Kory Bailey knows how to compete. As a NCAA division I athlete at what his fellow alumni call the University of National Champions; in the NFL; in big tech; and in the startup world. But as CEO of a tech accelerator, his most radical ideas are about inclusion. What if we reworked the funding and support networks for entrepreneurs so that those who have the least access can get their chance and grow?

In the venture capital world, we talk about pivoting so much that it’s easy to forget that’s not just a metaphor. Some people are nimble enough physically to turn on a dime. Across every phase of his multi-stage career, Kory has been one of those people.

Episode Guide

1:27 Kory's money origin story

5:47 Growing up in Durham, North Carolina

6:31 Upsurge Baltimore

7:36 Making startups a greater part of economic development in the Baltimore area

9:52 Baltimore is a college town that hasn't yet met its full potential

14:14 Kory's career path from selling burned CDs to playing in the NFL, working in big tech, and running a tech accelerator

18:42 Kory might not talk about his time in the NFL unless you ask him

19:48 His dad bribed him with a $20,000 car. It worked.

23:15 Figuring out his identity after sports

25:14 The University of National Champions

29:01 Learning to manage your money as a professional athlete can be overwhelming

33:21 The new financial opportunities college players have should set them up for more success later in their careers

36:39 When Lebron James becomes an NBA franchise owner, it will open that door for others

38:45 Creating a startup ecosystem where more people can succeed

Cory McCray remembers when legally earning $12 an hour was the start of something big for him. But he had no idea that would lead to overseeing $60 billion.

Senator McCray, as I like to call him, became a Maryland state legislator in 2015 and a member of the state senate’s powerful Budget and Taxation Committee in 2019.

Most people, he says, did not know him when he was in juvenile detention and can’t imagine that version of his life. Becoming a trainee electrician was the start of what his more recent friends and colleagues see today.

He titled his new book “The Apprenticeship that Saved My Life,” and he means that literally.

Episode Guide

01:34 Cory's money origin story

03:19 "I had a mom who never gave up on her son." From juvenile detention to apprenticeship.

04:26 Building wealth by following others' example. "I know I'm smarter than that guy over there!"

07:00 Using his scheduled raises to invest in real estate

09:10 "I'm gonna keep believing in you until you believe in yourself."

11:43 Why he wrote the book.

13:28 The start of his political career

16:18 A few of his political opponents tried to use his juvenile record against him

18:38 Policy wins

23:40 Fast food restaurants with bullet-proof glass

27:13 The support he gets from people who know his story

34:06 Lionel and Cory have a mentee in common, a tremendous young woman named Ky'Mera Pauling

40:49 On paper, his job in the Maryland Senate is part-time, but it displaces other work and income-producing activities he might pursue

Adrian Bracy was chief financial officer for the Arizona Cardinals, an NFL team now worth five and a half billion dollars. Today she is a full-time advisor to one of the wealthier families in the country, helping guide their business and philanthropic operations. Billionaires listen closely when Adrian speaks, but her first and deepest loyalty is to someone with even more clout: God.

Adrian has structured her exceedingly impressive career around conducting business and pursuing her religious convictions at the same time. Each reinforces the other.

As you will hear, she knows the danger of putting that aspect of her identity front and center but decided long ago that it was worth the risk. Actually, given the strength of her convictions, I’m not sure she felt there was any choice in the matter.

Episode Guide

1:30 The first thing she wanted to do with her money was give it to the church

10:21 Her job is to help a wealthy Christian family perform good works with their money

13:58 Relatively few wealthy Black families have their own family office to organize their financial affairs

18:37 You might own an NFL franchise, but that doesn't mean you can pay all of your bills

24:35 The dangers of discussing faith in the workplace

30:07 People keep coming to her with their problems, and she likes that

33:15 She takes her own advice when it comes to budgeting and estate-planning