Bespoke Bay Blog
A periodic exploration of the philosophy and psychology of modern leadership, anchored in research and translated into action.
Written by: Matthew Kurkjian
Tall Ships = Tall Orders: A Framework For Reflecting After Taking Out The Ship (Or Minivan)
In my free time, I volunteer with Call of the Sea, crewing aboard the brigantine Matthew Turner out of the Bay Area. We take students out sailing to experience the maritime environment, local history, and something increasingly rare in the classroom: learning by doing.
This year, I had the opportunity to blend my passion for sailing-driven education and my Ph.D. dissertation focus.
The Reflective Advantage: A Leadership Tool To Learn More From Experience & Hedge AI
Reflection allows us to get more value out of experiences we’ve already “paid” for and is the key to discovering the foundations of our successes, failures, and ultimately our happiness. Let’s make sure we’re getting the most out of reflection by structuring it differently in 2026.
Character Is the New Competitive Advantage in Hiring.
AI is making intelligence cheap. What now, if we, as a hiring and labor force with a focus on indicators of intelligence in candidates, must continue to make intelligent hires, if intelligence itself is so concretely and fervently being imitated? The currency of intelligence has entered hyperinflation.
When Plans Fall Apart, Growth Begins
Your plans will fail you, but the act of planning will never. The value is the adaptable mind you build while planning. The journey, is in fact, the destination.
The Problems of Incentives
When every action has a price tag, purpose starts to lose its signal. Incentives can move work forward — or drown out what made it meaningful in the first place.
Have We Forgotten Ockham and His Blade?
“I apologize for such a long letter - I didn't have time to write a short one.” - Mark Twain
Clarity is not only found in what we say, but also in what we cut away.
Leadership at Human Speed: The Case for Going Analog
Analog Leadership offers more than another style of leadership: it’s a necessary framework for re-grounding leaders at human speed in an era defined by digital overwhelm.
How Companies (& AI) Get Psychological Safety Wrong
Psychological safety isn’t about the absence of judgment, it’s about developing confidence and trust in other people. AI offers anonymity and the lack of judgment, but that’s not the same thing.
Rethinking Intelligence Before We Fake It
As AI becomes more capable and culturally normed, your greatest competitive advantage may lie in the style of intelligence and uniquely human experiences you choose to develop.