Curtis Grimes is a Florida real estate professional with 20+ years of investing experience. He's a licensed Realtor in Florida, a certified general contractor, a certified home inspector, and a certified elevator instructor. Curtis and his wife work as a team under "The Grimes Group," with Curtis primarily focused on buyers and his wife primarily focused on listings.

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Key Takeaways

Avoid overextending and keep capital in reserve so you can survive downturns and stay in the game
Treat real estate like a real business: track overhead, know your numbers, and manage cash flow consistently
When converting a home into a rental, lead with the numbers, the long-game use case, and the HOA/condo rules that can limit renting
In vacation-rental markets, price and occupancy fluctuate, so model seasonality and make sure you can still cover overhead during slower months
Build stability through disciplined lead generation, financial planning, and repeat/referral relationships that compound over time

Topics

From Queensbridge to Florida real estate

Curtis shares his early background in New York, the move to Florida, and how he and his wife built their real estate path together

Surviving 2008 and rebuilding with resilience

Losing properties and even a primary residence, then continuing forward by downsizing, consolidating, and planning for recovery

How to avoid "feast or famine" as an agent or investor

Why lead generation, budgeting, and running operations like a real business matters more when the market slows

Vacation rentals and seasonality in Orlando

Stabilizing rents and home prices, plus how peak and off-peak seasons affect pricing strategy and returns

Converting a home into a rental

How to think through valuation, numbers, demand drivers, and especially HOA guidelines and rental restrictions

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Round of Insights

Failure that set Curtis up for success: 2008, and the reset it created around reserves, resilience, and never being caught without enough overhead coverage again.

Digital or mobile resource Curtis recommends: He suggests reaching out to The Grimes Group directly for market data and updates.

Book Curtis has recommended or gifted the most in the last year: Shift and The Psychology of Money

Daily habit that helps Curtis stay focused: Creating a routine, waking up early, starting the day with gratitude, and structuring his mornings around calls and appointments.

Favorite restaurant in Orlando: Chili's.

Next Steps

Reach out to Curtis via e-mail.
Check out the website to learn more: Link
Review your personal and business reserves, and define the minimum cash cushion you need to survive a slow market
Write down your monthly overhead and track it like a business (not "whatever is left is profit")
If you're considering turning a home into a rental, verify HOA/condo bylaws and rental restrictions before you commit
Model seasonality if you're underwriting a vacation rental, and pressure-test your numbers in slower months

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