T
Tiffany Hamilton
3
APPEARANCES
1
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Sep 3, 2026
"I can Fight" w/Tiffany Hamilton
11:36
11:49
24:08

Cal GrayHOST
So you talk about, you know, you had to build up this exterior and things of that just to protect yourself, right? Where did you get those tools to build that up?

Tiffany HamiltonGUEST
I would say a part of it, the streets taught me the tools, right? So like, how is this person with very few means who is super meat? Like when I look at the bullies, what tools are they using to be able to survive? And then I realized, okay, so everybody has insecurities that they're hiding in some way, shape or form.
12 MINS LATER

Cal GrayHOST
What was college like for you stepping in, just getting on campus and going to college?
Pursuing Passion Over Money / The Gray Area Podcast
0:28

Tiffany HamiltonGUEST
I was pursuing money and not necessarily pursuing the thing that my skills were most aligned with.
Got 'Em. / The Gray Area Podcast #thegrayareapodcast
0:00
0:07
0:15
0:19

Tiffany HamiltonGUEST
I don't want it to be lost on the listeners, though, that piece around the insecurities and how they can drive the decisions that you make.

Tiffany HamiltonGUEST
Even when I think about connecting with my daughter's dad at that time, Tiffany was considered, I wasn't the prettiest girl.

Tiffany HamiltonGUEST
So I'm like, I'm going to put in my mind, I'm going to get the finest dude in middle school.

Tiffany HamiltonGUEST
Why was I thinking like that? Like, y'all think I'm ugly, but watch me pull.