Craig Holland | Crain's Orlando

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Craig Holland


A 17-year city veteran, Craig Holland has overseen the transformation of downtown Kissimmee since 2014, including the $65 million Lake Toho Master Development known as the Mosaic project, now underway. Named one of 2016's top 10 U.S. boomtowns by SmartAsset, Kissimmee, Florida, had the highest housing growth rate among ranked cities.

The Mistake:

The big mistake I made was coming into the community thinking that I knew how to make everybody’s life better from outside the community. I moved here from Arizona, and I’d lived all over the country – and you’d think I would know better. At the time, I didn’t know I was going to make Florida and Kissimmee my home.

I came in and I thought, “I’ve got a lot of experience. I’ve seen a lot of different communities.” The last community I was in was very similar to this one. I thought, “I know exactly what’s wrong, and I know how to fix it.” So the first several years with that kind of attitude was kind of an uphill battle. "I’m here to save the day” is basically the attitude I had.

And I began to realize that I really didn’t have a clue. It wasn’t until I moved to Kissimmee. I’d lived in Orlando for seven-ish years, and now I actually live downtown in the heart of Kissimmee. That’s when it kind of clicked. I don’t know if it’s because I cared, not that I didn’t care before. I did. But it was like, “Now I am invested and I have a family here.”

Once you move here, you kind of get to know people that you see day-to-day. Whereas [before], at five o’clock I was headed back to downtown Orlando. I began to see the immense amount of diversity that we have here. And that kind of hammered home the point that we have so much diversity and we’re [also] trying desperately to hold on to what we had for 100 years before that. We were an old cattle town. We were kind of a big deal until Orlando took off. And now we’re the second biggest town in Central Florida, population-wise.

'I’m here to save the day' is basically the attitude I had.

The Lesson:

I definitely look at issues differently because I live here. There’s a certain amount of pride in your community. Before it was more pride in workmanship. Now it’s more “pride of home.” So that shift in thinking has helped.

When I didn’t live there, I didn’t understand the changes we were going through. In the 17 years that I’ve been with the city, we’ve gone from diverse to extremely diverse. It’s grown exponentially. So I see the way people want to hold on to the historic part of Kissimmee, but at the same time welcome the diversity.

Once I moved here, I saw firsthand what my neighbors were telling me. They’ve seen all these changes and they hope we can hold on to all that – especially now that we have a $65 million development, which is so different from what you see in our downtown. I go out to rake leaves in my front yard and [neighbors] walk by and ask, “What’s going on?”

And my perspective is unique in that I have a partner who’s a firefighter for the city. So we both work for the city. And we try to immerse ourselves – we volunteer. And you show up for things because it’s where you live and you want it to be great. And you want people to see that.

I’m a lot more accepted now. I’ll do a presentation and I’ll say, “Not only do I work for the city, I live in town.” And there’s a sigh of relief. People think, “Oh, he lives here. He understands what we’re going through.” Sometimes I have to say, “This is why this is happening and this is why it’s going to help.”

And so with my experience of living here and in Orlando and just a little bit of maturity, I’ve learned [to say], “Let’s look at this and discuss this all the way through” instead of, “I’m here to save the day.”​

Follow the city of Kissimmee on Twitter at @Kissimme_gov.

Photo courtesy of Craig Holland

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