Grandmaster Maurice Ashley — The Path and Strategies of World-Class Mastery (#449)

“Once you get to the top of the mountain, you look around, and you get your chance to look. And now what? You’ve got a nice view. That’s great. How long can you stay on the mountain? You need another mountain.”

— Grandmaster Maurice Ashley

Maurice Ashley (@MauriceAshley) made history in 1999 when he became the first African-American chess grandmaster. He is a three-time national championship coach, author of Chess for Success: Using an Old Game to Build New Strengths in Children and Teens, ESPN commentator, iPhone app designer, puzzle inventor, and motivational speaker.

Maurice is well known for providing dynamic live tournament coverage of world-class chess competitions and matches. His high-energy, unapologetic, and irreverent commentary combines Brooklyn street smarts with professional ESPN-style sports analysis. He has covered every class of elite event, including the World Chess Championships, the US Chess Championships, the Grand Chess Tour, and the legendary “man vs. machine” matches between Garry Kasparov and IBM’s Deep Blue.

Traveling the world as an ardent spokesperson for the many character-building effects of chess, Maurice consults with universities, schools, chess clubs, executives, and celebrities on how chess principles and strategies can be applied to improve business practices and assist with personal growth. Maurice also acts as a master of ceremonies and inspirational speaker at business conferences and high-class chess events.

Maurice has received multiple community service awards from city governments, universities, and community groups for his work. In recognition of his immense contribution to the game, he was inducted into the US Chess Hall of Fame in 2016 and the Brooklyn Technical High School Hall of Fame in 2018.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform. 

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#449: Grandmaster Maurice Ashley on the Magic of Chess, The Art of Trash Talking, Must-Read Biographies, and More

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with our mutual friend Josh Waitzkin? Have a listen to our most recent conversation in which we discussed his own relationship with Maurice, approaches to learning, the benefits of being a beginner, why feedback loops are game-changers, unorthodox skill acquisition, and much more.

#412: Josh Waitzkin on Beginner’s Mind, Self-Actualization, and Advice from Your Future Self


  • Connect with Maurice Ashley:

Website | Twitter | Facebook | Instagram


  • The Maurice Ashley origin story. [06:59]
  • Competition runs strong in the Ashley family. [09:55]
  • Why did Maurice’s family make the move to the US from Jamaica? Why did it involve a separation from their mother for 10 years, and what was it like to finally be reunited? [12:02]
  • What neighborhood in the US became home, and how did chess enter the picture for young Maurice? [15:29]
  • How a library book and a worthy opponent changed the way Maurice thought about chess. [18:17]
  • What was the Black Bear School? [19:58]
  • Blitz chess vs. classical chess. [23:25]
  • The Maurice Ashley guide to trash-talking. [25:46]
  • As the youngest member of the Black Bear School, what did Maurice see as the biggest setback keeping his older peers from truly excelling, and how did he evolve after “graduating” from their ranks? [30:18]
  • How did the atmosphere of a venerable chess club compare to what Maurice had, up to that point, been used to? [32:53]
  • Frustrated along the way on his quest to become a Grandmaster, what did Maurice learn from Tiger Woods that kept him in the game? [33:45]
  • At this time, how did Maurice’s frustration and depression around getting stuck in a rut transmute into the inspiration he needed to emerge from that rut? [36:04]
  • How does someone become a Master, Grandmaster, or any title in between? [39:29]
  • After teaching, commentating, and writing, how did Maurice get back into training shape to pursue his Grandmaster goal — and what technological advantage did he have in 1997 that he didn’t have in his Black Bear School days? [42:30]
  • How does Maurice suggest building mental and physical stamina for high-level chess (and why might you be hard-pressed to find a top-level player who could be considered overweight)? [47:00]
  • How does Maurice tie the disciplines of aikido and chess together? [50:38]
  • How did the experience of finally achieving the coveted Grandmaster title hit Maurice? What was the view like from the top of that mountain, and where could he possibly go after that? [53:31]
  • How does Maurice get kids hooked on chess, what does he get out of teaching, and what have been his most memorable teams? [57:02]
  • Why has chess remained popular for 1,500 years –and even seems to be increasing in popularity in the age of COVID-19? [58:31]
  • What would Maurice suggest to a relative chess beginner who doesn’t necessarily aspire to be a Grandmaster, but just wants to become competent at the game? [1:01:37]
  • Using puzzles to expand your repertoire and confidence. [1:03:38]
  • Recommended reading (for chess and general inspiration). [1:05:49]
  • How Maurice is processing the social unrest of 2020. [1:13:29]
  • How would Maurice hope to offset the tyranny of the majority in a way that makes America more just and equitable for all Americans — not just most Americans? [1:19:29]
  • As someone who’s spent time as an educator, where does Maurice feel our current educational models are most woefully lacking? [1:24:40]
  • How nonprofits DonorsChoose and QuestBridge are trying to help provide resources to teachers and students in underserved communities — now even more in need during the COVID-19 pandemic. [1:29:49]
  • Maurice expands on books he was kind enough to mention in Tribe of Mentors as having an impact on him. [1:33:02]
  • On being flexible, embracing uncertainty, and living out of a suitcase (though the timing might not be ideal). [1:39:50]
  • Maurice has never been afraid to say “I don’t know.” So where does salsa dancing, telenovelas, and Pluto fit into all of this? [1:42:09]
  • Parting thoughts and talking trash. [1:49:18]


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5 Replies to “Grandmaster Maurice Ashley — The Path and Strategies of World-Class Mastery (#449)”

  1. Dear Tim-

    This is a personal letter. While somewhat related this solid interview and “Once you get to the top of the mountain, You need another mountain,” I wrote it to you following your GQ interview and have tried to get it to you through other means privately, but will now post it here.

    I’ve loosely known your work for years, and used to be connected to a similar social circle to you–Camp Mystic at Burning Man, and the time, money, relationship/sexual freedom, micro-dosing, lifestyle design, entrepreneurial tribe in the Bay Area.

    I taught the work of Byron Katie, studied NLP in Marin, did Landmark stuff, all after years of a dozen + Vipassana Meditation retreats, and questing in India, Thailand, Africa…

    Ten years ago, I moved to the Nevada City, CA area, and joined a men’s group. One day, after about two months of being in the group, one of the men, a best-selling author who’d been on Oprah and knows success, came up to me and said,

    “Most every week you report that, aside from a few tweaks, you primarily have have it all together—money, career, health, relationship—and mostly try to “help” the other men in the group…
    I have been where you are, and see that you’re getting complacent, and finding your achievements aren’t doing it for you in the way they once did. If you’re interested, I know someone I could introduce to you that could show you the next challenge and the inner search you might now be looking for.”

    I went to my first talk of J. Jaye Gold, and, as they say, the rest is history.

    I heard things that I’d never heard before. As an arrogant, Bay Area personal growth connoisseur, that was really a feat. More importantly, he said things I’d been waiting to hear my whole life.

    I just read your interview with GQ. You have climbed a much bigger success and fame mountain than me, but the effects sound familiar.

    If not for COVID, I would invite you to to a talk of this man where you could sit, anonymously, and see if his words/perspectives spoke to you.

    Since I cannot, I send you these two things:
    A compilation video with short snippets from his talks, and a podcast if you prefer to listen.

    Chef, Drugs, The Prerequisite for Meditation, In These Times:
    Search YouTube for “J. Jaye Gold Compilation”

    I recommend episode 4, We Have Traded Our Depth for Variety.
    He tells a story of being thrown in jail for his gambling games he was running in NYC as a young man, and what happens to him inside:
    Justin Time: Honesty, Humor, and Perspective from An American Spiritual Master

    He charges nothing for what he does,
    and has been doing this since we were born (I was born in ’78)

    I hope you find value in his words for whatever is next for you,

  2. Chess can spring to life in a child’s mind when there is a real person behind the games. The achievements of historical and modern chess players will give students motivation and hopes for potential achievement. Students need role models as well as model games. Show games that illustrate basic checkmate patterns and tactics; plus use stories and anecdotes about the players behind the moves. I really can recommend a book, which is very good to teach kids how to play chess, writen by Makism Aksanov. It’s very easy to teach with all the fun and play, and make with this game a very rich, fantasy world for our kids 🙂

  3. Outstanding episode. I appreciate Maurice’s invigorating approach to discussing chess. Hearing him say he’d need three days with Frederick Douglass? One of my all time favorite moments on any of your episodes. I also love how he presented the majority/minority reality.

    Thank you for having Maurice on your show. Entertaining & enlightening experience.

  4. Dear Tim,

    I would like to recommend the German neuroscientist and former Harvard professor Prof. Dr. Manfred Spitzer to your show. He has done incredible work to gather and uncover the effects of digitalisation on children and adult brain development, as well as the impacts on the psychological, social and physical health. Next to the already important and discussed aspects of a healthy lifestyle such as nutrition, exercise, sleep and spirituality, he completes this field with many insights into brain development, education and the current threats of digitalisation.

    He is well known in Germany and it is time that his insights are spreading more internationally.

    It would be great to have him on the show!

    Kind regards,

  5. What a pleasure to listen to, and look forward to looking at reading the George Leonard, and Samuel Arbesman references. Thank you Tim and Maurice!