The Puppies of Pitt Street
Welcome to the dispatch from LaKone DeServis, your undercover guide to Sydney’s pulsing core — where the city’s secrets spill faster than a banker’s happy hour pint.
For the past three months, I’ve been embedded deep within the throbbing heart of Sydney’s financial elite: Ryan’s Bar. Here, amid the concrete jungle of Australia Square, investment bankers gather every Thursday night to perform their weekly ritual — a spectacle equal parts tribal bonding and corporate peacocking. Armed with my undercover notes app, steely resolve, and being a woman, gasp, I’ve braved the 5-foot-9 Pure Blonde-scented air to bring you an unfiltered account of this peculiar culture.Ryan’s Bar is not just a watering hole; it’s a cathedral for the city’s suit-clad faithful. The outdoor beer garden pulses with a sea of navy blazers and TM Lewin booties, all moving in synchronized swagger. The men — tall, pink-faced, and unmistakably Anglican — talk in clipped tones about “multiples,” “synergies,” and “the Shore 2nd XV.” To be fair (a phrase uttered with alarming frequency here), Ryan’s is less a bar and more a live-action LinkedIn feed.The women, equally corporate and strategically beautiful, navigate the crowd with practiced precision. They know their worth in this ecosystem: they are the queens of the chessboard, effortlessly cutting in line at the bar while their male counterparts fumble for drink orders. Tragically — or perhaps inevitably — they always end up with men named Ryan or James, who live in Neutral Bay and golf poorly but enthusiastically.But let us not forget the true stars of this show: the bankers themselves. These are men who can separate emotions from money with surgical precision — a skill that some might call sociopathic but is celebrated here as a badge of honor. Their conversations are peppered with anecdotes about deal closings, bonus pools, and Matthew Grounds’ mythical rainmaking abilities at UBS Australia. They laugh loudly, slap each other on the back, and occasionally glance at their Rolexes to ensure they’re still ticking. The deals don’t make themselves, after all.The drinking rituals are as structured as their PowerPoint slides.
Beer flows like venture capital funding during a bull market — fast and reckless. The $15 happy hour specials fuel their bravado, while wine glasses serve as props for grandiose storytelling about “pivoting to PE” or surviving 100-hour workweeks. For dinner? Liquid carbs reign supreme; food is merely an afterthought unless it’s nachos shared over a discussion about leveraged buyouts.As the night wears on, Ryan’s transforms into a surreal carnival of finance bros letting loose. Cigarette smoke mingles with Top 40 hits blaring from speakers. A DJ — no musical genius but adept at crowd manipulation — coaxes them into impromptu dance floors. Stiletto-clad women join the fray, creating an intoxicating mix of ambition and after-work desperation. It’s less “Wolf of Wall Street” and more “Puppy of Pitt Street,” but the energy is palpable.The Thursday night escapade is just a warm-up for a looming specter: the infamous ‘Casual Friday.’ Corporate Australia gets to hand off their slacks to the local dry cleaners and don their finest polo shirts and chinos — a sartorial rebellion that’s more symbolic than substantial. It’s a day when the line between work and play blurs, and the bankers can pretend to be something other than their ‘grindset mindset’ suiting selves. Yet, even in their casual, there’s an air of competitiveness — a silent competition to see who can pull off the most stylishly rumpled look while still managing to discuss EBITDA margins over a morning coffee and a hangover.By midnight, the crowd begins to thin as tomorrow’s Excel models beckon. The bankers retreat to their apartments in the ‘it’s better than the east’ North Shore, leaving behind empty beer bottles and faint echoes of “to be honest.” Ryan’s Bar stands quiet once more — a battlefield awaiting its next skirmish.And so ends another Thursday night at Ryan’s Bar: where Sydney’s investment bankers come to unwind, network, and remind everyone why they’re simultaneously revered and reviled. For those seeking a glimpse into this world, I recommend bringing your best suit — and perhaps your thickest skin.
Til next time,
LaKone (contact me with your stories at LaKoneDeServis@protonmail.com)
