In this episode, host Lorie Jones welcomes Tracey Windsor, CEO of Windsor Edge and former New York City dancer, for a conversation that’s equal parts energizing and insightful. Tracey shares her bold leap from the arts into nonprofit leadership and eventually the high-stakes world of private equity, showing that success favors those who embrace change and pursue what excites them.
Tracey discusses making tough career pivots, overcoming doubt, and staying true to your passions while navigating male-dominated or established professional spaces, with practical advice on building strong networks, crafting your own opportunities. You will hear how she balances creativity with strategic financial thinking, and why she believes mastering money puts real power in women’s hands.
This episode is for any woman looking to build a purposeful career on her own terms—and have some fun while doing it. Tune in for honest insights, fresh inspiration, and the encouragement to bet on yourself.
Show Highlights:
- How embracing finance can empower multiple passions. [05:15]
- Does being in finance mean sacrificing your creative outlets? [10:35]
- Why fearless career pivots are powerful growth drivers. [12:43]
- How to navigate resistance to nonlinear paths in traditional sectors. [16:03]
- The power of future regret as a catalyst for pivotal action. [17:50]
- Should young women integrate the remote work model early? [20:55]
- Common fears around achievement, visibility, and self-worth. [26:28]
- Subtle worries and overt biases women in finance encounter. [28:20]
- The value of immersing yourself in vibrant communities. [32:33]
- Key “people lens” and coaching strategies for professional women. [37:14]
Connect with Tracey Windsor on LinkedIn at https://www.linkedin.com/in/traceyjwindsor/
If you enjoyed this episode, please go to Apple Podcasts and leave a review!
For more information about Lorie Jones, go to https://fearlessfinancialadvisors.com/fearless-females.
00:01.91
Lorie Jones
Good morning, fearless females. So today we’ve got Tracy Windsor with us. She’s the CEO of Windsor Edge. And I’m super excited talk with Tracy.
00:12.78
Lorie Jones
We actually had a podcast. She does a podcast. And so I was on her podcast not too long ago. So I really um enjoy talking with her and I appreciate you being willing to come and share your story.
00:26.92
Tracey Windsor
Laurie, thank you so much for having me. Yes, starting a podcast and being the one asking the questions feels a little bit more comfortable and i have been wanting to ah see what it’s like on the other side. And so I think this will give me a ah great experience ah to see what it’s like to being asked the questions.
00:46.11
Lorie Jones
I know. i always kind of hide behind my microphone here, and it and it’s a little different to be on the other side of it. But I’m super excited that we get to hear your story. So i always start out with the question, I’m a reader. I love reading. I love books. Tell me about your favorite.
01:04.83
Tracey Windsor
My favorite book, which has changed drastically um throughout my life, especially the fast past few years, I’ve been reading way too many self-help and business books. And I’m like, oh gosh, I really need to read more. But um I did read a fantastic book. It’s called The Weight of Ink.
01:23.95
Tracey Windsor
It’s a novel by Rachel Kadish. And what love about this book is it takes place in two different time periods and it’s showing the parallel of these two women’s lives, which of course is great for the Fearless Females podcast.
01:40.74
Tracey Windsor
um And it’s also timely in that it it talks through you know issues with women having to make sacrifices that men don’t have to necessarily make and about interfaith relationships, which I think now we need a a lot more connection with interfaith and intercultural um yeah with all of the geopolitical issues right now, we could definitely use more understanding.
02:11.29
Lorie Jones
Yeah, I think that’s neat. So it it goes through two completely separate women’s lives or do they overlap?
02:18.34
Tracey Windsor
It overlaps in the sense that it’s kind of a, it’s a little bit of a mystery unfolding that the first woman the 1600s and is transcribing this text um and is transcribing this text And the woman in the 2000s is trying to figure out who wrote this.
02:40.64
Lorie Jones
Oh, that’s cool. That sounds really fun. That’s a really neat book. I love that idea. And I do not read enough fiction. i i am always, i am, I too am reading like the self-help and be a better leader and grow into a more important person. And I feel like sometimes that you miss that idea of like just reading for the pure joy of reading. So thank you for that suggestion. I’ll put it on my list.
03:05.89
Tracey Windsor
Amazing.
03:07.27
Lorie Jones
So tell me a little bit about your journey, Tracy. How did you get started? um you know, like, what did you, what do you do? um And, and how did you get where you are today? Just talk to me a little bit about that.
03:20.44
Tracey Windsor
I love my journey and I love talking about it, honestly, because I’m really proud. It’s something I’m proud of that I take a lot of risks and I make a lot of changes and I don’t know where I’m going to be in the future.
03:36.70
Tracey Windsor
And i I like not knowing where I’ll necessarily be in the future. So I went to um university for dance and moved to New York City after to be a dancer and a choreographer and an artiste, and which I will forever be
03:52.45
Lorie Jones
Mm-hmm.
03:55.26
Tracey Windsor
um But I also let myself follow other types of interests. was passionate about changing the world, but more so passionate about why don’t I know anything about the world and how do i become someone who can even make a strategy or or think about how to create change.
04:14.84
Tracey Windsor
So I just wanted to become more educated and and to learn ultimately about the nonprofit world. I ended up working in animal protection nonprofits for a few years.
04:26.70
Tracey Windsor
loved, um, loved working with data and strategy and high level and working with the leadership. And I found it a very empowering to, be working on high level, broad projects that were going to impact a lot of people, communities, uh, animals, um, both working specifically in, um in one nonprofit developing,
04:54.09
Tracey Windsor
ah
04:56.50
Tracey Windsor
developing fundraising plans ah for various campaigns, um including lobbying in different ah governments all around the world and working with corporations, like huge corporations to make changes for animals and ah just really amazing stuff to make to make a difference.
05:07.46
Lorie Jones
Mm-hmm.
05:18.12
Tracey Windsor
But I wanted two things, to stay in New York City and
05:26.36
Tracey Windsor
to continue growing and creating opportunities. So those two things led me to really want to go towards finance.
05:37.39
Lorie Jones
Mm-hmm.
05:37.60
Tracey Windsor
So I thought that if you learn finance, you can do anything because everybody needs that. And also i want to be able to afford New York City and nonprofit was not doing it. So that’s, those are the two paths that led me there. love to ah The more I learned about business, data management, analysis, ah the more I loved it.
06:01.66
Tracey Windsor
So I was happy to love it. And I… now i and coming out of that wonderful transition that started in COVID.
06:13.11
Tracey Windsor
um Going back to graduate school, starting to work in private equity as an analyst, and then now ultimately um i am, even though I started over again practically in a whole new field, i have a lot of experience under my belt and, um and you know, kind of in my mid-career.
06:33.60
Tracey Windsor
have had so many wonderful ideas about starting something on my own. And that’s what I’ve spent the last year doing. um And I’m having a blast and ah really happy to be working remotely as well.
06:47.46
Lorie Jones
yeah that’s funny I love the idea that but but you didn’t just start in finance like you started in private equity that’s huge that’s like a a really nuanced so did you get your did you get you went back for your master’s is that what you said
07:03.94
Tracey Windsor
I did. i went to um the New School for Social Research in New York City. um i was very fascinated by macroeconomics. And so I wanted to go to a program where I would have um a lot of interesting historical and social ah perspectives and a lot of theory. um And and that that was really something that the the New School focuses on.
07:28.83
Lorie Jones
That’s cool. And what, so I, what, what does Windsor Edge do? Like, what do you, are you private equity or what?
07:38.11
Tracey Windsor
We are not. We are the private equity that um smaller businesses that are never going to get to that, or at least not for a long time, that have access to that kind of um insight of strategy and of growth.
07:45.59
Lorie Jones
Mm-hmm.
07:53.43
Tracey Windsor
And to make it ah to make it available in the sense that I’m aligned with the companies that we work with. So generally, they’re in a space of growth.
08:07.14
Tracey Windsor
creating revenue, automating, cutting costs. We align our revenue with their revenue and help them grow. And it’s um it’s a pretty simple relationship and we focus on AI implementation, stacks and giving companies the competitive advantage with all the new platforms and functionality before everybody else is doing it.
08:32.53
Lorie Jones
That’s cool. That’s really neat. So you’re helping the little guy grow.
08:36.48
Tracey Windsor
Helping the little guy. I hope to help some bigger guys, but we’re focusing more on the employees around zero to 50 right now.
08:38.15
Lorie Jones
I love it. my
08:46.46
Lorie Jones
Oh, that’s really cool. So um I want to know, like, how did you…
08:50.63
Tracey Windsor
Zero to 50? Who’s zero to 50? One to 50. but
08:55.31
Lorie Jones
defect.
08:56.09
Tracey Windsor
ah
08:56.45
Lorie Jones
Got it. Got it. Um, ah how did, how did you get like from, did you ever work as a dancer in New York?
09:06.99
Tracey Windsor
Yes, I still do.
09:09.01
Lorie Jones
Oh, really?
09:09.24
Tracey Windsor
yeah. yeah So I was a fitness trainer while I was dancing so that I could have all the flexibility. I was, um, loved that life running around. i Just did project to project. I, I danced in some dance companies. I traveled.
09:27.00
Tracey Windsor
Um, I did stage productions, video productions, choreographed some others. I just was a dancer, worked with a few artists.
09:35.11
Lorie Jones
Mm-hmm.
09:35.25
Tracey Windsor
Um, nothing, you know, nothing Broadway or Beyonce, but, um, some really amazing opportunities.
09:35.25
Lorie Jones
Mm-hmm.
09:42.35
Tracey Windsor
And, uh, I had a blast. Now i I, choreograph on the side, like it’s my, it’s my hobby. I mean, it’s another thing about my journey. Like I don’t like to, de you know, to, um, to put my life into the narrative that makes sense to everybody around me. so
10:02.82
Lorie Jones
um
10:03.56
Tracey Windsor
so when, you know, I didn’t think about ending my dance career and starting something else. I think about by so by staying um staying healthy, working out, taking dance classes, you know, as my hobby.
10:17.44
Tracey Windsor
um and then sometimes on the weekends or nights working with different artists and coming up with new material, ah you know, I can be ah be an artist and be ah and be in finance.
10:30.49
Tracey Windsor
So, you know, in business.
10:32.15
Lorie Jones
I love that. Yeah, I love that. I think that’s neat. And I think that there’s something to be said for having that creative piece. I think that, um, i I think finance gets a bad rap as like numbers and spreadsheets. And I personally love numbers and spreadsheets, but I also have a lot of creativity. And I think that, that you can integrate and you need both halves of that. You know, it makes you better at your job to have that creative piece and, um and to have that outlet to, to, to,
11:11.82
Lorie Jones
dance and and do that creative piece. So I think that’s kind of cool that you managed to keep that along with, you know, going into finance. It doesn’t have to be like one way street.
11:21.08
Tracey Windsor
Yeah.
11:22.40
Lorie Jones
So I like that. What, what’s the best investment that you’ve made in yourself, Tracy? Is there something that you can look back on and be like, Oh, my goodness, I am so glad I did that.
11:35.56
Tracey Windsor
I guess it’s just this career transition. um I’m glad I i quit a job I loved because I knew that it was kind of a timing thing for me.
11:48.46
Tracey Windsor
i I do think while we can make changes all throughout our life, I’m always looking at what can I do now that I may, that may be a little bit more challenging later. And that gets me to take action quicker.
12:01.84
Tracey Windsor
um
12:02.01
Lorie Jones
Mm-hmm.
12:02.76
Tracey Windsor
So leaving my job during COVID and just bringing more uncertainty to an already uncertain time um by exploring what it would look like to um to switch careers and I loved grad school.
12:17.93
Tracey Windsor
i I really did. um And I did think it it really helped me network. um And yeah, I’m really glad. i it was it was a tough It was a tough road. You know you you go from being an expert in certain things to now being a beginner or to be seen in a certain way.
12:39.36
Tracey Windsor
um and to your peers who have been doing this forever. And you know even in grad school, everybody had
12:43.84
Lorie Jones
Mm-hmm.
12:46.17
Tracey Windsor
was already you know so skilled in in finance and in economics um and already had their path. And I was just starting to figure that out when I went to grad school. So it was just such a fast forward experience to try to say, OK, what’s going to happen next? Because you have to think about that because you’re only there for two years.
13:04.96
Lorie Jones
hu what What drew you to finance? Like, I’m always curious. i I know what I love about it, but like, why? why Most people look at finance and they’re like, I’m not interested. Thanks so much.
13:19.28
Lorie Jones
But it sounds like torture is another thing that I’ve heard. And so what what was what was exciting about it for you?
13:29.97
Tracey Windsor
I think that having, don’t know if this is the right word, but power, but having power over my life, being in a field where I would have a lot of agency in what I’m doing um and also a lot of influence in any organizations or um any types of projects I was working in, um everyone needs that and with such a vast which i had said before everybody every organization you know needs solid finance and needs to understand where they are and how to get to where they want to go and i i thought that was a very powerful position to be in
14:15.26
Lorie Jones
Mm-hmm. To help get them between one place and the other.
14:18.18
Tracey Windsor
yeah to help to be somebody who knows how to do that i thought that was thought that was really cool. And i’ve I’ve had a fun time doing that, especially with smaller businesses. um I helped my friend start um start fundraising. And actually, we raised a million dollars for her startup um in New York City. And it was, i mean, it was amazing creating the business plan, the um you know taking the investor meetings and seeing how strategy
14:49.71
Tracey Windsor
is and having a strategy to be able to talk about it and to have it be based in in logic and in research is how you convince people to do things you know and that’s also a great power
15:04.10
Lorie Jones
What is the worst advice someone gave you? Did somebody ever give you some really bad advice and did you take it? Did you not take it? Did you learn from it?
15:13.70
Tracey Windsor
Yeah. I mean, my career transition seems to be the answer to everything. but i mean, a lot of people didn’t get it. And that’s, that was tough.
15:26.14
Tracey Windsor
I, you know, I got a lot of resistance, a lot of confusion. i actually had a mock interview inn graduate school and the woman who was interviewing me was just like, just don’t get your story. It’s really hard to like, she like almost couldn’t do the interview because it was just so ridiculous that, you know, that I’d gone to school for dance and then, you know, that made this, this kind of shift. And, and I also think that, I think that I got some pushback from people who went traditional routes and i don’t think they liked
16:06.84
Tracey Windsor
seeing somebody do it another way.
16:08.98
Lorie Jones
Mm-hmm.
16:09.14
Tracey Windsor
And I think that the advice was almost more of a like stay in your lane kind of um thought.
16:09.14
Lorie Jones
Mm-hmm.
16:19.13
Tracey Windsor
um I did not take that advice, obviously. um But I think I’ve gotten a lot of career advice in general um to really stay where I am or not to make a move or, you know, see where this goes. And
16:34.20
Tracey Windsor
i um I’m glad I i went and i whenever I got that kind of advice, I just sought more advice until I found the advice I liked.
16:43.49
Lorie Jones
that was kind of resonating with you, right?
16:46.16
Tracey Windsor
Yeah, exactly.
16:49.07
Lorie Jones
What about a situation through your journey that maybe you look back on and you’re like, oh gosh, I wish i I knew then what I know now because I totally would have handled that differently. Is there something you can think of that might be that sort of a situation?
17:11.93
Tracey Windsor
In general, it’s this kind of fear of time that gets me, of time going going by or haven’t gone by.
17:18.26
Lorie Jones
Mm-hmm. Mm-hmm.
17:22.95
Tracey Windsor
um i’m really thinking back to when I was in my 20s was dancing and let confidence and other people’s standards define who I was and what I was capable of.
17:40.83
Tracey Windsor
um And having regret of not pushing forward sometimes has led me to be in a place where that is where regret is how I make decisions.
17:55.28
Tracey Windsor
I look at a decision and say, will I regret not doing this? um Sometimes you don’t get to know what you will regret in the future, but sometimes you kind of do.
18:05.31
Lorie Jones
Mm-hmm. Mm-hmm.
18:07.70
Tracey Windsor
you kind of do get some of those opportunities and you’re like, I will regret this later. So, um so yeah, just letting, letting the fear of, of it’s too late or um i don’t have enough time to accomplish something or get where to where I need so that you almost don’t kind of start the path to get there.
18:29.78
Lorie Jones
here
18:30.47
Tracey Windsor
Um, and I did that, I did that in dance because of, I was in injuries. I really needed to shift, you know, I had a spinal injury actually, and I really needed to strengthen and focus. And it was just a really hard, lonely place being a dancer in, in New York city. And that kind of set me up to be, um, a little bit more aggressive and i think thick skinned kind of moving into more corporate organizations like the nonprofits and and then into finance.
19:01.79
Tracey Windsor
and And I guess, you know, toughening your skin from from past regret or inaction is, I think it’s a good thing.
19:02.25
Lorie Jones
Mm-hmm.
19:09.53
Lorie Jones
yeah Yeah, it is. Sometimes you do need to kind of go through those experiences to really understand. Um, I like the idea of, am I going to regret this later?
19:22.97
Lorie Jones
um like would I, am I, um, is this a decision I’ll regret not making, or is this something I’ll regret not doing? So like maybe projecting yourself into your future.
19:35.37
Lorie Jones
Um, I love that because like it does go with finance quite a bit. A lot of the things that i kind of tell my clients are like, future you will be so grateful you did this.
19:48.18
Lorie Jones
And so i i think that that kind of taking that and putting it in your life and asking what future you is going to think about the decision that you’re making. I think that’s really powerful and a really interesting way to to kind of look at look at what you’re doing and and what you’re making and the decisions you’re kind of trying to make for what future you will think about that.
20:08.62
Tracey Windsor
Yeah.
20:11.13
Tracey Windsor
Yeah, I love that as well, what you tell your clients and thinking more about the the the future you. It’s a more ah kind of tactile, you know, image to think about.
20:25.08
Lorie Jones
will
20:25.95
Tracey Windsor
Visioning yourself.
20:28.05
Lorie Jones
What, if you could go back in time and talk to yourself at like,
20:34.86
Lorie Jones
20, 21, you know, somewhere near the beginning of your journey, what would you tell you
20:42.97
Tracey Windsor
I would tell me I have so much time. I have so much time. don’t do not worry about that. You just have forever. So just go for stuff and don’t worry about how long it’s going to take you to get somewhere because just get started.
21:00.99
Tracey Windsor
um The other thing is to work remotely immediately. Find a way to um whatever you’re doing for money,
21:15.04
Tracey Windsor
There’s so many opportunities in a remote world where you can make, especially in New York City. Like, i don’t this might be a New York City thing where getting anywhere is a very long time, right? You don’t just like, you’re not in a suburb. You don’t just hop to your car that’s 10 minutes in your front. I think that’s a very different.
21:31.24
Tracey Windsor
I, you know, everywhere you go in New York City, just it’s going to take 45 minutes. So if you go 45 minutes here and there and you have to deal with like thousands of people every time you go somewhere. ah Just for me personally, it’s ah it’s a lot of intensity um during my day. So I would tell myself to to get something really cool to do remotely, something you can upscale in um and keep, you know, being able to improve on.
21:57.74
Tracey Windsor
so that you can dance and learn and and all that stuff and and not be traveling hours and hours every day around the city.
22:04.31
Lorie Jones
Yeah, I guess that’s something that, you know, like i I’ve seen it um as I went to a more remote position where I’m like, gosh, you cut an hour commute a half an hour commute off of both sides, like I’m way more productive, but it’s, it’s something that you don’t really think about, and in a practical terms, but if you could put, you know, 45 minutes on each side of your day, plus any lunch meetings or anything like that, that you’re doing, if you could, mm-hmm.
22:34.32
Tracey Windsor
And schlepping all your stuff. Anybody doesn’t know schlepping is caring in Yiddish. Carrying it all around. mom would say schlepping the schmata, all your crap.
22:45.94
Tracey Windsor
Throughout the city, it’s like my life in the summer. so it’s a very specific 20 year old um New York City gal who doesn’t like to commute kind of advice.
22:57.40
Lorie Jones
Do you think you would have missed out on that? that That’s always the kind of the the question I have, the balance that I have is that I got a lot from just being in the same place as other people kind of learning what they had to teach me um sitting in their office and chatting with them. Do you think you would have missed out on that if you had, if you had gone fully remote right at the beginning?
23:21.19
Tracey Windsor
my gosh, probably. Great point. um Yeah. Yeah. I mean, I think that we’re seeing the outcome. of people having there the young parts of their lives remote, right?
23:35.49
Tracey Windsor
In their 20s and 30s and the challenges that they might have more than others in certain social situations and um certain parts of of work that you learn when you’re in person with people.
23:48.81
Tracey Windsor
So that definitely but definitely could have been the dark side of going remote at 20.
23:54.82
Lorie Jones
ah
23:55.63
Tracey Windsor
But I’ve met some people going remote at 20.
24:00.24
Tracey Windsor
You know, I’m at,
24:00.44
Lorie Jones
how did they get around it how did they how did they get that same sort of experience or or make room for those same sort of skills do you know
24:09.08
Tracey Windsor
you know what, now that I think about it, kind of a couple of people I really knew back in the day, you know, so that was like over 15 years ago, right? And being 20, they’re, they’re a little bit, you know, not so outgoing. So I don’t know if they really did, were capable of,
24:26.16
Tracey Windsor
kind of getting all the advantages of working in person. So gosh, I guess if you’re going to, if you’re going be remote, you better find great community and projects and and reasons to be doing and doing complex things with people in person. Cause it’s not just being in person, right?
24:41.28
Lorie Jones
Yeah, right.
24:41.68
Tracey Windsor
It’s about the challenges at work.
24:44.23
Lorie Jones
Yeah, that’s a good point. Like you can maybe you can condense that all that in person this everything that you’re going to get from in person from eight hours worth of mostly wasted time to like one hour worth of really concentrated effort.
24:57.79
Lorie Jones
I like that.
24:58.12
Tracey Windsor
I mean, this, yeah, I mean, I think this is, this question is going to be, and this balance is going to be, just continue to evolve and, and have discussions around and debates around.
24:58.25
Lorie Jones
That’s an interesting idea.
25:10.97
Tracey Windsor
i think in the coming years, like in the next 10 years, we’re going to start seeing some, hopefully some really cool ideas about how to be very remote or, um mean, honestly, what about great transportation?
25:22.61
Tracey Windsor
Can’t we get better transportation, especially, in cities so that people can get to a meeting you know quicker and have more express trains and have more buses running um and just just you know make make all us little guys have an easier time getting around.
25:39.67
Lorie Jones
Yeah, I was i’m was thinking like the, I’m going to date myself here, but Jetsons, you know, they used to like just get in their little airplane and fly their cars around.
25:50.92
Lorie Jones
Like I always, I always wanted one of those flying cars. I really wish they had, they’d figured that out before and now.
25:57.22
Tracey Windsor
Yeah. In the fifth element.
26:00.89
Lorie Jones
hmm.
26:01.36
Tracey Windsor
You know that movie?
26:01.31
Lorie Jones
Mm hmm.
26:02.36
Tracey Windsor
They had great flying cars in that movie, too.
26:02.51
Lorie Jones
Mm hmm. Yeah.
26:04.89
Tracey Windsor
Yeah, it’s unfortunate we’re not flying yet. I think that’s a real real loss that we’re not flying yet.
26:11.31
Lorie Jones
Yeah, we can
26:12.57
Tracey Windsor
Very disappointed in technology.
26:14.78
Lorie Jones
we could get some of those college graduates to get us some flying cars.
26:17.73
Tracey Windsor
is a flying
26:18.38
Lorie Jones
That would be amazing. What about, what scared you the most when you started out on your journey? Was there anything that scared you then? And does it still scare you now?
26:28.89
Lorie Jones
Or did you learn how to overcome?
26:30.78
Tracey Windsor
Oh my gosh, everything scares me, to be honest.
26:31.35
Lorie Jones
Yeah.
26:34.09
Tracey Windsor
am always like, what’s going to happen? i guess that’s the antidote to to boredom is is you know not knowing what’s happening or or being scared. um So I guess I put myself in those situations.
26:49.79
Tracey Windsor
um But yeah, think going for high achievements, going going to achieve something that not a lot of people get to achieve. um You know, first that started out in in dance.
27:02.09
Tracey Windsor
It’s very competitive space in a very competitive city um into, you know, graduate school is extremely competitive. Who gets opportunities, who doesn’t, who’s in leadership roles.
27:14.43
Tracey Windsor
And then, yeah, into into finance. i it’s it was It’s tough in the job market. It’s really um really hard to be seen and and hard to be seen for your uniqueness that you aren’t, you know, if it’s not those awesome things that everybody wants in those in their resume, you don’t have the name of the school or the employer, it’s really hard to be seen, you know, and just, I had a fear that I wasn’t going to be able to put myself in front of people, have the opportunity or find the right people to see my value.
27:33.14
Lorie Jones
Mm-hmm. Mm-hmm.
27:48.13
Tracey Windsor
and to see what I can bring to the table. i think, because I always knew I could do really cool things, but it was hard to express that, to have opportunity to show, you know, all those types of things. One of the reasons why I have a podcast is because um connecting with people on a level where you can really find value outside of um some of those very kind of corporate qualities or names that people look for.
28:16.05
Lorie Jones
hmm. Mm hmm. To kind of connect on a deeper level. Yeah. Yeah.
28:22.62
Tracey Windsor
Yeah.
28:23.01
Lorie Jones
Um, did you face any unique challenges over your journey because you were a woman?
28:31.97
Tracey Windsor
Yes, I did. It’s so, you know, it’s hard to know. and I think as a woman, I second guess myself and oh is this really because I’m a woman or is it just me?
28:45.77
Tracey Windsor
think I had a lot of those experiences. those kind of fighting moments with myself. And usually if you’re asking yourself that, it’s probably not you, you know, like if you’re someone that always blames yourself and is hard on yourself, um then, you know, you’re always going to err on that side like me, you know?
28:53.78
Lorie Jones
Mm-hmm.
29:01.43
Tracey Windsor
And, um but i I see it when it comes to like business development, ah networking. um i you know, i I think that there’s a lot of opinions about me just from what I’m wearing and what I look like.
29:23.33
Tracey Windsor
um And those things being connected to to being a woman. I think people talk to me a certain way. i think at work, you know, in some ways people were more sensitive to me, which is could be better in private equity.
29:41.09
Tracey Windsor
I think it was such a male dominated space.
29:41.28
Lorie Jones
Mm-hmm.
29:45.79
Tracey Windsor
It is a male dominated space. And in a small company, when it’s kind of men and those in the type of type of positions that you have in my last job, um there were women in the company, but usually in you know and in another department.
30:00.61
Tracey Windsor
um So there was a sensitivity, actually, which I think is really great. It was kind of positive for me. They were like, wait, what? It’s like having a woman almost like ups the ante of what could go wrong.
30:13.32
Tracey Windsor
um And this is like from a society, not from that.
30:15.24
Lorie Jones
Uh-huh. Mm-hmm.
30:16.32
Tracey Windsor
that that experience is that I’m just thinking, you know, why, you know, a company might might go towards that. um But, you know, mostly whenever I felt that throughout my journey that I was being looked at a certain way because I was a woman, I just, I moved so quickly away from that.
30:37.98
Tracey Windsor
um
30:38.18
Lorie Jones
huh
30:39.54
Tracey Windsor
So if I hint it, I leave that space. but In terms of like really feeling, know, uh, obviously weighing the benefits of, of being somewhere going through an experience.
30:52.95
Tracey Windsor
Um, but anything where I can find the version where people will lift me up or not, you know, not treat somebody differently. and just always opted for that to try to, to try reduce, um, kind of the impacts of, of being a woman and trying to be, uh, achieving things and, you know, become a, ah become a leader.
31:15.15
Lorie Jones
Mm hmm. That’s interesting. and but You just talked a little bit about like, you know, feeling like in a space where maybe you it you were feeling a certain way or you you had these negative feelings and you’re like, yeah, this that helped you to know that this wasn’t the space for you. Like you like they weren’t going to lift and grow in that space. Is that kind of what?
31:43.10
Tracey Windsor
Yeah, absolutely. That, that feeling also, i think for me, I had like kind of two things not going for me. One was being a woman and then one was my background.
31:54.00
Tracey Windsor
And think I might’ve faced resentment for both of them.
31:54.60
Lorie Jones
Mm-hmm.
32:00.62
Tracey Windsor
Uh, and, um, right. People have so many resentments to, to bring to you and to judge you about. So, ah But yeah, trying to trying to move, um shift somehow or something, right? You can’t always have the power to to make big changes. And also, you know there are certain situations, certain jobs that you know it’s not so smart to move every year in a new in a new job and weighing that with, hey, what does my resume look like? And how many years should I be here? And you know all those things that you have to think about and you have to weigh. And I um definitely a proponent of sacrificing
32:40.20
Tracey Windsor
sacrificing certain things. So I definitely don’t want to come ah across as like, yeah, I just keep shape shifting as soon as something doesn’t feel right, because, you know, that’s only half the time.
32:50.61
Lorie Jones
right Yeah, right, right. You do have to um kind of dig in and and make things work and and face some of the issues or the problems that and work them out.
33:02.18
Lorie Jones
Yeah, that sort of thing. um What is the thing, Tracy, that you are most proud of?
33:10.53
Tracey Windsor
most proud just sacrificing so much comfort in my life for the future.
33:22.05
Tracey Windsor
i Just, yeah, really proud for making choices that were less comfortable, that are going bring knowledge, experience, opportunities to me or to communities I care about later on.
33:40.71
Tracey Windsor
And now, now that I’m proud of that, I also do want to find some comfort and some finer things in life. So while I am proud of it, I, I love a world where I didn’t have to sacrifice a lot, but, um but I’m, I’m certainly, I’m certainly proud that i that I did, especially to be living in New York city, a big city and,
33:59.02
Lorie Jones
Mm-hmm. Mm-hmm.
34:09.67
Tracey Windsor
where you get to network with the coolest people. There’s cool people everywhere and um there’s awful people everywhere, but yeah, there’s some really, um really talented people in New York city and wanting to rub elbows with them and, and have some of the way they, if they’re amazing talkers to have to speak with them. So you can start to learn, you know, how to rub off on how to have that rub off on you. Um,
34:37.69
Tracey Windsor
if they’re a writer, to be able to engage with them on on that level, to read their work, to talk about that, right? You just like, you turn the corner and there’s just like authors and actors and, you know, CEOs and just um extremely accomplished people in in very regular clothes.
34:56.47
Lorie Jones
Mm-hmm. That’s kind of neat. It’s, I, I always have been really excited to learn from other people and to learn from their experiences, um you know, obviously. So I i really enjoy kind of, um so I’ve had it phrased like spending time around people that are who you want to be.
35:17.11
Lorie Jones
and and you can kind of, yeah, some of it rubs off on you or you just spend time around really talented people. you you tend to notice what makes them so talented and try and emulate that.
35:30.63
Lorie Jones
So I like that.
35:31.13
Tracey Windsor
Yeah, absolutely.
35:31.68
Lorie Jones
That’s neat.
35:32.05
Tracey Windsor
I, you know, and I have one more thing I’m very proud of. So being a dancer, i came to a point where it was such second nature to to express and experience emotions while dancing, while choreographing, while engaging with other dancers. It was such a great space to communicate.
35:53.16
Tracey Windsor
And you have your own language. And it feels, you know, you go to a dance practice rehearsal, um And you come out of that and you feel like you had some, ah you know, that, oh, I had a had a very, you know, cathartic discussion was it’s like, no, you didn’t you danced. And that was the feeling of the music. So you thought of things and then you had, you know, you worked through stuff. So it’s, I mean, that’s really cool.
36:16.86
Tracey Windsor
But I was very afraid of writing. really felt like it was so, that i I could not write, I could not express myself through words generally.
36:21.71
Lorie Jones
Mm-hmm. Mm-hmm.
36:30.14
Tracey Windsor
um But I did think it was very cool writing how you could really craft your words in such a way that um you know, that you can really make the point you wanna make. um And that was something that I worked really hard on to become a writer. And so through grad school, I did find opportunities to start to publish and um and now have found a really cool unique um niche in my research that um i’ve been publishing it’s in the uh it’s in animals in supply chains global supply chains using the case study of the fashion industry and it has been um such a
37:15.67
Tracey Windsor
such a great thing to be, start to be known in, um you know, for a certain field. And so I’m really proud to to now be able to call myself a writer.
37:25.33
Lorie Jones
that’s cool that’s really neat and you practiced and practiced or you know just did it and and um and then you could show up in that way and and have that talent um It didn’t feel like it came naturally to you, but you you had to work at a little bit.
37:44.36
Lorie Jones
That’s cool. Yeah.
37:47.05
Tracey Windsor
Thank you.
37:48.59
Lorie Jones
Any advice Tracy, for a young woman who’s just starting kind of down this path, I’m not sure i could find a young woman who started down the path of dancer to nonprofit to ah private equity.
38:03.27
Lorie Jones
But that um say she’s starting out on the path to where you you know you know you ended up in owning your own business and kind of doing private equity. What advice would you give her?
38:14.49
Tracey Windsor
Oh yeah. Big time. It’s all about people, people, people. So the people who are not serving you, it’s tough, but at least find some space.
38:25.54
Tracey Windsor
Right. And then finding people who are where you want to be or to know about something. Um, just bringing people into your life, bringing mentors into your life.
38:36.94
Tracey Windsor
Um, coaches, right? So whether you have mentors who just want to you know, give back by taking care of younger people in a, in a way that, you know, can help them evolve their career versus paying for a coach. I don’t know, do all of it. Honestly, i think the more that you can get people in your corner and helping you craft your transition and craft your next steps.
39:02.02
Tracey Windsor
um I think it’s the most valuable thing. thing to be focusing on is your, your people lens.
39:09.73
Lorie Jones
I like that. um And how do you find those people? Like, they walk up to them on the street? Or do you, like, how do you find those people?
39:19.36
Tracey Windsor
Sometimes super randomly.
39:21.08
Lorie Jones
Mm-hmm.
39:21.76
Tracey Windsor
Um, Gosh, I think I find them and in ways that I don’t know I’m going to find them, but also, you know, anywhere from, yeah, walking up, like literally meeting somebody in one circumstance, you had no idea that you know, they also had this um this knowledge or this career, this network that could help you, right? And it just is kind of a natural thing to fully researching, and you know, a space to to get the job. oh this is huge. To get the job.
39:51.27
Tracey Windsor
to get your first job or your second job or any job when you do not have a traditional background, I hired a career coach, a job coach, and worked really hard, really hard on every aspect of that job search um and fully fully committed to that.
40:09.39
Tracey Windsor
um And as well as just being a woman, learn how to negotiate also. All of it in the people lens, but learn learn how to negotiate.
40:20.04
Tracey Windsor
and And that was also something I learned with my um my job coach who was a all of the things.
40:25.15
Lorie Jones
Negotiate salary or
40:29.53
Tracey Windsor
All of the things. Yes, I learned it because I wanted to get a better salary than I knew I would be offered.
40:35.48
Lorie Jones
Mm-hmm.
40:35.67
Tracey Windsor
um and And then in general, I mean, I learned that in finance, the whole, everything that we’re doing is negotiating. um the best negotiating happens when you say you’re not negotiating and it’s under the veil of, oh, we’re just seeing, we’re just trying to make everybody get what they want in this business deal. And it’s, everything is a negotiation and people who say that are generally very good at negotiating and are negotiating when they say that to you.
41:05.53
Tracey Windsor
um So yeah, in all all aspects.
41:10.15
Lorie Jones
That’s so interesting. um Where do you find a negotiation coach?
41:16.79
Tracey Windsor
Well, I think for me, it was the, you know, ah getting one out of a career coach, right? It’s very, that’s very targeted at specific types of negotiating.
41:29.72
Tracey Windsor
But I also found my working in private equity, seeing people in leadership positions engage in some really tough negotiations, just witnessing it, being in the room, being on the phone call, um putting yourself in situations where you get to you get to see it and then potentially behind the scenes,
41:45.53
Lorie Jones
Mm-hmm.
41:55.17
Tracey Windsor
can hear the reflection, you know, internally and be like, oh yeah, that did happen. um Because I don’t think we see negotiation so clearly. Not only when we’re doing it, do we say we’re doing something else, but I think the tactics and not in like a sly way, you know, like sneaky, I need to get what I want, but in truly trying to figure out what other people truly want, right? What is the bottom line for the person you’re negotiating with?
42:24.51
Tracey Windsor
Those things I really did learn um on the job and just seeing people beat tough cookies every day and sit in silence for a moment, like letting the silence happen and let the other person sweat a little bit.
42:37.19
Tracey Windsor
And I just loved seeing little things like like that.
42:41.51
Lorie Jones
That’s interesting. And I think it’s interesting to think about like afterwards, like the wrap up or behind the scenes. It’s so interesting to kind of understand what other people are doing and and why and have them help and and just explain ah questions, you know, like just asking questions after things like that so that you can get better and understand what’s going on. so Well, thank you so much, Tracy, for helping us and for just explaining your journey and letting us take a little a little journey along with you to kind of um get your insights.
43:03.88
Tracey Windsor
Right.
43:16.48
Lorie Jones
If I have a young woman who wants to reach out to you, how does she do that?
43:22.08
Tracey Windsor
I think LinkedIn is always great. So Tracy, T-R-A-C-E-Y, Windsor, W-I-N-D-S-O-R.
43:30.72
Tracey Windsor
And um my email is Tracy at Windsor dash edge.com. um Yeah. So find me happy to chat.
43:40.52
Lorie Jones
Perfect. so Well, thank you so much for your time. I appreciate it.
43:45.15
Tracey Windsor
Thank you, Laurie.