Local Entrepreneur Superstar: Gary Berg

Article by Becky Fillinger, photo provided

Did you know we have a local booking agency that brings in over $10 million in annual sales? G.L. Berg Entertainment is celebrating 35 years of success this year - their services include representation of artists of all types for all sorts of events, from local to national! We talked to Gary about why he got involved in this business, the early years, memorable moments and the company’s ironclad and transparent recipe for success. 

Gary BergQ:  What inspired you to start your booking agency, and how has it evolved over time?   

A:  Throughout my life, I’ve had a deep passion for sports and entertainment, both as a participant and an observer. After earning my Master’s Degree in Higher Education, I spent nine years as a college administrator. While I enjoyed that work, I couldn’t shake the desire to create positive, memorable experiences for people through live events. I wanted to help communities and companies connect through high-quality entertainment.

That dream became a reality on July 1, 1989, when I founded G.L. Berg Entertainment from scratch. My mission was clear: to provide professional, non-offensive, high-quality, and affordable entertainment options for companies, fairs, festivals, theaters, schools, and other special events.

Back then, it was just me and a big vision, with gross sales of $30,000 in our first year. Today, I’m proud to say that G.L. Berg Entertainment has grown into a thriving agency with over $10 million in annual sales. Our team includes nine full-time staff members, one part-time employee, and two specialized sub-contractors. We represent more than 300 professional performers who bring joy to audiences across cruise ships, performing arts venues, fairs and festivals, corporate events, schools, and fundraisers.

It’s been an incredible journey, and I’m grateful for the opportunity to do what I love while making a positive impact on so many people.

Q:  What have been the biggest challenges in scaling from local to national operations?

A:  One of the biggest challenges we’ve faced over the years is that every type of event comes with its own unique set of considerations - venues, budgets, dates, locations, and more. On top of that, each market approaches buying entertainment differently, which requires tailored strategies and expertise.

As we’ve grown, we’ve learned that specialization is key. In 2022, we reached a pivotal point where we could establish several distinct divisions, each led by an expert in their respective markets. This structure allows us to better meet the specific needs of our clients and performers while streamlining operations.

Today, G.L. Berg Entertainment is proud to offer specialized divisions for:

• Corporate and Private Events
• Cruise Ship Performers
• Performing Arts Centers (PACs) and Theaters
• Fairs and Festivals
• Speakers (via our Elan Speaker Division)
• K-12 Schools, Colleges, and Universities

This shift has been transformative for our agency, enabling us to provide customized, high-quality service on both local and national levels while continuing to grow and innovate.

Q:  How do you market your business to attract new clients?

A:  Like many successful and growing businesses, we use a multifaceted approach to attract new clients. Our main marketing and sales strategies include:

• Dynamic Web Presence: We maintain a general website along with several market-specific sites to cater to the unique needs of our diverse clientele.
• Industry Engagement: We are active members of industry-specific organizations, which often involves attending tradeshows, networking events, and fostering relationships within those communities.   
• Targeted Campaigns: We employ highly targeted email and direct mail campaigns, ensuring our outreach resonates with the right audience.
• Client Outreach: Regular communication with current and past clients via phone and email helps us maintain strong relationships and uncover new opportunities.   
• Showcase Opportunities: Every time one of our acts performs, they effectively serve as a live showcase of their talent. These performances often generate leads and referrals from captivated audiences.
• Word-of-Mouth Recommendations: Satisfied clients become our greatest advocates, spreading the word and bringing in new business through their enthusiasm.
• Social Media Connections: Platforms like Facebook, Instagram, and LinkedIn allow us to connect directly with clients and share our success stories, upcoming events, and featured performers.
• Proactive Outreach: Sometimes, it’s as simple as picking up the phone and reaching out to potential clients we know would benefit from our services.

This combination of modern marketing strategies and traditional relationship-building has been instrumental in driving our growth and connecting us with new clients.                    

Q:  Please share some memorable moments in your business - I'm sure there are so many!

A: It’s incredibly tough to narrow it down because there have been countless positive and memorable moments over the past 35+ years. A few that stand out include:

• In year three I hired my first employee and moved to a bigger office and things were starting to take off.
• Created the acapella group Tonic Sol-fa while they were finishing up college and over the next 15 years got shows for them all over the United States, brokered a large sponsorship deal with Herbergers, brokered a deal to get their CD’s attached to hundreds of thousands of General Mills cereal boxes, and built them into a very successful and popular national group.
• Going to Nashville on several occasions as our exclusive acts (comic magician Tim Gabrielson and comic ventriloquist James Wedgwood) performed on variety shows on the Country Music Television network.
• Our acts have also had featured guest spots on The Tonight Show, David Letterman Show, The Today Show, Comedy Central, Last Comic Standing on NBC, America’s Got Talent, The Conan O’Brien Show, Live with Regis and Kelly, The Late Show with Steven Colbert, The Sing Off (where our exclusively represented group Home Free won the fourth season).
• Booking Keith Urban for a Minnesota fair early in his career for $7,500 and bringing him to the state for the first time. Similarly, we booked comedian Frank Caliendo for a company holiday party in St. Cloud for $1,000, and just a few years later, he performed for another client at $50,000 as his career skyrocketed.
• When you go from Zero to almost $100 million in sales over 35 years there are wonderful moments all along the way.  Each year we had a record sales year was/is celebrated in a big way.

Q:  What role does company culture play in G. L. Berg Entertainment's success? 

A:  Company culture is absolutely central to our success and has been a guiding principle since day one. Our mission has always been to only provide entertainment that works. This means every event must work for the client, the performer, and our company. Transparency is the cornerstone of our culture, which sets us apart in an industry where this isn’t always the norm. All contracts are signed by both the client and the performer or speaker, ensuring everyone is fully aware of terms, payments, and expectations. This level of openness fosters trust and eliminates misunderstandings, creating a win-win for everyone involved. If it doesn’t - for reasons like budget, audience composition, or logistical challenges - we don’t move forward with the booking. By prioritizing integrity and alignment with our mission, we’ve built an environment where clients, performers, and staff alike feel respected, valued, and confident in the work we do.

Q:  If you could go back and change one thing about your entrepreneurial journey, what would it be?

A:  Honestly, I have no regrets. Every experience, whether positive or challenging, has been an opportunity to learn and grow, ultimately shaping the success of our company today. That said, if I had to choose one thing, I’d say I might have explored securing capital earlier to accelerate our growth. Our company has always operated without loans or debt, which is a position I’m proud of—it has provided us with financial stability and peace of mind. However, this approach sometimes meant missing opportunities, like hiring additional staff or investing in marketing strategies, simply because the cash flow wasn’t available. While it delayed certain milestones, it also reinforced our resourcefulness and commitment to building a sustainable business. Looking back, the lessons learned from growing at our own pace have been invaluable, and I wouldn’t trade them for anything.

Q:  How may we follow your amazing story?  

A:  Our website (https://www.glberg.com/) is regularly updated with the latest news, and we’re active in the community, which means we occasionally appear in the media. However, our story is always evolving and somewhat behind the scenes. People tend to follow the careers and activities of the incredible performers we represent rather than us as a company - and we wouldn’t have it any other way! Watching their success is the ultimate testament to our work.