Feb 17, 2026
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.
Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.
Key Takeaways
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Avoid overextending and keep capital in reserve so you can survive downturns and stay in the game
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Treat real estate like a real business: track overhead, know your numbers, and manage cash flow consistently
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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
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In vacation-rental markets, price and occupancy fluctuate, so model seasonality and make sure you can still cover overhead during slower months
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Build stability through disciplined lead generation, financial planning, and repeat/referral relationships that compound over time
Topics
From Queensbridge to Florida real estate
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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
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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
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Why lead generation, budgeting, and running operations like a real business matters more when the market slows
Vacation rentals and seasonality in Orlando
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Stabilizing rents and home prices, plus how peak and off-peak seasons affect pricing strategy and returns
Converting a home into a rental
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How to think through valuation, numbers, demand drivers, and especially HOA guidelines and rental restrictions
📢 Announcement: Learn about our Apartment Investing Mastermind here.
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
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Reach out to Curtis via e-mail.
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Check out the website to learn more: Link
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Review your personal and business reserves, and define the minimum cash cushion you need to survive a slow market
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Write down your monthly overhead and track it like a business (not “whatever is left is profit”)
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If you’re considering turning a home into a rental, verify HOA/condo bylaws and rental restrictions before you commit
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Model seasonality if you’re underwriting a vacation rental, and pressure-test your numbers in slower months
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