Our Expert

Walter Cross

Founder of Winchester Community | Architect of Darvis AI Investment System

Walter Cross is a respected practitioner and thought leader in the field of intelligent investing. Combining deep expertise in mathematical modeling with a profound concern for the fate of everyday investors, he is committed to using technology, knowledge, and purpose to illuminate the path for retail investors around the world.

Born into a farming family in Fort Morgan, Colorado, Walter was exposed early to bookkeeping, accounting, and farm operations. In 1983, a devastating flood destroyed their home, yet his father chose to give their last truckload of feed to a neighboring farmer in even greater need. That moment taught him the true meaning of responsibility. A value that became the cornerstone of his life.

Walter graduated from the Massachusetts Institute of Technology (MIT) with dual degrees in Physics and Mathematics. He went on to work at Renaissance Technologies and Goldman Sachs Asset Management, where he played a key role in developing multi-factor strategies. Known for his ability to navigate multiple financial cycles with resilience, he earned the nickname “The Cycle Strategist.”

Despite his success on Wall Street, Walter chose to return to his roots.

In 2021, he founded Winchester Community. A cognitive education and collaborative trading platform designed for the everyday investor. He has always believed that ordinary people deserve the right to understand markets and master strategies.

He established three core principles for the community:

Cognitive Empowerment: Elevating investor awareness to manage emotions and avoid impulsive decisions
Systematic Strategy: Guiding investors away from irrational trades with rigorous, scientific methodologies
Social Impact: Using profits to support public good, promoting a positive cycle of wealth and responsibility

Under his leadership, the community has helped tens of thousands of investors develop independent thinking and risk management capabilities. It also launched the 1% Surplus Public Good Fund, supporting scholarships, financial education, poverty alleviation, and more ensuring that the purpose of investing goes far beyond wealth accumulation.

In 2022, Walter began development of Darvis, an AI-powered investment system that integrates factor analysis, emotion detection, and dynamic risk controls. His vision for the platform is clear:

“AI is not here to replace human judgment, it’s here to help protect our rational core.”

From a farm boy to a Wall Street strategist, and now a champion of cognitive awakening and system design, Walter Cross has lived a life that redefines what wealth truly means:

“It’s not how much you make, it’s how many people you help stand taller.”

Strategy Modeling Expert | Crypto Arbitrage Pioneer | Co-Mentor at Winchester Community

Derek Fuller

Derek Fuller is a strategist who blends technical thinking with emotional insight. Known for his principles of “rational grounding” and “systemic empathy,” he is dedicated to creating trading tools and educational systems that empower everyday people to take control of their financial futures.

Raised in the high-precision, high-expectation environment of an engineer’s household in the San Francisco Bay Area, Derek grew up with a unique dual influence. His father, a NASA communications engineer, instilled in him the importance of process-oriented thinking and error calibration. His mother, a compassionate caregiver, taught him that emotional fluctuations are a natural part of the human experience and should be respected and addressed. This upbringing—one parent loving through code, the other through patience laid the foundation for Derek’s distinctive trading philosophy.

He taught himself to code at age 12 and later studied Finance and Statistics at New York University. At 18, he encountered Bitcoin for the first time and became convinced that “markets can be modeled.”

In 2015, he turned down an offer from Goldman Sachs’ research division and instead joined the crypto derivatives research team at Mercury Lab. Within two years, he developed a proprietary dynamic arbitrage system and on-chain arbitrage strategies that led to a 30-fold increase in his trading account earning him a reputation as one of the most technically sophisticated early arbitrageurs in the crypto space.

In 2022, a rotation strategy system that Derek helped design suffered cascading losses during the LUNA/UST collapse. It was the most profound failure of his career. He disappeared from social media for six months and began a full reconstruction of his trading philosophy.

When he returned, it was with a renewed mission not to promote high-yield models, but to teach risk-first thinking. He launched a course titled “What Is a Risk Budget?”, emphasizing risk control, emotional tolerance, and structures built on goodwill. Among traders, he earned a new reputation as “the only one who tells the truth.” His focus shifted from “promising to double your money” to “helping you avoid going to zero.”

In 2023, he met Walter Cross at a private AI finance summit. Their philosophies proved complementary Walter built cyclical awareness and system discipline; Derek brought detailed execution and real-world strategy. Together, they co-founded Winchester Community, a collaborative education and trading platform for retail investors.

At Winchester, Derek is responsible for:

Designing practical strategy systems (options structures, on-chain arbitrage, automation engines)
Optimizing dynamic risk control mechanisms (emotional tolerance, position sizing)
Enhancing user interfaces and teaching strategy execution

He firmly believes:

“Investing isn’t about doubling your money through luck—it’s about avoiding zero through awareness.”

Today, Derek no longer seeks to be idolized. Instead, he aims to be “someone who speaks honestly, explains risk clearly, and helps people take fewer wrong turns.”

He lives by one guiding principle:

“Technology should serve humanity. Systems must carry warmth.”