The Journey So Far
The Checkmate project took shape back in 2021. Being two brothers who were already investing together, asking what it would look like to stop making investment decisions based solely on instinct and build a system that ran the same logic processes every time.
The first version of Checkmate launched in November 2022.It had the right thinking behind it but not yet the right architecture. Way more data than direction, more inputs than actual process. We learned from it and rebuilt. Version 2.0 launched in May 2024 with a more disciplined scoring structure and the beginnings of what would become our Structured Macro Intelligence layer. Version 3.0 launched in February 2026 adding the War Gaming engine and AI Event Data Indexing. We continually work on this project to this day and plan to start sharing our ETF trading signals with the public as we further refine our systems and model.
Meet The Founders
Connor Flanigan
Connor studied Finance at the Haskayne School of Business, University of Calgary, graduating in 2026 and winning the university's consulting competition in his junior year. As a high performing athlete and now coach, Connor has always set the highest standards for building winning strategies.
Nick Flanigan
Nick studied at SAIT in Canada, Business Academy Aarhus in Denmark, and the University of Gothenburg in Sweden. He holds the Canadian Securities Course certificate (CSC) and has spent over a decade in financial industry across advisory, analytics, and investor education.