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Emily Gregory
Hi everyone.
Cheryl Strayed
I'm Cheryl Strayed, author of Wild and Tiny Beautiful Things. I'm excited to share that I have a new podcast called Mind Over Mountain. In each episode, I interview athletes, adventurers, and adrenaline seekers to discuss the inner landscapes that informed and inspired their extraordinary feats so we too can better understand how to face our own seemingly insurmountable challenges. Listen to Mind Over Mountain every Thursday on the iHeartRadio app, Apple podcast or wherever you get your podcasts.
Eating While Broke Host
It's Financial Literacy Month and the podcast Eating While Broke is bringing real conversations about money, growth and building your future. This month, hear from top streamer Zoe Spencer and venture capitalist lakeisha Landrum Pierre as they share their journeys from starting out to leveling up.
Eating While Broke Guest or Host
There's an economic component to communities thriving. If there's not enough money and entrepreneurship happening in communities, they fail.
Eating While Broke Host
Listen to Eating While Broke from the Black Effect Podcast Network on the iHeartRadio app, Apple Podcasts or wherever you get your podcast.
Daniel Alarcon
I'm Daniel Alarcon and this is my friend. He's much more famous than I am.
John Green
I wouldn't go that far, but I'm John Green, co host of the podcast the Away End. With my old friend Daniel.
Daniel Alarcon
On our podcast the Away End, we'll share with you the magic of international football, all leading up to the 2026 World Cup. Together, we'll find out why, of all the unimportant things football, soccer is the most important.
John Green
Listen to the Away End with Daniel Alarcon and John green on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Ana Navarro
Welcome everyone to this week's episode of Bleep with Ana Navarro. This week I have a real treat for you all. I don't know about you guys, but I was so happy and so thrilled when I heard that the district in Florida representing Mar? A Lago that includes Mar A Lago and representing Donald Trump as a constituent had been flipped from Republican to Democratic hands. And I wanted to connect with the person who had been able to do that. I got her on the phone a few days ago and told her what I'm talking to you about. In this conversation we're having, I want to share with all of our listeners. So for you today, I have State Representative Emily Gregory from Florida. Are you a state representative yet are you, are you officially sworn in?
Emily Gregory
I am, I am official. In Florida, you become the representative at midnight election day. So I'm going to be sworn in next week, but I am officially a state representative.
Ana Navarro
Well, welcome. Thank you for being here. I told you on the phone, you've brought me hope because a lot of people ask, okay, you know, there's all of these no Kings protests, there's all of these things going on, but will it translate into anything? And I think you have demonstrated, you have shown by turning that seat that it's translating into people going into the voting booth and making a choice and making a difference. But before we get into talking about the election, I wanna talk about you. Cause I think for a lot us, this is the first time we, we get to hear from you, we get to see you. So can you tell me a little bit about you?
Emily Gregory
Sure, sure. So I'm, I live in Jupiter now and I'm from about 30 minutes north. I was raised in Stuart where my parents still live. And I have, you know, Florida was very different when I was growing up. We had a long history of Democratic governors. I went away to college and grad school. I studied health and got a master's in public health. Really fell in love with just the science and the data of it all. I went to work in D.C. for a number of years at the National Council on Aging in their center for Healthy Aging overseeing evidence based programming. And then I went to work for the state of Georgia in their Department of Behavioral Health where I oversaw evidence based programming for the most seriously acute diagnoses, I think schizophrenia or bipolar with psychoses. And then I went to, my husband was active duty army all this time. And we went to Fort Hood. We were expecting our first and he was deploying again. So I left the workforce, stayed home, had a really challenging year by myself in Texas. And the second year we, he was deploying again. We'd had our second child. So I went back to Stuart, my hometown, and I'd always seen over the years a group of moms running over the Suz Point Bridge. And I clocked it away over the years as that is a wonderful service or company or whatever it is. So I joined it. It was, it turned out it was a fitness franchise. I was a client for a little under a year in Stuart and then we moved to Jupiter where we now live. And I've owned and operated Fit for Mom Palm beach for seven plus years. We provide high quality postpartum fitness to new moms across Palm beach county and Why I decided to do a crazy thing like run for office is that I spoke to so many friends across the political spectrum as a small business owner in my personal life on the school advisory council at my children's elementary school. And I found that we were all in agreement on about 90% of issues and that what was being, what was happening in Tallahassee was not reflective of, of our priorities and really the centrist nature of my community. So I, after several years of thinking about it and observing where I thought I could have the greatest impact, you know, I thought about town council, county commission, state legislature, congress, and I really feel that what impacts my family and my neighbors lives the most on a day to day basis is what happens in the state house. And I didn't think we were getting the representation we deserved, so I just decided to do it.
Ana Navarro
So you, you had never run for anything before? You never run for, ran for student council, you never ran for class president in college?
Emily Gregory
I think I was the vice president of programming for the Pan Hellenic. Pan Hellenic Council in college, but no, I've never run for anything.
Ana Navarro
Okay, so run us through that though, a little bit. Right, because that means you didn't have experience on how to run a campaign, you know, you know, how to buy media. How. I mean, just. And I think there's a, there's a lot of people that may be listening who are unhappy with the way government is working, who are pissed as hell with the people and unsatisfied with the people representing them and who may have had or not have had a thought one day of, you know, I could do a better job, I should run for office. But. But things stop them from doing so. So, so, okay, so you, so you get this thought in your head, you go home and you tell your husband, I mean, how does this work? How does, how does somebody who's never run for office, who's a mom, a small business owner, a military wife, a health person, come home and say, hey honey, I think I'm gonna run for office.
Emily Gregory
Well, I would say it was a slow burn for a few years. Truthfully, many of my friends and family had told me that I should do this. And I always said, I don't. I don't know about that. That's. That sounds like a lot. And who would ever want that job? And how hard does that sound running for office? Um, and you know, I just sort of thought about it. It was really around 2020 and Black lives Matter and Covid that I really started to sort of tune back in. So in my 20s, I was very, very policy obsessed. Like, would leave C Span on, on the TV and my roommates would make fun of me. And then, you know, I. We were very busy. Andrew, my husband, was deploying. We had three small children, and politics had become so, so toxic. So for several years, I felt like, pretty leaned out. It felt really unrewarding to, to tune in, just to do the toxic nature of partisan politics. And then about five, six years ago, I feel like I woke back up and realized no one is coming to save us. We have to save ourselves. And I wanted to be strategic and wait till my family was in a place that I felt that we could make this sacrifice. And I have an incredibly supportive husband who has taken on a lot of childcare duties and has really been the primary caregiver for our family for the last six months. And of course, with his service in the army, his service always came first for 15 years. So this is us sort of transitioning into what maybe the next 15 years of our life could look like. Who knows? I mean, I'm, I'm one week into this new job.
Ana Navarro
But did it occur to you that, that you could actually win? And I, and I asked that because the seat that you won has been long held by Republicans. The guy who had the seat before you had won the seat by 19 points. Points. Donald Trump won that district by 11 points. So it's not like you were running in a purple district that could go one way or another. It's not that you, you know, you didn't have the demographic advantages there. So did you, did it actually occur to you I could win this thing?
Emily Gregory
I never thought I wasn't going to win until like 3pm on election day. We were nervous. The numbers were looking challenging, but I've believed it the whole time. I feel very embedded in this community and I feel like my voice is very representative of my neighbors and I think also just not being from the political machine. I saw the previous Democrat receive 41% and I thought, I don't know, you need like just 9% more. So it's not, it's not undoable.
Ana Navarro
Emily, 9% in politics is a lot.
Emily Gregory
Well, now that I've been doing it a little bit longer, I see that and I.
Ana Navarro
What did you win by?
Emily Gregory
2 and a half.
Ana Navarro
What was it about your campaign? What did you do that you think helped you win? What were you doing actually on the ground?
Emily Gregory
100%. It was the knocking on doors, I think a lot of times, as I've been observing other campaigns, people Sometimes want to skip the part where you do the work in anything in life, you can't skip the part where you do the work. You want to build your small business. If you want to grow, you know, grow in your corporate job and in a campaign that grassroots is absolutely how we won. We started with, you know, me and three friends as a volunteers and then we would hold lots of meet and greets and get a couple more volunteers at each one, get a couple more supporters financially. And it really just networked. It spidered out. So three or four people who were at an event of maybe 20 people would host their own and then I would meet their whole networks. And as I suspected, across the political spectrum, there was, you know, a lot of convergence on what needed to be solved. Property, insurance and healthcare and education. And it's all very reasonable positions that have state policy solutions. And there's a state legislature that hasn't focused on them for years and are far more focused on, you know, sort of attacking legislation against vulnerable communities and culture wars. And I don't see my neighbors asking for that. And that, that's, I mean, that all is what I heard from voters.
Ana Navarro
So you did it, you did it the old fashioned way. You, you put the sweat equity into, into and the, and the steps in, in order to, to win this campaign.
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Podcast Guest (The Steno Show)
I went and sat on the little ottoman in front of him and I said, hi, dad. And just when I said that, my mom comes out of the kitchen and she says, I have some cookies and milk. This is badass Convict. Just finished five years. I'm gonna have cookies and milk at mom.
Podcast Host (The Steno Show)
On the Steno show podcast, each episode invites you into a raw, unfiltered conversations about recovery, resilience and redemption. On a recent episode, I sit down with actor cultural icon Danny Trejo. Talk about addiction transformation and the power of second chances. The entire season two is now available to binge, featuring powerful conversations with the guests like T. Tiffany Adish, Johnny Knoxville and more.
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Eating While Broke Guest or Host
I feel like it was a little bit unbelievable until I really started making money.
Eating While Broke Host
It's financial literacy month and the podcast Eating While Broke is bringing real conversations about money, growth and building your future. This month hear from top streamer Zoe Spencer and venture capitalist lakeisha Landrum Pierre as they share their journeys from starting out to leveling up.
Eating While Broke Guest or Host
If I'm outside with my parents and they're seeing all these people come up to me for pictures, it's like, what today? Now, Obviously, it's like 100%. They believe everything, but at first it was just like, you gotta go get a real job. There's an economic component to communities thriving. If there's not enough money and entrepreneurship happening in communities, they fail. And what I mean by fail is they don't have money to pay for food. They cannot feed their kids. They do not have homes. Communities don't work unless there's money flowing through them.
Eating While Broke Host
Listen to Eating While Broke from the Black Effect Podcast Network on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast.
John Green
I'm John Green. You may know me as the author of the Fault in Our Stars, and now, I guess also as the co host of the Away End, the brand new world soccer podcast.
Daniel Alarcon
I'm Daniel Alarcon, a writer and journalist, and John and I have known each other since we were kids. My first World cup was Mexico 86. I was nine years old. I watched every game and I fell in love. On our new podcast, the Away End, we'll share with you the magic of international football, all leading up to the 2026 World cup for US Soccer.
John Green
Football is a story we've shared for over 30 years, since Daniel was the star player on our high school soccer team.
Daniel Alarcon
Very debatable.
John Green
And I was their most loyal and sometimes only fan. I love this game. I love its history, its hope, its heartbreak, and above all, its beauty.
Daniel Alarcon
Together we'll find out why of all the unimportant things football, soccer is the most important.
John Green
Listen to the Away End with Daniel Alarcon and John green on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Ana Navarro
Were you, were you prepared for the shock waves that your election would cause, for the national attention that your election would bring?
Emily Gregory
So, and I tried to fundraise off it. I mean, I really was making the case at events that this will create headlines. I could never have conceived how much media attention this state House race in coastal Palm beach county would receive. I mean, I think it's gotta be the most covered state House race maybe of all time. Um, so I did, I did expect, like some local, you know, coverage, but not the international, you know, attention it got for a couple weeks there.
Ana Navarro
And the reason that it's getting the headlines is because your district includes Mar A Lago. Donald Trump is now your constituent. And of course he has. So wait, before I ask you the next question. How does that feel to know you represent Donald Trump?
Emily Gregory
It doesn't feel all that different. Right. I'm focused on all 180,000 constituents. I mean, he is the president is the reason people have tuned into this race. But I think the takeaway is more of the grassroots message. And also I think about women taking, if they need to or want to, career pauses and then jumping back in and then anyone entering the political fray, you know, and if you want representation that looks more like normal neighbors, then normal neighbors have to run.
Ana Navarro
One of the things that Trump has been doing, not just when it comes to one election, but to every election, is he's been railing against mail in voting. He's been railing against absentee ballots. And of course, being the king of hypocrisy that he is, he voted by mail in ballot. His wife voted by mail in ballot. His son voted by mail in ballot. They're all your constituents and they all voted by mail in ballot. What is your message to people on election security and whether mail in ballots are secure?
Emily Gregory
Mail in ballots are absolutely safe and secure and a really important tool for people, all people, to include the president that are busy working or need a reason that they can't take off work on election day to go vote. So I support the president as well as every other Floridian and American to have the, the tool to vote by mail because it's a really important way so that, you know, our, our we have proper representation.
Ana Navarro
He says he needs to vote by mail because he's president. Well, I think every American should be treated equally under the law.
Emily Gregory
Exactly.
Ana Navarro
You said that when you spoke to your neighbors, you had a lot of convergence. If I asked you to describe yourself politically, how would you describe yourself in terms of ideology? Are you a progressive, are you a moderate? Or how do you describe yourself? Do any of those labels fit?
Emily Gregory
I would self describe as like a pragmatic, just looking for solutions, centrist often. But whatever the best solution is. And there are things that I think that we need some really bold policy solutions like a state catastrophic fund in which the state self insures against catastrophic loss for hurricanes. I think the insurance market is so unregulated right now and so disrupted with this, this risk that we need to take it off the backs of private insurers and try to regulate that market. So that is, you know, would be a bold policy decision. But it's an effort to regulate a market. So centrist, pragmatist, whatever anyone wants to call me, you.
Ana Navarro
So the airport you fly in and out of, Palm Beach Airport. PBI has just been renamed. Ron DeSantis, the governor of Florida just signed legislation turning it into the Donald J. Trump Airport. Frankly, I think we should have named a federal jail for him would be much more appropriate. But okay, it's got an airport now. How do your constituents feel about that?
Emily Gregory
I hear from my neighbors and new constituents that we need these affordability issues tackled. We need property insurance premiums to come way, way, way down. We need to fully fund our public schools. We need to, we need to expand affordable healthcare and come up with a solution now that the ACA tax credits have been taken away. What I never once heard at the doors is I would like my tax dollars to be used to rename things. Not once.
Ana Navarro
You're going to have to. This was a special election, which means you have to run again. In six months, you're running again in, in, in, in the midterms. And so November 2028, 2026, in six months, you're going to be up for election again. I am sure Republicans are going to throw everything and anything, including the kitchen sink at you and not trying to get you defeated because of the significance of this seat. What can people do to help you?
Emily Gregory
I anticipate everything you said is accurate. I do think we will need a arsenal to defeat the Republican. I think there this was a public embarrassment for them and that they will be very focused on taking the seat back. I know that we have the issues on our side, we have the momentum on our side, but anyone that wanted to engage and support emily gregoryforflorida.com would be very, very appreciative. And then phone banking and if you're local canvassing and we're just doing the same exact playbook. I have a, like a flow chart that I made on a flip chart that says canvas, phone, bank, fundraise, and then an arrow go to the top, just those three things. And I attribute that to how we were successful as we stayed very disciplined. There's a lot of noise in campaigns and the other side might, you know, try things and people want your attention and want you to do all kinds of things. But if you stay really, really laser focused on the issues and the voters and do those things, you know, you knock on the doors, you make the calls and you raise the dollars, that's how you win. And you have to stay really focused and run a really disciplined Campaign.
Ana Navarro
Give me, give me the website again because I'm going to go on and I'm going to contribute after this. What's the website again?
Emily Gregory
Emily Gregory for Florida, Everything spelled out okay.
Ana Navarro
And I'm going to come up and I'm going to, I'm going to drive to Palm beach and I'm going to go door to door with you. It sounds like an effective way to, to lose some pounds, which I badly need to do, particularly if it's during the summer.
Emily Gregory
I'll also tell you it's also like the most soul affirming thing to do. There were a lot of, there were some hard days in this campaign, both Minnesota deaths. And so I was out canvassing. I came home, my husband said there was another death in Minnesota, Alex Preddy. And I was just so uplifted by having talked to all these neighbors and then immediately felt deflated. And then the next day I had to go out and knock on doors again. And it really, it really helped me feel like I was being productive and doing my part to change the climate and change, you know, where we are as a country.
Ana Navarro
How many doors do you think you knocked on?
Emily Gregory
2,500, 3,000, something like that?
Ana Navarro
I always like to end with a little bit of optimism, with a note of optimism. I think so many of us are feeling deflated, to use your word. The tariffs, the war, the gasoline prices, the grocery prices. I mean, so many things that are just so stressful and distressful. So I want to ask you, Emily, as we say goodbye today, what is bringing you hope? What is bringing you hope?
Emily Gregory
Well, in this very unique time, I have received an outpouring of emails across the country, internationally from people saying this election has given me so much and that's the exact word they use, hope. I was feeling that everything was so dark and impossible to see the light. And if I can be a small part of shining a light on, you know, a way forward in a better Florida, a better future. I've always said, I truly believe that most of us want a fairer, kinder Florida that's more affordable and works for all of us. So that is what's bringing me hope. And I'm so thrilled to be the new state representative for District 87.
Ana Navarro
And you know, you said something at the beginning that I'm going to, that I want to circle back to and that I want to remind people of because you said that when you were growing up in Florida, Florida was reliably democratic for me as well. I've been in Florida 46 years. And I remember when I got to Florida, and for years after that, every state elected official was a Democrat. The governor, the senators, the congress, people in South Florida. And that changed. And it's a reminder that I think sometimes we give up on states. We give up on Texas. Oh, that's solidly red. We give up on Florida. Oh, that's solidly red. Or you take New York for granted. Oh, that's solidly blue. And I think it's a reminder that states change, priorities change, the way people vote change. And that when you work really hard to make a change, things change little by little. Seats change little by little. So thank you for being part of that change, because we definitely need balance in Florida as a long, long time Floridian. I want to be able to have home insurance. I want to be able to have bipartisan solutions to the very complex issues that are confronting our states. So thank you for having taken the plunge. Thank you for your courage and thank you for your hard work. I can't wait to see what you do in the state legislature and to get to know you more. And we're all going to be part of getting you reelected in nova.
Emily Gregory
Thank you so much. I'm so grateful to be here. And this was. This was wonderful.
Ana Navarro
So we just finished hearing from Emily Gregory, the spectacular woman who flipped the seat in the district in Florida where Donald Trump claims residency. And I think it's such a poignant reminder that being engaged, being involved, showing up, having courage and voting makes a difference. I want that to serve as a reminder that we are just a little over 200 days from the midterm elections. And there's things that all of us can be doing now. We can be checking our voter registration. We could be making sure that everybody in our circle of friends and our family is registered to vote. We can be volunteering in campaigns, we can be making donations. We can be doing all sorts of things, walking along with candidates and knocking on doors, making phone calls. There's tons of things we can all be doing. And so let's not sleep in our laurels. Let us get to work, because the midterms will be here sooner than any of us imagine. And we need to make a change and make a difference this November. Thank you so much for listening to BLEEP this week. I hope you will tune in next week. Please leave me your thoughts, your suggestions, your comments. Comments. I am reading all of them, trying to make this a better podcast. You can listen to BLEEP with Ana Navarro wherever you listen to your podcasts. And I hope to see you next week. Bleep with Ana Navarro is a Hyphenate Media Group production in partnership with iHeart's My Cultura podcast Network. For more of your favorite shows, visit the iHeartRadio app, Apple Podcasts or wherever
Eating While Broke Guest or Host
you get your podcasts. This is an iHeart podcast. Guaranteed Human.
Podcast: Bleep! with Ana Navarro
Host: Ana Navarro
Guest: Florida State Rep. Emily Gregory
Date: April 13, 2026
This episode features a groundbreaking conversation with Emily Gregory, the newly elected Democratic Florida State Representative who made headlines for flipping the district that includes Mar-a-Lago—and Donald Trump as her constituent—from Republican to Democrat. Ana Navarro dives deep into Gregory’s personal story, the grassroots campaign that led to her upset victory, the significance of her win, and what it means for the future of Florida and political engagement.
On grassroots campaigning:
“You can't skip the part where you do the work.”
—Emily Gregory (10:53)
On running as a nontraditional candidate:
“If you want representation that looks more like normal neighbors, then normal neighbors have to run.”
—Emily Gregory (17:30)
On representation and hope:
“If I can be a small part of shining a light on, you know, a way forward in a better Florida, a better future — I’ve always said, I truly believe that most of us want a fairer, kinder Florida that’s more affordable and works for all of us.”
—Emily Gregory (24:42)
On change and optimism:
“Sometimes we give up on states…And I think it’s a reminder that states change, priorities change, the way people vote change...when you work really hard to make a change, things change little by little.”
—Ana Navarro (25:29)
Campaign reality check:
“There’s a lot of noise in campaigns...But if you stay really, really laser focused on the issues and the voters and do those things...that’s how you win. And you have to stay really focused and run a really disciplined campaign.”
—Emily Gregory (21:49 – 22:47)
Both Ana Navarro and Emily Gregory leave listeners with a call to engagement, reminding everyone that “showing up, having courage, and voting makes a difference.” Gregory’s story is a case study in how everyday citizens can challenge the status quo, leveraging community-centered campaigning and optimism even in deeply polarized environments. As the midterms approach, the conversation closes with encouragement to get involved, remain hopeful, and believe in the power of local action.
For more information or to support Emily Gregory:
emilygregoryforflorida.com