The Art of Live Event Marketing: War Stories and Wisdom from the Front Lines

Alana Rauert
Jul 21
5 min read

Updated: Jul 22

Meet Jacqui O'Callaghan, who's been wheeling and dealing in the music industry since 1986 - back when Michael Jackson was still moonwalking and venues actually answered their phones. Here's what nearly four decades in artist management and live event promotion have taught her about making magic happen.

How It All Started: From Record Shop to Rock and Roll

Picture this: 1986, Palings Music Centre, and a young Jacqui discovering that the music industry was her calling. She completed a course in Band Management, which helped her land early wins like radio play and ticketed gigs for emerging acts. "I’ve always admired the courage it takes to get up on stage. As someone who understands the emotional depth of artists, I know how deeply rejection can impact them. My mission has always been to protect, support, and promote artists with care and dedication.”

Fast-forward nearly 40 years, and she’s had the privilege of working alongside and learning from some of the industry’s biggest names — from Michael Jackson and Crowded House to Ian Moss, Troy Cassar-Daley and Mental as Anything. Conversations with Neil Finn, in particular, helped shape her approach to artist management, reinforcing what she’s learned over time: that success in this business is equal parts passion and persistence.

But here's the thing about the live events world - it's not just about booking acts. It's about understanding that every artist who steps on stage is putting their heart on the line, and every venue owner is trusting you to fill their room. Get that balance right, and magic happens. Get it wrong, and, well... let's just say Jacqui has stories about that too.

The Art of Perfect Matchmaking (It's Like Tinder, But for Venues)

When Vodafone Wanted Bodyguards (Yes, Really)

One of Jacqui's favorite booking stories involves a Vodafone Christmas party where the client specifically requested "bodyguard" entertainers. Enter the Hoozat Entertainers - perfectly matched for a corporate crowd wanting something edgy but professional. "One of my key values is ensuring the right act is booked for the right event. I personally consult with every client to understand the atmosphere they wish to create and carefully match entertainment to suit. From wedding bookings to major corporate events."

The secret sauce? Dig deeper: What atmosphere are you trying to create? What do you want people to feel when they walk in?

Cold Calling: The Skill That Pays the Bills

The Peer Tavern Chronicles

Let's talk about cold calling, because despite what LinkedIn influencers tell you, it still works. Jacqui's approach to venues like Peer Tavern in Cairns or The Railway Hotel in Byron Bay wasn't just about making calls - it was about doing homework first. "I'd visit venues, watch their crowds, understand their vibe. Then when I called, I wasn't just selling - I was solving their programming puzzle."

Her cold calling success came from a simple formula:

Research the venue's current programming gaps
Lead with solutions, not sales pitches
Always have backup options ready

The Faulty Towers Empire: How to Launch a Phenomenon

Building Buzz Before There Was Social Media

Before Instagram stories and viral TikToks, there was legwork. When Jacqui helped launch the Faulty Towers Dinner Shows, the strategy was all about creating genuine excitement through traditional media and word-of-mouth.

The Ridge Hotel launch in Spring Hill became the template for success: media launches with radio stations and newspapers, partnerships with social clubs, and here's the kicker - actors performing pro bono at the launch to give everyone a taste of the show.

The three-year run at Ridge Hotel proved the strategy worked, but it also taught valuable lessons about venue partnerships. "When a venue trusts your judgment enough to commit to regular programming, you've moved from supplier to partner."

Network Like Your Career Depends on It (Because It Does)

Brisbane Tourism Expos: Where Dreams Come True

In the 1990s much of that success came from relentless networking through Brisbane Tourism and Wedding Expos. "I'd work those events like my life depended on it," she says. Her expo strategy yielded regular gigs at prestigious venues:

Kookaburra Queens - consistent bookings through relationship building
ABC Radio - ongoing performance opportunities
Brisbane Museum - cultural events requiring sophisticated acts
O'Reilly's Guesthouse - destination venue work that artists loved\

"Expos are for relationship building, not closing deals."

Financial Reality Check: It's Not All Rock and Roll

The Hamilton Island Learning Experience

Managing logistics for acts performing everywhere from Airlie Beach to Hamilton Island taught Jacqui that successful event management means thinking like an accountant and a tour manager simultaneously. "You're coordinating accommodation, hiring sound engineers, managing payments, and handling reconciliations - all while making sure the artist feels supported and the venue gets exactly what they paid for."

One particularly challenging Hamilton Island gig involved last-minute sound equipment issues that nearly derailed the entire event. "I learned to always have backup plans for your backup plans. And to build buffer time and budget into every proposal, because Murphy's Law is particularly active in the live events business."

Supporting Original Music: The Uphill Battle Worth Fighting

When Cold Chisel Was Just Another Brisbane Band

"Every cover song was once an original," Jacqui reminds us, and her commitment to supporting new talent comes from understanding this fundamental truth. "Brisbane in the '90s wasn't exactly a hotbed for original music opportunities," she admits. "But that's exactly why it mattered. Someone has to champion the next Cold Chisel while they're still playing pub gigs."

The strategy involved mixing original sets with crowd-pleasing covers, gradually building audiences who came to trust the artists' judgment. "Once you've got them dancing to the covers, they're more open to hearing something new."

Jacqui's Essential Survival Tips for Live Event Marketing

The Hard-Won Wisdom

After decades in the trenches, here's what Jacqui wishes someone had told her at the start:

Protect your artists' emotional well-being - rejection hurts them more than you think
Visit venues as a customer first - understand their vibe before you pitch
Always have backup plans - Murphy's Law loves live events
Build relationships, not just bookings - your network becomes your net worth
Match energy levels to venues - wrong act + right venue = disaster
Support original music when you can - today's orginals are tomorrow's classics
Price properly from the start - underpricing leads to unsustainable relationships

The Beat Goes On

Looking back at nearly four decades in the music industry, Jacqui's story proves that success in live event marketing comes from genuinely caring about the artistic process while maintaining sharp business instincts. Whether you're launching the next dinner theatre phenomenon or helping a nervous singer-songwriter find their first regular gig, the principles remain the same: respect the courage it takes to perform, understand your market deeply, and never forget that you're in the business of creating special moments.

Ready to Make Some Magic?

If you're a venue owner in Southeast Queensland looking for reliable entertainment that actually fits your crowd, or a performer who's tired of playing to empty rooms and wants someone in your corner who truly gets it - reach out and have a chat with Jacqui.