He emphasizes the importance of data-driven decision-making and key performance indicators for success. Dreyer also explores the impactful role of AI in enhancing client communication and operational efficiency. Additionally, he highlights the significance of in-person meetings for building client relationships and discusses the challenges of leadership in a rapidly growing environment.

Shawn Johnston, owner of Forge and Smith, a Vancouver web agency, shares his journey from print designer to agency founder. He discusses the importance of documenting processes for smooth operations and scaling. Shawn reveals how AI can create a 'digital brain' for agencies, empowering teams and eliminating bottlenecks. He also focuses on optimizing tasks for greater profitability and the value of shifting to value-based pricing, providing actionable tips for agency owners seeking to create more freedom in their work.

Blake Denman, the president and founder of Rickety Roo, shares his journey from trauma to entrepreneurship and the importance of aligning business with personal values. He discusses time management strategies that prioritize fulfillment over mere growth, including time audits and the '£5K task' rule. Denman emphasizes the mental load of entrepreneurship and reveals how AI aids in self-reflection. He encourages agency owners to design their lives strategically, fostering supportive relationships for both personal and professional growth.

Brent Weaver, founder of UGURUS and veteran digital agency leader, shares his candid insights on life after selling his agency not once, but twice. He reveals the emotional rollercoaster of transitioning from an entrepreneur to an executive and how he retained his team during this shift. Brent emphasizes the critical role of human connections in an AI-driven world and warns against treating AI as a gimmick. He also discusses strategies for agencies to navigate the complexities of accountability in client relationships amidst increasing automation.

Pepsi's jaw-dropping $2 billion acquisition of Poppi highlights the power of unique branding. The discussion centers on how agencies can help clients break free from boring, traditional marketing. By using innovative strategies and the 'Hell Yes Framework,' agencies can transform their clients into memorable brands. The conversation emphasizes the shift from being mere vendors to becoming essential partners in brand evolution. It's all about winning by being different in a crowded market, where cultural relevance and storytelling can lead to remarkable success.

In this engaging discussion, Brent Weaver, founder of YouGurus, shares his entrepreneurial journey from building websites as a teen to creating a seven-figure coaching business for digital agencies. He reveals how launching without a complete product can lead to success and the lessons learned from evolving his company. Brent candidly discusses the emotional complexities of selling his business, unpacking the unexpected aftermath and the importance of adaptability in the fast-paced digital landscape.

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What if one bad hire wrecked your agency? What if the red flag you're dismissing tanked your margins? Most agency owners learn these lessons the hard way. But you don’t have to. In this episode, Collin Slattery shares the red flags, hiring mistakes, and leadership shifts that helped him build an agency that’s not just growing—but growing sane. He’s here to share stories that can help you shortcut the pain and build smarter, sooner. From pricing hesitations to over-hiring juniors to waiting too long to fire a bad hire, he brings great insights about what not to do—and what to fix fast. At the end of the day, the goal isn’t just growth—it’s sane growth. Collin Slattery is the founder of Taikun Digital, an agency that primarily focuses on the e-commerce space, doing Facebook ads, Google ads, and creative landing pages for clients. He’ll share his scrappy beginnings, the mistakes that cost him (and taught him), and the non-negotiables he’s learned about red flags and respecting your own time as an agency owner. His strategy now is simple: only do the work that’s uniquely his. Delegate the rest. And when hiring, pay for people who love the stuff you hate. In this episode, we’ll discuss: How to spot sales-process red flags before they cost you. Why hiring friends usually fails—and how to do it right if you must. What to do before a big client leaves—so you’re not scrambling. The hiring mindset that leads to faster, saner growth.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. Starting with $300 and a Canadian Pharmacy Right out of high school—class of ’07—Collin started making money online during what he calls the "Wild West" days of digital marketing. Think bootleg Canadian pharmacies, early Google Ads, and cracked versions of Adobe software. One of his first official clients was a skincare brand called Spa Technologies, which he charged $300 a month to handle “all the web stuff”—from email and SEO to advertising and site updates. He even landed a local government gig in New York early (back when procurement was a little less formal). It wasn’t glamorous, but it was enough to plant the seed for what would eventually become his agency. Eventually, Collin took the boutique route. He leaned into complex client problems and bespoke solutions, found his zone of genius, and grew from there. Hiring Red Flags During the Sales Process One of the most expensive lessons agency owners learn, and one Collin has relearned, is ignoring red flags during the sales process. It’s amazing how anyone can forget to trust their gut when they need the money, but Collin has learned this lesson by now. From clients with unreasonable expectations who ghost meetings to those who show up late or treat your time like it’s optional, he has learned to put a limit. Today, he waits five minutes—max—for a prospect to join a call. If they don’t show, he’s out. Because if someone doesn’t respect your time on the sales call, they’re definitely not going to respect your process, boundaries, or team later on. The biggest red flag for Collin is clients who offload all responsibility. If they’re promising to be your “best client ever” or insisting they’ll deliver everything you need “right away,” it’s worth digging deeper. Of course, clients who are too involved can also be a problem. However, the agency can’t be more invested than they are in their own success. To prevent this, establish a pricing structure where at least 50% of the project is paid upfront, with clear dates for the remaining payments.. This can help irresponsible clients get moving on what they’re supposed to deliver, although Jason shares a story about a client who paid 100% upfront (before kickoff!) but delayed the project by not providing what was promised. That’s why process and payment timelines matter. If you don’t control scope and expectations from day one, you’ll pay for it in time, profit, and sanity. When One Bad Hire Derails Everything Collin’s been on both ends of the hiring spectrum—over-prioritizing skill and under-prioritizing culture fit… then swinging the other way and hiring people he liked without checking if they actually had the skills. Spoiler: Neither approach worked. On top of that, he’s been guilty of stubbornly keeping people too long, thinking he could “fix” them. However, he’s now confident that owners can usually know on Day 1 if they made the wrong hire. Week 1 if you're generous. People usually start with their best foot forward, so if that’s shaky, it’s a red flag. The real game-changer was learning to trust his gut early and cut things off quickly—for everyone’s sake. Hiring Friends? Set Very Clear Expectations Should you hire friends or family? Most agency owners will say no—and Collin would’ve agreed… until one friend hire actually worked out. There were many factors that contributed to this, including expectations, where the agency is at, and the person’s character. The first time he hired his best friend, it was a disaster. The second time, it was a former mentee who had already sold his own agency, knew the ropes, and was a perfect culture fit. They were open, direct, and mutually respectful—and it worked. The lesson? If you do go down the friend/family road, set clear expectations, give both parties an exit ramp, and value the friendship above the business if things go sideways. The Secret to Real Growth: Do Less of What You Hate According to Collin, delegation and self-awareness are the great drivers of his agency’s success. He focused on hiring people to do the things he was either bad at or dreaded doing—even if he was good at them, because chances are someone else loves the stuff you hate doing. That mindset shift allowed Collin to get laser-focused on what he does best—sales, marketing, and solving complex “math problems” for e-commerce clients. Now he wakes up looking forward to work instead of dreading it. When a Big Client Bails, Your Margins Matter More Than Ever Recently, Collin’s agency lost its biggest client temporarily due to the pressures of the new tariffs. Instead of panic, his response was grounded and strategic. He’s built his agency to survive losses like this and encourages agency owners to do the same, by thinking about pricing, hiring, and not sabotaging your own sales engine. Thanks to this mindset, the agency had healthy profit margins baked in. If losing one client sends you into a tailspin, you’re probably not charging enough. You need to build your business in a way that you can survive losses without cutting down. That’s not just about pricing—it’s about operating with margin as a mindset. One of the biggest mistakes agency owners make is hitting pause on sales because things feel good. Collin’s advice is to always be selling. And if capacity is tight, don’t pause—raise your prices. Pro tip: Implement a sliding scale strategy. Every few clients, bump your pricing and track retention. You might find that you’re working less for more. Want to Grow Fast? Hire Ahead of the Demand Let’s talk about one of the hardest lessons agency owners learn: hiring too late. Collin admitted he brought on clients he couldn’t serve well—and paid the price in churn and stress. This year, he’s trying a different strategy by hiring ahead of the demand. And not just anyone—hire senior people. Yes, it’s a luxury. But it’s also how you buy back your time and protect your client relationships. Junior hires sound good on paper—cheap, trainable, full of potential. But they require time and energy you may not have. As Collin explains, the real value of a senior hire is autonomy because they can own it from day one. ”At the end of the day, if you don’t build margin into your agency, one bad month can wipe you out.” 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.

Brandon Na, the founder of Seattle Organic SEO and venture capital expert, emphasizes that simply delegating AI tasks could jeopardize agency success. He draws from his experiences in SEO and corporate environments, revealing how hands-on leadership during AI adaptation fuels innovation. Brandon highlights the shift from traditional Google searches to AI tools in digital marketing, urging agency owners to foster enthusiasm for AI among team members, positioning their agencies to thrive amid disruption.