Father, Real Estate Investor, Author, Educator, Speaker and Podcaster. Wholesaling, Raising Private Capital, Multi-Family and Commercial Properties.
West Palm Beach, FL
Joined August 2010
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J. Massey: "Every day, every physical day on the calendar is actually a holiday for somebody."
On their holiday, he says, guests pay more. Before you discount a slow month, check whose holiday falls on those dates.
Free diagnostic call:
go.cashflowdiary.com/n02-hol…
Before you cut price, open Airbnb's pricing tab and tap View similar listings. Pick up to 31 days and a map shows average prices nearby, booked and unbooked.
Compare yourself to the booked ones. That gap is your number.
Free diagnostic call:
go.cashflowdiary.com/n02-com…
13% of adults who never have money left at month end have 3 months of expenses saved (Federal Reserve, 2025).
If your rental cushion sits empty midweek, set the minimum by check-in day. Example: 2 nights Fridays, 1 otherwise.
Free call:
go.cashflowdiary.com/n02-wee…
Empty nights in the next 4 weeks? Airbnb's last-minute discount covers bookings made 1 to 28 days out.
At 10% or more off your 60-day median price, guests see the markdown in search. It's off while Smart Pricing is on.
Free diagnostic call:
go.cashflowdiary.com/n02-las…
About 9 million Americans held 2 or more jobs in September (BLS).
If your rental went quiet, try Instant Book, a fix that adds no hours. Airbnb says it helps your response rate, which can help search placement.
Free diagnostic call:
go.cashflowdiary.com/n02-two…
J. Massey on automation: "It doesn't mean that you're not involved. It just means you don't touch every dollar that comes through the door."
With a day job, that means a cleaner, a smart lock and scheduled messages.
Free diagnostic call:
go.cashflowdiary.com/n01-dol…
J. Massey: "If I wanted to spend four more hours a week or a month at my kid's school, what does that cost me?"
At $8 to $30 an hour, four hours cost $32 to $120.
Price a rental's hours before it joins a full-time week.
Free diagnostic call:
go.cashflowdiary.com/n01-hou…
Most of us wait to hire help until the money shows up.
Which chore would you give away first? Laundry, dishes, the errand that eats your Sunday.
A rental has jobs like that. Guest laundry can go to someone you pay.
Free diagnostic call:
go.cashflowdiary.com/n01-cho…
Airbnb lets hosts schedule quick replies that send on their own when a guest books, checks in or checks out (Airbnb Help Center).
Write those messages once. You can still edit or skip one before it goes.
Free diagnostic call:
go.cashflowdiary.com/n01-rep…
The clocks went back an hour overnight. One extra hour, once a year.
Full-time workers average 8.1 hours on the days they work (BLS, 2025).
The usual fix for a tight month is more hours. What could you hand off instead?
Free diagnostic call:
go.cashflowdiary.com/n01-clo…
Landlord: "Our attorney needs to review it."
J. Massey asks: "When your attorney says no, are we done? Yes, or no."
Now you know who decides. Our free 17-page playbook has 8 more answers:
go.cashflowdiary.com/m31-att…
Landlord: "Will you pay more rent?"
Plan to pay market rent, especially at first. Ask for a discount only if you sign for longer or take more units.
If they doubt you can pay, don't argue. Ask what would address it.
Playbook:
go.cashflowdiary.com/m31-ren…
A landlord's worry: "Won't guests wear out my unit?"
Most guests come to town for a hospital, a job or a conference. In J. Massey's model, stays run 4 to 6 days, with a full clean after each.
And say up front that locks get more use.
Playbook:
go.cashflowdiary.com/m31-wea…
Landlord: "I need background checks on everyone."
J. Massey's reply: on ten units, that's 30 to 40 checks a month. "What were you planning on doing with all of that information?"
Often the real need is the current guest's contact.
Playbook:
go.cashflowdiary.com/m31-che…
14 people on our list have written back with some version of the same fear: scared to ask the landlord.
That fear makes sense when all you bring is a hope.
Bring who would stay, who stays responsible and what the landlord gets.
Free playbook:
go.cashflowdiary.com/m31-sca…
J. Massey on rental property, in his course: "There's a reason they're called landlords."
The model is old. Short-term rental rules are newer and local, so check yours before you sign a lease.
Free diagnostic call:
go.cashflowdiary.com/m30-lan…
What counts as a short-term rental depends on the city.
Austin: under 30 consecutive days.
Berkeley: under 14.
(Both per the cities' own websites.)
Find your city's definition before you plan a booking.
Free diagnostic call:
go.cashflowdiary.com/m30-def…
Renting the basement for retirement income? Two calls before you list it:
Your mortgage lender, about limits on renting.
Your insurance agent, about whether your policy fits hosting.
Airbnb's Help Center suggests both.
Free diagnostic call:
go.cashflowdiary.com/m30-bas…
Your city's zoning code is probably online. Municode alone hosts about 3,900 local codes.
Search yours for "short-term rental," "transient" and "vacation rental," then email the permit office to confirm.
Free diagnostic call:
go.cashflowdiary.com/m30-cod…
The U.S. homeownership rate is 65.0% (Census, Q2 2026), so about 35 in 100 households rent.
If that's you and you've thought about hosting your place for extra money, read your lease first, then ask your landlord in writing.
Free diagnostic call:
go.cashflowdiary.com/m30-ren…
