From Military to Million Dollar Events with Andrew Roby

May 6

Why firing the wrong clients helped this event CEO hit his highest revenue year.

In this episode, we unpack what happens when you set real boundaries, fire misaligned clients, and fully step into your value as a creative entrepreneur.

Andrew Roby, an Army veteran turned renowned event planner, speaker, and coach based in Washington, DC. shares his journey from military service to building a premier event planning business. He opens up about the early struggles with cash flow, how he learned to redefine his ideal client, and why storytelling is the heart of every unforgettable event.

Whether you're an aspiring event planner, entrepreneur, or creative professional, this episode is packed with powerful lessons on pricing your services, attracting the right clients, and building a sustainable business rooted in purpose and authenticity.

What you’ll take away:

Red flags that mean it’s time to fire a client
How to protect your energy and enforce boundaries
Why Andrew changed his entire client base (and what it did for his income)
The mindset shift from freelance to CEO

Connect with Andrew:

Learn more about Andrew Roby Events andrewrobyevents.com
Follow on IG @andrewrobyevents, FB @AndrewRobyEvents and TikTok @andrewrobyevents

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A Remarkable Career Transition

Andrew's path to becoming an elite event planner began in an unexpected place: the United States Army. His military experience provided invaluable lessons in leadership, people management, and operating under pressure. However, the transition from military service to civilian life came with significant challenges.

Building a Purpose-Driven Business

One of the most compelling segments of the conversation centered on Andrew's decision to transform his client roster. Rather than working with any client who could pay, he made the strategic choice to focus exclusively on organizations making positive community impacts.

Lessons in Business

The conversation revealed that Andrew's success stems from mastering business fundamentals that many creative entrepreneurs overlook. Cash flow management, proper pricing strategies, and clear contractual boundaries have been crucial to his company's sustainability. Based on what he’s learned, he now coaches other event planners to help them avoid the pitfalls so many experience.

The Art of Storytelling Through Events

Beyond the business mechanics, Andrew's approach to event planning is fundamentally creative. He describes himself not just as a planner but as a storyteller who crafts meaningful experiences.

Andrew emphasized that this narrative-driven methodology is especially crucial for corporate events, where many planners focus solely on logistics rather than the attendee experience. By centering the human element and designing events that solve real problems for attendees, his company delivers experiences that resonate on a deeper level.

Building a Dream Team

Even the most talented entrepreneur needs a reliable team to truly scale. Andrew shared insights into how he's built his core team. His approach to talent acquisition has been organic and intuitive—identifying people who show exceptional capability during projects and bringing them on permanently. This careful, quality-over-quantity approach to team building has enabled his company to maintain its premium reputation while growing sustainably.

Personal Revelations

Some of the most engaging moments in the conversation came when Andrew shared personal insights. When asked about his definition of success, his answer reflected his generous spirit: success means helping others succeed and watching them grow their businesses.

Final Thoughts

Andrew Roby's journey from military service to elite event planning offers valuable lessons for entrepreneurs in any field. His story demonstrates how aligning your business with your values, mastering financial fundamentals, setting clear boundaries, and focusing on storytelling can create both meaning and profitability.