Avoid “Feast or Famine” as an Agent or Investor with Curtis Grimes, Ep. 780

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

• 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

📢 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

• 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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