In the arts sector, success often feels fleeting. A record-breaking season or a standout fundraising campaign can feel like a lucky break—a brief high point in an otherwise challenging year or years. But sustainable success isn’t luck – its leadership. It’s the result of disciplined execution and smart leveraging of your organization’s unique assets.
During a recent conversation with Paul Winberg, President and CEO of Grant Park Music Festival (GPMF) and long-time TRG Arts client, he shared insights into how his organization has consistently built on its successes year over year, even in the face of challenges like COVID-19. His reflections offer valuable lessons for arts organizations looking to achieve long-term growth.
One of the key takeaways from Paul’s experience is that success is cumulative. Each year builds on the foundation of the previous one. GPMF entered the pandemic in a strong position, and while 2021 and 2022 were difficult years, the organization continued to build momentum. By 2024, GPMF hit what Paul describes as a “high watermark” year, driven by strategic planning and disciplined execution.
What does this mean for other arts organizations? It’s a reminder that there’s no magic bullet or quick fix. Long-term success requires consistent effort and a commitment to core strategies. Whether you’re focusing on ticket sales, fundraising, or audience engagement, it’s about doing the right things repeatedly and improving incrementally.
Arts organizations often overlook the power of their unique assets—whether it’s their venue, programming, or community connections. GPMF’s outdoor venue allowed them to resume live performances earlier than many other organizations during the pandemic, giving them a head start in audience recovery.
For your organization, leveraging assets could mean capitalizing on a unique programming niche, deepening relationships with local partners, or finding creative ways to engage audiences. The key is to recognize what sets you apart and lean into it.
A common pitfall for arts organizations is chasing the latest trend or innovation without maintaining focus on core business practices. While innovation is essential, it must be balanced with disciplined execution.
Paul emphasized the importance of sticking to proven strategies, even when the temptation to try something new arises. This doesn’t mean avoiding innovation altogether—it means ensuring that new ideas don’t distract from what’s working. Your core audience engagement, ticketing strategies, and donor relationships are the foundation of your success. Strengthening these areas should remain a priority.
Paul also shared how TRG Arts has helped GPMF develop a sophisticated ticketing and membership process, describing it as “a huge lift” for the organization. He emphasized the value of having a strategic partner who not only provides the roadmap to achieve ambitious goals but also teaches internal teams how to implement these strategies effectively.
We’ve captured Paul’s insights in a short video as he reflects with Jill Robinson on disciplined leadership and GPMF’s long-standing relationship with TRG Arts:
Consistency matters. Building momentum is about doing the right things repeatedly. Don’t expect instant results—focus on long-term growth.
Leverage your unique assets. Leverage your unique assets. Identify what makes your organization special and lean into those strengths.
Stay disciplined. Avoid the temptation to chase every new trend. Focus on executing core strategies with excellence.
At TRG Arts, we believe that long-term success in the arts comes from a mix of strategic discipline and innovative thinking. Paul’s reflections from GPMF show how organizations can achieve record-breaking results by sticking to what works, leveraging their unique strengths, and resisting the lure of distractions.
What assets can your organization leverage to build momentum? How can you stay focused on disciplined execution while balancing innovation? These are the questions arts leaders should be asking as they plan for the future.