Aadeesh Shastry Plays Chess in the Morning and Philosophy at Night

Data strategy expert Aadeesh Shastry

Aadeesh Shastry begins each day with structure and focus. In his New York apartment, mornings are quiet. He reads a few pages from classic philosophy and works through a chess puzzle on paper. This daily routine helps him build clarity and sharpen his thinking before the demands of the day begin.

Raised in Fremont, California, Aadeesh developed a love for systems and strategy early. He ran hurdles on the track team, played competitive basketball, and spent time studying chess. These activities combined movement, pattern recognition, and focus—skills that continue to guide his work and thinking today.

He earned the rank of Eagle Scout through the Boy Scouts of America, where he gained early experience in leadership, goal-setting, and collaborative problem-solving. He later graduated from the University of Chicago in 2022 and completed his master’s degree at NYU in 2023, concentrating on data analysis and decision frameworks.

Today, Aadeesh applies structured thinking and calm under pressure to both his professional and personal life. He continues to train his mind through chess, basketball, and reflection. He maintains a journaling practice to track lessons from mistakes, challenges, and everyday decisions. His habits are shaped by the belief that strong thinking comes from consistent practice.

Can you tell us a bit about yourself and what you do?

I’m based in New York and work in data strategy and systems thinking. My background is a mix of analytics, philosophy, and competitive environments—track, chess, and basketball. I’m most interested in how people make decisions under pressure and how we can get better at it.

How would you describe your personal or professional vibe in 3 words?

Focused, calm, adaptive.

What’s one fun fact about you most people don’t know?

I still use a physical chess clock when I play with friends. It turns every game into a high-pressure mental workout, even if we’re just hanging out.

What’s your favorite TV show right now?

The Queen’s Gambit. I watched it again recently and still love how it captures both the beauty and intensity of chess. It’s not about being perfect—it’s about how you handle your mind under stress.

What’s your most-used social media app these days?

Twitter (now X). I curate it carefully—mostly tech, philosophy, and niche productivity corners. I like that it forces people to be concise.

What was the first social media app you ever joined?

Facebook. I think I joined just before high school. I didn’t post much, but it was where everyone coordinated everything—from group projects to pickup games.

Are there any influencers or creators you never miss content from?

Ali Abdaal, for his productivity content that doesn’t feel performative. Also, Farnam Street (Shane Parrish) for decision-making insights. And Magnus Carlsen highlights—chess brilliance never gets old.

Are there any must-follow accounts or pages for people in your industry?

Yes—@visualizevalue for systems and clarity, and @chesscom if you're into pattern training. I also follow @naval for thought-provoking frameworks that cut through noise.

Do you listen to any podcasts related to your field or niche?

Yes, The Knowledge Project is a favorite. Also, Hidden Brain for understanding human behavior. Sometimes even Lex Fridman—the episodes can be long, but I always come away thinking differently.

What’s the best advice you’ve heard from a podcast or interview?

From Shane Parrish: “You don’t rise to the level of your goals, you fall to the level of your systems.” That made me rework how I plan my weeks.

If you could collab with any influencer or celeb, who would it be?

Probably Tim Ferriss. Not just because of the productivity stuff—but because he’s curious in so many directions. I think we’d make something weird and useful.

What’s a habit, hack, or tool you swear by for staying informed or inspired?

Journaling after something goes wrong. Not just to vent—but to understand what I assumed, what went off, and what I’d do differently next time.

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