Nationwide — Ashley Kirkwood, a former trial lawyer who walked away from a $300,000 partner-track legal career to become an entrepreneur, has reached a major milestone with her growing sales training company. Her upcoming Black Women Sell Live® 2026 conference has already sold tickets to 1,000 Black women entrepreneurs and professionals from across the country. The three-day event will take place September 25–27, 2026, at the Omni Hotel in Atlanta, Georgia, with tickets starting at just $199. Her company, Speak Your Way To Cash®, has also earned a place on the Inc. 5000 list of America’s fastest-growing private companies for three consecutive years.
Kirkwood founded Speak Your Way To Cash® in 2018 after leaving her career as a federal trial attorney and Northwestern Law graduate who worked at Kirkland & Ellis. Her first Speak Your Way To Cash Live event drew only 10 people, making the growth to a 1,000-person conference especially significant. Today, her company trains credentialed experts, licensed professionals, and service-based entrepreneurs to win corporate contracts, sell their expertise, and generate revenue through speaking. This year’s Black Women Sell Live®, themed “Fight Back,” is designed to give attendees practical strategies they can immediately use to grow stronger and more profitable businesses.
The conference will feature an unusually accomplished group of entrepreneurs, investors, executives, and business leaders. Billionaire entrepreneur Dr. Trisha Bailey, founder of Bailey’s Medical Equipment and Supplies, will share lessons from building an enterprise that now includes multiple companies across medical equipment, pharmacy, and real estate. Adesuwa Okunbo Rhodes, founder and managing partner of Aruwa Capital Management, is traveling from Lagos, Nigeria, to teach attendees how to build businesses that investors want to fund and discuss opportunities for investing in Nigeria. Other speakers include sales trainer and Sisterpreneur® Inc. CEO Linda Clemons, Commas founder and CEO Yash Daftary, and HighLevel Senior Director of Marketing Communications Piper McCoy.
Attendees will also hear from descendants of two of the most important Black women entrepreneurs in American history. A’Lelia Bundles, journalist, author, and great-great-granddaughter of Madam C.J. Walker, will explain the marketing and sales strategies that helped Walker build her historic business empire. She will be joined by Liza Mickens, the great-great-granddaughter of Maggie Lena Walker, who became the first Black woman to charter a bank in the United States in 1903. Together, they will explore how Black women built, marketed, financed, and sold their businesses generations ago — and which of those principles remain relevant to entrepreneurs today.
Black Women Sell Live® is structured as an intensive working conference, with sessions running from 9 a.m. to 9 p.m. and speakers answering questions directly from attendees. On the final day, participants will spend 90 minutes developing a one-page sales plan, one-page marketing brief, and one-page operations brief that they can take home and implement during the fourth quarter. The experience will also include a live performance by BET Sunday Best season seven winner Geoffrey Golden and a message from Andrea Clayton, while Kirkwood will debut her new curated eyeglass collection, See Your Way To Cash™. The conference is ADA accessible, with sign language interpretation provided throughout all three days, and sponsors are helping fund $199 “Justice Tickets” to make the event more financially accessible.
“Black women have never had a problem building. We have a problem getting funded, getting bought from, and getting paid what the work is worth,” Kirkwood says. “So we brought in the women who solved it — a woman who scaled a medical supply company into an empire, a woman in Lagos writing checks to founders, and the descendants of two women who did it in 1903 without the right to vote. Nobody is coming to save us. We are going to sell our way out.”
Black Women Sell Live® 2026 will be held September 25–27 at the Omni Hotel in Atlanta, with 1,000 attendees confirmed and fewer than 80 seats remaining at the time of the announcement. For tickets and additional information about the waiting list, visit BlackWomenSellEvent.com
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