Though Sally Bradshaw is most known for serving as Jeb Bush’s senior advisor during the 2016 presidential race, her accomplishments far exceed politics. The George Washington University graduate is the epitome of success having worked alongside political giants such as former president George H.W. Bush, completed consulting work for award-winning firms such as CoreMessage, and served as a member of the Florida State Board of Education. Additionally, Bradshaw is a sought-after public speaker and most recently, a successful bookstore owner.
Bradshaw is fluent in Floridian. The Mississippi native relocated to Florida to pursue opportunities in political campaigns. Upon doing so, she was immediately drawn to the state’s capital. “I love Tallahassee,” she states. Bradshaw is an adamant supporter of Florida State University, the city’s largest institution, and raves about its creative writing program. “There’s just so many talented writers in Tallahassee and through FSU […]. It’s the place to be in the creative writing world […].”
Though her impressive resume and 30 years of experience highlight her political influence and expertise, Bradshaw has a very clear passion for books and writing. In 2016, she opened the Midtown Reader, an independent bookstore located in Tallahassee, Florida. “Gosh, you know I’ve wanted to have a bookstore since I was a little girl.” she explains. “A place where people can agree to disagree in a civil fashion, and they can commit to continuing to learn and grow through content and programming, and through reading.”
Chris Cate: Welcome to the Fluent in Floridian podcast, featuring the Sunshine State’s brightest leaders. Talking about the issues most important to the people of Florida and it’s millions of weekly visitors. I’m your host Chris Cate and in this episode brought to you by SalterMitchellPR I’ve talked to Sally Bradshaw, a long time senior advisor to Jeb Bush. In our conversation, we’ll talk about her work in the White House and how that led to working with Jeb. We’ll also talk about her proudest accomplishment working for Jeb, and of course, about last year’s [00:00:30] presidential election. We’ll even talk about Midtown Reader, her new bookstore in Tallahassee, and about Florida’s growing author community. And you can hear it all right now.
Sally, thanks so much for being on this show. Most people know you as being a close advisor to Jeb Bush, but you actually worked for President H.W. Bush first. Can you tell me a little bit about how you got started into politics and landed a job working for the president?
Sally Bradshaw: Sure, yeah. I did work for the first President Bush and [00:01:00] gosh it was a long time ago. I had an internship in Washington the summer after my freshman year of college working on Capitol Hill, and as Washington stories go, you just end up meeting people up there and one opportunity leads to another opportunity leads to another opportunity, and I was blessed to work as an intern for Mary Matalin in the Fun for America’s Future, which was sort of the pre-cursor to all of these independent expenditure groups and it was the entity formed [00:01:30] prior to the ’88 presidential campaign for then Vice President Bush, and from there went into the campaign, and from there when he was elected went into the White House.
Chris Cate: Now, it’s easy to say that things kind of work out like that, but I’d assume you have to kind of actively seek out the right people. I mean, did you kind of pursue that place on that campaign, or how exactly did that come about?
Sally Bradshaw: So, I was really fortunate. I had a teacher, a government teacher, in high school who really [00:02:00] encouraged me to pursue an internship, which I did, and being from Mississippi I was blessed to know Haley Barbour, who was then the political director for President Reagan. So, from Capitol Hill, I went into an internship in the Reagan administration and knew that I wanted to go to work for then Vice President Bush and the campaign. So, one thing lead to another.
Chris Cate: Well, the White House has such world and historic significance. What was it like actually being there and working there? I mean, did you feel that kind of magnitude [00:02:30] of the office or is it just to busy to pay attention to that?
Sally Bradshaw: No, it was amazing and I was so young at the time. I think I was 24 years old, and it was just hard to believe that I was blessed to have a real job in the White House, and so I felt it every single day, the significance of being there. The work was very demanding and very rewarding, but I never lost sight of the fact that I was blessed to work in that environment.
Chris Cate: So, what was it that brought you to Florida?
Sally Bradshaw: [00:03:00] So, I really wanted to run political campaigns, and I knew that staying in the White House long term was probably not the best way to go about that. So, I began to look for opportunities at the state level and having grown up in Mississippi, my accent precluded work in states like New York or California, and it looked like Florida and Texas were my best bet to get into the campaign world. I accepted a job as the political director of the Republican of Florida when Dan Cool [00:03:30] was the party chair here in 1991 and I moved to Tallahassee.
Chris Cate: And, it wasn’t too much longer after that, that you started working with Jeb and ultimately helping with that first run when he first made that run for governor. What kind of a learning experience was that during that first attempt to be governor? Just for you and for him, what kind of learning experience was it?
Sally Bradshaw: It was a fantastic opportunity and experience just to get around the state and to meet so many new people, [00:04:00] and really to watch him and the type of campaign that he wanted to run, and the type of campaign he’s always run. I mean, I think so many lessons helped us down the road when he eventually was elected governor and beyond. He was a candidate who made it clear to our team that he would never sell his soul for a title or position, you know, commit to what you can deliver, care about the policy and how it impacts people. He was [00:04:30] an extremely honest candidate, sometimes to his own demise, but he made sure he could always look himself in the mirror when all was said and done and be proud of the positions he had taken and the fact that he advocated for big bold thinking in policy changes. So, I think we all learned a lot in that campaign.
Chris Cate: And, I think everybody knows that he would go on to win back to back terms as a governor and you’re his first Chief of Staff I believe. Is that right? Am I getting my history right?
Sally Bradshaw: That’s right, [00:05:00] yep that’s right.
Chris Cate: So, every candidate faces pressure to get all their campaign promises passed once they start, you know, finally get elected into the office that they’re running for. How hard is it to go from calling for change on a campaign trail to then actually being in that position and passing laws and budgets once you’re elected? ‘Cause there’s so much out of your hands, so how difficult is that?
Sally Bradshaw: Well, I think we all learned that governing should be different from campaigning, and the governor [00:05:30] really led in that regard. He made it very clear to our team, many of whom were political people who came in from that ’98 race, that we have to put aside past grudges, listen more, show humility, and work hard on the commitments that were made on the policy front. And, I think he led by example in that regard, so it was a terrific learning experience, and there were a lot of people who were ready for a change at that point after two terms [00:06:00] of a Democrat governor.
There was support for looking at some different issues and doing things in a different way, and he worked very hard at bringing people from both sides of the aisle together to enact policies that he felt were important in education, and tax reform, and really the budget was revamped and he made it clear that he was taking his commitments very seriously. But, he also made it clear that [00:06:30] governing was different from campaigning and I can remember specifically a group of us advocating for the appointment of someone to, I believe it was, a water management district position. He appointed the members of the water management districts, and this was someone who had worked very hard in the campaign and been very active. And, there was another person who had applied for the position who was extremely well qualified for the position and had not been an advocate for the governor when he ran, and not been supportive, and that’s [00:07:00] the person that he chose for that position. And, we were all astonished but he made it very clear to use, again, that governing was different from campaigning. It required leadership, that we would find the right post for others who were interested in serving, but he needed the best person to serve in this particular water management district appointment in south Florida, which was facing some real challenges.
And, I remember to this day, that lesson of needing to show humility and move on and work with people who had not always been supportive [00:07:30] to solve problems going forward.
Chris Cate: Yeah, I would think with, not just, you know, being elected but the fact that there was a party change in the governor’s office made it extra difficult and maybe required him to reach out more to the Democrats in that case. How long did it feel like it took you to get your legs underneath you to get comfortable in that position, just as an office in general, to feel like you’re really hitting the ground running? I mean, did it take [00:08:00] a few months or did you feel like right in the beginning you’re able to …
Sally Bradshaw: I don’t think anybody that is doing their job right feels that way. Being the governor or working for a governor of a state the size of Florida, is just remarkably demanding and whether there is a prison riot or a hurricane or a traffic jam or a budget crisis or a … it’s just, it’s Florida. So, everyday something’s changing and I think that’s why his humility [00:08:30] was so important. And, I think he also really felt the need to be connected to people outside of Tallahassee and he was really the first e-governor. He used email regularly to communicate with people outside the truck roots, as we like to refer to Tallahassee, and made sure that he understood how policies that he was advocating or opposing actually impacted real people. It was his way of keeping in touch.
But, I think if you have humility about a position you never feel like you’re completely [00:09:00] in command. You’re always learning, you’re always growing.
Chris Cate: Is there a particular accomplishment of Jeb’s as governor that you’re really proud to help play a role in getting done?
Sally Bradshaw: I’m actually really proud of the work he did on education and raising the bar, closing the achievement gap for minorities, and presenting additional opportunities to people outside of the system that had frankly become broken. At the time he was elected, education … [00:09:30] the numbers were really poor in terms of student performance in Florida, and he made it a priority, not just in the two years I was there as the chief of staff, but for his entire eight years and continues to advocate for that outside of office. So, I’m really proud of the work that was done on the education front.
Chris Cate: For candidates that are hitting the trail right now for next year’s governors race and they’re already out there campaigning. What advice would you give them about how to run a successful campaign?
Sally Bradshaw: Oh gosh, well we did not have [00:10:00] a recent successful campaign, at least on the presidential level. So, I’m not sure I’m the best person to give advice, but I do think Governor Bush’s lessons of being able to look yourself in the mirror, be honest, make sure you’re not over-committing, you know if you’re going to commit to something have confidence that you can deliver on that and don’t become disconnected from the people you intend to serve, show some humility, all matter in order [00:10:30] for us to have strong public servants who are on both sides of the aisle. I’m a little distressed that we seem to not be communicating and talking around each other, and one of the things back to the governor winning in 1998 that was so appreciated were Governor Chile’s staff and how they immediately embraced our team, came together to help us with the transition. His team was just so giving and supportive and encouraging, and they really understood that at the end of the day, [00:11:00] what mattered were not Republican governors or Democrat governors, but the people of Florida and the need to get things done. And, I hope that anyone seeking public office in a state this diverse would remember those lessons of leadership.
Chris Cate: A lot of people, I’m sure, want to be in a candidate’s inner circle, but I would assume too many people can actually cause problems. So, what is your take on how many people should actually be in a candidates inner circle that they really rely on?
Sally Bradshaw: I don’t know. I worked for an unusual, unorthodox [00:11:30] candidate in that regard, and people would always ask who was on Jeb Bush’s kitchen cabinet, and the only answer I knew to give was, that hundreds of people were on his kitchen cabinet. It depended on the topic. He really never lost sight of the people he was trying to serve, and he constantly wanted to grow and learn and bring new ideas to the table. And, I think that you have staff that play an important role on scheduling, on events, on policy, on budget, but at the same time it’s important to not [00:12:00] be walled off and not be in a bubble. I think he did a really good job of that.
And so, it depends on their style of leadership. He was not a high arsenical, top down driven leader. At least, with our staff and our teams. I can remember budget meetings where he went around the table and put plenty of our policy and budget team on the spot. They would tell him something about the budget and the way it was and he would then respond [00:12:30] by asking them how it should be, and they were a little unprepared for that because I’m not sure a lot of elected officials function that way. But again, I think it depends on a candidate and their style of leadership to answer that question.
Chris Cate: A long time passed between Jeb being governor and when he ultimately ran for president. Did he ever come close to running before he finally made that run?
Sally Bradshaw: Oh gosh, honestly I don’t know. I mean, I know that people approached and I know that people encouraged him, but I think [00:13:00] he had to be in the right place mentally to make that commitment. He’s not someone who does anything halfway, and I think he had to make sure that his family was supportive and ready for what a grueling challenge a presidential campaign presents and that financially he was in a position to take time off and commit 100% of his effort to the campaign. And so, my sense is that he had not been close before about [00:13:30] doing that, although I know many people had encouraged him prior to the 2016 cycle.
Chris Cate: I know hindsight is 20/20 and everything about last years election was really unusual, but is there anything that you think Jeb could have done differently to defeat Trump in the primary?
Sally Bradshaw: I think every Republican who ran against Donald Trump is probably, you know, discussed, buried, and exhumed that dead horse. And, I think it’s very difficult what could have been [00:14:00] done differently. I don’t know that Jeb would have run a different type of campaign. I think he made it very clear from the beginning there are places he would not go. There are positions he would not take. He intended to be true to his beliefs and true to issues that mattered to him, and the primary climate on the Republican side was really unlike any that we’ve ever seen, at least in recent history. So, I’m not sure … he’s just [00:14:30] not the kind of guy who’s going to say one thing and then do another, and to some extent I guess some people could have argued that would have helped, but he would have been miserable doing it and he wouldn’t have been honest, and that’s not the type of campaign he was going to run.
There are always a million things we could have done better I’m sure. There’s not question about that, but in terms of taking different positions on issues for example, or changing his position on immigration, or many other issues I don’t think he would have done it.
Chris Cate: This [00:15:00] will be my last Jeb question, but is there a scenario where you ever see him running for office again, whether that’s for president or anything else?
Sally Bradshaw: Oh gosh, I think he would probably never say never, and he’s certainly young enough to continue to run for public office, but my sense is right now he’s really pleased to be back working with his son doing a lot of travel, doing some public speaking, and continuing to advocate for education reforms at the state level.
Chris Cate: You made some headlines last year by leaving the Republican party. Is [00:15:30] there anything that conservatives can do to win you back, and people like you who aren’t happy with how things are playing out right now within the party?
Sally Bradshaw: Gosh, you know, I am a conservative, not a registered Republican now. I’m a no-party affiliate, which is essentially an independent in Florida. But, I’ve never stopped being a conservative, and I hope that the Republican party will learn to be a little more inclusive. And, to look at certain issues like immigration differently. Until that happens, [00:16:00] I don’t think I would feel comfortable in the party. I’m sort of a voter without a home right now. It’s just very difficult for me to be in a position where the de facto leader of the party had been so controversial and had done some things I found reprehensible. So, I think the party would have to significantly change its approach on a number of issues for me to go back.
Chris Cate: If Trump called you and asked for advice, you know whether he would take it or not [00:16:30] is another story, but what would tell him if he asked you for advice?
Sally Bradshaw: Well, he wouldn’t call me and he would not ask for my advice, that’s for sure. You know, it’s too early to tell what the impact of President Trump will be on the nation or on Florida. I hope that he and his team will learn from some of their mistakes early on, and I hope that people’s concerns in Florida will empower them to become more involved in the process. I think winning means nothing if you don’t move the needle in a positive direction, [00:17:00] and so as an American I respect the office of the president and I hope that any president would have humility, learn from their mistakes, and try to find positive ways to bring the nation back together.
Chris Cate: We kind of joked before the interview started that owning a bookstore is almost like a storybook ending you know in a movie, and now you own a bookstore and I don’t think it’s an ending for you by any means but, you know, what was it about being here full time in Tallahassee and owning a bookstore that really [00:17:30] made you want to do that?
Sally Bradshaw: Gosh, you know I’ve wanted to have a bookstore since I was a little girl. I grew up in the Mississippi Delta in a really small town right on the river, but we had a thriving independent bookstore and great public library system, and I loved to read and if I had not been distracted early on by the political bug I probably would have become a librarian. You know, would have pursued something like that, library science. But, this seems like the right time because I think independent bookstores can [00:18:00] provide third spaces for lack of a better description. A place where people can agree to disagree in a civil fashion, and they can commit to continuing to learn and grow through content and programming, and through reading. And so, it’s been great fun to do it.
I love Tallahassee. I’ve raised a family here and the community does seem to be embracing the concept of an independent bookstore. We have a terrific used bookstore here with some out of print books. We have a great comic bookstore, but we’re the first [00:18:30] general subject indie bookstore in many, many years in Tallahassee and we’ve been blessed with the support of the FSU creative writing program, and many other organizations who want to see us succeed. So, we’re really enjoying doing it.
Chris Cate: Yeah, no I love having you here. I was super excited when I heard that you were going to be opening …
Sally Bradshaw: Oh thanks.
Chris Cate: It really looks great. I have four last questions …
Sally Bradshaw: Yeah.
Chris Cate: … that I ask every guest. The first one is, who is a Florida leader you admire? I may be able guess who you might say [00:19:00] there, but who is a Florida leader you admire, and it can be someone from Florida history or someone still active in their work.
Sally Bradshaw: Gosh, well oddly enough, not a political figure necessarily right now. I have really been inspired by people I’ve met through this effort of the Midtown Reader. Most recently, Meg Baldwin, who’s an attorney. Meg runs the refuge house here, which you’re probably familiar with, Chris. It’s the largest women and children’s shelter in the state of Florida, and she’s terrifically [00:19:30] engaged and active in the community, super smart. She could be anywhere doing anything she wants to do, but she’s right here moving the needle in Tallahassee and I’m really respecting people who committed to changing things locally because I think I’m like Washington, which seems to be fairly dysfunctional right now. The place where we can get things done is Tallahassee and locally.
And recently Ann Kimbrough, who is the Dean of the Journalism School at FAMU, [00:20:00] was in our store. And, she’s remarkable as well. She started this entire black television news channel, which FAMU is sponsoring. And, she’s another one who’s engaged and involved in our community and is really committed to change here at home, and so I’m really looking to local leaders to make a difference for us.
Chris Cate: Yeah, thank you for mentioning those. They both sound like pretty awesome people.
Sally Bradshaw: They are.
Chris Cate: The next question I have and then this final four, is [00:20:30] what is your favorite Florida location to visit, and that can be a city, a restaurant, a beach, wherever you like, but what’s a favorite Florida location for you to visit?
Sally Bradshaw: Gosh, I like all different parts of Florida and all different places. I love the old Florida, close to us, sort of the forgotten cost area. Apalachicola, Saint Marks, Saint George, Wakulla Springs, that area. There’s not much of old Florida left, and we’re really lucky to have those areas so close to [00:21:00] us in Tallahassee.
Chris Cate: Do you have a favorite Florida sports team?
Sally Bradshaw: Is this gonna be bad if I say no? You know, I didn’t go to school in Florida so I guess to have to support the Seminoles being in Tallahassee, but I went out of state to schools that did not really have sports teams. I have a favorite Florida sports figure. I use to play a lot of tennis in high school and out of college, and I loved Chris Evert. [00:21:30] I grew up watching Chris Evert. I just thought she was a terrific athlete and showed super grace under pressure and she never threw her racket. I always admired that. I think she’s from South Florida somewhere. She’s probably my favorite Florida athlete.
Chris Cate: Yeah, Florida has got some really awesome tennis players that probably don’t get the…
Sally Bradshaw: They do.
Chris Cate: I know that people always make that Florida connection but there’s some awesome tennis players here.
Sally Bradshaw: They do.
Chris Cate: Last question I have is, what Florida person, place, or thing deserves more positive attention?
Sally Bradshaw: [00:22:00] I think I would have to say the Florida State FSU creative writing program, which is a top five masters in creative writing program nationally. A lot of people don’t know that, and to be honest I did not know it until I opened the bookstore and got involved with that program. There are so many starts, so much talent at FSU right now in the creative writing department. A Pulitzer winner by Butler, a national book award winner, Bob Schacochis. [00:22:30] Diane Roberts, who’s a commentator for public radio. Robby Howard who was recruited down from Atlanta. There’s just so many talented writers in Tallahassee and through FSU, and some young writers like [inaudible 00:22:45] and others. It’s the place to be in the creative writing world and I think a lot of people are completely unaware that we have such a strong program here, a strong group of writers, but the good news is they are frequently in and out of the [00:23:00] Midtown Reader. So, if you haven’t met them and you want to meet them or listen to them or pick up a copy of one of their books, we can cover that for you.
Chris Cate: Great, perfect. Well, thank you sharing that and thank you for bringing the Midtown Reader to us to meet those folks and all the people that come in and out of that store and thank you so much for taking the time to be on the show.
Sally Bradshaw: Yeah, thank you guys, Chris. Thanks for having me.
Chris Cate: Thanks for listening to the Fluent in Floridian podcast. If you aren’t subscribed to the podcast yet, I hope you’ll look us up and subscribe [00:23:30] to the show on your favorite podcast app, like Apple Podcast, Stitcher, or Google Play Music. If you leave a review, that would be great too. Thanks to my team at SalterMitchellPR for making this podcast possible. If you need help telling your Florida story, we’ve got you covered. We offer issues management, crisis communications, social media, advocacy, and media relations assistance. We also have our own in-house creative and research teams. Look us up at saltermitchellpr.com, for more information. [00:24:00] You can also find more information about the Fluent in Floridian podcast at fluentinfloridian.com. Have a great day.