Smart Agency Masterclass With Jason Swenk: Podcast For Digital Marketing Agencies

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What do you do when a business partnership fails? Do you try to engineer the perfect agreement so the exit is clean, or focus on alignment long before anyone signs anything? The truth is, most agency partnerships fail because owners rush into them without slowing down to see the cracks. Preparing for the worst is not pessimistic. It is how you protect the business you are trying to build. Today's featured guest has gone through failed starts, broken agency partnerships, and overcommitting his time as the owner for fear of losing opportunities. He'll unpack 25 years of wins, mistakes, and hard earned clarity, from building his agency and how the biggest breakthroughs came from leadership shifts rather than marketing tactics. Andy Crestodina is the co founder of Orbit Media, a Chicago based web development and optimization agency approaching its 25th year in business. Orbit has grown to a team of fifty f

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What would you do if the merger you believed would change everything suddenly collapsed? Agency owners often dream of the big exit: the acquisition, the payday, the validation. But if you've been in this industry long enough, you know the story rarely goes as planned. Today's guest lived through the dot-com boom, a merger gone sideways, a rare "un-merger," and multiple reinventions across three decades. Today's featured guest is an agency owner who lived through the dot com boom, a merger gone sideways, an unmerger (a rare event), and multiple reinventions over three decades. He'll talk about his journey and the lessons he's gained in resilience, clarity, and what it means to build a business that lasts. Tom Snyder is the founder and CEO of Trivera, a Milwaukee-based agency that originally launched in 1996 under the name Website Solutions. He got his start back when tables ruled the web, Netscape Navig

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training As a user, do you still use search engines or have completely defaulted to AI? How will this shift reshape the agency world? How will ads work when people are only getting the one answer they need? Most agency owners are still treating SEO like it's 2012 — optimizing keywords, buying backlinks, and praying to the Google gods. But search has already changed. People are asking AI for answers, not Googling for links. And if you want your agency or your personal brand to stay visible in this new era, the rules are completely different. Today's featured guest will unpack the shift from SEO to AEO and why most businesses are invisible to AI without even realizing it. Kasim Aslam is one of the world's leading voices on Answer Engine Optimization. He runs one of the largest AEO communities and leads a six person research team that has analyzed millions of AI citations to understand how large language models ch

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training 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. He'll share what he learned about sustainable growth, including why productizing your services sounds great in theory but can actually become counterproductive when it only happens externally. He'll also explain the sales shift that changed everything: offering a low-risk, "foot-in-the-door" engagement that qualifies prospects, builds trust, and creates

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Why do clients keep asking for deliverables they don't actually need? How to get them to focus on the outcome instead of the task list? Every agency owner has had clients show up asking for a website, SEO, or a million social posts, when what they actually need is something much deeper: more leads, more profit, more time back, and a business they're proud of again. Today's featured guest broke down how he built an 11-year-old shop that delivers exactly that. We dig into why small businesses really hire agencies, why "selling SEO" is a trap, and how simplifying complex work can make your agency more profitable, more trusted, and a hell of a lot easier to run. Nico Biggi, Founder of The Gorilla Agency a full-service Oregon digital agency that helps small businesses achieve their marketing goals. After applying to 31 agencies and hearing absolutely nothing back, he decided if no one would hire him, he'd s

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training 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 Univer

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What if growth doesn't make things easier but actually just raises the stakes? Agency life looks glamorous from the outside, but the real growth usually starts in the messy middle. Today's featured guest just wanted to build something of her own, but quickly learned that growth means the challenges get harder, instead of easier, and that your client and team retention will always be the best measures of success, since it means you've managed to build a business that has a real impact on clients and a culture people never want to leave. She'll share the pressure she felt as the agency got bigger, how she learned to celebrate the little wins, and how she built a culture that has truly worked as a strategic advantage. Elyse Lupin is the president and founder of Elysium Marketing Group, a full-service agency specializing in food and franchise marketing. With more than a decade of running the business, she

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training AI is changing the agency landscape faster than most owners can keep up with. Tools are popping up daily, clients are asking if rates should drop, and your team is either fired up or freaked out. Today's featured guest talks about what it takes to build an agency that thrives in a world obsessed with shiny new tech, where the edge is not more tools. It is better leadership, human connection, and an incubator mindset that keeps them ahead without drowning in the noise. Michael Davern is the CEO of Incept, an AI-enhanced, digital-first agency that has been around for a decade. Today, his agency blends automation, machine learning, and human-centered strategy to help enterprise clients grow with clarity and smart execution. He is an early adopter who still believes the real edge is human connection and wants to encourage agency owners to really think about who should lead. In this episode, we'll discuss:

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training If your inbound pipeline dries up tomorrow, do you have a channel that can refill it on demand? Every agency owner needs at least one reliable way to attract new leads when things slow down. Today's guest doubled down on a podcast as his inbound engine, and it paid off big. But launching your first episode is just the beginning. The real growth comes from getting your ideal clients as guests, creating a conversation that builds connection (not just content), and staying consistent long enough to earn momentum. He'll break down how to find the right niche, build authority through partnerships, and turn podcasting into a powerful inbound system that keeps quality leads coming in on autopilot. Chase Clymer is the co-founder of Electric Eye, a Shopify Plus partner agency specializing in conversion rate optimization (CRO) and e-commerce growth strategy. Since 2016, he and his team have been helping direct-t

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training If you're one of the many owners concerned that AI will end the agency model, what are you doing to stay relevant? How are you building lasting relationships that help clients see your value beyond executing tasks? Artificial intelligence, automation, and enterprise-level change have everyone in the agency world wondering what's next. However, agencies have managed to stay relevant with past technological disruptions and the answer has always been: you need to adapt. Today's featured guest has scaled his business through seven iterations for over fourteen years by being willing to adapt to change, and the AI era is no exception. He'll unpack how agencies can stay relevant when technology, data, and client expectations are evolving faster than ever. He also talks about the importance of partnership-based client relationships and why soft skills (not just smart systems) are the real differentiator in the

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Is your agency growing fast but still running without the right structure or leadership team to sustain that growth? If too many people are reporting directly to you, it's a clear sign you've outgrown your current setup. But building that next layer of leadership isn't as simple as promoting your top performers. Without a clear strategy, those well-intentioned promotions can backfire, causing confusion, turnover, and setbacks that stall your agency's momentum. Today's featured guest learned that lesson firsthand. After experiencing a year of costly turnover caused by the wrong management moves, he came away with a better understanding of what real leadership development looks like. In this episode, he'll share what it takes to scale beyond seven figures, the mistakes that nearly derailed his agency's growth, and the key shifts that helped him build a stronger, more sustainable business. Brandon Rost is

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training How do you ensure the highest possible retention levels at your agency? What reasons do you give employees to stay and develop their careers at your agency? Today's featured guest hires fresh talent right out of college. People his team can train into the sort of workers who grow with the agency. However, young talent tends to be ambitious and likely to move on quickly to the next opportunity. To boost retention, he has created a growth path for employees that are a right fit with the agency. He'll break down how he's learned to hire intentionally and build a culture that grows people as fast as profits. McKay Salisbury is the founder and CEO of FiveStar Commerce, an eCommerce agency based in Orem, Utah. His team manages Amazon, Walmart, and Target Plus accounts for over 450 brands annually. What started as a freelancing side hustle on Upwork has grown into a full-service agency focused on team develop

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training How are you preparing your clients to start thinking about AI as part of their SEO strategy? Are you educating them on what they can expect now that the landscape is changing with AI optimization? As an agency, you should be starting these conversations because you can be sure your clients are already thinking about AI, even if they still don't understand its applications for how clients will get to their content. Artificial intelligence isn't just changing how people find information, it's rewriting the rules of search altogether. Today's featured guest is already running AI audits for his clients; he thinks all agency owners should be doing this. He'll unpack what AI optimization really means for agencies, marketers, and business owners who've lived and breathed SEO for decades. Vishal Mahida is the Director of Digital Marketing at E2M Solutions, where he helps over 100 agencies scale their SEO and d

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Is innovation truly at the center of your agency operations? Not just what you offer clients, but in how you operate? With AI raising expectations faster than most agencies can adapt, investing in innovation isn't optional anymore. It's how you build client trust, stay ahead of disruption, and keep your edge. Today's featured guest unpacks his journey from leading the award-winning agency T3 to launching Superstep Capital, a private equity firm investing exclusively in agency and technology-service businesses. His insights cut through the noise on innovation, leadership, and how to stay ahead of the next big shift. Ben Gaddis still calls himself agency guy. After more than a decade building T3 into one of the nation's leading digital agencies, serving clients like UPS, 7-Eleven, and JP Morgan Chase he sold the company and launched Superstep Central, a private equity firm investing in agencies and tech

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Would you say your agency is truly profitable? Take a closer look and assess its structure, systems, and tools through the lens of business maturity. You may find you're still in the chaos stage, in need of structure and vision. Running an agency often starts with passion and talent, but keeping it running smoothly takes systems, leadership, and a strong operational backbone. This operational maturity doesn't happen overnight. As today's featured guest knows well, it's a process of reflection, restructuring, and relentless improvement. Harv Nagra is the Head of Brand Communications at Scoro and host of The Handbook: The Operations Podcast, where he explores how agencies and consultancies build scalable, profitable operations. As someone who has spent his career at the intersection of creativity, consultancy, and operations, he'll discuss the key stages of agency growth, the pitfalls of immature operati

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training How would you go about making acquisitions to accelerate your growth? Would you buy for revenue, culture fit, or client roster? Would you be willing to fire big clients that are holding your agency back? Most agency owners chase growth by saying "yes" to everything, from new services, new clients, and every new opportunity. Today's featured guest built one of the fastest-growing mobile and digital agencies in the world by narrow focusing, firing bad-fit clients, and mastering the art of strategic acquisitions. Today he'll unpack how his agency evolved from a small mobile startup in Tel Aviv to a global digital powerhouse working with brands like Google, Uber, Samsung, and Microsoft. Gilad Bechar is the CEO and founder of Moburst, a mobile-first marketing and digital transformation agency with offices in Tel Aviv, New York, and San Francisco. Since 2013, Moburst has helped startups and Fortune 500s alik

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training How are the new technologies and tools shaping the future of agencies? How can you create an agency that outlasts trends? When you've been around for 75 years in the ad world, you've seen it all, from Mad Men, media buying by fax, the rise of the internet, and now, AI. Today's featured guest runs an agency that has been doing full-service marketing since 1950. What's impressive isn't just their longevity but also how they've stayed relevant and human in a business that changes faster than a TikTok trend. Jennifer Spire is the CEO of Preston Spire, an independent Minneapolis-based creative agency that's been helping brands grow with full-service marketing since 1950. She's the agency's fourth CEO, starting in small independent agencies, rising through global holding companies, and bringing both worlds' lessons to how she leads today. That mix of experiences shaped her leadership style grounded in indepe

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Ever wonder how much your agency's growth is limited by staying too broad? Or what could happen if you picked one niche and went all in? Today's featured guest didn't set out to run a food service marketing agency; He followed the opportunities, learned from a few hard lessons selling door-to-door, and eventually discoverd the power of focus. He'll share how niching down, rebranding, and embracing flexibility helped him grow his agency into a specialized agency serving some of the biggest names in food service and the ways in which he and his team refined the agency's positioning. Tyler Smith is the president and owner of Matato, a brand strategy and creative marketing agency focused on food and beverage brands in the food service and "away from home" space. His agency helps those brands reach restaurant operators, chefs, and food service directors with smarter, more intentional marketing. In this episode

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training Ever looked at your agency's bank account and thought, "We're crushing it!" only to realize two months later that half that cash wasn't really yours yet? Or maybe you've hit that milestone where you start wondering what your agency might be worth if you sold it tomorrow… but your books are a confusing mix of guesswork and gut feelings. Today's featured guest was a finance expert before falling in love with the agency world and has the experience to show how smart financial planning (not just getting more clients) can completely reshape your agency's future. From forecasting and cash flow to the hard truths about selling, this conversation is packed with real-world lessons every agency owner needs to hear. Lacie Edgeman is the partner and co-owner of PrograMetrix, a digital paid media agency that focuses exclusively on programmatic advertising. With a background in finance, she oversees operations and f

Would you like access to our advanced agency training for FREE? https://www.agencymastery360.com/training What would happen if one client lawsuit, one hacked account, or one missed renewal completely wiped out your agency? Have you ever stopped to think about how exposed your business really is even if you’re “doing everything right”? Today's featured guest started his career working in the insurance industry and eventually found a love for marketing. He talks about the side of agency life most people ignore: protecting what you’ve built, and breaks down how to safeguard your business with the right insurance, why every agency should have cyber liability coverage, and how a “give first” mindset has helped him land major clients like Daymond John, Chris Voss, and Dr. Benjamin Hardy. Draye Redfern is a serial entrepreneur and the founder of Redfern Media and FractionalCMO. Over the past decade, he’s built and sold multiple companies, including a $40M insurance agency acquired by one of Warren Buffett’s Berks