WESTERN SYDNEY ROYALTY, HOSPITALITY QUEEN, AND THE WOMAN BEHIND PENRITH’S MOST ICONIC VENUES
There are guests who walk into a podcast with presence, and then there’s Jessica Jenkins, the woman who somehow embodies Penrith grit, Florence nostalgia, London precision, and enough hospitality magic to build a small empire on High Street.
Jessica’s drink was an Aperol Spritz. It was a drink loaded with memory, personality, and a whole chapter of her life, and when Soli summed it up, that she’s the kind of woman who walks into a room with main-character energy and a mix of fun, sophistication, and “I’ve still got my shit together even when I don’t”, you could feel the whole room nod in unison.
THE BUSINESS SIDE — THE PENRITH TRINITY
Jessica shapes the cultural heartbeat of Penrith. She and her family own three hospitality businesses, all wildly different, all serving their own little pocket of the community.
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Mr. Watkins – the Icon
Eight years on High Street. A café by day. A speakeasy-style bar by night. A fit-out that makes people literally say, “I don’t feel like I’m in Penrith anymore,” and an atmosphere built from warmth, storytelling, and flawless service.
It’s refined but not pretentious. Dark but not moody. Private enough for a business meeting, intimate enough for a date, friendly enough that you end up telling the staff your life story by accident. Jessica describes Watkins as the place where she grew up as an owner, the venue that demanded the grind, the sacrifices, the late nights, and the connection to people that keeps her so deeply in love with hospitality.
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Elton Chong – the Problem Child (That Everyone Loves Anyway)
Born during COVID, designed with chaos, graffiti, colour, and pure rock-and-roll energy, Elton Chong has morphed into Western Sydney’s unexpected home of live music.
It’s loud. It’s rough. It’s welcoming in a way that makes neurodiverse patrons, young creatives, and subcultures feel safe and seen.
It’s also the venue Jessica describes as a “labour of love”, not a profit machine, but a gift to the community. Grants, sound upgrades, a new stage, renovated bathrooms, every step is about giving Penrith a place to watch real bands, real shows, and real culture without having to trek into the city.
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Harry Hotdog Café at High Street Social
The unexpected third child, one they didn’t plan, but ended up loving anyway.
Run by her sister Tara and long-time friend Marie, this venue represents everything hospitality is supposed to be: family, trust, showing up for the people who show up for you. Jess doesn’t need to be on the floor there because the people who run it hold the same values she does: warmth, good food, good coffee, and a workplace built on loyalty.
THE PODCAST CONVERSATION – A MASTERCLASS IN COMMUNITY, CULTURE & COURAGE
The episode went far beyond drinks and business. Jessica spoke about:
- Moving back from London after losing her dad, then navigating her mum’s need for a double lung transplant, all while becoming a new mum herself.
- Working overseas in high-end restaurants, where hospitality was treated as a respected profession, not a stop-gap job.
- Learning every corner of the industry — wine, butchery, service, numbers, covers, systems — all the foundations that eventually allowed her to build her own venues.
- Opening a venue in Kurrajong Heights, where the grind was so intense she barely saw her son from Thursday to Sunday.
- Meeting Rob, now her business partner, and forming the team that ultimately built Mr. Watkins.
- The reality of rising costs — electricity, wages, alcohol taxes, food costs — and the impossible pressure placed on small business owners trying to keep hospitality accessible.
- The genuine fear that the heart of Penrith’s CBD can’t keep up with the growth of the Western Sydney Airport unless councils and governments move faster.
Her insights were raw, real, and fiercely grounded in lived experience.
WHY THIS EPISODE MATTERS
This wasn’t just a conversation about venues.
It was a conversation about community. About how hospitality shapes human connection, and how much is at risk when the cost of living forces people to pull back from the spaces that keep them mentally and socially alive. Jessica is fighting for more than her businesses. She’s fighting for Penrith’s identity.
For a High Street that reflects the quality of the venues on it.
For live music that doesn’t disappear under the weight of rising costs.
For accessible, meaningful, human places where people can feel connected again.
