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

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.

Oli Luke, founder of Orange & Gray, a thriving hearing healthcare marketing agency, shares his journey from traditional agency work to creating a vibrant community during the pandemic. He discusses the power of capping client numbers to foster deeper connections and trust. Oli emphasizes the importance of community over mere client relationships, leveraging AI for enhanced impact, and navigating the challenges of today’s marketing landscape. His insights reveal a blueprint for agency owners focused on quality over quantity.

Imagine building a $100 million agency, only to watch it collapse. The speaker reveals the highs of rapid growth, acquisitions, and big valuations. But lurking beneath were debt and poor decisions that ultimately led to downfall. Discover the hidden truths about agency scaling, the importance of clear vision, and why financial success isn't everything. This candid discussion provides valuable lessons for aspiring agency owners on navigating the treacherous waters of rapid growth.

Joaby Parker, Founder and CEO of Cover 3 Growth Partners, shares his inspiring journey from agency burnout to sustainable growth. He discusses how he learned that scaling isn't about doing more but doing less effectively. Joaby reflects on his initial struggles, including dependency on referrals and feeling overwhelmed. He emphasizes the importance of empowering team members, recognizing client strengths, and adopting flexible tools for efficiency. His insights offer a fresh perspective on balancing agency demands while fostering team success.

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Most agency owners screw up their first sales hire. Why? Because they either hire the wrong person, or refuse to let go of control. Travis Hoechlin used to think building a sales team was a waste of time—until he realized he was the bottleneck. In this episode, you’ll hear how he went from solo closer to leading a performance-driven team that fuels his agency’s growth. Travis Hoechlin is the CEO of Rize Up Media, a marketing company specializing in law firm services. He shares insights into his journey from working at a large agency to starting his own and discusses the challenges of stepping out of a comfortable position and the motivations that ultimately led him and his business partner to take the leap into entrepreneurship. Travis also shared his experience building a top sales team, his logic behind hiring experienced seller instead of going for junior salespeople he could train, and how he keeps his team motivated and competitive. In this episode, we’ll discuss: What most owners get wrong when building sales teams. The hidden cost of overlooking your top performers. How to hire competitive closers who don’t need babysitting. Incentives that actually work (even with a remote team). 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. The True Cost of Overlooking Top Performers Travis began his career working for one of the largest agencies in the industry. Despite previously owning a mortgage company, he and his current business partner found themselves settling into the comfort of corporate life—big paychecks, steady accolades, and a sense of stability. But deep down, Travis always knew he wanted to build something of his own again. It wasn’t until a disagreement with his former boss that he finally made the leap. Looking back, he wishes he’d made the move sooner. Still, the way it unfolded taught him an important lesson. As one of the agency’s top sellers, Travis had earned a spot in their elite President’s Club—or so he thought. When he was unexpectedly passed over, it became clear that his contributions weren’t truly valued. That moment of frustration became the catalyst for change. Sometimes, it takes a setback to shake us out of complacency. Travis’s story is a powerful reminder: comfort can be deceiving, and top performers often leave not because of the work, but because their impact isn’t fully recognized. For agency owners, it’s a call to action—acknowledge your best people, or risk losing them. The Journey from Seller to Sales Leader As one of the top salespeople at his former agency, Travis was a natural fit to lead sales at his own. But like many high-performing sellers, he was hesitant about building a sales team. Great salespeople don’t always make great managers—and Travis wasn’t sure he could find others who would match the drive and success he brought to the table. His competitive nature added another layer of resistance. The idea of hiring someone who might rival his performance didn’t sit well with him at first. But over time, realized that no matter how strong he was on his own, two or three skilled salespeople giving their all would far outperform his solo efforts. That mindset shift changed everything. Once he found the right people—sales pros who believed in the agency’s mission—Travis stepped back. He moved out of the day-to-day sales role, choosing instead to support the team and help them succeed. After all, they had taken a chance on a growing agency, and he felt a responsibility to help them thrive. Many agency owners struggle with this transition. It’s hard to let go of what you’re great at. But as Travis discovered, tying your value to a single role—especially one you refuse to let go—can turn you into your agency’s biggest bottleneck. Growth requires trust, delegation, and a willingness to lead from the side, not just the front. Strategy for Building a Premium Agency Sales Force Once Travis fully committed to building a sales team, he hit the ground running—bringing on two salespeople to start, then two more just a few months later. Since then, he’s made it a habit to hire two to three new sales reps each year, fueling the agency’s continued growth. While many agencies try to save money by hiring junior reps, Travis believes that route often costs more in the long run. He only recruits experienced, high-performing sales talent since inexperienced hires need extensive training, close management, and time to ramp up—resources many growing agencies simply can’t afford to spare. Instead, Travis looks for people who are naturally competitive, hungry to earn, and confident in their ability to close. In his view, a good salesperson can sell anything. If a new hire hasn’t sold agency services before, he keeps their focus simple for the first 30 days: just book him meetings. From there, he leads the calls while they shadow, learn, and build the confidence to eventually run the sales process on their own. Additionally, rather than hiring one rep at a time, he prefers onboarding two or three at once. Sure, not all of them will work out—but with multiple hires, at least one or two typically stick, and you’re not back at square one. Plus, the healthy competition that comes from a group ramping together drives performance. When top salespeople are surrounded by peers who are also gunning for results, it pushes everyone to level up. For Travis, building a sales team isn’t just about offloading calls—it’s about creating a high-performance culture that multiplies results and drives the agency forward. Incentives That Actually Build Culture—Even Remotely Travis understands that great salespeople are driven by more than just commission—they thrive on competition, recognition, and rewards. In corporate environments, these high performers are often motivated by bonuses, contests, and incentive trips—and Travis knew his agency needed to offer the same kind of energy to attract and retain top talent. Having been the top seller at his previous job, he experienced firsthand how powerful the right incentives can be. So, he implemented a clear and compelling incentive structure for his team: hit an annual sales target of $850,000, and you qualify for an all-expenses-paid trip to a luxury destination, such as their recent five-day retreat at the Four Seasons in Costa Rica. But it's more than just a reward—it’s a shared goal that unites the team. With about a third of his salesforce working remotely from across the globe, these trips serve as a rallying point, fostering camaraderie, motivation, and culture. This blend of healthy competition and team connection is critical in sales. By setting ambitious but achievable goals—and celebrating those who reach them—Travis has built a culture where individuals are motivated to win, and the entire team moves forward together. 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.