Fab 5 Freddy — graffiti pioneer, first host of Yo! MTV Raps, and author of Everybody's Fly — on how he trusted what he saw in hip-hop and graffiti before the world caught up.

Fred Brathwaite walks Leilani Brown back through it all: a Brooklyn jazz childhood with Max Roach as his godfather, calling Thelonious Monk's house from his dad's phone book, teaching himself art history in New York's museums, finding Lee Quiñones, meeting Jean-Michel Basquiat when he was still SAMO, the Keith Haring and Andy Warhol years, making Wild Style — hip-hop's first film — with no blueprint and no American money, and founding B Noble after Bernard Noble's 13-year sentence for two joints' worth of cannabis.

His answer for anyone building something nobody understands yet: give it a go, then give it a go again.

📕 Everybody's Fly — wherever books are sold

🌿 B Noble: https://bnoble.com

📘 Free Reset Guide: https://resetguide.giantstepsllc.com

🌐 giantstepsllc.com

Dr. Shirley Collado, President & CEO of College Track and President Emerita of Ithaca College, left the presidency of a college she loved to lead the nation's leading college completion program for first-generation students. She talks with Leilani about growing up in Sunset Park, the bus ride to Nashville, what it costs to be "the first," and why the younger version of herself would have said no.

Shirley Collado is one of my closest friends, which made this conversation harder to do than most. When you know someone well, you worry about glossing over the things you assume everybody already knows. So I started where her story starts: a seventeen-year-old in Sunset Park, Brooklyn, who expected to stay in New York and commute to Hunter.

Here's what the bios tell you. Dr. Collado is the President and CEO of College Track, the nation's leading college completion program for first-generation students. She's President Emerita of Ithaca College, where she was the ninth president, the first person of color to lead it, and the first Dominican American ever to lead a four-year college or university in the United States. Before that she was dean of the college at Middlebury and an executive vice president of the Posse Foundation, years after joining the very first Posse class herself.

Here's what the bios don't tell you. Her father drove a cab he kept spotless, and the family detailed it every Sunday. Her mother worked in a garment factory. A youth counselor opened a Vanderbilt viewbook in a basement in SoHo and asked if she'd go if she got the scholarship. Her mother rode the bus to Nashville with her, spent two hours moving her in, and rode it home.

Then we get to the harder part. Shirley left a college presidency she loved, one of the most complicated CEO seats in the country, to lead College Track. We talk about the pressure to stay when you're the first, and when you're first-generation and everyone around you needs you to hold the place you worked so hard to reach. We also talk about who she turned to for the truth, and the part of the decision that was about love as much as career.

This season I'm asking every guest the same question: what became possible? For Shirley, the answer is a ten-year program that walks thousands of first-generation students from ninth grade through college and into a career.

Let's press play.

—Leilani

Links:

College Track: https://collegetrack.org

Dr. Shirley Collado: https://shirleymcollado.com

Dr. Shirley Collado on LinkedIn: https://www.linkedin.com/in/shirley-m-collado-ph-d-420a38196/

If you've been sitting on a decision, whether it's leaving the job, starting the thing, or betting on yourself, this show is for you. What became possible? That's the question. Follow wherever you listen.

Free Reset Guide: https://resetguide.giantstepsllc.com

Website: https://giantstepsllc.com

I've known Kim Alexis Newton for years. I pulled her aside once, a while back, and asked her what she was doing next. She told me she was building a portfolio career. I didn't fully understand what that meant then. I do now.

For two decades, Kim ran a piece of a billion-dollar business inside Hallmark Cards. On paper, nothing was wrong. She just didn't feel like she was meeting her full potential — so she bet on herself.

What she'd been doing quietly on the side for twenty years, taught to her by her grandmother, turned out to be the thing: quilting. A chance introduction to former WW International CEO Mindy Grossman led to her first sale — a piece that ended up in Oprah Winfrey's collection. That moment became a fine art practice, a book (The Intentional Pause), a framework she calls F.O.R.E.S.T. for facing the fear that keeps people stuck, and a return to the boardroom, on her own terms.

This season I'm asking every guest the same question: what became possible? For Kim, it's a gallery show, a business, a board seat, and a body of work that outlives any single job title.

Let's press play.

—Leilani

Links: kimalexisnewton.com · alexisgiftquilts.com