From Basement to Boardroom: The Inspiring Journey of Sherise Pleasant, CEO of Pleasant Financial Services

How a Single Mother From the Westside of Chicago Became a Board-Certified Credit Consultant and Financial Literacy Advocate


Sherise Pleasant is not just another CEO; she’s a living testament to resilience, perseverance, and the transformative power of financial literacy. As a single mother of four, originating from the Westside of Chicago, she has defied countless odds to become the successful entrepreneur that she is today.

A Humble Beginning

Sherise spent 16 years working for the City of Chicago, always dreaming of providing a better life for her family. The basement of her home became the crucible where her dreams started to take form. It was here that she found her passion for changing people’s lives through processing tax returns and fixing credit for family and friends.

Taking the Leap of Faith

Sherise became a Board-Certified Credit Consultant in 2019 and opened the doors to an 800 sq. ft. office in August 2020. By November of the same year, she added the title of CEO to her name, heralding a new era for her and her business, Pleasant Financial Services.

Rapid Growth and Public Recognition

In what seems like a blink of an eye, her business experienced tremendous growth, necessitating a move to a larger, 1900 sq. ft. office at 9415 S. Western Ave. Suite 202, Chicago, IL. Sherise’s impact has been felt far beyond her office space. She has maintained her company’s motto to “Repair, Rebuild, and Reestablish credit while educating consumers throughout the process.” Her voice resonates not only within her community but also through the airwaves, as she’s been featured on Chicago’s Soul 106.3FM, Inspirational 1390AM, and WVON 1690AM.

A Vision for Generational Wealth

Sherise’s ultimate goal is to help others attain financial freedom. She is committed to educating people on taxes, credit, and financial literacy, ensuring that the knowledge she imparts leads to lasting, generational change. She’s not just serving her community; she aims to make a global impact.

Connect With Sherise

For more insights, follow her on Instagram @iamsherisepleasant, where she shares tips, testimonials, and the everyday journey of being a single mother-turned-CEO.

Sherise Pleasant has shown us that no matter the starting point, through dedication and education, anything is achievable. She’s not just repairing credit; she’s rebuilding lives.

Morgan Snyder

Morgan Snyder is a highly respected senior correspondent for Los Angeles Magazine. With over 20 years of experience in the field of journalism, Morgan is known for his insightful reporting and in-depth analysis of local and national issues.

Morgan began his career as a staff writer for a small newspaper in his hometown before moving to Los Angeles to pursue his dream of becoming a correspondent. He quickly made a name for himself in the industry, earning praise for his coverage of everything from politics and crime to culture and entertainment.

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