About Ashley
Ashley N. Kirkwood is a Sales & Business Coach, host of The Ashley Nicole Show, and Founder & CEO of Speak Your Way To Cash®, a three-time Inc. 5000 company.
She is based in Flossmoor, IL.
From Courtroom to CEO
Ashley graduated with honors from Northwestern University Pritzker School of Law and tried cases at Kirkland & Ellis LLP, then represented employers at another large firm.
In 2018 she left a partner-track law job and started a virtual law firm, Mobile General Counsel.
Speak Your Way To Cash®
In 2020 Ashley and her husband Chris started Speak Your Way To Cash®, a three-time Inc. 5000 company.
The company teaches credentialed experts (attorneys, consultants, licensed professionals) to land five- and six-figure corporate and university contracts, using Evidence-Based Selling® and the P.A.I.D. Method™.
Black Women Sell Live®
Black Women Sell Live® 2026 sold out in Atlanta with 1,000+ attendees.
The Ashley Nicole Show
The Ashley Nicole Show covers the legal and business tools to protect your brand, including trademarks, contracts and monetization.
Books & Recognition
Books: Speak Your Way To Cash® (bestseller), Millions From The Stage, and The Law School Hustle.
Ashley has been featured in Forbes, Crain’s Chicago Business (“20 in their 20s”), Black Enterprise, the Chicago Tribune and NBC.
Giving Back
The Kirkwood Foundation teaches students on Chicago’s West Side about legal, medical and STEM careers.