Savouring the Trend — An Evening with Jerry Parker at Raoul’s, New York

New York does not reward hesitation. The city moves with velocity and expectation, compressing ambition, theatre and commerce into a few crowded square miles. Yet amid the noise and movement, the essence of trend following remains remarkably unchanged: patience, discipline, and the willingness to ignore distraction. It was against this backdrop that the Aussie Turtles, Adam Havryliv and Richard Brennan, travelled to Manhattan to dine with Jerry Parker at Raoul’s in SoHo.

Before dinner, we met Jerry at his brownstone in the East Village. The evening began with a short walk downtown through the late-summer energy of Manhattan. Earlier that day, after landing at JFK Terminal 1, we had endured the slow crawl into Midtown as traffic built around the US Open. Mentioning this to Jerry prompted immediate laughter. Asked how his own transfer into the city had been, he casually explained that he had avoided the roads entirely by taking a helicopter from the airport to the Manhattan heliport. Jerry, it seemed, was fully committed to savouring the trend.

Raoul’s suits New York. The restaurant balances old-world confidence with downtown unpredictability. Tables are tightly packed, the room animated but never chaotic, and the atmosphere carries the feeling that almost everyone present has somewhere more important to be later. Securing a table on short notice is no simple task, though Jerry’s long-standing connections in the city appeared to smooth the process effortlessly. Between stories of restaurants, bars and the changing rhythms of Manhattan life, it became clear that New York remains a city he genuinely enjoys.

The meal unfolded in the relaxed style that defines good trading conversations: serious topics explored without ceremony. We began with oysters, crab beignets and a rich lobster bisque shared between the table. Dover sole followed as the main course, accompanied by pommes mousseline, haricots verts and pommes frites to share. Sparkling water carried the evening through, before espresso closed the dinner in appropriately understated fashion.

Upstairs, on the way to the bathroom, another distinctly New York moment emerged. A fortune teller had stationed herself beside the staircase, offering advice to diners while they waited. There was no queue, and we politely declined the opportunity. For a statistically minded trend-following group, predictive mysticism felt unnecessary. Markets already provide enough uncertainty without outsourcing it to clairvoyance.

Conversation throughout the evening moved naturally between markets, structure and philosophy. One particularly animated discussion centred on the use of closed-trade equity for position sizing and its implications for subscriptions and redemptions within managed products. Jerry’s argument was clear, internally consistent, and ultimately persuasive enough to carry the discussion. Like many of the best systematic traders, he approaches disagreement not emotionally, but numerically.

Jerry occupies a unique place within the history of trend following. With a background in accounting, he was comfortable with numbers long before he encountered markets professionally. When he first saw the performance profile of trend following, he immediately recognised its significance and pursued the opportunity to join Richard Dennis’ original Turtle Trading experiment. Decades later, Dennis remains both an influence and close confidant.

That direct lineage matters. Jerry’s experience was forged during the formative years of systematic trading, before the industry became crowded with optimisation, complexity and institutional fashion. The discussion repeatedly returned to his belief that many modern trend portfolios have drifted too far toward volatility smoothing and over-engineering, often at the expense of the pure asymmetry that originally defined the strategy.

Yet despite his attachment to the classical school of trend following, Jerry remains forward-looking. Conversation turned to his latest venture: TFPN, a trend-following ETF that combines global futures exposure with systematic trend following across equities. The result is a remarkably broad and tax-efficient portfolio spanning more than 400 instruments. The concept reflects Jerry’s enduring instinct for practical innovation rather than innovation for its own sake.

There were hints, too, of what may come next. Jerry spoke enthusiastically about new ETFs currently on the drawing board, fresh algorithms under development by Chesapeake’s trading team in Florida, and even the possibility of a future bond-focused product. Nothing was presented theatrically. The ideas emerged in the same calm and measured tone that characterised the rest of the evening.

As the evening wound down and coffees arrived, the conversation drifted from products and portfolios toward longevity itself. Many industries reward novelty. Trend following rarely does. Its edge comes instead from surviving long enough for disciplined process to matter.

New York may celebrate speed, but dinner with Jerry Parker was ultimately a reminder that the most enduring investment philosophies are often the least hurried.

The Ledger

• Moonrise Petite Oysters: USD 30
• Jumbo Lump Crab Beignets: USD 27
• Lobster Bisque (shared): USD 48
• Dover Sole “Grenobloise” (x3): USD 180
• Pommes Mousseline: USD 14
• Haricots Verts: USD 14
• Pommes Frites: USD 14
• Sparkling Water: USD 24
• Espresso: USD 18
• Subtotal: USD 369
• NYC gratuity (~22%): USD 81

Total: USD 450

Using exchange rates from 4 September 2025:

USD 450

~AUD 690
~CHF 395
~EUR 410