On this episode of Gen X Amplified, I am joined by Stephen Bailey, Stephen is the CEO and co-founder of ExecOnline, a corporate training company that partners with the world’s top business schools to offer leadership development on demand to enterprise organizations.
ExecOnline is on a mission to connect all leaders to their future potential by disrupting and democratizing corporate learning.
Some of ExecOnline’s Partner schools include Stanford, Wharton, Berkeley Haas, Chicago Booth, UVA Darden School of Business, Columbia, Duke, MIT-Sloan, Yale, and others.
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YouTubeIn this episode, Stephen and I unpack:
- Stephen’s career journey from “recovered lawyer” to startup founder and eventually becoming the co-founder and CEO of ExecOnline
- The “aha moment” from Stephen’s experience as the CEO of a previous startup that led to launching ExecOnline
- The under-representation of African-Americans in venture-funded startups—and why this must change.
- The key difference between mentoring and learning.
- How large language models and generative AI are shaping the future of the learning economy.
- Stephen’s deep and loyal connection to New Orleans (where he was born and raised) and his passionate allegiance to Lil Wayne.
- A discussion on whether Stephen’s wife, top chef Adrienne Cheatham is Gen X or a Millennial.
- And more!
Stephen’s Personal Theme Song
“Right Above It” (feat. Drake) by Lil Wayne
About Stephen Bailey
Stephen is the co-founder and CEO of ExecOnline, a B2B corporate training company that partners with the world’s top business schools to offer leadership development on demand to enterprise organizations.
Its mission is to connect all leaders to their future potential by disprupting and democratizing corporate learning.
When Stephen launched ExecOnline, his vision was to combine the engagement of traditional on-campus and role-based applied learning — with the convenience and scale of an online experience—for all levels of leadership.
Therefore, creating a more diverse, equitable, and inclusive leadership pipeline within the world of work.
ExecOnline has been named to the Global Silicon Valley EdTech 150, and also recognized as a “Technology Company to Watch” by Forbes.
Prior to ExecOnline, Stephen served as the CEO of Frontier Strategy Group (FSG), a software and information services business.
He grew FSG from an early-stage start-up to a company that served nearly half the Fortune 500 across a range of international markets and business functions. Prior to his role as CEO, he was FSG’s first Chief Product Officer.
Before joining FSG, Stephen was an associate in the venture capital and private equity group of WilmerHale.
Stephen is also the Board Chair of the Truman Center for National Policy and member of the Board of Prospect Schools, a charter school network in NYC.
He graduated Phi Beta Kappa and summa cum laude from Emory University and holds a JD from the Yale Law School.
Stephen has been an EdTech pioneer and champion of the “learning economy” ever since he recognized the vast leadership gap many years ago.
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