Money, Honestly

He Played in the NFL, But That's Not the Most Interesting or Important Thing About Him

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

The Apprenticeship that Saved His Life

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

When Your Faith is Central to Your Identity, How Much of Yourself Can You Bring Into the Office?

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

The Nepotism Issue

Is keeping a business strictly within the family--to the exclusion of everyone else on the planet who could run it effectively--ever defensible? Chappall Gage makes a decent case for why it just might be. Chap is CEO of Susan Gage, a very successful catering company in Washington, DC with more than $25 million in annual sales. Twenty-five years ago, he took over the business that still has his mom’s name. But it’s not clear if his kids will succeed him. In this conversation, you hear him grappling with the idea of whether they should succeed him. And he definitely does not want family money or unfair expectations to ruin their lives. Episode Guide 1:28 Chap and Lionel marvel at one of the most ethical people they know 4:47 Catering can be bigger and a lot more complicated than you might think 6:34 The early days of the business 13:30 His mom's company starts to reach scale 15:29 Running a business when your mom's your boss 18:41 "We want people to come work for us for life." 22:12 Why Chap had to fire some of his customers 24:45 "Money can't buy you happiness, but it can buy you a jet ski. And I dare you to be unhappy on a jet ski." 25:56 Surviving the pandemic 28:12 The prospect of passing the business down to the next generation.  "If you're gonna be a Gage at my company, you have to be the hardest-working person there."

The Reasons People Start Businesses Are Surprising and Sometimes Heartbreaking

Kate Mereand founded and ran the Office of Innovation and Equitable Development within Washington, DC’s local government. Over 10 years, she estimates her team worked with 20,000 current and would-be entrepreneurs–people who pursued business ownership to provide a service for their community, because they faced limited employment opportunities, and also because they had an idea they just had to see all the way through. But many of these brave, determined people–even when they grew sizable enterprises–kept hitting emotional and psychological walls that Kate came to realize had to do with trauma–trauma around money. Episode Guide 2:40 Kate’s money origin story growing up on a dairy farm 10:53 Founding the Office of Innovation and Equitable Development. Some entrepreneurs were focused on the dream, not the money-management necessary to facilitate it. 15:20 Creating a training around money and trauma 25:52 What do you tell a devoted entrepreneur whose idea you think might not stand a chance? 27:26 Kate confronts her own money trauma 32:27 Kate and Lionel talk about what they like spending money on 37:40 Detangling money and worth