About This Episode

In this episode, Tiffany Hamilton, CEO of YWCA White Plains and Central Westchester, discusses her path from teen motherhood and a technology career into nonprofit leadership. She and the host talk about turning adversity into advocacy, navigating today's DEI climate, leading with faith, authenticity, and heart, and the moments she tried to walk away from this calling before finally saying yes.

Listeners will take away a resilience-minded approach to leading through difficult and disruptive seasons rather than waiting for calm to arrive. Tiffany's journey offers mission-driven leaders a blueprint for saying yes to purpose even when the timing feels far from convenient, and for leading with authenticity when the pressure to perform is highest.

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[0:00] Introduction And Not Wasting A Crisis

[3:43] Being Tapped To Lead A New Organization

[5:32] Young Tiffany Growing Up And Early Lessons

[7:23] A Teacher Encouraging Her Onto The Debate Team

[11:09] Teachers Who Poured Into Her Early On

[16:38] Lived Experience Becoming A Resource For Others

[20:44] Showing Up Authentically In Her Purpose

[22:18] First Thirty Days Facing A Heating Failure

[28:08] Ensuring Families Can Eat And Survive

[33:19] Combining Identity With A Sense Of Purpose

[41:25] Shifting Her Mindset Through Rest

[44:59] Understanding Facts Around Diversity And Inclusion

[48:41] Balancing AI With Human Thinking

[59:37] What She Hopes People Say About Her

Episode Transcript

[0:00]  They tell you a good leader never let lets a crisis go to waste. I needed that c I didn't look at it as a crisis. I looked at it as a gift because had it not been for that, I would not have been able to see all of the deficiencies in some folks and the strengths in others.

[0:18]  You can tell a person, you can tell the leadership of a true person not by how they respond when things are well, but how they respond when the when the stuff hits the fan. Right. And that's exactly what I was gifted with. And so how I survived that, I changed my mindset first. This is not a crisis. This is a gift. And what am I what what's being revealed to me in this time? And then obviously I'mma lean on the word because I went through a fast to come to say yes to this place. And then I had to reminded the weapons were formed, but they'll never prosper. So I already knew in the end I would win. So if you begin at the beginning of a crisis with a victor mindset versus victim, you cooking with gas at that

[1:20]  point. Welcome back to another episode here on the Heart and Hustle podcast. And let me tell you, when I first spoke to this lady, it was a it was a vibe. Okay? So, you might want to get your popcorn ready, maybe some tissues, because we might tell you some stories that could really touch the hearts. But I really want to ask you something, listeners. Have you ever been in a space when you say no, right, twice and and still won't leave you alone? Well, today's guest didn't just walk into leadership. She answered a call she tried to ignore twice. Tiffany Hamilton, welcome to the show. How you doing today? I am fantastic. I am fantastic.

[1:54]  Thank you for having me. Super excited for our time together today. Same. Same. Listen, um, like I told you right before we hit record, I had to go look back at our previous call and even though it was 15 minutes, it felt like we spoke for a very long time and we got to learn about each other. Um, and and really realized that we both have overcome adversity.

[2:14]  when people counted us out and um let us made us feel small, we showed up in a big way where now we're leading uh and making big impacts, right? So, so I ask you, we kind of go back into those Kansas City roots, tech, higher ed, now you're a CEO of a nonprofit on the front lines of racial and gender justice.

[2:35]  Tiffany, what in the world was going on in your life when this road just kept knocking knocking? By the third time, you're like, "Wait a minute, what's going on here?" Yeah. You know, I I think my journey is like everybody else's, right? You hear that in order to achieve the American dream, you go to school, you get the career, and once you get the career, um, things will will settle for you. But I guess I've never been the person to take the the regular way to an end goal. And so for me, by the time I get into this role, I had already deviated from my original career, right? So, I went to undergrad and I majored in computer science for three and a half years. So, inside of here is like a geek that loves tech.

[3:20]  But, um, it was my experience in undergrad that led me to higher education administration as a first generation college student. I was a a full-time college student, threequarter worker, and a full-time parent all at undergrad. So, for me, I was like, I got to make this place better for somebody else that might try to do the same thing. So, I spent 20 years in higher ed. So, at that point, I'm comfortable.

[3:43]  Money's good, right? The the impact is good and I have a rhythm. But then some folks tapped me on the shoulder and was like, "There's this organization that I think would be good for you." Was like, "For who?" Cuz good, right? But, um, I was like, "No, I'm building, you know, the division of diversity, equity, and inclusion at this institution, building out the team, building out the infrastructure." Couple of months later, another tap from a different community member like, "Listen, I think you need this." And I was like, "I don't because the salary again, I was driven by dollars." Not understanding my assignment on this earth was never about dollars. It was always about impact. And so, uh, by the third time they came around, I was like, "All right, I'mma have to consult somebody bigger than

[4:30]  myself, right? Because usually I think I can I can make some pretty good decisions. I kept a kid alive 29 years. my decision making still seem to be okay, but um I I I'm a woman of faith, so I had to to pray about it like persistently uh for a period of time to get out of flesh and to really get focused on uh what my assignment was.

[4:51]  And so coming out of that space, it was affirmed um I'm an answer. And what good is an answer if there are no problems? and where I was because I built it had a flow. You know, there were challenges but there were no problems. And so the gift that I have is to to to be an answer not to everything. And so I came out of that space and and threw my hat in the ring and then it basically they took me from the lambs to the lion's den. Not to do a biblical podcast, but that's exactly how it felt, right? But yeah, I love it. We're about to get there. We about to get there because I definitely want to talk about um you talk about challenges. Oh, you walked into some challenges. There was definitely those.

[5:32]  But I want to just take us back even further. There was this young Tiffany. You know, what was young Tiffany like growing up and what lessons did she really carry as a little girl into into womanhood? I can only imagine there were so many different things going on young age, Kansas City. Oh, absolutely. So, so if I take you back to little Tiffany, um, little Tiffany was deeply insecure and like any insecure individual, you mask it in something. So, so, so let me let me paint it right. Late 80s, early 90s, I was a thumb sucker for a majority of my life. So, I had an overbite. I had a stutter and I had a lisp. Um, I also had a Jerry curl and I was not a Jerry curl. Come on. I couldn't quite get it right. So, you take all of those pieces and these same um features that I have

[6:20]  on my face were on like a eight or nine year old. So, there was teasing that came with that. And so because I was short and happy identities that I had with the jury curl, the lifts, the stutter, the only mechanism of survival for me was fighting. And I had two ways to fight both verbally and physically.

[6:37]  Now don't let the little jacket fool you. Huh? Run up. No, just kidding. Let me focus. That was old Tiffany. Old Tiffany. Old Tiff. That's old Tiffany. That's old Tiffany. So for her the the survival came from like I literally have had the same above average personality but it was compensating because if I didn't want to get teased I needed to make them laugh or make them afraid. And so my gift of gab came in handy for survival. But then I met a teacher and this is why educators are so deeply important. I agree. Number one, it was a black female educator and Miss O'Neal said, "Don't let your mouth write a check that your tail can't cash." That ain't the language that she used, but you can see where she was going with

[7:23]  that. And she was like, "You could use that mouth for good." She put me on the debate team. And at that point, she um she set us up and I had to be the defense attorney for the Menendez brothers. I'm aging myself because they were on trial and that was on TV all the time. I don't know why she had us in the fifth grade doing this, but she was showing me that I could even convince people that the most wrong of wrong persons, there was an inch where they could have been right. And she said, "So instead of using that to tear people down and to fight or to get yourself into situations, what if you used it for good?" And so then she showed me that while I had a gift to fight, there was another type of fight that I could get into, and that was advocacy for folks.

[8:06]  So then I turned into like the bully slayer. But then you know a future teacher had to say listen I understand that you want to help people that can't defend themselves but you need to heal that which draws you to that role because you're doing that out of place out of a place um of your brokenness. What I had people pouring into that little Tiffany that allowed me to become who I am today. Right? to turn those natural gifts from a place of defense and survival to liberation for others.

[8:39]  And so for me, I've literally been a fighter all my life. And that's what I do in this role just in a different way. So yeah, you know, I love that you you tapped in and you gave a shout out to the educators because there are some good educators out there that like they said, they seen a struggle. they may have seen where you were broken somewhere and they tried to help you fix that and think differently because when you grow up one way that's all you know you know and then when someone else tells you something different you're like oh wait that's possible you know here you're on the debate team you you having these doing these things you're like I didn't even know that was a thing for me now that you say that I remember very early on uh a male teacher I was probably like sixth grade you know I was a really good kid through elementary but I don't know what happens when you get to high school you just step up a little bit and and all of a sudden you want to people, right? At least that was me. I

[9:26]  just wanted to fight people. Um, you know, defend myself. And probably very similar reasons for you, right? There was just there was trauma that uh was going on in life and this is just how I dealt with it. I I didn't know how to go zero to 20. I went zero to 100. That's it, you know? And um I remember him putting me into things like performing arts, right, the theater, acting, and and I love that. And to this day to even know that I'm kind of in this space just you saying I'm like man how teachers make an impact whether it was just that one year whether it was that one class that will carry on for a lifetime. I remember a high school teacher telling me me and her got into it all the time.

[10:00]  But she would she would tell me um in high school that um you are who you surround yourself with, right? Those those five friends, give me your five friends, I'll show you your future. And sure enough, as soon as I left high school, I seen that. Not me personally, but I was able to see a friend um that spent five years in prison. Great, amazing person, number one wrestler in the state of college. However, he uh was with the wrong crowd and did five years in prison, you know, and lost five years of his life. So, when I hear when I seen that, I went back to that same teacher and I said, "Thank you for saying these things because maybe at that moment you didn't understand it, but then you seen it happen and thank God it didn't happen to you, but now you're able to also kind of help others." And what you've been doing since those moments is when someone helped you, it's like, how do I continue to pour somebody else's cup?

[10:46]  This is cool. It felt good. I want to do what she's doing at how whatever level it is, right? Whether it was an educator, now you're in the nonprofit role. And I want to still tap into to Tiffany because we're going to get to the leader. You're going to tell me a little bit about what you walked into here in just a bit. But you were also some adversity that you had to kind of face is that you bec you became a young mom, right? How did that shift your your hustle and and your heart? Absolutely.

[11:09]  So when you when you So I tell you told you a little bit about elementary and middle school and the teachers that poured into me, right? There were teachers of color that could see something in me, brought it, sewed that seed, and I started blossoming. Then my parents, you know, they got hipped to, all right, we've raised our kids in a certain neighborhood. We've reached a certain level of affluence, if you will.

[11:31]  Let's go ahead and move them to the suburbs in the stronger school district. So now I go to a majority environment where everybody that's taught me that I go to school with looks like me to the suburbs where I'm one of them. And that happened my um sophomore year of high school and I was 14 years old and that's when I got pregnant with my daughter.

[11:52]  Got pregnant at 14, had her at 15, but I was on bed rest when school started. So that means all my schoolwork came home and then this little black girl with this little baby shows up in this predominantly white environment saying, "Hey, I'm here to learn." And it wasn't probably until end of sophomore year, maybe early junior year, that a teacher connected me with the parents as teachers organization. Think about that. You go it I basically was in isolation for a full year of schooling in my formative years while trying to raise a child.

[12:25]  Yeah. I had the village of support but in my area my high school I did not have that. So that created a bit of loneliness right and um started to build up some of those maybe old practices so that I could preserve who I had in that moment. Um but luckily enough there were friends that I met in high school that are still my friends today um that know my daughter very well. Um and then she also had her dad and I had her dad's family. But for me, I there was a choice that I could make. I could revert to the ways that I knew would allow me to survive, or I could step in and lean in.

[13:04]  One, there were a couple things that I did not want to do. I didn't want to get my name in the system because I had this this uh stigma or stereotype that once you're in the system, they're always going to follow you. And I I did not get any support. And I don't say that in a braggadocious way. I say that in an uninformed and an unintelligent way because there was no one there to tell me that this is just a temporary bridge to take the weight off. This is not the end of who you are or who you will become. And so for me, uh I do this work today because I was that 15year-old mom working threearter time from high school to college to try to make ends meet. And it was challenging and it was hard. Um, but there was no adult in that

[13:51]  predominantly uh, white environment to see something in me to say, you know what, you don't, it doesn't have to be this hard for you. And if you get help, that's not a bad thing. And so, there were obstacles that some would say were self-inflicted, but it was only because I didn't know better. And I can only imagine if I would have remained in that same school system where the teachers looked like me, were familiar with my neighborhood, what my life would have been like um if I would have had that support. And so for me that that was probably the keystone in me becoming this advocate because nobody should have had to experience those things that I experienced as a young parent. When there is a variety of resources in the

[14:41]  community that I was in at the time. If the Heart and Hustle podcast has ever sparked any idea or made you think differently, do us a favor. Make sure to guys share this, post it on LinkedIn, or even text that nonprofit friend that you just have. Whatever works, this is what keeps the conversation going and allows us to just grow this community together.

[15:03]  Seriously, we appreciate you. You know what's even crazier is when I hear and and you say you were a fighter your whole life and God really made you fight young, right? Like but it's almost like life prepares you for moments when you don't really you ask yourself in some moments it's like why why God? But then you get to another moment like, man, if it wasn't for me being that tough person when I was a young person and really being poured into. You were being poured into, you know, as a young girl. If it wasn't for all these people, I'm not as strong enough of a person at 15 years old to be moved into a whole new environment, have a child, you know, and still survive. I think that there there's is true leadership in who you are, but also the strength in in who you are as an individual because not a lot

[15:51]  of people could overcome that. You talked about not having resources, which is why we created this platform so we can share resource and people understand that there's nothing wrong with resources. It truly changes somebody's life. I actually was talking to a lady um some days ago that I said I asked her the same question I asked you the first time I met you. Why is this so important to you? Why is this mission? And she says, I used to be a single mom, homeless. I had everything. I had the master's degrees and everything and this organization helped me years later after I got back on my feet and they helped me and my daughter, you know, go make sure she was getting educated. Why would I not go back and be that to somebody else? Right. Like there's resource out here that really changes people's lives and I think sometimes they don't tap into it because it it makes them feel less than. Absolutely.

[16:38]  Absolutely. Go ahead. You say something and our lived experiences become our resources for others, right? because all of those situations created a level of empathy and understanding that had I not gone through those situations, I would not have a heart for humanity like I do today. Right? So, so I think that's the other thing to remember. Everything that we go through is a part of the becoming and it is not for us to just keep to ourselves. It is for us to share with others that despite your circumstances there there can be a different outcome but if we don't create spaces like this to talk through that people can't get the hope people can't get poured into right because there are so many different modalities in which

[17:25]  people can get access to information and others it's all kind of stuff being poured into our people and so I I tip my hat and give kudos to you for creating this space so leaders can come in and talk about yeah there was a hustle but there was a heart behind that hustle. hustle too, right? And so, um, this platform is going to absolutely change people's, uh, trajectory and help them see the hope and be connected to experiences that that they otherwise would not be connected to. I appreciate it, Tiffany. Absolutely. And I 100% agree with what you're saying. And I also kind of want to talk about something that you mentioned to me um, to divert what we're still talking about here. But when when you said, "I didn't choose this role. The role chose me."

[18:07]  What does that really mean to you, especially now after jumping in? And we'll talk about what you jumped into in just a bit, but I want to just kind of start here before we dive in and take that turn. Yeah. So, it's it's important. This is why I tell people all the time, try to draw this diagram with you in the middle and all the things that make you important around it, right? Or all the things that you're connected to.

[18:31]  God forbid if all those things were taken away, what's left? And when people are asked that question, they began to realize that for years of their lives, their answer to that question was built by other people. And that was exactly my story. So when I say I didn't choose this, the role chose me because I was on the trajectory to work in tech and make that good Silicon Valley money. You hear me? Huh? Computer science, interning with one of the large parttime corporations as an undergrad. And you know, you start you start you start smelling yourself because you know, I'm I'm a black woman in tech and people I'm like a unicorn and that money was good with that internship. But then every I think every person that is currently

[19:18]  um flourishing in their purpose had that moment where they was like, "Yeah, this is good, but I know it's not where I'm supposed to be." And so that's how I end. So that's what I mean when I say because it doesn't I've I've learned a lesson. It matters not how much money you make if you're not if you're not um living in your purpose and aligning your purpose with your professional your uh with your profession. And so for me uh it was a part of my divine assignment to be that advocate and fighter. And I knew it but I didn't want to do it because it wasn't sexy. It wasn't cute.

[19:56]  It wasn't what came with the accolades and the affirmations and the accomplishments, right? Being a black woman in tech, absolutely everyone wants to celebrate and people could relate to that and understand it. But when I pivoted and went into higher education because I was like, I want black and brown girls to have access to education and not have the obstacles that I had. I wanted young people that came from single parent homes. I wanted first generation college students to not go through the trash that I went through in undergrad. Right? And so this work literally chose me because none of the roles that I have had since I switched from tech to education and nonprofit none I've applied for none of those roles. Folks have literally come and said I believe that this role would be good for you because I was showing up in

[20:44]  my authentic self. I was showing up in my gift and in my purpose and so opportunities met me versus me going to look for them. So, I love that you talk about authentic. Anytime I tell people and other leaders, they always ask me, "What do you need from me? Show up as yourself. I I don't I don't need the suit and tie." You know, don't put on the show because that's not what I'm here for. Um, and that's not what I want to I one of the one of the leaders just like yourself. And he happened to be a black man, which was so exciting when I seen him across the table. We just don't have too many men of color in this space. But what he was dressed down in a tracksuit. I said, "Hey, man. I see that you just, you know, dressed down. He's like, "Oh, I can get a suit and tie." He says, "But I realize that young kids, people that I'm making impact to, they'll approach me more if I'm just

[21:32]  dressed like this myself versus me having to put on a suit and tie when in reality I don't dress like that, right? So, why would I sit here and and be something and then not get and return what I'm what I'm looking for? I can be myself, what you just mentioned, authentic, and the return that you get is crazy." Because in reality, people do business with people. People love to know that, oh no, this person is trustworthy, not just at work because they put on the show, but that's who they are all the time. Like, you get to see them out and about. So, I love you said authentic. And it's it is one of those major things that a lot of our our youth should should know when you're on social media and you're looking at all your your favorite celebrities. Like, you know, at the end of the day, you got to be yourself. Don't be them. It's who you are. And as you mentioned, follow that purpose. We're creative in so many ways. You're so creative and that's what kind of led you into the space. and you

[22:18]  take every single background, but um let's talk about it. You walk into this nonprofit, right? The first 30 days weren't smooth. The heating failed. I can only imagine, you know, that was crazy. You got doubts from the board and in reality, you come from something that you left that was comfortable. You super uncomfortable at this point. How how do you lead when everything's on fire and people are doubting you? Yeah. Uh when everything's on fire, I just try to stay warm and not be consumed. Right.

[22:47]  So you you laid it out. I left a place of comfort and I come into the lion's den of discomfort starting at the point of interviewing. And so this is so when we were talking earlier about everything in your life prepares you for what you're about to experience. Remember I I was a fighter so I I know a bully. I can smell a bully before they even open their mouth and come around the corner.

[23:10]  Right? So going into this process I picked up on the bully energy. I was able to pick up on all sorts of energies because of that previous lived experience, right? And so in the in the Midwest definitely prepared me for nice nasty out in the east. And so I knew the energy before folks even open their mouth. So that's number one. And then number two, when I got into it, I knew that I was um um you know, when you're interviewing, it's like dating.

[23:40]  Everybody sends a representative. I'm just I'm my best self. But then it's, you know, once you get connected, you like, "Oh, you don't you don't brush your teeth every day. What is this?" So during the interview process, I saw the association one way. Day three on the job, I had that crisis of the heat failing for 30 days and 30 nights. Now, mind you, this is like a 21,000 square foot facility, huge facility that has childcare, gymnastics, aquatics. So it's people on people on people that I have to manage. That third day that happened and for 30 consecutive days and nights the heat was out. And they tell you a good leader never let lets a crisis go to waste. I needed that c I didn't look at it as a crisis. I looked at it as a

[24:28]  gift because had it not been for that I would not have been able to see all of the deficiencies in some folks and the strengths in others. You can tell a person, you can tell the leadership of a true person not by how they respond when things are well, but how they respond when the when the stuff hits the fan, right? And that's exactly what I was gifted with. And so, how I survived that, I changed my mindset first. This is not a crisis. This is a gift. And what am I what what's being revealed to me in this time? And then obviously I'mma lean on the word because I went through a fast to come to say yes to this place. And then I had to reminded the weapons were formed but they'll never prosper. So I already knew in the end I would win. So if you begin at the

[25:17]  beginning of a crisis with a victor mindset versus victim, you cooking with gas at that point. With gas now. And so then you know build and building your support too, right? So while I'm addressing the crisis during the day, I had to have that village of support on the back end. So I had my thought partners and that's the the other thing, right? Yeah, I'm an answer, but not for everything. So who do I have around me to help understand facilities?

[25:44]  Well, the relationship that I have with the facilities director at my previous institution, I could call and say, "This is what's happening. What do I need to be thinking about?" So I I'm still deeply connected with my last three employers. One flies me out to speak to their students back in the Midwest. The other, the president of that institution is a mentor of mine. And I'm actually being recognized for the other institution that I left to come here tonight um at an event. So all of those relationships, I maintain those so that I could be uh successful in this role now. That's what uh it looked like when you don't burn a bridge. That's right.

[26:20]  Right. Because you never know when you got to go across that bridge again or when they got to cross that bridge to come to you. Right. Vice versa. That's right. Um, I I like that. I like you dropping some gems right here. For real. For real. I uh before we kind of pivot on to something, I I talk a lot about standing into your assignment. Was that true? What does that really mean to you as a woman of faith and a leader?

[26:42]  Yeah. Standing in man. Okay. So, we're going to have a good conversation. Yeah, we are. We are. is pulling some things out of me that I literally standing in your assignment. I had to learn that it's not always going to make the front page of the paper. And while while you're being successful and you're hitting on your objectives and stuff, there are going to be there are going to be times where there will be no applause, there will be no recognition. And so that says to me every day I have to die to that desire.

[27:20]  Now, keep in mind, we've been raised in um a generation where everybody gets an award, everybody gets some recognition, right? I mean, for me, I grew up there was first, second, third, and then out of that, you're a loser. Uh but now we shifted where everybody gets recognition. So I had to die to that first to understand that regardless of if there's applause or not, I have an assignment that I have to stand in. That also becomes challenging when you come into an environment where feedback maybe hasn't been the culture. So for me, I'm allergic to mediocrity. I break out in hives, short shortness of breath because I know the supervisors and leaders that

[28:08]  I've worked for would never let me skate in an environment, especially if the work that we're doing is tied to a family's ability to eat and survive in the community. And that's how seriously I take this work and the assignment. So if you think you fa to come here and steal a check while we got people to serve, I'm going to give you the feedback that perhaps you're working outside of the bandwidth that your skills are designed for. Right? So that's a that's that's a good clean nice way to say you're trash.

[28:42]  You got to go. Right? You're you're prohibiting families from getting access to resources and support to change the tra trajectory of their family's outcome to break the chains of generational wealth. You're in the way of that. And so for me, I have to know that that's a heavy and hard conversation that you have to have, but you got to do it in a way that preserves the professional dignity and shows folks that you may not be operating at your best here, but here's where I think that you can thrive. And if that means you have to transition from us, that's okay. because I'm not gonna rob you of the opportunity of being your best self by allowing you to underperform in a role that doesn't align with the skills that you have.

[29:28]  And the reason why I'm able to do that is because low key that's kind of what God said to me. Like you think computer science is your thing just because you're good at math and you're going to make a lot of money, but that assignment is too small for the assignment that I assigned to you. You're literally operating in a field that's outside of the skill set I equipped you with.

[29:54]  What? And so for me, people ask me all the time about this work. This work is like ministry for me, right? It's it's really for me to help folks unlock the best version of themselves, even if that means having a hard conversation. I love that, Tiffany, because um I don't know if I mentioned to you, but I say this often that my wife likes to tell me that you should be a pastor. Not only my wife, my best friend, right? Every time they see me praying or they just see me going to talking cuz I love to talk and you find me anywhere talking to anyone like this. And that's like, man, you should be a preacher. And I was like, but I do. I preach every single day. you know, the work that you mentioned, the work that you do, that you can talk to anybody and everybody, no matter that they're someone of God or not, and you still get to be authentic yourself and still pour God and still pour positivity

[30:42]  and like you mentioned, one, we we meet them where they're at. I think that's huge, you know, but let them know, hey, I was I was that person before. I I I struggled, you know, I I needed help. I you know, I wasn't always a leader. Mhm. There's people to this day that still pour into me. You know, just about a year ago, um I think I may have told you this already offline was that I had uh my mentor tell me, Eph, I've seen you build brands and because I was still in that corporate world, like I was still playing corporate entrepreneurship. And he was like, um I I've seen you build brands for for yourself, for other people. And I realized that there's things out there that people um teach that they need most. They're the best at teaching it, but they need that the most. He says, "You always teach someone to know your worth. When do you start to realize your own? When do you start to

[31:30]  value your time, your talent, you know, your purpose?" And sitting here and thinking about all this leads me to sit across the table with with people like yourself. I didn't have this on my bingo card of things that I was going to be doing. I've always done podcasting, but to know that just a year ago, I also took over a nonprofit as a leader, you know, after stepping away for so many years. Now you telling me I'm sitting across the table from CEOs of nonprofits all the time that are running million-dollar organizations. I'm right now struggling with my organization. But selfishly, no. The reason you're going to be in front of these people is so you can see people look like you, you know, that have experienced what you've experienced, you know? So if you ever have any doubt and believe me when I get off these calls, Tiffany, it's always motivating the energy of like damn like look at these people out here do like

[32:18]  I'm so happy that I'm in this space because I have not met somebody in the nonprofit world that says I hate what I do. I want to go to for-profit. Yeah. I don't see that. But I tell you what, I have seen people in the for-profit space saying I want to go into the nonprofit. That's right. You know, so I love what you do and what you what you're saying like people got to really take this in because it it when you're trying to chase something that is not you that your mom told you to do, your dad told you to do, you know, someone told you you're good at and you and then you're still asking yourself like what am I doing? I'm not happy. It's because you're not really living your purpose.

[32:53]  That's right. That's right. You know, so I I love what you you talked about it. And before we talk about a little bit about diversity and equity and the truth of nonprofit leadership, I ask you this last question before we pivot. Both of us had a to grow up quick. You would agree, right? You think that's a superpower in surviving adversity? Like I almost feel that people that struggle and go through these things almost have these superpowers especially when leading with empathy. Absolutely.

[33:19]  Absolutely. You combine that with a little bit of melanin in the DNA. Absolutely. Superhero status. unlocked and and and and I'm glad you asked that question, Ephra, because I had a conversation with my daughter the other day and as I mentioned, she's 29 years old and and she's getting ready to get married in August. And one of the things that we talked about is we always talk about how her upbringing cuz it has it was it was she and I for so long, just the two of us. She has her dad, but in the house it was just the two of us.

[33:47]  And so she would say like, "My I'd absolutely respect everything that you and my dad did, but like for me in my generation, why does every thing have to come from the mud?" Right? And I was like, "Yeah, I get it." And and we've provided like we've provided a way for generations to not have to experience everything, but everybody has to experience something. I believe you have to have a little bit of skin in the game because at the same time she asked me that question, I will ask her, how do you think I got to where I was? There were things that I had to figure out on my own. I had to learn how to talk to financial aid. My parents didn't go to college. My sister, she graduated from college but was in the military. So, I

[34:34]  had to learn how to talk to people. So, these skills that I have and the things that you admire about me didn't come just by birth. It came by learning systems, learning people, and those valley moments. And so, yeah, for me, I absolutely believe growing up quick. I had my first apartment at 19. I moved out of out of my mom's home. And so, I had to learn how to pay bills. I had to learn how to uh negotiate with a landlord or a bill collector until the financial aid check hit so that I could keep lights on and food on the table and things like that.

[35:12]  And so for me, growing up quickly, yeah, it definitely is a superpower. And I'm not suggesting that everybody needs to go through something. I am saying, however, that every situation that you're presented with that makes you uncomfortable, perhaps that's your superpower moment, right? Perhaps that's the situation that's going to unlock that superpower level of thinking or strategizing or connecting or resolving issues. Like what good is becoming an answer if problems didn't teach you how to be an answer? Yeah. And so when you break it down like that, I try to help young people realize all the time, yes, I want you to feel the feelings because feelings are to be felt, but you can't stay there. What are you going to do about it? Um, you need to feed yourself

[36:02]  versus eating what you're being fed because the system is going to feed you what it wants for you to produce what it wants you to produce. Yeah. But if you feed yourself solutions and results, it's going to be the result that most that is most beneficial to yourself. And so when you start switching your mindset, uh, things just start shifting and changing. So I absolutely believe uh growing up fast is a superpower that I have. Listen, mindset is everything. And I'll take you to something that's really basic. Something happens in your life and we automatically go to the negative that's happening, right? But in reality, what is the lesson to be learned? And that's one of the biggest things that I've learned very young was when something happens and you're asking yourself the why. Um listen, that's part of life. What is the lesson there that you can take that you're going to then

[36:51]  input into your life, right? And I'm also a big believer that when things are handed to you, people don't appreciate it as much. But when you have to fight for it, when you have to get uncomfortable for it, the things that you learn because you got uncomfortable and the now you appreciate it more. Now it goes to show how strong you are, you know. So when people are, if you're listening, if you are in those uncomfortable places and you feel like maybe the leap you're taking today is very uncomfortable, nothing good ever came easy. And Tiffany, I'm pretty sure you could vouch for that. I could definitely say that and we're still nowhere near probably where God is is going to bless us with. But we know that it comes with getting uncomfortable every single time. You've got uncomfortable so many times in your life. Sometimes by choice or sometimes just life be lifing, you know, but you you always remember what was it that I

[37:38]  took out of those moments. You talk about from a young kid, right? You every step of your way you remember those moments that were hard for you, but you remember the lesson. And that's the important part part especially in our our generation today is yeah very quite different than how we grew up but I still think there's a sense of the mindset every time something happens you don't got to think the most negative think okay great if I do this a little bit more maybe I get better at it you know or what was the lesson at that moment that's right and and using that same mindset on yourself too right I think sometimes when we get something wrong because I've gotten things wrong a lot and continue to not be perfect. Um, but I also, you know, you you hear folks say you got to give yourself some grace.

[38:22]  You absolutely do because I am a student of life. I will never solve all life's issues or problem. Life will continue to present me with challenges. And so, I am committed to learning from her. And so, in that learning, I've got to be flexible. I've got to understand and and and you got to do it in a way where you're not like, well, I'm waiting on the other shoe to drop or when is the stuff going to hit the fan. No, I'm prepared. If it hits the fan, I got an umbrella, right? So, um I think that we got to apply that to not just the situations externally, but to our internal selves as well. So, I'm have I'm gonna ask you a question because maybe people want to know this and they they probably want to, you know, ask you this, but they're not here, right? One of the biggest things when I was

[39:08]  struggling mentally because life happens sometimes like you mentioned and we got to be our own like pour into our own cups because we don't got people pouring into us. We pour into everybody else. That's right. People going to call you all their problem and never ask you how you doing. Okay. So, I'm pretty sure you experienced that. So, for me, when I made the the jump and I put my family on my back and I said, you know, I'm I'm I'm stepping out on faith. I had to tell myself this is part of the process. It's going to get better. um you're going to see you know I almost felt like I was in this dark tunnel seeing the light at the end I just like how far is it really going right so telling myself that it it's going to happen you know have faith be patient these are things I'm telling myself the music that I was listening to was very different like I'm listen I'm listening to music that was just speaking to me in a positive way u and

[39:55]  that's what kind of got me through the times that were tough when I was feeling the pressure on my shoulders physically feeling it what are you doing when things get tough what is your go-to sleep. No. Um I like real talk, I do believe rest is a legit act of resistance. And I know that there's some of us that are in that climate right now because we did everything that we were supposed to do to not be where we are in 2025. So there are 92% of us that are just Oh my god. Come on. I think we lost Tiffany.

[40:36]  You're back. You're back. That's that good nonprofit internet. But 92% of us are resting. I'm dead. That's a good internet. You hear me? Oh, today. Um but but rest is a form of resistance. And I I believe in that 100%. But I will say um similar to you, Ephan, I what you put in your eargate is what's going to echo in your soul. So there are moments like yesterday was one of those moments. It's heavy and it's hard and while I want to break, I cannot. But I need to do something to fill my cup. And so it's like a it's an anthem. It says, "Sound the alarm. Put on your lace up your boots. Put on your backpack. It's time to ride." I had that on repeat for the

[41:25]  rest of the day. And that just shifted my mindset because it reminded me, right? So, for me, it's rest. A good little playlist. But real talk, the rest is huge for me. And I sleep with brown noise because you got to give your brain a break. That if you're anything like me, your brain is constantly firing off ideas and thoughts, particularly if you're in a storm because if you're naturally a fixer, you're trying to get to shelter as soon as possible. And so, but you do yourself a disservice if you never turn the system off. And sometimes you legit have to turn your mind off so that your body can fully reset. No one has ever made I don't believe anyone has ever made a decision that was 100% beneficial in the outcome when their

[42:14]  mind was foggy when they when their mind was distracted. And so for me that's that's a part of it. Like people are like well what do you don't do? You go on vacation. I literally turn everything off and I rest. So, yeah. Yeah. I like how you said turn your brain off. Sometimes I'm laying there in bed telling my brain to turn off. Like, can you please shut I am trying to go to sleep, right? It do. You just as creatives, as problem, you know, solvers, you just always have this idea.

[42:43]  Whoever may be my neighbor um just recently, you know, got let go. And I'm over here like, "Well, you said you always want to be an entrepreneur, so let's get it." You know, and and he's like, "You're weird. Like, why are you so excited?" I'm like, cuz God blessed you with this. Like, do you not see it, right? Like, I'm I'm that person now. I feel like I got to help him, you know, even though if he wants to help or not, you know, in hopes that he does, but um we're about to ruffle some feathers. You ready for this question? Next question.

[43:06]  Oh my goodness. Feathers are ready to be ruffled. I think that people love the idea of diversity until it actually um happens to do with who's at at power, right? Who holds the power? How do you navigate that dynamic without ever losing your voice? You're a black woman walking into this nonprofit. People looked at you like I'm sideey, right?

[43:28]  For sure. How do you do that? So, I think the first thing is we got to call a thing a thing. The current climate that is against diversity, equity, and inclusion is actually against blackness. It is antilack. It is anti-Latino. it is anti-LGBTQ. Um, so we we we we we've got to call it what it is, but I'm go I'm going to say at the foundation when the hues of leadership and beneficiaries change, that is that is what we're talking about. And that's what we've been talking about for years, even before now, right? So, how do I continue to advance the mission of an organization that literally has in its mission eliminate racism and empower women? two things that are deeply being

[44:16]  targeted right now. And I I do it through through a lens that allows me to still address the needs, but not um so here's the thing. You can argue with me all day, but you can't argue with the data, right? And so for me, I tell people all the time, as much as I love my above average personality, a room full of Tiffany's is only going to go so far. So diversity in thought, diversity in lived experience, gender expression, gender identity, all of those things. You got to make it happen. And so for me is I just keep moving because I I know that the work that I'm doing is is is aligned with my assignment while I'm here on this earth.

[44:59]  But I also help people understand the facts. We're living in a place where there's no factchecking. So when we talk about diversity, equity, and inclusion, I start with, well, our foremothers and forefathers kind of wrote it into law. And so I show them all the laws, whether it's um affirmative action, whether it's SNAP benefits. And I say the historical benefactors have been all the people that don't look like me, right? We know that white women have been the largest beneficiaries of affirmative action. We know that white veterans were the largest beneficiaries of the GI bills.

[45:35]  And that's not a Tiffany thing. That is data and fact of this history. And so because of that, I still uh advance that agenda simply because everything that we're experiencing right now is temporary. Nothing new under the sun. Nothing's new under the sun. So we've been here before. And so for me, I'm not focusing on the resistors because I believe that that is just a loud minority. There is a silent majority that needs to be reconnected with the fact that there are deep benefits when the room isn't monolithic, right, or monochromatic. So with that, uh, that just gives me the inspiration and insight to kind of move it forward. I

[46:22]  recognize there are resistors. Absolutely. there always will be. Uh, but I focus on the folks that want to continue to advance the work and try to align with them and keep it moving. And I know you're all about truth, being authentic, having those conversations that people don't want to have conversations about. And I believe you told me that women in this space are less funded. Oh, absolutely. What is that truth about being a woman? Tell me other truths that maybe people are not talking about of being a woman uh of color and the nonprofit leadership that doesn't truly get said enough that people just kind of sweep under the rug.

[46:58]  Absolutely. Because we have to understand that as number one, there's stigma around women leadership. There's stigma around people of color in leadership. When you combine the two, that list just grows. And so there was a recent report that spoke to the fact that nonprofit organizations led by women of color are un are funded um less than nonprofits led by uh white women.

[47:28]  And so we have to create conversation around that in the places of philanthropy to say that I'm not saying that this is you doing this but this is a reality of nonprofits led by women of color. We just have to be aware of that so that these foundations and uh philanthropic organizations can ensure that their practices on the back end is assessing what can we do to combat that.

[47:53]  Maybe we were more intentional about connecting with nonprofits led by women of color to ensure that a they're applying for our grants. And when we look at the folks that we grant the resources to, are we doing it in a way that's equitable and representative of leadership throughout the nonprofit sector? So, I love that. Do you have a hard stop by the 30 mark? Because I feel like this is about to go longer than what we expected, but it's having a good conversation. you know, I feel like there's so much here that we we really provided to people. Um, I want to talk about your background a little bit in in just computer science because we're also in a space you talk about being a tech, right? Uh, Vilicon, Vilicon, Sally or whatever valley, Silicon Valley saying completely wrong. People are definitely going to butch me on this one. Um, but now we're in a space of AI probably

[48:41]  where all techs are are talking about and everyone now is an AI genius, right? There's so many products. What is your thought about AI in and balancing um innovation but also humanity and how we incorporate that into the nonprofit space or maybe give us some tips on how you utilizing your nonprofit? For sure. For sure. So, so A and I ai and I go back like four flats on a Cadillac, right? So, I have a great respect for the tool that it is. Um but here's my message to humanity. Don't let AI make you lazy. Like some of y'all are walking around here and you can't even complete sentences because you so used to chat GPT or Gemini writing your email, right?

[49:24]  And then the other thing is be aware that people have filters on their devices that lets them know if this was AI generated because here's the thing, right? There's one thing to draft a message and say polish it and it's another thing to um prompt it to write it for you. So here's the thing. If you haven't primed the machine to become familiar with who you are, it is going to sound like a machine. So, so if you putting garbage in, you're going to get garbage out. That was like lesson one in C++ 101, right? So, I we we have to be more thoughtful and that and not allow it to rob us of the natural skills and gifts that we have because the tools that we have need to be primed. And if the machine does it all for us, we're

[50:13]  going to experience that atrophy. Atrophy in thinking, atrophy in conversation. And so while it is a tool that is good, you got to understand the tool. And you have to understand how machines work. And then you have to prime the machine and customize it so that it's a partner, not something that paralyzes you, right? And so, so how am I using it here? Number one, I didn't had that same conversation with my staff. send me an email that's that's AI generated, you won't get a response.

[50:42]  You'll get a phone call. Let's talk about this. Um, but if I um but when we're writing grants, for example, or when we're thinking about troubleshooting problems or when we need to we get a big document, okay, can you summarize this and give me the points that I should know as a CEO leading a nonprofit that's focused on eliminating racism and empowering women? the specificity of that is going to allow that tool to produce the nuggets that that support me in digesting it a little differently. So, I think there pros and cons um to it, but definitely we can leverage it to do some of the deep research for us. Um but it should never become our ma mouthpiece. It should be our partner um not the driver. Yeah, I think there's so much opportunity there.

[51:29]  um my my partner in this podcast, Keenan, he he developed an AI tool that really kind of helps at the communication level and understanding what people's needs were, right? Whether there was a nonprofit or the healthcare space, and it's how do we continue to keep our community engaged and what is the number one way of keeping our community engaged and and we've found that it to be the text message, right?

[51:51]  So, and it's it is AI powered, but to realize how AI even myself, I developed something on my end. Listen, I'm not I'm not no tech person. I'm not you, okay? But when I did this, I could be a tech person now. Now, I always tell myself, people used to ask me like, "Man, why don't you get an IT?" Because I used to always want to fix something. I'm like, it's just not me. Like, I'm just a problem solver, but I don't care too much about it, you know? But on the back end, I was realizing that with these podcast clips, I had to find something that was very easy for me to kind of plug and play. So, I'm at a space now where I can drop a video in Google Drive, and on the back end, it it strips the audio, creates a transcript, goes back into my chat GPT, as you mentioned, but I created a GPT. Some people don't even know they can do that. Uh, and then by the end of it, it g me the clips and the hashtags and it sound just like me because I done like you mentioned what I fed it. I I took time to give a data. It got to know me. It got to, you know, all

[52:39]  these different things. Even grab videos so it knows that I have high energy. So there's so much opportunity on what really AI can do. And I I'm almost feel like nonprofits are kind of sleep on it. Like I speak to some leaders and they think the best AI is, oh my god, I got a claude and I got a chat GBT. I'm like, if you only knew that is like very lowlevel AI when there's things that really help. Um, is there anything like if you could have a a 247 AI that could help you on your day-to-day, whether that's community engagement, donors, volunteers, what does that actually look like for you?

[53:12]  So, I'll I'll take it through three pillars, I think. Um, from a programmatic operations standpoint, data analysis is huge. So creating the tools to help us capture data and capture data from our constituents in a way that's beneficial to them. So parents on the go um folks that you are using public transportation um that that capturing that data of who we serving who we are serving um their point of entry being able to analyze that data and then you know converting and turning that into the various reports for grants. So that's the programmatic piece. Um, I'll say from a financial piece, from a donor standpoint, doing the donor analysis and the donor research, looking um, and and I'm pretty sure this tool is is out

[54:01]  there. Uh, but this is why I'm hiring a new development officer so that we can get someone in here that can use those tools to do not only the donor analysis, but do an analysis of the corporations that are giving to organizations that are similar to ours. those tools exist, but then being able to predict or hypothesize the likelihood of giving to an organization specific as ours in finding us the folks and then creating here's the blueprint of everything you need to do over the next 120 days to secure the deal, right? Because it's one thing to get the data. The question is, well, what do I do with it? When you think about the nonprofit space, people are drawn to us because they want to help people or they love people. They want to solve that problem. But when you think on the back end, what's required

[54:49]  to be able to solve that problem, there aren't data analysts that are running to come serve nonprofits, right? And so, you've got to have those tools to get to the folks that were drawn to you for the mission so that they're not like, "Oh, you want me to do data? I can't do that. I just want to do programs." Actually, you can, right? So, I love that. No. Yeah. for sure. Grant writing has been one of the AI things that I've seen almost actually, believe it or not, people are still not using it. Um, I heard that and even I was kind of surprised to be quite frank even though I use AI for everything. Never thought about grants. But as I'm telling it to leaders that are making, you see the nonprofit I'm in, we're not making millions of millions of dollars, right?

[55:26]  We're probably doing right now 20 30,000 a year. So there's no need for me to think about well there is a need for me to think about grants but big corporations that are still looking for grant writers don't realize they can use a chatbt to help them write grants you know so we're talking about nonprofits um falling behind I think it's happening right and and I actually ask you do you think that there's anything um any gaps between what nonprofits say they're doing and what they're actually doing I think there's also some gaps there have you seen anything working with some other organizations I will say some some of the gaps depending on the nonprofit exist because they don't have the tools to capture the data like they they see the qualitative results but you know any type of funer is like I don't care how you making people feel what's

[56:13]  the number of impact and and so that doesn't make it right because I do think we need to modify and change that but um the the way we tell our stories and I would just encourage nonprofit leaders or leaders of any comm community- based organization we have to slow it down because the needs will always be there because the system is going to be the system that created these needs in the first place. So, we just have to slow the process down so that we can tell the full story. Because if we just keep going, going, going, and we're not capturing the clean data. We're not telling the full story of not only who we're serving, but the successes of those folks, we're just going to find ourselves in this hamster wheel rinsing and repeating. And so, um, yeah, slowing down to tell that story, to get the

[57:00]  data, you'll see that number one, you probably have other opportunities to generate additional revenue to go after different sorts of grants. Um, so I think that that's something you could do, too. We're going to start wrapping this up. We're kind of at this hour mark. If someone's listening right now, Tiffany, and thinking, damn, may maybe I've been saying no to that thing I'm actually meant for. What What do you want them to know? What do you want them to um just take out of this conversation to make their decisions? Yeah. So, the longer you resist a no, the the the more you're going to find yourself subject to the stressful conditions that you're in, right? The more you resist what you're actually supposed to be doing, the more you're going to find frustration with

[57:47]  yourself, frustration with where you are, and you literally become the obstacle um to your full destiny, right? So, you literally become the obstacle to you being able to operate fully in your gift and experience. And so, why do that to yourself? Like, what? Um and take it from us, for those folks who did say no, who did resist. I thought life was good, but I gotta tell you, I wouldn't go back and and sit in that seat again. Yeah.

[58:15]  Because I've learned so much about myself. It's opened up so many opportunities. Yes. For me, but opportunities for others as well. So, yeah. I love that. And before we get into that blind question, which I'm pretty sure you're really excited about, for those that are watching, how can they support people um support the YW.CA um beyond just writing a check?

[58:36]  Absolutely. I would say with any of the YWs across the country, we always are looking for volunteers. We have youth-based groups that we're looking for folks that are willing to share their stories um not just of the successes but just of life in general. So, while you can donate your your resources, you can also volunteer your time. And even if you don't have a YW in your area, if you believe in the mission, you can advocate for the causes um in your community that support uh the elevation of women, girls, and people of color.

[59:11]  Love it. So, the the blind question, you ready for this? I am. You walk into a room 10 years from now, your work is completely done. You're retired. We're gonna speak into existence. By the way, Tiffany, you retired now. You know, you living good right now. Silicone Valley, where you wanted to be at. The room's full of people. You've impacted, but you don't say a word. What do you hope they say about you when you're not there to hear it?

[59:37]  What do I hope that they say about me? I I really hope that there was joy that was either restored or introduced to them. Um, none of this work that I do m I mean it it is something that can be birthed when you meet joy. And I hope that every interaction that I have with folks leads that person closer to that introduction or reintroduction or restoration of joy. That's what I hope.

[1:00:23]  I love that. I love that. What's your time? What's your blind question to the next leader that we have here? To the next leader, because sometimes it's hard for people to open up. What has this work cost you? Oh, that's deep. Yeah. So, Oh, that's deep. Okay. All right. I appreciate Well, Tiffany has definitely been a pleasure. For you guys that are still watching, make sure you guys share like when we talk about how can you help an organization without doing much is by sharing these conversations because these conversations what changes people's lives. We talked about mindset.

[1:00:55]  We talked about some resources that you can find at the uh YW.CA. We talked about real life experiences, things that we've encountered and letting people know that you're not alone in this world. That we all have these chapters in our lives that we don't like to go back and look at, but then we have the best chapters in our lives that we're like, man, I'm happy that I went through them. So, if you guys are still watching, make sure that you guys do share, like, uh, and if you guys want to find Tiffany, Tiffany, where can they find you? Where can they find the organization? Let them know. Absolutely.

[1:01:21]  You can find the YW at Ywca wpcw.org. And you can find me on Facebook or the YW on Instagram and LinkedIn. So, check us out and hope to connect with you all soon. Thanks for this opportunity. Thank you, Tiffany. It's been a pleasure. This been the hard hustle podcast. My name is Ephrain. We'll catch you guys on the next one.

[1:01:40]  Plus,

th
guest
Tiffany Hamilton — CEO, YWCA White Plains and Central Westchester
Nonprofit

Tiffany Hamilton is the CEO of YWCA White Plains and Central Westchester, leading the organization through today's evolving DEI landscape. Her path to nonprofit leadership began with teen motherhood and a career in technology before she answered a call into advocacy work. In this episode of Hart and Hustle, she discusses turning adversity into purpose, leading with faith and authenticity, and building resilience into how she leads through crisis.

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