The Secret to Longevity: Building Trust and Overcoming Skepticism with James Loomstein | Ep #758

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Do you face a lot of skepticism from clients who have been disappointed by agencies before? How do you go about gaining their trust? After seven years running his agency, today’s featured guest still lists that mistrust as one of his primary challenges and talks about his strategic approach to overcoming this hurdle: combining client education with precise problem identification to deliver time-saving solutions that truly impact their businesses. This approach not only helps rebuild trust damaged by previous agency experiences but also positions marketing as a genuine catalyst for business growth.

Join us as we explore how agencies can move beyond surface-level marketing solutions to become trusted partners in their clients' success stories.

James Loomstein is the managing partner of Rogue Marketing, a digital agency based in Dallas that serves mostly mid-market B2B companies across various sectors. They are business builders committed to solving client problems, whether it's entering a new market, seeking acquisition, or launching new products. James reflects on his journey into the marketing world and the biggest challenges he faced while building his agency.

In this episode, we’ll discuss:

• Rebuilding trust and overcoming skepticism.

• The secret to agency longevity.

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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.

A Winding Path into the Digital Agency Industry

James began his career journey in the early 2000s with a clear goal: to work in marketing. Initially starting in consulting, he found the path to marketing restricted, with an MBA in marketing and strategy as one of the few avenues available. During his studies, he noticed his classmates worked at companies like Kimberly Clarke and American Airlines, which have them a significant advantage and positioned them for immediate brand management roles upon graduation.

James realized early on that the way into the agency world was to start his own agency. However, he still needed the experience so he interned at a big company and after graduation he started to work at Omnicom as a business analyst. Over the years, he worked at different companies and startups.

During the economic downturn of 2008, frustrated with job instability and slow career advancement, James established Digital Space. Over the next four years, he refined his business model, carefully selecting clients and defining his service scope. Eventually, he ended up working for the company where he met his future partner Chip.

Once both he and Chip resigned two years later, their collaboration seemed natural. Chip's agency, Rogue, and James's Digital Space frequently worked together, leading to their official merger in 2016. This partnership marked the beginning of a successful joint venture that continues to thrive.

Rebuilding Client Trust and Overcoming Skepticism

Seven years post-merger, James identifies two major challenges they’ve faced in their growth journey. First, he's learned that accepting unsuitable projects benefits only the client or hired freelancer, never the agency. While difficult to implement, this selective approach has become crucial to maintaining the agency's integrity and fostering meaningful client relationships.

Second, he’s had to face the challenge of the damaged reputation agencies sometimes have among mid-market companies. Having been disappointed by previous agency experiences, these clients often approach marketing services with skepticism. James frequently finds himself rehabilitating the industry's image while diving deeper to uncover the true nature of clients' challenges. Often, what is labeled as a "marketing problem" may actually stem from underlying issues within a company's operational framework. Agencies must strive to understand the specific challenges their clients face and tailor their strategies accordingly. It is the way to create tangible value and measurable results for their clients.

James attributes these agency failures to the low barriers to entry the marketing industry where anyone can claim expertise in marketing with minimal experience. He strongly advocates for aspiring agency owners to gain corporate or agency experience before launching their ventures, arguing that understanding business fundamentals is crucial for success with mid-market clients. Without this foundation, agencies risk failing both themselves and their clients.

The Secret to Agency Longevity

For James, new agencies should start by mastering a specific, well-defined service that delivers clear value to clients. What is something you can take off their plate? What is an area with a specific outcome to achieve? It might start with something very small but if you do it well you’ll not only solve a problem, you’ll also build trust, have a story to tell, and find a way to move forward.

Additionally, don’t just look to solve the client’s problem. Ask yourself whether or not you’re saving them time. If you’re solving problems but clients are constantly telling you what to do, then you’re replaceable. People will always trade time for convenience so it’s to your advantage to do what you can to take the pressure off the client.

For emerging agency owners, James outlines three essential steps:

1. define your target audience

2. identify their core problem

3. establish clear performance metrics.

If potential clients can't articulate their success metrics, they're likely not an ideal fit. Clear expectations and accountability from the start build the foundation for lasting partnerships. This focus on measurable results has led James' agency to move away from traditional retainer models, which often lead to diminishing client satisfaction over time. Instead, his agency has adopted a performance-based approach that emphasizes consistent value delivery throughout the relationship. This results-oriented strategy helps prevent client churn by maintaining clear accountability and demonstrating ongoing value.

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