SXSW Sydney Pulled It Off: Everything We Learned

I am a SXSW veteran. I fly to Austin every year and love it each time, I’ve been going for nearly a decade.

However, like me, most people were very nervous about SXSW Sydney. I was excited at the prospect of the most iconic business conference in our industry coming to Sydney, but praying that we could do it justice.

The stakes were high. If the SXSW Sydney team pulled it off, it would mean an incredible global cultural moment for our region every year; this would be not only a huge financial benefit to almost every Australian art, technology, and media business, but also give Sydney the cultural moment it so deserves. Something real, something iconic, something more than just projected lights on Sydney buildings every winter. 

Like many brands and companies, we were tossing up whether to participate in the first year. It was a big financial and resource investment for us, and it wasn’t clear how many people would attend or what the ROI would be. 

Ultimately, we decided to pull the trigger on two venues: The Courtyard Presented by Rolling Stone and the DEPT x Variety Australia Garden.

Over half a million dollars of investment from our company, The Brag Media, went into SXSW’s debut year, and we had brought sponsors along for the ride who trusted us too. Terrifying, yes, but would it work? 

The lead up was very touch and go. Understandably, it was the SXSW Sydney team’s first year and a lot of things were up in the air right until the last minute. This meant there wasn’t a lot of clarity around things that needed to be clear, and most important decisions and sign offs happened at the very last minute. 

These were all teething issues that were to be expected of a debut event of this magnitude, but as understandable as it was, it only made our nerves more exaggerated. 

During this time of uncertainty, I spoke with many brands and people in the industry and although most were nervous and skeptical, everyone I spoke to had one thing in common: we as an Australian business community wanted SXSW to succeed, and it felt like an aligned mission. 

And the result? Well, the headline gave it away from the jump, because SXSW Sydney was inspiring. 

They created such an incredible atmosphere that had all the magic and inspiration of Austin with a distinct Sydney feel. Everyone I spoke to was getting so much out of it from learnings, experiences, and discovering new artists. 

For me, the Chance the Rapper through line for the week defined what SXSW is about.

The night before Chance’s keynote, he was at Fortress playing games built by Australian game developers; he then got on stage the next day with Rolling Stone AU/NZ Editor-in-Chief Poppy Reid and explained to a packed theatre that SXSW was responsible for kickstarting his career and why he is where he is today. As he spoke those words you could feel the collective butterflies move through the room.

Then, to cap it all off, he finished SXSW by popping into the Gladdy introducing and absolutely vibing to 11-year-old rapper Inkabee. 

If anything defines what SXSW is, this is it. 

Chance The Rapper was VIBING to 11 yr old Indigenous rapper Inkabee. @chancetherapper pic.twitter.com/SsaRZHdwG0

— Ben Martin (@BenMartian) October 21, 2023

Biggest thing to happen at the Gladdy since Dipset won trivia 5 times in row. pic.twitter.com/3oRTcp68em

— Ben Martin (@BenMartian) October 21, 2023

Other highlights of SXSW was 10k people packed for the IEM final, Spotify’s super insightful AI discussion with DJ (“X”) and, quite broadly, the brand activations were awesome. It looked to me that Amazon’s activation had more people through it than any Amazon activation I’ve seen in Austin – stunning. 

So, as we debrief on SXSW 2023, I thought I would share The Brag Media’s learnings as we will soon start planning for 2024.

1. Never take on Mel Hopkins 

This lesson is probably the hardest thing to act on, but knowing who you’re up against when planning your events or activations is key. 

Both our Rolling Stone Courtyard and Variety x DEPT spaces were packed every night except for one window, early Wednesday night when Channel 7 had their upfronts. 

During that time, every media SXSW badge holder needed to get to Mel Hopkins’ impressive Channel 7 activation where she hosted their annual upfront; if you’re wanting to put on shows to attract people at SXSW, putting one on during the Channel 7 upfront is a dumb idea. 

So next year it would be great to get greater visibility over what else is running and when, but this may not always be possible. As I mentioned, our venues were at capacity every night except for this one moment, so ideally we’d avoid that in 2024. Maybe that’s just the reality of SXSW – you can’t win every minute of every day. 

2. Location matters

Both the Rolling Stone Courtyard and DEPT Gardens won on location. DEPT was right next to the ICC and the Rolling Stone Courtyard was next to WPP house, only 700m or so from the ICC. 

You can’t underestimate the power of location.

Both locations were stunning in their own right, too. We loved the Rolling Stone Courtyard because it felt like the most “Austin” venue in Sydney, and anyone who went to the Dept Garden party would tell you it was the most beautiful location at SXSW. 

Both of these factors at each event gave us a competitive advantage and meant every night our venues were full. 

3. Secret headliners > announced headliners

This is something we stole from Rolling Stone in Austin. This year, Macklemore was the secret headliner for Rolling Stone at SXSW in Austin, so we wanted to recreate that with the best Australian talent for SXSW Sydney. 

We were lucky to have four secret headliners across four nights: Jessica Mauboy, Skegss, Teenage Dads, and 360, all performing to a small room of a few hundred people when ordinarily they would perform to thousands. 

We created a money can’t buy experience for music fans, and this is what SXSW is all about. 

4. Games and interactions matter 

Twilio had a cornhole activation at the Rolling Stone Courtyard with a $500 prize, it was incredibly fun. People kept coming back trying to beat their streak throughout the weekend. A very smart and easy way for a brand to interact with badge holders. 

5. Comfort matters 

Old El Paso and Jim Beam did two brilliant things for SXSW badge holders: they had comfortable VIP sitting areas at Rolling Stone Courtyard featuring free food and drinks.

Why is this so great? Simply put, SXSW is long and exhausting, and sometimes you just want somewhere comfortable to sit, relax, and watch some bands. Both Old Ed Paso and Jim Beam provided that all week, hence their VIP areas were always full. 

6. Worlds colliding is a recipe for success 

The only panel we hosted at the Rolling Stone Courtyard was a Twilio panel titled, “What artists can learn from tech, and what tech can learn from artists.”

It was an incredibly compelling talk about the secrets of customer/fan growth from both industries. We will be publishing the full panel on Rolling Stone’s YouTube channel in the coming days. 

• Sydney SXSW was super spread out, so in 2024 it would be great to feel “always in SXSW” when walking from venue to venue. That means more signage and more activations around the city. The latter I’m certain will happen as more brands are likely to flood in for 2024. 
• Allow more detailed filtering on the search in the app. It would be great to filter delegates not only by industry but also job title and company. 
• More headliners like Chance the Rapper. No brainer, I know, but it’s a lot harder for us to bring US headliners to SXSW Sydney than it is for Austin due to how far we are away. Hopefully more people buy badges earlier so SXSW Sydney have a bigger budget and can double down in 2024 as I’m sure they will.  

I chatted to Colin Daniels, the SXSW Sydney CEO, on the last day of the Rolling Stone Courtyard and asked him what he was most proud of. His response summed it up great:

“I walked out during happy hour early in the week and every single brand activation was full of people drinking and connecting and having fun, that was when I knew we did it,” he said.

SXSW Sydney is just the start, and I can’t wait to see what Colin and his team do in 2024.