People talk about where they live the way they talk about a hobby — as something separate from the working part of their life. I’ve never found that to be true. Where you live sets your pace, your default conversations, who you run into, and how you think about time. It gets into the work whether you plan for it or not.
For Garrett O’Rourke, Miami Beach is less a backdrop than a working environment. He serves as President of Commercial Development Group, and his career has been built on sales, business development, call-center ownership and operations, and running teams. Those aren’t glamorous disciplines. They’re about repetition, numbers and people — which, oddly enough, is a good description of what South Florida teaches you if you pay attention.
Why Miami Beach, and what it actually teaches
The easy version of the answer is weather. The honest version is that Miami Beach is a city built on constant movement. Somebody is always arriving, somebody is always leaving, and the mix of people you’re speaking with on any given week changes more than it would in most places. You hear five accents at a coffee counter. You end up in conversations with people whose businesses have nothing to do with yours.
In my experience, that constant turnover of people is good for anyone who sells for a living. Sales work erodes when you only ever talk to the same twenty people. You start assuming everyone thinks the way your circle thinks. A city with a lot of movement through it keeps knocking that assumption down. You learn that what feels obvious to you is not obvious to the person across the table, and that the way you explain something has to change depending on who you’re explaining it to.
South Florida also has an unusual relationship with growth. Building here means dealing with water, storms, insurance, seasonality and cycles that don’t move in a straight line. Nothing about this place lets you assume that because a thing is going well right now, it will keep going well at the same rate. That’s a useful mental habit to carry into a business or a portfolio.
The pace is not the same as the productivity
There’s a stereotype about Miami that it’s all pace and no patience. I’d argue the opposite lesson is the one worth taking. The visible energy of the place — the traffic, the construction, the crowds in season — sits on top of something much slower. Buildings take years. Neighborhoods turn over across decades. The real estate that matters was decided on long before anyone noticed it.
One thing I’ve learned is that most people confuse activity with progress, and a busy city will happily encourage that confusion. Running a business teaches you that the things that actually compound are quiet: the training you did with a new hire six months ago, the customer you kept in touch with after they didn’t buy, the process you documented so the fifth person to do the job doesn’t have to reinvent it.
Call-center work makes this unusually clear. In that environment you can see a full month of effort in a single report. You learn quickly that the loudest day rarely produces the best number, and that consistency across a quarter beats brilliance on a Tuesday. That lesson transfers to everything else, including how you evaluate an investment.
Travel as a research method
Travel is one of the few things outside work that genuinely changes how I think about work. Not as a break from it — as a way of getting a second opinion on my own assumptions.
Every city solves the same basic problems differently. How people get around. How they eat. How business gets done, and how much of it happens through formal channels versus relationships. When you spend time somewhere that solves those problems in a way you’d never have chosen, you get a useful reminder that your own way isn’t the only functional one. That’s a hard lesson to learn from a book and an easy one to learn standing in an unfamiliar neighborhood at dinnertime.
A few things I pay attention to when I’m somewhere new:
- How service works. Is the person serving you empowered to fix a problem, or do they need permission? That one detail tells you a great deal about how the business is run.
- What gets built and what gets preserved. Architecture is a record of what a place decided to value, and what it decided it could live without.
- How strangers are treated. Cities that are good to outsiders tend to be good places to do business, because they’ve built the habit of assuming a new face might matter.
- What the food says. Food culture is usually the most honest thing about a city. It tells you about immigration, geography, income and pride, all at once.
Miami Beach itself scores well on most of those, which is part of the answer to why I’m here. It’s a place that has had to absorb newcomers constantly, and that absorption is now part of its character rather than a strain on it.
Practical lessons I’ve carried from here into the work
Some of this is soft, so let me make it concrete.
- Seasonality is real, plan for it. South Florida runs on seasons — busy months and slow months. Businesses that budget as though December and August are the same month get hurt. Most businesses have a version of this even when they don’t admit it.
- Build for the storm you haven’t had yet. Nobody here treats hurricane preparation as pessimism. It’s just maintenance. Cash reserves, redundancy in key roles and a written plan for when your best salesperson leaves are the same idea applied to a company.
- Assume the person in front of you has options. In a transient market, customers and employees can leave easily. That keeps you honest about service and about how you treat a team.
- Relationships outlast transactions. Over the years, the deals that came back to me came through people I’d stayed in contact with for no immediate reason. That’s not a networking tactic; it’s just what happens when you’re genuinely in touch with people.
- Don’t buy the narrative, check the numbers. Hot markets generate a lot of confident storytelling. As an investor, I try to separate what a place feels like from what the arithmetic actually supports.
That last point deserves a caveat. I invest in real estate and in public markets as a private investor, and everything I say about it reflects my own perspective and temperament — not individualized financial advice for anyone else. What works for my risk tolerance and time horizon may be entirely wrong for yours.
The part that isn’t about business
Not everything has to be a lesson. Animal welfare is something I care about, and it’s a reminder that the measure of how you operate isn’t only what shows up on a P&L. The way people treat the things that can’t advocate for themselves — animals, junior employees, a customer who doesn’t know what they’re buying — tells you most of what you need to know about them.
If there’s a broader principle underneath all of this, it’s that environment is not neutral. The city you live in, the people you spend time around, the pace you accept as normal — those things shape your judgment quietly and continuously. Choose them with the same care you’d give any other decision that compounds over twenty years. Miami Beach suits the way I want to think: open to new people, honest about cycles, and slower underneath than it looks.
Photo by Tetiana Sapon on Unsplash