WHAT ARE WE DRINKING? – WITH JACK TRAYNOR
A conversation about connection, community, career evolution and why showing up genuinely is the most powerful brand strategy of all
There are some guests who walk in and instantly bring warmth into the room – the kind of energy that makes you feel like the conversation is going to go exactly where it needs to go. Jack Traynor has that effect. He’s grounded, open, funny, and refreshingly self-aware, and from the moment he sat down, it was clear this episode would be one of those beautifully unfiltered, community-centred conversations that remind you why this podcast exists in the first place.
THE DRINK THAT GAVE HIM AWAY BEFORE HE EVEN SPOKE
Jack chose a Merlot, and the moment Soli (our resident drink-psychologist-slash-ChatGPT) began his reading, we all knew we were in for a good time. According to Soli, Merlot drinkers tend to be balanced, emotionally intelligent, diplomatic, grounded, steady, and quietly sentimental, the kind of people who value connection, depth, and meaningful conversation.
When we layered that over Jack’s passion for Caffeine Connections, a community networking event literally built around trust, conversation, and no-bullshit connection, the accuracy was almost too perfect. The drink had chosen the man as much as the man chose the drink.
Jack laughed at the breakdown, joking that he was expecting Sully to call him a “posh prick,” but instead he was painted as someone deeply human. Someone steady. Someone who appreciates the finer things without needing to perform for anyone. And that set the tone for the entire chat.
THE CAREER ROOTS THAT SHAPED HIM
Jack’s story is grounded in care real care the kind that comes from years building relationships across aged care, health, and disability services. He spent ten and a half years in aged care, working across multiple agencies in Wollongong, before taking on roles in NSW Health and then transitioning into disability support .
What became clear very quickly was how much identity he has built from being in service to people. He has this blend of experience that gives him both perspective and empathy, qualities that turned out to be the perfect foundation for what came next.
THE HEART OF CAFFEINE CONNECTIONS
But the part of the conversation that carried the most soul was when Jack spoke about Caffeine Connections, the event he created back in 2014 because he couldn’t find a space that felt inclusive, relaxed, and genuinely human. He wanted something that wasn’t corporate, wasn’t cold, wasn’t all scripted elevator pitches and transactional networking, just a Monday morning space where people could show up, breathe, laugh, share, and connect without pressure. A space where the networking didn’t end when the event ended, but also a space built around the idea that connection, when done right, has a long tail.
He admitted, very honestly, that he originally started it to boost his own personal brand, but it quickly grew into something far bigger and more impactful than he ever expected. Today it is a well-loved, community-first gathering point for Wollongong’s business and disability sectors, a place where people feel seen, welcomed, and connected in ways they didn’t realise they needed .
THE JACK WE MET IN THIS EPISODE
What made this episode special was Jack’s presence. He has this ability to mix humour with heart, professionalism with authenticity, and storytelling with purpose. He is someone who honours the communities he serves and someone who genuinely believes in the power of conversation, not the polished version, but the real, messy, human kind.
He represents a generation of sector leaders who don’t need to pretend, posture, or carry ego into a room to create impact. He simply shows up as himself – steady, connected, curious, and kind, and people meet him there.
WATCH THE FULL EPISODE
This episode carries depth, heart, and truth in every direction, and I have no doubt it will resonate with anyone who has ever had to rebuild themselves piece by piece.
