Kory Bailey Played in the NFL but Might Not Mention It Unless you Ask About It

Friends, here is this week’s episode.

Kory Bailey is unbelievably chill. A lot chiller than me. Case in point . . . Before I met Kory, a mutual friend mentioned that Kory played college football. So I asked him about that during our first conversation, which led to Kory talking a bit—only because I asked follow-up questions—about his time in the NFL and Canadian Football League.

I’ve met a few former NFL players who are very low-key about it. In Kory’s case, he says while he loves sports, that part of his life was so long ago, and he’s done so much to shape a different identity since then that’s it’s not something he dwells on.

But you better believe that if I were ever world-class at anything, I would at least be tempted to talk about it a lot more than Kory does. Props to him.

Why Don’t More Black Athletes Own Professional Sports Franchises?

I used my conversation with Kory to check my assumption that Lebron James will be at least partial owner of an NBA team before too long, that it’s just a matter of time. He seemed to agree. But that begs the question: why aren’t there already more Black franchise owners?

This article from the Guardian gave me some great context. To be lead owner of, say, an NBA franchise, you have to individually come up with 30% of the equity. With the asking price for some teams at more than $5 billion, an interested party would need $1.5 billion in liquid assets. That’s a big number.

Startups, Racial Equity, and Economic Development

We also talked about the many barriers for women and people of color who want to become tech startup founders. In 2023, Black founders received less than 1% of US venture capital funding. What I didn’t know is that “Firms owned by women or people of color manage only 1.4 percent of total assets under management (AUM)—even though there are no statistically significant differences in performance between such firms and their white- and/or male-owned counterparts.”

Kory argues that if we restructure startup financing to make it more accessible to Black women in particular, Black women and everyone else will benefit in the process. Black women-owned firms are more capital-efficient than the average startup. The structural barriers that impede their growth likewise block others. Remove those, and everyone wins.

The End of Season One of Money, Honestly

This was episode 10. Ten is a nice round number, so I used it as an opportunity to call this the end of season one. I went from having an idea for a newsletter—not a podcast—back in March of this year to having friends convince me this wanted to be a podcast instead. They were right. Then I just had to figure out how to make and distribute one. I learned a ton.

If you are podcast-curious, I’m happy to share what I now know. Drop me a line.

Thanks for listening. And see you in 2026.