Money, Honestly

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 gro...

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 c...

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 st...

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...

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 se...

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-p...

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 operatio...

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?

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 con...

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.

My name is Lionel. I feel a real need to talk about money. And I think you should too.