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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Airbnb says more than 1,300 apartment and condo buildings in 75+ markets let residents host part-time (Nov 2025).
If rent is your biggest bill, check that list before your next lease.
Already renting? Free playbook:
go.cashflowdiary.com/n04-130…
"Most people get stuck on Airbnb and vacation," J. Massey said on a call this October.
A direct booking site won't fix that alone. Guests who aren't on vacation (a surgeon on rotation, a work crew) need to know you exist.
Free diagnostic call:
go.cashflowdiary.com/n03-stu…
Planning a direct booking site? Read Airbnb's Off-Platform policy.
It bars asking guests to rebook off Airbnb, outside links in listings or messages, and discounts for booking elsewhere.
Direct guests find you another way. Free diagnostic call:
go.cashflowdiary.com/n03-pol…
Americans saved 4.1% of after-tax income in August (BEA).
With margins that thin, fees count. On a $2,000 booking, Airbnb's 15.5% host fee is $310. Card processing on your own site is about $58.
Free newsletter with numbers like these:
go.cashflowdiary.com/n03-sav…
Airbnb says its 15.5% host fee covers payment processing, marketing and 24/7 support.
Book a guest on your own site and all three are yours, down to who answers at 2 AM.
Price those first. Free diagnostic call:
go.cashflowdiary.com/n03-fee…
Credit card accounts paying interest averaged a 22.36% APR in August (Federal Reserve).
Hosts pay a cut too. Most now pay Airbnb a single 15.5% fee, so a $1,000 booking pays out $845.
Know what each channel costs you. Free diagnostic call:
go.cashflowdiary.com/n03-apr…
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…
