Ron Bailey is the featured guest on the inaugural episode of the Garage to Goliath | Leaders Building Legacies Podcast for good reason. Mr. Bailey changed my life for the better—he invested in me with his invaluable time, knowledge, and his generous heart.

Mr. Bailey is my mentor, I hang on his every word regarding life, business, and leadership. It’s addicting to be around Ron Bailey because of his optimism, his intentional leadership, and the value he creates for others.



Ron Bailey comes from humble beginnings in Lamar, West Virginia. He served in the Army and went on to be the first person in his family to graduate from college.

In 1974, Ron Bailey taught computer information systems at Strayer College in Washington D.C. He worked his way up from professor to head of the college’s IT department, and then on to Senior Vice President of the college.

Ron Bailey went on to buy the college and is credited with transforming a struggling Strayer College into a thriving Strayer University—taking Strayer from Garage to Goliath.

He sold his stake in Strayer University for $180 million and retired to Florida.

Mr. Bailey maintains an active and full retirement; he serves on the Board of Directors of The Palm Bank in Tampa, America’s Choice Title in Jacksonville, The University of Tampa, Special Operations Warriors Foundation in Tampa, Tampa General Hospital, The Salvation Army Tampa Command, and Cork United Methodist Church in Plant City, Florida.

Most importantly he is passionately changing lives by helping people further their education with scholarships from The Bailey Family Foundation.

He will tell you that when it’s his time to go, he wants to go broke.

Mr. Bailey’s grit, tenacity, hope, and optimism propelled him from Garage to Goliath.

He is an unassuming, humble, servant leader. He is an unsung hero of the generosity begot by free enterprise. We all have something to learn from the legacy leadership of Ron Bailey.

Lead well,

p.s. – Thanks for listening! Please rate, review, and subscribe to my leadership podcast on iTunesSpotify, and/or SoundCloud.


Related Links:


  • Ron’s Garage to Goliath story [4:20]

  • Ron talks about his big why, what motivates him even in tough times [11:30]

  • Ron shares his personal values to create success [12:32]

  • What does Ron daydream about [13:54]

  • What did Ron want to be when he was a kid [14:55]

  • Ron’s dream job [16:55 ]

  • What keeps Ron awake at night [18:14]

  • Ron’s leadership philosophy [19:44]

  • Ron explains a time when he didn’t lead well [21:42]

  • The one trait Ron looks for in his top people [23:24]

  • What Ron thinks is damaging to leaders and how to avoid it [24:23]

  • Ron describes what he thinks makes a good team [25:12]

  • Ron’s strategy to create a vision for his team [26:21]

  • A mistake Ron made and what he learned from that mistake [28:35]

  • Ron boils down the secret to his success, how he went from garage to goliath [29:56]

  • Ron talks about the importance of getting to first base v. hitting a homerun [30:55]

  • Who is in Ron’s kitchen cabinet [32:32]

  • Ron talks about how he continues to grow as a leader [34:30]

  • Ron’s advice to people who are in a leadership position for the first time [38:11]

  • Ron’s advice to his 30-year-old self [39:25]

  • Ron’s strategy to prioritize life [40:31]

  • Ron talks about how to create the correct and effective incentives to motivate a team [41:47]

  • Ron reveals his strategy to hire the right people [43:50]

  • Ron talks about how to create a successful company culture [44:40]

  • Ron tells why it’s important to create a leadership strategy [47:57]

  • Ron on how to keep the inspiration in your institution [49:31]

  • What Ron found to be the optimal level of direct reports [51:40]

  • Ron talks about staying out of the ivory CEO tower [53:16]

  • Ron talks about what makes for a strong Board of Directors [56:10]

  • Ron’s life advice for his grandkids [57:05]

  • Just one thing that would make Ron happier today [57:38]

  • How Ron defines success [1:03:34]

  • Ron talks about how his company adds value to society [1:02:32]

  • Ron talks about how to raise level headed kids [1:05:26]

  • Ron shares his perspective on prioritizing his family [1:09:39]

  • Ron talks about what it feels like to change the lives of others for the better [1:11:08]

  • Ron shares how he wants his children to describe him to his grandchildren [1:18:42]