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
16 Oct 2025
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
2 Oct 2025
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
18 Sept 2025
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."
4 Sept 2025
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
21 Aug 2025
We Have Enough Money To Fix Our Broken Healthcare System. So Why Don't We?
Sameer Sood is a medical doctor who is sick of the many financial limitations he’s had to confront. For example, if a patient is covered by Medicare or Medicaid, why can’t that pot of money also cover housing, which might be the best, most cost-effective prescription he could write for someone without shelter? And why can’t you use some of the finance tools of for-profit startups to fund not-for-profit, community-based work? That’s what Sameer is asking–and answering–with the company he cofounded, FwdSlash.
Sameer grew up with relatively little money and even after earning a doctor’s salary never seemed to become too attached to any of it. Of all the things he’s done so far, that may be what's most impressive.
Episode Guide
1:53 Sameer’s money origin story
6:20 A physician’s view of what’s wrong with healthcare in America
8:45 He’s a doctor and an entrepreneur and doesn’t see a difference between the two.
10:55 Feeling “bullet-proof” on $60,000 per year
13:12 Helping non-profit organizations use finance tools typically reserved for for-profits
23:59 What he really wants to buy is his time
28:27 Nine-year-old Sameer wages a schoolwide campaign to buy his family a TV
33:13 Lionel confesses his money envy
7 Aug 2025
How Do You Ethically Manage $1.5 Trillion?
Private foundations are tax-exempt entities that serve a charitable purpose. In the US, they have about $1.5 trillion in assets under management. How much, you may wonder, are they required to spend on mission-driven activities each year?
Five percent.
Which is why my friend and guest Rodney Foxworth is helping these organizations think through the other 95% and whether that part of their operations will look like every other profit-maximizing pool of money around the world or something that also supports their charitable mission.
Episode Guide
1:37 Rodney's birthday celebrations used to be known across several states.
2:53 His name sounds a little too on the nose.
4:13 Rodney's money origin story
9:50 How his firm Worthmore helps foundations, family offices, and mission-driven investors
14:28 Why these wealthy organizations need social impact advisors
18:52 The scale of the social impact industry
20:09 A generational shift driving wealthy people and organizations to better align their values and their investing
22:50 Does investing more in your mission inevitably mean making less money?
33:06 A creative example of a foundation redirecting its financial returns to low-income program participants
24 Jul 2025
The New York Times Loves Your Book. Now What?
Elizabeth Evitts Dickinson is the author of the new biography “Claire McCardell: The Designer Who Set Women Free.” Published on June 17, the book, Dickinson's first, has been praised in the New York Times, Bazaar, Elle, and other publications. Surely wealth and the high life are just around the corner, right?
10 Jul 2025
Could You Talk in Depth About Money with Your Extended Family Every Month? Tiffany Ferguson Does.
Tiffany Ferguson is fearless. On a regular basis, she voluntarily does two things that can be tough. First, she has intentional, personally revealing conversations about money, and second, she does this with multiple members of her extended family. Money, family, feelings. Individually, each of these things keeps therapists in business. But Tiffany makes a compelling case for why we all should consider having these conversations and teaches us how to do it.
26 Jun 2025
Trust Fund, Family Drama, and a Community Intervention: Union Capital's Eric Leslie
Eric Leslie grew up with a big pile of money. That money gave him a boost, but it also cast a shadow over generations of his family. Today he’s a nonprofit leader demonstrating how we can leverage financial resources and a different kind of currency to make families and communities stronger.
22 Jun 2025
Trailer
My name is Lionel. I feel a real need to talk about money. And I think you should too.
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