Report Details

What is Pollyanna Inc.?

Pollyanna Inc. is a 501(c)(3) nonprofit organization. According to its website, Casper Caldarola established Pollyanna in 2015. She was a trustee at the Dalton School, a private school in New York.

The company has stirred controversy for its trainings largely in private companies.

It describes itself as a company that “advances systemic change by developing stronger communities.”

On its website, it says its strategy is to work with “academics and other institutions to achieve their diversity, equity and inclusion goals.” It says, “Through its unique conference models, discussion platforms, and racial literacy curricula, Pollyanna increases cultural competence.”

The City Journal reported in January 2021:

Over the past several years, Pollyanna has spread quietly through the toniest schools in New York City and across the country. Buoyed by last summer’s protests, it tripled its clientele to over 60 schools in 2020, stretching from Harvard-Westlake in Los Angeles to remote Vermont Academy. That includes some 25 schools in New York—hyper-exclusive institutions like Dalton, Horace Mann, Spence, and the Hunter College Elementary School.

What services does Pollyanna Inc. provide?

Pollyanna sells services that include “assessments,” conferences, curriculum and workshops.

Its services include:

  • “Racial Literacy Workshops,” with “presentations and workshops that re designed to help schools, organizations and corporations engage with Diversity, Equity, and Inclusion initiatives and enhance racial literacy knowledge and equity practices.”
  • The workshops for parents and guardians include “Making an Antiracist Home” and “Friendship, Connection, and Racial Justice.”
  • “Athletics Department Workshops” include “Scenarios and Strategies for Addressing Implicit Bias and Microaggressions in Sports” and “Impact of Implicit Bias on Athletics: The Locker Room, the Practice Field, and Gametime.”
  • “Faculty & Administration Workshop” include “Racial Literacy 101” and “The Teacher’s Toolkit for Teaching About Race and Racism in the Classroom.”

Recommended speakers include many consultants, including: Jennifer Fryant, founder of Team Finch; Derrick Gay, diversity and inclusion consultant; Rodney Glasgow, director of the National Diversity Practioners Institute; Jason Caige Harris, “educator,” “mediator” and “strategist”; Debbie Irving, “racial justice educator” and writer; Rosetta Lee, “outreach specialist”; Philip McAdoo, LGBTQ advocate and “diversity consultant”; Ali Michael, director of Race Institute; Glenn Singleton, president of Pacific Educational Group; and Liza Talusan, “strategic partner and facilitator.”

What K-12 work does Pollyanna Inc.?


According to the City Journal in March 2021:

Brearley is one of more than 40 schools to partner with Pollyanna since last July, including 19 in New York City. Pollyanna offers these clients services including DEI “assessments” and workshops on topics like “microaggressions” and the pseudoscience of implicit bias. Grace Church School, for example, has contracted with Pollyanna to conduct an assessment, while a number of schools, including Dalton and Allen-Stevenson, are incorporating the “racial literacy” curriculum into their classes.

Dalton School

In late January 2021, a group of alumni and parents wrote an anonymous letter concerned about curriculum at the school, in the wake of “an obsessive focus on race and identity,” emerging out of training of Pollyanna Inc. The letter was first reported by the blog, The Naked Dollar.

The City Journal later reported:

The consultancy’s “racial literacy” curriculum, the letter claimed, “has already permeated Dalton classes from social studies to science” and contributed to “some of the worst abuses this year”—incidents like the one in which a Jewish student was forced to play the “racist cop” in science class, or the art class on “decentering whiteness.”

Wheeler School

The Wheeler School in Rhode Island “partnered” with Pollyanna Inc. to host a one-day conference, called the 2021 Wheeler (Virtual) Diversity Conference, exploring “Identity and Belonging.”