What is educated guesses?

It’s actually seven sites in one. Click here to learn about all the exciting, entertaining and engaging content we offer.

What is educated guesses?

educated guesses - carefully crafted and curated words, stories and discussions about culture, race, identity, community and family from a family of Guesses. #WordsMatter, #StoriesMatter


If you believe the old saying, “sticks and stones may break my bones, but words will never hurt me”, then you must also believe in the converse - “ hugs and kisses may warm may mend my heart,  but words will never heal me”.

Words hurt and heal.


At its most irreducible essence, stories are just a collection of words.  However, stories are essential to how we as human beings make sense of the world that we live in; how we view ourselves as well as others.  

If a picture is worth 1,000 words then a well crafted 1,000 word story can generate 1,000 pictures in a reader’s mind.

Our goal it to use words and  the collection of words - stories, to heal and generate moving pictures of possibilities in the reader’s mind that will leave them better off than when they came.

What kind of content do we offer?

educated guesses is really several sites in one:

Articles - we offer articles on a broad range of topics , but our focus is in the cultural space, particularly black culture, the black family experience and race relations. There will be both public and premium articles available.

Opinions - we offer opinion pieces that often raise more questions than they attempt to answer. The pieces are always written in a way that seeks to find a foundation of common ground from which difference can be discussed and therefore better appreciated. There will be both public and premium opinions pieces available.

Stories - in one way or another, every piece on the site is a story. But, we are very interested in intentional storytelling, particularly fiction. We will offer a steady diet of short stories, poetry, Six-Word Stories and serialized novels. There will be both public and premium stories available.

What are the series on educated guesses?

Fairytale Mixtape

(FairytaleMixtape.com) - is a series of 30+ short stories in celebration of the 30th anniversary of the marriage to my wife, Cheryl. The stories are about a boy and a girl and their lives together as man and wife. There is a story from each year of their marriage. Each story centers around a song from that year that has some level of significance in the boy and girl's life. The full series is available to paid subscribers.

8 Bars With:

(8barswith.com) - is a series where we offer up 8 questions to a special guest for them to ponder and freestyle on. The questions aren't necessarily questions as much as they are prompts or linguistic ink blots meant to stimulate thought.  The responses can be short and pithy, long and loquacious or somewhere in between. The full series is available to paid subscribers.

Big Mama’s Blog

(BigMamasBlog.com) - is a series of articles, stories and advice from Cheryl Peterson Guess, the matriarch of the educated guesses, who along with her husband Andre, raised 4 children to be well adjusted members of society with a healthy sense of self. Over the years, she has been constantly asked to dispense advice on all kinds of topics from parenting, recipes, matters of the heart, celebration ideas, healthy living, fitness, home health remedies, you name it. Now she is bringing those stories and advice to the world with her blog.

Still We Rise

(Still-We-Rise.com) - is a series of articles, stories and interviews by Kennedy Kehaulani Guess on the resiliency of the human spirit. Kennedy will seek out individuals and help them tell their stories of resilience about how they have and are continuing to overcome adversity against the odds.

Nita’s Blend

(NitasBlend.com) - is a series of articles, stories and advice from Kenithia Avery, a busy mom of a blended family.

The Chance and Me Chronicles

(ChanceandMeChronicles.com) - is a series of short stories about the adventures and antics of a young boy and his older brother Chance growing up in the 1970’s and 80’s. 


(TheBigwhiteLie.org) - is a series of articles and essays on the perpetuation of white supremacy in America. #TheBigwhiteLie is the term that we coined as the actual term for white supremacy. The articles seek to uncover the underlying truth that the #TheBigwhiteLie has sought to obscure.

Short Stories

We periodically publish short stories from members of the educated guesses family.


We periodically publish poetry from members of the educated guesses family.

Who are the educated guesses?

Andre Kimo Stone Guess is the patriarch of the educated guesses. He is a writer and cultural critic from the Smoketown neighborhood in Louisville, Kentucky. He was VP and Producer for Jazz at Lincoln Center in New York and CEO of the August Wilson Center for African American Culture in Pittsburgh. He now runs GuessWorks, Inc. with his wife Cheryl. They have four children.

He has been writing for nearly 30 years. His work has been published by the Courier-Journal, USA Today, TheGrio.com, TheRoot.com,  AURN.com, Medium.com CultureofChrist.org and ESPN’s TheUndefeated.com. 

Cheryl Peterson Guess is the matriarch of the educated guesses. She is a former speech language pathologist. She is the Chief Logistics Officer for GuessWorks, Inc. She is a member of Alpha Kappa Alpha Sorority, Inc.

Kenithia Avery is the eldest child of the educated guesses. She is married and has her hands full with a blended family of four children. She is a financial services professional.

Wynton Kelly Stone Guess is a composer, pianist, poet and writer. He has a bachelors in classical composition from Boston Conservatory and a masters in classical composition from The Royal College of Music in London. He currently lives in Lisbon where he is working on a Ph.D. in History.

Kennedy Kehaulani Guess is the self proclaimed middle child of the educated guesses. She is a second year graduate student at the University of Houston working on a masters in Speech Language Pathology. She has a bachelors in Communication Disorders from the University of Kentucky. She is a member of Alpha Kappa Alpha Sorority, Inc. She is a staunch advocate for mental health and victim’s rights.

Morgan Leilani Guess is the youngest of the educated guesses. She is a senior at Berea College in Berea, KY where she is majoring in African American Studies and Spanish. She plans to go to graduate school to pursue a doctorate in either psychology or social work.

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