Hiring in Tampa Bay's Tightest Labor Market

Tampa Bay's labor market has tightened every year since 2012. Population is up—we've seen that migration wave from the North and Northeast. Wages are up. Turnover is real. In 2012, you could post on Indeed and get 40 responses by Monday. By 2022, you got 4, and one of them was a bot.

Over the past 12 years, we've hired more than 250 people across six different companies. Insurance, construction, real estate, podcast production. Different industries. Same problems. I've learned what actually predicts whether someone is going to stick around and perform, and what's just noise.

Character Over Pedigree

The first thing I stopped doing was screening for credentials. I don't care if you went to FSU or UF or if you got your insurance license on the first try. Credentials tell you about one test someone passed. They don't tell you if you can trust them, if they'll show up when something breaks, or if they'll keep learning after they're hired.

I screen for two things instead: character and urgency.

Character is whether someone does the small things right. Did they show up five minutes early to the interview? Did they ask intelligent follow-up questions, or were they waiting for me to tell them what to do? Did they own a mistake they made, or did they blame someone else? Did they ask about the job, or did they only ask about the benefits?

Urgency is whether they act like they actually need the job. That's not about desperation—it's about whether they're in forward motion. Are they working toward something, or just filling time? A person with urgency moves through problems. They don't wait for permission to figure things out. They ask "What's the next thing?" without being asked.

I've hired contractors with high school diplomas who outperformed people with graduate degrees, because the person with the diploma had character and was moving. I've let go of people with spotless resumes who treated the job like they were doing us a favor.

The First 30 Days Are Everything

This is the one I will not budge on. How someone performs in their first month tells you 90 percent of what you need to know.

Here's the routine I use: I assign something slightly above their skill level within the first week. Not so hard they fail, but hard enough that they have to stretch. Then I watch three things.

First, do they ask for help, or do they figure it out and then ask? The people who try to solve things first and come back with questions learned something. The people who ask before trying anything are going to need to be managed intensely.

Second, when they hit something they don't know, do they blame the system or do they assume they're missing something? The person who says "I don't understand the filing process" and goes to find the manual is someone you can trust. The person who says "This process doesn't make sense" on day four is someone who will spend their whole tenure complaining instead of learning.

Third, do they follow up without being asked? At the end of the first month, does someone come to you and say "Here's what I've learned, here's what I'm confused about, here's what I think I'm ready for next"? That person is in the building. The person who just shows up and waits for direction is a hired gun, and they'll leave the second something better looks easier.

By day 30, you know. If they don't have character, if they're not urgent, if they're not reflecting on their own learning—they're not going to stay. So I don't wait until month six to have that conversation. I have it in month one.

Why I Stopped Posting on Indeed

This is going to sound tribal, but it's actually just pattern matching. Everyone in Tampa Bay is on Indeed. The candidates you want—the ones with character, the ones with some experience—are also on LinkedIn, are also getting called by recruiters, are also getting offers from other companies. If you're waiting for them to apply to your Indeed post, you're too slow.

What's actually worked is hiring from within the customer base. If you run a business, you meet hundreds of people a year. You see who treats you fairly, who shows integrity in how they negotiate, who asks smart questions about what you do. Those people often don't have their resume ready. But the ones who do can be incredible employees because you already know something about how they operate.

At Star Insurance, some of our best long-term hires came from customers who'd been calling with renewal questions. They were curious about the industry. They understood the problems. They had a network already inside the business through their own dealing with us.

The same thing happened in construction. We hired people we'd worked with—subcontractors we'd been partnering with, people on job sites who impressed us. They came in with real skills and, more importantly, they came in already understanding the business culture because they'd been working alongside it.

Why the Tight Market Actually Favors Operators

Here's the thing most people get wrong: when the labor market is tight, the people complaining are the ones who were always going to be bad managers. The people who are winning are the ones who were ready for it anyway.

If your business depends on finding 30 incredible people, you probably can't. But if it depends on finding 10 incredible people and having them manage systems and workflows that other people can execute—that's doable. The tight market forced me to be clear about what I actually needed someone exceptional to do, versus what I could build a system around.

The labor shortage became a filter. It got rid of the managers who wanted to blame hiring for their problems, and left the ones who had to become better operators.

At Embassy Construction, instead of trying to hire 20 general laborers, we built the workflow so that five people could coordinate more volume. It was slower at first. But within six months, we were moving more projects with fewer people than we had been before.

The second thing the tight market did is it made me value the people who did stay. If someone has been at Star Insurance for five years, I'm not going to lose them over a small raise or a schedule change. The cost of replacing them is astronomical. That changes how you think about compensation, flexibility, and attention.

Still Going

We're still hiring—slower now, more carefully, sometimes with months between openings because we don't want to bring someone on unless they clear the bar. And the bar is still: Do they have character? Are they urgent? Will they be better on day 30 than they were on day one?

Everything else is secondary.