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Taking a Calculated Chance on Chess8 min read

By Adam Trodd

When I was 5 years old, my blonde bowl-cut and I stood fascinated as an older student from my school battled and enthusiastically checkmated one of his classmates. Instantly hooked. Cue a fateful domino effect in which the game of chess (life-to-date) would serve as an ever-present character in my life ‘s story.  Forrest Gump once said, “You can tell a lot about a person by their shoes…I’ve had lots of shoes.” Well, in when it comes to the case of yours truly – I’ve played lots of chess.

Today, I work for an organization called Thinking Cup Learning. We operate several educational companies. We offer a variety of academic subjects in addition to our chess and related-game services. Our in-person chess tutoring business, Chess at Three, enables students aged 3 and up to learn, play and love chess. Chess at Three operates in New York City/The Hamptons, Chicago, Los Angeles, and Hong Kong.  Additionally, we also have a physical chess board game and workbook product line called Story Time Chess, which recently won “Toy of the Year” (alongside Baby Yoda). Currently, my role focuses on the development and growth of our EdTech Platform, which I fortuitously started working on in Q4 2019. Our platform rolls all our services into one location and has allowed us to expand our reach and customer acquisition opportunities. Personally, my indoctrination into the world of chess did not start off with the typical “how the pieces” move, but rather by observing a checkmate pattern, or “line.” My journey started with the end. We use this same framework when teaching our students. We use a narrative-based format that teaches students aged 3-93 how to play and love chess – always teaching the why before the how. For example, one of our characters, King Shaky, is so afraid. He is afraid of the birds, the bees, the ABC’s, the 123’s, and even stinky cheese. He is so afraid that he tip-toes around his kingdom. So, we first ask the students about how they think King Shaky moves – fast or slow? Many steps, or one very slow step at a time? When they say one slow, quiet step, we ask “why?” To which they easily explain, “because he is so afraid!” This is how the students learn that the King moves one step at a time.  

Our company is a tight-knit group, and I would be remiss if I did not thank all my coworkers and colleagues who have sacrificed so much to allow our company to be what it is today – to all of you:  thank you. The future is unwritten, but it is simply a joy to work for an organization where everyone is swimming in the same direction.

For simplicity’s sake, I’ve chosen to detail my experience with chess in the format of a timeline.

Chess Timeline:

1995: The Beginning: Observed first chess game, learned first checkmate (before really understanding how pieces moved).

1996-2002: The Chess Glory Days: Chess sleepovers, Chess Tournaments, basically just as much chess as my loving parents would allow. In 2002, a classmate and I would win the Alabama State Team Chess Championships.

2003-2008: A Chess Hiatus: I attended a boarding school in Alabama called Indian Springs School, where alongside my studies, I ran Cross Country and played Soccer. Didn’t have time for chess, unfortunately.

2008-2010:  Don’t call it a comeback: Instead of playing college soccer, I ended up signing with Ford Models, moving to NYC, living in a model apartment (yes, like in Zoolander), and walking the runways – oh, and playing chess in the parks. During this time, I would meet one of my life’s most inspirational mentors, the self-proclaimed “Legendary Cornbread,” a Washington Square Legend.” If you are ever bored, look him up on YouTube for a good laugh – you won’t be disappointed.   

2010-2013: Degree #1: I returned to Alabama where I received my first business degree, from The University of Alabama (Roll Tide). During this time, I’d help the school launch a program called “Every Move Counts,” an initiative aimed at providing chess instruction and opportunities to under-resourced local elementary students.

2013-2014: The Return to NYC Part 1: I would work as a sales specialist for luxury cashmere behemoth Loro Piana, a company under the LVMH umbrella. I was chosen to speak to the company about our product line using a lens that I was passionate about. Of course, I used Chess to describe our most important textiles, relating the importance of the Queen in chess to one particular sales initiative that the firm was pushing that quarter.

2014-2018: Taking a Chance of Chess: During this period, I would decide to join a startup called Chess at Three. I was weighing up weather to join the startup or work for a more traditional firm, and needed advice. I went to Cornbread, who quickly replied to my thoughts, “why can’t you do them both? Hustle as hard as you can.” So during this period, I would teach chess M-F after 4pm and on the weekends and wear a variety of hats for the company. Additionally, during the week, I  would work as a financial analyst and broker for Brown Harris Stevens and Compass Real Estate. Long days, short years.

2018-2019: Hong Kong says “Yes to the Chess”: We partnered with an investor to take our offerings to Hong Kong. I thought, “why not?” We started from scratch, formed a few partnerships, hired a few tutors, and were officially in business. During this period, you could find me in my 250-sqft-high rise apartment in Sheung Wan, HK, trying to crack the code of the GMAT. Took me a couple hundred hours, but eventually the patterns became clear, and I achieved a score that I felt represented my abilities.

Adam and the Queens of Hong Kong, Wong Chuk Hang, Southside, Hong Kong Island.

2019-Current: The Return to NYC Part 2: I’d come back to NYC once more. After receiving admission to a few different MBA programs, NYU Stern was the obvious choice. It had nothing to do with a proximity to the Chess Paradise that is Washington Square Park, I promise….

The Stern network has proved immensely helpful as we brave the uncharted waters of the “new-normal.” The ideas, tools and tactics learned at Stern pour into our offerings and help us help others in such an impactful way.  Professor Larry White’s Microeconomics Class informed our pricing structures, Anat Lechner’s Leadership Class informed our change management and organizational culture practices. Scott Galloway’s The Algebra of Happiness, The Four, and mostly timely, Post-Corona allowed us to gain insights on adaptability and get ahead of the inevitable changes that will shape tomorrow – timely for sure. My finance courses have informed the financial models that help us grow both effectively and sustainably. I was even lucky enough to join notable alumni, Jennifer Shahade and Fred Waitzkin (Grandmaster and Women’s National Champion, and Author of Searching for Bobby Fischer, respectively), for a zoom discussion about how Chess can be leveraged to bring joy the joy of strategic thinking to families across the NYU community.

When I was putting together my MBA application, I really emphasized the whole “develop hard skills along in combination with my existing soft skills to expand the applications of my skillset” narrative. The following is from an essay that was part of my application to Stern: “In the short-term, my goal is to utilize the superior networking and entrepreneurial skills that an MBA can provide, to expand the scope and scale of Chess at Three’s offering.” Translation: I want to come to your school, please accept this reasoning and let me in. Retrospectively, this  actually proved to be sound reasoning. The Stern effect has been profound. To my professors, classmates, the NYU administrators and broader Stern Network: thank you. If you are interested in learning more about chess or just connecting, please feel to reach me via It would be a my pleasure to connect!

I am so grateful and blessed to be apart of the Stern Community, and often marvel about the accomplishments of my classmates. It is hard to resist the urge to consider what the future has in store for us all, but I know and trust that if we continue to work hard and clearly define our goals, together, we will get there.  Many psychologists have identified the state of “flow”, or active engagement with the world as one the states most associated with happiness.  My parting wish: that we all find our flow, whatever that may be.

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