Episode 019

St Pete X features business and civic leaders in St. Petersburg Florida who share their insight, expertise and love of our special city. An initiative of the St. Petersburg Group, St Pete X strives to connect and elevate the city by sharing the voices of its citizens, and to bring awareness to the opportunities offered by the great St. Petersburg renaissance.


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10/26/2017 | Episode 019 | 39:09

Craig Sher, Sembler Group

Craig Sher talks heroics in civic and business life, keeping a nuclear bomb in your back pocket, and St. Pete's economic future.

On this episode of SPx, Joe and Ashley take another stab at co-hosting, as they welcome the very spirited Craig Sher, Executive Chairman of the Sembler Company. In this multi-faceted conversation, Sher talks proverbial "nuclear bombing" as a life philosophy and the importance of heroic ventures in business and civic life. Sher played an integral part in the development of downtown St. Petersburg and shares, from that vantage point, his insight on economic development in St. Pete. A well-known fundraiser and booster of the Democratic Party, Sher also opens up about his thoughts on the 2016 presidential election and the future of party politics.

Key Insights

  • Nuclear Bombs: Sher's life philosophy revolves around being a "nuclear bomb. He says, "Everybody looks at life as trying to continue on what exists. I like to look at life of looking at something, trying to blow it up and reconfiguring it."
  • One of Sher's major influences was Charles Rutenberg, a developer of Countryside and a major architect of the Jewish community. He taught Sher, "that there are 100 ways to skin a cat. Look at all of them and pick one, and don't be afraid to fail."
  • Sher describes Pinellas' economic development as "parochial" meaning that Pinellas is broken into about 25 different organizations, all working toward the same goal. "everyone creates a fiefdom, everyone has an executive director, everyone has a budget, and it’s just a waste of resources. And one of my great things in life is trying to combine entities and agencies to reduce overhead, so you have more money to do what you’re trying to do."
  • A major roadblock for St. Pete/ Tampa Bay's development has been the lack of transportation infrastructure here. As a major metro area, Sher says, we are one of the few that does not even have a "minimally adequate" system.
  • Future transit: Driverless cars? Rideshares? Metro lines? Sher doesn't know the answer, but he believes that we need to be looking ahead and planning our city to attract millennials who are less likely to want to own a car.
  • Education: Sher is highly involved in the Pinellas Education Foundation. This nationally renowned organization works with Pinellas County Schools to make sure students are ready to go into a career, trade school, or college following high school.
  • Public/private partnership: Despite best efforts on both sides, Sher believes that neither public nor private sectors can make economic development happen on their own. Even Jeff Vinik, one of Tampa's most influential citizens, needs public involvement and infrastructure to make his ideas happen.
  • Amazon: Sher is highly skeptical of any HQ2 moving to Tampa Bay - he says this is largely an education problem, "our universities are not generating the kinds of people in any mass to work in world class organizations."
  • On the redevelopment of the Trop site: "I think this could be the single greatest thing that happened in the next century in this area, because we have that blank canvas I talked about before, where creative people in a public-private partnership can do extraordinary things and we can argue about what should be there, but it needs to be heroic, extraordinary… It may be 20 years before we turn a blade of dirt, but it has to be the right thing and you reach for the stars."
  • Sher often talks about being "heroic" in business and community ventures. He uses the example of All Children's Hospital reaching out to John's Hopkins to create a partnership. He says, "sometimes when you reach high you get a big fish."
  • Trop redevelopment: On what the site might look like, "create an environment with ten or 20,000 jobs, and maybe create one of the greatest K to 12 schools, that all the people that work there wanna send their kid there, and really do top world class education, business environment."
  • On leadership qualities that help build a city: Leaders must, "number one, feel it’s their obligation to do that for whatever, for sense of self, for sense of community, for their family. Second is you want people in the sports analogy who want the ball."
  • Frustrations with non-profit collaboration: "Because life is full of limited resources, whether it’s leadership or capital, we can’t squander that person’s capital. So, my idea forward is try to collaborate with as many folks as you can and try to get on that same page, change minds."
  • On Congressman Bill Young, "he brought billions of dollars to this area, whether it’s defense and bridges and roads and programs… That was extraordinarily important. We wouldn’t be nearly the county we were without him."
  • On objectivity vs. subjectivity: "I view myself as a passionate advocate for a variety of things. It may not be popular, I don’t poll test my positions, but you’ve got to be an advocate, otherwise nothing will ever get done. If everyone was objective and neutral, we would just live in this ongoing highway going to nowhere."
  • On deal-making: "my personal favorite technique in making a deal, and it applies to everything in life, whether it’s a relationship with a spouse or whatever, is let’s figure out what we’re gonna agree on. "
  • On Trump & nuclear bombs: "people were ready for a change, and they went through Obama hoping change, and by and large for a lot of people it wasn’t what they wanted, so they’re ready for change again. History will judge whether this is a change that they wanted, but it’s okay, again, to blow it up."
  • Shout-outs: Beth Houghton, St. Pete Free Clinic, and Tom James, philanthropist and Emeritus Chair of the Board for Raymond James.

"There are 100 ways to skin a cat. Look at all of them and pick one, and don't be afraid to fail...Failure is just a beginning of something, and I keep at it."

Tampa Bay Lightning head coach Barry Melrose press conference with Oren Koules, Len Barrie and Craig Sher at the St. Pete Times Forum in St. Petersburg, Florida June 24, 2008. TAMPA BAY LIGHTNING Photo/Scott Audette

"I view myself as a passionate advocate for a variety of things. It may not be popular, I don’t poll test my positions, but you’ve got to be an advocate, otherwise nothing will ever get done."

Table of Contents

(0:00 – 0:46) Introduction

(0:46 – 4:36) People as Nuclear Bombs

(4:36 – 6:55) Solutions to Public Transportation Issues

(6:55 – 10:53) Thoughts on Education

(10:53 – 15:46) Which Sector is Leading, Private or Public?

(15:46 – 17:29) Revitalizing the Tropicana Field Area

(17:29 – 19:34) St. Pete Today

(19:34 – 22:25) Leadership Qualities

(22:25 – 24:49) The Non-profit World

(24:49 – 26:50) Business Landscape

(26:50 – 28:10) Local Politics

(28:10 – 32:44) Objectivity versus Subjectivity and Polarization

(32:44 – 37:12) Trump

(37:12 – 38:31) Shout-outs

(38:31 – 39:11) Conclusion

Full Transcript:

Craig: Excuse me.

Ashley: You just sent me a decline.

Craig: Okay. I’m not here.

Ashley: I have a little… sorry, are we recording?

Joe: Yeah, we’re on.

Ashley: Okay.

Joe: We’re not here with Craig Sher from Sembler.

Craig: That’s right.

Ashley: Who’s that?

Craig: It’s great not to be here.

Joe: And we are not happy to have him here, thank you.

Ashley: Welcome!

Joe: This is the first time any of us have met. We talked about nuclear bombs and people as nuclear bombs, not the real nuclear bombs, what is one’s life philosophy and where do you have to play to be a nuclear bomb, what do I have to do to become a nuclear bomb?

Craig: I think you have to have confidence that what you say can be defended. Everybody looks at life as trying to continue on what exists. I like to look at life as looking at something, trying to blow it up and reconfiguring it. And it may come back to what it currently exists, but it may look differently. For example, a piece of land. I’ve been a real state developer all my life, I view a piece of land as just a blank canvas. Give it to 100 artists, they paint 100 different pictures. And so that’s kind of the way I look at everything, is if you could start over, what would it look like?

Ashley: What influences, or do you have any early influences in your life that you think that you credit to shaping…

Craig: Sure.

Ashley: …the nuclear bomb that you are today?

Craig: I had four kinds of major influences in my life. I will pick one, my first boss in Florida was a gentleman by the name of Charles Rutenberg. He was known for many things, but primarily he was the developer of Countryside up in Clearwater and the founder of U.S. Home Corporation and built communities. And he was also the architect of the Jewish community here and put together a lot of the social service agencies and all that. And he taught me that there are 100 ways to skin a cat and look at all of them and pick one, and not be afraid to fail. And so, I guess I lived my life not being afraid to fail. Failure is just a beginning of something, and I keep at it.

Joe: And I think there are a lot of different ways to get there, and we were talking a little bit earlier about one of the problems we have in the area is that there’s a lot of people doing a lot of different ways to get there. And at some point, we need to get some economies and get some power by combining some of these efforts. There’s some specific areas where you think that we certainly need that?

Craig: Well, I think in terms of economic development we’re still a bit parochial. Unfortunately, I think Pinellas County has 23 municipalities. Hillsborough County has two or three, and that causes us some disfunction. I was recalling, when I was President of the Chamber of Commerce, I think there were 20 different chambers of commerce in Pinellas County. And that’s a problem, everyone creates a fiefdom, everyone has an executive director, everyone has a budget, and it’s just a waste of resources. And one of my great things in life is trying to combine entities and agencies to reduce overhead, so you have more money to do what you’re trying to do. So, I think one of them is in economic development in the region, we have the Tampa Bay partnership and we have different chambers of commerce and economic development agencies, cities, sub-cities, and private groups, all trying to do the same thing, is to attract business to the area, and more importantly to grow existing businesses. And everybody is looking to the same couple of dozen companies to write checks to all the organizations, and quite frankly I know most of these folks, and they’re tired of it. I think they’d rather see most of them rolled up into one maybe overriding entity to work on. And I think that was why the Tampa Bay partnership was originally founded many years ago, and a few other organizations that say, ‘Let’s forget about all the parochial…’

Joe: And it seemed to be working to some extent, and they changed focus at some point, right?

Craig: Well, they did, they also suffered budgetary issues and they had a change in executive leadership. And they determined, and I don’t think it was necessarily wrong, they picked one issue and really tried to drive it home, and that was regional transportation. One of my big pet peeves, I think we’re the only metro, or perhaps with Detroit of the top 30 metros in the United States that doesn’t have even minimally adequate public transportation. And I think what they’re saying, guys like Jeff Vinik in Tampa and others, number one objection to moving a great business here is the lack of public transportation. Millennials and others just don’t want to own a car, or they don’t want to use a car on a regular basis, and there are very few options. I think that… I don’t know if this is true, maybe it’s my theory that Tampa Airport is the only airport that I know of in the world you can’t leave with public transportation. Think about that. I don’t think you can take a bus, you can’t take a subway, you can’t take anything out of there. Any other airport that I’ve ever been to, you can take something, and that’s a problem. And we’re not adequately addressing that, because in large part of the parochialism.

Joe: And we had Jeff Brandes on, and he’s very passionate, he’s been working on that subject for a long time, and he sees the biggest challenges as what they call the last five miles, or the last mile, right? The way we’re set up, the infrastructure, especially if it’s light rail or whatever drops you off, behind the Times building or even up further away from downtown than that, and you’re expected to walk three, to five, to eight blocks. And that’s why he, instead of getting behind big mass transit transportation on a large scale, he got behind driverless cars which could then go through a neighborhood on a computerized schedule and pick people up at whatever it is the most efficient, around the time to take them work. Any thoughts on that?

Craig: I think he’s on the right track. I’m not a transportation expert, but I do believe you gotta think a generation ahead, because it takes so long to plan and fund and build these things, they could be obsolete. So, I think of transportation as a subway, or a rail like in Chicago, or New York or whatever. I’ve got a good friend, Derek LaClair, you might know, he thinks of it as gondolas, which are really cool. I don’t know if you heard his theory on that, but that’s pretty interesting. So, you have to think a generation ahead, because by the time we fund these things and get them going, the time is now. I happen to think he’s on the right track on driverless cars. Just an interesting anecdote, I’m on a board of a company in Pennsylvania, and one of the things that they do is build parking garages, and the parking garage industry is going in the tank. ‘And why is that?’ I asked. And they said, ‘Because it’s expensive to build parking garages, can’t get a return on investment, and cities now, instead of wanting you to drive to town, they don’t want you to drive to town.’ I don’t know if you’ve been to London, but they charge you an enormous amount of money to drive your car into London. I know New York is examining that, and I know lots of cities are looking at their zoning and saying, ‘Two cars per every condo or apartment, we only want you to do one, or maybe a half of car.’ And so, these parking garage companies are exploring ways of building parking garage differently, so you could convert them to other uses. So, they’re thinking ahead to say, ‘Maybe people aren’t gonna be using these garages,’ and further they’re talking about building parking garages for driverless cars. And you say, ‘Well, what does that mean?’ Well, they’re thinking of building the space as 30% narrower. Because, why? I didn’t know, he said, ‘You don’t open your car when you have a driverless car, you would drive your passengers somewhere else, they go in there, you don’t have anyone to get out of the car.’ So, you have to think ahead, a couple of generations ahead, long awaited answer.

Joe: Yeah. Ironically, I’m on the board of a parking lot resurfacing company based out of Tampa, they’re a national company, and we’ve been facing some of the same challenges, and so I’ve had the exact same experience. We haven’t talked as far into it, because they’re more in the post-construction phase of it, but some of the same concerns we’ve talked about as well.

Ashley: So, is it safe to assume that next on your list as it pertains to economic development, some of our issues would be education, or something in that realm?

Craig: Yeah. I’ve been very involved in the Pinellas Education Foundation, which is just a fabulous foundation. It was ranked the last several years the number one education foundation in the United States. We’re the business partner for the Pinellas County School District. And we do a ton of innovative things. The mission of the organization is to make sure everyone graduates, either ready for college, ready for a job or ready for  career ed, it’s extraordinarily important. We’re also the biggest providers of—we used to call them ‘doorway scholarships’– for disadvantaged kids to go to college.

Ashley: Rick Baker was on our show, I think he was eluding to that partnership, or at least a proposed partnership around apprenticeship.

Craig: Yeah, so now we have a lot of different initiatives. We’re thinking about, again, kind of the nuclear bomb theory, as what’s the next step? So, one of the things we’re thinking about, at least I’m thinking about, is getting public school kids to be able to compete to get in the college. We think about good grades and all that, but there’s an art form to filling out your college application, doing your essays and taking advantage of all the things, like kids maybe in private school, perhaps tutors to do essays and things like that. The second thing we could do is help all these kids who aren’t going to college get jobs. Job fairs, resume building, learn how to interview. Because I think a lot of times education analysis stops at graduation. Well, I think it’s important to follow these kids through, I know there’s a trend in university education to track these kids for the next five or ten years. Are they producing graduates that can get jobs? So, again, it’s education-related economic development, because if we can keep our best and brightest in this area, we’re gonna do a lot better.

Ashley: I think he eluded to exposure to trade, so essentially selecting a group. I don’t know what the criteria would be for involvement, but essentially providing transportation to get them on site, hands-on experience, and even set them up to have a career, irrespective of whether or not they go to a four-year university.

Craig: A few anecdotes. We have to get away from every parent wanting their kids to graduate college and be an English major. And when I was President of the Chamber a decade or so ago, I remember we had 120 vacant auto-mechanic jobs in the county. The dealers were willing to give the kids the tools, which is a couple of thousand bucks, but nobody wanted to go to auto-mechanic school, even though the beginning salary was $60,000 and the average salary I think was 80 or 90,000. Second anecdote is my plumber, I had this wonderful plumber for 30 years, paid him a lot of money. He can’t find people to work for him, and he’ll start them out with no experience with $60,000 a year.

Joe: Wow.

Craig: So, I think we’re gonna have to reorient back to when I was a kid, when we went to high school in ninth grade, about a third of my middle school graduates went off to trade school. You don’t see that as much anymore, I think they view P-Tech and some other trade educational organizations as like going to jail.  And in the meanwhile, I think that some of the best jobs in America are gonna be trade-related. So, I agree with Rick, anything we can do to encourage that, facilitate it and make it happen is a good thing to do.

Joe: And I also think one of the ways that’s going to happen is by expanding the definition of what trades are. Because I think the standard, like you said, the English major four-year degree, the ROI on that, it’s just disintegrating. And you have major thought leaders, like Peter Thiel who are paying people not to go to school, you’ve got Seth Godin who’s doing the altMBA program, and the people that are getting the highest paid jobs, a lot of them, the database administrators and the tech people, and they’re starting these companies don’t need to do that anymore. So, those careers and those kinds of jobs can be right back into the trade schools, then it just… rising tide lifts our boats.

Craig: I’m not really popular in some of my circles, but I think you need to graduate every level, starting in high school, qualified to do something. And so, you need to graduate high school to qualify to do something, whether it’s a trade or going to college. But it’s incredible, and my children have survived this, graduating college and gone to great colleges and all that and qualify to do something. But when you think about the people, your relatives, whatever, a lot of times they graduate four-year schools and have no idea what they wanna do, and are basically unqualified to do that. So, I think you ought to be able to at least graduate college qualified for a job or a skill. Not always a popular thought.

Joe: We talked about Vinik, and this is backtracking a little bit to the economic development. So, Vinik shows a model for a private group doing the same thing that the small splintered groups are trying to do in St. Pete. Which do you feel better about? Would you like to roll up in public, or do you think that a strong, private leader is the best way forward?

Craig: Both, because you work together. I’ll give you an example, a subject I’m very passionate about as the Rays. I think the Rays are vitally important to stay in the Tampa Bay area. Personally, it makes no difference to me where they are, but you noticed I think a day or two ago they announced, or at least one guy announced the site, Commissioner Hagen, unbeknownst to a lot of his brethren a potential site for the Rays. And it happened to be a very interesting site, I‘m not here to… It’s probably as good as any, but without the private sector and public sector working together, it’s going nowhere, whether it’s finance, design, access, parking utilities, all of that. So, Jeff Vinik, who I admire greatly, can’t do it without public participation in terms of infrastructure, getting a med school, whatever else the public can provide. And certainly, and I don’t know that a lot of our elected officials understand that the public can’t do it without the private sector. A lot of times the public sector thinks they can do it as well or better than the private sector. In rare cases does that happen.

Joe: Alright. It’s gonna be an interesting time, especially that we’re making a big effort to do economic development, we have a new St. Pete EDC—again, it’s another one, but I think they’re doing some good work. And with the Rays potentially leaving, that presents a PR challenge as we court Amazon and other big companies, but I think, and I think you will agree with this, there is a silver lining to that, because you have in the Rays… because you’re not sure that they’re gonna stay, that means it’s a borderline situation. But if they happen to move to Tampa, what’s left behind is a really awesome situation potentially, right? And that’s because it is such a rare site, and because getting – if not Amazon, which I think the chances are pretty slim – but a company not too many ranks down from them to come in and call this place home and take advantage of that, that could be a really powerful thing for this city.

Craig: There are lots of areas related to that. First of all, Amazon is not coming here. If I was Amazon, it wouldn’t be on my top 50 lists right now for the kinds of things they want. So, we can think about that, but I heard there were 268 applications, my sense is there are a lot of interesting places that will be rating ahead of us. Hopefully in 20 or 30, 40 years we can compete, but it’s not really…

Joe: Twenty-three of those, every Pinellas chamber put an application for Amazon, really.

Craig: Yeah. It’s not likely that we will be considered on this short list.

Ashley: Do you have any opinions? Are you thinking Atlanta or Toronto?

Craig: I don’t know exactly, but my criteria knowing what I know about them is they wanna be near where there’s a really qualified workforce being generated constantly, in other words great universities. It’s certainly gonna be one with great public transportation, certainly one with affordable housing in a sense of not everyone can afford a million-dollar house, great airport… And we have a few of those things, but one of the common complaints about this area is our universities are not generating the kinds of people in any mass to work in world class organizations, so I think that’s gonna be one of the challenges as time goes on. You go into research triangle, you go to D.C. or you go to Boston… I’m not as conversed in Toronto about their education, but there’s some wonderful educational centers that have a numbers of public and private colleges, so I think they have heads up over us. The only thing we have equal of anyone else is probably our airport. Can’t get there by public transportation, but that’s a whole another story. In terms of the Rays, just really quickly, it’s not a PR black mark if they stay in the region, it is I think if they leave the region. I come from Minneapolis, when I was a kid the Minnesota Twins played in Bloomington. You probably don’t know where Bloomington is, it’s a suburb. And now they play in Minneapolis. When I was a kid the hockey team played in Bloomington, they play now in St. Paul. Nobody knows that or cares as long as it’s in the region, we are the Tampa Bay Rays. I think it’s a little bit of a black mark if they move the region, we won’t know that for ten years. But I’m extraordinarily excited about the 85 acres of the Trop. I think this could be the single greatest thing to happen in the next century in this area, because we have that blank canvas I talked about before, where creative people in a public-private partnership can do extraordinary things and we can argue about what should be there, but it needs to be heroic, extraordinary… It may be 20 years before we turn a blade of dirt, but it has to be the right thing and you reach for the stars. I’ll give you a minor example, I’ve been on the board of All Children’s Hospital for 14 years. We wanted to explore our options, shall we say, in having an association with a university. And again, I’ll mention a great name, Derek LaClair said, ‘If you’re gonna pick someone go for the greatest.’ Number one hospital in the United States for the last 20 years, or 19, last 20 years, Johns’ Hopkins. They wouldn’t return our phone call for a couple of years, finally they did and making a really long story short, we’re now Johns’ Hopkins All Children’s Hospital part of the greatest hospital group in the United States. And sometimes when you reach high you get a big fish. But we can do that over there, we have the ability to be patient, because the land is owned, free and clear, there’s no interest collected, there’s no taxes to be paid on it. It’s really so exciting when you’re in in the development business, or in the community business. To me, we ought to be talking about that constantly. I get frustrated sometimes when keeping that top of mind.

Ashley: So, take us into the creative’s mind and visualize for our listeners what that could look like for you.

Craig: So, about almost a year ago I invited 20 of the top architects and developers to come to City Hall from around the state, and they did at their own expense, and met with the consultants that the city has hired. And I can’t remember the name of the consultants, but they’re really excellent consultants, they walk the walk, talk the talk. They’re working on projects in New York, in Kansas City, they get it. But consultants are only good as the input they’re given, and so they were given kind of a narrow view of how to look at that. And basically, most of the developers said, ‘Look, we don’t care if there’s a stadium or not, we can work with or without it, but I think it should be jobs focused.’ But jobs can take a lot of forms, we’re thinking of companies, but they can be universities, hospitals. And they create an environment with ten or 20,000 jobs, and maybe create one of the greatest K to 12 schools, that all the people that work there wanna send their kid there, and really do top world class education, business environment. Look at what we’re doing around the world in terms of an attractive business campus. And not to worry about residential, not to worry about all these other side shows, but really talk about jobs. Because one of the few things that’s gonna be the major head wind in the development of the St. Petersburg area, or Tampa Bay area, is great jobs. We’re building all these expensive apartments, but who’s gonna live there? We gotta get these millennials and others that are gonna come and get six figure jobs. You can’t afford a $2,000 or $3,000 a month apartment earning $40,000 a year. So, we wanna attract these people who do wanna move here because it’s a very cool place. But they have to have excellent, accessible jobs. And they don’t wanna get in the car and drive somewhere, they wanna be able to walk, or take a driverless car, or take an Uber, or take something to their job. And I hear that constantly from employers and CEOs, that it’s hard to find these people and hard to find people that can get there.

Ashley: I wanna get into your mind a little bit. So, you were in the Chamber, President…

Craig: It’s a big area to get into.

Ashley: I’m lost, I don’t know how to get out now.

Joe: Echo, echo, echo.

Ashley: So, I’m thinking… So, from your vantage point serving as President of the Chamber a decade or so ago, is this what you visualized for where we’d be today? Has your bias been confirmed to date, or you’re surprised with what you’re seeing?

Craig: I’m excited by what we’ve done and are doing, but little bit nervous about the future. In other words, when I moved here in 1981, it was a waste land. There was no reason to come to downtown St. Pete, literally no reason. And then there were a lot of catalysts to grow this great place, whether it was the renovation of the Vinoy Hotel, whether it was the Rays, the Dali Museum, a lot of things. One of the things we did, probably people forget all about it or don’t understand is Baywalk. We were the creators of Baywalk, which I think was one of the catalysts to growing downtown St. Pete. It became the town center, and even though it morphed into Sundial and all that, it was extraordinarily important, it kind of put us on the map. The other thing we did, our company, the Sembler Company, which isn’t though about but it was just as important, is we built a Publix downtown, we built a Publix and a CSV in downtown called the University Plaza. And what it did, it would validate living downtown was okay, because it added that missing ingredient of being able to walk and get groceries. And it really spawned a lot of development. The other thing we did, we’re one of the partners at Innovation, which was probably, and still is, the nicest residence downtown, maybe until One gets done or whatever, and the who’s who of town moved there. And when that also validated that it’s okay to live downtown, and so we all dreamed this and there were a lot of people part of it, but one of the things we’ve lost over the years is great local community leadership, because a lot of times the companies either got absorbed in other companies, or moved out of town. And we don’t have as many great local leaders, and the ones we have had are all aging out, the Tom James’s and the Bill Hoffman and Mel Sembler’s, and these great people who are legends and role models for us all. And I don’t see a great bend strength of my generation and younger that can carry that panache. And if there’s anything I’m envious of Tampa, that’s that where they have a multitude of business men and women.

Ashley: So, take us if you will into the leadership qualities, I should say, that you valued in Tampa Bay, that is potentially…

Craig: I think you want people that number one, feel it’s their obligation to do that for whatever, for sense of self, for sense of community, for their family. Second is you want people in the sports analogy who want the ball. I’m not a good person to be second or third, because I get frustrated. And then there’s other people very happy to be second or third, and you want those people as well. So, you want people who want the ball that are push the agenda forward, and not just to be a leader to build their resume. I did that early in my career, it’s great to say I’m a President of this and the Chair. But after a while you say, ‘Enough of that!’ I don’t even know if I even still have a resume, but it’s what you wanna do to do some heroic things and really take an institution from down here to up here. The perfect case is All Children’s Hospital, we’re getting on the national notoriety of doing great things. It took a number of great leaders and I was not one of them, but at the board level and the executive level to do that. I’m involved with Tom James and building his museum, I don’t know if you’ve heard of it, but it’s the James Western Museum. In fact, I’m going now to a meeting. But it’s heroic. And he said, he and his family say, ‘We’re gonna fund it, we’re gonna design it, we’re gonna build it, because it’s our community, we’re gonna make it happen.’ He and Bill Hoff did the same thing at the Dali Museum with the others, they said, ‘This is important, we’re gonna make it happen.’

Joe: I feel like there’s a nuclear go-go-go, but obviously, you also don’t wanna step on toes, and when you don’t have the place to play and say, ‘I’m gonna pay for this and make it and I know it’s a good thing and it doesn’t step on anyone’s toes.’ What’s your life advice for doing that?

Joe: I think you need to collaborate. One of my frustrations is there’s so many people trying to do similar things, and they’re all good people. I’ll give you an example: food banks. You know how many food banks there are in Pinellas County? It’s gotta be dozens, hundreds. If they could help consolidate and eliminate overhead, and distribution and make it happen– you find that in social services, a lot of people are trying to do the same thing, nobody getting on the same page. And because life is full of limited resources, whether it’s leadership or capital, we can’t squander that person’s capital. So, my idea for you is try to collaborate with as many folks as you can and try to get on that same page, change minds. Everyone gets frustrated when the city or leadership doesn’t want to do that thing, but you gotta walk a mile in their shoes, they try and do 100 things, not 1000 things. There’s only a limited amount of money. I think my wife and I counted up last year, we gave to 72 charities and then everyone’s upset when you don’t give to their charities, and we’re thinking we maybe ought to give to ten charities, but give more. You gotta walk a mile in the other person’s shoes. On the other hand, old folks like me and other leaders need to step aside to some degree and allow good folks like you to move in and… because my kids would say, ‘Dad, you just don’t get it.’ Well, that’s true. I don’t get technology, I don’t get the new way of thinking, I don’t get not working in an office and working from home. And so, folks like you can pave the way to make things happen, so my advice is keep it up, try to collaborate and bring people in, so you’re building a bigger engine.

Ashley: I wanna stay on the note with collaborations and non-profit space. But are you seeing the traction with these entities? Or, what’s missing from some of the presumed solutions that our community, regionally and locally, have a need?

Craig: I’ll give you an example in the Jewish community. We just recently—it’s very timely, we commissioned a Jewish demographic study to determine the character and the population of the Jewish community in Pinellas County. Because we were finding probably most religions whose interest in Judaism and religion is waning. But we provide a lot of social services, we have a limited amount of resources, and are we spending them in the right way? So, we’re gonna create a task for us to examine all that, put it under one umbrella and try to realign things. That needs to happen in all communities. I think at some point that’s a point that government can help lead, but there’s so much money in  grants, and Pinellas County doing things, St. Pete doing things, but nobody is overall coordinating it, whether it’s—all sorts of social services. I’ll give you an example. I sit on the Lightning Community Foundation, Tampa Bay Lightning. We’re the ones who award the Lightning Community Heroes, I don’t know if you’re familiar with that, but we give $50,000 a game to a hero. I think in our seventh game…

Joe: What…?

Craig: A game. We’ve given 12 or 13 million dollars of Jeff and Petty Vinik’s money, $50,000 a game, to a hero.

Ashley: What do you need to do to qualify as a hero?

Craig: Well, it’s a great question. Number one, I go to their website, there’s an interesting application that’s not that onerous, and we constantly debate what a hero is. Early on, seven years ago, we gave to a lot of military and first responders and classic heroes that go into a burning building and pull out children. And then we said, ‘Not so much there, because that’s their job.’ And now we do a lot of grassroots organizations that do heroic things, whether it’s feed the hungry, clothe the poor, or mental health. You go on the site and you’ll see every hero we’ve given.

Ashley: They are essentially volunteers there, right?

Craig: Almost all of them are volunteers. We tend not to reward paid executives, we wanna do heroic volunteers, but we’ve given I think some close to 300 awards, and my point being you look at the overlap. We might have given—I’m gonna make numbers up, 25 or 30 to people interested in food, 25 or 30 interested in mental health, maybe 25 or 30 related to immigration and refugees, settlement and… And there’s so many people trying to do the same thing, and it hits us all that where is the alignment of let’s all work together? We’ve tried a few times in putting all the heroes together, and have them talk to each other, to try to say, ‘Well, I can help you with that,’ or ‘We can do that.’ To try to eliminate this overhead. And it’s the metaphor of what’s happening on the economic development, there’s so many people trying to do the same thing.

Joe: There is a, I would say… the business landscape is running somewhat counter to that, I think the larger corporations, obviously some of them transformed into your Amazons and Walmart’s, and there’s been some consolidation there. But a lot of the bigger, classic corporations are giving way to the smaller nimble ones, like the Ubers, taxis losing to Uber, hotels losing to Airbnb and so on and so forth. Because they’re not innovating, instead of innovating themselves out of business, somebody else is doing it. It depends on the goal, right? So, granularity has its value, especially as you get bigger, groups become underserved inside of those because of the priorities of the leadership, or even just the nature of bureaucracy itself. And so, with economic development I can certainly see speaking as a whole service area, economic area with food banks and things like that, then certainly economies… so, you might find hybrids where you get economies in the food storage, everybody uses a central place that they can pay into, and reduces all their overall costs by 20%. So, I think of it as a hybrid.

Craig: Sure.

Ashley: I think it’s solving for redundancies, but also solving for interdependencies, and I think that that’s what the Foundation for Healthy St. Pete and others are looking at. So, how disease prevention coalesce into homelessness, which coalesces into job readiness, so there’s a way for unrelated parties and entities to come together, so it’s not just too many food banks, but very different entities?

Craig: I hear they’re doing heroic and legendary work, they’re really smart people on that, and they’re deciding how to allocate many millions of dollars a year in very meaningful ways. So, I am all for that. But back to economic development, I don’t know how many different groups can go to a convention to attract the people. I’m of this philosophy, let’s get them attracted to Tampa Bay and then we fight for where they go, rather than let’s try to get them to come and see St. Pete. Well, I have no problem competing against Tampa, or Pasco or whatever. Just bring them here. Because if they’re doing their job anyway, they’re driving around anywhere. I can’t believe there’s a relocation consultant that’s just gonna go to Central Avenue in St. Pete or Dale Mabry in Tampa or that. They’re gonna see the whole area, or they’re not doing their job.

Joe: Ideally that same logic holds, you have some economies and market in the area, and then you have some pieces carved off. So, get them here and then let people compete within the area.

Craig: Absolutely.

Ashley: I wanna talk about local politics first, but it’s a different type of political question. So, people allude to St. Petersburg as being a big little city, or a little big city, and I would think that intrinsic to that, from a political positioning perspective, is the need to play in your own lane.

Craig: The parties in politics locally is irrelevant, except for the fact you have to get along with everyone who has funding sources. It’s a myth that the mayor’s race is not partisan… Yeah, technically, but you want someone who is going to be able to track federal and state and other regional support and grants and all that, so it’s not necessarily true that it’s a hire, or this is irrelevant, but you’d better get along with those who write big checks to your area, whether it’s in terms of grants, or whatever. One of the greatest heroes is hopefully not forgotten, but in my mind the greatest citizen of Pinellas County in the last century is congressman Bill Young, may he rest in peace. Call it pork or whatever, but he brought billions of dollars to this area, whether it’s defense and bridges and roads and programs… That was extraordinarily important. We wouldn’t be nearly the county we were without him. We don’t have that kind of crowd anymore, it’s hard to do, but he literally saved MacDill many times from the chopping block and other things, and he is really worthy of praise. So, I know people don’t like to get involved and talk about politics, but it’s extraordinarily important to have strong local leaders that can advocate for our city and our region.

Joe: When we talked about this podcast originally, and one of the things I wanna be a champion for is objectivity, and the shtick was gonna be we were gonna have two guests on, only say the first name, not in any way talk about where they’re from, what they’re involved with, what their opinions are, and challenge them to speak objectively about issues, and then hope would be at the we’d reveal who they were. Because now the opposite of that happens, right? You come on this show, on one of the news channels and they say who you are and what you are, and immediately pigeonhole them and you shut down if they’re not on your side. And so, this is not an alternative to the political needs that you need to talk, but I think we’re about held up to this point.

Craig: Well, we’re all generally pulling together for the same issues. Maybe how you approach it, but… What we do, whether it’s to build sewer systems, to build economic development, to build piers, to build police stations, to make sure we have a seamless city, to making sure we have great education are generally nonpartisan issues. And it’s gratifying, it’s nice that it’s treated that way. And then every four years we have some mayoral races city election that determines who the next set of leaders are, and then it kind of goes away. So, I think at the local level, I don’t think that it’s great, it’s just I would hope we have more and better leaders, and make it not so distasteful to lead, so that we have the best and brightest help to lead. And it’s very difficult. They already asked me one time, ‘Why don’t you run for mayor?’ I said, ‘Well, I have a great excuse: I don’t live in St. Pete.’ I live in St. Pete Beach, but I said if I was appointed I would serve, I would just not gonna go through all the machinations of fundraising, and… A very strong leader is willing to try to lead. You don’t get that very often.

Ashley: I wanna piggyback on Joe’s comments about objectivity, where I think that there is definite value to that perspective, but I’m curious as to whether you think that there’s brilliance in subjectivity, and that there… You look at our generation once or twice removed. Are you cautioning us to not fall into a land of neutrality or a land of political correctness, and to embrace subjectivity, embrace our beliefs? You pick a lane, right? And so, I don’t know if objectivity is quite where you play.

Craig: I started out as being objective, and then you pick a lane and you’re an advocate. I view myself as a passionate advocate for a variety of things. It may not be popular, I don’t poll test my positions, but you’ve got to be an advocate, otherwise nothing will ever get done. If everyone was objective and neutral, we would just live in this ongoing highway going to nowhere.

Ashley: Do you see us adopting those qualities, or are we…?

Craig: Us being?

Ashley: The bench that you’re observing from your vantage plane.

Craig: That’s interesting. I don’t know yet, because I don’t know a lot of your generation that are jumping in and achieving the position of leadership yet, I see them being in mid-levels. But political correctness is an interesting word, I just want civility. I’m a huge Bruce Springsteen fan, people would say I’m a zealot for Bruce Springsteen, I’ve seen him over 40 times. And I happened to get lucky and see his Broadway show the night before it opened, and he made one statement that was a very non-political show, he goes, ‘Hopefully this is just a bad chapter in human history.’ And so, I can sleep at night a little better thinking maybe it’s just a chapter with an end. But regardless of how you feel about what’s going on, we have to return to civility, we have to learn to listen in and not quickly moving to some corner and not listening to the substance of the argument. And so, I think fortunately at the local level we have that. If you are permeating throughout society, now that everyone is moving to some polarized corner, but it’s not okay to be nasty, and it’s not okay to tell lies, and it’s not okay to be a racist, a bully. And whatever -ist you want to put on it, we have to be civilized to each other, and it’s not okay to be a misogynist. We can’t get away from that, I don’t buy the argument where, if we achieve a certain policy and all that, it’s okay.

Joe: I agree and I wanna clarify objectivity, because it’s not the opposite of advocacy. It is the opposite of polarization, right? The idea is that we have so much polarization, leads to efficiency if one side is winning, but if they’re not then it leads to gross inefficiency. And so, by coming together with objectivity as a goal, then the idea is to increase efficiency.

Craig: I’ll give you an example. I’ve been by most measures a successful businessman, and I lived in a world of development, buying land, selling land, making deals. And my personal favorite technique in making a deal, and it applies to everything in life, whether it’s a relationship with a spouse or whatever, is let’s figure out what we’re gonna agree on. So, when I try to buy a piece of land, I always knew the only thing in their mind was they wanted a big price for the land. So, I always put that to the end, and I always start out, ‘Okay, is today Wednesday? Okay, that’s good, we agree on that.’ ‘Is it cloudy?’ ‘Oh, yeah, it’s great, it’s cloudy.’ ‘When do you want to sell your land?’ ‘Well, I’m thinking about next January.’ ‘Okay, we can agree on that.’ And then at the end you get to the price, and it becomes a much easier, at least your single focus is invested in it. And any of these things, I just agree and identify and plead to what we agree on, then we’ll worry about the couple of things we don’t agree on.

Joe: So, I don’t know if you’re gonna let Ashley out of your head if you don’t talk about Trump for a second. I’d like to phrase the question as not what do you think of Trump, I would like to phrase the question as why did Trump get elected?

Craig: I think a lot about that, and there’s a number of answers. I don’t know if you’ve read the book ‘Hillbilly Elegy’, it’s a very interesting book. And it talks about the white folks in Kentucky, in Ohio and all that, those that have had a very difficult time in life. Some would argue the mainstream of America, but they’ve had broken families, they’ve had jobs whose industries long left, they’ve had opioid addictions and all that. And that’s kind of a metaphor for a lot of people in the United States who have difficult lives. And I think Trump appealed to the people that said—and he kind of said this a few times, and also to the African-American population who had high unemployment, high crime rates, and so he goes, ‘What do you have to lose by voting for me? All these other people, men and women for generations, promised you this and promised you that and what do you got?’ And I think he pounced on a lot of that. Unfortunately, what went along with that was the negativity, pitting one against other, race against race, old versus young, immigrants versus… and it really appealed to some difficult feelings in the United States. The other thing was the arrogance of my party, the Democratic Party, and probably Hillary Clinton and her team, that ‘I can’t lose’. And she didn’t learn from the other 16 or 17 people on the stage who probably (and the Republicans too), ‘So, how is he doing this?’ And it was really a phenomenon, and hopefully a one-shot wonder but he is a nuclear bomb, but not necessarily a positive one. So, he came in and said, ‘What have you got to lose? Blow it all up!’ He is a master at deal making, unfortunately not everything in public policy is a deal. And to repeal and replace sounds good, but replace with what? He didn’t care, just signed replace. He wants tax reform. Well, he doesn’t care necessarily, he just wants to check off deals. It’s very disconcerting, I come from a point of view trying to be objective, that it’s a character and quality and morality of our leadership that is a role model for all of us, and that trumps some of these policies. So, I am not of the belief that, just because you can get something done, means there’s any means for that. And my favorite metaphor right now is—I know it’s a harsh one, I said, ‘If you’re in the population control, then Hitler is your guy, because he did a great job of certain population control, or Pol Pot, or whatever. Well, if you wanna keep the population down, no, that’s not okay. So, I want people that my grandchildren can say, ‘I wanna be like him and be President.’ I’m not sure that’s the case right now. I’m just—a personal anecdote is my wife and all her relatives and my six-year granddaughter went up to the Woman’s March in Washington. So, our six-year old granddaughter went there, and then we went after the horrible Charlottesville incident, there was a vigil down in St. Pete on the water and there were some religious leaders, we took our granddaughter. And unfortunately, my son-in-law two days later had to answer the question from a six-year old, ‘What is a Nazi, dad?’ And for a young Jewish girl, or anyone, to have to ask their father in this day and age what is a Nazi, it’s horrifying, it’s not okay, there’s not a lot of fun people on both sides, I don’t buy that argument. So, this is not a political thing, because I asked all my friends who support Trump, God bless them, it’s their right. If he had a D after his name would you support him? And they don’t wanna answer that question. Well, to me it’s irrelevant if it’s a D or an R.

Joe: Do you see his disruption of the kind of personality you can be, and still get elected as potentially a silver lining that will allow people who aren’t as stoic and vanilla, and maybe changing the landscape of having to say nothing so that you don’t say the 40%, or the deplorables or whatever that people say and lose elections because?

Craig: I think if he’d done it in a different style, where there was possible, there’s a real place for that. Because I can see the point of I’m just tired of another Bush being in there, or another Clinton. Those weren’t great choices, and this isn’t a political statement, it’s true. I mean, it’s the same old, same old 70-year-old person coming in and whatever you’re side on, either doing a lot for the country or doing that. So, people were ready for a change, and they went through Obama hoping change, and by and large for a lot of people it wasn’t what they wanted, so they’re ready for change again. History will judge whether this is a change that they wanted, but it’s okay, again, to blow it up. We first started and start over because straight old party politics isn’t getting us very far. So, I’d argue we need three parties, or four parties, who knows? In Israel they wanna go from four parties to two parties. We still are the greatest country in the world. I’m not sure the rest of the world is agreeing with that right now, I do a lot of traveling overseas and we’re not looked upon very favorably at the moment, that’s disturbing. But maybe there will be a silver line in there somewhere, but it’s really painful right now.

Ashley: Craig, we like to wrap the show putting the limelight on an entity or an individual who may be someone under the radar. I know that you’ve got your finger on the pulse of this city and this region. Give us a name or two.

Craig: One of my favorite people in the world that actually would probably be mortified that I’m mentioning her name is Beth Houghton. I don’t know if you know Beth, but Beth is the Executive Director of the St. Pete Free Clinic, been my partner in business, helped make All Children’s what it was and what it is, has been the chair of Moffitt for a number of years, certainly didn’t need the job for the pay, but has been at the Free Clinic just because she’s a wonderful person, the goodness of her heart, and has rebuilt the Free Clinic into a wonderful organization, so I have a lot of affection for her, she’s great and we need more leaders like that, she is just remarkable. There’s a few people like that. A guy like Tom James, I don’t know if everyone knows Tom James, but he’s one of my personal business and community heroes. He’s the guy that utterly is a wealthy man by any measure, but he and his wife do wonderful and heroic things for the community in every regard. You see him under the radar, and a very simple man, simple people, and they’re probably to me, our generational most important players to do that. So, I have tremendous respect for he and his wife and his family. We need more people like that, willing to literally devote their lives to making our community better.

Joe: We appreciate your time, it’s been a pleasure.

Craig: It’s been fun.

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About the host

Joe Hamilton is the CEO of Big Sea and a founding Insight Board member at the St. Petersburg Group.  Joe brings a strong acumen for strategy and positioning businesses. He serves on several local boards, including TEDx Tampa Bay, which grew his desire to build a platform where the area’s thought leaders could share their valuable insight with the community at large.


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