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About This Episode


ennifer J. “Yay” Hammond joins the Student Loan podcast to share her inspiring story. Not only did Jennifer pay off all of her student loans with one real estate flip, that wasn’t even her original game plan after graduating from college. 

If you’ve ever been unsure if you are heading on the right path and if you’ll ever pay off your student student loans, then this episode is for you. Jennifer J. Hammond shares how a rough start in life didn’t prevent her from pursuing her goals and dreams. 

As a Vice President of TTR Sotheby’s International Realty – one of the country’s leading real estate companies – she has helped her clients attain their dreams in real estate for over 24 years, has helped make the world a better place by educating, inspiring and empowering people by hosting The Jennifer Hammond Show on SiriusXM for over 10 years, and has aided veterans and their families in finding the help they need through her best-selling book “101+ Resources for Veterans” (Now, the 2nd edition of 101+ resources for Veterans is published).

However, the path to her success was not an easy one. Though she is the granddaughter of a woman who escaped Poland during the War and is now enshrined in the Baseball Hall of Fame, Jennifer grew up in a broken and abusive home and was repeatedly told she would never amount to anything; and that opinion was further impressed on her when in High School she was told by a guidance counselor that she “was not smart enough” to attend college or be in college prep classes. Nevertheless, determined to make something great of her life, Jennifer never gave up.

Not only has Jennifer mastered the art of real estate, but she also became a highly successful talk-show host for SiriusXM for ten years. Today, Jennifer likes to cover a wide variety of topics relating to real estate to better educate her listeners through her YAY! The Jennifer J Hammond Podcast that you can listen to through SpotifyGoogle PodcastApple PodcastiHeart  Radio and Youtube.




  • How exactly Jeniffer J. Hammond paid off her student loans with 1 real estate flip;
  • How Jennifer overcame adversity at home to achieve her goal of attending college;
  • The importance of financial advice and associating yourself with others that can teach you;
  • How to stand for something, so you don’t fall for anything;
  • and
  • much, much, more…

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Jennifer J. Hammond (00:00): And it was super funny because I learned so much and I did, I got invited to a lot of places that I would never been invited before. And I learned to associate with people who were flipping properties and I was like, oh, I wanna learn. So my first flip, I ended up paying off my entire student loan.

The Student Loan Podcast Intro (00:22): Welcome to the student loan podcast.

Shamil Rodriguez (00:25): Here. You'll find practical advice on tackling student loan debt, paying down your higher education expenses

Daphné Vanessa (00:32): And inspiring stories about paying off student loans, where your hosts, Daphne, Vanessa and

Shamil Rodriguez (00:38): Shamil Rodriguez,

Daphné Vanessa (00:41): Please rate, review and subscribe to the student loan podcast by visiting the student loan podcast on apple podcast or wherever you find your podcasts.

Shamil Rodriguez (00:51): This is not professional advice. And we speak from our own personal views and opinions.

Daphné Vanessa (00:57): The student loan podcast is brought to you by start new, where you can serve your community and get rewarded with tuition and student loan payments to check out if start new is on your campus, visit start new.com. Welcome everyone to another addition of the student loan podcast. Today, we have an incredibly special guest. We have none other than Ms. Jennifer Hammond, who is here to share with us a really inspiring story. And I hope that you guys are enlightened by how far she's come. All of the things that she's done and so that you can put that into your life. So without further ado, Jennifer, please introduce yourself. Yay.

Jennifer J. Hammond (01:42): But as you know, I'm known for my yay and I'm known for celebrating everything from the big wins in life to the tiny little ones, which I call the micro yays, because we all need to celebrate the little things that we have done, right. And sometimes that's all it is. Sometimes we get some challenges in life. And I came from a really tough childhood and, you know, my mother was, um, you know, she was one of those people who unfortunately, um, really discouraged me from going to college. And she just said that I was too dumb. She said, I, I would never make it in college. And, um, wow. She was an alcoholic and a drug addict. So it wasn't like, um, you know, she just, wasn't always in her best mind. She wasn't her best version of herself. And she was a really interesting tortured artist, unfortunately.

Jennifer J. Hammond (02:29): Um, you know, she died of cancer years ago, but it was an interesting one because then when I finally, I finally got a scholarship for my first two years of college, and then I was like, wow, that was way more than I ever thought I was gonna yeah, have. And then I got a scholarship for my bachelor's degree and I was like, no way. And then of course I had moved to, I had gone from key west and then I moved to this little town called Pensacola, Florida to the university of west Florida. And we, I realized even though you'd think that the difference would make such a big difference, but boy, it made a huge difference in trying to balance all the other expenses that I had never had to balance as much. And I think even just because I was mostly waiting tables and I worked three different jobs while I was in college, I worked for a law firm during the day, and then I had a student job and then I waited tables at night.

Jennifer J. Hammond (03:24): So I had three jobs and I racked up student loans. Cause of course, then they said they would gimme a partial scholarship for my master. So I stayed and I went on for my master's as you know. And so I have a master's in public administration and then like many people I got the job I thought was the job of a lifetime. And I got, um, asked to work for Congressman on Capitol hill. We won't go into all of the details. Although if you look it up, there are some newspaper headlines that people won't forget. My Congressman got in a bit of trouble and it discouraged me from wanting to be in politics or quite frankly in government. And I remember I was so sad. I remember walking across the street from where I was working for the house of representatives. And I went to the library of Congress.

Jennifer J. Hammond (04:17): Library of Congress actually has a couple buildings. Most people don't know that, but I went into the reading room, which is this gorgeous building and this room that has this gold dome on it. It was amazing. And there's beautiful librarian in there. And she said, you know, how can I help you? And I said, well, I have a master's degree now. And um, I don't wanna work in that field. And I have a bunch of student loans and I don't know what I'm gonna do. And I think I probably look like I was on the verge of tears. And she said, well, we have a whole room of all sorts of careers. You can just pick a new one.

Daphné Vanessa (04:50): I love it. So inspirational. So positive. Right? As you're in this huge pivot,

Jennifer J. Hammond (04:55): I'm like, I dunno what I'm gonna do. I think this is all terrible. I think my whole world is falling apart and falling down on top of me. I felt so devastated. So I sat there and I was going through everything and I have to admit now, not everybody likes this part of the story, but I'm gonna confess it. I did get to circus clown and thought, wow, is there really a job where he could get paid to be a circus clown? of course, ironically, I had a fiance who was working in the white house. He did not find that funny in the least, but I thought it was a really, it was great because it made me think outside the box where I never thought all I'd thought about was I had spent all this money and time getting this, you know, an associate's degree and then a bachelor's degree and then a master's degree.

Jennifer J. Hammond (05:42): And now I've got all this debt and I gotta figure out how to pay it off. And I'm realizing that the government jobs aren't really going to, I'm gonna spend the rest of my life paying off this student loan debt, and I don't know what I'm gonna do. And so finally I got down to R and I saw real estate and I was like, oh, I've always wanted to be a real estate investor. And I thought, well, that's the way I could pay it off. I think I could do this. So I went ahead and I, I, I started learning a little bit about real estate and then I found out, and I gotta remember now I've been in real estate 25 years. So 25 years ago, a young 20 something year old woman, they were not very, um, friendly or willing to teach me.

Jennifer J. Hammond (06:28): So I decided the only way to kind of sneak in the side door, if not the back door of real estate investing was to become a licensed real estate agent because at least then I would learn all the terms and I would learn what I needed some of the basics at least. And it was super funny because I learned so much and I did, I got invited to a lot of places that I would never been invited before. And I learned to associate with people who were flipping properties. And I was like, ah, I wanna learn. So my first flip, I ended up paying off my entire student loan and it was hilarious. Whoa. It was amazing cuz it was, for me, it was, and this is again, 25 years ago, it was almost $40,000. It was like 30 huge 7,000. It was a lot of money.

Jennifer J. Hammond (07:14): And again, you know, back then with that, I mean just everything of course is different 25 years later. But it was probably what I would say. I don't know if I could do the inflation math, but it was like having a $300,000 loan now. I mean, it, it was that, that was what it cost to buy a one bedroom apartment in Washington, DC. Then you can't buy it now, but that would give you the equivalent. My goodness. So the I had in debt, the amount it would cost you to buy your first property. And I, I remember thinking, oh my gosh, how am I ever gonna buy a property here? I am a licensed real estate agent and I can't afford to buy a property because I've got so much student loan debt. So now I'm in an industry where I'm not practicing what I preach.

Jennifer J. Hammond (08:01): So for me that was my number. One thing is how do I pay off this student loan debt so that I can actually buy a property and you know, do what I'm saying? You know, I'm a salesperson which I hated that term. And I was like, oh, I just wanna be an advisor for people. Anyway, long story short, I am so grateful that I discovered real estate and that I discovered real estate investing specifically. And now I love it. You know, now I love education. I love teaching about media and how you can, you can leverage media to understand and to educate people because so many of us, we didn't get the full education, especially not about financial literacy.

Daphné Vanessa (08:49): I agree. Completely agree. So that was, I mean, so there are so many ways we can go, I wanna start at the beginning just on mindset because you had to have a really strong mindset to get through some of the things you got through when you were younger and then to pivot when you've invested all of that money in a degree and you've gotten on the hill, which for so many people is you've made it. Right? Yep. Talk to us about mindset, the evolution of your mindset, how you kept it sharp, how you kept going, despite all of the struggles that you faced.

Jennifer J. Hammond (09:26): Thank you. I think one of the neatest things, when I look back on it now is like when I got to Capitol hill, I remember thinking, oh my gosh, I'm a little island girl. I grew up in key west. I don't know what I'm doing in this big city. Like this is, this was just like, it was a dream come true, but it was also so surreal. And then when I started seeing things around me that were being done that were unethical and wrong. There's something, I think that every one of us even like when I was a child and you, you know, you're like, wait a minute, your mom, shouldn't say those things to you that you're too stupid. And that you're not smart enough to go to college. I wasn't even smart enough in her eyes. I wasn't smart enough to finish high school.

Jennifer J. Hammond (10:08): And it was so interesting because I realized, well, you have to go inside yourself and realize that you are good enough that you are enough, which again is something that we all struggle with. No matter where we are in life, is that, did I absolutely. You know, am I enough? Am I, am I doing this right? You know, what could I have done better? And I think that you, the more that you ground yourself and what you know for sure is right. Like I knew for sure, my Tim, my mom, it was not right the way she was treating me. And so one of the biggest things was just the bravery of trying to stand up to her. And as a child, I don't think I did so well. There was three of us. And my, my older brother I think was the best at standing up in my, to my mother.

Jennifer J. Hammond (10:53): I was, I was much better at running away. And I think when I got to Capitol hill, one of the things is when I started to see things that were not being done. Right. I realized, okay, you know, like that old saying, if you don't stand for something you're gonna fall for everything. And I realized that that's one of those things is as a mindset I needed to be able to stand up. And what kind of life was I gonna have if I couldn't do that from the beginning. And so that's why I just realized that. And you also like, and I talk about the micro yays and on the, all the yays, you know, a lot of times people ask me, where's the origin story of the yays. And I'm like, because I used to have silent yays, like as soon as my mother would leave the house, when she was super like being violent or whatever, it's like, yay, she's leaving.

Jennifer J. Hammond (11:40): Oh my gosh. You know, you're like, and then it was so funny because you learn to find the silver lining in things when, when it doesn't seem like it, it's just like, if you've been in a really, really nasty storm and all of a sudden you look up and you see like a double rainbow or something and you're like, whoa, yeah. If it wasn't for that storm, you wouldn't have that incredible rainbow. And so, yeah, there is beauty and there is something to be learned in every bit of every challenge that we ever face. And part of it is, is just trying to see if you can find your yay, whatever that little micro yay is, or if it's a big yay, then, then really celebrate and throw your, you know, arms in the air and just go for it with your yay. But I think one of the things is like, you know, walking across the street and feeling so defeated, um, as I was walking into the library of Congress and then that librarian, she was just like, so excited.

Jennifer J. Hammond (12:36): Look, I have so many options for you. It's we're looking around this big, beautiful room and this gold dome. And I was like, really? I mean, I, cuz I felt completely closed in and helpless and just, I mean boxed in financially, not having how in the, I have no parents, one, they don't feel like they there's any way shape or form. I have no parents that are gonna help me get out of this financial hole. Oh my gosh. I mean, and they, and my mother would've loved for me to have called her at that time. So she could revel in, in the fact that I was so stupid that I had taken out student loans, you know, and I think about it. We don't really necessarily get a lot of financial advice when we're signing on the documents for our student loans. True

Daphné Vanessa (13:18): Story. True story.

Jennifer J. Hammond (13:20): O dear, how are we gonna pay this back? What is our plan? Even if we had some options, but I had, I mean, they were just so easy, like here a sign right here and then handing you a check and you were like, okay. And of course, I'm sure you guys don't get a check now, but it was just, it was so funny. You like this massive check, you holding your hands was like, what? You're gonna give me this check. Okay.

Daphné Vanessa (13:41): It's it's such a situation because I think you, you hit it on the head, right? Financial literacy. Would've been key, especially because not everybody has the same safety net. Right. So I love that you took it into your own hands. You said, all right, I made this slight mistake and we can't even call it a mistake. Right? Because you got the degrees that got you to where you ended up going, right. So maybe if you didn't have that experience on the hill, you may not have walked into the library. And then you wouldn't have found real estate, which is just talk to us about real estate because paying off your student loans like that. I mean, I think the only other person that we've had on we've had another real estate person. Um, but besides real estate, there's been like a record deal. Like those are the large lump on payments. And you're telling us that real estate is like a record deal. Tell us more.

Jennifer J. Hammond (14:33): It's it's like a record deal. It's the most amazing thing is really understanding. Again, to me, it's like a puzzle piece, you know, you go, oh, I got a puzzle piece of this and then this puzzle piece, and then you put them together and then the profit can be so substantial. It it's unreal. You know, I, I mean for me and I think I, I started to share this story. It's how we ended up finally booking. This one was my very first, um, investment deal. I went to buy it and it was this again, it was a condo in, um, Washington DC in this area called DuPont circle, which is kind of right in the middle it's right next to one of the Metro stops. And so it was a great location. And what I had started to learn was, again, there are puzzle pieces and like anything else, there's indicators on what to do, whether you're doing a good job or a bad job when you're going into real estate.

Jennifer J. Hammond (15:23): And one of the things I was looking for, of course, I know it's location, location, location, but even within a location, like you could have a location in Washington, DC in a block. And it's a great block because it's close to the Metro, great check. It's close to the Metro. However, then you find out you have two buildings that are right next to each other. One building has terrible management. So the condo fees in there are like three times the price. So you're not gonna be walking away, making a whole bunch of money because they're hidden pitfalls in there. So you have to really be able to put all the puzzle pieces together. Because again, those two buildings that would sat right next to each other, they would definitely not give you the same return. And I remember that. I also learned one of the things that I think if there was a piece of advice for people who are getting into real estate and thinking, well, should I do this or should I not?

Jennifer J. Hammond (16:17): First of all, again, you should create your yay team. As I call it, everyone on your team makes you go yay. In some way. Yes. Every day you're gonna say yay every day. . And what I mean by that is your tax person, your, um, the attorney, your real estate agent, the all sorts of people that should be on there to give you advice and guess what? They're not all gonna agree. And they're not all gonna give you the same advice. And that's where you become the queen. You become the person who gets to pick and choose on what advice of that you are going to agree with. And you're gonna figure out whether that's true for you, because I can tell you if I had taken the advice, the name, I shall not say out loud, cuz he's still around. But the one person in my office in my real estate office told me buying this first property was a stupid idea and that it would be a, a money pit and you know, just on and on.

Jennifer J. Hammond (17:14): But I decided not to take his advice. I went ahead and I asked someone else and then I asked someone else and then I started investigating for myself. And what I found is then again, you need to find out about that particular building. Are they financially healthy? Do they have, you know, finances that are in reserves, find out if that one is the right one for you. And so I went in, renovated the place and then I rented it for, it was exactly a little over two years. And there's an amazing tax benefit for people who buy a property. And if you live in it for two years, then when you go to sell it. So say for instance, just for easy math, you buy something for a hundred thousand and then you sell it for 350,000, which I know sounds absurd, but that means you're making a capital gains of $250,000. Well, it's the only thing at least that I'm aware of. And I'm not a tax accountant, but the only thing in the tax code where you pay no capital gains tax on, it

Daphné Vanessa (18:19): Love at

Jennifer J. Hammond (18:20): All at all. You can do that over and now you have to have lived in it as your primary resident. So you can't do it just as an investment property. So this is one of those things that, again, by building my, a team, my, I called it my yay team. I called it a team in the beginning and then it turned into yay team. because they should make you say, yay. So I learned that you could sell property and, and not have to pay any capital gains tax, as long as it's not over 250,000, which, you know, God bless you. If you're making over 250,000 with one property and, and you might be, but still as a married couple it's 500,000. So these are amazing little insights. That again, until I started asking the question, so you asked me in the beginning, so what is it? Number one, you have to find your way of finding your yay every day, whatever that is. And for me, it was looking for the rainbows for the silver linings. And then number two, it's continuing to ask questions even when you don't like the answers, but not just accepting one person telling you yes or no, ask again and then ask again and find out fully. Because again, everything changes.

Daphné Vanessa (19:33): Absolutely. Oh my goodness. This is a, a masterclass. This is a session by itself. I think one, the advice on just living in a property and then selling it within the two years for the CA that's a piece of advice that maybe we haven't shared on the podcast yet. So I love how there are lots of different ways, right? That people can look to pay off their student loans that you may not have heard about. So thank you for sharing that information. I think that your real estate background is super unique in the sense that you've used it both on the investor side and as an agent. Yeah. Talk to us about sort of the nuances and how you went from agent to investor and where are you today in, in your success path?

Jennifer J. Hammond (20:21): Thank you. I love so when I got, I was telling you about when I first got into Washington DC, they were not super welcoming to a young 20 something year old woman wanting to come into real estate investing and nobody would share their knowledge. So I snuck in the side door of real estate by becoming a licensed real estate agent. And what I realized is, again, I was so hungry for knowledge and I had so many of my friends who were like me, we were making next to no money. And we had huge student loans. And one of my, I have one really good friend. He was, he worked for a nonprofit and he is like, Jennifer, I don't, I don't think I'm ever gonna be able to buy a home because you know, I I'm doing, I'm living my dream. I'm working for the nonprofit that I've always wanted to.

Jennifer J. Hammond (21:04): And I'm always gonna make barely enough money to even buy my groceries, but I'm gonna do what I love. And I said to him, well, what if I could show you how you could buy a house? And I would get someone else to pay your closing costs, someone else to pay your down payment, someone else to pay, you know, all the different things that need to be paid, all the cash out of pocket. And what if I could show you a government program where you don't have to pay any real estate taxes for five years? And he just looked at me and he said, I'm listening. And I said, okay. So what we're gonna do is we're gonna put together, there's a grant for your down payment then there. And I went together and I put all these programs together in Washington, DC. And we did again, we bought him a house with no money out of his pocket, zero money out of his pocket.

Daphné Vanessa (21:53): Oh my

Jennifer J. Hammond (21:53): Goodness. And he got to continue of course, working for his, uh, the dream job that he loved. But the greatest part that I loved is a couple years later, he got to have the dream wedding he wanted because he had his money and his real estate property had gone up so much. And he got to go on a mission to Africa. He had always wanted to go on again because he had his real estate had gone up so much. He had so much equity in the real estate and you know, and he paid off his student loans. And so, you

Daphné Vanessa (22:25): Know, he, oh my goodness.

Jennifer J. Hammond (22:26): He just sent me so many clients, which again, as you can probably tell, gets me so excited because I love helping someone who won, you know, all of those things don't come easy. You've gotta make, you've gotta apply to the, the estate programs, the city programs, the grants, all of that. You have to do the homework, but if you're willing to do the homework to me, what a fun thing, because now with one real estate transaction, just as a real estate agent, I have now changed his financial, his whole financial life for the rest of his life, with this one thing with just this one house. And it was something he was already doing, he was already paying, uh, you know, a rent. So you're either gonna pay rent to your land, you know, your landlord, or you're gonna pay your rent or your mortgage payment to the bank. So who do you wanna invest in yourself or your landlord? Who would you like to build wealth?

Daphné Vanessa (23:28): Wow. I've, I've heard this argument a lot, but I think the way that you explained it today is probably the most compelling because you've explained it as investing in yourself, you've showed us how we can use the no capital gains tax to literally pay off our student loans, pay off, pay for somebody's wedding, pay for literal change, financial trajectory, like you said, I'm inspired. I think that people need to know where to get in contact with you so that they can learn more because I know there is so much more that we didn't even touch on. We didn't have time to touch

Jennifer J. Hammond (24:04): On. I know I just realized, oh my gosh, we ran out of time. So yes. So my,

Daphné Vanessa (24:08): Are people gonna find you?

Jennifer J. Hammond (24:09): So, and I do, I do. I still teach classes, everything from the first time, even I was 25 years in the business. I still love teaching first time home buyers. And I love teaching brand new first time, um, real estate investors. Those are my two, I just absolutely love. And I have those classes, um, online for people, wherever they are, they can do it. Um, so you can just go to my website, Jennifer J hammond.com. So Jennifer J hammond.com and, um, and then all the classes are up there. Plus the, my podcast is up there, which I can't wait. I love having you as a guest. I can't wait to have you on again. Um, so feel free to go there, get anything you have. And I would love, you know, meeting up on the social media because, um, Facebook, we do lots of Facebook lives and Instagram lives always doing the upgrades on, um, like right now there's a new thing out about credit.

Jennifer J. Hammond (25:01): And what they're doing with our credit score is because of the pandemic. And there's a new thing called the resiliency score, which is some people are gonna use as part of your FICO. Some things, um, some, some companies won't use it, but some will, and it's really important to get that kind of stuff. So anyway, so we do those Facebook lives, um, every week so that people can get the information they need. I think it's so important and I want everyone to be empowered. So thank you so much for letting me share my story and my passion for helping others become financially free. And don't have those, those handcuffs, but go to college, enjoy the education, you know, just break free from those golden handcuffs.

Daphné Vanessa (25:41): Yes. Yes. Inspirational. Thank you so much, Jennifer. We loved having you on the student loan podcast. For more episode, everyone, everyone listen to this and write it down for more information about this episode, episode 68, please go to the student loan podcast.com/episode 68, where you will hear all about Jennifer's story. And of course in the show notes, you know, we got you all those links that she mentioned. We're gonna have them for you. Thank you so much, everyone.

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